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Glucose: Difference between revisions - Wikipedia

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<ul id="toc-Open-chain_form-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Cyclic_forms" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Cyclic_forms"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.3</span> <span>Cyclic forms</span> </div> </a> <ul id="toc-Cyclic_forms-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Mutarotation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Mutarotation"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.4</span> <span>Mutarotation</span> </div> </a> <ul id="toc-Mutarotation-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Optical_activity" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Optical_activity"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.5</span> <span>Optical activity</span> </div> </a> <ul id="toc-Optical_activity-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Isomerisation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Isomerisation"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.6</span> <span>Isomerisation</span> </div> </a> <ul id="toc-Isomerisation-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Biochemical_properties" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Biochemical_properties"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Biochemical properties</span> </div> </a> <button aria-controls="toc-Biochemical_properties-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Biochemical properties subsection</span> </button> <ul id="toc-Biochemical_properties-sublist" class="vector-toc-list"> <li id="toc-Uptake" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Uptake"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.1</span> <span>Uptake</span> </div> </a> <ul id="toc-Uptake-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Biosynthesis" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Biosynthesis"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.2</span> <span>Biosynthesis</span> </div> </a> <ul id="toc-Biosynthesis-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Glucose_degradation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Glucose_degradation"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.3</span> <span>Glucose degradation</span> </div> </a> <ul id="toc-Glucose_degradation-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Energy_source" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Energy_source"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.4</span> <span>Energy source</span> </div> </a> <ul id="toc-Energy_source-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Precursor" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Precursor"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.5</span> <span>Precursor</span> </div> </a> <ul id="toc-Precursor-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Pathology" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Pathology"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Pathology</span> </div> </a> <button aria-controls="toc-Pathology-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Pathology subsection</span> </button> <ul id="toc-Pathology-sublist" class="vector-toc-list"> <li id="toc-Diabetes" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Diabetes"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.1</span> <span>Diabetes</span> </div> </a> <ul id="toc-Diabetes-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Hypoglycemia_management" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Hypoglycemia_management"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.2</span> <span>Hypoglycemia management</span> </div> </a> <ul id="toc-Hypoglycemia_management-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Sources" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Sources"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Sources</span> </div> </a> <ul id="toc-Sources-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Commercial_production" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Commercial_production"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Commercial production</span> </div> </a> <button aria-controls="toc-Commercial_production-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Commercial production subsection</span> </button> <ul id="toc-Commercial_production-sublist" class="vector-toc-list"> <li id="toc-Conversion_to_fructose" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Conversion_to_fructose"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.1</span> <span>Conversion to fructose</span> </div> </a> <ul id="toc-Conversion_to_fructose-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Commercial_usage" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Commercial_usage"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Commercial usage</span> </div> </a> <ul id="toc-Commercial_usage-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Analysis" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Analysis"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>Analysis</span> </div> </a> <button aria-controls="toc-Analysis-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Analysis subsection</span> </button> <ul id="toc-Analysis-sublist" class="vector-toc-list"> <li id="toc-Classical_qualitative_detection_reactions" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Classical_qualitative_detection_reactions"> <div class="vector-toc-text"> <span class="vector-toc-numb">8.1</span> <span>Classical qualitative detection reactions</span> </div> </a> <ul id="toc-Classical_qualitative_detection_reactions-sublist" class="vector-toc-list"> <li id="toc-Fehling_test" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Fehling_test"> <div class="vector-toc-text"> <span class="vector-toc-numb">8.1.1</span> <span>Fehling test</span> </div> </a> <ul id="toc-Fehling_test-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Tollens_test" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Tollens_test"> <div class="vector-toc-text"> <span class="vector-toc-numb">8.1.2</span> <span>Tollens test</span> </div> </a> <ul id="toc-Tollens_test-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Barfoed_test" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Barfoed_test"> <div class="vector-toc-text"> <span class="vector-toc-numb">8.1.3</span> <span>Barfoed test</span> </div> </a> <ul id="toc-Barfoed_test-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Nylander&#039;s_test" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Nylander&#039;s_test"> <div class="vector-toc-text"> <span class="vector-toc-numb">8.1.4</span> <span>Nylander's test</span> </div> </a> <ul id="toc-Nylander&#039;s_test-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Other_tests" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Other_tests"> <div class="vector-toc-text"> <span class="vector-toc-numb">8.1.5</span> <span>Other tests</span> </div> </a> <ul id="toc-Other_tests-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Instrumental_quantification" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Instrumental_quantification"> <div class="vector-toc-text"> <span class="vector-toc-numb">8.2</span> <span>Instrumental quantification</span> </div> </a> <ul id="toc-Instrumental_quantification-sublist" class="vector-toc-list"> <li id="toc-Refractometry_and_polarimetry" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Refractometry_and_polarimetry"> <div class="vector-toc-text"> <span class="vector-toc-numb">8.2.1</span> <span>Refractometry and polarimetry</span> </div> </a> <ul id="toc-Refractometry_and_polarimetry-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Photometric_enzymatic_methods_in_solution" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Photometric_enzymatic_methods_in_solution"> <div class="vector-toc-text"> <span class="vector-toc-numb">8.2.2</span> <span>Photometric enzymatic methods in solution</span> </div> </a> <ul id="toc-Photometric_enzymatic_methods_in_solution-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Photometric_test-strip_method" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Photometric_test-strip_method"> <div class="vector-toc-text"> <span class="vector-toc-numb">8.2.3</span> <span>Photometric test-strip method</span> </div> </a> <ul id="toc-Photometric_test-strip_method-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Amperometric_glucose_sensor" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Amperometric_glucose_sensor"> <div class="vector-toc-text"> <span class="vector-toc-numb">8.2.4</span> <span>Amperometric glucose sensor</span> </div> </a> <ul id="toc-Amperometric_glucose_sensor-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Other_sensory_methods" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Other_sensory_methods"> <div class="vector-toc-text"> <span class="vector-toc-numb">8.2.5</span> <span>Other sensory methods</span> </div> </a> <ul id="toc-Other_sensory_methods-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Copper_iodometry" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Copper_iodometry"> <div class="vector-toc-text"> <span class="vector-toc-numb">8.2.6</span> <span>Copper iodometry</span> </div> </a> <ul id="toc-Copper_iodometry-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Chromatographic_methods" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Chromatographic_methods"> <div class="vector-toc-text"> <span class="vector-toc-numb">8.3</span> <span>Chromatographic methods</span> </div> </a> <ul id="toc-Chromatographic_methods-sublist" class="vector-toc-list"> <li id="toc-In_vivo_analysis" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#In_vivo_analysis"> <div class="vector-toc-text"> <span class="vector-toc-numb">8.3.1</span> <span>In vivo analysis</span> </div> </a> <ul id="toc-In_vivo_analysis-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span class="vector-dropdown-label-text">Toggle the table of contents</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading">Glucose: Difference between revisions</h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="Go to an article in another language. Available in 106 languages" > <label id="p-lang-btn-label" for="p-lang-btn-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--action-progressive mw-portlet-lang-heading-106" aria-hidden="true" ><span class="vector-icon mw-ui-icon-language-progressive mw-ui-icon-wikimedia-language-progressive"></span> <span class="vector-dropdown-label-text">106 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-af mw-list-item"><a href="https://af.wikipedia.org/wiki/Glukose" title="Glukose – Afrikaans" lang="af" hreflang="af" data-title="Glukose" data-language-autonym="Afrikaans" data-language-local-name="Afrikaans" class="interlanguage-link-target"><span>Afrikaans</span></a></li><li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%AC%D9%84%D9%88%D9%83%D9%88%D8%B2" title="جلوكوز – Arabic" lang="ar" hreflang="ar" data-title="جلوكوز" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-as mw-list-item"><a href="https://as.wikipedia.org/wiki/%E0%A6%97%E0%A7%8D%E0%A6%B2%E0%A7%81%E0%A6%95%27%E0%A6%9C" title="গ্লুক&#039;জ – Assamese" lang="as" hreflang="as" data-title="গ্লুক&#039;জ" data-language-autonym="অসমীয়া" data-language-local-name="Assamese" class="interlanguage-link-target"><span>অসমীয়া</span></a></li><li class="interlanguage-link interwiki-ast mw-list-item"><a href="https://ast.wikipedia.org/wiki/Glucosa" title="Glucosa – Asturian" lang="ast" hreflang="ast" data-title="Glucosa" data-language-autonym="Asturianu" data-language-local-name="Asturian" class="interlanguage-link-target"><span>Asturianu</span></a></li><li class="interlanguage-link interwiki-az mw-list-item"><a href="https://az.wikipedia.org/wiki/Ql%C3%BCkoza" title="Qlükoza – Azerbaijani" lang="az" hreflang="az" data-title="Qlükoza" data-language-autonym="Azərbaycanca" data-language-local-name="Azerbaijani" class="interlanguage-link-target"><span>Azərbaycanca</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%DA%AF%D9%84%D9%88%DA%A9%D9%88%D8%B2" title="گلوکوز – South Azerbaijani" lang="azb" hreflang="azb" data-title="گلوکوز" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-bn mw-list-item"><a href="https://bn.wikipedia.org/wiki/%E0%A6%97%E0%A7%8D%E0%A6%B2%E0%A7%81%E0%A6%95%E0%A7%8B%E0%A6%9C" title="গ্লুকোজ – Bangla" lang="bn" hreflang="bn" data-title="গ্লুকোজ" data-language-autonym="বাংলা" data-language-local-name="Bangla" class="interlanguage-link-target"><span>বাংলা</span></a></li><li class="interlanguage-link interwiki-zh-min-nan mw-list-item"><a href="https://zh-min-nan.wikipedia.org/wiki/Ph%C3%BB-t%C3%B4-thn%CC%82g" title="Phû-tô-thn̂g – Minnan" lang="nan" hreflang="nan" data-title="Phû-tô-thn̂g" data-language-autonym="閩南語 / Bân-lâm-gú" data-language-local-name="Minnan" class="interlanguage-link-target"><span>閩南語 / Bân-lâm-gú</span></a></li><li class="interlanguage-link interwiki-be mw-list-item"><a href="https://be.wikipedia.org/wiki/%D0%93%D0%BB%D1%8E%D0%BA%D0%BE%D0%B7%D0%B0" title="Глюкоза – Belarusian" lang="be" hreflang="be" data-title="Глюкоза" data-language-autonym="Беларуская" data-language-local-name="Belarusian" class="interlanguage-link-target"><span>Беларуская</span></a></li><li class="interlanguage-link interwiki-be-x-old mw-list-item"><a href="https://be-tarask.wikipedia.org/wiki/%D0%93%D0%BB%D1%8E%D0%BA%D0%BE%D0%B7%D0%B0" title="Глюкоза – Belarusian (Taraškievica orthography)" lang="be-tarask" hreflang="be-tarask" data-title="Глюкоза" data-language-autonym="Беларуская (тарашкевіца)" data-language-local-name="Belarusian (Taraškievica orthography)" class="interlanguage-link-target"><span>Беларуская (тарашкевіца)</span></a></li><li class="interlanguage-link interwiki-bcl mw-list-item"><a href="https://bcl.wikipedia.org/wiki/Glukosa" title="Glukosa – Central Bikol" lang="bcl" hreflang="bcl" data-title="Glukosa" data-language-autonym="Bikol Central" data-language-local-name="Central Bikol" class="interlanguage-link-target"><span>Bikol Central</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%93%D0%BB%D1%8E%D0%BA%D0%BE%D0%B7%D0%B0" title="Глюкоза – Bulgarian" lang="bg" hreflang="bg" data-title="Глюкоза" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target"><span>Български</span></a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Glukoza" title="Glukoza – Bosnian" lang="bs" hreflang="bs" data-title="Glukoza" data-language-autonym="Bosanski" data-language-local-name="Bosnian" class="interlanguage-link-target"><span>Bosanski</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Glucosa" title="Glucosa – Catalan" lang="ca" hreflang="ca" data-title="Glucosa" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Gluk%C3%B3za" title="Glukóza – Czech" lang="cs" hreflang="cs" data-title="Glukóza" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-co mw-list-item"><a href="https://co.wikipedia.org/wiki/Glucosiu" title="Glucosiu – Corsican" lang="co" hreflang="co" data-title="Glucosiu" data-language-autonym="Corsu" data-language-local-name="Corsican" class="interlanguage-link-target"><span>Corsu</span></a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Glukose" title="Glukose – Danish" lang="da" hreflang="da" data-title="Glukose" data-language-autonym="Dansk" data-language-local-name="Danish" class="interlanguage-link-target"><span>Dansk</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Glucose" title="Glucose – German" lang="de" hreflang="de" data-title="Glucose" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/Gl%C3%BCkoos" title="Glükoos – Estonian" lang="et" hreflang="et" data-title="Glükoos" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%93%CE%BB%CF%85%CE%BA%CF%8C%CE%B6%CE%B7" title="Γλυκόζη – Greek" lang="el" hreflang="el" data-title="Γλυκόζη" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target"><span>Ελληνικά</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Glucosa" title="Glucosa – Spanish" lang="es" hreflang="es" data-title="Glucosa" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eo mw-list-item"><a href="https://eo.wikipedia.org/wiki/Glukozo" title="Glukozo – Esperanto" lang="eo" hreflang="eo" data-title="Glukozo" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Glukosa" title="Glukosa – Basque" lang="eu" hreflang="eu" data-title="Glukosa" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%DA%AF%D9%84%D9%88%DA%A9%D8%B2" title="گلوکز – Persian" lang="fa" hreflang="fa" data-title="گلوکز" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Glucose" title="Glucose – French" lang="fr" hreflang="fr" data-title="Glucose" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-fy mw-list-item"><a href="https://fy.wikipedia.org/wiki/Druves%C3%BBker" title="Druvesûker – Western Frisian" lang="fy" hreflang="fy" data-title="Druvesûker" data-language-autonym="Frysk" data-language-local-name="Western Frisian" class="interlanguage-link-target"><span>Frysk</span></a></li><li class="interlanguage-link interwiki-ga mw-list-item"><a href="https://ga.wikipedia.org/wiki/Gl%C3%BAc%C3%B3s" title="Glúcós – Irish" lang="ga" hreflang="ga" data-title="Glúcós" data-language-autonym="Gaeilge" data-language-local-name="Irish" class="interlanguage-link-target"><span>Gaeilge</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Glicosa" title="Glicosa – Galician" lang="gl" hreflang="gl" data-title="Glicosa" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EA%B8%80%EB%A3%A8%EC%BD%94%EC%8A%A4" title="글루코스 – Korean" lang="ko" hreflang="ko" data-title="글루코스" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D4%B3%D5%AC%D5%B5%D5%B8%D6%82%D5%AF%D5%B8%D5%A6" title="Գլյուկոզ – Armenian" lang="hy" hreflang="hy" data-title="Գլյուկոզ" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-hi mw-list-item"><a href="https://hi.wikipedia.org/wiki/%E0%A4%97%E0%A5%8D%E0%A4%B2%E0%A5%82%E0%A4%95%E0%A5%8B%E0%A4%9C%E0%A4%BC" title="ग्लूकोज़ – Hindi" lang="hi" hreflang="hi" data-title="ग्लूकोज़" data-language-autonym="हिन्दी" data-language-local-name="Hindi" class="interlanguage-link-target"><span>हिन्दी</span></a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Glukoza" title="Glukoza – Croatian" lang="hr" hreflang="hr" data-title="Glukoza" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-io mw-list-item"><a href="https://io.wikipedia.org/wiki/Glikoso" title="Glikoso – Ido" lang="io" hreflang="io" data-title="Glikoso" data-language-autonym="Ido" data-language-local-name="Ido" class="interlanguage-link-target"><span>Ido</span></a></li><li class="interlanguage-link interwiki-ig mw-list-item"><a href="https://ig.wikipedia.org/wiki/Glucose" title="Glucose – Igbo" lang="ig" hreflang="ig" data-title="Glucose" data-language-autonym="Igbo" data-language-local-name="Igbo" class="interlanguage-link-target"><span>Igbo</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Glukosa" title="Glukosa – Indonesian" lang="id" hreflang="id" data-title="Glukosa" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target"><span>Bahasa Indonesia</span></a></li><li class="interlanguage-link interwiki-ia mw-list-item"><a href="https://ia.wikipedia.org/wiki/Glucosa" title="Glucosa – Interlingua" lang="ia" hreflang="ia" data-title="Glucosa" data-language-autonym="Interlingua" data-language-local-name="Interlingua" class="interlanguage-link-target"><span>Interlingua</span></a></li><li class="interlanguage-link interwiki-zu mw-list-item"><a href="https://zu.wikipedia.org/wiki/I-glucose" title="I-glucose – Zulu" lang="zu" hreflang="zu" data-title="I-glucose" data-language-autonym="IsiZulu" data-language-local-name="Zulu" class="interlanguage-link-target"><span>IsiZulu</span></a></li><li class="interlanguage-link interwiki-is mw-list-item"><a href="https://is.wikipedia.org/wiki/Gl%C3%BAk%C3%B3si" title="Glúkósi – Icelandic" lang="is" hreflang="is" data-title="Glúkósi" data-language-autonym="Íslenska" data-language-local-name="Icelandic" class="interlanguage-link-target"><span>Íslenska</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Glucosio" title="Glucosio – Italian" lang="it" hreflang="it" data-title="Glucosio" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%92%D7%9C%D7%95%D7%A7%D7%95%D7%96" title="גלוקוז – Hebrew" lang="he" hreflang="he" data-title="גלוקוז" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-jv mw-list-item"><a href="https://jv.wikipedia.org/wiki/Glukosa" title="Glukosa – Javanese" lang="jv" hreflang="jv" data-title="Glukosa" data-language-autonym="Jawa" data-language-local-name="Javanese" class="interlanguage-link-target"><span>Jawa</span></a></li><li class="interlanguage-link interwiki-kn mw-list-item"><a href="https://kn.wikipedia.org/wiki/%E0%B2%97%E0%B3%8D%E0%B2%B2%E0%B3%81%E0%B2%95%E0%B3%8B%E0%B2%B8%E0%B3%8D" title="ಗ್ಲುಕೋಸ್ – Kannada" lang="kn" hreflang="kn" data-title="ಗ್ಲುಕೋಸ್" data-language-autonym="ಕನ್ನಡ" data-language-local-name="Kannada" class="interlanguage-link-target"><span>ಕನ್ನಡ</span></a></li><li class="interlanguage-link interwiki-pam mw-list-item"><a href="https://pam.wikipedia.org/wiki/Glucose" title="Glucose – Pampanga" lang="pam" hreflang="pam" data-title="Glucose" data-language-autonym="Kapampangan" data-language-local-name="Pampanga" class="interlanguage-link-target"><span>Kapampangan</span></a></li><li class="interlanguage-link interwiki-ka mw-list-item"><a href="https://ka.wikipedia.org/wiki/%E1%83%92%E1%83%9A%E1%83%A3%E1%83%99%E1%83%9D%E1%83%96%E1%83%90" title="გლუკოზა – Georgian" lang="ka" hreflang="ka" data-title="გლუკოზა" data-language-autonym="ქართული" data-language-local-name="Georgian" class="interlanguage-link-target"><span>ქართული</span></a></li><li class="interlanguage-link interwiki-ks mw-list-item"><a href="https://ks.wikipedia.org/wiki/%DA%AF%D9%8F%D9%84%DB%81%D9%90_%DA%A9%D9%88%D8%B2" title="گُلہِ کوز – Kashmiri" lang="ks" hreflang="ks" data-title="گُلہِ کوز" data-language-autonym="कॉशुर / کٲشُر" data-language-local-name="Kashmiri" class="interlanguage-link-target"><span>कॉशुर / کٲشُر</span></a></li><li class="interlanguage-link interwiki-kk mw-list-item"><a href="https://kk.wikipedia.org/wiki/%D0%93%D0%BB%D1%8E%D0%BA%D0%BE%D0%B7%D0%B0" title="Глюкоза – Kazakh" lang="kk" hreflang="kk" data-title="Глюкоза" data-language-autonym="Қазақша" data-language-local-name="Kazakh" class="interlanguage-link-target"><span>Қазақша</span></a></li><li class="interlanguage-link interwiki-sw mw-list-item"><a href="https://sw.wikipedia.org/wiki/Glukosi" title="Glukosi – Swahili" lang="sw" hreflang="sw" data-title="Glukosi" data-language-autonym="Kiswahili" data-language-local-name="Swahili" class="interlanguage-link-target"><span>Kiswahili</span></a></li><li class="interlanguage-link interwiki-ku mw-list-item"><a href="https://ku.wikipedia.org/wiki/Glukoz" title="Glukoz – Kurdish" lang="ku" hreflang="ku" data-title="Glukoz" data-language-autonym="Kurdî" data-language-local-name="Kurdish" class="interlanguage-link-target"><span>Kurdî</span></a></li><li class="interlanguage-link interwiki-ky mw-list-item"><a href="https://ky.wikipedia.org/wiki/%D0%93%D0%BB%D1%8E%D0%BA%D0%BE%D0%B7%D0%B0" title="Глюкоза – Kyrgyz" lang="ky" hreflang="ky" data-title="Глюкоза" data-language-autonym="Кыргызча" data-language-local-name="Kyrgyz" class="interlanguage-link-target"><span>Кыргызча</span></a></li><li class="interlanguage-link interwiki-lo mw-list-item"><a href="https://lo.wikipedia.org/wiki/%E0%BA%99%E0%BB%89%E0%BA%B3%E0%BA%95%E0%BA%B2%E0%BA%99" title="ນ້ຳຕານ – Lao" lang="lo" hreflang="lo" data-title="ນ້ຳຕານ" data-language-autonym="ລາວ" data-language-local-name="Lao" class="interlanguage-link-target"><span>ລາວ</span></a></li><li class="interlanguage-link interwiki-la mw-list-item"><a href="https://la.wikipedia.org/wiki/Glucosum" title="Glucosum – Latin" lang="la" hreflang="la" data-title="Glucosum" data-language-autonym="Latina" data-language-local-name="Latin" class="interlanguage-link-target"><span>Latina</span></a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Glikoze" title="Glikoze – Latvian" lang="lv" hreflang="lv" data-title="Glikoze" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target"><span>Latviešu</span></a></li><li class="interlanguage-link interwiki-lt mw-list-item"><a href="https://lt.wikipedia.org/wiki/Gliukoz%C4%97" title="Gliukozė – Lithuanian" lang="lt" hreflang="lt" data-title="Gliukozė" data-language-autonym="Lietuvių" data-language-local-name="Lithuanian" class="interlanguage-link-target"><span>Lietuvių</span></a></li><li class="interlanguage-link interwiki-lmo mw-list-item"><a href="https://lmo.wikipedia.org/wiki/Glucosa" title="Glucosa – Lombard" lang="lmo" hreflang="lmo" data-title="Glucosa" data-language-autonym="Lombard" data-language-local-name="Lombard" class="interlanguage-link-target"><span>Lombard</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Gl%C3%BCk%C3%B3z" title="Glükóz – Hungarian" lang="hu" hreflang="hu" data-title="Glükóz" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%93%D0%BB%D0%B8%D0%BA%D0%BE%D0%B7%D0%B0" title="Гликоза – Macedonian" lang="mk" hreflang="mk" data-title="Гликоза" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-ml mw-list-item"><a href="https://ml.wikipedia.org/wiki/%E0%B4%97%E0%B5%8D%E0%B4%B2%E0%B5%82%E0%B4%95%E0%B5%8D%E0%B4%95%E0%B5%8B%E0%B4%B8%E0%B5%8D" title="ഗ്ലൂക്കോസ് – Malayalam" lang="ml" hreflang="ml" data-title="ഗ്ലൂക്കോസ്" data-language-autonym="മലയാളം" data-language-local-name="Malayalam" class="interlanguage-link-target"><span>മലയാളം</span></a></li><li class="interlanguage-link interwiki-mr mw-list-item"><a href="https://mr.wikipedia.org/wiki/%E0%A4%97%E0%A5%8D%E0%A4%B2%E0%A5%81%E0%A4%95%E0%A5%8B%E0%A4%9C" title="ग्लुकोज – Marathi" lang="mr" hreflang="mr" data-title="ग्लुकोज" data-language-autonym="मराठी" data-language-local-name="Marathi" class="interlanguage-link-target"><span>मराठी</span></a></li><li class="interlanguage-link interwiki-xmf mw-list-item"><a href="https://xmf.wikipedia.org/wiki/%E1%83%92%E1%83%9A%E1%83%A3%E1%83%99%E1%83%9D%E1%83%96%E1%83%90" title="გლუკოზა – Mingrelian" lang="xmf" hreflang="xmf" data-title="გლუკოზა" data-language-autonym="მარგალური" data-language-local-name="Mingrelian" class="interlanguage-link-target"><span>მარგალური</span></a></li><li class="interlanguage-link interwiki-arz mw-list-item"><a href="https://arz.wikipedia.org/wiki/%D8%AC%D9%84%D9%88%D9%83%D9%88%D8%B2" title="جلوكوز – Egyptian Arabic" lang="arz" hreflang="arz" data-title="جلوكوز" data-language-autonym="مصرى" data-language-local-name="Egyptian Arabic" class="interlanguage-link-target"><span>مصرى</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Glukosa" title="Glukosa – Malay" lang="ms" hreflang="ms" data-title="Glukosa" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" class="interlanguage-link-target"><span>Bahasa Melayu</span></a></li><li class="interlanguage-link interwiki-min mw-list-item"><a href="https://min.wikipedia.org/wiki/Glukosa" title="Glukosa – Minangkabau" lang="min" hreflang="min" data-title="Glukosa" data-language-autonym="Minangkabau" data-language-local-name="Minangkabau" class="interlanguage-link-target"><span>Minangkabau</span></a></li><li class="interlanguage-link interwiki-cdo mw-list-item"><a href="https://cdo.wikipedia.org/wiki/Bu%C3%B2-d%C3%B2%CC%A4-t%C3%B2ng" title="Buò-dò̤-tòng – Mindong" lang="cdo" hreflang="cdo" data-title="Buò-dò̤-tòng" data-language-autonym="閩東語 / Mìng-dĕ̤ng-ngṳ̄" data-language-local-name="Mindong" class="interlanguage-link-target"><span>閩東語 / Mìng-dĕ̤ng-ngṳ̄</span></a></li><li class="interlanguage-link interwiki-mn mw-list-item"><a href="https://mn.wikipedia.org/wiki/%D0%93%D0%BB%D1%8E%D0%BA%D0%BE%D0%B7" title="Глюкоз – Mongolian" lang="mn" hreflang="mn" data-title="Глюкоз" data-language-autonym="Монгол" data-language-local-name="Mongolian" class="interlanguage-link-target"><span>Монгол</span></a></li><li class="interlanguage-link interwiki-my mw-list-item"><a href="https://my.wikipedia.org/wiki/%E1%80%82%E1%80%9C%E1%80%B0%E1%80%B8%E1%80%80%E1%80%AD%E1%80%AF%E1%80%B7%E1%80%9E%E1%80%80%E1%80%BC%E1%80%AC%E1%80%B8" title="ဂလူးကို့သကြား – Burmese" lang="my" hreflang="my" data-title="ဂလူးကို့သကြား" data-language-autonym="မြန်မာဘာသာ" data-language-local-name="Burmese" class="interlanguage-link-target"><span>မြန်မာဘာသာ</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Glucose" title="Glucose – Dutch" lang="nl" hreflang="nl" data-title="Glucose" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%B0%E3%83%AB%E3%82%B3%E3%83%BC%E3%82%B9" title="グルコース – Japanese" lang="ja" hreflang="ja" data-title="グルコース" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-frr mw-list-item"><a href="https://frr.wikipedia.org/wiki/Glukoos" title="Glukoos – Northern Frisian" lang="frr" hreflang="frr" data-title="Glukoos" data-language-autonym="Nordfriisk" data-language-local-name="Northern Frisian" class="interlanguage-link-target"><span>Nordfriisk</span></a></li><li class="interlanguage-link interwiki-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Glukose" title="Glukose – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Glukose" data-language-autonym="Norsk bokmål" data-language-local-name="Norwegian Bokmål" class="interlanguage-link-target"><span>Norsk bokmål</span></a></li><li class="interlanguage-link interwiki-nn mw-list-item"><a href="https://nn.wikipedia.org/wiki/Glukose" title="Glukose – Norwegian Nynorsk" lang="nn" hreflang="nn" data-title="Glukose" data-language-autonym="Norsk nynorsk" data-language-local-name="Norwegian Nynorsk" class="interlanguage-link-target"><span>Norsk nynorsk</span></a></li><li class="interlanguage-link interwiki-oc mw-list-item"><a href="https://oc.wikipedia.org/wiki/Gluc%C3%B2sa" title="Glucòsa – Occitan" lang="oc" hreflang="oc" data-title="Glucòsa" data-language-autonym="Occitan" data-language-local-name="Occitan" class="interlanguage-link-target"><span>Occitan</span></a></li><li class="interlanguage-link interwiki-om mw-list-item"><a href="https://om.wikipedia.org/wiki/Giluukoosii" title="Giluukoosii – Oromo" lang="om" hreflang="om" data-title="Giluukoosii" data-language-autonym="Oromoo" data-language-local-name="Oromo" class="interlanguage-link-target"><span>Oromoo</span></a></li><li class="interlanguage-link interwiki-uz mw-list-item"><a href="https://uz.wikipedia.org/wiki/Glukoza" title="Glukoza – Uzbek" lang="uz" hreflang="uz" data-title="Glukoza" data-language-autonym="Oʻzbekcha / ўзбекча" data-language-local-name="Uzbek" class="interlanguage-link-target"><span>Oʻzbekcha / ўзбекча</span></a></li><li class="interlanguage-link interwiki-pa mw-list-item"><a href="https://pa.wikipedia.org/wiki/%E0%A8%97%E0%A9%81%E0%A8%B2%E0%A9%82%E0%A8%95%E0%A9%8B%E0%A8%B8" title="ਗੁਲੂਕੋਸ – Punjabi" lang="pa" hreflang="pa" data-title="ਗੁਲੂਕੋਸ" data-language-autonym="ਪੰਜਾਬੀ" data-language-local-name="Punjabi" class="interlanguage-link-target"><span>ਪੰਜਾਬੀ</span></a></li><li class="interlanguage-link interwiki-pnb mw-list-item"><a href="https://pnb.wikipedia.org/wiki/%DA%AF%D9%84%D9%88%DA%A9%D9%88%D8%B2" title="گلوکوز – Western Punjabi" lang="pnb" hreflang="pnb" data-title="گلوکوز" data-language-autonym="پنجابی" data-language-local-name="Western Punjabi" class="interlanguage-link-target"><span>پنجابی</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Glukoza" title="Glukoza – Polish" lang="pl" hreflang="pl" data-title="Glukoza" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Glicose" title="Glicose – Portuguese" lang="pt" hreflang="pt" data-title="Glicose" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Glucoz%C4%83" title="Glucoză – Romanian" lang="ro" hreflang="ro" data-title="Glucoză" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-qu mw-list-item"><a href="https://qu.wikipedia.org/wiki/Uwas_misk%27i" title="Uwas misk&#039;i – Quechua" lang="qu" hreflang="qu" data-title="Uwas misk&#039;i" data-language-autonym="Runa Simi" data-language-local-name="Quechua" class="interlanguage-link-target"><span>Runa Simi</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%93%D0%BB%D1%8E%D0%BA%D0%BE%D0%B7%D0%B0" title="Глюкоза – Russian" lang="ru" hreflang="ru" data-title="Глюкоза" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sq mw-list-item"><a href="https://sq.wikipedia.org/wiki/Glukoza" title="Glukoza – Albanian" lang="sq" hreflang="sq" data-title="Glukoza" data-language-autonym="Shqip" data-language-local-name="Albanian" class="interlanguage-link-target"><span>Shqip</span></a></li><li class="interlanguage-link interwiki-si mw-list-item"><a href="https://si.wikipedia.org/wiki/%E0%B6%9C%E0%B7%8A%E0%B6%BD%E0%B7%96%E0%B6%9A%E0%B7%9D%E0%B7%83%E0%B7%8A" title="ග්ලූකෝස් – Sinhala" lang="si" hreflang="si" data-title="ග්ලූකෝස්" data-language-autonym="සිංහල" data-language-local-name="Sinhala" class="interlanguage-link-target"><span>සිංහල</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Glucose" title="Glucose – Simple English" lang="en-simple" hreflang="en-simple" data-title="Glucose" data-language-autonym="Simple English" data-language-local-name="Simple English" class="interlanguage-link-target"><span>Simple English</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Gluk%C3%B3za" title="Glukóza – Slovak" lang="sk" hreflang="sk" data-title="Glukóza" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Glukoza" title="Glukoza – Slovenian" lang="sl" hreflang="sl" data-title="Glukoza" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-ckb mw-list-item"><a href="https://ckb.wikipedia.org/wiki/%DA%AF%D9%84%D9%88%D9%88%DA%A9%DB%86%D8%B2" title="گلووکۆز – Central Kurdish" lang="ckb" hreflang="ckb" data-title="گلووکۆز" data-language-autonym="کوردی" data-language-local-name="Central Kurdish" class="interlanguage-link-target"><span>کوردی</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/%D0%93%D0%BB%D1%83%D0%BA%D0%BE%D0%B7%D0%B0" title="Глукоза – Serbian" lang="sr" hreflang="sr" data-title="Глукоза" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Glukoza" title="Glukoza – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Glukoza" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-su badge-Q17437796 badge-featuredarticle mw-list-item" title="featured article badge"><a href="https://su.wikipedia.org/wiki/Glukosa" title="Glukosa – Sundanese" lang="su" hreflang="su" data-title="Glukosa" data-language-autonym="Sunda" data-language-local-name="Sundanese" class="interlanguage-link-target"><span>Sunda</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Glukoosi" title="Glukoosi – Finnish" lang="fi" hreflang="fi" data-title="Glukoosi" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Glukos" title="Glukos – Swedish" lang="sv" hreflang="sv" data-title="Glukos" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-tl mw-list-item"><a href="https://tl.wikipedia.org/wiki/Glukosa" title="Glukosa – Tagalog" lang="tl" hreflang="tl" data-title="Glukosa" data-language-autonym="Tagalog" data-language-local-name="Tagalog" class="interlanguage-link-target"><span>Tagalog</span></a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%95%E0%AF%81%E0%AE%B3%E0%AF%81%E0%AE%95%E0%AF%8D%E0%AE%95%E0%AF%8B%E0%AE%9A%E0%AF%81" title="குளுக்கோசு – Tamil" lang="ta" hreflang="ta" data-title="குளுக்கோசு" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-tt mw-list-item"><a href="https://tt.wikipedia.org/wiki/%D0%93%D0%BB%D1%8E%D0%BA%D0%BE%D0%B7%D0%B0" title="Глюкоза – Tatar" lang="tt" hreflang="tt" data-title="Глюкоза" data-language-autonym="Татарча / tatarça" data-language-local-name="Tatar" class="interlanguage-link-target"><span>Татарча / tatarça</span></a></li><li class="interlanguage-link interwiki-te mw-list-item"><a href="https://te.wikipedia.org/wiki/%E0%B0%97%E0%B1%8D%E0%B0%B2%E0%B1%82%E0%B0%95%E0%B1%8B%E0%B0%B8%E0%B1%8D" title="గ్లూకోస్ – Telugu" lang="te" hreflang="te" data-title="గ్లూకోస్" data-language-autonym="తెలుగు" data-language-local-name="Telugu" class="interlanguage-link-target"><span>తెలుగు</span></a></li><li class="interlanguage-link interwiki-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B8%81%E0%B8%A5%E0%B8%B9%E0%B9%82%E0%B8%84%E0%B8%AA" title="กลูโคส – Thai" lang="th" hreflang="th" data-title="กลูโคส" data-language-autonym="ไทย" data-language-local-name="Thai" class="interlanguage-link-target"><span>ไทย</span></a></li><li class="interlanguage-link interwiki-tg mw-list-item"><a href="https://tg.wikipedia.org/wiki/%D0%93%D0%BB%D1%8E%D0%BA%D0%BE%D0%B7%D0%B0" title="Глюкоза – Tajik" lang="tg" hreflang="tg" data-title="Глюкоза" data-language-autonym="Тоҷикӣ" data-language-local-name="Tajik" class="interlanguage-link-target"><span>Тоҷикӣ</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Glukoz" title="Glukoz – Turkish" lang="tr" hreflang="tr" data-title="Glukoz" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%93%D0%BB%D1%8E%D0%BA%D0%BE%D0%B7%D0%B0" title="Глюкоза – Ukrainian" lang="uk" hreflang="uk" data-title="Глюкоза" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-ur mw-list-item"><a href="https://ur.wikipedia.org/wiki/%DA%AF%D9%84%D9%88%DA%A9%D9%88%D8%B2" title="گلوکوز – Urdu" lang="ur" hreflang="ur" data-title="گلوکوز" data-language-autonym="اردو" data-language-local-name="Urdu" class="interlanguage-link-target"><span>اردو</span></a></li><li class="interlanguage-link interwiki-ug mw-list-item"><a href="https://ug.wikipedia.org/wiki/%DA%AF%D9%84%DB%87%D9%83%D9%88%D8%B2%D8%A7" title="گلۇكوزا – Uyghur" lang="ug" hreflang="ug" data-title="گلۇكوزا" data-language-autonym="ئۇيغۇرچە / Uyghurche" data-language-local-name="Uyghur" class="interlanguage-link-target"><span>ئۇيغۇرچە / Uyghurche</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Glucose" title="Glucose – Vietnamese" lang="vi" hreflang="vi" data-title="Glucose" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target"><span>Tiếng Việt</span></a></li><li class="interlanguage-link interwiki-war mw-list-item"><a href="https://war.wikipedia.org/wiki/Glukosa" title="Glukosa – Waray" lang="war" hreflang="war" data-title="Glukosa" data-language-autonym="Winaray" data-language-local-name="Waray" class="interlanguage-link-target"><span>Winaray</span></a></li><li class="interlanguage-link interwiki-wuu mw-list-item"><a href="https://wuu.wikipedia.org/wiki/%E8%91%A1%E8%90%84%E7%B3%96" title="葡萄糖 – Wu" lang="wuu" hreflang="wuu" data-title="葡萄糖" data-language-autonym="吴语" data-language-local-name="Wu" class="interlanguage-link-target"><span>吴语</span></a></li><li class="interlanguage-link interwiki-zh-yue mw-list-item"><a href="https://zh-yue.wikipedia.org/wiki/%E8%91%A1%E8%90%84%E9%86%A3" title="葡萄醣 – Cantonese" lang="yue" hreflang="yue" data-title="葡萄醣" data-language-autonym="粵語" data-language-local-name="Cantonese" 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It allows adding a reason in the summary.">undo</a></span></strong></div><div id="mw-diff-ntitle2"><a href="/wiki/User:Synpath" class="mw-userlink" title="User:Synpath" data-mw-revid="1258840145"><bdi>Synpath</bdi></a> <span class="mw-usertoollinks">(<a href="/wiki/User_talk:Synpath" class="mw-usertoollinks-talk" title="User talk:Synpath">talk</a> | <a href="/wiki/Special:Contributions/Synpath" class="mw-usertoollinks-contribs" title="Special:Contributions/Synpath">contribs</a>)</span><div class="mw-diff-usermetadata"><div class="mw-diff-userroles"><a href="/wiki/Wikipedia:Extended_confirmed_editors" class="mw-redirect" title="Wikipedia:Extended confirmed editors">Extended confirmed users</a></div><div class="mw-diff-usereditcount"><span>992</span> edits</div></div></div><div id="mw-diff-ntitle3"> <span class="comment comment--without-parentheses"><span class="autocomment"><a href="#Structure_and_nomenclature">→<bdi dir="ltr">Structure and nomenclature</bdi></a>: </span> Mutarotation discussed in another section</span></div><div id="mw-diff-ntitle5"><span class="mw-tag-markers"><a href="/wiki/Special:Tags" title="Special:Tags">Tag</a>: <span class="mw-tag-marker mw-tag-marker-visualeditor-wikitext"><a href="https://www.mediawiki.org/wiki/Special:MyLanguage/2017_wikitext_editor" class="extiw" title="mw:Special:MyLanguage/2017 wikitext editor">2017 wikitext editor</a></span></span></div><div id="mw-diff-ntitle4"><a href="/w/index.php?title=Glucose&amp;diff=next&amp;oldid=1258840145" title="Glucose" id="differences-nextlink">Next edit →</a></div></td> </tr><tr> <td colspan="2" class="diff-lineno">Line 161:</td> <td colspan="2" class="diff-lineno">Line 161:</td> </tr> <tr> <td class="diff-marker"></td> <td class="diff-context diff-side-deleted"><br /></td> <td class="diff-marker"></td> <td class="diff-context diff-side-added"><br /></td> </tr> <tr> <td class="diff-marker"></td> <td class="diff-context diff-side-deleted"><div>===Structure and nomenclature===</div></td> <td class="diff-marker"></td> <td class="diff-context diff-side-added"><div>===Structure and nomenclature===</div></td> </tr> <tr> <td class="diff-marker" data-marker="−"></td> <td class="diff-deletedline diff-side-deleted"><div>{{See also|Mutarotation}}</div></td> <td colspan="2" class="diff-empty diff-side-added"></td> </tr> <tr> <td class="diff-marker" data-marker="−"></td> <td class="diff-deletedline diff-side-deleted"><div>[[File:Mutarotation D-Glucose V.1.png|thumb|center|Mutarotation of glucose]]</div></td> <td colspan="2" class="diff-empty diff-side-added"></td> </tr> <tr> <td class="diff-marker" data-marker="−"></td> <td class="diff-deletedline diff-side-deleted"><br /></td> <td colspan="2" class="diff-empty diff-side-added"></td> </tr> <tr> <td class="diff-marker"></td> <td class="diff-context diff-side-deleted"><div>Glucose is present in solid form as a [[monohydrate]] with a closed [[pyran]] ring (α-glucopyranose monohydrate, sometimes known less precisely by dextrose hydrate). In aqueous solution, on the other hand, it is an open-chain to a small extent and is present predominantly as α- or β-[[pyranose]], which interconvert. From aqueous solutions, the three known forms can be crystallized: α-glucopyranose, β-glucopyranose and α-glucopyranose monohydrate.