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<button aria-controls="toc-Chemical_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 Chemical properties subsection</span> </button> <ul id="toc-Chemical_properties-sublist" class="vector-toc-list"> <li id="toc-Reactions" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Reactions"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.1</span> <span>Reactions</span> </div> </a> <ul id="toc-Reactions-sublist" class="vector-toc-list"> <li id="toc-Fructose_and_fermentation" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Fructose_and_fermentation"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.1.1</span> <span>Fructose and fermentation</span> </div> </a> <ul id="toc-Fructose_and_fermentation-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Fructose_and_Maillard_reaction" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Fructose_and_Maillard_reaction"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.1.2</span> <span>Fructose and Maillard reaction</span> </div> </a> <ul id="toc-Fructose_and_Maillard_reaction-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Dehydration" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Dehydration"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.1.3</span> <span>Dehydration</span> </div> </a> <ul id="toc-Dehydration-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> </ul> </li> <li id="toc-Physical_and_functional_properties" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Physical_and_functional_properties"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Physical and functional properties</span> </div> </a> <button aria-controls="toc-Physical_and_functional_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 Physical and functional properties subsection</span> </button> <ul id="toc-Physical_and_functional_properties-sublist" class="vector-toc-list"> <li id="toc-Sweetness_of_fructose" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Sweetness_of_fructose"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.1</span> <span>Sweetness of fructose</span> </div> </a> <ul id="toc-Sweetness_of_fructose-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Fructose_solubility_and_crystallization" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Fructose_solubility_and_crystallization"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.2</span> <span>Fructose solubility and crystallization</span> </div> </a> <ul id="toc-Fructose_solubility_and_crystallization-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Fructose_hygroscopicity_and_humectancy" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Fructose_hygroscopicity_and_humectancy"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.3</span> <span>Fructose hygroscopicity and humectancy</span> </div> </a> <ul id="toc-Fructose_hygroscopicity_and_humectancy-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Freezing_point" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Freezing_point"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.4</span> <span>Freezing point</span> </div> </a> <ul id="toc-Freezing_point-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Fructose_and_starch_functionality_in_food_systems" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Fructose_and_starch_functionality_in_food_systems"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.5</span> <span>Fructose and starch functionality in food systems</span> </div> </a> <ul id="toc-Fructose_and_starch_functionality_in_food_systems-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Food_sources" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Food_sources"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Food sources</span> </div> </a> <button aria-controls="toc-Food_sources-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 Food sources subsection</span> </button> <ul id="toc-Food_sources-sublist" class="vector-toc-list"> <li id="toc-Carbohydrate_content_of_commercial_sweeteners_(percent_on_dry_basis)" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Carbohydrate_content_of_commercial_sweeteners_(percent_on_dry_basis)"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.1</span> <span>Carbohydrate content of commercial sweeteners (percent on dry basis)</span> </div> </a> <ul id="toc-Carbohydrate_content_of_commercial_sweeteners_(percent_on_dry_basis)-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Nutritional_information" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Nutritional_information"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.2</span> <span>Nutritional information</span> </div> </a> <ul id="toc-Nutritional_information-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Fructose_digestion_and_absorption_in_humans" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Fructose_digestion_and_absorption_in_humans"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Fructose digestion and absorption in humans</span> </div> </a> <button