&lt;ref name="Ullmann"&gt;{{Cite book |doi=10.1002/14356007.a12_457.pub2 |chapter=Glucose and Glucose-Containing Syrups |title=Ullmann's Encyclopedia of Industrial Chemistry |year=2006 |last1=Schenck |first1=Fred W. |isbn=978-3-527-30673-2}}&lt;/ref&gt; Glucose is a building block of the disaccharides lactose and sucrose (cane or beet sugar), of [[oligosaccharide]]s such as [[raffinose]] and of [[polysaccharide]]s such as [[starch]], [[amylopectin]], [[glycogen]], and [[cellulose]].&lt;ref name="r2"/&gt;&lt;ref name="pf"/&gt; The [[glass transition temperature]] of glucose is {{cvt|31|C}} and the Gordon–Taylor constant (an experimentally determined constant for the prediction of the glass transition temperature for different mass fractions of a mixture of two substances)&lt;ref name="pf"&gt;Patrick F. Fox: ''Advanced Dairy Chemistry Volume 3: Lactose, water, salts and vitamins'', Springer, 1992. Volume 3, {{ISBN|9780412630200}}. p. 316.&lt;/ref&gt; is 4.5.&lt;ref name="Caballero 1 76"&gt;Benjamin Caballero, Paul Finglas, Fidel Toldrá: ''Encyclopedia of Food and Health''. Academic Press (2016). {{ISBN|9780123849533}}, Volume 1, p. 76.&lt;/ref&gt;</div></td> <td class="diff-marker"></td> <td class="diff-context diff-side-added"><div>Glucose is present in solid form as a [[monohydrate]] with a closed [[pyran]] ring (α-glucopyranose monohydrate, sometimes known less precisely by dextrose hydrate). In aqueous solution, on the other hand, it is an open-chain to a small extent and is present predominantly as α- or β-[[pyranose]], which interconvert. From aqueous solutions, the three known forms can be crystallized: α-glucopyranose, β-glucopyranose and α-glucopyranose monohydrate.&lt;ref name="Ullmann"&gt;{{Cite book |doi=10.1002/14356007.a12_457.pub2 |chapter=Glucose and Glucose-Containing Syrups |title=Ullmann's Encyclopedia of Industrial Chemistry |year=2006 |last1=Schenck |first1=Fred W. |isbn=978-3-527-30673-2}}&lt;/ref&gt; Glucose is a building block of the disaccharides lactose and sucrose (cane or beet sugar), of [[oligosaccharide]]s such as [[raffinose]] and of [[polysaccharide]]s such as [[starch]], [[amylopectin]], [[glycogen]], and [[cellulose]].&lt;ref name="r2"/&gt;&lt;ref name="pf"/&gt; The [[glass transition temperature]] of glucose is {{cvt|31|C}} and the Gordon–Taylor constant (an experimentally determined constant for the prediction of the glass transition temperature for different mass fractions of a mixture of two substances)&lt;ref name="pf"&gt;Patrick F. Fox: ''Advanced Dairy Chemistry Volume 3: Lactose, water, salts and vitamins'', Springer, 1992. Volume 3, {{ISBN|9780412630200}}. p. 316.&lt;/ref&gt; is 4.5.&lt;ref name="Caballero 1 76"&gt;Benjamin Caballero, Paul Finglas, Fidel Toldrá: ''Encyclopedia of Food and Health''. Academic Press (2016). {{ISBN|9780123849533}}, Volume 1, p. 76.&lt;/ref&gt;</div></td> </tr> <tr> <td class="diff-marker"></td> <td class="diff-context diff-side-deleted"><br /></td> <td class="diff-marker"></td> <td class="diff-context diff-side-added"><br /></td> </tr> </table><hr class='diff-hr' id='mw-oldid' /> <h2 class='diff-currentversion-title'>Revision as of 22:38, 21 November 2024</h2> <div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Naturally produced monosaccharide</div> <p> <style data-mw-deduplicate="TemplateStyles:r1084375498">.mw-parser-output .ib-chembox{border-collapse:collapse;text-align:left}.mw-parser-output .ib-chembox td,.mw-parser-output .ib-chembox th{border:1px solid #a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}</style> </p> <table class="infobox ib-chembox"> <caption><style data-mw-deduplicate="TemplateStyles:r920966791">.mw-parser-output span.smallcaps{font-variant:small-caps}.mw-parser-output span.smallcaps-smaller{font-size:85%}</style><span class="smallcaps">d</span>-Glucose </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:D-glucose-chain-2D-skeletal.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/5e/D-glucose-chain-2D-skeletal.png/220px-D-glucose-chain-2D-skeletal.png" decoding="async" width="220" height="106" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/5e/D-glucose-chain-2D-skeletal.png/330px-D-glucose-chain-2D-skeletal.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/5e/D-glucose-chain-2D-skeletal.png/440px-D-glucose-chain-2D-skeletal.png 2x" data-file-width="1100" data-file-height="530" /></a></span><br /><div style="text-align:center;"><a href="/wiki/Skeletal_formula" title="Skeletal formula">Skeletal formula</a> of <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-glucose</div> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:Alpha-D-Glucopyranose.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c6/Alpha-D-Glucopyranose.svg/120px-Alpha-D-Glucopyranose.svg.png" decoding="async" width="120" height="130" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c6/Alpha-D-Glucopyranose.svg/180px-Alpha-D-Glucopyranose.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c6/Alpha-D-Glucopyranose.svg/240px-Alpha-D-Glucopyranose.svg.png 2x" data-file-width="157" data-file-height="170" /></a></span><br /><div style="text-align:center;"><a href="/wiki/Haworth_projection" title="Haworth projection">Haworth projection</a> of α-<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-glucopyranose</div> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:D-glucose_chain_(Fischer).svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d9/D-glucose_chain_%28Fischer%29.svg/100px-D-glucose_chain_%28Fischer%29.svg.png" decoding="async" width="100" height="172" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d9/D-glucose_chain_%28Fischer%29.svg/150px-D-glucose_chain_%28Fischer%29.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d9/D-glucose_chain_%28Fischer%29.svg/200px-D-glucose_chain_%28Fischer%29.svg.png 2x" data-file-width="184" data-file-height="316" /></a></span><br /><div style="text-align:center;"><a href="/wiki/Fischer_projection" title="Fischer projection">Fischer projection</a> of <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-glucose</div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Names </th></tr> <tr> <td>Pronunciation </td> <td><span class="rt-commentedText nowrap"><span class="IPA nopopups noexcerpt" lang="en-fonipa"><a href="/wiki/Help:IPA/English" title="Help:IPA/English">/<span style="border-bottom:1px dotted"><span title="/ˈ/: primary stress follows">ˈ</span><span title="/ɡ/: &#39;g&#39; in &#39;guy&#39;">ɡ</span><span title="&#39;l&#39; in &#39;lie&#39;">l</span><span title="/uː/: &#39;oo&#39; in &#39;goose&#39;">uː</span><span title="&#39;k&#39; in &#39;kind&#39;">k</span><span title="/oʊ/: &#39;o&#39; in &#39;code&#39;">oʊ</span><span title="&#39;z&#39; in &#39;zoom&#39;">z</span></span>/</a></span></span>, <span class="rt-commentedText nowrap"><span class="IPA nopopups noexcerpt" lang="en-fonipa"><a href="/wiki/Help:IPA/English" title="Help:IPA/English">/<span style="border-bottom:1px dotted"><span title="/ɡ/: &#39;g&#39; in &#39;guy&#39;">ɡ</span><span title="&#39;l&#39; in &#39;lie&#39;">l</span><span title="/uː/: &#39;oo&#39; in &#39;goose&#39;">uː</span><span title="&#39;k&#39; in &#39;kind&#39;">k</span><span title="/oʊ/: &#39;o&#39; in &#39;code&#39;">oʊ</span><span title="&#39;s&#39; in &#39;sigh&#39;">s</span></span>/</a></span></span> </td></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Chemical_nomenclature" title="Chemical nomenclature">IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">Allowed trivial names:<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">&#91;</span>1<span class="cite-bracket">&#93;</span></a></sup> <ul><li>ᴅ-Glucose</li> <li>ᴅ-<i>gluco</i>-Hexose</li></ul></div> </td></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Preferred_IUPAC_name" title="Preferred IUPAC name">Preferred IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;">PINs are not identified for natural products.</div></div> </td></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Chemical_nomenclature#Systematic_name" title="Chemical nomenclature">Systematic IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;"><div style="clear:both;" class=""></div> <ul><li>(2<i>R</i>,3<i>S</i>,4<i>R</i>,5<i>R</i>)-2,3,4,5,6-Pentahydroxyhexanal <small><b>(linear form)</b></small></li> <li>(3<i>R</i>,4<i>S</i>,5<i>S</i>,6<i>R</i>)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol <small><b>(cyclic form)</b></small></li></ul></div></div> </td></tr> <tr> <td colspan="2" style="text-align:left;">Other names <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">Blood sugars<br />Dextrose<br />Corn sugar<br /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-Glucose<br />Grape sugar</div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=50-99-7">50-99-7</a></span><sup>&#160;<span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=492-62-6">492-62-6</a></span>&#x20;(α-<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-glucopyranose)<sup>&#160;<span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>α-<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-glucopyranose:&#x20;<span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=C%28%5BC%40%40H%5D1%5BC%40H%5D%28%5BC%40%40H%5D%28%5BC%40H%5D%28%5BC%40H%5D%28O1%29O%29O%29O%29O%29O">Interactive image</a></span></li><li>β-<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-glucopyranose:&#x20;<span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=OC%5BC%40H%5D1OC%28O%29%5BC%40H%5D%28O%29%5BC%40%40H%5D%28O%29%5BC%40%40H%5D1O">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td>3DMet </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.3dmet.dna.affrc.go.jp"><a rel="nofollow" class="external text" href="http://www.3dmet.dna.affrc.go.jp/cgi/show_data.php?acc=B01203">B01203</a></span></li></ul></div> </td></tr> <tr> <td>Abbreviations </td> <td>Glc </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Beilstein_database" title="Beilstein database">Beilstein Reference</a></div> </td> <td>1281604 </td></tr> <tr> <td><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=4167">CHEBI:4167</a></span><sup>&#160;<span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembldb/index.php/compound/inspect/ChEMBL1222250">ChEMBL1222250</a></span><sup>&#160;<span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.5589.html">5589</a></span><sup>&#160;<span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/European_Community_number" title="European Community number"><span title="European Community number (chemical identifier)">EC Number</span></a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>200-075-1</li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Gmelin_database" title="Gmelin database">Gmelin Reference</a></div> </td> <td>83256 </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/IUPHAR/BPS" class="mw-redirect" title="IUPHAR/BPS">IUPHAR/BPS</a></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.guidetopharmacology.org"><a rel="nofollow" class="external text" href="http://www.guidetopharmacology.org/GRAC/LigandDisplayForward?tab=summary&amp;ligandId=4536">4536</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/KEGG" title="KEGG">KEGG</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.kegg.jp"><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/C00031">C00031</a></span><sup>&#160;<span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/Medical_Subject_Headings" title="Medical Subject Headings">MeSH</a> </td> <td><span title="www.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://www.nlm.nih.gov/cgi/mesh/2014/MB_cgi?mode=&amp;term=Glucose">Glucose</a></span> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/5793">5793</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/RTECS" class="mw-redirect" title="RTECS">RTECS number</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>LZ6600000</li></ul></div> </td></tr> <tr> <td><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/5SL0G7R0OK">5SL0G7R0OK</a></span><sup>&#160;<span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/5J5I9EB41E">5J5I9EB41E</a></span>&#160;(α-<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-glucopyranose)<sup>&#160;<span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3-,4+,5-,6?/m1/s1<sup>&#160;<span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key:&#160;WQZGKKKJIJFFOK-GASJEMHNSA-N<sup>&#160;<span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div></div></li></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">α-<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-glucopyranose:&#x20;C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O)O)O)O)O</div></li><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">β-<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-glucopyranose:&#x20;OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td><span title="Carbon">C</span><sub>6</sub><span title="Hydrogen">H</span><sub>12</sub><span title="Oxygen">O</span><sub>6</sub> </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td><span class="nowrap"><span data-sort-value="7002180156000000000♠"></span>180.156</span>&#160;g/mol &#x20; </td></tr> <tr> <td>Appearance </td> <td>White powder </td></tr> <tr> <td><a href="/wiki/Density" title="Density">Density</a> </td> <td>1.54&#160;g/cm<sup>3</sup> </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>α-<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-Glucose:&#x20;146&#160;°C (295&#160;°F; 419&#160;K) β-<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-Glucose: 150&#160;°C (302&#160;°F; 423&#160;K) </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Aqueous_solution" title="Aqueous solution">Solubility in water</a></div> </td> <td>909&#160;g/L (25&#160;°C (77&#160;°F)) </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Magnetic_susceptibility" title="Magnetic susceptibility">Magnetic susceptibility</a> (&#967;)</div> </td> <td>−101.5×10<sup>−6</sup>&#160;cm<sup>3</sup>/mol </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Dipole#Molecular_dipoles" title="Dipole">Dipole moment</a></div> </td> <td>10.5674 </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Thermochemistry </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Heat_capacity" title="Heat capacity">Heat capacity</a> <span style="font-size:112%;">(<i>C</i>)</span></div> </td> <td>218.6&#160;J/(K·mol)<sup id="cite_ref-Boerio-Goates_1991_403–9_2-0" class="reference"><a href="#cite_note-Boerio-Goates_1991_403–9-2"><span class="cite-bracket">&#91;</span>2<span class="cite-bracket">&#93;</span></a></sup> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Standard_molar_entropy" title="Standard molar entropy">Std molar<br />entropy</a> <span style="font-size:112%;">(<i>S</i><sup>⦵</sup><sub>298</sub>)</span></div> </td> <td>209.2&#160;J/(K·mol)<sup id="cite_ref-Boerio-Goates_1991_403–9_2-1" class="reference"><a href="#cite_note-Boerio-Goates_1991_403–9-2"><span class="cite-bracket">&#91;</span>2<span class="cite-bracket">&#93;</span></a></sup> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Standard_enthalpy_change_of_formation" class="mw-redirect" title="Standard enthalpy change of formation">Std enthalpy of<br />formation</a> <span style="font-size:112%;">(Δ<sub>f</sub><i>H</i><sup>⦵</sup><sub>298</sub>)</span></div> </td> <td>−1271&#160;kJ/mol<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">&#91;</span>3<span class="cite-bracket">&#93;</span></a></sup> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Heat_of_combustion#Higher_heating_value" title="Heat of combustion">Heat of combustion, higher value</a> (HHV)</div> </td> <td>2,805&#160;kJ/mol (670&#160;kcal/mol) </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Pharmacology </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Anatomical_Therapeutic_Chemical_Classification_System" title="Anatomical Therapeutic Chemical Classification System">ATC code</a></div> </td> <td><a href="/wiki/ATC_code_B05" title="ATC code B05">B05CX01</a>&#x20;(<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=B05CX01">WHO</a></span>)&#x20;<a href="/wiki/ATC_code_V04" title="ATC code V04">V04CA02</a>&#x20;(<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=V04CA02">WHO</a></span>), <a href="/wiki/ATC_code_V06" title="ATC code V06">V06DC01</a>&#x20;(<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=V06DC01">WHO</a></span>) </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Hazards </th></tr> <tr> <td><a href="/wiki/NFPA_704" title="NFPA 704"><b>NFPA 704</b></a> (fire&#160;diamond) </td> <td><style data-mw-deduplicate="TemplateStyles:r1170367383">.mw-parser-output .nfpa-704-diamond-ref{float:right;padding:1px;text-align:right}.mw-parser-output .nfpa-704-diamond-container{width:82px;font-family:sans-serif;margin:0 auto}.mw-parser-output .nfpa-704-diamond-container-ref{float:left;margin-left:1em}.mw-parser-output .nfpa-704-diamond-images{float:left;font-size:20px;text-align:center;position:relative;height:80px;width:80px;padding:1px}.mw-parser-output .nfpa-704-diamond-map{position:absolute;height:80px;width:80px}.mw-parser-output .nfpa-704-diamond .noresize{margin:0 auto}.mw-parser-output .nfpa-704-diamond-code{line-height:1em;text-align:center;position:absolute}.mw-parser-output .nfpa-704-diamond-code>a{color:black}.mw-parser-output .nfpa-704-diamond-blue{width:13px;top:31px;left:15px}.mw-parser-output .nfpa-704-diamond-red{width:12px;top:12px;left:35px}.mw-parser-output .nfpa-704-diamond-yellow{width:13px;top:31px;left:54px}.mw-parser-output .nfpa-704-diamond-white-image{position:relative;top:51px;left:0}.mw-parser-output .nfpa-704-diamond-white-text{vertical-align:middle;text-align:center;line-height:80%;position:absolute;top:52px}.mw-parser-output .nfpa-704-diamond-white-text a>span{position:absolute;color:black}.mw-parser-output .nfpa-704-diamond-white-wors{font-size:15px;width:23px;left:29px}.mw-parser-output .nfpa-704-diamond-white-wox{font-size:15px;font-stretch:condensed;width:21px;line-height:80%;top:-4px;left:29px}.mw-parser-output .nfpa-704-diamond-white-abcp{font-size:13.5px;font-stretch:condensed;width:28px;left:26px}.mw-parser-output .nfpa-704-diamond-white-ac{font-size:10px;width:30px;left:25px}.mw-parser-output .nfpa-704-diamond-white-strike{text-decoration:line-through}</style><div class="nfpa-704-diamond notheme"><div class="nfpa-704-diamond-container"><div class="nfpa-704-diamond-images nounderlines"> <div class="nfpa-704-diamond-map"><figure class="noresize" typeof="mw:File"><span><img alt="NFPA 704 four-colored diamond" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/80px-NFPA_704.svg.png" decoding="async" width="80" height="80" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/120px-NFPA_704.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/160px-NFPA_704.svg.png 2x" data-file-width="512" data-file-height="512" usemap="#ImageMap_3d8171e88c0df7b6" /></span><map name="ImageMap_3d8171e88c0df7b6"><area href="/wiki/NFPA_704#Blue" shape="poly" coords="23,23,47,47,23,70,0,47" alt="Health 0: Exposure under fire conditions would offer no hazard beyond that of ordinary combustible material. E.g. sodium chloride" title="Health 0: Exposure under fire conditions would offer no hazard beyond that of ordinary combustible material. E.g. sodium chloride" /><area href="/wiki/NFPA_704#Red" shape="poly" coords="47,0,70,23,47,47,23,23" alt="Flammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oil" title="Flammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oil" /><area href="/wiki/NFPA_704#Yellow" shape="poly" coords="70,23,94,47,70,70,47,47" alt="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" title="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" /><area href="/wiki/NFPA_704#White" shape="poly" coords="47,47,70,70,47,94,23,70" alt="Special hazards (white): no code" title="Special hazards (white): no code" /></map><figcaption></figcaption></figure></div><div class="nfpa-704-diamond-code nfpa-704-diamond-blue"> <a href="/wiki/NFPA_704#Blue" title="NFPA 704"><span title="Health 0: Exposure under fire conditions would offer no hazard beyond that of ordinary combustible material. E.g. sodium chloride" class="notheme mw-no-invert">0</span></a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-red"> <a href="/wiki/NFPA_704#Red" title="NFPA 704"><span title="Flammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oil" class="notheme mw-no-invert">1</span></a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-yellow"> <a href="/wiki/NFPA_704#Yellow" title="NFPA 704"><span title="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" class="notheme mw-no-invert">0</span></a></div></div></div></div> </td></tr> <tr> <td><a href="/wiki/Safety_data_sheet" title="Safety data sheet">Safety data sheet</a> (SDS) </td> <td><a rel="nofollow" class="external text" href="http://www.inchem.org/documents/icsc/icsc/eics0865.htm">ICSC 08655</a> </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25&#160;°C [77&#160;°F], 100&#160;kPa).</div> <div style="margin-top: 0.3em;"><div style="text-align:center;"><span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/12px-Yes_check.svg.png" decoding="async" width="12" height="12" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/18px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/24px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span>&#160;<span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&amp;rev1=818842877&amp;page2=Glucose">verify</a></span>&#160;(<a href="/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validation" title="Wikipedia:WikiProject Chemicals/Chembox validation">what is</a>&#160;<sup><span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup>&#160;?) </div></div> <div style="margin-top: 0.3em; text-align: center;"><a href="/wiki/Wikipedia:Chemical_infobox#References" title="Wikipedia:Chemical infobox">Infobox references</a></div> </td></tr> </tbody></table><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound</div> <p><b>Glucose</b> is a <a href="/wiki/Sugar" title="Sugar">sugar</a> with the <a href="/wiki/Chemical_formula#Molecular_formula" title="Chemical formula">molecular formula</a> <style data-mw-deduplicate="TemplateStyles:r1123817410">.mw-parser-output .template-chem2-su{display:inline-block;font-size:80%;line-height:1;vertical-align:-0.35em}.mw-parser-output .template-chem2-su>span{display:block;text-align:left}.mw-parser-output sub.template-chem2-sub{font-size:80%;vertical-align:-0.35em}.mw-parser-output sup.template-chem2-sup{font-size:80%;vertical-align:0.65em}</style><span class="chemf nowrap"><a href="/wiki/Carbon" title="Carbon">C</a><sub class="template-chem2-sub">6</sub><a href="/wiki/Hydrogen" title="Hydrogen">H</a><sub class="template-chem2-sub">12</sub><a href="/wiki/Oxygen" title="Oxygen">O</a><sub class="template-chem2-sub">6</sub></span>. It is overall the most abundant <a href="/wiki/Monosaccharide" title="Monosaccharide">monosaccharide</a>,<sup id="cite_ref-DombKost1998_4-0" class="reference"><a href="#cite_note-DombKost1998-4"><span class="cite-bracket">&#91;</span>4<span class="cite-bracket">&#93;</span></a></sup> a subcategory of <a href="/wiki/Carbohydrate" title="Carbohydrate">carbohydrates</a>. It is mainly made by <a href="/wiki/Plants" class="mw-redirect" title="Plants">plants</a> and most <a href="/wiki/Algae" title="Algae">algae</a> during <a href="/wiki/Photosynthesis" title="Photosynthesis">photosynthesis</a> from water and carbon dioxide, using energy from sunlight. It is used by plants to make <a href="/wiki/Cellulose" title="Cellulose">cellulose</a>—the most abundant carbohydrate in the world—for use in <a href="/wiki/Cell_wall" title="Cell wall">cell walls</a>, and by all living organisms to make <a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate">adenosine triphosphate</a> (ATP), which is used by the cell as energy.<sup id="cite_ref-froms_5-0" class="reference"><a href="#cite_note-froms-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">&#91;</span>6<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-r2_7-0" class="reference"><a href="#cite_note-r2-7"><span class="cite-bracket">&#91;</span>7<span class="cite-bracket">&#93;</span></a></sup> </p><p>In <a href="/wiki/Energy_metabolism" class="mw-redirect" title="Energy metabolism">energy metabolism</a>, glucose is the most important source of energy in all <a href="/wiki/Organism" title="Organism">organisms</a>. Glucose for metabolism is stored as a <a href="/wiki/Polymer" title="Polymer">polymer</a>, in plants mainly as <a href="/wiki/Amylose" title="Amylose">amylose</a> and <a href="/wiki/Amylopectin" title="Amylopectin">amylopectin</a>, and in animals as <a href="/wiki/Glycogen" title="Glycogen">glycogen</a>. Glucose circulates in the blood of animals as <a href="/wiki/Blood_sugar" class="mw-redirect" title="Blood sugar">blood sugar</a>.<sup id="cite_ref-froms_5-1" class="reference"><a href="#cite_note-froms-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-r2_7-1" class="reference"><a href="#cite_note-r2-7"><span class="cite-bracket">&#91;</span>7<span class="cite-bracket">&#93;</span></a></sup> The naturally occurring form is <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-glucose, while its <a href="/wiki/Stereoisomerism" title="Stereoisomerism">stereoisomer</a> <a href="/wiki/L-glucose" class="mw-redirect" title="L-glucose"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">l</span>-glucose</a> is produced synthetically in comparatively small amounts and is less biologically active.<sup id="cite_ref-r2_7-2" class="reference"><a href="#cite_note-r2-7"><span class="cite-bracket">&#91;</span>7<span class="cite-bracket">&#93;</span></a></sup> Glucose is a monosaccharide containing six carbon atoms and an <a href="/wiki/Aldehyde" title="Aldehyde">aldehyde</a> group, and is therefore an <a href="/wiki/Aldohexose" class="mw-redirect" title="Aldohexose">aldohexose</a>. The glucose molecule can exist in an open-chain (acyclic) as well as ring (cyclic) form. Glucose is naturally occurring and is found in its free state in fruits and other parts of plants. In animals, it is released from the breakdown of glycogen in a process known as <a href="/wiki/Glycogenolysis" title="Glycogenolysis">glycogenolysis</a>. </p><p>Glucose, as <a href="/wiki/Intravenous_sugar_solution" title="Intravenous sugar solution">intravenous sugar solution</a>, is on the <a href="/wiki/World_Health_Organization%27s_List_of_Essential_Medicines" class="mw-redirect" title="World Health Organization&#39;s List of Essential Medicines">World Health Organization's List of Essential Medicines</a>.<sup id="cite_ref-WHO21st_8-0" class="reference"><a href="#cite_note-WHO21st-8"><span class="cite-bracket">&#91;</span>8<span class="cite-bracket">&#93;</span></a></sup> It is also on the list in combination with <a href="/wiki/Sodium_chloride" title="Sodium chloride">sodium chloride</a> (table salt).<sup id="cite_ref-WHO21st_8-1" class="reference"><a href="#cite_note-WHO21st-8"><span class="cite-bracket">&#91;</span>8<span class="cite-bracket">&#93;</span></a></sup> </p><p>The name glucose is derived from <a href="/wiki/Ancient_Greek" title="Ancient Greek">Ancient Greek</a> <span title="Ancient Greek (to 1453)-language text"><span lang="grc">γλεῦκος</span></span> (<span title="Ancient Greek (to 1453)-language romanization"><i lang="grc-Latn">gleûkos</i></span>) 'wine, must', from <span title="Ancient Greek (to 1453)-language text"><span lang="grc">γλυκύς</span></span> (<span title="Ancient Greek (to 1453)-language romanization"><i lang="grc-Latn">glykýs</i></span>) 'sweet'.<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">&#91;</span>9<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">&#91;</span>10<span class="cite-bracket">&#93;</span></a></sup> The suffix <i><a href="/wiki/-ose" title="-ose">-ose</a></i> is a chemical classifier denoting a sugar. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="History">History</h2></div> <p>Glucose was first isolated from <a href="/wiki/Raisin" title="Raisin">raisins</a> in 1747 by the German chemist <a href="/wiki/Andreas_Sigismund_Marggraf" title="Andreas Sigismund Marggraf">Andreas Marggraf</a>.<sup id="cite_ref-Encyclopedia_of_Food_and_Health_11-0" class="reference"><a href="#cite_note-Encyclopedia_of_Food_and_Health-11"><span class="cite-bracket">&#91;</span>11<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">&#91;</span>12<span class="cite-bracket">&#93;</span></a></sup> Glucose was discovered in grapes by another German chemist&#160;&#8211;&#32;<a href="/wiki/Johann_Tobias_Lowitz" title="Johann Tobias Lowitz">Johann Tobias Lowitz</a>&#160;&#8211;&#32;in 1792, and distinguished as being different from cane sugar (<a href="/wiki/Sucrose" title="Sucrose">sucrose</a>). Glucose is the term coined by <a href="/wiki/Jean_Baptiste_Dumas" class="mw-redirect" title="Jean Baptiste Dumas">Jean Baptiste Dumas</a> in 1838, which has prevailed in the chemical literature. <a href="/wiki/Friedrich_August_Kekul%C3%A9" class="mw-redirect" title="Friedrich August Kekulé">Friedrich August Kekulé</a> proposed the term dextrose (from the <a href="/wiki/Latin" title="Latin">Latin</a> <span title="Latin-language text"><i lang="la">dexter</i></span>, meaning "right"), because in aqueous solution of glucose, the plane of linearly polarized light is turned to the right. In contrast, <a href="/wiki/L-fructose" class="mw-redirect" title="L-fructose">l-fructose</a> (usually referred to as <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-fructose) (a ketohexose) and l-glucose (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">l</span>-glucose) turn linearly <a href="/wiki/Polarization_(physics)" class="mw-redirect" title="Polarization (physics)">polarized</a> light to the left. The earlier notation according to the rotation of the plane of linearly polarized light (<i>d</i> and <i>l</i>-nomenclature) was later abandoned in favor of the <a href="/wiki/Optical_rotation#Chirality_prefixes" title="Optical rotation"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>- and <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">l</span>-notation</a>, which refers to the absolute configuration of the asymmetric center farthest from the carbonyl group, and in concordance with the configuration of <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>- or <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">l</span>-glyceraldehyde.<sup id="cite_ref-Robyt_7_13-0" class="reference"><a href="#cite_note-Robyt_7-13"><span class="cite-bracket">&#91;</span>13<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-Rosanoff_14-0" class="reference"><a href="#cite_note-Rosanoff-14"><span class="cite-bracket">&#91;</span>14<span class="cite-bracket">&#93;</span></a></sup> </p><p>Since glucose is a basic necessity of many organisms, a correct understanding of its <a href="/wiki/Chemical" class="mw-redirect" title="Chemical">chemical</a> makeup and structure contributed greatly to a general advancement in <a href="/wiki/Organic_chemistry" title="Organic chemistry">organic chemistry</a>. This understanding occurred largely as a result of the investigations of <a href="/wiki/Hermann_Emil_Fischer" class="mw-redirect" title="Hermann Emil Fischer">Emil Fischer</a>, a German chemist who received the 1902 <a href="/wiki/Nobel_Prize_in_Chemistry" title="Nobel Prize in Chemistry">Nobel Prize in Chemistry</a> for his findings.<sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">&#91;</span>15<span class="cite-bracket">&#93;</span></a></sup> The synthesis of glucose established the structure of organic material and consequently formed the first definitive validation of <a href="/wiki/Jacobus_Henricus_van_%27t_Hoff" title="Jacobus Henricus van &#39;t Hoff">Jacobus Henricus van 't Hoff</a>'s theories of chemical kinetics and the arrangements of chemical bonds in carbon-bearing molecules.<sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">&#91;</span>16<span class="cite-bracket">&#93;</span></a></sup> Between 1891 and 1894, Fischer established the <a href="/wiki/Stereochemical" class="mw-redirect" title="Stereochemical">stereochemical</a> configuration of all the known sugars and correctly predicted the possible <a href="/wiki/Isomer" title="Isomer">isomers</a>, applying <a href="/wiki/Van_%27t_Hoff_equation" title="Van &#39;t Hoff equation">Van 't Hoff equation</a> of asymmetrical carbon atoms. The names initially referred to the natural substances. Their <a href="/wiki/Enantiomers" class="mw-redirect" title="Enantiomers">enantiomers</a> were given the same name with the introduction of systematic nomenclatures, taking into account absolute stereochemistry (e.g. <a href="/wiki/Fischer_projection" title="Fischer projection">Fischer nomenclature</a>, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>/<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">l</span> nomenclature). </p><p>For the discovery of the metabolism of glucose <a href="/wiki/Otto_Meyerhof" class="mw-redirect" title="Otto Meyerhof">Otto Meyerhof</a> received the <a href="/wiki/Nobel_Prize_in_Physiology_or_Medicine" title="Nobel Prize in Physiology or Medicine">Nobel Prize in Physiology or Medicine</a> in 1922.<sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">&#91;</span>17<span class="cite-bracket">&#93;</span></a></sup> <a href="/wiki/Hans_von_Euler-Chelpin" title="Hans von Euler-Chelpin">Hans von Euler-Chelpin</a> was awarded the Nobel Prize in Chemistry along with <a href="/wiki/Arthur_Harden" title="Arthur Harden">Arthur Harden</a> in 1929 for their "research on the <a href="/wiki/Fermentation" title="Fermentation">fermentation</a> of sugar and their share of enzymes in this process".<sup id="cite_ref-18" class="reference"><a href="#cite_note-18"><span class="cite-bracket">&#91;</span>18<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">&#91;</span>19<span class="cite-bracket">&#93;</span></a></sup> In 1947, <a href="/wiki/Bernardo_Houssay" title="Bernardo Houssay">Bernardo Houssay</a> (for his discovery of the role of the <a href="/wiki/Pituitary_gland" title="Pituitary gland">pituitary gland</a> in the metabolism of glucose and the derived carbohydrates) as well as <a href="/wiki/Carl_Cori" class="mw-redirect" title="Carl Cori">Carl</a> and <a href="/wiki/Gerty_Cori" title="Gerty Cori">Gerty Cori</a> (for their discovery of the conversion of glycogen from glucose) received the Nobel Prize in Physiology or Medicine.<sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">&#91;</span>20<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-21" class="reference"><a href="#cite_note-21"><span class="cite-bracket">&#91;</span>21<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-22" class="reference"><a href="#cite_note-22"><span class="cite-bracket">&#91;</span>22<span class="cite-bracket">&#93;</span></a></sup> In 1970, <a href="/wiki/Luis_Leloir" class="mw-redirect" title="Luis Leloir">Luis Leloir</a> was awarded the Nobel Prize in Chemistry for the discovery of glucose-derived sugar nucleotides in the biosynthesis of carbohydrates.<sup id="cite_ref-23" class="reference"><a href="#cite_note-23"><span class="cite-bracket">&#91;</span>23<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Chemical_and_physical_properties">Chemical and physical properties</h2></div> <p>Glucose forms white or colorless solids that are highly <a href="/wiki/Soluble" class="mw-redirect" title="Soluble">soluble</a> in water and <a href="/wiki/Acetic_acid" title="Acetic acid">acetic acid</a> but poorly soluble in <a href="/wiki/Methanol" title="Methanol">methanol</a> and <a href="/wiki/Ethanol" title="Ethanol">ethanol</a>. They melt at 146&#160;°C (295&#160;°F) (<i>α</i>) and 150&#160;°C (302&#160;°F) (<i>beta</i>), <a href="/wiki/Chemical_decomposition" title="Chemical decomposition">decompose</a> starting at 188&#160;°C (370&#160;°F) with release of various volatile products, ultimately leaving a residue of <a href="/wiki/Carbon" title="Carbon">carbon</a>.<sup id="cite_ref-kang2020_24-0" class="reference"><a href="#cite_note-kang2020-24"><span class="cite-bracket">&#91;</span>24<span class="cite-bracket">&#93;</span></a></sup> Glucose has a <a href="/wiki/Acid_strength" title="Acid strength">pKa value</a> of 12.16 at 25&#160;°C (77&#160;°F) in water.<sup id="cite_ref-25" class="reference"><a href="#cite_note-25"><span class="cite-bracket">&#91;</span>25<span class="cite-bracket">&#93;</span></a></sup> </p><p>With six carbon atoms, it is classed as a <a href="/wiki/Hexose" title="Hexose">hexose</a>, a subcategory of the <a href="/wiki/Monosaccharide" title="Monosaccharide">monosaccharides</a>. <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-Glucose is one of the sixteen <a href="/wiki/Aldohexose" class="mw-redirect" title="Aldohexose">aldohexose</a> <a href="/wiki/Stereoisomer" class="mw-redirect" title="Stereoisomer">stereoisomers</a>. The <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-<a href="/wiki/Isomer" title="Isomer">isomer</a>, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-glucose, also known as dextrose, occurs widely in nature, but the <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">l</span>-isomer, <a href="/wiki/L-glucose" class="mw-redirect" title="L-glucose"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">l</span>-glucose</a>, does not. Glucose can be obtained by <a href="/wiki/Hydrolysis" title="Hydrolysis">hydrolysis</a> of carbohydrates such as milk sugar (<a href="/wiki/Lactose" title="Lactose">lactose</a>), cane sugar (sucrose), <a href="/wiki/Maltose" title="Maltose">maltose</a>, <a href="/wiki/Cellulose" title="Cellulose">cellulose</a>, <a href="/wiki/Glycogen" title="Glycogen">glycogen</a>, etc. Dextrose is commonly commercially manufactured from <a href="/wiki/Starch" title="Starch">starches</a>, such as <a href="/wiki/Corn_starch" title="Corn starch">corn starch</a> in the US and Japan, from potato and wheat starch in Europe, and from <a href="/wiki/Tapioca_starch" class="mw-redirect" title="Tapioca starch">tapioca starch</a> in tropical areas.<sup id="cite_ref-26" class="reference"><a href="#cite_note-26"><span class="cite-bracket">&#91;</span>26<span class="cite-bracket">&#93;</span></a></sup> The manufacturing process uses hydrolysis via pressurized steaming at controlled <a href="/wiki/PH" title="PH">pH</a> in a jet followed by further enzymatic depolymerization.