aria-controls="toc-Fructose_digestion_and_absorption_in_humans-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 Fructose digestion and absorption in humans subsection</span> </button> <ul id="toc-Fructose_digestion_and_absorption_in_humans-sublist" class="vector-toc-list"> <li id="toc-Capacity_and_rate_of_absorption" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Capacity_and_rate_of_absorption"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1</span> <span>Capacity and rate of absorption</span> </div> </a> <ul id="toc-Capacity_and_rate_of_absorption-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Malabsorption" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Malabsorption"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.2</span> <span>Malabsorption</span> </div> </a> <ul id="toc-Malabsorption-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Fructose_metabolism" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Fructose_metabolism"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Fructose metabolism</span> </div> </a> <button aria-controls="toc-Fructose_metabolism-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 Fructose metabolism subsection</span> </button> <ul id="toc-Fructose_metabolism-sublist" class="vector-toc-list"> <li id="toc-Fructolysis" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Fructolysis"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.1</span> <span>Fructolysis</span> </div> </a> <ul id="toc-Fructolysis-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Metabolism_of_fructose_to_DHAP_and_glyceraldehyde" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Metabolism_of_fructose_to_DHAP_and_glyceraldehyde"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.2</span> <span>Metabolism of fructose to DHAP and glyceraldehyde</span> </div> </a> <ul id="toc-Metabolism_of_fructose_to_DHAP_and_glyceraldehyde-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Synthesis_of_glycogen_from_DHAP_and_glyceraldehyde_3-phosphate" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Synthesis_of_glycogen_from_DHAP_and_glyceraldehyde_3-phosphate"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.3</span> <span>Synthesis of glycogen from DHAP and glyceraldehyde 3-phosphate</span> </div> </a> <ul id="toc-Synthesis_of_glycogen_from_DHAP_and_glyceraldehyde_3-phosphate-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Synthesis_of_triglyceride_from_DHAP_and_glyceraldehyde_3-phosphate" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Synthesis_of_triglyceride_from_DHAP_and_glyceraldehyde_3-phosphate"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.4</span> <span>Synthesis of triglyceride from DHAP and glyceraldehyde 3-phosphate</span> </div> </a> <ul id="toc-Synthesis_of_triglyceride_from_DHAP_and_glyceraldehyde_3-phosphate-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Potential_health_effects" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Potential_health_effects"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Potential health effects</span> </div> </a> <button aria-controls="toc-Potential_health_effects-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 Potential health effects subsection</span> </button> <ul id="toc-Potential_health_effects-sublist" class="vector-toc-list"> <li id="toc-Cardiometabolic_diseases" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Cardiometabolic_diseases"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.1</span> <span>Cardiometabolic diseases</span> </div> </a> <ul id="toc-Cardiometabolic_diseases-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Compared_with_sucrose" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Compared_with_sucrose"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.2</span> <span>Compared with sucrose</span> </div> </a> <ul id="toc-Compared_with_sucrose-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>See also</span> </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </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> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">10</span> <span>External links</span> </div> </a> <ul id="toc-External_links-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"><span class="mw-page-title-main">Fructose</span></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 79 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-79" 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">79 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/Fruktose" title="Fruktose – Afrikaans" lang="af" hreflang="af" data-title="Fruktose" 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/%D9%81%D8%B1%D9%83%D8%AA%D9%88%D8%B2" title="فركتوز – Arabic" lang="ar" hreflang="ar" data-title="فركتوز" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-ast mw-list-item"><a href="https://ast.wikipedia.org/wiki/Fructosa" title="Fructosa – Asturian" lang="ast" hreflang="ast" data-title="Fructosa" data-language-autonym="Asturianu" data-language-local-name="Asturian" class="interlanguage-link-target"><span>Asturianu</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D9%81%D8%B1%D9%88%DA%A9%D8%AA%D9%88%D8%B2" title="فروکتوز – South Azerbaijani" lang="azb" hreflang="azb" data-title="فروکتوز" 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%AB%E0%A7%8D%E0%A6%B0%E0%A7%81%E0%A6%95%E0%A7%8D%E0%A6%9F%E0%A7%8B%E0%A6%9C" title="ফ্রুক্টোজ – Bangla" lang="bn" hreflang="bn" data-title="ফ্রুক্টোজ" data-language-autonym="বাংলা" data-language-local-name="Bangla" class="interlanguage-link-target"><span>বাংলা</span></a></li><li class="interlanguage-link interwiki-be mw-list-item"><a href="https://be.wikipedia.org/wiki/%D0%A4%D1%80%D1%83%D0%BA%D1%82%D0%BE%D0%B7%D0%B0" title="Фруктоза – Belarusian" lang="be" hreflang="be" data-title="Фруктоза" 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%A4%D1%80%D1%83%D0%BA%D1%82%D0%BE%D0%B7%D0%B0" title="Фруктоза – Belarusian (Taraškievica orthography)" lang="be-tarask" hreflang="be-tarask" data-title="Фруктоза" 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-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%A4%D1%80%D1%83%D0%BA%D1%82%D0%BE%D0%B7%D0%B0" title="Фруктоза – Bulgarian" lang="bg" hreflang="bg" data-title="Фруктоза" 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/Fruktoza" title="Fruktoza – Bosnian" lang="bs" hreflang="bs" data-title="Fruktoza" 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/Fructosa" title="Fructosa – Catalan" lang="ca" hreflang="ca" data-title="Fructosa" 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/Frukt%C3%B3za" title="Fruktóza – Czech" lang="cs" hreflang="cs" data-title="Fruktóza" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Fruktose" title="Fruktose – Danish" lang="da" hreflang="da" data-title="Fruktose" 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/Fructose" title="Fructose – German" lang="de" hreflang="de" data-title="Fructose" 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/Fruktoos" title="Fruktoos – Estonian" lang="et" hreflang="et" data-title="Fruktoos" 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%A6%CF%81%CE%BF%CF%85%CE%BA%CF%84%CF%8C%CE%B6%CE%B7" title="Φρουκτόζη – Greek" lang="el" hreflang="el" data-title="Φρουκτόζη" 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/Fructosa" title="Fructosa – Spanish" lang="es" hreflang="es" data-title="Fructosa" 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/Fruktozo" title="Fruktozo – Esperanto" lang="eo" hreflang="eo" data-title="Fruktozo" 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/Fruktosa" title="Fruktosa – Basque" lang="eu" hreflang="eu" data-title="Fruktosa" 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/%D9%81%D8%B1%D9%88%DA%A9%D8%AA%D9%88%D8%B2" title="فروکتوز – Persian" lang="fa" hreflang="fa" data-title="فروکتوز" 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/Fructose" title="Fructose – French" lang="fr" hreflang="fr" data-title="Fructose" 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/Fruktoaze" title="Fruktoaze – Western Frisian" lang="fy" hreflang="fy" data-title="Fruktoaze" data-language-autonym="Frysk" data-language-local-name="Western Frisian" class="interlanguage-link-target"><span>Frysk</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Frutosa" title="Frutosa – Galician" lang="gl" hreflang="gl" data-title="Frutosa" 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/%ED%94%84%EB%9F%AD%ED%86%A0%EC%8A%A4" title="프럭토스 – Korean" lang="ko" hreflang="ko" data-title="프럭토스" 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/%D5%96%D6%80%D5%B8%D6%82%D5%AF%D5%BF%D5%B8%D5%A6" title="Ֆրուկտոզ – Armenian" lang="hy" hreflang="hy" data-title="Ֆրուկտոզ" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Fruktoza" title="Fruktoza – Croatian" lang="hr" hreflang="hr" data-title="Fruktoza" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Fruktosa" title="Fruktosa – Indonesian" lang="id" hreflang="id" data-title="Fruktosa" 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-zu mw-list-item"><a href="https://zu.wikipedia.org/wiki/IsiNcithelo" title="IsiNcithelo – Zulu" lang="zu" hreflang="zu" data-title="IsiNcithelo" data-language-autonym="IsiZulu" data-language-local-name="Zulu" class="interlanguage-link-target"><span>IsiZulu</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Fruttosio" title="Fruttosio – Italian" lang="it" hreflang="it" data-title="Fruttosio" 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%A4%D7%A8%D7%95%D7%A7%D7%98%D7%95%D7%96" title="פרוקטוז – Hebrew" lang="he" hreflang="he" data-title="פרוקטוז" 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/Fruktosa" title="Fruktosa – Javanese" lang="jv" hreflang="jv" data-title="Fruktosa" data-language-autonym="Jawa" data-language-local-name="Javanese" class="interlanguage-link-target"><span>Jawa</span></a></li><li class="interlanguage-link interwiki-kk mw-list-item"><a href="https://kk.wikipedia.org/wiki/%D0%A4%D1%80%D1%83%D0%BA%D1%82%D0%BE%D0%B7%D0%B0" title="Фруктоза – Kazakh" lang="kk" hreflang="kk" data-title="Фруктоза" data-language-autonym="Қазақша" data-language-local-name="Kazakh" class="interlanguage-link-target"><span>Қазақша</span></a></li><li class="interlanguage-link interwiki-kw mw-list-item"><a href="https://kw.wikipedia.org/wiki/Fruktos" title="Fruktos – Cornish" lang="kw" hreflang="kw" data-title="Fruktos" data-language-autonym="Kernowek" data-language-local-name="Cornish" class="interlanguage-link-target"><span>Kernowek</span></a></li><li class="interlanguage-link interwiki-ku mw-list-item"><a href="https://ku.wikipedia.org/wiki/Fruktoz" title="Fruktoz – Kurdish" lang="ku" hreflang="ku" data-title="Fruktoz" 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%A4%D1%80%D1%83%D0%BA%D1%82%D0%BE%D0%B7%D0%B0" title="Фруктоза – Kyrgyz" lang="ky" hreflang="ky" data-title="Фруктоза" 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%E0%BB%9D%E0%BA%B2%E0%BA%81%E0%BB%84%E0%BA%A1%E0%BB%89" title="ນ້ຳຕານໝາກໄມ້ – Lao" lang="lo" hreflang="lo" data-title="ນ້ຳຕານໝາກໄມ້" 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/Fructosum" title="Fructosum – Latin" lang="la" hreflang="la" data-title="Fructosum" 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/Fruktoze" title="Fruktoze – Latvian" lang="lv" hreflang="lv" data-title="Fruktoze" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target"><span>Latviešu</span></a></li><li class="interlanguage-link interwiki-lb mw-list-item"><a href="https://lb.wikipedia.org/wiki/Fruktos" title="Fruktos – Luxembourgish" lang="lb" hreflang="lb" data-title="Fruktos" data-language-autonym="Lëtzebuergesch" data-language-local-name="Luxembourgish" class="interlanguage-link-target"><span>Lëtzebuergesch</span></a></li><li class="interlanguage-link interwiki-lt mw-list-item"><a href="https://lt.wikipedia.org/wiki/Fruktoz%C4%97" title="Fruktozė – Lithuanian" lang="lt" hreflang="lt" data-title="Fruktozė" data-language-autonym="Lietuvių" data-language-local-name="Lithuanian" class="interlanguage-link-target"><span>Lietuvių</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Frukt%C3%B3z" title="Fruktóz – Hungarian" lang="hu" hreflang="hu" data-title="Fruktóz" 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%A4%D1%80%D1%83%D0%BA%D1%82%D0%BE%D0%B7%D0%B0" title="Фруктоза – Macedonian" lang="mk" hreflang="mk" data-title="Фруктоза" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-mg mw-list-item"><a href="https://mg.wikipedia.org/wiki/Frokt%C3%B4zy" title="Froktôzy – Malagasy" lang="mg" hreflang="mg" data-title="Froktôzy" data-language-autonym="Malagasy" data-language-local-name="Malagasy" class="interlanguage-link-target"><span>Malagasy</span></a></li><li class="interlanguage-link interwiki-arz mw-list-item"><a href="https://arz.wikipedia.org/wiki/%D9%81%D8%B1%D9%83%D8%AA%D9%88%D8%B2" title="فركتوز – Egyptian Arabic" lang="arz" hreflang="arz" data-title="فركتوز" 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/Fruktosa" title="Fruktosa – Malay" lang="ms" hreflang="ms" data-title="Fruktosa" 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-mn mw-list-item"><a href="https://mn.wikipedia.org/wiki/%D0%A4%D1%80%D1%83%D0%BA%D1%82%D0%BE%D0%B7" title="Фруктоз – Mongolian" lang="mn" hreflang="mn" data-title="Фруктоз" data-language-autonym="Монгол" data-language-local-name="Mongolian" class="interlanguage-link-target"><span>Монгол</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Fructose" title="Fructose – Dutch" lang="nl" hreflang="nl" data-title="Fructose" 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%83%95%E3%83%AB%E3%82%AF%E3%83%88%E3%83%BC%E3%82%B9" title="フルクトース – Japanese" lang="ja" hreflang="ja" data-title="フルクトース" 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-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Fruktsukker" title="Fruktsukker – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Fruktsukker" 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/Fruktose" title="Fruktose – Norwegian Nynorsk" lang="nn" hreflang="nn" data-title="Fruktose" 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/Fruct%C3%B2sa" title="Fructòsa – Occitan" lang="oc" hreflang="oc" data-title="Fructòsa" data-language-autonym="Occitan" data-language-local-name="Occitan" class="interlanguage-link-target"><span>Occitan</span></a></li><li class="interlanguage-link interwiki-uz mw-list-item"><a href="https://uz.wikipedia.org/wiki/Fruktoza" title="Fruktoza – Uzbek" lang="uz" hreflang="uz" data-title="Fruktoza" 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-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Fruktoza" title="Fruktoza – Polish" lang="pl" hreflang="pl" data-title="Fruktoza" 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/Frutose" title="Frutose – Portuguese" lang="pt" hreflang="pt" data-title="Frutose" 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/Fructoz%C4%83" title="Fructoză – Romanian" lang="ro" hreflang="ro" data-title="Fructoză" 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/Wayu_misk%27i" title="Wayu misk'i – Quechua" lang="qu" hreflang="qu" data-title="Wayu misk'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%A4%D1%80%D1%83%D0%BA%D1%82%D0%BE%D0%B7%D0%B0" title="Фруктоза – Russian" lang="ru" hreflang="ru" data-title="Фруктоза" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sco mw-list-item"><a href="https://sco.wikipedia.org/wiki/Fructose" title="Fructose – Scots" lang="sco" hreflang="sco" data-title="Fructose" data-language-autonym="Scots" data-language-local-name="Scots" class="interlanguage-link-target"><span>Scots</span></a></li><li class="interlanguage-link interwiki-sq mw-list-item"><a href="https://sq.wikipedia.org/wiki/Fruktoza" title="Fruktoza – Albanian" lang="sq" hreflang="sq" data-title="Fruktoza" data-language-autonym="Shqip" data-language-local-name="Albanian" class="interlanguage-link-target"><span>Shqip</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Fructose" title="Fructose – Simple English" lang="en-simple" hreflang="en-simple" data-title="Fructose" 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/Frukt%C3%B3za" title="Fruktóza – Slovak" lang="sk" hreflang="sk" data-title="Fruktóza" 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/Fruktoza" title="Fruktoza – Slovenian" lang="sl" hreflang="sl" data-title="Fruktoza" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/%D0%A4%D1%80%D1%83%D0%BA%D1%82%D0%BE%D0%B7%D0%B0" title="Фруктоза – Serbian" lang="sr" hreflang="sr" data-title="Фруктоза" 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/Fruktoza" title="Fruktoza – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Fruktoza" 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 mw-list-item"><a href="https://su.wikipedia.org/wiki/Fruktosa" title="Fruktosa – Sundanese" lang="su" hreflang="su" data-title="Fruktosa" 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/Fruktoosi" title="Fruktoosi – Finnish" lang="fi" hreflang="fi" data-title="Fruktoosi" 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/Fruktos" title="Fruktos – Swedish" lang="sv" hreflang="sv" data-title="Fruktos" 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/Pruktosa" title="Pruktosa – Tagalog" lang="tl" hreflang="tl" data-title="Pruktosa" 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%AA%E0%AF%81%E0%AE%B0%E0%AF%81%E0%AE%95%E0%AF%8D%E0%AE%9F%E0%AF%8B%E0%AE%9A%E0%AF%81" title="புருக்டோசு – Tamil" lang="ta" hreflang="ta" data-title="புருக்டோசு" 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/Fruktoza" title="Fruktoza – Tatar" lang="tt" hreflang="tt" data-title="Fruktoza" 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-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B8%9F%E0%B8%A3%E0%B8%B1%E0%B8%81%E0%B9%82%E0%B8%97%E0%B8%AA" title="ฟรักโทส – Thai" lang="th" hreflang="th" data-title="ฟรักโทส" 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%A4%D1%80%D1%83%D0%BA%D1%82%D0%BE%D0%B7%D0%B0" title="Фруктоза – Tajik" lang="tg" hreflang="tg" data-title="Фруктоза" 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/Fruktoz" title="Fruktoz – Turkish" lang="tr" hreflang="tr" data-title="Fruktoz" 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%A4%D1%80%D1%83%D0%BA%D1%82%D0%BE%D0%B7%D0%B0" title="Фруктоза – Ukrainian" lang="uk" hreflang="uk" data-title="Фруктоза" 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/%D9%81%D8%B1%DA%A9%D9%B9%D9%88%D8%B3" title="فرکٹوس – Urdu" lang="ur" hreflang="ur" data-title="فرکٹوس" data-language-autonym="اردو" data-language-local-name="Urdu" class="interlanguage-link-target"><span>اردو</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Fructose" title="Fructose – Vietnamese" lang="vi" hreflang="vi" data-title="Fructose" 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/Fructose" title="Fructose – Waray" lang="war" hreflang="war" data-title="Fructose" 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/%E6%9E%9C%E7%B3%96" title="果糖 – Wu" lang="wuu" hreflang="wuu" data-title="果糖" 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%8F%93%E9%86%A3" title="菓醣 – Cantonese" lang="yue" hreflang="yue" data-title="菓醣" data-language-autonym="粵語" data-language-local-name="Cantonese" class="interlanguage-link-target"><span>粵語</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E6%9E%9C%E7%B3%96" title="果糖 – Chinese" lang="zh" hreflang="zh" data-title="果糖" data-language-autonym="中文" data-language-local-name="Chinese" 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class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><style data-mw-deduplicate="TemplateStyles:r1251242444">.mw-parser-output .ambox{border:1px solid #a2a9b1;border-left:10px solid #36c;background-color:#fbfbfb;box-sizing:border-box}.mw-parser-output .ambox+link+.ambox,.mw-parser-output .ambox+link+style+.ambox,.mw-parser-output .ambox+link+link+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+style+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+link+.ambox{margin-top:-1px}html body.mediawiki .mw-parser-output .ambox.mbox-small-left{margin:4px 1em 4px 0;overflow:hidden;width:238px;border-collapse:collapse;font-size:88%;line-height:1.25em}.mw-parser-output .ambox-speedy{border-left:10px solid #b32424;background-color:#fee7e6}.mw-parser-output .ambox-delete{border-left:10px solid #b32424}.mw-parser-output .ambox-content{border-left:10px solid #f28500}.mw-parser-output .ambox-style{border-left:10px solid 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width="40" height="40" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/f2/Edit-clear.svg/60px-Edit-clear.