<sup id="cite_ref-27" class="reference"><a href="#cite_note-27"><span class="cite-bracket">&#91;</span>27<span class="cite-bracket">&#93;</span></a></sup> Unbonded glucose is one of the main ingredients of <a href="/wiki/Honey" title="Honey">honey</a>.<sup id="cite_ref-28" class="reference"><a href="#cite_note-28"><span class="cite-bracket">&#91;</span>28<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-29" class="reference"><a href="#cite_note-29"><span class="cite-bracket">&#91;</span>29<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-30" class="reference"><a href="#cite_note-30"><span class="cite-bracket">&#91;</span>30<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-31" class="reference"><a href="#cite_note-31"><span class="cite-bracket">&#91;</span>31<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-32" class="reference"><a href="#cite_note-32"><span class="cite-bracket">&#91;</span>32<span class="cite-bracket">&#93;</span></a></sup> </p><p>The term <i>dextrose</i> is often used in a clinical (related to patient's health status) or nutritional context (related to dietary intake, such as food labels or dietary guidelines), while "glucose" is used in a biological or physiological context (chemical processes and molecular interactions),<sup id="cite_ref-33" class="reference"><a href="#cite_note-33"><span class="cite-bracket">&#91;</span>33<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-34" class="reference"><a href="#cite_note-34"><span class="cite-bracket">&#91;</span>34<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-wid_35-0" class="reference"><a href="#cite_note-wid-35"><span class="cite-bracket">&#91;</span>35<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-36" class="reference"><a href="#cite_note-36"><span class="cite-bracket">&#91;</span>36<span class="cite-bracket">&#93;</span></a></sup> but both terms refer to the same molecule, specifically D-glucose.<sup id="cite_ref-wid_35-1" class="reference"><a href="#cite_note-wid-35"><span class="cite-bracket">&#91;</span>35<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-pmid938892_37-0" class="reference"><a href="#cite_note-pmid938892-37"><span class="cite-bracket">&#91;</span>37<span class="cite-bracket">&#93;</span></a></sup> </p><p><i>Dextrose monohydrate</i> is the hydrated form of D-glucose, meaning that it is a glucose molecule with an additional water molecule attached.<sup id="cite_ref-chem_38-0" class="reference"><a href="#cite_note-chem-38"><span class="cite-bracket">&#91;</span>38<span class="cite-bracket">&#93;</span></a></sup> Its chemical formula is <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">12</sub>O<sub class="template-chem2-sub">6</sub></span>&#160;·&#160;<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">H<sub class="template-chem2-sub">2</sub>O</span>.<sup id="cite_ref-chem_38-1" class="reference"><a href="#cite_note-chem-38"><span class="cite-bracket">&#91;</span>38<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-api110617_39-0" class="reference"><a href="#cite_note-api110617-39"><span class="cite-bracket">&#91;</span>39<span class="cite-bracket">&#93;</span></a></sup> Dextrose monohydrate is also called <i>hydrated D-glucose</i>, and commonly manufactured from plant starches.<sup id="cite_ref-chem_38-2" class="reference"><a href="#cite_note-chem-38"><span class="cite-bracket">&#91;</span>38<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-diff_40-0" class="reference"><a href="#cite_note-diff-40"><span class="cite-bracket">&#91;</span>40<span class="cite-bracket">&#93;</span></a></sup> Dextrose monohydrate is utilized as the predominant type of dextrose in food applications, such as beverage mixes—it is a common form of glucose widely used as a nutrition supplement in production of foodstuffs. Dextrose monohydrate is primarily consumed in North America as a <a href="/wiki/Corn_syrup" title="Corn syrup">corn syrup</a> or <a href="/wiki/High-fructose_corn_syrup" title="High-fructose corn syrup">high-fructose corn syrup</a>.<sup id="cite_ref-wid_35-2" class="reference"><a href="#cite_note-wid-35"><span class="cite-bracket">&#91;</span>35<span class="cite-bracket">&#93;</span></a></sup> </p><p><i>Anhydrous dextrose</i>, on the other hand, is glucose that does not have any water molecules attached to it.<sup id="cite_ref-diff_40-1" class="reference"><a href="#cite_note-diff-40"><span class="cite-bracket">&#91;</span>40<span class="cite-bracket">&#93;</span></a></sup> <sup id="cite_ref-ahn1_41-0" class="reference"><a href="#cite_note-ahn1-41"><span class="cite-bracket">&#91;</span>41<span class="cite-bracket">&#93;</span></a></sup> Anhydrous chemical substances are commonly produced by eliminating water from a hydrated substance through methods such as heating or drying up (desiccation).<sup id="cite_ref-42" class="reference"><a href="#cite_note-42"><span class="cite-bracket">&#91;</span>42<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-a2_43-0" class="reference"><a href="#cite_note-a2-43"><span class="cite-bracket">&#91;</span>43<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-44" class="reference"><a href="#cite_note-44"><span class="cite-bracket">&#91;</span>44<span class="cite-bracket">&#93;</span></a></sup> Dextrose monohydrate can be dehydrated to anhydrous dextrose in industrial setting.<sup id="cite_ref-45" class="reference"><a href="#cite_note-45"><span class="cite-bracket">&#91;</span>45<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-46" class="reference"><a href="#cite_note-46"><span class="cite-bracket">&#91;</span>46<span class="cite-bracket">&#93;</span></a></sup> Dextrose monohydrate is composed of approximately 9.5% water by mass; through the process of dehydration, this water content is eliminated to yield anhydrous (dry) dextrose.<sup id="cite_ref-diff_40-2" class="reference"><a href="#cite_note-diff-40"><span class="cite-bracket">&#91;</span>40<span class="cite-bracket">&#93;</span></a></sup> </p><p>Anhydrous dextrose has the chemical formula <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">12</sub>O<sub class="template-chem2-sub">6</sub></span>, without any water molecule attached which is the same as glucose.<sup id="cite_ref-chem_38-3" class="reference"><a href="#cite_note-chem-38"><span class="cite-bracket">&#91;</span>38<span class="cite-bracket">&#93;</span></a></sup> Anhydrous dextrose on open air tends to absorb moisture and transform to the monohydrate, and it is more expensive to produce.<sup id="cite_ref-diff_40-3" class="reference"><a href="#cite_note-diff-40"><span class="cite-bracket">&#91;</span>40<span class="cite-bracket">&#93;</span></a></sup> Anhydrous dextrose (anhydrous D-glucose) has increased stability and increased shelf life,<sup id="cite_ref-a2_43-1" class="reference"><a href="#cite_note-a2-43"><span class="cite-bracket">&#91;</span>43<span class="cite-bracket">&#93;</span></a></sup> has medical applications, such as in oral <a href="/wiki/Glucose_tolerance_test" title="Glucose tolerance test">glucose tolerance test</a>.<sup id="cite_ref-47" class="reference"><a href="#cite_note-47"><span class="cite-bracket">&#91;</span>47<span class="cite-bracket">&#93;</span></a></sup> </p><p>Whereas molecular weight (molar mass) for D-glucose monohydrate is 198.17 g/mol,<sup id="cite_ref-48" class="reference"><a href="#cite_note-48"><span class="cite-bracket">&#91;</span>48<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-49" class="reference"><a href="#cite_note-49"><span class="cite-bracket">&#91;</span>49<span class="cite-bracket">&#93;</span></a></sup> that for anhydrous D-glucose is 180.16 g/mol<sup id="cite_ref-50" class="reference"><a href="#cite_note-50"><span class="cite-bracket">&#91;</span>50<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-51" class="reference"><a href="#cite_note-51"><span class="cite-bracket">&#91;</span>51<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-52" class="reference"><a href="#cite_note-52"><span class="cite-bracket">&#91;</span>52<span class="cite-bracket">&#93;</span></a></sup> The density of these two forms of glucose is also different.<sup class="noprint Inline-Template" style="white-space:nowrap;">&#91;<i><a href="/wiki/Wikipedia:Citing_sources" title="Wikipedia:Citing sources"><span title="Statement needs to be more specific about the content to which it refers. (March 2024)">specify</span></a></i>&#93;</sup> </p><p>In terms of chemical structure, glucose is a monosaccharide, that is, a simple sugar. Glucose contains six carbon atoms and an <a href="/wiki/Aldehyde_group" class="mw-redirect" title="Aldehyde group">aldehyde group</a>, and is therefore an <a href="/wiki/Aldohexose" class="mw-redirect" title="Aldohexose">aldohexose</a>. The glucose molecule can exist in an <a href="/wiki/Open-chain_compound" title="Open-chain compound">open-chain</a> (acyclic) as well as ring (cyclic) form—due to the presence of <a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">alcohol</a> and <a href="/wiki/Aldehyde" title="Aldehyde">aldehyde</a> or <a href="/wiki/Ketone" title="Ketone">ketone</a> functional groups, the form having the straight chain can easily convert into a chair-like <a href="/wiki/Hemiacetal" title="Hemiacetal">hemiacetal</a> ring structure commonly found in carbohydrates.<sup id="cite_ref-chem2_53-0" class="reference"><a href="#cite_note-chem2-53"><span class="cite-bracket">&#91;</span>53<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Structure_and_nomenclature">Structure and nomenclature</h3></div> <p>Glucose is present in solid form as a <a href="/wiki/Monohydrate" class="mw-redirect" title="Monohydrate">monohydrate</a> with a closed <a href="/wiki/Pyran" title="Pyran">pyran</a> ring (α-glucopyranose monohydrate, sometimes known less precisely by dextrose hydrate). In aqueous solution, on the other hand, it is an open-chain to a small extent and is present predominantly as α- or β-<a href="/wiki/Pyranose" title="Pyranose">pyranose</a>, which interconvert. From aqueous solutions, the three known forms can be crystallized: α-glucopyranose, β-glucopyranose and α-glucopyranose monohydrate.<sup id="cite_ref-Ullmann_54-0" class="reference"><a href="#cite_note-Ullmann-54"><span class="cite-bracket">&#91;</span>54<span class="cite-bracket">&#93;</span></a></sup> Glucose is a building block of the disaccharides lactose and sucrose (cane or beet sugar), of <a href="/wiki/Oligosaccharide" title="Oligosaccharide">oligosaccharides</a> such as <a href="/wiki/Raffinose" title="Raffinose">raffinose</a> and of <a href="/wiki/Polysaccharide" title="Polysaccharide">polysaccharides</a> such as <a href="/wiki/Starch" title="Starch">starch</a>, <a href="/wiki/Amylopectin" title="Amylopectin">amylopectin</a>, <a href="/wiki/Glycogen" title="Glycogen">glycogen</a>, and <a href="/wiki/Cellulose" title="Cellulose">cellulose</a>.<sup id="cite_ref-r2_7-3" class="reference"><a href="#cite_note-r2-7"><span class="cite-bracket">&#91;</span>7<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-pf_55-0" class="reference"><a href="#cite_note-pf-55"><span class="cite-bracket">&#91;</span>55<span class="cite-bracket">&#93;</span></a></sup> The <a href="/wiki/Glass_transition_temperature" class="mw-redirect" title="Glass transition temperature">glass transition temperature</a> of glucose is 31&#160;°C (88&#160;°F) and the Gordon–Taylor constant (an experimentally determined constant for the prediction of the glass transition temperature for different mass fractions of a mixture of two substances)<sup id="cite_ref-pf_55-1" class="reference"><a href="#cite_note-pf-55"><span class="cite-bracket">&#91;</span>55<span class="cite-bracket">&#93;</span></a></sup> is 4.5.<sup id="cite_ref-Caballero_1_76_56-0" class="reference"><a href="#cite_note-Caballero_1_76-56"><span class="cite-bracket">&#91;</span>56<span class="cite-bracket">&#93;</span></a></sup> </p> <table class="wikitable centered"> <tbody><tr style="background:#FFDEAD;"> <th colspan="3">Forms and projections of <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-glucose in comparison </th></tr> <tr class="background color5"> <th><a href="/wiki/Natta_projection" title="Natta projection">Natta projection</a> </th> <th colspan="2"><a href="/wiki/Haworth_projection" title="Haworth projection">Haworth projection</a> </th></tr> <tr class="background color2"> <td align="center" rowspan="2"><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:D-Glucose_Keilstrich.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/16/D-Glucose_Keilstrich.svg/100px-D-Glucose_Keilstrich.svg.png" decoding="async" width="100" height="187" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/16/D-Glucose_Keilstrich.svg/150px-D-Glucose_Keilstrich.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/16/D-Glucose_Keilstrich.svg/200px-D-Glucose_Keilstrich.svg.png 2x" data-file-width="138" data-file-height="258" /></a></span> </td> <td align="center"><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:Alpha-D-Glucofuranose.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f4/Alpha-D-Glucofuranose.svg/120px-Alpha-D-Glucofuranose.svg.png" decoding="async" width="120" height="111" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f4/Alpha-D-Glucofuranose.svg/180px-Alpha-D-Glucofuranose.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f4/Alpha-D-Glucofuranose.svg/240px-Alpha-D-Glucofuranose.svg.png 2x" data-file-width="187" data-file-height="173" /></a></span><div class="paragraphbreak" style="margin-top:0.5em"></div>α-<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-glucofuranose </td> <td align="center"><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:Beta-D-Glucofuranose.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/15/Beta-D-Glucofuranose.svg/120px-Beta-D-Glucofuranose.svg.png" decoding="async" width="120" height="111" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/15/Beta-D-Glucofuranose.svg/180px-Beta-D-Glucofuranose.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/15/Beta-D-Glucofuranose.svg/240px-Beta-D-Glucofuranose.svg.png 2x" data-file-width="187" data-file-height="173" /></a></span><div class="paragraphbreak" style="margin-top:0.5em"></div>β-<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-glucofuranose </td></tr> <tr class="background color2"> <td align="center"><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:Alpha-D-Glucopyranose.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c6/Alpha-D-Glucopyranose.svg/100px-Alpha-D-Glucopyranose.svg.png" decoding="async" width="100" height="108" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c6/Alpha-D-Glucopyranose.svg/150px-Alpha-D-Glucopyranose.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c6/Alpha-D-Glucopyranose.svg/200px-Alpha-D-Glucopyranose.svg.png 2x" data-file-width="157" data-file-height="170" /></a></span><div class="paragraphbreak" style="margin-top:0.5em"></div>α-<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-glucopyranose </td> <td align="center"><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:Beta-D-Glucopyranose.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/82/Beta-D-Glucopyranose.svg/100px-Beta-D-Glucopyranose.svg.png" decoding="async" width="100" height="108" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/82/Beta-D-Glucopyranose.svg/150px-Beta-D-Glucopyranose.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/82/Beta-D-Glucopyranose.svg/200px-Beta-D-Glucopyranose.svg.png 2x" data-file-width="157" data-file-height="170" /></a></span><div class="paragraphbreak" style="margin-top:0.5em"></div>β-<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-glucopyranose </td></tr> <tr class="background color5"> <th colspan="3">α-<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-Glucopyranose in (1) <a href="/wiki/Fischer_projection" title="Fischer projection">Tollens/Fischer</a> (2) Haworth projection (3) chair conformation (4) Mills projection </th></tr> <tr class="background color2"> <td align="center" colspan="3"><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:Alpha_glucose_views.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/31/Alpha_glucose_views.svg/500px-Alpha_glucose_views.svg.png" decoding="async" width="500" height="150" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/31/Alpha_glucose_views.svg/750px-Alpha_glucose_views.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/31/Alpha_glucose_views.svg/1000px-Alpha_glucose_views.svg.png 2x" data-file-width="1326" data-file-height="398" /></a></span> </td></tr></tbody></table> <div class="mw-heading mw-heading3"><h3 id="Open-chain_form">Open-chain form</h3></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Glucose_Fisher_to_Haworth.gif" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/af/Glucose_Fisher_to_Haworth.gif/220px-Glucose_Fisher_to_Haworth.gif" decoding="async" width="220" height="172" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/a/af/Glucose_Fisher_to_Haworth.gif 1.5x" data-file-width="231" data-file-height="181" /></a><figcaption>Glucose can exist in both a straight-chain and ring form.</figcaption></figure> <p>A open-chain form of glucose makes up less than 0.02% of the glucose molecules in an aqueous solution at equilibrium.<sup id="cite_ref-57" class="reference"><a href="#cite_note-57"><span class="cite-bracket">&#91;</span>57<span class="cite-bracket">&#93;</span></a></sup> The rest is one of two cyclic hemiacetal forms. In its <a href="/wiki/Open-chain" class="mw-redirect" title="Open-chain">open-chain</a> form, the glucose molecule has an open (as opposed to <a href="/wiki/Cyclic_compound" title="Cyclic compound">cyclic</a>) unbranched backbone of six carbon atoms, where C-1 is part of an <a href="/wiki/Aldehyde_group" class="mw-redirect" title="Aldehyde group">aldehyde group</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">H(C=O)−</span>. Therefore, glucose is also classified as an <a href="/wiki/Aldose" title="Aldose">aldose</a>, or an <a href="/wiki/Aldohexose" class="mw-redirect" title="Aldohexose">aldohexose</a>. The aldehyde group makes glucose a <a href="/wiki/Reducing_sugar" title="Reducing sugar">reducing sugar</a> giving a positive reaction with the <a href="/wiki/Fehling_test" class="mw-redirect" title="Fehling test">Fehling test</a>. </p> <div class="mw-heading mw-heading3"><h3 id="Cyclic_forms">Cyclic forms</h3></div> <style data-mw-deduplicate="TemplateStyles:r1237032888/mw-parser-output/.tmulti">.mw-parser-output .tmulti .multiimageinner{display:flex;flex-direction:column}.mw-parser-output .tmulti .trow{display:flex;flex-direction:row;clear:left;flex-wrap:wrap;width:100%;box-sizing:border-box}.mw-parser-output .tmulti .tsingle{margin:1px;float:left}.mw-parser-output .tmulti .theader{clear:both;font-weight:bold;text-align:center;align-self:center;background-color:transparent;width:100%}.mw-parser-output .tmulti .thumbcaption{background-color:transparent}.mw-parser-output .tmulti .text-align-left{text-align:left}.mw-parser-output .tmulti .text-align-right{text-align:right}.mw-parser-output .tmulti .text-align-center{text-align:center}@media all and (max-width:720px){.mw-parser-output .tmulti .thumbinner{width:100%!important;box-sizing:border-box;max-width:none!important;align-items:center}.mw-parser-output .tmulti .trow{justify-content:center}.mw-parser-output .tmulti .tsingle{float:none!important;max-width:100%!important;box-sizing:border-box;text-align:center}.mw-parser-output .tmulti .tsingle .thumbcaption{text-align:left}.mw-parser-output .tmulti .trow>.thumbcaption{text-align:center}}@media screen{html.skin-theme-clientpref-night .mw-parser-output .tmulti .multiimageinner img{background-color:white}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .tmulti .multiimageinner img{background-color:white}}</style><div class="thumb tmulti tright" style="background-color:white"><div class="thumbinner multiimageinner" style="width:593px;max-width:593px;background-color:white"><div class="trow"><div class="theader">Cyclic forms of glucose</div></div><div class="trow"><div class="tsingle" style="background-color:white;width:145px;max-width:145px"><div class="thumbimage" style="border:none;;height:155px;overflow:hidden"><span typeof="mw:File"><a href="/wiki/File:Alpha-D-Glucopyranose.svg" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c6/Alpha-D-Glucopyranose.svg/143px-Alpha-D-Glucopyranose.svg.png" decoding="async" width="143" height="155" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c6/Alpha-D-Glucopyranose.svg/215px-Alpha-D-Glucopyranose.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c6/Alpha-D-Glucopyranose.svg/286px-Alpha-D-Glucopyranose.svg.png 2x" data-file-width="157" data-file-height="170" /></a></span></div></div><div class="tsingle" style="background-color:white;width:145px;max-width:145px"><div class="thumbimage" style="border:none;;height:155px;overflow:hidden"><span typeof="mw:File"><a href="/wiki/File:Alpha-D-glucose-from-xtal-1979-3D-balls.png" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b9/Alpha-D-glucose-from-xtal-1979-3D-balls.png/143px-Alpha-D-glucose-from-xtal-1979-3D-balls.png" decoding="async" width="143" height="155" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b9/Alpha-D-glucose-from-xtal-1979-3D-balls.png/215px-Alpha-D-glucose-from-xtal-1979-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b9/Alpha-D-glucose-from-xtal-1979-3D-balls.png/286px-Alpha-D-glucose-from-xtal-1979-3D-balls.png 2x" data-file-width="1014" data-file-height="1100" /></a></span></div></div><div class="tsingle" style="background-color:white;width:145px;max-width:145px"><div class="thumbimage" style="border:none;;height:155px;overflow:hidden"><span typeof="mw:File"><a href="/wiki/File:Beta-D-Glucopyranose.svg" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/8/82/Beta-D-Glucopyranose.svg/143px-Beta-D-Glucopyranose.svg.png" decoding="async" width="143" height="155" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/82/Beta-D-Glucopyranose.svg/215px-Beta-D-Glucopyranose.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/82/Beta-D-Glucopyranose.svg/286px-Beta-D-Glucopyranose.svg.png 2x" data-file-width="157" data-file-height="170" /></a></span></div></div><div class="tsingle" style="background-color:white;width:148px;max-width:148px"><div class="thumbimage" style="border:none;;height:155px;overflow:hidden"><span typeof="mw:File"><a href="/wiki/File:Beta-D-glucose-from-xtal-3D-balls.png" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/61/Beta-D-glucose-from-xtal-3D-balls.png/146px-Beta-D-glucose-from-xtal-3D-balls.png" decoding="async" width="146" height="137" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/61/Beta-D-glucose-from-xtal-3D-balls.png/219px-Beta-D-glucose-from-xtal-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/61/Beta-D-glucose-from-xtal-3D-balls.png/292px-Beta-D-glucose-from-xtal-3D-balls.png 2x" data-file-width="1100" data-file-height="1034" /></a></span></div></div></div><div class="trow"><div class="tsingle" style="background-color:white;width:138px;max-width:138px"><div class="thumbimage" style="border:none;;height:146px;overflow:hidden"><span typeof="mw:File"><a href="/wiki/File:Alpha-D-Glucofuranose.svg" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f4/Alpha-D-Glucofuranose.svg/136px-Alpha-D-Glucofuranose.svg.png" decoding="async" width="136" height="126" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f4/Alpha-D-Glucofuranose.svg/204px-Alpha-D-Glucofuranose.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f4/Alpha-D-Glucofuranose.svg/272px-Alpha-D-Glucofuranose.svg.png 2x" data-file-width="187" data-file-height="173" /></a></span></div></div><div class="tsingle" style="background-color:white;width:149px;max-width:149px"><div class="thumbimage" style="border:none;;height:146px;overflow:hidden"><span typeof="mw:File"><a href="/wiki/File:Alpha-D-Glucofuranose_Molek%C3%BClbaukasten_9134_(crop).jpg" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/f/fe/Alpha-D-Glucofuranose_Molek%C3%BClbaukasten_9134_%28crop%29.jpg/147px-Alpha-D-Glucofuranose_Molek%C3%BClbaukasten_9134_%28crop%29.jpg" decoding="async" width="147" height="147" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/fe/Alpha-D-Glucofuranose_Molek%C3%BClbaukasten_9134_%28crop%29.jpg/221px-Alpha-D-Glucofuranose_Molek%C3%BClbaukasten_9134_%28crop%29.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/fe/Alpha-D-Glucofuranose_Molek%C3%BClbaukasten_9134_%28crop%29.jpg/294px-Alpha-D-Glucofuranose_Molek%C3%BClbaukasten_9134_%28crop%29.jpg 2x" data-file-width="3073" data-file-height="3074" /></a></span></div></div><div class="tsingle" style="background-color:white;width:138px;max-width:138px"><div class="thumbimage" style="border:none;;height:146px;overflow:hidden"><span typeof="mw:File"><a href="/wiki/File:Beta-D-Glucofuranose.svg" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/1/15/Beta-D-Glucofuranose.svg/136px-Beta-D-Glucofuranose.svg.png" decoding="async" width="136" height="126" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/15/Beta-D-Glucofuranose.svg/204px-Beta-D-Glucofuranose.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/15/Beta-D-Glucofuranose.svg/272px-Beta-D-Glucofuranose.svg.png 2x" data-file-width="187" data-file-height="173" /></a></span></div></div><div class="tsingle" style="background-color:white;width:160px;max-width:160px"><div class="thumbimage" style="border:none;;height:146px;overflow:hidden"><span typeof="mw:File"><a href="/wiki/File:Beta-D-Glucofuranose_Molek%C3%BClbaukasten_9136_(crop).jpg" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/8/87/Beta-D-Glucofuranose_Molek%C3%BClbaukasten_9136_%28crop%29.jpg/158px-Beta-D-Glucofuranose_Molek%C3%BClbaukasten_9136_%28crop%29.jpg" decoding="async" width="158" height="147" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/87/Beta-D-Glucofuranose_Molek%C3%BClbaukasten_9136_%28crop%29.jpg/237px-Beta-D-Glucofuranose_Molek%C3%BClbaukasten_9136_%28crop%29.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/87/Beta-D-Glucofuranose_Molek%C3%BClbaukasten_9136_%28crop%29.jpg/316px-Beta-D-Glucofuranose_Molek%C3%BClbaukasten_9136_%28crop%29.jpg 2x" data-file-width="3089" data-file-height="2873" /></a></span></div></div></div><div class="trow" style="display:flex"><div class="thumbcaption">From left to right: <a href="/wiki/Haworth_projection" title="Haworth projection">Haworth projections</a> and <a href="/wiki/Ball-and-stick_model" title="Ball-and-stick model">ball-and-stick</a> structures of the α- and β- <a href="/wiki/Anomer" title="Anomer">anomers</a> of <span style="font-size:85%;">D</span>-glucopyranose (top row) and <span style="font-size:85%;">D</span>-glucofuranose (bottom row)</div></div></div></div> <p>In solutions, the open-chain form of glucose (either "<span style="font-size:85%;">D</span>-" or "<span style="font-size:85%;">L</span>-") exists in equilibrium with several <a href="/wiki/Carbohydrate#Ring-straight_chain_isomerism" title="Carbohydrate">cyclic isomers</a>, each containing a ring of carbons closed by one oxygen atom. In aqueous solution, however, more than 99% of glucose molecules exist as <a href="/wiki/Pyranose" title="Pyranose">pyranose</a> forms. The open-chain form is limited to about 0.25%, and <a href="/wiki/Furanose" title="Furanose">furanose</a> forms exist in negligible amounts. The terms "glucose" and "<span style="font-size:85%;">D</span>-glucose" are generally used for these cyclic forms as well. The ring arises from the open-chain form by an intramolecular <a href="/wiki/Nucleophilic_addition" title="Nucleophilic addition">nucleophilic addition</a> reaction between the aldehyde group (at C-1) and either the C-4 or C-5 hydroxyl group, forming a <a href="/wiki/Hemiacetal" title="Hemiacetal">hemiacetal</a> linkage, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−C(OH)H−O−</span>. </p><p>The reaction between C-1 and C-5 yields a six-membered <a href="/wiki/Heterocycle" class="mw-redirect" title="Heterocycle">heterocyclic</a> system called a pyranose, which is a monosaccharide sugar (hence "-ose") containing a derivatised <a href="/wiki/Pyran" title="Pyran">pyran</a> skeleton. The (much rarer) reaction between C-1 and C-4 yields a five-membered furanose ring, named after the cyclic ether <a href="/wiki/Furan" title="Furan">furan</a>. In either case, each carbon in the ring has one hydrogen and one hydroxyl attached, except for the last carbon (C-4 or C-5) where the hydroxyl is replaced by the remainder of the open molecule (which is <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−(C(CH<sub class="template-chem2-sub">2</sub>OH)HOH)−H</span> or <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−(CHOH)−H</span> respectively). </p><p>The ring-closing reaction can give two products, denoted "α-" and "β-". When a glucopyranose molecule is drawn in the <a href="/wiki/Haworth_projection" title="Haworth projection">Haworth projection</a>, the designation "α-" means that the hydroxyl group attached to C-1 and the <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−CH<sub class="template-chem2-sub">2</sub>OH</span> group at C-5 lies on opposite sides of the ring's plane (a<a href="/wiki/Cis%E2%80%93trans_isomerism" title="Cis–trans isomerism"><i> trans</i></a> arrangement), while "β-" means that they are on the same side of the plane (a<a href="/wiki/Cis%E2%80%93trans_isomerism" title="Cis–trans isomerism"><i> cis</i></a> arrangement). Therefore, the open-chain isomer <span style="font-size:85%;">D</span>-glucose gives rise to four distinct cyclic isomers: α-<span style="font-size:85%;">D</span>-glucopyranose, β-<span style="font-size:85%;">D</span>-glucopyranose, α-<span style="font-size:85%;">D</span>-glucofuranose, and β-<span style="font-size:85%;">D</span>-glucofuranose. These five structures exist in equilibrium and interconvert, and the interconversion is much more rapid with acid <a href="/wiki/Catalysis" title="Catalysis">catalysis</a>. </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Alpha-D-glucose_and_beta-D-glucose_acid-catalyzed_mechanism.svg" class="mw-file-description" title="Widely proposed arrow-pushing mechanism for acid-catalyzed dynamic equilibrium between the α- and β- anomers of D-glucopyranose"><img alt="Widely proposed arrow-pushing mechanism for acid-catalyzed dynamic equilibrium between the α- and β- anomers of D-glucopyranose" src="//upload.wikimedia.org/wikipedia/commons/thumb/3/3a/Alpha-D-glucose_and_beta-D-glucose_acid-catalyzed_mechanism.svg/500px-Alpha-D-glucose_and_beta-D-glucose_acid-catalyzed_mechanism.svg.png" decoding="async" width="500" height="262" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/3a/Alpha-D-glucose_and_beta-D-glucose_acid-catalyzed_mechanism.svg/750px-Alpha-D-glucose_and_beta-D-glucose_acid-catalyzed_mechanism.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/3a/Alpha-D-glucose_and_beta-D-glucose_acid-catalyzed_mechanism.svg/1000px-Alpha-D-glucose_and_beta-D-glucose_acid-catalyzed_mechanism.svg.png 2x" data-file-width="477" data-file-height="250" /></a><figcaption>Widely proposed arrow-pushing mechanism for acid-catalyzed dynamic equilibrium between the α- and β- <a href="/wiki/Anomer" title="Anomer">anomers</a> of D-glucopyranose</figcaption></figure> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1237032888/mw-parser-output/.tmulti"><div class="thumb tmulti tright" style="background-color:white"><div class="thumbinner multiimageinner" style="width:392px;max-width:392px;background-color:white"><div class="trow"><div class="tsingle" style="background-color:white;width:165px;max-width:165px"><div class="thumbimage" style="border:none;;height:120px;overflow:hidden"><span typeof="mw:File"><a href="/wiki/File:ALPHA-D-Glucopyranose_V.1.png" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/b/be/ALPHA-D-Glucopyranose_V.1.png/163px-ALPHA-D-Glucopyranose_V.1.png" decoding="async" width="163" height="121" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/be/ALPHA-D-Glucopyranose_V.1.png/245px-ALPHA-D-Glucopyranose_V.1.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/be/ALPHA-D-Glucopyranose_V.1.png/326px-ALPHA-D-Glucopyranose_V.1.png 2x" data-file-width="2240" data-file-height="1662" /></a></span></div></div><div class="tsingle" style="background-color:white;width:223px;max-width:223px"><div class="thumbimage" style="border:none;;height:120px;overflow:hidden"><span typeof="mw:File"><a href="/wiki/File:BETA-D-Glucopyranose_V.1.png" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b9/BETA-D-Glucopyranose_V.1.png/221px-BETA-D-Glucopyranose_V.1.png" decoding="async" width="221" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b9/BETA-D-Glucopyranose_V.1.png/332px-BETA-D-Glucopyranose_V.1.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b9/BETA-D-Glucopyranose_V.1.png/442px-BETA-D-Glucopyranose_V.1.png 2x" data-file-width="2608" data-file-height="1420" /></a></span></div></div></div><div class="trow" style="display:flex"><div class="thumbcaption"><a href="/wiki/Chair_conformation" class="mw-redirect" title="Chair conformation">Chair conformations</a> of α- (left) and β- (right) <span style="font-size:85%;">D</span>-glucopyranose</div></div></div></div> <p>The other open-chain isomer <span style="font-size:85%;">L</span>-glucose similarly gives rise to four distinct cyclic forms of <span style="font-size:85%;">L</span>-glucose, each the mirror image of the corresponding <span style="font-size:85%;">D</span>-glucose. </p><p>The glucopyranose ring (α or β) can assume several non-planar shapes, analogous to the "chair" and "boat" conformations of <a href="/wiki/Cyclohexane" title="Cyclohexane">cyclohexane</a>. Similarly, the glucofuranose ring may assume several shapes, analogous to the "envelope" conformations of <a href="/wiki/Cyclopentane" title="Cyclopentane">cyclopentane</a>. </p><p>In the solid state, only the glucopyranose forms are observed. </p><p>Some derivatives of glucofuranose, such as <a href="/w/index.php?title=1,2-O-isopropylidene-D-glucofuranose&amp;action=edit&amp;redlink=1" class="new" title="1,2-O-isopropylidene-D-glucofuranose (page does not exist)">1,2-<i>O</i>-isopropylidene-<span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">D</span></span>-glucofuranose</a> are stable and can be obtained pure as crystalline solids.<sup id="cite_ref-taka1979_58-0" class="reference"><a href="#cite_note-taka1979-58"><span class="cite-bracket">&#91;</span>58<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-biel1999_59-0" class="reference"><a href="#cite_note-biel1999-59"><span class="cite-bracket">&#91;</span>59<span class="cite-bracket">&#93;</span></a></sup> For example, reaction of α-D-glucose with <a href="/w/index.php?title=P-tolylboronic_acid&amp;action=edit&amp;redlink=1" class="new" title="P-tolylboronic acid (page does not exist)"><i>para</i>-tolylboronic acid</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">H<sub class="template-chem2-sub">3</sub>C−(C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">4</sub>)−B(OH)<sub class="template-chem2-sub">2</sub></span> reforms the normal pyranose ring to yield the 4-fold ester α-D-glucofuranose-1,2:3,5-bis(<i>p</i>-tolylboronate).<sup id="cite_ref-chan2006_60-0" class="reference"><a href="#cite_note-chan2006-60"><span class="cite-bracket">&#91;</span>60<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Mutarotation">Mutarotation</h3></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Mutarotation_D-Glucose_V.1.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/5a/Mutarotation_D-Glucose_V.1.png/440px-Mutarotation_D-Glucose_V.1.png" decoding="async" width="440" height="97" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/5a/Mutarotation_D-Glucose_V.1.png/660px-Mutarotation_D-Glucose_V.1.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/5a/Mutarotation_D-Glucose_V.1.png/880px-Mutarotation_D-Glucose_V.1.png 2x" data-file-width="3153" data-file-height="697" /></a><figcaption>Mutarotation: <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-glucose molecules exist as cyclic hemiacetals that are epimeric (= diastereomeric) to each other. The epimeric ratio α:β is 36:64. In the α-D-glucopyranose (left), the blue-labelled hydroxy group is in the axial position at the anomeric centre, whereas in the β-D-glucopyranose (right) the blue-labelled hydroxy group is in equatorial position at the anomeric centre.</figcaption></figure> <p>Mutarotation consists of a temporary reversal of the ring-forming reaction, resulting in the open-chain form, followed by a reforming of the ring. The ring closure step may use a different <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−OH</span> group than the one recreated by the opening step (thus switching between pyranose and furanose forms), or the new hemiacetal group created on C-1 may have the same or opposite handedness as the original one (thus switching between the α and β forms). Thus, though the open-chain form is barely detectable in solution, it is an essential component of the equilibrium. </p><p>The open-chain form is <a href="/wiki/Chemical_stability" title="Chemical stability">thermodynamically unstable</a>, and it spontaneously <a href="/wiki/Isomer" title="Isomer">isomerizes</a> to the cyclic forms. (Although the ring closure reaction could in theory create four- or three-atom rings, these would be highly strained, and are not observed in practice.) In solutions at <a href="/wiki/Room_temperature" title="Room temperature">room temperature</a>, the four cyclic isomers interconvert over a time scale of hours, in a process called <a href="/wiki/Mutarotation" title="Mutarotation">mutarotation</a>.<sup id="cite_ref-61" class="reference"><a href="#cite_note-61"><span class="cite-bracket">&#91;</span>61<span class="cite-bracket">&#93;</span></a></sup> Starting from any proportions, the mixture converges to a stable ratio of α:β 36:64. The ratio would be α:β 11:89 if it were not for the influence of the <a href="/wiki/Anomeric_effect" title="Anomeric effect">anomeric effect</a>.<sup id="cite_ref-62" class="reference"><a href="#cite_note-62"><span class="cite-bracket">&#91;</span>62<span class="cite-bracket">&#93;</span></a></sup> Mutarotation is considerably slower at temperatures close to 0&#160;°C (32&#160;°F). </p> <div class="mw-heading mw-heading3"><h3 id="Optical_activity">Optical activity</h3></div> <p>Whether in water or the solid form, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-(+)-glucose is <a href="/wiki/Dextrorotation_and_levorotation" class="mw-redirect" title="Dextrorotation and levorotation">dextrorotatory</a>, meaning it will rotate the direction of <a href="/wiki/Polarized_light" class="mw-redirect" title="Polarized light">polarized light</a> clockwise as seen looking toward the light source. The effect is due to the <a href="/wiki/Chirality" title="Chirality">chirality</a> of the molecules, and indeed the mirror-image isomer, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">l</span>-(−)-glucose, is <a href="/wiki/Dextrorotation_and_levorotation" class="mw-redirect" title="Dextrorotation and levorotation">levorotatory</a> (rotates polarized light counterclockwise) by the same amount. The strength of the effect is different for each of the five <a href="/wiki/Tautomer" title="Tautomer">tautomers</a>. </p><p>The <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>- prefix does not refer directly to the optical properties of the compound. It indicates that the C-5 chiral centre has the same handedness as that of <a href="/wiki/Glyceraldehyde" title="Glyceraldehyde"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-glyceraldehyde</a> (which was so labelled because it is dextrorotatory). The fact that <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-glucose is dextrorotatory is a combined effect of its four chiral centres, not just of C-5; some of the other <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-aldohexoses are levorotatory. </p><p>The conversion between the two anomers can be observed in a <a href="/wiki/Polarimeter" title="Polarimeter">polarimeter</a> since pure α-<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-glucose has a specific rotation angle of +112.2° mL/(dm·g), pure β-<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-glucose of +17.5° mL/(dm·g).<sup id="cite_ref-Hesse_63-0" class="reference"><a href="#cite_note-Hesse-63"><span class="cite-bracket">&#91;</span>63<span class="cite-bracket">&#93;</span></a></sup> When equilibrium has been reached after a certain time due to mutarotation, the angle of rotation is +52.7° mL/(dm·g).<sup id="cite_ref-Hesse_63-1" class="reference"><a href="#cite_note-Hesse-63"><span class="cite-bracket">&#91;</span>63<span class="cite-bracket">&#93;</span></a></sup> By adding acid or base, this transformation is much accelerated. The equilibration takes place via the open-chain aldehyde form. </p> <div class="mw-heading mw-heading3"><h3 id="Isomerisation">Isomerisation</h3></div> <p>In dilute <a href="/wiki/Sodium_hydroxide" title="Sodium hydroxide">sodium hydroxide</a> or other dilute bases, the monosaccharides <a href="/wiki/Mannose" title="Mannose">mannose</a>, glucose and <a href="/wiki/Fructose" title="Fructose">fructose</a> interconvert (via a <a href="/wiki/Lobry_de_Bruyn%E2%80%93Van_Ekenstein_transformation" title="Lobry de Bruyn–Van Ekenstein transformation">Lobry de Bruyn–Alberda–Van Ekenstein transformation</a>), so that a balance between these isomers is formed. This reaction proceeds via an <a href="/wiki/Enediol" class="mw-redirect" title="Enediol">enediol</a>: </p><p><span class="mw-default-size" typeof="mw:File/Frameless"><a href="/wiki/File:Glucose_Fructose_Mannose_Gleichgewicht.png" class="mw-file-description" title="Glucose-Fructose-Mannose-isomerisation"><img alt="Glucose-Fructose-Mannose-isomerisation" src="//upload.wikimedia.org/wikipedia/commons/thumb/7/79/Glucose_Fructose_Mannose_Gleichgewicht.png/440px-Glucose_Fructose_Mannose_Gleichgewicht.png" decoding="async" width="440" height="202" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/7/79/Glucose_Fructose_Mannose_Gleichgewicht.png 1.5x" data-file-width="657" data-file-height="302" /></a></span> </p> <div class="mw-heading mw-heading2"><h2 id="Biochemical_properties">Biochemical properties</h2></div> <table class="toccolours collapsible collapsed" style="width:100%; text-align:left;"> <tbody><tr> <th>Metabolism of common <a href="/wiki/Monosaccharide" title="Monosaccharide">monosaccharides</a> and some biochemical reactions of glucose </th></tr> <tr> <td><figure class="mw-halign-none" typeof="mw:File"><a href="/wiki/File:Metabolism_of_common_monosaccharides,_and_related_reactions.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/63/Metabolism_of_common_monosaccharides%2C_and_related_reactions.png/1000px-Metabolism_of_common_monosaccharides%2C_and_related_reactions.png" decoding="async" width="1000" height="1213" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/63/Metabolism_of_common_monosaccharides%2C_and_related_reactions.png/1500px-Metabolism_of_common_monosaccharides%2C_and_related_reactions.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/63/Metabolism_of_common_monosaccharides%2C_and_related_reactions.png/2000px-Metabolism_of_common_monosaccharides%2C_and_related_reactions.png 2x" data-file-width="2785" data-file-height="3379" /></a><figcaption></figcaption></figure> </td></tr></tbody></table> <p>Glucose is the most abundant monosaccharide. Glucose is also the most widely used aldohexose in most living organisms. One possible explanation for this is that glucose has a lower tendency than other aldohexoses to react nonspecifically with the <a href="/wiki/Amine" title="Amine">amine</a> groups of <a href="/wiki/Protein" title="Protein">proteins</a>.<sup id="cite_ref-Higgins_64-0" class="reference"><a href="#cite_note-Higgins-64"><span class="cite-bracket">&#91;</span>64<span class="cite-bracket">&#93;</span></a></sup> This reaction—<a href="/wiki/Glycation" title="Glycation">glycation</a>—impairs or destroys the function of many proteins,<sup id="cite_ref-Higgins_64-1" class="reference"><a href="#cite_note-Higgins-64"><span class="cite-bracket">&#91;</span>64<span class="cite-bracket">&#93;</span></a></sup> e.g. in <a href="/wiki/Glycated_hemoglobin" title="Glycated hemoglobin">glycated hemoglobin</a>. Glucose's low rate of glycation can be attributed to its having a more stable <a href="#Cyclic_forms">cyclic form</a> compared to other aldohexoses, which means it spends less time than they do in its reactive <a href="#Open-chain_form">open-chain form</a>.<sup id="cite_ref-Higgins_64-2" class="reference"><a href="#cite_note-Higgins-64"><span class="cite-bracket">&#91;</span>64<span class="cite-bracket">&#93;</span></a></sup> The reason for glucose having the most stable cyclic form of all the aldohexoses is that its <a href="/wiki/Hydroxy_group" title="Hydroxy group">hydroxy groups</a> (with the exception of the hydroxy group on the anomeric carbon of <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-glucose) are in the <a href="/wiki/Cyclohexane_conformation" title="Cyclohexane conformation">equatorial position</a>. Presumably, glucose is the most abundant natural monosaccharide because it is less glycated with proteins than other monosaccharides.<sup id="cite_ref-Higgins_64-3" class="reference"><a href="#cite_note-Higgins-64"><span class="cite-bracket">&#91;</span>64<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-Stryer_531_65-0" class="reference"><a href="#cite_note-Stryer_531-65"><span class="cite-bracket">&#91;</span>65<span class="cite-bracket">&#93;</span></a></sup> Another hypothesis is that glucose, being the only <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-aldohexose that has all five hydroxy substituents in the <a href="/wiki/Equatorial_bond" class="mw-redirect" title="Equatorial bond">equatorial</a> position in the form of β-<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-glucose, is more readily accessible to chemical reactions,<sup id="cite_ref-Garrett_66-0" class="reference"><a href="#cite_note-Garrett-66"><span class="cite-bracket">&#91;</span>66<span class="cite-bracket">&#93;</span></a></sup><sup class="reference nowrap"><span title="Page / location: 194, 199">&#58;&#8202;194,&#8202;199&#8202;</span></sup> for example, for <a href="/wiki/Esterification" class="mw-redirect" title="Esterification">esterification</a><sup id="cite_ref-Voet_67-0" class="reference"><a href="#cite_note-Voet-67"><span class="cite-bracket">&#91;</span>67<span class="cite-bracket">&#93;</span></a></sup><sup class="reference nowrap"><span title="Page / location: 363">&#58;&#8202;363&#8202;</span></sup> or <a href="/wiki/Acetal" title="Acetal">acetal</a> formation.<sup id="cite_ref-68" class="reference"><a href="#cite_note-68"><span class="cite-bracket">&#91;</span>68<span class="cite-bracket">&#93;</span></a></sup> For this reason, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-glucose is also a highly preferred building block in natural polysaccharides (glycans). Polysaccharides that are composed solely of glucose are termed <a href="/wiki/Glucan" title="Glucan">glucans</a>. </p><p>Glucose is produced by plants through photosynthesis using sunlight,<sup id="cite_ref-photo_69-0" class="reference"><a href="#cite_note-photo-69"><span class="cite-bracket">&#91;</span>69<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-Löffler/Petrides_195_70-0" class="reference"><a href="#cite_note-Löffler/Petrides_195-70"><span class="cite-bracket">&#91;</span>70<span class="cite-bracket">&#93;</span></a></sup> water and carbon dioxide and can be used by all living organisms as an energy and carbon source. However, most glucose does not occur in its free form, but in the form of its polymers, i.e. lactose, sucrose, starch and others which are energy reserve substances, and cellulose and <a href="/wiki/Chitin" title="Chitin">chitin</a>, which are components of the cell wall in plants or <a href="/wiki/Fungi" class="mw-redirect" title="Fungi">fungi</a> and <a href="/wiki/Arthropod" title="Arthropod">arthropods</a>, respectively. These polymers, when consumed by animals, fungi and bacteria, are degraded to glucose using enzymes. All animals are also able to produce glucose themselves from certain precursors as the need arises. <a href="/wiki/Neuron" title="Neuron">Neurons</a>, cells of the <a href="/wiki/Renal_medulla" title="Renal medulla">renal medulla</a> and <a href="/wiki/Erythrocytes" class="mw-redirect" title="Erythrocytes">erythrocytes</a> depend on glucose for their energy production.<sup id="cite_ref-Löffler/Petrides_195_70-1" class="reference"><a href="#cite_note-Löffler/Petrides_195-70"><span class="cite-bracket">&#91;</span>70<span class="cite-bracket">&#93;</span></a></sup> In adult humans, there is about 18&#160;g (0.63&#160;oz) of glucose,<sup id="cite_ref-Satyanarayana_71-0" class="reference"><a href="#cite_note-Satyanarayana-71"><span class="cite-bracket">&#91;</span>71<span class="cite-bracket">&#93;</span></a></sup> of which about 4&#160;g (0.14&#160;oz) is present in the blood.<sup id="cite_ref-72" class="reference"><a href="#cite_note-72"><span class="cite-bracket">&#91;</span>72<span class="cite-bracket">&#93;</span></a></sup> Approximately 180–220&#160;g (6.3–7.8&#160;oz) of glucose is produced in the liver of an adult in 24 hours.<sup id="cite_ref-Satyanarayana_71-1" class="reference"><a href="#cite_note-Satyanarayana-71"><span class="cite-bracket">&#91;</span>71<span class="cite-bracket">&#93;</span></a></sup> </p><p>Many of the long-term complications of <a href="/wiki/Diabetes" title="Diabetes">diabetes</a> (e.g., <a href="/wiki/Visual_impairment" title="Visual impairment">blindness</a>, <a href="/wiki/Kidney_failure" title="Kidney failure">kidney failure</a>, and <a href="/wiki/Peripheral_neuropathy" title="Peripheral neuropathy">peripheral neuropathy</a>) are probably due to the glycation of proteins or <a href="/wiki/Lipid" title="Lipid">lipids</a>.<sup id="cite_ref-73" class="reference"><a href="#cite_note-73"><span class="cite-bracket">&#91;</span>73<span class="cite-bracket">&#93;</span></a></sup> In contrast, <a href="/wiki/Enzyme" title="Enzyme">enzyme</a>-regulated addition of sugars to protein is called <a href="/wiki/Glycosylation" title="Glycosylation">glycosylation</a> and is essential for the function of many proteins.<sup id="cite_ref-varki_74-0" class="reference"><a href="#cite_note-varki-74"><span class="cite-bracket">&#91;</span>74<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Uptake">Uptake</h3></div> <p>Ingested glucose initially binds to the receptor for sweet taste on the tongue in humans. This complex of the proteins <a href="/wiki/T1R2" class="mw-redirect" title="T1R2">T1R2</a> and <a href="/wiki/T1R3" class="mw-redirect" title="T1R3">T1R3</a> makes it possible to identify glucose-containing food sources.<sup id="cite_ref-fca_75-0" class="reference"><a href="#cite_note-fca-75"><span class="cite-bracket">&#91;</span>75<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-Löffler/Petrides_404_76-0" class="reference"><a href="#cite_note-Löffler/Petrides_404-76"><span class="cite-bracket">&#91;</span>76<span class="cite-bracket">&#93;</span></a></sup> Glucose mainly comes from food—about 300&#160;g (11&#160;oz) per day is produced by conversion of food,<sup id="cite_ref-Löffler/Petrides_404_76-1" class="reference"><a href="#cite_note-Löffler/Petrides_404-76"><span class="cite-bracket">&#91;</span>76<span class="cite-bracket">&#93;</span></a></sup> but it is also synthesized from other metabolites in the body's cells. In humans, the breakdown of glucose-containing polysaccharides happens in part already during <a href="/wiki/Chewing" title="Chewing">chewing</a> by means of <a href="/wiki/Amylase" title="Amylase">amylase</a>, which is contained in <a href="/wiki/Saliva" title="Saliva">saliva</a>, as well as by <a href="/wiki/Maltase" title="Maltase">maltase</a>, <a href="/wiki/Lactase" title="Lactase">lactase</a>, and <a href="/wiki/Sucrase" title="Sucrase">sucrase</a> on the <a href="/wiki/Brush_border" title="Brush border">brush border</a> of the <a href="/wiki/Small_intestine" title="Small intestine">small intestine</a>. Glucose is a building block of many carbohydrates and can be split off from them using certain enzymes. <a href="/wiki/Glucosidases" title="Glucosidases">Glucosidases</a>, a subgroup of the glycosidases, first catalyze the hydrolysis of long-chain glucose-containing polysaccharides, removing terminal glucose. In turn, disaccharides are mostly degraded by specific glycosidases to glucose. The names of the degrading enzymes are often derived from the particular poly- and disaccharide; inter alia, for the degradation of polysaccharide chains there are amylases (named after amylose, a component of starch), cellulases (named after cellulose), chitinases (named after chitin), and more. Furthermore, for the cleavage of disaccharides, there are maltase, lactase, sucrase, <a href="/wiki/Trehalase" title="Trehalase">trehalase</a>, and others. In humans, about 70 genes are known that code for glycosidases. They have functions in the digestion and degradation of glycogen, <a href="/wiki/Sphingolipid" title="Sphingolipid">sphingolipids</a>, <a href="/wiki/Mucopolysaccharides" class="mw-redirect" title="Mucopolysaccharides">mucopolysaccharides</a>, and poly(<a href="/wiki/Adenosine_diphosphate_ribose" title="Adenosine diphosphate ribose">ADP-ribose</a>). Humans do not produce cellulases, chitinases, or trehalases, but the bacteria in the <a href="/wiki/Gut_microbiota" title="Gut microbiota">gut microbiota</a> do. </p><p>In order to get into or out of cell membranes of cells and membranes of cell compartments, glucose requires special transport proteins from the <a href="/wiki/Major_facilitator_superfamily" title="Major facilitator superfamily">major facilitator superfamily</a>. In the small intestine (more precisely, in the <a href="/wiki/Jejunum" title="Jejunum">jejunum</a>),<sup id="cite_ref-Harper_641_77-0" class="reference"><a href="#cite_note-Harper_641-77"><span class="cite-bracket">&#91;</span>77<span class="cite-bracket">&#93;</span></a></sup> glucose is taken up into the intestinal <a href="/wiki/Epithelium" title="Epithelium">epithelium</a> with the help of <a href="/wiki/Glucose_transporter" title="Glucose transporter">glucose transporters</a><sup id="cite_ref-78" class="reference"><a href="#cite_note-78"><span class="cite-bracket">&#91;</span>78<span class="cite-bracket">&#93;</span></a></sup> via a <a href="/wiki/Secondary_active_transport" class="mw-redirect" title="Secondary active transport">secondary active transport</a> mechanism called sodium ion-glucose <a href="/wiki/Symport" class="mw-redirect" title="Symport">symport</a> via <a href="/wiki/Sodium/glucose_cotransporter_1" title="Sodium/glucose cotransporter 1">sodium/glucose cotransporter 1</a> (SGLT1).<sup id="cite_ref-Löffler/Petrides_199_79-0" class="reference"><a href="#cite_note-Löffler/Petrides_199-79"><span class="cite-bracket">&#91;</span>79<span class="cite-bracket">&#93;</span></a></sup> Further transfer occurs on the <a href="/wiki/Basolateral" class="mw-redirect" title="Basolateral">basolateral</a> side of the intestinal epithelial cells via the glucose transporter <a href="/wiki/GLUT2" title="GLUT2">GLUT2</a>,<sup id="cite_ref-Löffler/Petrides_199_79-1" class="reference"><a href="#cite_note-Löffler/Petrides_199-79"><span class="cite-bracket">&#91;</span>79<span class="cite-bracket">&#93;</span></a></sup> as well uptake into <a href="/wiki/Hepatocyte" title="Hepatocyte">liver cells</a>, kidney cells, cells of the <a href="/wiki/Pancreatic_islets" title="Pancreatic islets">islets of Langerhans</a>, <a href="/wiki/Neuron" title="Neuron">neurons</a>, <a href="/wiki/Astrocyte" title="Astrocyte">astrocytes</a>, and <a href="/wiki/Tanycyte" title="Tanycyte">tanycytes</a>.<sup id="cite_ref-80" class="reference"><a href="#cite_note-80"><span class="cite-bracket">&#91;</span>80<span class="cite-bracket">&#93;</span></a></sup> Glucose enters the liver via the <a href="/wiki/Portal_vein" title="Portal vein">portal vein</a> and is stored there as a cellular glycogen.<sup id="cite_ref-Löffler/Petrides_214_81-0" class="reference"><a href="#cite_note-Löffler/Petrides_214-81"><span class="cite-bracket">&#91;</span>81<span class="cite-bracket">&#93;</span></a></sup> In the liver cell, it is <a href="/wiki/Phosphorylation" title="Phosphorylation">phosphorylated</a> by <a href="/wiki/Glucokinase" title="Glucokinase">glucokinase</a> at position 6 to form <a href="/wiki/Glucose_6-phosphate" title="Glucose 6-phosphate">glucose 6-phosphate</a>, which cannot leave the cell. <a href="/wiki/Glucose_6-phosphatase" title="Glucose 6-phosphatase">Glucose 6-phosphatase</a> can convert glucose 6-phosphate back into glucose exclusively in the liver, so the body can maintain a sufficient blood glucose concentration. In other cells, uptake happens by passive transport through one of the 14 GLUT proteins.<sup id="cite_ref-Löffler/Petrides_199_79-2" class="reference"><a href="#cite_note-Löffler/Petrides_199-79"><span class="cite-bracket">&#91;</span>79<span class="cite-bracket">&#93;</span></a></sup> In the other cell types, phosphorylation occurs through a <a href="/wiki/Hexokinase" title="Hexokinase">hexokinase</a>, whereupon glucose can no longer diffuse out of the cell. </p><p>The glucose transporter <a href="/wiki/GLUT1" title="GLUT1">GLUT1</a> is produced by most cell types and is of particular importance for nerve cells and pancreatic <a href="/wiki/Beta_cell" title="Beta cell">β-cells</a>.<sup id="cite_ref-Löffler/Petrides_199_79-3" class="reference"><a href="#cite_note-Löffler/Petrides_199-79"><span class="cite-bracket">&#91;</span>79<span class="cite-bracket">&#93;</span></a></sup> <a href="/wiki/GLUT3" title="GLUT3">GLUT3</a> is highly expressed in nerve cells.<sup id="cite_ref-Löffler/Petrides_199_79-4" class="reference"><a href="#cite_note-Löffler/Petrides_199-79"><span class="cite-bracket">&#91;</span>79<span class="cite-bracket">&#93;</span></a></sup> Glucose from the bloodstream is taken up by <a href="/wiki/GLUT4" title="GLUT4">GLUT4</a> from <a href="/wiki/Muscle_cell" title="Muscle cell">muscle cells</a> (of the <a href="/wiki/Skeletal_muscle" title="Skeletal muscle">skeletal muscle</a><sup id="cite_ref-82" class="reference"><a href="#cite_note-82"><span class="cite-bracket">&#91;</span>82<span class="cite-bracket">&#93;</span></a></sup> and <a href="/wiki/Heart_muscle" class="mw-redirect" title="Heart muscle">heart muscle</a>) and <a href="/wiki/Fat_cell" class="mw-redirect" title="Fat cell">fat cells</a>.<sup id="cite_ref-83" class="reference"><a href="#cite_note-83"><span class="cite-bracket">&#91;</span>83<span class="cite-bracket">&#93;</span></a></sup> <a href="/wiki/GLUT14" class="mw-redirect" title="GLUT14">GLUT14</a> is expressed exclusively in <a href="/wiki/Testicle" title="Testicle">testicles</a>.<sup id="cite_ref-84" class="reference"><a href="#cite_note-84"><span class="cite-bracket">&#91;</span>84<span class="cite-bracket">&#93;</span></a></sup> Excess glucose is broken down and converted into fatty acids, which are stored as <a href="/wiki/Triglyceride" title="Triglyceride">triglycerides</a>. In the <a href="/wiki/Kidney" title="Kidney">kidneys</a>, glucose in the urine is absorbed via SGLT1 and <a href="/wiki/SGLT2" class="mw-redirect" title="SGLT2">SGLT2</a> in the apical cell membranes and transmitted via GLUT2 in the basolateral cell membranes.<sup id="cite_ref-85" class="reference"><a href="#cite_note-85"><span class="cite-bracket">&#91;</span>85<span class="cite-bracket">&#93;</span></a></sup> About 90% of kidney glucose reabsorption is via SGLT2 and about 3% via SGLT1.<sup id="cite_ref-86" class="reference"><a href="#cite_note-86"><span class="cite-bracket">&#91;</span>86<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Biosynthesis">Biosynthesis</h3></div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">Main articles: <a href="/wiki/Gluconeogenesis" title="Gluconeogenesis">Gluconeogenesis</a> and <a href="/wiki/Glycogenolysis" title="Glycogenolysis">Glycogenolysis</a></div> <p>In plants and some <a href="/wiki/Prokaryote" title="Prokaryote">prokaryotes</a>, glucose is a product of <a href="/wiki/Photosynthesis" title="Photosynthesis">photosynthesis</a>.<sup id="cite_ref-photo_69-1" class="reference"><a href="#cite_note-photo-69"><span class="cite-bracket">&#91;</span>69<span class="cite-bracket">&#93;</span></a></sup> Glucose is also formed by the breakdown of polymeric forms of glucose like <a href="/wiki/Glycogen" title="Glycogen">glycogen</a> (in animals and <a href="/wiki/Mushroom" title="Mushroom">mushrooms</a>) or starch (in plants). The cleavage of glycogen is termed glycogenolysis, the cleavage of starch is called starch degradation.<sup id="cite_ref-87" class="reference"><a href="#cite_note-87"><span class="cite-bracket">&#91;</span>87<span class="cite-bracket">&#93;</span></a></sup> </p><p>The metabolic pathway that begins with molecules containing two to four carbon atoms (C) and ends in the glucose molecule containing six carbon atoms is called gluconeogenesis and occurs in all living organisms. The smaller starting materials are the result of other metabolic pathways. Ultimately almost all <a href="/wiki/Biomolecule" title="Biomolecule">biomolecules</a> come from the assimilation of carbon dioxide in plants and microbes during photosynthesis.<sup id="cite_ref-Voet_67-1" class="reference"><a href="#cite_note-Voet-67"><span class="cite-bracket">&#91;</span>67<span class="cite-bracket">&#93;</span></a></sup><sup class="reference nowrap"><span title="Page / location: 359">&#58;&#8202;359&#8202;</span></sup> The free energy of formation of α-<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-glucose is 917.2 kilojoules per mole.<sup id="cite_ref-Voet_67-2" class="reference"><a href="#cite_note-Voet-67"><span class="cite-bracket">&#91;</span>67<span class="cite-bracket">&#93;</span></a></sup><sup class="reference nowrap"><span title="Page / location: 59">&#58;&#8202;59&#8202;</span></sup> In humans, gluconeogenesis occurs in the liver and kidney,<sup id="cite_ref-Szablewski_88-0" class="reference"><a href="#cite_note-Szablewski-88"><span class="cite-bracket">&#91;</span>88<span class="cite-bracket">&#93;</span></a></sup> but also in other cell types. In the liver about 150&#160;g (5.3&#160;oz) of glycogen are stored, in skeletal muscle about 250&#160;g (8.8&#160;oz).<sup id="cite_ref-Löffler/Petrides_389_89-0" class="reference"><a href="#cite_note-Löffler/Petrides_389-89"><span class="cite-bracket">&#91;</span>89<span class="cite-bracket">&#93;</span></a></sup> However, the glucose released in muscle cells upon cleavage of the glycogen can not be delivered to the circulation because glucose is phosphorylated by the hexokinase, and a glucose-6-phosphatase is not expressed to remove the phosphate group. Unlike for glucose, there is no transport protein for <a href="/wiki/Glucose-6-phosphate_dehydrogenase_(coenzyme-F420)" title="Glucose-6-phosphate dehydrogenase (coenzyme-F420)">glucose-6-phosphate</a>. Gluconeogenesis allows the organism to build up glucose from other metabolites, including <a href="/wiki/Lactic_acid" title="Lactic acid">lactate</a> or certain <a href="/wiki/Amino_acid" title="Amino acid">amino acids</a>, while consuming energy. The renal <a href="/wiki/Tubular_cell" class="mw-redirect" title="Tubular cell">tubular cells</a> can also produce glucose. </p><p>Glucose also can be found outside of living organisms in the ambient environment. Glucose concentrations in the atmosphere are detected via collection of samples by aircraft and are known to vary from location to location. For example, glucose concentrations in atmospheric air from inland China range from 0.8 to 20.1 pg/L, whereas east coastal China glucose concentrations range from 10.3 to 142 pg/L.<sup id="cite_ref-90" class="reference"><a href="#cite_note-90"><span class="cite-bracket">&#91;</span>90<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Glucose_degradation">Glucose degradation</h3></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Glucose_metabolism.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/95/Glucose_metabolism.svg/220px-Glucose_metabolism.svg.png" decoding="async" width="220" height="171" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/95/Glucose_metabolism.svg/330px-Glucose_metabolism.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/95/Glucose_metabolism.svg/440px-Glucose_metabolism.svg.png 2x" data-file-width="1390" data-file-height="1080" /></a><figcaption>Glucose metabolism and various forms of it in the process.<div class="paragraphbreak" style="margin-top:0.5em"></div>Glucose-containing compounds and <a href="/wiki/Isomer" title="Isomer">isomeric</a> forms are digested and taken up by the body in the intestines, including <a href="/wiki/Starch" title="Starch">starch</a>, <a href="/wiki/Glycogen" title="Glycogen">glycogen</a>, <a href="/wiki/Disaccharide" title="Disaccharide">disaccharides</a> and <a href="/wiki/Monosaccharide" title="Monosaccharide">monosaccharides</a>.<div class="paragraphbreak" style="margin-top:0.5em"></div>Glucose is stored in mainly the liver and muscles as glycogen. It is distributed and used in tissues as free glucose.</figcaption></figure> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main articles: <a href="/wiki/Glycolysis" title="Glycolysis">Glycolysis</a> and <a href="/wiki/Pentose_phosphate_pathway" title="Pentose phosphate pathway">Pentose phosphate pathway</a></div> <p>In humans, glucose is metabolized by glycolysis<sup id="cite_ref-91" class="reference"><a href="#cite_note-91"><span class="cite-bracket">&#91;</span>91<span class="cite-bracket">&#93;</span></a></sup> and the pentose phosphate pathway.<sup id="cite_ref-Horton_92-0" class="reference"><a href="#cite_note-Horton-92"><span class="cite-bracket">&#91;</span>92<span class="cite-bracket">&#93;</span></a></sup> Glycolysis is used by all living organisms,<sup id="cite_ref-Garrett_66-1" class="reference"><a href="#cite_note-Garrett-66"><span class="cite-bracket">&#91;</span>66<span class="cite-bracket">&#93;</span></a></sup><sup class="reference nowrap"><span title="Page / location: 551">&#58;&#8202;551&#8202;</span></sup><sup id="cite_ref-Hall_93-0" class="reference"><a href="#cite_note-Hall-93"><span class="cite-bracket">&#91;</span>93<span class="cite-bracket">&#93;</span></a></sup> with small variations, and all organisms generate energy from the breakdown of monosaccharides.<sup id="cite_ref-Hall_93-1" class="reference"><a href="#cite_note-Hall-93"><span class="cite-bracket">&#91;</span>93<span class="cite-bracket">&#93;</span></a></sup> In the further course of the metabolism, it can be completely degraded via <a href="/wiki/Oxidative_decarboxylation" title="Oxidative decarboxylation">oxidative decarboxylation</a>, the <a href="/wiki/Citric_acid_cycle" title="Citric acid cycle">citric acid cycle</a> (synonym <i>Krebs cycle</i>) and the <a href="/wiki/Respiratory_chain" class="mw-redirect" title="Respiratory chain">respiratory chain</a> to water and carbon dioxide. If there is not enough oxygen available for this, the glucose degradation in animals occurs anaerobic to lactate via lactic acid fermentation and releases much less energy. Muscular lactate enters the liver through the bloodstream in mammals, where gluconeogenesis occurs (<a href="/wiki/Cori_cycle" title="Cori cycle">Cori cycle</a>). With a high supply of glucose, the metabolite <a href="/wiki/Acetyl-CoA" title="Acetyl-CoA">acetyl-CoA</a> from the Krebs cycle can also be used for <a href="/wiki/Fatty_acid_synthesis" title="Fatty acid synthesis">fatty acid synthesis</a>.<sup id="cite_ref-94" class="reference"><a href="#cite_note-94"><span class="cite-bracket">&#91;</span>94<span class="cite-bracket">&#93;</span></a></sup> Glucose is also used to replenish the body's glycogen stores, which are mainly found in liver and skeletal muscle. These processes are <a href="/wiki/Hormone" title="Hormone">hormonally</a> regulated. </p><p>In other living organisms, other forms of fermentation can occur. The bacterium <i><a href="/wiki/Escherichia_coli" title="Escherichia coli">Escherichia coli</a></i> can grow on nutrient media containing glucose as the sole carbon source.<sup id="cite_ref-Voet_67-3" class="reference"><a href="#cite_note-Voet-67"><span class="cite-bracket">&#91;</span>67<span class="cite-bracket">&#93;</span></a></sup><sup class="reference nowrap"><span title="Page / location: 59">&#58;&#8202;59&#8202;</span></sup> In some bacteria and, in modified form, also in archaea, glucose is degraded via the <a href="/wiki/Entner-Doudoroff_pathway" class="mw-redirect" title="Entner-Doudoroff pathway">Entner-Doudoroff pathway</a>.<sup id="cite_ref-95" class="reference"><a href="#cite_note-95"><span class="cite-bracket">&#91;</span>95<span class="cite-bracket">&#93;</span></a></sup> With Glucose, a mechanism for <a href="/wiki/Gene_regulation" class="mw-redirect" title="Gene regulation">gene regulation</a> was discovered in <i>E. coli</i>, the <a href="/wiki/Catabolite_repression" title="Catabolite repression">catabolite repression</a> (formerly known as <i>glucose effect</i>).<sup id="cite_ref-&#80;MID29330542_96-0" class="reference"><a href="#cite_note-PMID29330542-96"><span class="cite-bracket">&#91;</span>96<span class="cite-bracket">&#93;</span></a></sup> </p><p>Use of glucose as an energy source in cells is by either aerobic respiration, anaerobic respiration, or fermentation.<sup id="cite_ref-sil_97-0" class="reference"><a href="#cite_note-sil-97"><span class="cite-bracket">&#91;</span>97<span class="cite-bracket">&#93;</span></a></sup> The first step of glycolysis is the <a href="/wiki/Phosphorylation" title="Phosphorylation">phosphorylation</a> of glucose by a <a href="/wiki/Hexokinase" title="Hexokinase">hexokinase</a> to form <a href="/wiki/Glucose_6-phosphate" title="Glucose 6-phosphate">glucose 6-phosphate</a>. The main reason for the immediate phosphorylation of glucose is to prevent its diffusion out of the cell as the charged <a href="/wiki/Phosphate" title="Phosphate">phosphate</a> group prevents glucose 6-phosphate from easily crossing the <a href="/wiki/Cell_membrane" title="Cell membrane">cell membrane</a>.<sup id="cite_ref-sil_97-1" class="reference"><a href="#cite_note-sil-97"><span class="cite-bracket">&#91;</span>97<span class="cite-bracket">&#93;</span></a></sup> Furthermore, addition of the high-energy phosphate group <a href="/wiki/Activation#Biochemistry" title="Activation">activates</a> glucose for subsequent breakdown in later steps of glycolysis.<sup id="cite_ref-98" class="reference"><a href="#cite_note-98"><span class="cite-bracket">&#91;</span>98<span class="cite-bracket">&#93;</span></a></sup> </p><p>In anaerobic respiration, one glucose molecule produces a net gain of two ATP molecules (four ATP molecules are produced during glycolysis through substrate-level phosphorylation, but two are required by enzymes used during the process).<sup id="cite_ref-99" class="reference"><a href="#cite_note-99"><span class="cite-bracket">&#91;</span>99<span class="cite-bracket">&#93;</span></a></sup> In aerobic respiration, a molecule of glucose is much more profitable in that a maximum net production of 30 or 32 ATP molecules (depending on the organism) is generated.<sup id="cite_ref-100" class="reference"><a href="#cite_note-100"><span class="cite-bracket">&#91;</span>100<span class="cite-bracket">&#93;</span></a></sup> </p><p><i>Click on genes, proteins and metabolites below to link to respective articles.</i><sup id="cite_ref-WikiPathways_101-0" class="reference"><a href="#cite_note-WikiPathways-101"><span class="cite-bracket">&#91;</span>§ 1<span class="cite-bracket">&#93;</span></a></sup> </p> <div style="overflow:auto;"> <div class="thumb tleft"> <div class="thumbinner" style="width: 377px;"> <div class="thumbimage" style="width: 375px; height: 350px; overflow: hidden;"> <div style="position: relative; top: -25px; left: -95px; width: &#123;&#123;&#123;bSize&#125;&#125;&#125;px"><div class="noresize">[[File:<div class="noresize thumb tnone" style=";"> <div class="thumbinner" style="overflow:hidden;width:1017px;"> <div class="thumbimage" style="overflow:hidden; position:relative; background-color:white;"> <div style=";left:0px; top:0px; width:1015px; position:absolute;"> <figure class="mw-default-size mw-halign-right noresize" typeof="mw:File"><a href="/wiki/Glycolysis#Interactive_pathway_map" title="Go to pathway article"><img alt="GlycolysisGluconeogenesis_WP534" src="//upload.wikimedia.org/wikipedia/commons/a/aa/WP534.png" decoding="async" width="1015" height="1341" class="mw-file-element" data-file-width="1015" data-file-height="1341" usemap="#ImageMap_868cf5ca7e758742" /></a><map name="ImageMap_868cf5ca7e758742"><area href="/wiki/2-Phosphoglyceric_acid" shape="rect" coords="223,823,323,843" alt="go to article" title="go to 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title="go to Entrez" /><area href="/wiki/BRP44" shape="rect" coords="593,1091,673,1111" alt="go to article" title="go to article" /></map><figcaption></figcaption></figure></div> </div> <div class="thumbcaption"></div> </div></div>|alt=Glycolysis and Gluconeogenesis <a rel="nofollow" class="external text" href="http://www.wikipathways.org/index.php/Pathway:WP534">edit</a>]]</div></div> </div> <div class="thumbcaption"> <div class="magnify"><a href="/wiki/File:WP534.png" title="File:WP534.png"> </a></div>Glycolysis and Gluconeogenesis <a rel="nofollow" class="external text" href="http://www.wikipathways.org/index.php/Pathway:WP534">edit</a> </div> </div> </div> <div style="clear:both;" class=""></div><style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap"><ol class="references"> <li id="cite_note-WikiPathways-101"><span class="mw-cite-backlink"><b><a href="#cite_ref-WikiPathways_101-0">^</a></b></span> <span class="reference-text">The interactive pathway map can be edited at WikiPathways: <style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://www.wikipathways.org/index.php/Pathway:WP534">"GlycolysisGluconeogenesis_WP534"</a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=unknown&amp;rft.btitle=GlycolysisGluconeogenesis_WP534&amp;rft_id=http%3A%2F%2Fwww.wikipathways.org%2Findex.php%2FPathway%3AWP534&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AGlucose" class="Z3988"></span></span> </li> </ol></div></div> </div> <p><a href="/wiki/Tumor" class="mw-redirect" title="Tumor">Tumor</a> cells often grow comparatively quickly and consume an above-average amount of glucose by glycolysis,<sup id="cite_ref-102" class="reference"><a href="#cite_note-102"><span class="cite-bracket">&#91;</span>101<span class="cite-bracket">&#93;</span></a></sup> which leads to the formation of lactate, the end product of fermentation in mammals, even in the presence of oxygen. This is called the <a href="/wiki/Warburg_effect_(oncology)" title="Warburg effect (oncology)">Warburg effect</a>. For the increased uptake of glucose in tumors various SGLT and GLUT are overly produced.<sup id="cite_ref-103" class="reference"><a href="#cite_note-103"><span class="cite-bracket">&#91;</span>102<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-104" class="reference"><a href="#cite_note-104"><span class="cite-bracket">&#91;</span>103<span class="cite-bracket">&#93;</span></a></sup> </p><p>In <a href="/wiki/Yeast" title="Yeast">yeast</a>, ethanol is fermented at high glucose concentrations, even in the presence of oxygen (which normally leads to respiration rather than fermentation). This is called the <a href="/wiki/Crabtree_effect" title="Crabtree effect">Crabtree effect</a>. </p><p>Glucose can also degrade to form carbon dioxide through abiotic means. This has been demonstrated to occur experimentally via oxidation and hydrolysis at 22&#160;°C and a pH of 2.5.<sup id="cite_ref-105" class="reference"><a href="#cite_note-105"><span class="cite-bracket">&#91;</span>104<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Energy_source">Energy source</h3></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Glucose_catabolism_intermediates_de.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/cf/Glucose_catabolism_intermediates_de.png/260px-Glucose_catabolism_intermediates_de.png" decoding="async" width="260" height="391" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/cf/Glucose_catabolism_intermediates_de.png/390px-Glucose_catabolism_intermediates_de.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/cf/Glucose_catabolism_intermediates_de.png/520px-Glucose_catabolism_intermediates_de.png 2x" data-file-width="1564" data-file-height="2354" /></a><figcaption>Diagram showing the possible intermediates in glucose degradation; Metabolic pathways orange: glycolysis, green: Entner-Doudoroff pathway, phosphorylating, yellow: Entner-Doudoroff pathway, non-phosphorylating</figcaption></figure> <p>Glucose is a ubiquitous fuel in <a href="/wiki/Biology" title="Biology">biology</a>. It is used as an energy source in organisms, from bacteria to humans, through either <a href="/wiki/Aerobic_respiration" class="mw-redirect" title="Aerobic respiration">aerobic respiration</a>, <a href="/wiki/Anaerobic_respiration" title="Anaerobic respiration">anaerobic respiration</a> (in bacteria), or <a href="/wiki/Fermentation_(biochemistry)" class="mw-redirect" title="Fermentation (biochemistry)">fermentation</a>. Glucose is the human body's key source of energy, through aerobic respiration, providing about 3.75&#160;<a href="/wiki/Kilocalorie" class="mw-redirect" title="Kilocalorie">kilocalories</a> (16&#160;<a href="/wiki/Kilojoule" class="mw-redirect" title="Kilojoule">kilojoules</a>) of <a href="/wiki/Food_energy" title="Food energy">food energy</a> per gram.<sup id="cite_ref-106" class="reference"><a href="#cite_note-106"><span class="cite-bracket">&#91;</span>105<span class="cite-bracket">&#93;</span></a></sup> Breakdown of carbohydrates (e.g., starch) yields mono- and <a href="/wiki/Disaccharide" title="Disaccharide">disaccharides</a>, most of which is glucose. Through <a href="/wiki/Glycolysis" title="Glycolysis">glycolysis</a> and later in the reactions of the <a href="/wiki/Citric_acid_cycle" title="Citric acid cycle">citric acid cycle</a> and <a href="/wiki/Oxidative_phosphorylation" title="Oxidative phosphorylation">oxidative phosphorylation</a>, glucose is <a href="/wiki/Oxidize" class="mw-redirect" title="Oxidize">oxidized</a> to eventually form <a href="/wiki/Carbon_dioxide" title="Carbon dioxide">carbon dioxide</a> and water, yielding energy mostly in the form of <a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate">adenosine triphosphate</a> (ATP). The insulin reaction, and other mechanisms, regulate the concentration of glucose in the blood. The physiological caloric value of glucose, depending on the source, is 16.2 kilojoules per gram<sup id="cite_ref-Schwedt_107-0" class="reference"><a href="#cite_note-Schwedt-107"><span class="cite-bracket">&#91;</span>106<span class="cite-bracket">&#93;</span></a></sup> or 15.7 kJ/g (3.74 kcal/g).<sup id="cite_ref-108" class="reference"><a href="#cite_note-108"><span class="cite-bracket">&#91;</span>107<span class="cite-bracket">&#93;</span></a></sup> The high availability of carbohydrates from plant biomass has led to a variety of methods during evolution, especially in microorganisms, to utilize glucose for energy and carbon storage. Differences exist in which end product can no longer be used for energy production. The presence of individual genes, and their gene products, the enzymes, determine which reactions are possible. The metabolic pathway of glycolysis is used by almost all living beings. An essential difference in the use of glycolysis is the recovery of <a href="/wiki/NADPH" class="mw-redirect" title="NADPH">NADPH</a> as a reductant for <a href="/wiki/Anabolism" title="Anabolism">anabolism</a> that would otherwise have to be generated indirectly.