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/f2/Edit-clear.svg/80px-Edit-clear.svg.png 2x" data-file-width="48" data-file-height="48" /></span></span></div></td><td class="mbox-text"><div class="mbox-text-span">This article's <b><a href="/wiki/Wikipedia:Manual_of_Style/Lead_section" title="Wikipedia:Manual of Style/Lead section">lead section</a> contains information that is not included elsewhere in the article</b>.<span class="hide-when-compact"> If the information is appropriate for the lead of the article, this information should also be included in the body of the article.</span> <span class="date-container"><i>(<span class="date">March 2023</span>)</i></span><span class="hide-when-compact"><i> (<small><a href="/wiki/Help:Maintenance_template_removal" title="Help:Maintenance template removal">Learn how and when to remove this message</a></small>)</i></span></div></td></tr></tbody></table> <div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Simple ketonic monosaccharide found in many plants</div> <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> <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>-Fructose </caption> <tbody><tr> <td colspan="2" class="borderless" style="text-align:center"> <table border="0" style="width:100%;display:inline-table;"> <tbody><tr> <td style="border-right:1px solid #aaa; width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Skeletal_Structure_of_Cyclic_D-Fructose.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/64/Skeletal_Structure_of_Cyclic_D-Fructose.svg/150px-Skeletal_Structure_of_Cyclic_D-Fructose.svg.png" decoding="async" width="150" height="74" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/64/Skeletal_Structure_of_Cyclic_D-Fructose.svg/225px-Skeletal_Structure_of_Cyclic_D-Fructose.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/64/Skeletal_Structure_of_Cyclic_D-Fructose.svg/300px-Skeletal_Structure_of_Cyclic_D-Fructose.svg.png 2x" data-file-width="512" data-file-height="252" /></a><figcaption></figcaption></figure><div style="text-align:center"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-Fructofuranose</div> </td> <td style="width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:D-Fructose.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e5/D-Fructose.svg/60px-D-Fructose.svg.png" decoding="async" width="60" height="100" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e5/D-Fructose.svg/90px-D-Fructose.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e5/D-Fructose.svg/120px-D-Fructose.svg.png 2x" data-file-width="126" data-file-height="209" /></a><figcaption></figcaption></figure><div style="text-align:center"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-Fructose (open-chain form)</div> </td></tr></tbody></table> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:Beta-D-Fructofuranose.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/67/Beta-D-Fructofuranose.svg/220px-Beta-D-Fructofuranose.svg.png" decoding="async" width="220" height="188" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/67/Beta-D-Fructofuranose.svg/330px-Beta-D-Fructofuranose.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/67/Beta-D-Fructofuranose.svg/440px-Beta-D-Fructofuranose.svg.png 2x" data-file-width="179" data-file-height="153" /></a></span><br /><div style="text-align:center;"><a href="/wiki/Haworth_projection" title="Haworth projection">Haworth projection</a> of β-<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-fructofuranose</div> </td></tr> <tr> <td colspan="2" class="borderless" style="text-align:center"> <table border="0" style="width:100%;display:inline-table;"> <tbody><tr> <td style="border-right:1px solid #aaa; width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Beta-D-fructofuranose-from-xtal-view-1-3D-bs-17.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/02/Beta-D-fructofuranose-from-xtal-view-1-3D-bs-17.png/110px-Beta-D-fructofuranose-from-xtal-view-1-3D-bs-17.png" decoding="async" width="110" height="89" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/02/Beta-D-fructofuranose-from-xtal-view-1-3D-bs-17.png/165px-Beta-D-fructofuranose-from-xtal-view-1-3D-bs-17.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/02/Beta-D-fructofuranose-from-xtal-view-1-3D-bs-17.png/220px-Beta-D-fructofuranose-from-xtal-view-1-3D-bs-17.png 2x" data-file-width="2927" data-file-height="2369" /></a><figcaption></figcaption></figure><div style="text-align:center"><a href="/wiki/Ball-and-stick_model" title="Ball-and-stick model">Ball-and-stick model</a> of β-<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-fructo<a href="/wiki/Furanose" title="Furanose">furanose</a></div> </td> <td style="width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Beta-D-fructopyranose-from-xtal-view-2-3D-bs-17.