<sup id="cite_ref-109" class="reference"><a href="#cite_note-109"><span class="cite-bracket">&#91;</span>108<span class="cite-bracket">&#93;</span></a></sup> </p><p>Glucose and oxygen supply almost all the energy for the <a href="/wiki/Brain" title="Brain">brain</a>,<sup id="cite_ref-110" class="reference"><a href="#cite_note-110"><span class="cite-bracket">&#91;</span>109<span class="cite-bracket">&#93;</span></a></sup> so its availability influences <a href="/wiki/Psychological" class="mw-redirect" title="Psychological">psychological</a> processes. When <a href="/wiki/Hypoglycaemia" class="mw-redirect" title="Hypoglycaemia">glucose is low</a>, psychological processes requiring mental effort (e.g., <a href="/wiki/Self-control" title="Self-control">self-control</a>, effortful decision-making) are impaired.<sup id="cite_ref-111" class="reference"><a href="#cite_note-111"><span class="cite-bracket">&#91;</span>110<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-112" class="reference"><a href="#cite_note-112"><span class="cite-bracket">&#91;</span>111<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-113" class="reference"><a href="#cite_note-113"><span class="cite-bracket">&#91;</span>112<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-114" class="reference"><a href="#cite_note-114"><span class="cite-bracket">&#91;</span>113<span class="cite-bracket">&#93;</span></a></sup> In the brain, which is dependent on glucose and oxygen as the major source of energy, the glucose concentration is usually 4 to 6&#160;mM (5&#160;mM equals 90&#160;mg/dL),<sup id="cite_ref-Satyanarayana_71-2" class="reference"><a href="#cite_note-Satyanarayana-71"><span class="cite-bracket">&#91;</span>71<span class="cite-bracket">&#93;</span></a></sup> but decreases to 2 to 3&#160;mM when fasting.<sup id="cite_ref-Dwyer_115-0" class="reference"><a href="#cite_note-Dwyer-115"><span class="cite-bracket">&#91;</span>114<span class="cite-bracket">&#93;</span></a></sup> <a href="/wiki/Confusion" title="Confusion">Confusion</a> occurs below 1&#160;mM and <a href="/wiki/Coma" title="Coma">coma</a> at lower levels.<sup id="cite_ref-Dwyer_115-1" class="reference"><a href="#cite_note-Dwyer-115"><span class="cite-bracket">&#91;</span>114<span class="cite-bracket">&#93;</span></a></sup> </p><p>The glucose in the blood is called <a href="/wiki/Blood_sugar" class="mw-redirect" title="Blood sugar">blood sugar</a>. Blood sugar levels are regulated by glucose-binding nerve cells in the <a href="/wiki/Hypothalamus" title="Hypothalamus">hypothalamus</a>.<sup id="cite_ref-Koekkoek_116-0" class="reference"><a href="#cite_note-Koekkoek-116"><span class="cite-bracket">&#91;</span>115<span class="cite-bracket">&#93;</span></a></sup> In addition, glucose in the brain binds to glucose receptors of the <a href="/wiki/Reward_system" title="Reward system">reward system</a> in the <a href="/wiki/Nucleus_accumbens" title="Nucleus accumbens">nucleus accumbens</a>.<sup id="cite_ref-Koekkoek_116-1" class="reference"><a href="#cite_note-Koekkoek-116"><span class="cite-bracket">&#91;</span>115<span class="cite-bracket">&#93;</span></a></sup> The binding of glucose to the sweet receptor on the tongue induces a release of various hormones of energy metabolism, either through glucose or through other sugars, leading to an increased cellular uptake and lower blood sugar levels.<sup id="cite_ref-Tucker_117-0" class="reference"><a href="#cite_note-Tucker-117"><span class="cite-bracket">&#91;</span>116<span class="cite-bracket">&#93;</span></a></sup> <a href="/wiki/Artificial_sweetener" class="mw-redirect" title="Artificial sweetener">Artificial sweeteners</a> do not lower blood sugar levels.<sup id="cite_ref-Tucker_117-1" class="reference"><a href="#cite_note-Tucker-117"><span class="cite-bracket">&#91;</span>116<span class="cite-bracket">&#93;</span></a></sup> </p><p>The blood sugar content of a healthy person in the short-time fasting state, e.g. after overnight fasting, is about 70 to 100&#160;mg/dL of blood (4 to 5.5&#160;mM). In <a href="/wiki/Blood_plasma" title="Blood plasma">blood plasma</a>, the measured values are about 10–15% higher. In addition, the values in the <a href="/wiki/Artery" title="Artery">arterial</a> blood are higher than the concentrations in the <a href="/wiki/Vein" title="Vein">venous</a> blood since glucose is absorbed into the tissue during the passage of the <a href="/wiki/Capillary_bed" class="mw-redirect" title="Capillary bed">capillary bed</a>. Also in the capillary blood, which is often used for blood sugar determination, the values are sometimes higher than in the venous blood. The glucose content of the blood is regulated by the hormones <a href="/wiki/Insulin" title="Insulin">insulin</a>, <a href="/wiki/Incretin" title="Incretin">incretin</a> and <a href="/wiki/Glucagon" title="Glucagon">glucagon</a>.<sup id="cite_ref-Koekkoek_116-2" class="reference"><a href="#cite_note-Koekkoek-116"><span class="cite-bracket">&#91;</span>115<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-118" class="reference"><a href="#cite_note-118"><span class="cite-bracket">&#91;</span>117<span class="cite-bracket">&#93;</span></a></sup> Insulin lowers the glucose level, glucagon increases it.<sup id="cite_ref-Satyanarayana_71-3" class="reference"><a href="#cite_note-Satyanarayana-71"><span class="cite-bracket">&#91;</span>71<span class="cite-bracket">&#93;</span></a></sup> Furthermore, the hormones <a href="/wiki/Adrenaline" title="Adrenaline">adrenaline</a>, <a href="/wiki/Thyroxine" class="mw-redirect" title="Thyroxine">thyroxine</a>, <a href="/wiki/Glucocorticoid" title="Glucocorticoid">glucocorticoids</a>, <a href="/wiki/Somatotropin" class="mw-redirect" title="Somatotropin">somatotropin</a> and <a href="/wiki/Adrenocorticotropin" class="mw-redirect" title="Adrenocorticotropin">adrenocorticotropin</a> lead to an increase in the glucose level.<sup id="cite_ref-Satyanarayana_71-4" class="reference"><a href="#cite_note-Satyanarayana-71"><span class="cite-bracket">&#91;</span>71<span class="cite-bracket">&#93;</span></a></sup> There is also a hormone-independent regulation, which is referred to as <a href="/w/index.php?title=Glucose_autoregulation&amp;action=edit&amp;redlink=1" class="new" title="Glucose autoregulation (page does not exist)">glucose autoregulation</a>.<sup id="cite_ref-119" class="reference"><a href="#cite_note-119"><span class="cite-bracket">&#91;</span>118<span class="cite-bracket">&#93;</span></a></sup> After food intake the blood sugar concentration increases. Values over 180&#160;mg/dL in venous whole blood are pathological and are termed <a href="/wiki/Hyperglycemia" title="Hyperglycemia">hyperglycemia</a>, values below 40&#160;mg/dL are termed <a href="/wiki/Hypoglycaemia" class="mw-redirect" title="Hypoglycaemia">hypoglycaemia</a>.<sup id="cite_ref-120" class="reference"><a href="#cite_note-120"><span class="cite-bracket">&#91;</span>119<span class="cite-bracket">&#93;</span></a></sup> When needed, glucose is released into the bloodstream by glucose-6-phosphatase from glucose-6-phosphate originating from liver and kidney glycogen, thereby regulating the <a href="/wiki/Homeostasis" title="Homeostasis">homeostasis</a> of blood glucose concentration.<sup id="cite_ref-Szablewski_88-1" class="reference"><a href="#cite_note-Szablewski-88"><span class="cite-bracket">&#91;</span>88<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-Löffler/Petrides_195_70-2" class="reference"><a href="#cite_note-Löffler/Petrides_195-70"><span class="cite-bracket">&#91;</span>70<span class="cite-bracket">&#93;</span></a></sup> In <a href="/wiki/Ruminant" title="Ruminant">ruminants</a>, the blood glucose concentration is lower (60&#160;mg/dL in <a href="/wiki/Cattle" title="Cattle">cattle</a> and 40&#160;mg/dL in <a href="/wiki/Sheep" title="Sheep">sheep</a>), because the carbohydrates are converted more by their gut microbiota into <a href="/wiki/Short-chain_fatty_acid" title="Short-chain fatty acid">short-chain fatty acids</a>.<sup id="cite_ref-Harper_121-0" class="reference"><a href="#cite_note-Harper-121"><span class="cite-bracket">&#91;</span>120<span class="cite-bracket">&#93;</span></a></sup> </p><p>Some glucose is converted to <a href="/wiki/Lactic_acid" title="Lactic acid">lactic acid</a> by <a href="/wiki/Astrocyte" title="Astrocyte">astrocytes</a>, which is then utilized as an energy source by <a href="/wiki/Brain_cells" class="mw-redirect" title="Brain cells">brain cells</a>; some glucose is used by intestinal cells and <a href="/wiki/Red_blood_cell" title="Red blood cell">red blood cells</a>, while the rest reaches the <a href="/wiki/Liver" title="Liver">liver</a>, <a href="/wiki/Adipose_tissue" title="Adipose tissue">adipose tissue</a> and <a href="/wiki/Muscle" title="Muscle">muscle</a> cells, where it is absorbed and stored as glycogen (under the influence of <a href="/wiki/Insulin" title="Insulin">insulin</a>). Liver cell glycogen can be converted to glucose and returned to the blood when insulin is low or absent; muscle cell glycogen is not returned to the blood because of a lack of enzymes. In <a href="/wiki/Adipocyte" title="Adipocyte">fat cells</a>, glucose is used to power reactions that synthesize some <a href="/wiki/Fat" title="Fat">fat</a> types and have other purposes. Glycogen is the body's "glucose energy storage" mechanism, because it is much more "space efficient" and less reactive than glucose itself. </p><p>As a result of its importance in human health, glucose is an analyte in <a href="/wiki/Glucose_test" title="Glucose test">glucose tests</a> that are common medical <a href="/wiki/Blood_test" title="Blood test">blood tests</a>.<sup id="cite_ref-122" class="reference"><a href="#cite_note-122"><span class="cite-bracket">&#91;</span>121<span class="cite-bracket">&#93;</span></a></sup> Eating or fasting prior to taking a blood sample has an effect on analyses for glucose in the blood; a high fasting glucose blood sugar level may be a sign of <a href="/wiki/Prediabetes" title="Prediabetes">prediabetes</a> or <a href="/wiki/Diabetes_mellitus" class="mw-redirect" title="Diabetes mellitus">diabetes mellitus</a>.<sup id="cite_ref-123" class="reference"><a href="#cite_note-123"><span class="cite-bracket">&#91;</span>122<span class="cite-bracket">&#93;</span></a></sup> </p><p>The <a href="/wiki/Glycemic_index" title="Glycemic index">glycemic index</a> is an indicator of the speed of resorption and conversion to blood glucose levels from ingested carbohydrates, measured as the <a href="/wiki/Area_under_a_curve" class="mw-redirect" title="Area under a curve">area under the curve</a> of blood glucose levels after consumption in comparison to glucose (glucose is defined as 100).<sup id="cite_ref-Harvey_366_124-0" class="reference"><a href="#cite_note-Harvey_366-124"><span class="cite-bracket">&#91;</span>123<span class="cite-bracket">&#93;</span></a></sup> The clinical importance of the glycemic index is controversial,<sup id="cite_ref-Harvey_366_124-1" class="reference"><a href="#cite_note-Harvey_366-124"><span class="cite-bracket">&#91;</span>123<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-Satyarayana_508_125-0" class="reference"><a href="#cite_note-Satyarayana_508-125"><span class="cite-bracket">&#91;</span>124<span class="cite-bracket">&#93;</span></a></sup> as foods with high fat contents slow the resorption of carbohydrates and lower the glycemic index, e.g. ice cream.<sup id="cite_ref-Satyarayana_508_125-1" class="reference"><a href="#cite_note-Satyarayana_508-125"><span class="cite-bracket">&#91;</span>124<span class="cite-bracket">&#93;</span></a></sup> An alternative indicator is the <a href="/wiki/Insulin_index" title="Insulin index">insulin index</a>,<sup id="cite_ref-126" class="reference"><a href="#cite_note-126"><span class="cite-bracket">&#91;</span>125<span class="cite-bracket">&#93;</span></a></sup> measured as the impact of carbohydrate consumption on the blood insulin levels. The <a href="/wiki/Glycemic_load" title="Glycemic load">glycemic load</a> is an indicator for the amount of glucose added to blood glucose levels after consumption, based on the glycemic index and the amount of consumed food. </p> <div class="mw-heading mw-heading3"><h3 id="Precursor">Precursor</h3></div> <p>Organisms use glucose as a precursor for the synthesis of several important substances. Starch, <a href="/wiki/Cellulose" title="Cellulose">cellulose</a>, and glycogen ("animal starch") are common glucose <a href="/wiki/Polymer" title="Polymer">polymers</a> (polysaccharides). Some of these polymers (starch or glycogen) serve as energy stores, while others (cellulose and <a href="/wiki/Chitin" title="Chitin">chitin</a>, which is made from a derivative of glucose) have structural roles. Oligosaccharides of glucose combined with other sugars serve as important energy stores. These include lactose, the predominant sugar in milk, which is a glucose-galactose disaccharide, and sucrose, another disaccharide which is composed of glucose and fructose. Glucose is also added onto certain proteins and <a href="/wiki/Lipid" title="Lipid">lipids</a> in a process called <a href="/wiki/Glycosylation" title="Glycosylation">glycosylation</a>. This is often critical for their functioning. The enzymes that join glucose to other molecules usually use <a href="/wiki/Phosphorylation" title="Phosphorylation">phosphorylated</a> glucose to power the formation of the new bond by coupling it with the breaking of the glucose-phosphate bond. </p><p>Other than its direct use as a monomer, glucose can be broken down to synthesize a wide variety of other biomolecules. This is important, as glucose serves both as a primary store of energy and as a source of organic carbon. Glucose can be broken down and converted into lipids. It is also a precursor for the synthesis of other important molecules such as <a href="/wiki/Vitamin_C" title="Vitamin C">vitamin C</a> (ascorbic acid). In living organisms, glucose is converted to several other chemical compounds that are the starting material for various <a href="/wiki/Metabolic_pathway" title="Metabolic pathway">metabolic pathways</a>. Among them, all other monosaccharides<sup id="cite_ref-Löffler/Petrides_27_127-0" class="reference"><a href="#cite_note-Löffler/Petrides_27-127"><span class="cite-bracket">&#91;</span>126<span class="cite-bracket">&#93;</span></a></sup> such as fructose (via the <a href="/wiki/Polyol_pathway" title="Polyol pathway">polyol pathway</a>),<sup id="cite_ref-Löffler/Petrides_199_79-5" class="reference"><a href="#cite_note-Löffler/Petrides_199-79"><span class="cite-bracket">&#91;</span>79<span class="cite-bracket">&#93;</span></a></sup> mannose (the epimer of glucose at position 2), galactose (the epimer at position 4), fucose, various <a href="/wiki/Uronic_acids" class="mw-redirect" title="Uronic acids">uronic acids</a> and the <a href="/wiki/Amino_sugar" title="Amino sugar">amino sugars</a> are produced from glucose.<sup id="cite_ref-Löffler/Petrides_214_81-1" class="reference"><a href="#cite_note-Löffler/Petrides_214-81"><span class="cite-bracket">&#91;</span>81<span class="cite-bracket">&#93;</span></a></sup> In addition to the phosphorylation to glucose-6-phosphate, which is part of the glycolysis, glucose can be oxidized during its degradation to <a href="/w/index.php?title=Glucono-1,5-lactone&amp;action=edit&amp;redlink=1" class="new" title="Glucono-1,5-lactone (page does not exist)">glucono-1,5-lactone</a>. Glucose is used in some bacteria as a building block in the <a href="/wiki/Trehalose" title="Trehalose">trehalose</a> or the <a href="/wiki/Dextran" title="Dextran">dextran</a> biosynthesis and in animals as a building block of glycogen. Glucose can also be converted from bacterial <a href="/wiki/Xylose_isomerase" title="Xylose isomerase">xylose isomerase</a> to fructose. In addition, glucose <a href="/wiki/Metabolite" title="Metabolite">metabolites</a> produce all nonessential amino acids, <a href="/wiki/Sugar_alcohol" title="Sugar alcohol">sugar alcohols</a> such as <a href="/wiki/Mannitol" title="Mannitol">mannitol</a> and <a href="/wiki/Sorbitol" title="Sorbitol">sorbitol</a>, <a href="/wiki/Fatty_acid" title="Fatty acid">fatty acids</a>, <a href="/wiki/Cholesterol" title="Cholesterol">cholesterol</a> and <a href="/wiki/Nucleic_acid" title="Nucleic acid">nucleic acids</a>.<sup id="cite_ref-Löffler/Petrides_27_127-1" class="reference"><a href="#cite_note-Löffler/Petrides_27-127"><span class="cite-bracket">&#91;</span>126<span class="cite-bracket">&#93;</span></a></sup> Finally, glucose is used as a building block in the <a href="/wiki/Glycosylation" title="Glycosylation">glycosylation</a> of proteins to <a href="/wiki/Glycoprotein" title="Glycoprotein">glycoproteins</a>, <a href="/wiki/Glycolipid" title="Glycolipid">glycolipids</a>, <a href="/wiki/Peptidoglycan" title="Peptidoglycan">peptidoglycans</a>, <a href="/wiki/Glycoside" title="Glycoside">glycosides</a> and other substances (catalyzed by <a href="/wiki/Glycosyltransferase" title="Glycosyltransferase">glycosyltransferases</a>) and can be cleaved from them by <a href="/wiki/Glycosidase" class="mw-redirect" title="Glycosidase">glycosidases</a>. </p> <div class="mw-heading mw-heading2"><h2 id="Pathology">Pathology</h2></div> <div class="mw-heading mw-heading3"><h3 id="Diabetes">Diabetes</h3></div> <p><a href="/wiki/Diabetes" title="Diabetes">Diabetes</a> is a metabolic disorder where the body is unable to regulate <a href="/wiki/Blood_sugar" class="mw-redirect" title="Blood sugar">levels of glucose in the blood</a> either because of a lack of insulin in the body or the failure, by cells in the body, to respond properly to insulin. Each of these situations can be caused by persistently high elevations of blood glucose levels, through pancreatic burnout and <a href="/wiki/Insulin_resistance" title="Insulin resistance">insulin resistance</a>. The <a href="/wiki/Pancreas" title="Pancreas">pancreas</a> is the organ responsible for the secretion of the hormones insulin and glucagon.<sup id="cite_ref-128" class="reference"><a href="#cite_note-128"><span class="cite-bracket">&#91;</span>127<span class="cite-bracket">&#93;</span></a></sup> Insulin is a hormone that regulates glucose levels, allowing the body's cells to absorb and use glucose. Without it, glucose cannot enter the cell and therefore cannot be used as fuel for the body's functions.<sup id="cite_ref-129" class="reference"><a href="#cite_note-129"><span class="cite-bracket">&#91;</span>128<span class="cite-bracket">&#93;</span></a></sup> If the pancreas is exposed to persistently high elevations of blood glucose levels, the <a href="/wiki/Beta_cell" title="Beta cell">insulin-producing cells</a> in the pancreas could be damaged, causing a lack of insulin in the body. Insulin resistance occurs when the pancreas tries to produce more and more insulin in response to persistently elevated blood glucose levels. Eventually, the rest of the body becomes resistant to the insulin that the pancreas is producing, thereby requiring more insulin to achieve the same blood glucose-lowering effect, and forcing the pancreas to produce even more insulin to compete with the resistance. This negative spiral contributes to pancreatic burnout, and the disease progression of diabetes. </p><p>To monitor the body's response to blood glucose-lowering therapy, glucose levels can be measured. <a href="/wiki/Blood_glucose_monitoring" title="Blood glucose monitoring">Blood glucose monitoring</a> can be performed by multiple methods, such as the fasting glucose test which measures the level of glucose in the blood after 8 hours of fasting. Another test is the 2-hour glucose tolerance test (GTT)&#160;&#8211;&#32;for this test, the person has a fasting glucose test done, then drinks a 75-gram glucose drink and is retested. This test measures the ability of the person's body to process glucose. Over time the blood glucose levels should decrease as insulin allows it to be taken up by cells and exit the blood stream. </p> <div class="mw-heading mw-heading3"><h3 id="Hypoglycemia_management">Hypoglycemia management</h3></div> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Solu%C5%A3ie_glucoz%C4%83_5%25.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/53/Solu%C5%A3ie_glucoz%C4%83_5%25.jpg/220px-Solu%C5%A3ie_glucoz%C4%83_5%25.jpg" decoding="async" width="220" height="165" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/53/Solu%C5%A3ie_glucoz%C4%83_5%25.jpg/330px-Solu%C5%A3ie_glucoz%C4%83_5%25.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/53/Solu%C5%A3ie_glucoz%C4%83_5%25.jpg/440px-Solu%C5%A3ie_glucoz%C4%83_5%25.jpg 2x" data-file-width="3648" data-file-height="2736" /></a><figcaption>Glucose, 5% solution for <a href="/wiki/Infusion_therapy" title="Infusion therapy">infusions</a></figcaption></figure><p> Individuals with diabetes or other conditions that result in <a href="/wiki/Hypoglycemia" title="Hypoglycemia">low blood sugar</a> often carry small amounts of sugar in various forms. One sugar commonly used is glucose, often in the form of glucose tablets (glucose pressed into a tablet shape sometimes with one or more other ingredients as a binder), <a href="/wiki/Hard_candy" title="Hard candy">hard candy</a>, or <a href="/wiki/Sugar_packet" title="Sugar packet">sugar packet</a>.</p><div style="clear:both;" class=""></div> <div class="mw-heading mw-heading2"><h2 id="Sources">Sources</h2></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Glucose_2.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/33/Glucose_2.jpg/220px-Glucose_2.jpg" decoding="async" width="220" height="165" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/33/Glucose_2.jpg/330px-Glucose_2.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/33/Glucose_2.jpg/440px-Glucose_2.jpg 2x" data-file-width="1000" data-file-height="750" /></a><figcaption>a source of glucose</figcaption></figure> <p>Most dietary carbohydrates contain glucose, either as their only building block (as in the polysaccharides starch and glycogen), or together with another monosaccharide (as in the hetero-polysaccharides sucrose and lactose).<sup id="cite_ref-130" class="reference"><a href="#cite_note-130"><span class="cite-bracket">&#91;</span>129<span class="cite-bracket">&#93;</span></a></sup> Unbound glucose is one of the main ingredients of honey. Glucose is extremely abundant and has been isolated from a variety of natural sources across the world, including male cones of the coniferous tree <i>Wollemia nobilis</i> in Rome,<sup id="cite_ref-131" class="reference"><a href="#cite_note-131"><span class="cite-bracket">&#91;</span>130<span class="cite-bracket">&#93;</span></a></sup> the roots of <i>Ilex asprella</i> plants in China,<sup id="cite_ref-132" class="reference"><a href="#cite_note-132"><span class="cite-bracket">&#91;</span>131<span class="cite-bracket">&#93;</span></a></sup> and straws from rice in California.<sup id="cite_ref-133" class="reference"><a href="#cite_note-133"><span class="cite-bracket">&#91;</span>132<span class="cite-bracket">&#93;</span></a></sup> </p> <table class="wikitable sortable" style="text-align:center; margin:auto"> <caption>Sugar content of selected common plant foods (in grams per 100&#160;g)<sup id="cite_ref-www.nal.usda.gov_134-0" class="reference"><a href="#cite_note-www.nal.usda.gov-134"><span class="cite-bracket">&#91;</span>133<span class="cite-bracket">&#93;</span></a></sup> </caption> <tbody><tr> <th>Food <br />item </th> <th>Carbohydrate, <br />total,<sup id="cite_ref-135" class="reference"><a href="#cite_note-135"><span class="cite-bracket">&#91;</span>a<span class="cite-bracket">&#93;</span></a></sup> including <br /><a href="/wiki/Dietary_fiber" title="Dietary fiber">dietary fiber</a> </th> <th>Total <br />sugars </th> <th>Free <br />fructose </th> <th>Free <br />glucose </th> <th>Sucrose </th> <th>Ratio of <br />fructose/<br />glucose </th> <th>Sucrose as <br />proportion of <br />total sugars (%) </th></tr> <tr> <th colspan="8" style="text-align:left">Fruits </th></tr> <tr> <td style="text-align:left;"><a href="/wiki/Apple" title="Apple">Apple</a></td> <td>13.8</td> <td>10.4</td> <td>5.9</td> <td>2.4</td> <td>2.1</td> <td>2.0</td> <td>19.9 </td></tr> <tr> <td style="text-align:left;"><a href="/wiki/Apricot" title="Apricot">Apricot</a></td> <td>11.1</td> <td>9.2</td> <td>0.9</td> <td>2.4</td> <td>5.9</td> <td>0.7</td> <td>63.5 </td></tr> <tr> <td style="text-align:left;"><a href="/wiki/Banana" title="Banana">Banana</a></td> <td>22.8</td> <td>12.2</td> <td>4.9</td> <td>5.0</td> <td>2.4</td> <td>1.0</td> <td>20.0 </td></tr> <tr> <td style="text-align:left;"><a href="/wiki/Ficus" title="Ficus">Fig</a>, dried</td> <td>63.9</td> <td>47.9</td> <td>22.9</td> <td>24.8</td> <td>0.9</td> <td>0.93</td> <td>0.15 </td></tr> <tr> <td style="text-align:left;"><a href="/wiki/Grape" title="Grape">Grapes</a></td> <td>18.1</td> <td>15.5</td> <td>8.1</td> <td>7.2</td> <td>0.2</td> <td>1.1</td> <td>1 </td></tr> <tr> <td style="text-align:left;"><a href="/wiki/Navel_orange" title="Navel orange">Navel orange</a></td> <td>12.5</td> <td>8.5</td> <td>2.25</td> <td>2.0</td> <td>4.3</td> <td>1.1</td> <td>50.4 </td></tr> <tr> <td style="text-align:left;"><a href="/wiki/Peach" title="Peach">Peach</a></td> <td>9.5</td> <td>8.4</td> <td>1.5</td> <td>2.0</td> <td>4.8</td> <td>0.9</td> <td>56.7 </td></tr> <tr> <td style="text-align:left;"><a href="/wiki/Pear" title="Pear">Pear</a></td> <td>15.5</td> <td>9.8</td> <td>6.2</td> <td>2.8</td> <td>0.8</td> <td>2.1</td> <td>8.0 </td></tr> <tr> <td style="text-align:left;"><a href="/wiki/Pineapple" title="Pineapple">Pineapple</a></td> <td>13.1</td> <td>9.9</td> <td>2.1</td> <td>1.7</td> <td>6.0</td> <td>1.1</td> <td>60.8 </td></tr> <tr> <td style="text-align:left;"><a href="/wiki/Plum" title="Plum">Plum</a></td> <td>11.4</td> <td>9.9</td> <td>3.1</td> <td>5.1</td> <td>1.6</td> <td>0.66</td> <td>16.2 </td></tr> <tr> <th colspan="8" style="text-align:left">Vegetables </th></tr> <tr> <td style="text-align:left;"><a href="/wiki/Beet" class="mw-redirect" title="Beet">Beet</a>, red</td> <td>9.6</td> <td>6.8</td> <td>0.1</td> <td>0.1</td> <td>6.5</td> <td>1.0</td> <td>96.2 </td></tr> <tr> <td style="text-align:left;"><a href="/wiki/Carrot" title="Carrot">Carrot</a></td> <td>9.6</td> <td>4.7</td> <td>0.6</td> <td>0.6</td> <td>3.6</td> <td>1.0</td> <td>77 </td></tr> <tr> <td style="text-align:left;"><a href="/wiki/Chili_pepper" title="Chili pepper">Red pepper</a>, sweet</td> <td>6.0</td> <td>4.2</td> <td>2.3</td> <td>1.9</td> <td>0.0</td> <td>1.2</td> <td>0.0 </td></tr> <tr> <td style="text-align:left;"><a href="/wiki/Onion" title="Onion">Onion</a>, sweet</td> <td>7.6</td> <td>5.0</td> <td>2.0</td> <td>2.3</td> <td>0.7</td> <td>0.9</td> <td>14.3 </td></tr> <tr> <td style="text-align:left;"><a href="/wiki/Sweet_potato" title="Sweet potato">Sweet potato</a></td> <td>20.1</td> <td>4.2</td> <td>0.7</td> <td>1.0</td> <td>2.5</td> <td>0.9</td> <td>60.3 </td></tr> <tr> <td style="text-align:left;"><a href="/wiki/Yam_(vegetable)" title="Yam (vegetable)">Yam</a></td> <td>27.9</td> <td>0.5</td> <td data-sort-value="" style="background: var(--background-color-interactive, #ececec); color: var(--color-base, inherit); vertical-align: middle; text-align: center;" class="table-na">Traces</td> <td data-sort-value="" style="background: var(--background-color-interactive, #ececec); color: var(--color-base, inherit); vertical-align: middle; text-align: center;" class="table-na">Traces</td> <td data-sort-value="" style="background: var(--background-color-interactive, #ececec); color: var(--color-base, inherit); vertical-align: middle; text-align: center;" class="table-na">Traces</td> <td data-sort-value="" style="background: var(--background-color-interactive, #ececec); color: var(--color-base, inherit); vertical-align: middle; text-align: center;" class="table-na">—</td> <td data-sort-value="" style="background: var(--background-color-interactive, #ececec); color: var(--color-base, inherit); vertical-align: middle; text-align: center;" class="table-na">Traces </td></tr> <tr> <td style="text-align:left;"><a href="/wiki/Sugar_cane" class="mw-redirect" title="Sugar cane">Sugar cane</a></td> <td></td> <td>13–18</td> <td>0.2–1.0</td> <td>0.2–1.0</td> <td>11–16</td> <td>1.0</td> <td>high </td></tr> <tr> <td style="text-align:left;"><a href="/wiki/Sugar_beet" title="Sugar beet">Sugar beet</a></td> <td></td> <td>17–18</td> <td>0.1–0.5</td> <td>0.1–0.5</td> <td>16–17</td> <td>1.0</td> <td>high </td></tr> <tr> <th colspan="8" style="text-align:left">Grains </th></tr> <tr> <td style="text-align:left;"><a href="/wiki/Maize" title="Maize">Corn</a>, sweet</td> <td>19.0</td> <td>6.2</td> <td>1.9</td> <td>3.4</td> <td>0.9</td> <td>0.61</td> <td>15.0 </td></tr></tbody></table> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239543626"><div class="reflist reflist-lower-alpha"> <div class="mw-references-wrap"><ol class="references"> <li id="cite_note-135"><span class="mw-cite-backlink"><b><a href="#cite_ref-135">^</a></b></span> <span class="reference-text">The carbohydrate value is calculated in the USDA database and does not always correspond to the sum of the sugars, the starch, and the "dietary fiber".</span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="Commercial_production">Commercial production</h2></div> <p>Glucose is produced industrially from starch by <a href="/wiki/Enzyme" title="Enzyme">enzymatic</a> <a href="/wiki/Hydrolysis" title="Hydrolysis">hydrolysis</a> using <a href="/wiki/Glucose_amylase" class="mw-redirect" title="Glucose amylase">glucose amylase</a> or by the use of <a href="/wiki/Acids" class="mw-redirect" title="Acids">acids</a>. Enzymatic hydrolysis has largely displaced acid-catalyzed hydrolysis reactions.<sup id="cite_ref-Fellows_136-0" class="reference"><a href="#cite_note-Fellows-136"><span class="cite-bracket">&#91;</span>134<span class="cite-bracket">&#93;</span></a></sup> The result is glucose syrup (enzymatically with more than 90% glucose in the dry matter)<sup id="cite_ref-Fellows_136-1" class="reference"><a href="#cite_note-Fellows-136"><span class="cite-bracket">&#91;</span>134<span class="cite-bracket">&#93;</span></a></sup> with an annual worldwide production volume of 20 million tonnes (as of 2011).<sup id="cite_ref-Ullmann_48_137-0" class="reference"><a href="#cite_note-Ullmann_48-137"><span class="cite-bracket">&#91;</span>135<span class="cite-bracket">&#93;</span></a></sup> This is the reason for the former common name "starch sugar". The amylases most often come from <i><a href="/wiki/Bacillus_licheniformis" title="Bacillus licheniformis">Bacillus licheniformis</a></i><sup id="cite_ref-ResSoc_138-0" class="reference"><a href="#cite_note-ResSoc-138"><span class="cite-bracket">&#91;</span>136<span class="cite-bracket">&#93;</span></a></sup> or <i><a href="/wiki/Bacillus_subtilis" title="Bacillus subtilis">Bacillus subtilis</a></i> (strain MN-385),<sup id="cite_ref-ResSoc_138-1" class="reference"><a href="#cite_note-ResSoc-138"><span class="cite-bracket">&#91;</span>136<span class="cite-bracket">&#93;</span></a></sup> which are more thermostable than the originally used enzymes.<sup id="cite_ref-ResSoc_138-2" class="reference"><a href="#cite_note-ResSoc-138"><span class="cite-bracket">&#91;</span>136<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-Madsen_139-0" class="reference"><a href="#cite_note-Madsen-139"><span class="cite-bracket">&#91;</span>137<span class="cite-bracket">&#93;</span></a></sup> Starting in 1982, <a href="/wiki/Pullulanase" title="Pullulanase">pullulanases</a> from <i><a href="/wiki/Aspergillus_niger" title="Aspergillus niger">Aspergillus niger</a></i> were used in the production of glucose syrup to convert amylopectin to starch (amylose), thereby increasing the yield of glucose.<sup id="cite_ref-Norman_140-0" class="reference"><a href="#cite_note-Norman-140"><span class="cite-bracket">&#91;</span>138<span class="cite-bracket">&#93;</span></a></sup> The reaction is carried out at a pH = 4.6–5.2 and a temperature of 55–60&#160;°C.<sup id="cite_ref-Encyclopedia_of_Food_and_Health_11-1" class="reference"><a href="#cite_note-Encyclopedia_of_Food_and_Health-11"><span class="cite-bracket">&#91;</span>11<span class="cite-bracket">&#93;</span></a></sup> <a href="/wiki/Corn_syrup" title="Corn syrup">Corn syrup</a> has between 20% and 95% glucose in the dry matter.<sup id="cite_ref-141" class="reference"><a href="#cite_note-141"><span class="cite-bracket">&#91;</span>139<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-142" class="reference"><a href="#cite_note-142"><span class="cite-bracket">&#91;</span>140<span class="cite-bracket">&#93;</span></a></sup> The Japanese form of the glucose syrup, <a href="/wiki/Mizuame" title="Mizuame">Mizuame</a>, is made from <a href="/wiki/Sweet_potato" title="Sweet potato">sweet potato</a> or <a href="/wiki/Rice" title="Rice">rice</a> starch.<sup id="cite_ref-143" class="reference"><a href="#cite_note-143"><span class="cite-bracket">&#91;</span>141<span class="cite-bracket">&#93;</span></a></sup> <a href="/wiki/Maltodextrin" title="Maltodextrin">Maltodextrin</a> contains about 20% glucose. </p><p>Many crops can be used as the source of starch. <a href="/wiki/Maize" title="Maize">Maize</a>,<sup id="cite_ref-Fellows_136-2" class="reference"><a href="#cite_note-Fellows-136"><span class="cite-bracket">&#91;</span>134<span class="cite-bracket">&#93;</span></a></sup> rice,<sup id="cite_ref-Fellows_136-3" class="reference"><a href="#cite_note-Fellows-136"><span class="cite-bracket">&#91;</span>134<span class="cite-bracket">&#93;</span></a></sup> <a href="/wiki/Wheat" title="Wheat">wheat</a>,<sup id="cite_ref-Fellows_136-4" class="reference"><a href="#cite_note-Fellows-136"><span class="cite-bracket">&#91;</span>134<span class="cite-bracket">&#93;</span></a></sup> <a href="/wiki/Cassava" title="Cassava">cassava</a>,<sup id="cite_ref-Fellows_136-5" class="reference"><a href="#cite_note-Fellows-136"><span class="cite-bracket">&#91;</span>134<span class="cite-bracket">&#93;</span></a></sup> <a href="/wiki/Potato" title="Potato">potato</a>,<sup id="cite_ref-Fellows_136-6" class="reference"><a href="#cite_note-Fellows-136"><span class="cite-bracket">&#91;</span>134<span class="cite-bracket">&#93;</span></a></sup> <a href="/wiki/Barley" title="Barley">barley</a>,<sup id="cite_ref-Fellows_136-7" class="reference"><a href="#cite_note-Fellows-136"><span class="cite-bracket">&#91;</span>134<span class="cite-bracket">&#93;</span></a></sup> sweet potato,<sup id="cite_ref-Davidson_144-0" class="reference"><a href="#cite_note-Davidson-144"><span class="cite-bracket">&#91;</span>142<span class="cite-bracket">&#93;</span></a></sup> <a href="/wiki/Corn_husk" class="mw-redirect" title="Corn husk">corn husk</a> and <a href="/wiki/Sago" title="Sago">sago</a> are all used in various parts of the world. In the <a href="/wiki/United_States" title="United States">United States</a>, <a href="/wiki/Corn_starch" title="Corn starch">corn starch</a> (from maize) is used almost exclusively. Some commercial glucose occurs as a component of <a href="/wiki/Invert_sugar" class="mw-redirect" title="Invert sugar">invert sugar</a>, a roughly 1:1 mixture of glucose and fructose that is produced from sucrose. In principle, cellulose could be hydrolyzed to glucose, but this process is not yet commercially practical.<sup id="cite_ref-Ullmann_54-1" class="reference"><a href="#cite_note-Ullmann-54"><span class="cite-bracket">&#91;</span>54<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Conversion_to_fructose">Conversion to fructose</h3></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Isoglucose" class="mw-redirect" title="Isoglucose">isoglucose</a></div> <p>In the US, almost exclusively corn (more precisely, corn syrup) is used as glucose source for the production of <a href="/wiki/Isoglucose" class="mw-redirect" title="Isoglucose">isoglucose</a>, which is a mixture of glucose and fructose, since fructose has a higher sweetening power&#160;&#8211;&#32;with same physiological calorific value of 374 kilocalories per 100 g. The annual world production of isoglucose is 8 million tonnes (as of 2011).<sup id="cite_ref-Ullmann_48_137-1" class="reference"><a href="#cite_note-Ullmann_48-137"><span class="cite-bracket">&#91;</span>135<span class="cite-bracket">&#93;</span></a></sup> When made from corn syrup, the final product is <a href="/wiki/High-fructose_corn_syrup" title="High-fructose corn syrup">high-fructose corn syrup</a> (HFCS). </p> <div class="mw-heading mw-heading2"><h2 id="Commercial_usage">Commercial usage</h2></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Relativesweetness.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/bd/Relativesweetness.svg/220px-Relativesweetness.svg.png" decoding="async" width="220" height="142" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/bd/Relativesweetness.svg/330px-Relativesweetness.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/bd/Relativesweetness.svg/440px-Relativesweetness.svg.png 2x" data-file-width="512" data-file-height="330" /></a><figcaption>Relative sweetness of various sugars in comparison with sucrose<sup id="cite_ref-145" class="reference"><a href="#cite_note-145"><span class="cite-bracket">&#91;</span>143<span class="cite-bracket">&#93;</span></a></sup></figcaption></figure> <p>Glucose is mainly used for the production of fructose and of glucose-containing foods. In foods, it is used as a sweetener, <a href="/wiki/Humectant" title="Humectant">humectant</a>, to increase the <a href="/wiki/Volume" title="Volume">volume</a> and to create a softer <a href="/wiki/Mouthfeel" title="Mouthfeel">mouthfeel</a>.<sup id="cite_ref-Fellows_136-8" class="reference"><a href="#cite_note-Fellows-136"><span class="cite-bracket">&#91;</span>134<span class="cite-bracket">&#93;</span></a></sup> Various sources of glucose, such as grape juice (for wine) or malt (for beer), are used for fermentation to ethanol during the production of <a href="/wiki/Alcoholic_beverage" title="Alcoholic beverage">alcoholic beverages</a>. Most soft drinks in the US use HFCS-55 (with a fructose content of 55% in the dry mass), while most other HFCS-sweetened foods in the US use HFCS-42 (with a fructose content of 42% in the dry mass).<sup id="cite_ref-fda2014_146-0" class="reference"><a href="#cite_note-fda2014-146"><span class="cite-bracket">&#91;</span>144<span class="cite-bracket">&#93;</span></a></sup> In Mexico, on the other hand, soft drinks are sweetened by cane sugar, which has a higher sweetening power.<sup id="cite_ref-147" class="reference"><a href="#cite_note-147"><span class="cite-bracket">&#91;</span>145<span class="cite-bracket">&#93;</span></a></sup> In addition, glucose syrup is used, inter alia, in the production of <a href="/wiki/Confectionery" title="Confectionery">confectionery</a> such as <a href="/wiki/Candy" title="Candy">candies</a>, <a href="/wiki/Toffee" title="Toffee">toffee</a> and <a href="/wiki/Fondant_icing" title="Fondant icing">fondant</a>.<sup id="cite_ref-Beckett_148-0" class="reference"><a href="#cite_note-Beckett-148"><span class="cite-bracket">&#91;</span>146<span class="cite-bracket">&#93;</span></a></sup> Typical chemical reactions of glucose when heated under water-free conditions are <a href="/wiki/Caramelization" title="Caramelization">caramelization</a> and, in presence of amino acids, the <a href="/wiki/Maillard_reaction" title="Maillard reaction">Maillard reaction</a>. </p><p>In addition, various organic acids can be biotechnologically produced from glucose, for example by fermentation with <i><a href="/wiki/Clostridium_thermoaceticum" class="mw-redirect" title="Clostridium thermoaceticum">Clostridium thermoaceticum</a></i> to produce <a href="/wiki/Acetic_acid" title="Acetic acid">acetic acid</a>, with <i><a href="/wiki/Penicillium_notatum" class="mw-redirect" title="Penicillium notatum">Penicillium notatum</a></i> for the production of <a href="/w/index.php?title=Araboascorbic_acid&amp;action=edit&amp;redlink=1" class="new" title="Araboascorbic acid (page does not exist)">araboascorbic acid</a>, with <i><a href="/w/index.php?title=Rhizopus_delemar&amp;action=edit&amp;redlink=1" class="new" title="Rhizopus delemar (page does not exist)">Rhizopus delemar</a></i> for the production of <a href="/wiki/Fumaric_acid" title="Fumaric acid">fumaric acid</a>, with <i><a href="/wiki/Aspergillus_niger" title="Aspergillus niger">Aspergillus niger</a></i> for the production of <a href="/wiki/Gluconic_acid" title="Gluconic acid">gluconic acid</a>, with <i><a href="/w/index.php?title=Candida_brumptii&amp;action=edit&amp;redlink=1" class="new" title="Candida brumptii (page does not exist)">Candida brumptii</a></i> to produce <a href="/wiki/Isocitric_acid" title="Isocitric acid">isocitric acid</a>, with <i><a href="/wiki/Aspergillus_terreus" title="Aspergillus terreus">Aspergillus terreus</a></i> for the production of <a href="/wiki/Itaconic_acid" title="Itaconic acid">itaconic acid</a>, with <i><a href="/wiki/Pseudomonas_fluorescens" title="Pseudomonas fluorescens">Pseudomonas fluorescens</a></i> for the production of <a href="/w/index.php?title=2-ketogluconic_acid&amp;action=edit&amp;redlink=1" class="new" title="2-ketogluconic acid (page does not exist)">2-ketogluconic acid</a>, with <i><a href="/w/index.php?title=Gluconobacter_suboxydans&amp;action=edit&amp;redlink=1" class="new" title="Gluconobacter suboxydans (page does not exist)">Gluconobacter suboxydans</a></i> for the production of <a href="/w/index.php?title=5-ketogluconic_acid&amp;action=edit&amp;redlink=1" class="new" title="5-ketogluconic acid (page does not exist)">5-ketogluconic acid</a>, with <i><a href="/wiki/Aspergillus_oryzae" title="Aspergillus oryzae">Aspergillus oryzae</a></i> for the production of <a href="/wiki/Kojic_acid" title="Kojic acid">kojic acid</a>, with <i><a href="/wiki/Lactobacillus_delbrueckii" title="Lactobacillus delbrueckii">Lactobacillus delbrueckii</a></i> for the production of <a href="/wiki/Lactic_acid" title="Lactic acid">lactic acid</a>, with <i><a href="/wiki/Lactobacillus_brevis" class="mw-redirect" title="Lactobacillus brevis">Lactobacillus brevis</a></i> for the production of <a href="/wiki/Malic_acid" title="Malic acid">malic acid</a>, with <i><a href="/wiki/Propionibacter_shermanii" class="mw-redirect" title="Propionibacter shermanii">Propionibacter shermanii</a></i> for the production of <a href="/wiki/Propionic_acid" title="Propionic acid">propionic acid</a>, with <i><a href="/wiki/Pseudomonas_aeruginosa" title="Pseudomonas aeruginosa">Pseudomonas aeruginosa</a></i> for the production of <a href="/wiki/Pyruvic_acid" title="Pyruvic acid">pyruvic acid</a> and with <i><a href="/w/index.php?title=Gluconobacter_suboxydans&amp;action=edit&amp;redlink=1" class="new" title="Gluconobacter suboxydans (page does not exist)">Gluconobacter suboxydans</a></i> for the production of <a href="/wiki/Tartaric_acid" title="Tartaric acid">tartaric acid</a>.<sup id="cite_ref-Kent_149-0" class="reference"><a href="#cite_note-Kent-149"><span class="cite-bracket">&#91;</span>147<span class="cite-bracket">&#93;</span></a></sup><sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">&#91;<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs additional references to reliable sources. (April 2022)">additional citation(s) needed</span></a></i>&#93;</sup> Potent, bioactive natural products like triptolide that inhibit mammalian transcription via inhibition of the XPB subunit of the general transcription factor TFIIH has been recently reported as a glucose conjugate for targeting hypoxic cancer cells with increased glucose transporter expression.<sup id="cite_ref-150" class="reference"><a href="#cite_note-150"><span class="cite-bracket">&#91;</span>148<span class="cite-bracket">&#93;</span></a></sup> Recently, glucose has been gaining commercial use as a key component of "kits" containing lactic acid and insulin intended to induce hypoglycemia and hyperlactatemia to combat different cancers and infections.<sup id="cite_ref-151" class="reference"><a href="#cite_note-151"><span class="cite-bracket">&#91;</span>149<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Analysis">Analysis</h2></div> <p>When a glucose molecule is to be detected at a certain position in a larger molecule, <a href="/wiki/Nuclear_magnetic_resonance_spectroscopy" title="Nuclear magnetic resonance spectroscopy">nuclear magnetic resonance spectroscopy</a>, <a href="/wiki/X-ray_crystallography" title="X-ray crystallography">X-ray crystallography</a> analysis or <a href="/wiki/Lectin" title="Lectin">lectin</a> <a href="/wiki/Immunostaining" title="Immunostaining">immunostaining</a> is performed with <a href="/wiki/Concanavalin_A" title="Concanavalin A">concanavalin A</a> reporter enzyme conjugate, which binds only glucose or mannose. </p> <div class="mw-heading mw-heading3"><h3 id="Classical_qualitative_detection_reactions">Classical qualitative detection reactions</h3></div> <p>These reactions have only historical significance: </p> <div class="mw-heading mw-heading4"><h4 id="Fehling_test">Fehling test</h4></div> <p>The <a href="/wiki/Fehling_test" class="mw-redirect" title="Fehling test">Fehling test</a> is a classic method for the detection of aldoses.<sup id="cite_ref-Fehling-Harn_152-0" class="reference"><a href="#cite_note-Fehling-Harn-152"><span class="cite-bracket">&#91;</span>150<span class="cite-bracket">&#93;</span></a></sup> Due to mutarotation, glucose is always present to a small extent as an open-chain aldehyde. By adding the Fehling reagents (Fehling (I) solution and Fehling (II) solution), the aldehyde group is oxidized to a <a href="/wiki/Carboxylic_acid" title="Carboxylic acid">carboxylic acid</a>, while the Cu<sup>2+</sup> tartrate complex is reduced to Cu<sup>+</sup> and forms a brick red precipitate (Cu<sub>2</sub>O). </p> <div class="mw-heading mw-heading4"><h4 id="Tollens_test">Tollens test</h4></div> <p>In the <a href="/wiki/Tollens_test" class="mw-redirect" title="Tollens test">Tollens test</a>, after addition of ammoniacal <a href="/wiki/Silver_nitrate" title="Silver nitrate">AgNO<sub>3</sub></a> to the sample solution, glucose reduces Ag<sup>+</sup> to elemental <a href="/wiki/Silver" title="Silver">silver</a>.<sup id="cite_ref-153" class="reference"><a href="#cite_note-153"><span class="cite-bracket">&#91;</span>151<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Barfoed_test">Barfoed test</h4></div> <p>In <a href="/wiki/Barfoed%27s_test" title="Barfoed&#39;s test">Barfoed's test</a>,<sup id="cite_ref-barfoed_154-0" class="reference"><a href="#cite_note-barfoed-154"><span class="cite-bracket">&#91;</span>152<span class="cite-bracket">&#93;</span></a></sup> a solution of dissolved <a href="/wiki/Copper_acetate" class="mw-redirect" title="Copper acetate">copper acetate</a>, <a href="/wiki/Sodium_acetate" title="Sodium acetate">sodium acetate</a> and acetic acid is added to the solution of the sugar to be tested and subsequently heated in a water bath for a few minutes. Glucose and other monosaccharides rapidly produce a reddish color and reddish brown <a href="/wiki/Copper(I)_oxide" title="Copper(I) oxide">copper(I) oxide</a> (Cu<sub>2</sub>O). </p> <div class="mw-heading mw-heading4"><h4 id="Nylander's_test"><span id="Nylander.27s_test"></span>Nylander's test</h4></div> <p>As a reducing sugar, glucose reacts in the <a href="/wiki/Nylander%27s_test" title="Nylander&#39;s test">Nylander's test</a>.<sup id="cite_ref-155" class="reference"><a href="#cite_note-155"><span class="cite-bracket">&#91;</span>153<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Other_tests">Other tests</h4></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/Maillard_reaction" title="Maillard reaction">Maillard reaction</a> and <a href="/wiki/Lye_roll" title="Lye roll">Lye roll</a></div> <p>Upon heating a dilute <a href="/wiki/Potassium_hydroxide" title="Potassium hydroxide">potassium hydroxide</a> solution with glucose to 100&#160;°C, a strong reddish browning and a caramel-like odor develops.<sup id="cite_ref-Schwedt_102_156-0" class="reference"><a href="#cite_note-Schwedt_102-156"><span class="cite-bracket">&#91;</span>154<span class="cite-bracket">&#93;</span></a></sup> Concentrated <a href="/wiki/Sulfuric_acid" title="Sulfuric acid">sulfuric acid</a> dissolves dry glucose without blackening at room temperature forming sugar sulfuric acid.<sup id="cite_ref-Schwedt_102_156-1" class="reference"><a href="#cite_note-Schwedt_102-156"><span class="cite-bracket">&#91;</span>154<span class="cite-bracket">&#93;</span></a></sup><sup class="noprint Inline-Template" style="white-space:nowrap;">&#91;<i><a href="/wiki/Wikipedia:Verifiability" title="Wikipedia:Verifiability"><span title="The material near this tag needs to be fact-checked with the cited source(s). (April 2022)">verification needed</span></a></i>&#93;</sup> In a yeast solution, alcoholic fermentation produces carbon dioxide in the ratio of 2.0454 molecules of glucose to one molecule of <a href="/wiki/Carbon_dioxide" title="Carbon dioxide">CO<sub>2</sub></a>.<sup id="cite_ref-Schwedt_102_156-2" class="reference"><a href="#cite_note-Schwedt_102-156"><span class="cite-bracket">&#91;</span>154<span class="cite-bracket">&#93;</span></a></sup> Glucose forms a black mass with <a href="/wiki/Stannous_chloride" class="mw-redirect" title="Stannous chloride">stannous chloride</a>.<sup id="cite_ref-Schwedt_102_156-3" class="reference"><a href="#cite_note-Schwedt_102-156"><span class="cite-bracket">&#91;</span>154<span class="cite-bracket">&#93;</span></a></sup> In an ammoniacal silver solution, glucose (as well as lactose and dextrin) leads to the deposition of silver. In an ammoniacal <a href="/wiki/Lead_acetate" title="Lead acetate">lead acetate</a> solution, white <a href="/w/index.php?title=Lead_glycoside&amp;action=edit&amp;redlink=1" class="new" title="Lead glycoside (page does not exist)">lead glycoside</a> is formed in the presence of glucose, which becomes less soluble on cooking and turns brown.<sup id="cite_ref-Schwedt_102_156-4" class="reference"><a href="#cite_note-Schwedt_102-156"><span class="cite-bracket">&#91;</span>154<span class="cite-bracket">&#93;</span></a></sup> In an ammoniacal copper solution, yellow <a href="/wiki/Copper_oxide" title="Copper oxide">copper oxide</a> hydrate is formed with glucose at room temperature, while red copper oxide is formed during boiling (same with dextrin, except for with an ammoniacal copper acetate solution).<sup id="cite_ref-Schwedt_102_156-5" class="reference"><a href="#cite_note-Schwedt_102-156"><span class="cite-bracket">&#91;</span>154<span class="cite-bracket">&#93;</span></a></sup> With <a href="/wiki/Picric_acid" title="Picric acid">Hager's reagent</a>, glucose forms <a href="/wiki/Mercury_oxide" title="Mercury oxide">mercury oxide</a> during boiling.<sup id="cite_ref-Schwedt_102_156-6" class="reference"><a href="#cite_note-Schwedt_102-156"><span class="cite-bracket">&#91;</span>154<span class="cite-bracket">&#93;</span></a></sup> An alkaline <a href="/wiki/Bismuth" title="Bismuth">bismuth</a> solution is used to precipitate elemental, black-brown bismuth with glucose.<sup id="cite_ref-Schwedt_102_156-7" class="reference"><a href="#cite_note-Schwedt_102-156"><span class="cite-bracket">&#91;</span>154<span class="cite-bracket">&#93;</span></a></sup> Glucose boiled in an <a href="/wiki/Ammonium_molybdate" title="Ammonium molybdate">ammonium molybdate</a> solution turns the solution blue. A solution with <a href="/wiki/Indigo_carmine" title="Indigo carmine">indigo carmine</a> and <a href="/wiki/Sodium_carbonate" title="Sodium carbonate">sodium carbonate</a> destains when boiled with glucose.<sup id="cite_ref-Schwedt_102_156-8" class="reference"><a href="#cite_note-Schwedt_102-156"><span class="cite-bracket">&#91;</span>154<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Instrumental_quantification">Instrumental quantification</h3></div> <div class="mw-heading mw-heading4"><h4 id="Refractometry_and_polarimetry">Refractometry and polarimetry</h4></div> <p>In concentrated solutions of glucose with a low proportion of other carbohydrates, its concentration can be determined with a polarimeter. For sugar mixtures, the concentration can be determined with a <a href="/wiki/Refractometer" title="Refractometer">refractometer</a>, for example in the <a href="/wiki/Oechsle_scale" title="Oechsle scale">Oechsle</a> determination in the course of the production of wine. </p> <div class="mw-heading mw-heading4"><h4 id="Photometric_enzymatic_methods_in_solution">Photometric enzymatic methods in solution</h4></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Glucose_oxidation_reaction" class="mw-redirect" title="Glucose oxidation reaction">Glucose oxidation reaction</a></div> <p>The enzyme glucose oxidase (GOx) converts glucose into gluconic acid and hydrogen peroxide while consuming oxygen. Another enzyme, peroxidase, catalyzes a chromogenic reaction (Trinder reaction)<sup id="cite_ref-157" class="reference"><a href="#cite_note-157"><span class="cite-bracket">&#91;</span>155<span class="cite-bracket">&#93;</span></a></sup> of <a href="/wiki/Phenol" title="Phenol">phenol</a> with <a href="/wiki/4-Aminoantipyrine" class="mw-redirect" title="4-Aminoantipyrine">4-aminoantipyrine</a> to a purple dye.<sup id="cite_ref-purpuled_158-0" class="reference"><a href="#cite_note-purpuled-158"><span class="cite-bracket">&#91;</span>156<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Photometric_test-strip_method">Photometric test-strip method</h4></div> <p>The test-strip method employs the above-mentioned enzymatic conversion of glucose to gluconic acid to form hydrogen peroxide. The reagents are immobilised on a polymer matrix, the so-called test strip, which assumes a more or less intense color. This can be measured reflectometrically at 510&#160;nm with the aid of an LED-based handheld photometer. This allows routine blood sugar determination by nonscientists. In addition to the reaction of phenol with 4-aminoantipyrine, new chromogenic reactions have been developed that allow photometry at higher wavelengths (550&#160;nm, 750&#160;nm).<sup id="cite_ref-purpuled_158-1" class="reference"><a href="#cite_note-purpuled-158"><span class="cite-bracket">&#91;</span>156<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-159" class="reference"><a href="#cite_note-159"><span class="cite-bracket">&#91;</span>157<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Amperometric_glucose_sensor">Amperometric glucose sensor</h4></div> <p>The electroanalysis of glucose is also based on the enzymatic reaction mentioned above. The produced hydrogen peroxide can be amperometrically quantified by anodic oxidation at a potential of 600 mV.<sup id="cite_ref-160" class="reference"><a href="#cite_note-160"><span class="cite-bracket">&#91;</span>158<span class="cite-bracket">&#93;</span></a></sup> The GOx is immobilized on the electrode surface or in a membrane placed close to the electrode. Precious metals such as platinum or gold are used in electrodes, as well as carbon nanotube electrodes, which e.g. are doped with boron.<sup id="cite_ref-161" class="reference"><a href="#cite_note-161"><span class="cite-bracket">&#91;</span>159<span class="cite-bracket">&#93;</span></a></sup> Cu–CuO nanowires are also used as enzyme-free amperometric electrodes, reaching a detection limit of 50&#160;μmol/L.<sup id="cite_ref-162" class="reference"><a href="#cite_note-162"><span class="cite-bracket">&#91;</span>160<span class="cite-bracket">&#93;</span></a></sup> A particularly promising method is the so-called "enzyme wiring", where the electron flowing during the oxidation is transferred via a molecular wire directly from the enzyme to the electrode.<sup id="cite_ref-163" class="reference"><a href="#cite_note-163"><span class="cite-bracket">&#91;</span>161<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Other_sensory_methods">Other sensory methods</h4></div> <p>There are a variety of other chemical sensors for measuring glucose.<sup id="cite_ref-Borisov_164-0" class="reference"><a href="#cite_note-Borisov-164"><span class="cite-bracket">&#91;</span>162<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-165" class="reference"><a href="#cite_note-165"><span class="cite-bracket">&#91;</span>163<span class="cite-bracket">&#93;</span></a></sup> Given the importance of glucose analysis in the life sciences, numerous optical probes have also been developed for saccharides based on the use of boronic acids,<sup id="cite_ref-166" class="reference"><a href="#cite_note-166"><span class="cite-bracket">&#91;</span>164<span class="cite-bracket">&#93;</span></a></sup> which are particularly useful for intracellular sensory applications where other (optical) methods are not or only conditionally usable. In addition to the organic boronic acid derivatives, which often bind highly specifically to the 1,2-diol groups of sugars, there are also other probe concepts classified by functional mechanisms which use selective glucose-binding proteins (e.g. concanavalin A) as a receptor. Furthermore, methods were developed which indirectly detect the glucose concentration via the concentration of metabolized products, e.g. by the consumption of oxygen using fluorescence-optical sensors.<sup id="cite_ref-167" class="reference"><a href="#cite_note-167"><span class="cite-bracket">&#91;</span>165<span class="cite-bracket">&#93;</span></a></sup> Finally, there are enzyme-based concepts that use the intrinsic absorbance or fluorescence of (fluorescence-labeled) enzymes as reporters.<sup id="cite_ref-Borisov_164-1" class="reference"><a href="#cite_note-Borisov-164"><span class="cite-bracket">&#91;</span>162<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Copper_iodometry">Copper iodometry</h4></div> <p>Glucose can be quantified by copper iodometry.<sup id="cite_ref-Galant_168-0" class="reference"><a href="#cite_note-Galant-168"><span class="cite-bracket">&#91;</span>166<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Chromatographic_methods">Chromatographic methods</h3></div> <p>In particular, for the analysis of complex mixtures containing glucose, e.g. in honey, chromatographic methods such as <a href="/wiki/High_performance_liquid_chromatography" class="mw-redirect" title="High performance liquid chromatography">high performance liquid chromatography</a> and <a href="/wiki/Gas_chromatography" title="Gas chromatography">gas chromatography</a><sup id="cite_ref-Galant_168-1" class="reference"><a href="#cite_note-Galant-168"><span class="cite-bracket">&#91;</span>166<span class="cite-bracket">&#93;</span></a></sup> are often used in combination with <a href="/wiki/Mass_spectrometry" title="Mass spectrometry">mass spectrometry</a>.<sup id="cite_ref-169" class="reference"><a href="#cite_note-169"><span class="cite-bracket">&#91;</span>167<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-mpg-210190_170-0" class="reference"><a href="#cite_note-mpg-210190-170"><span class="cite-bracket">&#91;</span>168<span class="cite-bracket">&#93;</span></a></sup> Taking into account the isotope ratios, it is also possible to reliably detect honey adulteration by added sugars with these methods.<sup id="cite_ref-171" class="reference"><a href="#cite_note-171"><span class="cite-bracket">&#91;</span>169<span class="cite-bracket">&#93;</span></a></sup> Derivatization using silylation reagents is commonly used.<sup id="cite_ref-172" class="reference"><a href="#cite_note-172"><span class="cite-bracket">&#91;</span>170<span class="cite-bracket">&#93;</span></a></sup> Also, the proportions of di- and trisaccharides can be quantified. </p> <div class="mw-heading mw-heading4"><h4 id="In_vivo_analysis">In vivo analysis</h4></div> <p>Glucose uptake in cells of organisms is measured with <a href="/wiki/2-deoxy-D-glucose" class="mw-redirect" title="2-deoxy-D-glucose">2-deoxy-D-glucose</a> or <a href="/wiki/Fluorodeoxyglucose" class="mw-redirect" title="Fluorodeoxyglucose">fluorodeoxyglucose</a>.<sup id="cite_ref-Dwyer_115-2" class="reference"><a href="#cite_note-Dwyer-115"><span class="cite-bracket">&#91;</span>114<span class="cite-bracket">&#93;</span></a></sup> (<sup>18</sup>F)fluorodeoxyglucose is used as a tracer in <a href="/wiki/Positron_emission_tomography" title="Positron emission tomography">positron emission tomography</a> in oncology and neurology,<sup id="cite_ref-gdch_173-0" class="reference"><a href="#cite_note-gdch-173"><span class="cite-bracket">&#91;</span>171<span class="cite-bracket">&#93;</span></a></sup> where it is by far the most commonly used diagnostic agent.<sup id="cite_ref-174" class="reference"><a href="#cite_note-174"><span class="cite-bracket">&#91;</span>172<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="References">References</h2></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239543626"><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text"><a rel="nofollow" class="external text" href="https://iupac.qmul.ac.uk/2carb/02.html">Nomenclature of Carbohydrates (Recommendations 1996) | 2-Carb-2</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20230827082825/https://iupac.qmul.ac.uk/2carb/02.html">Archived</a> 27 August 2023 at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a>. <i>iupac.qmul.ac.uk</i>.</span> </li> <li id="cite_note-Boerio-Goates_1991_403–9-2"><span class="mw-cite-backlink">^ <a href="#cite_ref-Boerio-Goates_1991_403–9_2-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Boerio-Goates_1991_403–9_2-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBoerio-Goates1991" class="citation cs2">Boerio-Goates J (1991), "Heat-capacity measurements and thermodynamic functions of crystalline α-D-glucose at temperatures from 10K to 340K", <i>J. Chem. Thermodyn.</i>, <b>23</b> (5): 403–09, <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/1991JChTh..23..403B">1991JChTh..23..403B</a>, <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FS0021-9614%2805%2980128-4">10.1016/S0021-9614(05)80128-4</a></cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=J.+Chem.+Thermodyn.&amp;rft.atitle=Heat-capacity+measurements+and+thermodynamic+functions+of+crystalline+%CE%B1-D-glucose+at+temperatures+from+10K+to+340K&amp;rft.volume=23&amp;rft.issue=5&amp;rft.pages=403-09&amp;rft.date=1991&amp;rft_id=info%3Adoi%2F10.1016%2FS0021-9614%2805%2980128-4&amp;rft_id=info%3Abibcode%2F1991JChTh..23..403B&amp;rft.aulast=Boerio-Goates&amp;rft.aufirst=Juliana&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AGlucose" class="Z3988"></span></span> </li> <li id="cite_note-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-3">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPonomarevMigarskaya1960" class="citation cs2">Ponomarev VV, Migarskaya LB (1960), "Heats of combustion of some amino-acids", <i>Russ. J. Phys. Chem. (Engl. Transl.)</i>, <b>34</b>: 1182–83</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=Russ.+J.+Phys.+Chem.+%28Engl.+Transl.%29&amp;rft.atitle=Heats+of+combustion+of+some+amino-acids&amp;rft.volume=34&amp;rft.pages=1182-83&amp;rft.date=1960&amp;rft.aulast=Ponomarev&amp;rft.aufirst=V.+V.&amp;rft.au=Migarskaya%2C+L.+B.&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AGlucose" class="Z3988"></span></span> </li> <li id="cite_note-DombKost1998-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-DombKost1998_4-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFDombKostWiseman1998" class="citation book cs1">Domb AJ, Kost J, Wiseman D (4 February 1998). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=iLjhl6AvfIsC&amp;pg=PA275"><i>Handbook of Biodegradable Polymers</i></a>. CRC Press. p.&#160;275. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a>&#160;<a href="/wiki/Special:BookSources/978-1-4200-4936-7" title="Special:BookSources/978-1-4200-4936-7"><bdi>978-1-4200-4936-7</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=book&amp;rft.btitle=Handbook+of+Biodegradable+Polymers&amp;rft.pages=275&amp;rft.pub=CRC+Press&amp;rft.date=1998-02-04&amp;rft.isbn=978-1-4200-4936-7&amp;rft.aulast=Domb&amp;rft.aufirst=Abraham+J.&amp;rft.au=Kost%2C+Joseph&amp;rft.au=Wiseman%2C+David&amp;rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DiLjhl6AvfIsC%26pg%3DPA275&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AGlucose" class="Z3988"></span></span> </li> <li id="cite_note-froms-5"><span class="mw-cite-backlink">^ <a href="#cite_ref-froms_5-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-froms_5-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://drugs.ncats.io/drug/IY9XDZ35W2">"NCATS Inxight Drugs — DEXTROSE, UNSPECIFIED FORM"</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20231211224631/https://drugs.ncats.io/drug/IY9XDZ35W2">Archived</a> from the original on 11 December 2023<span class="reference-accessdate">. Retrieved <span class="nowrap">18 March</span> 2024</span>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=unknown&amp;rft.btitle=NCATS+Inxight+Drugs+%E2%80%94+DEXTROSE%2C+UNSPECIFIED+FORM&amp;rft_id=https%3A%2F%2Fdrugs.ncats.io%2Fdrug%2FIY9XDZ35W2&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AGlucose" class="Z3988"></span></span> </li> <li id="cite_note-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-6">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKamide2005" class="citation book cs1">Kamide K (2005). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=28Vx9OkEtQcC&amp;pg=PA1"><i>Cellulose products and Cellulose Derivatives: Molecular Characterization and its Applications</i></a> (1st&#160;ed.). Amsterdam: Elsevier. p.&#160;1. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a>&#160;<a href="/wiki/Special:BookSources/978-0-08-045444-3" title="Special:BookSources/978-0-08-045444-3"><bdi>978-0-08-045444-3</bdi></a><span class="reference-accessdate">. Retrieved <span class="nowrap">13 May</span> 2021</span>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=book&amp;rft.btitle=Cellulose+products+and+Cellulose+Derivatives%3A+Molecular+Characterization+and+its+Applications&amp;rft.place=Amsterdam&amp;rft.pages=1&amp;rft.edition=1st&amp;rft.pub=Elsevier&amp;rft.date=2005&amp;rft.isbn=978-0-08-045444-3&amp;rft.aulast=Kamide&amp;rft.aufirst=Kenji&amp;rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D28Vx9OkEtQcC%26pg%3DPA1&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AGlucose" class="Z3988"></span></span> </li> <li id="cite_note-r2-7"><span class="mw-cite-backlink">^ <a href="#cite_ref-r2_7-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-r2_7-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-r2_7-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-r2_7-3"><sup><i><b>d</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.biologyonline.com/dictionary/l-glucose">"L-glucose"</a>. <i>Biology Articles, Tutorials &amp; Dictionary Online</i>. 7 October 2019. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20220525135220/https://www.biologyonline.com/dictionary/l-glucose">Archived</a> from the original on 25 May 2022<span class="reference-accessdate">. Retrieved <span class="nowrap">6 May</span> 2022</span>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=unknown&amp;rft.jtitle=Biology+Articles%2C+Tutorials+%26+Dictionary+Online&amp;rft.atitle=L-glucose&amp;rft.date=2019-10-07&amp;rft_id=https%3A%2F%2Fwww.biologyonline.com%2Fdictionary%2Fl-glucose&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AGlucose" class="Z3988"></span></span> </li> <li id="cite_note-WHO21st-8"><span class="mw-cite-backlink">^ <a href="#cite_ref-WHO21st_8-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-WHO21st_8-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWorld_Health_Organization2019" class="citation book cs1"><a href="/wiki/World_Health_Organization" title="World Health Organization">World Health Organization</a> (2019). <i>World Health Organization model list of essential medicines: 21st list 2019</i>. Geneva: World Health Organization. <a href="/wiki/Hdl_(identifier)" class="mw-redirect" title="Hdl (identifier)">hdl</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://hdl.handle.net/10665%2F325771">10665/325771</a></span>. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=book&amp;rft.btitle=World+Health+Organization+model+list+of+essential+medicines%3A+21st+list+2019&amp;rft.place=Geneva&amp;rft.pub=World+Health+Organization&amp;rft.date=2019&amp;rft_id=info%3Ahdl%2F10665%2F325771&amp;rft.au=World+Health+Organization&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AGlucose" class="Z3988"></span></span> </li> <li id="cite_note-9"><span class="mw-cite-backlink"><b><a href="#cite_ref-9">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://www.etymonline.com/index.php?term=glucose">"Online Etymology Dictionary"</a>. <i>Etymonline.com</i>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20161126065057/http://www.etymonline.com/index.php?term=glucose">Archived</a> from the original on 26 November 2016<span class="reference-accessdate">. Retrieved <span class="nowrap">25 November</span> 2016</span>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=unknown&amp;rft.jtitle=Etymonline.com&amp;rft.atitle=Online+Etymology+Dictionary&amp;rft_id=http%3A%2F%2Fwww.etymonline.com%2Findex.php%3Fterm%3Dglucose&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AGlucose" class="Z3988"></span></span> </li> <li id="cite_note-10"><span class="mw-cite-backlink"><b><a href="#cite_ref-10">^</a></b></span> <span class="reference-text">Thénard, Gay-Lussac, Biot, and Dumas (1838) <a rel="nofollow" class="external text" href="http://gallica.bnf.fr/ark:/12148/bpt6k29662/f106.langEN">"Rapport sur un mémoire de M. Péligiot, intitulé: Recherches sur la nature et les propriétés chimiques des sucres"</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20151206043449/http://gallica.bnf.fr/ark:/12148/bpt6k29662/f106.langEN">Archived</a> 6 December 2015 at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a> (Report on a memoir of Mr. Péligiot, titled: Investigations on the nature and chemical properties of sugars), <i>Comptes rendus</i>, <b>7</b>&#160;: 106–113. <a rel="nofollow" class="external text" href="http://gallica.bnf.fr/ark:/12148/bpt6k29662/f109.langEN">From page 109</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20151206050123/http://gallica.bnf.fr/ark:/12148/bpt6k29662/f109.langEN">Archived</a> 6 December 2015 at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a>: "Il résulte des comparaisons faites par M. Péligot, que le sucre de raisin, celui d'amidon, celui de diabètes et celui de miel ont parfaitement la même composition et les mêmes propriétés, et constituent un seul corps que nous proposons d'appeler <em>Glucose</em> (1). ... (1) γλευχος, moût, vin doux." It follows from the comparisons made by Mr. Péligot, that the sugar from grapes, that from starch, that from diabetes and that from honey have exactly the same composition and the same properties, and constitute a single substance that we propose to call <i>glucose</i> (1) ... (1) γλευχος, must, sweet wine.</span> </li> <li id="cite_note-Encyclopedia_of_Food_and_Health-11"><span class="mw-cite-backlink">^ <a href="#cite_ref-Encyclopedia_of_Food_and_Health_11-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Encyclopedia_of_Food_and_Health_11-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation book cs1"><a rel="nofollow" class="external text" href="https://books.google.com/books?id=O-t9BAAAQBAJ&amp;pg=RA2-PA239"><i>Encyclopedia of Food and Health</i></a>. Academic Press. 2015. p.&#160;239. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a>&#160;<a href="/wiki/Special:BookSources/978-0-12-384953-3" title="Special:BookSources/978-0-12-384953-3"><bdi>978-0-12-384953-3</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20180223145046/https://books.google.com/books?id=O-t9BAAAQBAJ&amp;pg=RA2-PA239">Archived</a> from the original on 23 February 2018.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=book&amp;rft.btitle=Encyclopedia+of+Food+and+Health&amp;rft.pages=239&amp;rft.pub=Academic+Press&amp;rft.date=2015&amp;rft.isbn=978-0-12-384953-3&amp;rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DO-t9BAAAQBAJ%26pg%3DRA2-PA239&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AGlucose" class="Z3988"></span></span> </li> <li id="cite_note-12"><span class="mw-cite-backlink"><b><a href="#cite_ref-12">^</a></b></span> <span class="reference-text">Marggraf (1747) <a rel="nofollow" class="external text" href="https://books.google.com/books?id=lJQDAAAAMAAJ&amp;pg=PA79">"Experiences chimiques faites dans le dessein de tirer un veritable sucre de diverses plantes, qui croissent dans nos contrées"</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20160624083152/https://books.google.com/books?id=lJQDAAAAMAAJ&amp;pg=PA79">Archived</a> 24 June 2016 at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a> [Chemical experiments made with the intention of extracting real sugar from diverse plants that grow in our lands], <i>Histoire de l'académie royale des sciences et belles-lettres de Berlin</i>, pp. 79–90. <a rel="nofollow" class="external text" href="https://archive.org/details/bub_gb_lJQDAAAAMAAJ/page/n114">From page 90:</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20141027011957/http://books.google.com/books?id=lJQDAAAAMAAJ&amp;pg=PA90">Archived</a> 27 October 2014 at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a> <i>"Les raisins secs, etant humectés d'une petite quantité d'eau, de maniere qu'ils mollissent, peuvent alors etre pilés, &amp; le suc qu'on en exprime, etant depuré &amp; épaissi, fournira une espece de Sucre."</i> (Raisins, being moistened with a small quantity of water, in a way that they soften, can be then pressed, and the juice that is squeezed out, [after] being purified and thickened, will provide a sort of sugar.)</span> </li> <li id="cite_note-Robyt_7-13"><span class="mw-cite-backlink"><b><a href="#cite_ref-Robyt_7_13-0">^</a></b></span> <span class="reference-text">John F. Robyt: <i>Essentials of Carbohydrate Chemistry.</i> Springer Science &amp; Business Media, 2012, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a>&#160;<a href="/wiki/Special:BookSources/978-1-461-21622-3" title="Special:BookSources/978-1-461-21622-3">978-1-461-21622-3</a>. p. 7.</span> </li> <li id="cite_note-Rosanoff-14"><span class="mw-cite-backlink"><b><a href="#cite_ref-Rosanoff_14-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRosanoff1906" class="citation journal cs1">Rosanoff MA (1906). <a rel="nofollow" class="external text" href="https://zenodo.org/record/1428874">"On Fischer's Classification of Stereo-Isomers.1"</a>. <i>Journal of the American Chemical Society</i>. <b>28</b>: 114–121. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fja01967a014">10.1021/ja01967a014</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20191217170142/https://zenodo.org/record/1428874">Archived</a> from the original on 17 December 2019<span class="reference-accessdate">. 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Retrieved <span class="nowrap">18 March</span> 2024</span>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=unknown&amp;rft.btitle=API+%26%23124%3B+glucose+monohydrate&amp;rft_id=https%3A%2F%2Fwww.cdek.liu.edu%2Fapi%2F110617%2F&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AGlucose" class="Z3988"></span></span> </li> <li id="cite_note-diff-40"><span class="mw-cite-backlink">^ <a href="#cite_ref-diff_40-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-diff_40-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-diff_40-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-diff_40-3"><sup><i><b>d</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://gtspfood.com/en/the-difference-between-dextrose-anhydrous-and-dextrose-monohydrate/">"The difference between dextrose anhydrous and dextrose monohydrate"</a>. 28 December 2022. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20240318213001/https://gtspfood.com/en/the-difference-between-dextrose-anhydrous-and-dextrose-monohydrate/">Archived</a> from the original on 18 March 2024<span class="reference-accessdate">. Retrieved <span class="nowrap">18 March</span> 2024</span>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=unknown&amp;rft.btitle=The+difference+between+dextrose+anhydrous+and+dextrose+monohydrate&amp;rft.date=2022-12-28&amp;rft_id=https%3A%2F%2Fgtspfood.com%2Fen%2Fthe-difference-between-dextrose-anhydrous-and-dextrose-monohydrate%2F&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AGlucose" class="Z3988"></span></span> </li> <li id="cite_note-ahn1-41"><span class="mw-cite-backlink"><b><a href="#cite_ref-ahn1_41-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.chembk.com/en/chem/Dextrose%20anhydrous">"Dextrose anhydrous"</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20240318212942/https://www.chembk.com/en/chem/Dextrose%20anhydrous">Archived</a> from the original on 18 March 2024<span class="reference-accessdate">. Retrieved <span class="nowrap">18 March</span> 2024</span>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=unknown&amp;rft.btitle=Dextrose+anhydrous&amp;rft_id=https%3A%2F%2Fwww.chembk.com%2Fen%2Fchem%2FDextrose%2520anhydrous&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AGlucose" class="Z3988"></span></span> </li> <li id="cite_note-42"><span class="mw-cite-backlink"><b><a href="#cite_ref-42">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKhvorovaAndreevLukin2020" class="citation journal cs1">Khvorova LS, Andreev NR, Lukin ND (January 2020). 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Retrieved <span class="nowrap">18 March</span> 2024</span>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=unknown&amp;rft.btitle=What+is+the+difference+between+anhydrous+glucose+and+glucose&amp;rft_id=https%3A%2F%2Ftopic.echemi.com%2Fa%2Fwhat-is-the-difference-between-anhydrous-glucose-and-glucose_176447.html&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AGlucose" class="Z3988"></span></span> </li> <li id="cite_note-44"><span class="mw-cite-backlink"><b><a href="#cite_ref-44">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://thisvsthat.io/anhydrous-vs-monohydrate">"Anhydrous vs. Monohydrate - What's the Difference?"</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20240318215004/https://thisvsthat.io/anhydrous-vs-monohydrate">Archived</a> from the original on 18 March 2024<span class="reference-accessdate">. Retrieved <span class="nowrap">18 March</span> 2024</span>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=unknown&amp;rft.btitle=Anhydrous+vs.+Monohydrate+-+What%27s+the+Difference%3F&amp;rft_id=https%3A%2F%2Fthisvsthat.io%2Fanhydrous-vs-monohydrate&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AGlucose" class="Z3988"></span></span> </li> <li id="cite_note-45"><span class="mw-cite-backlink"><b><a href="#cite_ref-45">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFTrasiBoerrigterByrnCarvajal2011" class="citation journal cs1">Trasi NS, Boerrigter SX, Byrn SR, Carvajal TM (15 March 2011). 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Retrieved <span class="nowrap">18 March</span> 2024</span>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=unknown&amp;rft.btitle=D-Glucose&amp;rft_id=https%3A%2F%2Fpubchem.ncbi.nlm.nih.gov%2Fcompound%2F5793&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AGlucose" class="Z3988"></span></span> </li> <li id="cite_note-51"><span class="mw-cite-backlink"><b><a href="#cite_ref-51">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.sigmaaldrich.com/MD/en/product/mm/137048">"D-(+)-Glucose"</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20240318213459/https://www.sigmaaldrich.com/US/en/product/mm/137048">Archived</a> from the original on 18 March 2024<span class="reference-accessdate">. Retrieved <span class="nowrap">18 March</span> 2024</span>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=unknown&amp;rft.btitle=D-%28%2B%29-Glucose&amp;rft_id=https%3A%2F%2Fwww.sigmaaldrich.com%2FMD%2Fen%2Fproduct%2Fmm%2F137048&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AGlucose" class="Z3988"></span></span> </li> <li id="cite_note-52"><span class="mw-cite-backlink"><b><a href="#cite_ref-52">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.sigmaaldrich.com/MD/en/product/mm/108337">"D-(+)-Glucose"</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20240318213357/https://www.sigmaaldrich.com/US/en/product/mm/108337">Archived</a> from the original on 18 March 2024<span class="reference-accessdate">. Retrieved <span class="nowrap">18 March</span> 2024</span>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=unknown&amp;rft.btitle=D-%28%2B%29-Glucose&amp;rft_id=https%3A%2F%2Fwww.sigmaaldrich.com%2FMD%2Fen%2Fproduct%2Fmm%2F108337&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AGlucose" class="Z3988"></span></span> </li> <li id="cite_note-chem2-53"><span class="mw-cite-backlink"><b><a href="#cite_ref-chem2_53-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://chem.libretexts.org/Bookshelves/Biological_Chemistry/Supplemental_Modules_%28Biological_Chemistry%29/Carbohydrates/Monosaccharides/Glucose_%28Dextrose%29">"Glucose (Dextrose)"</a>. 