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/92/Beta-D-fructopyranose-from-xtal-view-2-3D-bs-17.png/110px-Beta-D-fructopyranose-from-xtal-view-2-3D-bs-17.png" decoding="async" width="110" height="86" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/92/Beta-D-fructopyranose-from-xtal-view-2-3D-bs-17.png/165px-Beta-D-fructopyranose-from-xtal-view-2-3D-bs-17.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/92/Beta-D-fructopyranose-from-xtal-view-2-3D-bs-17.png/220px-Beta-D-fructopyranose-from-xtal-view-2-3D-bs-17.png 2x" data-file-width="2793" data-file-height="2175" /></a><figcaption></figcaption></figure><div style="text-align:center">Ball-and-stick model of β-<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-fructo<a href="/wiki/Pyranose" title="Pyranose">pyranose</a></div> </td></tr></tbody></table> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Names </th></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;"><small>D</small>-<i>arabino</i>-Hex-2-ulose<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup></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;">(3<i>S</i>,4<i>R</i>,5<i>R</i>)-1,3,4,5,6-Pentahydroxyhexan-2-one</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;">Fruit sugar,<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> levulose,<sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-fructofuranose, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-fructose, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-arabino-hexulose</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=57-48-7">57-48-7</a></span><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></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><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=O%5BC%40H%5D1%5BC%40H%5D%28O%29%5BC%40H%5D%28O%5BC%40%5D1%28O%29CO%29CO">Interactive image</a></span></li></ul></div> </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=28645">CHEBI:28645</a></span><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></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/ChEMBL604608">ChEMBL604608</a></span><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></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.388775.html">388775</a></span><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></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a> </td> <td><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.000.303">100.000.303</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q122043#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span> </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>200-333-3</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/C02336">C02336</a></span><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></sup></li></ul></div> </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/5984">5984</a></span></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/6YSS42VSEV">6YSS42VSEV</a></span><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></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID5023081">DTXSID5023081</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q122043#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></span></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/c7-1-3-4(9)5(10)6(11,2-8)12-3/h3-5,7-11H,1-2H2/t3-,4-,5+,6-/m1/s1<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></sup></div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: RFSUNEUAIZKAJO-ARQDHWQXSA-N<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></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%;">O[C@H]1[C@H](O)[C@H](O[C@]1(O)CO)CO</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> g·mol<sup>−1</sup>   </td></tr> <tr> <td><a href="/wiki/Density" title="Density">Density</a> </td> <td>1.694 g/cm<sup>3</sup> </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>103 °C (217 °F; 376 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>~4000 g/L (25 °C) </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> (χ)</div> </td> <td>−102.60×10<sup>−6</sup> cm<sup>3</sup>/mol </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/Standard_enthalpy_change_of_combustion" class="mw-redirect" title="Standard enthalpy change of combustion">Std enthalpy of<br />combustion</a> <span style="font-size:112%;">(Δ<sub>c</sub><i>H</i><sup>⦵</sup><sub>298</sub>)</span></div> </td> <td>675.6 kcal/mol (2,827 kJ/mol)<sup id="cite_ref-CRC_4-0" class="reference"><a href="#cite_note-CRC-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> (<a href="/wiki/Higher_heating_value" class="mw-redirect" title="Higher heating value">Higher heating value</a>) </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_V06" title="ATC code V06">V06DC02</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=V06DC02">WHO</a></span>)  </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Hazards </th></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;"><b>Lethal dose</b> or concentration (LD, LC): </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">LD<sub>50</sub> (<a