2 October 2013. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20231221223258/https://chem.libretexts.org/Bookshelves/Biological_Chemistry/Supplemental_Modules_(Biological_Chemistry)/Carbohydrates/Monosaccharides/Glucose_(Dextrose)">Archived</a> from the original on 21 December 2023<span class="reference-accessdate">. Retrieved <span class="nowrap">18 March</span> 2024</span>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=unknown&amp;rft.btitle=Glucose+%28Dextrose%29&amp;rft.date=2013-10-02&amp;rft_id=https%3A%2F%2Fchem.libretexts.org%2FBookshelves%2FBiological_Chemistry%2FSupplemental_Modules_%2528Biological_Chemistry%2529%2FCarbohydrates%2FMonosaccharides%2FGlucose_%2528Dextrose%2529&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AGlucose" class="Z3988"></span></span> </li> <li id="cite_note-Ullmann-54"><span class="mw-cite-backlink">^ <a href="#cite_ref-Ullmann_54-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Ullmann_54-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSchenck2006" class="citation book cs1">Schenck FW (2006). "Glucose and Glucose-Containing Syrups". <i>Ullmann's Encyclopedia of Industrial Chemistry</i>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F14356007.a12_457.pub2">10.1002/14356007.a12_457.pub2</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a>&#160;<a href="/wiki/Special:BookSources/978-3-527-30673-2" title="Special:BookSources/978-3-527-30673-2"><bdi>978-3-527-30673-2</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=bookitem&amp;rft.atitle=Glucose+and+Glucose-Containing+Syrups&amp;rft.btitle=Ullmann%27s+Encyclopedia+of+Industrial+Chemistry&amp;rft.date=2006&amp;rft_id=info%3Adoi%2F10.1002%2F14356007.a12_457.pub2&amp;rft.isbn=978-3-527-30673-2&amp;rft.aulast=Schenck&amp;rft.aufirst=Fred+W.&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AGlucose" class="Z3988"></span></span> </li> <li id="cite_note-pf-55"><span class="mw-cite-backlink">^ <a href="#cite_ref-pf_55-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-pf_55-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text">Patrick F. Fox: <i>Advanced Dairy Chemistry Volume 3: Lactose, water, salts and vitamins</i>, Springer, 1992. Volume 3, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a>&#160;<a href="/wiki/Special:BookSources/9780412630200" title="Special:BookSources/9780412630200">9780412630200</a>. p. 316.</span> </li> <li id="cite_note-Caballero_1_76-56"><span class="mw-cite-backlink"><b><a href="#cite_ref-Caballero_1_76_56-0">^</a></b></span> <span class="reference-text">Benjamin Caballero, Paul Finglas, Fidel Toldrá: <i>Encyclopedia of Food and Health</i>. Academic Press (2016). <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a>&#160;<a href="/wiki/Special:BookSources/9780123849533" title="Special:BookSources/9780123849533">9780123849533</a>, Volume 1, p. 76.</span> </li> <li id="cite_note-57"><span class="mw-cite-backlink"><b><a href="#cite_ref-57">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://chem.libretexts.org/Bookshelves/Introductory_Chemistry/Basics_of_General_Organic_and_Biological_Chemistry_(Ball_et_al.)/16%3A_Carbohydrates/16.04%3A_Cyclic_Structures_of_Monosaccharides">"16.4: Cyclic Structures of Monosaccharides"</a>. <i>Chemistry LibreTexts</i>. 18 July 2014. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20230417213903/https://chem.libretexts.org/Bookshelves/Introductory_Chemistry/Basics_of_General_Organic_and_Biological_Chemistry_(Ball_et_al.)/16:_Carbohydrates/16.04:_Cyclic_Structures_of_Monosaccharides">Archived</a> from the original on 17 April 2023<span class="reference-accessdate">. Retrieved <span class="nowrap">17 April</span> 2023</span>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=unknown&amp;rft.jtitle=Chemistry+LibreTexts&amp;rft.atitle=16.4%3A+Cyclic+Structures+of+Monosaccharides&amp;rft.date=2014-07-18&amp;rft_id=https%3A%2F%2Fchem.libretexts.org%2FBookshelves%2FIntroductory_Chemistry%2FBasics_of_General_Organic_and_Biological_Chemistry_%28Ball_et_al.%29%2F16%253A_Carbohydrates%2F16.04%253A_Cyclic_Structures_of_Monosaccharides&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AGlucose" class="Z3988"></span></span> </li> <li id="cite_note-taka1979-58"><span class="mw-cite-backlink"><b><a href="#cite_ref-taka1979_58-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFTakagiJeffrey1979" class="citation journal cs1">Takagi S, Jeffrey GA (1979). "1,2-O-isopropylidene-D-glucofuranose". <i>Acta Crystallographica Section B</i>. <b>B35</b> (6): 1522–1525. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/1979AcCrB..35.1522T">1979AcCrB..35.1522T</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1107%2FS0567740879006968">10.1107/S0567740879006968</a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=Acta+Crystallographica+Section+B&amp;rft.atitle=1%2C2-O-isopropylidene-D-glucofuranose&amp;rft.volume=B35&amp;rft.issue=6&amp;rft.pages=1522-1525&amp;rft.date=1979&amp;rft_id=info%3Adoi%2F10.1107%2FS0567740879006968&amp;rft_id=info%3Abibcode%2F1979AcCrB..35.1522T&amp;rft.aulast=Takagi&amp;rft.aufirst=S.&amp;rft.au=Jeffrey%2C+G.+A.&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AGlucose" class="Z3988"></span></span> </li> <li id="cite_note-biel1999-59"><span class="mw-cite-backlink"><b><a href="#cite_ref-biel1999_59-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBieleckiEggertChristian_Norrild1999" class="citation journal cs1">Bielecki M, Eggert H, Christian Norrild J (1999). "A fluorescent glucose sensor binding covalently to all five hydroxy groups of α-D-glucofuranose. A reinvestigation". <i>Journal of the Chemical Society, Perkin Transactions</i>. <b>2</b> (3): 449–456. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1039%2FA808896I">10.1039/A808896I</a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=Journal+of+the+Chemical+Society%2C+Perkin+Transactions&amp;rft.atitle=A+fluorescent+glucose+sensor+binding+covalently+to+all+five+hydroxy+groups+of+%CE%B1-D-glucofuranose.+A+reinvestigation&amp;rft.volume=2&amp;rft.issue=3&amp;rft.pages=449-456&amp;rft.date=1999&amp;rft_id=info%3Adoi%2F10.1039%2FA808896I&amp;rft.aulast=Bielecki&amp;rft.aufirst=Mia&amp;rft.au=Eggert%2C+Hanne&amp;rft.au=Christian+Norrild%2C+Jens&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AGlucose" class="Z3988"></span></span> </li> <li id="cite_note-chan2006-60"><span class="mw-cite-backlink"><b><a href="#cite_ref-chan2006_60-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFChandranNangia2006" class="citation journal cs1">Chandran SK, Nangia A (2006). "Modulated crystal structure (Z<span class="nowrap" style="padding-left:0.15em;">′</span> = 2) of α-d-glucofuranose-1,2:3,5-bis(p-tolyl)boronate". <i>CrystEngComm</i>. <b>8</b> (8): 581–585. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1039%2FB608029D">10.1039/B608029D</a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=CrystEngComm&amp;rft.atitle=Modulated+crystal+structure+%28Z%3Cspan+class%3D%22nowrap%22+style%3D%22padding-left%3A0.15em%3B%22%3E%E2%80%B2%3C%2Fspan%3E+%3D+2%29+of+%CE%B1-d-glucofuranose-1%2C2%3A3%2C5-bis%28p-tolyl%29boronate&amp;rft.volume=8&amp;rft.issue=8&amp;rft.pages=581-585&amp;rft.date=2006&amp;rft_id=info%3Adoi%2F10.1039%2FB608029D&amp;rft.aulast=Chandran&amp;rft.aufirst=Sreekanth+K.&amp;rft.au=Nangia%2C+Ashwini&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AGlucose" class="Z3988"></span></span> </li> <li id="cite_note-61"><span class="mw-cite-backlink"><b><a href="#cite_ref-61">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMcMurry1988" class="citation cs2"><a href="/wiki/John_E._McMurry" title="John E. 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Endocrinology and Metabolism</i>. <b>296</b> (1): E11–21. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1152%2Fajpendo.90563.2008">10.1152/ajpendo.90563.2008</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a>&#160;<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2636990">2636990</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a>&#160;<a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/18840763">18840763</a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=American+Journal+of+Physiology.+Endocrinology+and+Metabolism&amp;rft.atitle=Four+grams+of+glucose&amp;rft.volume=296&amp;rft.issue=1&amp;rft.pages=E11-21&amp;rft.date=2009&amp;rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC2636990%23id-name%3DPMC&amp;rft_id=info%3Apmid%2F18840763&amp;rft_id=info%3Adoi%2F10.1152%2Fajpendo.90563.2008&amp;rft.aulast=Wasserman&amp;rft.aufirst=D.+H.&amp;rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC2636990&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AGlucose" class="Z3988"></span></span> </li> <li id="cite_note-73"><span class="mw-cite-backlink"><b><a href="#cite_ref-73">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation cs2"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20131014173838/http://forecast.diabetes.org/magazine/features/high-blood-glucose-and-diabetes-complications">"High Blood Glucose and Diabetes Complications: The buildup of molecules known as AGEs may be the key link"</a>, <i>Diabetes Forecast</i>, American Diabetes Association, 2010, <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a>&#160;<a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0095-8301">0095-8301</a>, archived from <a rel="nofollow" class="external text" href="http://forecast.diabetes.org/magazine/features/high-blood-glucose-and-diabetes-complications">the original</a> on 14 October 2013<span class="reference-accessdate">, retrieved <span class="nowrap">20 May</span> 2010</span></cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=Diabetes+Forecast&amp;rft.atitle=High+Blood+Glucose+and+Diabetes+Complications%3A+The+buildup+of+molecules+known+as+AGEs+may+be+the+key+link&amp;rft.date=2010&amp;rft.issn=0095-8301&amp;rft_id=http%3A%2F%2Fforecast.diabetes.org%2Fmagazine%2Ffeatures%2Fhigh-blood-glucose-and-diabetes-complications&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AGlucose" class="Z3988"></span></span> </li> <li id="cite_note-varki-74"><span class="mw-cite-backlink"><b><a href="#cite_ref-varki_74-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFVarkiCummingsEskoFreeze2009" class="citation book cs1">Varki A, Cummings RD, Esko JD, Freeze HH, Stanley P, Bertozzi CR, et&#160;al. 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Cold Spring Harbor Laboratories Press. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a>&#160;<a href="/wiki/Special:BookSources/978-0-87969-770-9" title="Special:BookSources/978-0-87969-770-9"><bdi>978-0-87969-770-9</bdi></a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a>&#160;<a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/20301239">20301239</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20161206081633/https://www.ncbi.nlm.nih.gov/books/NBK1908/">Archived</a> from the original on 6 December 2016.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=book&amp;rft.btitle=Essentials+of+Glycobiology&amp;rft.edition=2nd&amp;rft.pub=Cold+Spring+Harbor+Laboratories+Press&amp;rft.date=2009&amp;rft_id=info%3Apmid%2F20301239&amp;rft.isbn=978-0-87969-770-9&amp;rft.aulast=Varki&amp;rft.aufirst=A.&amp;rft.au=Cummings%2C+R.+D.&amp;rft.au=Esko%2C+J.+D.&amp;rft.au=Freeze%2C+H.+H.&amp;rft.au=Stanley%2C+P.&amp;rft.au=Bertozzi%2C+C.+R.&amp;rft.au=Hart%2C+G.+W.&amp;rft.au=Etzler%2C+M.+E.&amp;rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fbooks%2FNBK1908%2F&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AGlucose" class="Z3988"></span></span> </li> <li id="cite_note-fca-75"><span class="mw-cite-backlink"><b><a href="#cite_ref-fca_75-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://foodb.ca/compounds/FDB012530">"Showing Compound D-Glucose (FDB012530) - FooDB"</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20221206084746/https://www.foodb.ca/compounds/FDB012530">Archived</a> from the original on 6 December 2022<span class="reference-accessdate">. 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Volume 6, p. 48.</span> </li> <li id="cite_note-ResSoc-138"><span class="mw-cite-backlink">^ <a href="#cite_ref-ResSoc_138-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-ResSoc_138-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-ResSoc_138-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text">The Amylase Research Society of Japan: <i>Handbook of Amylases and Related Enzymes.</i> Elsevier, 2014, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a>&#160;<a href="/wiki/Special:BookSources/978-1-483-29939-6" title="Special:BookSources/978-1-483-29939-6">978-1-483-29939-6</a>, p.&#160;195.</span> </li> <li id="cite_note-Madsen-139"><span class="mw-cite-backlink"><b><a href="#cite_ref-Madsen_139-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMadsenNormanSlott1973" class="citation journal cs1">Madsen GB, Norman BE, Slott S (1973). 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Volume 8, Issue 3, 1884, p.&#160;175–185 <a rel="nofollow" class="external text" href="http://www.degruyter.com/dg/viewarticle/j$002fbchm1.1884.8.issue-3$002fbchm1.1884.8.3.175$002fbchm1.1884.8.3.175.xml">Abstract</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20150923213720/http://www.degruyter.com/dg/viewarticle/j$002fbchm1.1884.8.issue-3$002fbchm1.1884.8.3.175$002fbchm1.1884.8.3.175.xml">Archived</a> 23 September 2015 at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a> (in German).</span> </li> <li id="cite_note-Schwedt_102-156"><span class="mw-cite-backlink">^ <a href="#cite_ref-Schwedt_102_156-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Schwedt_102_156-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Schwedt_102_156-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-Schwedt_102_156-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-Schwedt_102_156-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-Schwedt_102_156-5"><sup><i><b>f</b></i></sup></a> <a href="#cite_ref-Schwedt_102_156-6"><sup><i><b>g</b></i></sup></a> <a href="#cite_ref-Schwedt_102_156-7"><sup><i><b>h</b></i></sup></a> <a href="#cite_ref-Schwedt_102_156-8"><sup><i><b>i</b></i></sup></a></span> <span class="reference-text">Georg Schwedt: <i>Zuckersüße Chemie</i>. 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this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Glycolysis" title="Template talk:Glycolysis"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Glycolysis" title="Special:EditPage/Template:Glycolysis"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Glycolysis_metabolic_pathway" style="font-size:114%;margin:0 4em"><a href="/wiki/Glycolysis" title="Glycolysis">Glycolysis</a> <a href="/wiki/Metabolic_pathway" title="Metabolic pathway">metabolic pathway</a></div></th></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0;border-width:0;"><div style="padding:0"><div style="background: transparent; padding: 2px 0 0 0; display: flex; flex-flow: row wrap;"> <div style="text-align: center; display: inline-block; display: inline-flex; flex-flow: column; flex: 1; vertical-align:top;"><div style="width: 100%; display: block; background-color:lightgreen;"> <p style="margin: 0.1em 0.5em;"><a class="mw-selflink selflink">Glucose</a></p> </div><div style="margin: auto 0"><span typeof="mw:File"><a href="/wiki/File:D-glucose_wpmp.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/3e/D-glucose_wpmp.svg/70px-D-glucose_wpmp.svg.png" decoding="async" width="70" height="70" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/3e/D-glucose_wpmp.svg/105px-D-glucose_wpmp.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/3e/D-glucose_wpmp.svg/140px-D-glucose_wpmp.svg.png 2x" data-file-width="128" data-file-height="128" /></a></span></div> </div> <div style="text-align: center; display: inline-block; display: inline-flex; flex-flow: column; flex: 1; vertical-align:top;"><div style="width: 100%; display: block; background-color:#ffcccc;"> <p style="margin: 0.1em 0.5em;"><a href="/wiki/Hexokinase" title="Hexokinase">Hexokinase</a></p> </div><div style="line-height: 1; flex: 1 0 auto; display: flex; flex-flow: row wrap; justify-content: space-around; align-items: flex-end;"><div style="width: 45%; float:left">ATP</div> <div style="width: 45%; float:right">ADP</div> </div><div style="width: 100%; clear:both; overflow: hidden; height: 27px;"><div style=""><span typeof="mw:File"><a href="/wiki/File:Biochem_reaction_arrow_forward_YYNN_horiz_med.svg" class="mw-file-description" title="Rightward reaction arrow with minor substrate(s) from top left and minor product(s) to top right"><img alt="Rightward reaction arrow with minor substrate(s) from top left and minor product(s) to top right" src="//upload.wikimedia.org/wikipedia/commons/thumb/8/85/Biochem_reaction_arrow_forward_YYNN_horiz_med.svg/45px-Biochem_reaction_arrow_forward_YYNN_horiz_med.svg.png" decoding="async" width="45" height="45" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/85/Biochem_reaction_arrow_forward_YYNN_horiz_med.svg/68px-Biochem_reaction_arrow_forward_YYNN_horiz_med.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/85/Biochem_reaction_arrow_forward_YYNN_horiz_med.svg/90px-Biochem_reaction_arrow_forward_YYNN_horiz_med.svg.png 2x" data-file-width="75" data-file-height="75" /></a></span></div></div><div style="line-height: 1; flex: 1 0 auto; display: flex; flex-flow: row wrap; justify-content: space-around; min-height: 22.5px;"></div> </div> <div style="text-align: center; display: inline-block; display: inline-flex; flex-flow: column; flex: 1; vertical-align:top;"><div style="width: 100%; display: block; background-color:lightgreen;"> <p style="margin: 0.1em 0.5em;"><a href="/wiki/Glucose_6-phosphate" title="Glucose 6-phosphate">Glucose 6-phosphate</a></p> </div><div style="margin: auto 0"><span typeof="mw:File"><a href="/wiki/File:Alpha-D-glucose-6-phosphate_wpmp.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/80/Alpha-D-glucose-6-phosphate_wpmp.svg/70px-Alpha-D-glucose-6-phosphate_wpmp.svg.png" decoding="async" width="70" height="109" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/80/Alpha-D-glucose-6-phosphate_wpmp.svg/105px-Alpha-D-glucose-6-phosphate_wpmp.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/80/Alpha-D-glucose-6-phosphate_wpmp.svg/140px-Alpha-D-glucose-6-phosphate_wpmp.svg.png 2x" data-file-width="119" data-file-height="186" /></a></span></div> </div> <div style="text-align: center; display: inline-block; display: inline-flex; flex-flow: column; flex: 1; vertical-align:top;"><div style="width: 100%; display: block; background-color:#ffcccc;"> <p style="margin: 0.1em 0.5em;"><a href="/wiki/Glucose-6-phosphate_isomerase" title="Glucose-6-phosphate isomerase">Glucose-6-phosphate<br />isomerase</a></p> </div><div style="line-height: 1; flex: 1 0 auto; display: flex; flex-flow: row wrap; justify-content: space-around; align-items: flex-end; min-height: 22.5px;"> </div><div style="width: 100%; clear:both; overflow: hidden; height: 9px;"><div style="position: relative; bottom: 18px;"><span typeof="mw:File"><a href="/wiki/File:Biochem_reaction_arrow_reversible_NNNN_horiz_med.svg" class="mw-file-description" title="Reversible left-right reaction arrow"><img alt="Reversible left-right reaction arrow" src="//upload.wikimedia.org/wikipedia/commons/thumb/7/70/Biochem_reaction_arrow_reversible_NNNN_horiz_med.svg/45px-Biochem_reaction_arrow_reversible_NNNN_horiz_med.svg.png" decoding="async" width="45" height="45" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/70/Biochem_reaction_arrow_reversible_NNNN_horiz_med.svg/68px-Biochem_reaction_arrow_reversible_NNNN_horiz_med.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/70/Biochem_reaction_arrow_reversible_NNNN_horiz_med.svg/90px-Biochem_reaction_arrow_reversible_NNNN_horiz_med.svg.png 2x" data-file-width="75" data-file-height="75" /></a></span></div></div><div style="line-height: 1; flex: 1 0 auto; display: flex; flex-flow: row wrap; justify-content: space-around; min-height: 22.5px;"></div> </div> <div style="text-align: center; display: inline-block; display: inline-flex; flex-flow: column; flex: 1; vertical-align:top;"><div style="width: 100%; display: block; background-color:lightgreen;"> <p style="margin: 0.1em 0.5em;"><a href="/wiki/Fructose_6-phosphate" title="Fructose 6-phosphate">Fructose 6-phosphate</a></p> </div><div style="margin: auto 0"><span typeof="mw:File"><a href="/wiki/File:Beta-D-Fructose-6-phosphat2.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a0/Beta-D-Fructose-6-phosphat2.svg/100px-Beta-D-Fructose-6-phosphat2.svg.png" decoding="async" width="100" height="109" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a0/Beta-D-Fructose-6-phosphat2.svg/150px-Beta-D-Fructose-6-phosphat2.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a0/Beta-D-Fructose-6-phosphat2.svg/200px-Beta-D-Fructose-6-phosphat2.svg.png 2x" data-file-width="180" data-file-height="197" /></a></span></div> </div> <div style="text-align: center; display: inline-block; display: inline-flex; flex-flow: column; flex: 1; vertical-align:top;"><div style="width: 100%; display: block; background-color:#ffcccc;"> <p style="margin: 0.1em 0.5em;"><a href="/wiki/Phosphofructokinase-1" class="mw-redirect" title="Phosphofructokinase-1">Phosphofructokinase-1</a></p> </div><div style="line-height: 1; flex: 1 0 auto; display: flex; flex-flow: row wrap; justify-content: space-around; align-items: flex-end;"><div style="width: 45%; float:left">ATP</div> <div style="width: 45%; float:right">ADP</div> </div><div style="width: 100%; clear:both; overflow: hidden; height: 27px;"><div style=""><span typeof="mw:File"><a href="/wiki/File:Biochem_reaction_arrow_forward_YYNN_horiz_med.svg" class="mw-file-description" title="Rightward reaction arrow with minor substrate(s) from top left and minor product(s) to top right"><img alt="Rightward reaction arrow with minor substrate(s) from top left and minor product(s) to top right" src="//upload.wikimedia.org/wikipedia/commons/thumb/8/85/Biochem_reaction_arrow_forward_YYNN_horiz_med.svg/45px-Biochem_reaction_arrow_forward_YYNN_horiz_med.svg.png" decoding="async" width="45" height="45" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/85/Biochem_reaction_arrow_forward_YYNN_horiz_med.svg/68px-Biochem_reaction_arrow_forward_YYNN_horiz_med.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/85/Biochem_reaction_arrow_forward_YYNN_horiz_med.svg/90px-Biochem_reaction_arrow_forward_YYNN_horiz_med.svg.png 2x" data-file-width="75" data-file-height="75" /></a></span></div></div><div style="line-height: 1; flex: 1 0 auto; display: flex; flex-flow: row wrap; justify-content: space-around; min-height: 22.5px;"></div> </div> <div style="text-align: center; display: inline-block; display: inline-flex; flex-flow: column; flex: 1; vertical-align:top;"><div style="width: 100%; display: block; background-color:lightgreen;"> <p style="margin: 0.1em 0.5em;"><a href="/wiki/Fructose_1,6-bisphosphate" title="Fructose 1,6-bisphosphate">Fructose 1,6-bisphosphate</a></p> </div><div style="margin: auto 0"><span typeof="mw:File"><a href="/wiki/File:Beta-D-Fructose-1,6-bisphosphat2.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/5e/Beta-D-Fructose-1%2C6-bisphosphat2.svg/100px-Beta-D-Fructose-1%2C6-bisphosphat2.svg.png" decoding="async" width="100" height="109" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/5e/Beta-D-Fructose-1%2C6-bisphosphat2.svg/150px-Beta-D-Fructose-1%2C6-bisphosphat2.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/5e/Beta-D-Fructose-1%2C6-bisphosphat2.svg/200px-Beta-D-Fructose-1%2C6-bisphosphat2.svg.png 2x" data-file-width="180" data-file-height="197" /></a></span></div> </div> <div style="text-align: center; display: inline-block; display: inline-flex; flex-flow: column; flex: 1; vertical-align:top;"><div style="width: 100%; display: block; background-color:#ffcccc;"> <p style="margin: 0.1em 0.5em;"><a href="/wiki/Fructose-bisphosphate_aldolase" title="Fructose-bisphosphate aldolase">Fructose-bisphosphate<br />aldolase</a></p> </div><div style="line-height: 1; flex: 1 0 auto; display: flex; flex-flow: row wrap; justify-content: space-around; align-items: flex-end; min-height: 22.5px;"> </div><div style="width: 100%; clear:both; overflow: hidden; height: 9px;"><div style="position: relative; bottom: 18px;"><span typeof="mw:File"><a href="/wiki/File:Biochem_reaction_arrow_reversible_NNNN_horiz_med.svg" class="mw-file-description" title="Reversible left-right reaction arrow"><img alt="Reversible left-right reaction arrow" src="//upload.wikimedia.org/wikipedia/commons/thumb/7/70/Biochem_reaction_arrow_reversible_NNNN_horiz_med.svg/45px-Biochem_reaction_arrow_reversible_NNNN_horiz_med.svg.png" decoding="async" width="45" height="45" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/70/Biochem_reaction_arrow_reversible_NNNN_horiz_med.svg/68px-Biochem_reaction_arrow_reversible_NNNN_horiz_med.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/70/Biochem_reaction_arrow_reversible_NNNN_horiz_med.svg/90px-Biochem_reaction_arrow_reversible_NNNN_horiz_med.svg.png 2x" data-file-width="75" data-file-height="75" /></a></span></div></div><div style="line-height: 1; flex: 1 0 auto; display: flex; flex-flow: row wrap; justify-content: space-around; min-height: 22.5px;"></div> </div> <div style="text-align: center; display: inline-block; display: inline-flex; flex-flow: column; flex: 1; vertical-align:top;"><div style="width: 100%; display: block; background-color:lightgreen;"> <p style="margin: 0.1em 0.5em;"><a href="/wiki/Dihydroxyacetone_phosphate" title="Dihydroxyacetone phosphate">Dihydroxyacetone phosphate</a></p> </div><div style="margin: auto 0"><span typeof="mw:File"><a href="/wiki/File:Glycerone-phosphate_wpmp.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/3f/Glycerone-phosphate_wpmp.svg/70px-Glycerone-phosphate_wpmp.svg.png" decoding="async" width="70" height="131" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/3f/Glycerone-phosphate_wpmp.svg/105px-Glycerone-phosphate_wpmp.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/3f/Glycerone-phosphate_wpmp.svg/140px-Glycerone-phosphate_wpmp.svg.png 2x" data-file-width="81" data-file-height="152" /></a></span></div> </div> <div style="text-align: center; display: inline-block; display: inline-flex; flex-flow: column; flex: 1; vertical-align:top;"><div style="width: 100%; display: block;"> <p style="margin: 0.1em 0.5em;">+</p> </div><div style="margin: auto 0">+</div> </div> <div style="text-align: center; display: inline-block; display: inline-flex; flex-flow: column; flex: 1; vertical-align:top;"><div style="width: 100%; display: block; background-color:lightgreen;"> <p style="margin: 0.1em 0.5em;"><a href="/wiki/Glyceraldehyde_3-phosphate" title="Glyceraldehyde 3-phosphate">Glyceraldehyde 3-phosphate</a></p> </div><div style="margin: auto 0"><span typeof="mw:File"><a href="/wiki/File:D-glyceraldehyde-3-phosphate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/3a/D-glyceraldehyde-3-phosphate.svg/70px-D-glyceraldehyde-3-phosphate.svg.png" decoding="async" width="70" height="98" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/3a/D-glyceraldehyde-3-phosphate.svg/105px-D-glyceraldehyde-3-phosphate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/3a/D-glyceraldehyde-3-phosphate.svg/140px-D-glyceraldehyde-3-phosphate.svg.png 2x" data-file-width="512" data-file-height="718" /></a></span></div> </div> <div style="text-align: center; display: inline-block; display: inline-flex; flex-flow: column; flex: 1; vertical-align:top;"><div style="width: 100%; display: block; background-color:#ffcccc;"> <p style="margin: 0.1em 0.5em;"><a href="/wiki/Triosephosphate_isomerase" title="Triosephosphate isomerase">Triosephosphate<br />isomerase</a></p> </div><div style="line-height: 1; flex: 1 0 auto; display: flex; flex-flow: row wrap; justify-content: space-around; align-items: flex-end; min-height: 22.5px;"> </div><div style="width: 100%; clear:both; overflow: hidden; height: 9px;"><div style="position: relative; bottom: 18px;"><span typeof="mw:File"><a href="/wiki/File:Biochem_reaction_arrow_reversible_NNNN_horiz_med.svg" class="mw-file-description" title="Reversible left-right reaction arrow"><img alt="Reversible left-right reaction arrow" src="//upload.wikimedia.org/wikipedia/commons/thumb/7/70/Biochem_reaction_arrow_reversible_NNNN_horiz_med.svg/45px-Biochem_reaction_arrow_reversible_NNNN_horiz_med.svg.png" decoding="async" width="45" height="45" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/70/Biochem_reaction_arrow_reversible_NNNN_horiz_med.svg/68px-Biochem_reaction_arrow_reversible_NNNN_horiz_med.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/70/Biochem_reaction_arrow_reversible_NNNN_horiz_med.svg/90px-Biochem_reaction_arrow_reversible_NNNN_horiz_med.svg.png 2x" data-file-width="75" data-file-height="75" /></a></span></div></div><div style="line-height: 1; flex: 1 0 auto; display: flex; flex-flow: row wrap; justify-content: space-around; min-height: 22.5px;"></div> </div> <div style="text-align: center; display: inline-block; display: inline-flex; flex-flow: column; flex: 1; vertical-align:top;"><div style="width: 100%; display: block; background-color:lightgreen;"> <p style="margin: 0.1em 0.5em;"><strong>2 × </strong><a href="/wiki/Glyceraldehyde_3-phosphate" title="Glyceraldehyde 3-phosphate">Glyceraldehyde 3-phosphate</a></p> </div><div style="margin: auto 0"><strong>2&#160;×&#160;</strong> <span typeof="mw:File"><a href="/wiki/File:D-glyceraldehyde-3-phosphate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/3a/D-glyceraldehyde-3-phosphate.svg/70px-D-glyceraldehyde-3-phosphate.svg.png" decoding="async" width="70" height="98" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/3a/D-glyceraldehyde-3-phosphate.svg/105px-D-glyceraldehyde-3-phosphate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/3a/D-glyceraldehyde-3-phosphate.svg/140px-D-glyceraldehyde-3-phosphate.svg.png 2x" data-file-width="512" data-file-height="718" /></a></span></div> </div> <div style="text-align: center; display: inline-block; display: inline-flex; flex-flow: column; flex: 1; vertical-align:top;"><div style="width: 100%; display: block; background-color:#ffcccc;"> <p style="margin: 0.1em 0.5em;"><a href="/wiki/Glyceraldehyde-3-phosphate_dehydrogenase" class="mw-redirect" title="Glyceraldehyde-3-phosphate dehydrogenase">Glyceraldehyde-3-phosphate<br />dehydrogenase</a></p> </div><div style="line-height: 1; flex: 1 0 auto; display: flex; flex-flow: row wrap; justify-content: space-around; align-items: flex-end;"><div style="width: 45%; float:left">NAD<sup>+</sup>+ P<sub>i</sub></div> <div style="width: 45%; float:right">NADH + H<sup>+</sup></div> </div><div style="width: 100%; clear:both; overflow: hidden; height: 45px;"><div style=""><span typeof="mw:File"><a href="/wiki/File:Biochem_reaction_arrow_reversible_YYYY_horiz_med.svg" class="mw-file-description" title="Reversible left-right reaction arrow with minor forward substrate(s) from top left, minor forward product(s) to top right, minor reverse substrate(s) from bottom right and minor reverse product(s) to bottom left"><img alt="Reversible left-right reaction arrow with minor forward substrate(s) from top left, minor forward product(s) to top right, minor reverse substrate(s) from bottom right and minor reverse product(s) to bottom left" src="//upload.wikimedia.org/wikipedia/commons/thumb/1/19/Biochem_reaction_arrow_reversible_YYYY_horiz_med.svg/45px-Biochem_reaction_arrow_reversible_YYYY_horiz_med.svg.png" decoding="async" width="45" height="45" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/19/Biochem_reaction_arrow_reversible_YYYY_horiz_med.svg/68px-Biochem_reaction_arrow_reversible_YYYY_horiz_med.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/19/Biochem_reaction_arrow_reversible_YYYY_horiz_med.svg/90px-Biochem_reaction_arrow_reversible_YYYY_horiz_med.svg.png 2x" data-file-width="75" data-file-height="75" /></a></span></div></div><div style="line-height: 1; flex: 1 0 auto; display: flex; flex-flow: row wrap; justify-content: space-around;"><div style="width: 45%; float:left">NAD<sup>+</sup>+ P<sub>i</sub></div> <div style="width: 45%; float:right">NADH + H<sup>+</sup></div><div style="clear:both;" class=""></div></div> </div> <div style="text-align: center; display: inline-block; display: inline-flex; flex-flow: column; flex: 1; vertical-align:top;"><div style="width: 100%; display: block; background-color:lightgreen;"> <p style="margin: 0.1em 0.5em;"><strong>2 × </strong><a href="/wiki/1,3-Bisphosphoglycerate" class="mw-redirect" title="1,3-Bisphosphoglycerate">1,3-Bisphosphoglycerate</a></p> </div><div style="margin: auto 0"><strong>2&#160;×&#160;</strong> <span typeof="mw:File"><a href="/wiki/File:1,3-bisphospho-D-glycerate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/75/1%2C3-bisphospho-D-glycerate.svg/70px-1%2C3-bisphospho-D-glycerate.svg.png" decoding="async" width="70" height="125" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/75/1%2C3-bisphospho-D-glycerate.svg/105px-1%2C3-bisphospho-D-glycerate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/75/1%2C3-bisphospho-D-glycerate.svg/140px-1%2C3-bisphospho-D-glycerate.svg.png 2x" data-file-width="222" data-file-height="396" /></a></span></div> </div> <div style="text-align: center; display: inline-block; display: inline-flex; flex-flow: column; flex: 1; vertical-align:top;"><div style="width: 100%; display: block; background-color:#ffcccc;"> <p style="margin: 0.1em 0.5em;"><a href="/wiki/Phosphoglycerate_kinase" title="Phosphoglycerate kinase">Phosphoglycerate kinase</a></p> </div><div style="line-height: 1; flex: 1 0 auto; display: flex; flex-flow: row wrap; justify-content: space-around; align-items: flex-end;"><div style="width: 45%; float:left">ADP</div> <div style="width: 45%; float:right">ATP</div> </div><div style="width: 100%; clear:both; overflow: hidden; height: 45px;"><div style=""><span typeof="mw:File"><a href="/wiki/File:Biochem_reaction_arrow_reversible_YYYY_horiz_med.svg" class="mw-file-description" title="Reversible left-right reaction arrow with minor forward substrate(s) from top left, minor forward product(s) to top right, minor reverse substrate(s) from bottom right and minor reverse product(s) to bottom left"><img alt="Reversible left-right reaction arrow with minor forward substrate(s) from top left, minor forward product(s) to top right, minor reverse substrate(s) from bottom right and minor reverse product(s) to bottom left" src="//upload.wikimedia.org/wikipedia/commons/thumb/1/19/Biochem_reaction_arrow_reversible_YYYY_horiz_med.svg/45px-Biochem_reaction_arrow_reversible_YYYY_horiz_med.svg.png" decoding="async" width="45" height="45" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/19/Biochem_reaction_arrow_reversible_YYYY_horiz_med.svg/68px-Biochem_reaction_arrow_reversible_YYYY_horiz_med.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/19/Biochem_reaction_arrow_reversible_YYYY_horiz_med.svg/90px-Biochem_reaction_arrow_reversible_YYYY_horiz_med.svg.png 2x" data-file-width="75" data-file-height="75" /></a></span></div></div><div style="line-height: 1; flex: 1 0 auto; display: flex; flex-flow: row wrap; justify-content: space-around;"><div style="width: 45%; float:left">ADP</div> <div style="width: 45%; float:right">ATP</div><div style="clear:both;" class=""></div></div> </div> <div style="text-align: center; display: inline-block; display: inline-flex; flex-flow: column; flex: 1; vertical-align:top;"><div style="width: 100%; display: block; background-color:lightgreen;"> <p style="margin: 0.1em 0.5em;"><strong>2 × </strong><a href="/wiki/3-Phosphoglyceric_acid" title="3-Phosphoglyceric acid">3-Phosphoglycerate</a></p> </div><div style="margin: auto 0"><strong>2&#160;×&#160;</strong> <span typeof="mw:File"><a href="/wiki/File:3-phospho-D-glycerate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/99/3-phospho-D-glycerate.svg/70px-3-phospho-D-glycerate.svg.png" decoding="async" width="70" height="100" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/99/3-phospho-D-glycerate.svg/105px-3-phospho-D-glycerate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/99/3-phospho-D-glycerate.svg/140px-3-phospho-D-glycerate.svg.png 2x" data-file-width="193" data-file-height="277" /></a></span></div> </div> <div style="text-align: center; display: inline-block; display: inline-flex; flex-flow: column; flex: 1; vertical-align:top;"><div style="width: 100%; display: block; background-color:#ffcccc;"> <p style="margin: 0.1em 0.5em;"><a href="/wiki/Phosphoglycerate_mutase" title="Phosphoglycerate mutase">Phosphoglycerate mutase</a></p> </div><div style="line-height: 1; flex: 1 0 auto; display: flex; flex-flow: row wrap; justify-content: space-around; align-items: flex-end; min-height: 22.5px;"> </div><div style="width: 100%; clear:both; overflow: hidden; height: 9px;"><div style="position: relative; bottom: 18px;"><span typeof="mw:File"><a href="/wiki/File:Biochem_reaction_arrow_reversible_NNNN_horiz_med.svg" class="mw-file-description" title="Reversible left-right reaction arrow"><img alt="Reversible left-right reaction arrow" src="//upload.wikimedia.org/wikipedia/commons/thumb/7/70/Biochem_reaction_arrow_reversible_NNNN_horiz_med.svg/45px-Biochem_reaction_arrow_reversible_NNNN_horiz_med.svg.png" decoding="async" width="45" height="45" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/70/Biochem_reaction_arrow_reversible_NNNN_horiz_med.svg/68px-Biochem_reaction_arrow_reversible_NNNN_horiz_med.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/70/Biochem_reaction_arrow_reversible_NNNN_horiz_med.svg/90px-Biochem_reaction_arrow_reversible_NNNN_horiz_med.svg.png 2x" data-file-width="75" data-file-height="75" /></a></span></div></div><div style="line-height: 1; flex: 1 0 auto; display: flex; flex-flow: row wrap; justify-content: space-around; min-height: 22.5px;"></div> </div> <div style="text-align: center; display: inline-block; display: inline-flex; flex-flow: column; flex: 1; vertical-align:top;"><div style="width: 100%; display: block; background-color:lightgreen;"> <p style="margin: 0.1em 0.5em;"><strong>2 × </strong><a href="/wiki/2-Phosphoglyceric_acid" title="2-Phosphoglyceric acid">2-Phosphoglycerate</a></p> </div><div style="margin: auto 0"><strong>2&#160;×&#160;</strong> <span typeof="mw:File"><a href="/wiki/File:2-phospho-D-glycerate_wpmp.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/2a/2-phospho-D-glycerate_wpmp.svg/70px-2-phospho-D-glycerate_wpmp.svg.png" decoding="async" width="70" height="58" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/2a/2-phospho-D-glycerate_wpmp.svg/105px-2-phospho-D-glycerate_wpmp.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/2a/2-phospho-D-glycerate_wpmp.svg/140px-2-phospho-D-glycerate_wpmp.svg.png 2x" data-file-width="115" data-file-height="95" /></a></span></div> </div> <div style="text-align: center; display: inline-block; display: inline-flex; flex-flow: column; flex: 1; vertical-align:top;"><div style="width: 100%; display: block; background-color:#ffcccc;"> <p style="margin: 0.1em 0.5em;"><a href="/wiki/Phosphopyruvate_hydratase" class="mw-redirect" title="Phosphopyruvate hydratase">Phosphopyruvate<br />hydratase</a> (<a href="/wiki/Enolase" title="Enolase">enolase</a>)</p> </div><div style="line-height: 1; flex: 1 0 auto; display: flex; flex-flow: row wrap; justify-content: space-around; align-items: flex-end;"><div style="width: 45%; float:left">&#160;</div> <div style="width: 45%; float:right">H<sub>2</sub>O</div> </div><div style="width: 100%; clear:both; overflow: hidden; height: 45px;"><div style=""><span typeof="mw:File"><a href="/wiki/File:Biochem_reaction_arrow_reversible_NYYN_horiz_med.svg" class="mw-file-description" title="Reversible left-right reaction arrow with minor forward product(s) to top right and minor reverse substrate(s) from bottom right"><img alt="Reversible left-right reaction arrow with minor forward product(s) to top right and minor reverse substrate(s) from bottom right" src="//upload.wikimedia.org/wikipedia/commons/thumb/8/86/Biochem_reaction_arrow_reversible_NYYN_horiz_med.svg/45px-Biochem_reaction_arrow_reversible_NYYN_horiz_med.svg.png" decoding="async" width="45" height="45" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/86/Biochem_reaction_arrow_reversible_NYYN_horiz_med.svg/68px-Biochem_reaction_arrow_reversible_NYYN_horiz_med.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/86/Biochem_reaction_arrow_reversible_NYYN_horiz_med.svg/90px-Biochem_reaction_arrow_reversible_NYYN_horiz_med.svg.png 2x" data-file-width="75" data-file-height="75" /></a></span></div></div><div style="line-height: 1; flex: 1 0 auto; display: flex; flex-flow: row wrap; justify-content: space-around;"><div style="width: 45%; float:left">&#160;</div> <div style="width: 45%; float:right">H<sub>2</sub>O</div><div style="clear:both;" class=""></div></div> </div> <div style="text-align: center; display: inline-block; display: inline-flex; flex-flow: column; flex: 1; vertical-align:top;"><div style="width: 100%; display: block; background-color:lightgreen;"> <p style="margin: 0.1em 0.5em;"><strong>2 × </strong><a href="/wiki/Phosphoenolpyruvate" class="mw-redirect" title="Phosphoenolpyruvate">Phosphoenolpyruvate</a></p> </div><div style="margin: auto 0"><strong>2&#160;×&#160;</strong> <span typeof="mw:File"><a href="/wiki/File:Phosphoenolpyruvate_wpmp.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/bc/Phosphoenolpyruvate_wpmp.svg/70px-Phosphoenolpyruvate_wpmp.svg.png" decoding="async" width="70" height="99" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/bc/Phosphoenolpyruvate_wpmp.svg/105px-Phosphoenolpyruvate_wpmp.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/bc/Phosphoenolpyruvate_wpmp.svg/140px-Phosphoenolpyruvate_wpmp.svg.png 2x" data-file-width="77" data-file-height="109" /></a></span></div> </div> <div style="text-align: center; display: inline-block; display: inline-flex; flex-flow: column; flex: 1; vertical-align:top;"><div style="width: 100%; display: block; background-color:#ffcccc;"> <p style="margin: 0.1em 0.5em;"><a href="/wiki/Pyruvate_kinase" title="Pyruvate kinase">Pyruvate kinase</a></p> </div><div style="line-height: 1; flex: 1 0 auto; display: flex; flex-flow: row wrap; justify-content: space-around; align-items: flex-end;"><div style="width: 45%; float:left">ADP</div> <div style="width: 45%; float:right">ATP</div> </div><div style="width: 100%; clear:both; overflow: hidden; height: 27px;"><div style=""><span typeof="mw:File"><a href="/wiki/File:Biochem_reaction_arrow_forward_YYNN_horiz_med.svg" class="mw-file-description" title="Rightward reaction arrow with minor substrate(s) from top left and minor product(s) to top right"><img alt="Rightward reaction arrow with minor substrate(s) from top left and minor product(s) to top right" src="//upload.wikimedia.org/wikipedia/commons/thumb/8/85/Biochem_reaction_arrow_forward_YYNN_horiz_med.svg/45px-Biochem_reaction_arrow_forward_YYNN_horiz_med.svg.png" decoding="async" width="45" height="45" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/85/Biochem_reaction_arrow_forward_YYNN_horiz_med.svg/68px-Biochem_reaction_arrow_forward_YYNN_horiz_med.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/85/Biochem_reaction_arrow_forward_YYNN_horiz_med.svg/90px-Biochem_reaction_arrow_forward_YYNN_horiz_med.svg.png 2x" data-file-width="75" data-file-height="75" /></a></span></div></div><div style="line-height: 1; flex: 1 0 auto; display: flex; flex-flow: row wrap; justify-content: space-around; min-height: 22.5px;"></div> </div> <div style="text-align: center; display: inline-block; display: inline-flex; flex-flow: column; flex: 1; vertical-align:top;"><div style="width: 100%; display: block; background-color:lightgreen;"> <p style="margin: 0.1em 0.5em;"><strong>2 × </strong><a href="/wiki/Pyruvic_acid" title="Pyruvic acid">Pyruvate</a></p> </div><div style="margin: auto 0"><strong>2&#160;×&#160;</strong> <span typeof="mw:File"><a href="/wiki/File:Pyruvat.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/79/Pyruvat.svg/70px-Pyruvat.svg.png" decoding="async" width="70" height="37" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/79/Pyruvat.svg/105px-Pyruvat.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/79/Pyruvat.svg/140px-Pyruvat.svg.png 2x" data-file-width="154" data-file-height="82" /></a></span></div> </div> </div> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Inborn_error_of_carbohydrate_metabolism:_monosaccharide_metabolism_disorders_Including_glycogen_storage_diseases_(GSD)" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Inborn_errors_of_carbohydrate_metabolism" title="Template:Inborn errors of carbohydrate metabolism"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Inborn_errors_of_carbohydrate_metabolism" title="Template talk:Inborn errors of carbohydrate metabolism"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Inborn_errors_of_carbohydrate_metabolism" title="Special:EditPage/Template:Inborn errors of carbohydrate metabolism"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Inborn_error_of_carbohydrate_metabolism:_monosaccharide_metabolism_disorders_Including_glycogen_storage_diseases_(GSD)" style="font-size:114%;margin:0 4em"><a href="/wiki/Inborn_error_of_metabolism" class="mw-redirect" title="Inborn error of metabolism">Inborn error</a> of <a href="/wiki/Inborn_errors_of_carbohydrate_metabolism" title="Inborn errors of carbohydrate metabolism">carbohydrate metabolism</a>: <a href="/wiki/Monosaccharide" title="Monosaccharide">monosaccharide</a> metabolism disorders <br /> Including <a href="/wiki/Glycogen_storage_disease" title="Glycogen storage disease">glycogen storage diseases</a> (GSD)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Sucrose" title="Sucrose">Sucrose</a>, transport<br />(extracellular)</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Disaccharide" title="Disaccharide">Disaccharide</a> catabolism</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Lactose_intolerance" title="Lactose intolerance">Congenital alactasia</a></li> <li><a href="/wiki/Sucrose_intolerance" title="Sucrose intolerance">Sucrose intolerance</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Monosaccharide" title="Monosaccharide">Monosaccharide</a> transport</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Glucose-galactose_malabsorption" title="Glucose-galactose malabsorption">Glucose-galactose malabsorption</a></li> <li><a href="/wiki/Inborn_errors_of_renal_tubular_transport" title="Inborn errors of renal tubular transport">Inborn errors of renal tubular transport</a> (<a href="/wiki/Renal_glycosuria" title="Renal glycosuria">Renal glycosuria</a>)</li> <li><a href="/wiki/Fructose_malabsorption" title="Fructose malabsorption">Fructose malabsorption</a></li> <li><a href="/wiki/GLUT1_deficiency" title="GLUT1 deficiency">De Vivo Disease</a> (GLUT1 deficiency)</li> <li><a href="/wiki/Fanconi-Bickel_syndrome" class="mw-redirect" title="Fanconi-Bickel syndrome">Fanconi-Bickel syndrome</a> (GLUT2 deficiency)</li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Hexose" title="Hexose">Hexose</a> → <a class="mw-selflink selflink">glucose</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Monosaccharide_catabolism" scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Monosaccharide" title="Monosaccharide">Monosaccharide</a> catabolism</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><span class="nobold"><a href="/wiki/Fructose" title="Fructose">Fructose</a>:</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Essential_fructosuria" title="Essential fructosuria">Essential fructosuria</a></li> <li><a href="/wiki/Hereditary_fructose_intolerance" title="Hereditary fructose intolerance">Fructose intolerance</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><span class="nobold"><a href="/wiki/Galactose" title="Galactose">Galactose</a> / <a href="/wiki/Galactosemia" title="Galactosemia">galactosemia</a>:</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Galactokinase_deficiency" title="Galactokinase deficiency">GALK deficiency</a></li> <li><a href="/wiki/Galactose-1-phosphate_uridylyltransferase_deficiency" title="Galactose-1-phosphate uridylyltransferase deficiency">GALT deficiency</a>/<a href="/wiki/Galactose_epimerase_deficiency" title="Galactose epimerase deficiency">GALE deficiency</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a class="mw-selflink selflink">Glucose</a> ⇄ <a href="/wiki/Glycogen" title="Glycogen">glycogen</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Glycogenesis" title="Glycogenesis">Glycogenesis</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Glycogen_storage_disease_type_0" title="Glycogen storage disease type 0">GSD type 0</a> (glycogen synthase deficiency)</li> <li><a href="/wiki/Glycogen_storage_disease_type_IV" title="Glycogen storage disease type IV">GSD type IV</a> (Andersen's disease, branching enzyme deficiency)</li> <li><a href="/wiki/Adult_polyglucosan_body_disease" title="Adult polyglucosan body disease">Adult polyglucosan body disease</a> (APBD)</li> <li><a href="/wiki/Lafora_disease" title="Lafora disease">Lafora disease</a></li> <li><a href="/w/index.php?title=GSD_type_XV&amp;action=edit&amp;redlink=1" class="new" title="GSD type XV (page does not exist)">GSD type XV</a> (glycogenin deficiency)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Glycogenolysis" title="Glycogenolysis">Glycogenolysis</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><span class="nobold">Extralysosomal:</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Glycogen_storage_disease_type_III" title="Glycogen storage disease type III">GSD type III</a> (Cori's disease, debranching enzyme deficiency)</li> <li><a href="/wiki/Glycogen_storage_disease_type_VI" title="Glycogen storage disease type VI">GSD type VI</a> (Hers' disease, liver glycogen phosphorylase deficiency)</li> <li><a href="/wiki/Glycogen_storage_disease_type_V" title="Glycogen storage disease type V">GSD type V</a> (McArdle's disease, myophosphorylase deficiency)</li> <li><a href="/wiki/Glycogen_storage_disease_type_IX" title="Glycogen storage disease type IX">GSD type IX</a> (phosphorylase kinase deficiency)</li> <li><a href="/wiki/Phosphoglucomutase#Disease_relevance" title="Phosphoglucomutase">Phosphoglucomutase deficiency</a> (PGM1-CDG, CDG1T, formerly GSD-XIV)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><span class="nobold"><a href="/wiki/Lysosome" title="Lysosome">Lysosomal</a> (<a href="/wiki/Lysosomal_storage_disease" title="Lysosomal storage disease">LSD</a>):</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Glycogen_storage_disease_type_II" title="Glycogen storage disease type II">Glycogen storage disease type II</a> (Pompe's disease, glucosidase deficiency, formerly GSD-IIa)</li> <li><a href="/wiki/Danon_disease" title="Danon disease">Danon disease</a> (LAMP2 deficiency, formerly GSD-IIb)</li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a class="mw-selflink selflink">Glucose</a> ⇄ <a href="/wiki/Citric_acid_cycle" title="Citric acid cycle">CAC</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Glycolysis" title="Glycolysis">Glycolysis</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/MODY_2" title="MODY 2">MODY 2</a>/<a href="/wiki/Hyperinsulinemic_hypoglycemia" title="Hyperinsulinemic hypoglycemia">HHF3</a></li> <li><a href="/wiki/Phosphofructokinase_deficiency" title="Phosphofructokinase deficiency">GSD type VII</a> (Tarui's disease, phosphofructokinase deficiency)</li> <li><a href="/wiki/Triosephosphate_isomerase_deficiency" title="Triosephosphate isomerase deficiency">Triosephosphate isomerase deficiency</a></li> <li><a href="/wiki/Pyruvate_kinase_deficiency" title="Pyruvate kinase deficiency">Pyruvate kinase deficiency</a></li> <li><a href="/wiki/Aldolase_A_deficiency" title="Aldolase A deficiency">Aldolase A deficiency</a></li> <li>Phosphoglucose isomerase deficiency</li> <li>Phosphoglycerate kinase deficiency</li> <li><a href="/wiki/MPC1" class="mw-redirect" title="MPC1">Mitochondrial pyruvate carrier deficiency</a> (MPC1 deficiency)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Gluconeogenesis" title="Gluconeogenesis">Gluconeogenesis</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Pyruvate_carboxylase_deficiency" title="Pyruvate carboxylase deficiency">Pyruvate carboxylase deficiency</a></li> <li><a href="/wiki/Fructose_bisphosphatase_deficiency" title="Fructose bisphosphatase deficiency">Fructose bisphosphatase deficiency</a></li> <li><a href="/wiki/Glycogen_storage_disease_type_I" title="Glycogen storage disease type I">GSD type I</a> (von Gierke's disease, glucose 6-phosphatase deficiency)</li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Pentose_phosphate_pathway" title="Pentose phosphate pathway">Pentose phosphate pathway</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Glucose-6-phosphate_dehydrogenase_deficiency" title="Glucose-6-phosphate dehydrogenase deficiency">Glucose-6-phosphate dehydrogenase deficiency</a></li> <li><a href="/wiki/Transaldolase_deficiency" title="Transaldolase deficiency">Transaldolase deficiency</a></li> <li><a href="/wiki/Transketolase#Role_in_disease" title="Transketolase">SDDHD</a> (Transketolase deficiency)</li> <li><a href="/wiki/6-phosphogluconate_dehydrogenase_deficiency" title="6-phosphogluconate dehydrogenase deficiency">6-phosphogluconate dehydrogenase deficiency</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Hyperoxaluria" title="Hyperoxaluria">Hyperoxaluria</a> <ul><li><a href="/wiki/Primary_hyperoxaluria" title="Primary hyperoxaluria">Primary hyperoxaluria</a></li></ul></li> <li><a href="/wiki/Pentosuria" title="Pentosuria">Pentosuria</a></li> <li>Fatal congenital nonlysosomal cardiac glycogenosis (<a href="/wiki/AMP-activated_protein_kinase" title="AMP-activated protein kinase">AMP-activated protein kinase</a> deficiency, <a href="/wiki/PRKAG2" title="PRKAG2">PRKAG2</a>)</li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Types_of_carbohydrates" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Carbohydrates" title="Template:Carbohydrates"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Carbohydrates" title="Template talk:Carbohydrates"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Carbohydrates" title="Special:EditPage/Template:Carbohydrates"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Types_of_carbohydrates" style="font-size:114%;margin:0 4em">Types of <a href="/wiki/Carbohydrate" title="Carbohydrate">carbohydrates</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">General</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Aldose" title="Aldose">Aldose</a></li> <li><a href="/wiki/Ketose" title="Ketose">Ketose</a></li> <li><a href="/wiki/Furanose" title="Furanose">Furanose</a></li> <li><a href="/wiki/Pyranose" title="Pyranose">Pyranose</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Geometry</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Anomer" title="Anomer">Anomer</a></li> <li><a href="/wiki/Cyclohexane_conformation" title="Cyclohexane conformation">Cyclohexane conformation</a></li> <li><a href="/wiki/Epimer" title="Epimer">Epimer</a></li> <li><a href="/wiki/Mutarotation" title="Mutarotation">Mutarotation</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Monosaccharide" title="Monosaccharide">Monosaccharides</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Diose" title="Diose">Dioses</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Aldodiose <ul><li><a href="/wiki/Glycolaldehyde" title="Glycolaldehyde">Glycolaldehyde</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Triose" title="Triose">Trioses</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Aldotriose <ul><li><a href="/wiki/Glyceraldehyde" title="Glyceraldehyde">Glyceraldehyde</a></li></ul></li> <li>Ketotriose <ul><li><a href="/wiki/Dihydroxyacetone" title="Dihydroxyacetone">Dihydroxyacetone</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Tetrose" title="Tetrose">Tetroses</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Aldotetroses <ul><li><a href="/wiki/Erythrose" title="Erythrose">Erythrose</a></li> <li><a href="/wiki/Threose" title="Threose">Threose</a></li></ul></li> <li>Ketotetrose <ul><li><a href="/wiki/Erythrulose" title="Erythrulose">Erythrulose</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Pentose" title="Pentose">Pentoses</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Aldopentoses <ul><li><a href="/wiki/Arabinose" title="Arabinose">Arabinose</a></li> <li><a href="/wiki/Lyxose" title="Lyxose">Lyxose</a></li> <li><a href="/wiki/Ribose" title="Ribose">Ribose</a></li> <li><a href="/wiki/Xylose" title="Xylose">Xylose</a></li></ul></li> <li>Ketopentoses <ul><li><a href="/wiki/Ribulose" title="Ribulose">Ribulose</a></li> <li><a href="/wiki/Xylulose" title="Xylulose">Xylulose</a></li></ul></li> <li><a href="/wiki/Deoxy_sugar" title="Deoxy sugar">Deoxy sugars</a> <ul><li><a href="/wiki/Deoxyribose" title="Deoxyribose">Deoxyribose</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Hexose" title="Hexose">Hexoses</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Aldohexose" class="mw-redirect" title="Aldohexose">Aldohexoses</a> <ul><li><a href="/wiki/Allose" title="Allose">Allose</a></li> <li><a href="/wiki/Altrose" title="Altrose">Altrose</a></li> <li><a href="/wiki/Galactose" title="Galactose">Galactose</a></li> <li><a class="mw-selflink selflink">Glucose</a></li> <li><a href="/wiki/Gulose" title="Gulose">Gulose</a></li> <li><a href="/wiki/Idose" title="Idose">Idose</a></li> <li><a href="/wiki/Mannose" title="Mannose">Mannose</a></li> <li><a href="/wiki/Talose" title="Talose">Talose</a></li></ul></li> <li><a href="/wiki/Ketohexose" class="mw-redirect" title="Ketohexose">Ketohexoses</a> <ul><li><a href="/wiki/Fructose" title="Fructose">Fructose</a></li> <li><a href="/wiki/Psicose" title="Psicose">Psicose</a></li> <li><a href="/wiki/Sorbose" title="Sorbose">Sorbose</a></li> <li><a href="/wiki/Tagatose" title="Tagatose">Tagatose</a></li></ul></li> <li>Deoxy sugars <ul><li><a href="/wiki/Fucose" title="Fucose">Fucose</a></li> <li><a href="/wiki/Fuculose" title="Fuculose">Fuculose</a></li> <li><a href="/wiki/Rhamnose" title="Rhamnose">Rhamnose</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Heptose" title="Heptose">Heptoses</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Ketoheptoses <ul><li><a href="/wiki/Mannoheptulose" title="Mannoheptulose">Mannoheptulose</a></li> <li><a href="/wiki/Sedoheptulose" title="Sedoheptulose">Sedoheptulose</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Above 7</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Octose" title="Octose">Octoses</a></li> <li><a href="/wiki/Nonose" title="Nonose">Nonoses</a> <ul><li><a href="/wiki/Neuraminic_acid" title="Neuraminic acid">Neuraminic acid</a></li></ul></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Multiple</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Disaccharide" title="Disaccharide">Disaccharides</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cellobiose" title="Cellobiose">Cellobiose</a></li> <li><a href="/wiki/Isomaltose" title="Isomaltose">Isomaltose</a></li> <li><a href="/wiki/Isomaltulose" title="Isomaltulose">Isomaltulose</a></li> <li><a href="/wiki/Lactose" title="Lactose">Lactose</a></li> <li><a href="/wiki/Lactulose" title="Lactulose">Lactulose</a></li> <li><a href="/wiki/Maltose" title="Maltose">Maltose</a></li> <li><a href="/wiki/Sucrose" title="Sucrose">Sucrose</a></li> <li><a href="/wiki/Trehalose" title="Trehalose">Trehalose</a></li> <li><a href="/wiki/Turanose" title="Turanose">Turanose</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Trisaccharide" title="Trisaccharide">Trisaccharides</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Maltotriose" title="Maltotriose">Maltotriose</a></li> <li><a href="/wiki/Melezitose" title="Melezitose">Melezitose</a></li> <li><a href="/wiki/Raffinose" title="Raffinose">Raffinose</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Tetrasaccharide" title="Tetrasaccharide">Tetrasaccharides</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Stachyose" title="Stachyose">Stachyose</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other<br /> <a href="/wiki/Oligosaccharide" title="Oligosaccharide">oligosaccharides</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acarbose" title="Acarbose">Acarbose</a></li> <li><a href="/wiki/Fructooligosaccharide" title="Fructooligosaccharide">Fructooligosaccharide</a> (FOS)</li> <li><a href="/wiki/Galactooligosaccharide" title="Galactooligosaccharide">Galactooligosaccharide</a> (GOS)</li> <li><a href="/wiki/Isomaltooligosaccharide" title="Isomaltooligosaccharide">Isomaltooligosaccharide</a> (IMO)</li> <li><a href="/wiki/Maltodextrin" title="Maltodextrin">Maltodextrin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Polysaccharide" title="Polysaccharide">Polysaccharides</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Beta-glucan" title="Beta-glucan">Beta-glucan</a> <ul><li><a href="/wiki/Oat_beta-glucan" title="Oat beta-glucan">Oat beta-glucan</a></li> <li><a href="/wiki/Lentinan" title="Lentinan">Lentinan</a></li> <li><a href="/wiki/Schizophyllan" title="Schizophyllan">Sizofiran</a></li> <li><a href="/wiki/Zymosan" title="Zymosan">Zymosan</a></li> <li><a href="/wiki/Cellulose" title="Cellulose">Cellulose</a></li> <li><a href="/wiki/Chitin" title="Chitin">Chitin</a></li></ul></li> <li><a href="/wiki/Chitosan" title="Chitosan">Chitosan</a></li> <li><a href="/wiki/Dextrin" title="Dextrin">Dextrin</a> / <a href="/wiki/Dextran" title="Dextran">Dextran</a></li> <li><i><a href="/wiki/Fructose" title="Fructose">Fructose</a> / <a href="/wiki/Fructan" title="Fructan">Fructan</a></i> <ul><li><a href="/wiki/Inulin" title="Inulin">Inulin</a></li></ul></li> <li><i><a href="/wiki/Galactose" title="Galactose">Galactose</a> / <a href="/wiki/Galactose" title="Galactose">Galactan</a></i></li> <li><i><a class="mw-selflink selflink">Glucose</a> / <a href="/wiki/Glucan" title="Glucan">Glucan</a></i> <ul><li><a href="/wiki/Glycogen" title="Glycogen">Glycogen</a></li></ul></li> <li><a href="/wiki/Hemicellulose" title="Hemicellulose">Hemicellulose</a></li> <li><a href="/wiki/Levan_polysaccharide" title="Levan polysaccharide">Levan beta 2→6</a></li> <li><a href="/wiki/Lignin" title="Lignin">Lignin</a></li> <li><a href="/wiki/Mannans" title="Mannans">Mannan</a></li> <li><a href="/wiki/Pectin" title="Pectin">Pectin</a></li> <li><a href="/wiki/Starch" title="Starch">Starch</a> <ul><li><a href="/wiki/Amylopectin" title="Amylopectin">Amylopectin</a></li> <li><a href="/wiki/Amylose" title="Amylose">Amylose</a></li></ul></li> <li><a href="/wiki/Xanthan_gum" title="Xanthan gum">Xanthan gum</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <ul><li><span class="noviewer" typeof="mw:File"><span title="Category"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/16px-Symbol_category_class.svg.png" decoding="async" width="16" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/23px-Symbol_category_class.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/31px-Symbol_category_class.svg.png 2x" data-file-width="180" data-file-height="185" /></span></span> <a href="/wiki/Category:Carbohydrates" title="Category:Carbohydrates">Category</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Sugar_as_food_commodity" style="padding:3px"><table class="nowraplinks hlist mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Sugar" title="Template:Sugar"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Sugar" title="Template talk:Sugar"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Sugar" title="Special:EditPage/Template:Sugar"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Sugar_as_food_commodity" style="font-size:114%;margin:0 4em"><a href="/wiki/Sugar" title="Sugar">Sugar</a> as food commodity</div></th></tr><tr><td class="navbox-abovebelow" colspan="2"><div><a href="/wiki/List_of_sugars" title="List of sugars">List of sugars and sugar products</a></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Chemistry</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Monosaccharide" title="Monosaccharide">Monosaccharide</a> <ul><li><a href="/wiki/Fructose" title="Fructose">Fructose</a></li> <li><a href="/wiki/Galactose" title="Galactose">Galactose</a></li> <li><a class="mw-selflink selflink">Glucose</a></li> <li><a href="/wiki/Xylose" title="Xylose">Xylose</a></li></ul></li> <li><a href="/wiki/Disaccharide" title="Disaccharide">Disaccharide</a> <ul><li><a href="/wiki/Lactose" title="Lactose">Lactose</a></li> <li><a href="/wiki/Maltose" title="Maltose">Maltose</a></li> <li><a href="/wiki/Sucrose" title="Sucrose">Sucrose</a></li> <li><a href="/wiki/Trehalose" title="Trehalose">Trehalose</a></li></ul></li> <li><a href="/wiki/Added_sugar" title="Added sugar">Added sugar</a></li> <li><a href="/wiki/Reducing_sugar" title="Reducing sugar">Reducing sugar</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Sources</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Sugar_beet" title="Sugar beet">Sugar beet</a></li> <li><a href="/wiki/Sugarcane" title="Sugarcane">Sugarcane</a></li> <li><a href="/wiki/Agave_syrup" title="Agave syrup">Agave syrup</a></li> <li><a href="/wiki/Birch_syrup" title="Birch syrup">Birch</a></li> <li><a href="/wiki/Coconut_sugar" title="Coconut sugar">Coconut</a></li> <li><a href="/wiki/Date_sugar" title="Date sugar">Date</a></li> <li><a href="/wiki/Honeydew_(secretion)" title="Honeydew (secretion)">Honeydew</a></li> <li><a href="/wiki/Maple_sugar" title="Maple sugar">Maple</a></li> <li><a href="/wiki/Palm_sugar" title="Palm sugar">Palm</a></li> <li><a href="/wiki/Malt_sugar" class="mw-redirect" title="Malt sugar">Malt</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Products</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Syrup" title="Syrup">Syrups</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/List_of_syrups" title="List of syrups">List of syrups</a></li> <li><a href="/wiki/Agave_syrup" title="Agave syrup">Agave syrup</a></li> <li><a href="/wiki/Barley_malt_syrup" title="Barley malt syrup">Barley malt syrup</a></li> <li><a href="/wiki/Brown_rice_syrup" title="Brown rice syrup">Brown rice syrup</a></li> <li><a href="/wiki/Cheong_(food)" title="Cheong (food)">Cheong</a> <ul><li><a href="/wiki/Maesil-cheong" class="mw-redirect" title="Maesil-cheong">Maesil-cheong</a></li> <li><a href="/wiki/Mogwa-cheong" class="mw-redirect" title="Mogwa-cheong">Mogwa-cheong</a></li> <li><a href="/wiki/Yuja-cheong" class="mw-redirect" title="Yuja-cheong">Yuja-cheong</a></li></ul></li> <li><a href="/wiki/Corn_syrup" title="Corn syrup">Corn syrup</a></li> <li><a href="/wiki/Glucose_syrup" title="Glucose syrup">Glucose syrup</a></li> <li><a href="/wiki/Golden_syrup" title="Golden syrup">Golden syrup</a></li> <li><a href="/wiki/High-fructose_corn_syrup" title="High-fructose corn syrup">High-fructose corn syrup</a></li> <li><a href="/wiki/High-maltose_corn_syrup" title="High-maltose corn syrup">High-maltose corn syrup</a></li> <li><a href="/wiki/Honey" title="Honey">Honey</a></li> <li><a href="/wiki/Inverted_sugar_syrup" title="Inverted sugar syrup">Inverted sugar syrup</a></li> <li><a href="/wiki/Kuromitsu" title="Kuromitsu">Kuromitsu</a></li> <li><a href="/wiki/Maple_syrup" title="Maple syrup">Maple syrup</a></li> <li><a href="/wiki/Mizuame" title="Mizuame">Mizuame</a></li> <li><a href="/wiki/Molasses" title="Molasses">Molasses</a></li> <li><a href="/wiki/Pine_honey" title="Pine honey">Pine honey</a></li> <li><a href="/wiki/Steen%27s_cane_syrup" title="Steen&#39;s cane syrup">Steen's cane syrup</a></li> <li><a href="/wiki/Table_syrup" title="Table syrup">Table syrup</a></li> <li><a href="/wiki/Treacle" title="Treacle">Treacle</a></li> <li><a href="/wiki/Yac%C3%B3n_syrup" title="Yacón syrup">Yacón syrup</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Solid forms</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Brown_sugar" title="Brown sugar">Brown</a> <ul><li><i><a href="/wiki/Peen_tong" title="Peen tong">Peen tong</a></i></li></ul></li> <li><a href="/wiki/Candi_sugar" title="Candi sugar">Candi sugar</a></li> <li><a href="/wiki/Chancaca" title="Chancaca">Chancaca</a></li> <li><a href="/wiki/Crystalline_fructose" class="mw-redirect" title="Crystalline fructose">Crystalline fructose</a></li> <li><a href="/wiki/Gelling_sugar" title="Gelling sugar">Gelling</a></li> <li><a href="/wiki/Gula_melaka" class="mw-redirect" title="Gula melaka">Gula melaka</a></li> <li><a href="/wiki/Jaggery" title="Jaggery">Jaggery</a></li> <li><a href="/wiki/Misri" class="mw-redirect" title="Misri">Misri</a></li> <li><a href="/wiki/Molasses_sugar" title="Molasses sugar">Molasses sugar</a></li> <li><a href="/wiki/Muscovado" title="Muscovado">Muscovado</a></li> <li><a href="/wiki/Nib_sugar" title="Nib sugar">Nib</a></li> <li><a href="/wiki/Non-centrifugal_cane_sugar" title="Non-centrifugal cane sugar">Non-centrifugal cane sugar</a></li> <li><a href="/wiki/Panela" title="Panela">Panela</a></li> <li><a href="/wiki/Plantation_Reserve" title="Plantation Reserve">Plantation Reserve</a></li> <li><a href="/wiki/Powdered_sugar" title="Powdered sugar">Powdered</a></li> <li><a href="/wiki/Preserving_sugar" title="Preserving sugar">Preserving</a></li> <li><a href="/wiki/Sucanat" title="Sucanat">Sucanat</a></li> <li><a href="/wiki/Sugar_candy" title="Sugar candy">Sugar candy</a> <ul><li><a href="/wiki/Barley_sugar" title="Barley sugar">Barley sugar</a></li> <li><a href="/wiki/Butterscotch" title="Butterscotch">Butterscotch</a></li> <li><a href="/wiki/Candy" title="Candy">Candy</a></li> <li><a href="/wiki/Hard_candy" title="Hard candy">Hard</a></li> <li><a href="/wiki/Rock_candy" title="Rock candy">Rock candy</a></li> <li><a href="/wiki/Toffee" title="Toffee">Toffee</a></li></ul></li> <li><a href="/wiki/Sugar_glass" title="Sugar glass">Sugar glass</a></li> <li><a href="/wiki/Sugarloaf" title="Sugarloaf">Sugarloaf</a></li> <li><a href="/wiki/Wasanbon" title="Wasanbon">Wasanbon</a></li> <li><a href="/wiki/White_sugar" title="White sugar">White</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other forms</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Caramel" title="Caramel">Caramel</a></li> <li><a href="/wiki/Cotton_candy" title="Cotton candy">Cotton candy floss</a></li> <li><a href="/wiki/List_of_foods_made_from_maple" title="List of foods made from maple">Maple sugar foods</a></li> <li><a href="/wiki/Rum" title="Rum">Rum</a></li> <li><a href="/wiki/Sugar_alcohol" title="Sugar alcohol">Sugar alcohol</a></li> <li><a href="/wiki/Confectionery#Sugar_confectionery" title="Confectionery">Sugar confectionery</a></li> <li><a href="/wiki/Sugarcane_juice" title="Sugarcane juice">Sugarcane juice</a></li> <li><a href="/wiki/Tuzem%C3%A1k" title="Tuzemák">Tuzemák</a></li> <li><a href="/wiki/List_of_unrefined_sweeteners" title="List of unrefined sweeteners">Unrefined sweeteners</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Sugar_industry" title="Sugar industry">Industry</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">Production</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Boilery" title="Boilery">Boilery</a></li> <li><a href="/wiki/Plantation#Sugar" title="Plantation">Plantation</a> <ul><li><a href="/wiki/Casa-grande" title="Casa-grande">Casa-grande</a></li></ul></li> <li><a href="/wiki/Sugar_refinery" title="Sugar refinery">Refinery</a></li> <li><a href="/wiki/Sugar_bush" title="Sugar bush">Sugar bush</a></li> <li><a href="/wiki/Sugarcane_mill" title="Sugarcane mill">Sugarcane mill</a></li> <li><a href="/wiki/Engenho" title="Engenho">Engenho</a></li> <li><a href="/wiki/Batey_(sugar_workers%27_town)" title="Batey (sugar workers&#39; town)">Batey</a></li> <li><a href="/wiki/Zafra_(agriculture)" title="Zafra (agriculture)">Zafra</a></li> <li><a href="/wiki/Sugar_marketing" title="Sugar marketing">Sugar marketing</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">By region (current)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/List_of_sugar_mills_in_Queensland" title="List of sugar mills in Queensland">Australia</a> <ul><li><a href="/wiki/Bundaberg_Sugar" title="Bundaberg Sugar">Bundaberg Sugar</a></li> <li><a href="/wiki/CSR_Limited" title="CSR Limited">CSR</a></li> <li><a href="/wiki/Wilmar_Sugar" class="mw-redirect" title="Wilmar Sugar">Wilmar Sugar</a></li></ul></li> <li><a href="/wiki/Cuban_sugar_economy" class="mw-redirect" title="Cuban sugar economy">Cuba</a></li> <li><a href="/wiki/Sugar_plantations_in_the_Caribbean" title="Sugar plantations in the Caribbean">Caribbean</a></li> <li><a href="/wiki/List_of_sugar_manufacturers_in_Kenya" title="List of sugar manufacturers in Kenya">Kenya</a></li> <li><a href="/wiki/Sugar_industry_of_India" title="Sugar industry of India">India</a></li> <li><a href="/wiki/Sugar_industry_of_Mauritius" title="Sugar industry of Mauritius">Mauritius</a></li> <li><a href="/wiki/Sugar_industry_of_the_Philippines" title="Sugar industry of the Philippines">Philippines</a></li> <li><a href="/wiki/Sugar_industry_of_Rwanda" title="Sugar industry of Rwanda">Rwanda</a></li> <li><a href="/wiki/Sugar_industry_of_Sri_Lanka" title="Sugar industry of Sri Lanka">Sri Lanka</a></li> <li><a href="/wiki/Agriculture_in_South_Africa#Sugarcane" title="Agriculture in South Africa">South Africa</a> <ul><li><a href="/wiki/Illovo_Sugar" title="Illovo Sugar">Illovo Sugar</a></li> <li><a href="/wiki/Tongaat_Hulett" title="Tongaat Hulett">Tongaat Hulett</a></li></ul></li> <li><a href="/wiki/List_of_sugar_manufacturers_in_Tanzania" title="List of sugar manufacturers in Tanzania">Tanzania</a></li> <li><a href="/wiki/Sugar_industry_of_Uganda" title="Sugar industry of Uganda">Uganda</a></li> <li>United Kingdom <ul><li><a href="/wiki/British_Sugar" title="British Sugar">British Sugar</a></li> <li><a href="/wiki/Tate_%26_Lyle" title="Tate &amp; Lyle">Tate &amp; Lyle</a></li></ul></li> <li><a href="/wiki/Sugar_industry_of_the_United_States" title="Sugar industry of the United States">United States</a> <ul><li><a href="/wiki/Sugar_Association" title="Sugar Association">Sugar Association</a></li> <li><a href="/wiki/U.S._Sugar_Program" title="U.S. Sugar Program">U.S. Sugar Program</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">By region (historical)</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Sugar_production_in_the_Danish_West_Indies" title="Sugar production in the Danish West Indies">Danish West Indies</a></li> <li><a href="/wiki/Sugar_mills_in_Fiji" title="Sugar mills in Fiji">Fiji</a></li> <li><a href="/wiki/Sugar_plantations_in_Hawaii" title="Sugar plantations in Hawaii">Hawaii</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/History_of_sugar" title="History of sugar">History</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/1811_German_Coast_uprising" title="1811 German Coast uprising">1811 German Coast uprising</a></li> <li><a href="/wiki/Amelioration_Act_1798" title="Amelioration Act 1798">Amelioration Act 1798</a></li> <li><a href="/wiki/Blackbirding" title="Blackbirding">Blackbirding</a></li> <li><a href="/wiki/Colonial_molasses_trade" title="Colonial molasses trade">Colonial molasses trade</a></li> <li><a href="/wiki/Demerara_rebellion_of_1823" title="Demerara rebellion of 1823">Demerara rebellion of 1823</a></li> <li><a href="/wiki/Holing_cane" title="Holing cane">Holing cane</a></li> <li><a href="/wiki/Leith_Sugar_House" title="Leith Sugar House">Leith Sugar House</a></li> <li><a href="/wiki/Molasses_Act" title="Molasses Act">Molasses Act</a></li> <li><a href="/wiki/Reciprocity_Treaty_of_1875" title="Reciprocity Treaty of 1875">Reciprocity Treaty of 1875</a></li> <li><a href="/wiki/Slavery_in_the_British_and_French_Caribbean" title="Slavery in the British and French Caribbean">Slavery in the British and French Caribbean</a></li> <li><a href="/wiki/Sugar_Act" title="Sugar Act">Sugar Act</a></li> <li><a href="/wiki/Sugar_Duties_Acts_1846" title="Sugar Duties Acts 1846">Sugar Duties Acts 1846</a></li> <li><a href="/wiki/Sugar_Intervention" title="Sugar Intervention">Sugar Intervention</a></li> <li><a href="/wiki/Taiwan_Sugar_Railways" title="Taiwan Sugar Railways">Taiwan Sugar Railways</a></li> <li><a href="/wiki/Triangular_trade" title="Triangular trade">Triangular trade</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Culture</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Added_sugar" title="Added sugar">Added sugar</a></li> <li><a href="/wiki/Crop_Over" title="Crop Over">Crop Over</a></li> <li><a href="/wiki/Sugar_shack" title="Sugar shack">Sugar shack</a></li> <li><a href="/wiki/Sugaring" title="Sugaring">Sugaring</a></li> <li><a href="/wiki/Sugar_nips" title="Sugar nips">Sugar nips</a></li> <li><a href="/wiki/Sugar_packet" title="Sugar packet">Sugar packet</a> <ul><li><a href="/wiki/Sucrology" class="mw-redirect" title="Sucrology">Sucrology</a></li></ul></li> <li><a href="/wiki/Sugar_people" title="Sugar people">Sugar people</a></li> <li><a href="/wiki/Sugar_tit" title="Sugar tit">Sugar tit</a></li> <li><a href="/wiki/Sugar_sculpture" title="Sugar sculpture">Sugar sculpture</a></li> <li><a href="/wiki/Treacle_mining" title="Treacle mining">Treacle mining</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Related</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Australian_Aboriginal_sweet_foods" class="mw-redirect" title="Australian Aboriginal sweet foods">Australian Aboriginal sweet foods</a></li> <li><a href="/wiki/Bagasse" title="Bagasse">Bagasse</a></li> <li><a href="/wiki/Blood_sugar_level" title="Blood sugar level">Blood sugar level</a></li> <li><a href="/wiki/Cane_knife" title="Cane knife">Cane knife</a></li> <li><a href="/wiki/Flavored_syrup" title="Flavored syrup">Flavored syrup</a></li> <li><a href="/wiki/Fruit_syrup" title="Fruit syrup">Fruit syrup</a> <ul><li><a href="/wiki/Date_honey" title="Date honey">Date honey</a></li> <li><a href="/wiki/Grape_syrup" title="Grape syrup">Grape</a></li> <li><a href="/wiki/Jallab" title="Jallab">Jallab</a></li></ul></li> <li><a href="/wiki/Health_effects_of_sugar" class="mw-redirect" title="Health effects of sugar">Health effects</a></li> <li><a href="/wiki/Nectar" title="Nectar">Nectar</a></li> <li><a href="/wiki/Sugar_addiction" class="mw-redirect" title="Sugar addiction">Sugar addiction</a></li> <li><a href="/wiki/Sugars_in_wine" title="Sugars in wine">Sugars in wine</a> <ul><li><a href="/wiki/Residual_sugar" class="mw-redirect" title="Residual sugar">Residual sugar</a></li></ul></li> <li><a href="/wiki/Sugar_substitute" title="Sugar substitute">Sugar substitute</a></li> <li><a href="/wiki/Sweetened_beverage" title="Sweetened beverage">Sweetened beverage</a></li> <li><a href="/wiki/Sweetener" title="Sweetener">Sweetener</a></li> <li><a href="/wiki/Sweetness" title="Sweetness">Sweetness</a></li> <li><a href="/wiki/Vinasse" title="Vinasse">Vinasse</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Research</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Robert_Lustig" title="Robert Lustig">Robert Lustig</a></li> <li><a href="/wiki/John_Yudkin" title="John Yudkin">John Yudkin</a> <ul><li><i><a href="/wiki/Pure,_White_and_Deadly" title="Pure, White and Deadly">Pure, White and Deadly</a></i> (1972)</li></ul></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <ul><li><span class="noviewer" typeof="mw:File"><span title="Category"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/16px-Symbol_category_class.svg.png" decoding="async" width="16" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/23px-Symbol_category_class.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/31px-Symbol_category_class.svg.png 2x" data-file-width="180" data-file-height="185" /></span></span> <a href="/wiki/Category:Sugar" title="Category:Sugar">Category</a></li> <li><span class="noviewer" typeof="mw:File"><span 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