href="/wiki/Lethal_dose#LD50" title="Lethal dose">median dose</a>)</div> </td> <td>15000 mg/kg (intravenous, rabbit)<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </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 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"><div style="text-align:center;"><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/12px-X_mark.svg.png" decoding="async" width="12" height="14" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/18px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/24px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span> <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=477167440&page2=Fructose">verify</a></span> (<a href="/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validation" title="Wikipedia:WikiProject Chemicals/Chembox validation">what is</a> <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> ?) </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>Fructose</b> (<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="'f' in 'find'">f</span><span title="'r' in 'rye'">r</span><span title="/ʌ/: 'u' in 'cut'">ʌ</span><span title="'k' in 'kind'">k</span><span title="'t' in 'tie'">t</span><span title="/oʊ/: 'o' in 'code'">oʊ</span><span title="'s' in 'sigh'">s</span></span>,<span class="wrap"> </span>-<span style="border-bottom:1px dotted"><span title="/oʊ/: 'o' in 'code'">oʊ</span><span title="'z' in 'zoom'">z</span></span>/</a></span></span>), or <b>fruit sugar</b>, is a <a href="/wiki/Ketose" title="Ketose">ketonic</a> <a href="/wiki/Monosaccharide" title="Monosaccharide">simple sugar</a> found in many plants, where it is often bonded to <a href="/wiki/Glucose" title="Glucose">glucose</a> to form the <a href="/wiki/Disaccharide" title="Disaccharide">disaccharide</a> <a href="/wiki/Sucrose" title="Sucrose">sucrose</a>. It is one of the three dietary monosaccharides, along with <a href="/wiki/Glucose" title="Glucose">glucose</a> and <a href="/wiki/Galactose" title="Galactose">galactose</a>, that are absorbed by the gut directly into the blood of the <a href="/wiki/Portal_vein" title="Portal vein">portal vein</a> during <a href="/wiki/Digestion" title="Digestion">digestion</a>. The liver then converts most fructose and galactose into glucose for distribution in the bloodstream or deposition into glycogen. <sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p><p>Fructose was discovered by French chemist <a href="/wiki/Augustin-Pierre_Dubrunfaut" title="Augustin-Pierre Dubrunfaut">Augustin-Pierre Dubrunfaut</a> in 1847.<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> The name "fructose" was coined in 1857 by the English chemist <a href="/wiki/William_Allen_Miller" title="William Allen Miller">William Allen Miller</a>.<sup id="cite_ref-Miller_9-0" class="reference"><a href="#cite_note-Miller-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> Pure, dry fructose is a sweet, white, odorless, crystalline solid, and is the most water-soluble of all the sugars.<sup id="cite_ref-Hyvonen&Koivistoinen1982_10-0" class="reference"><a href="#cite_note-Hyvonen&Koivistoinen1982-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> Fructose is found in <a href="/wiki/Honey" title="Honey">honey</a>, tree and vine fruits, flowers, <a href="/wiki/Berry" title="Berry">berries</a>, and most <a href="/wiki/List_of_root_vegetables" class="mw-redirect" title="List of root vegetables">root vegetables</a>. </p><p>Commercially, fructose is derived from <a href="/wiki/Sugar_cane" class="mw-redirect" title="Sugar cane">sugar cane</a>, <a href="/wiki/Sugar_beet" title="Sugar beet">sugar beets</a>, and <a href="/wiki/Maize" title="Maize">maize</a>. <a href="/wiki/High-fructose_corn_syrup" title="High-fructose corn syrup">High-fructose corn syrup</a> is a <a href="/wiki/Mixture" title="Mixture">mixture</a> of glucose and fructose as monosaccharides. Sucrose is a <a href="/wiki/Chemical_compound" title="Chemical compound">compound</a> with one molecule of glucose <a href="/wiki/Covalent_bond" title="Covalent bond">covalently</a> linked to one molecule of fructose. All forms of fructose, including those found in fruits and juices, are commonly added to foods and drinks for <a href="/wiki/Palatability" title="Palatability">palatability</a> and <a href="/wiki/Taste" title="Taste">taste</a> enhancement, and for browning of some foods, such as baked goods. As of 2004, about 240,000 <a href="/wiki/Tonne" title="Tonne">tonnes</a> of crystalline fructose were being produced annually.<sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p><p>Excessive consumption of sugars, including fructose, (especially from sugar-sweetened beverages) may contribute to <a href="/wiki/Insulin_resistance" title="Insulin resistance">insulin resistance</a>, <a href="/wiki/Obesity" title="Obesity">obesity</a>, elevated <a href="/wiki/Low-density_lipoprotein" title="Low-density lipoprotein">LDL cholesterol</a> and <a href="/wiki/Triglyceride" title="Triglyceride">triglycerides</a>, leading to <a href="/wiki/Metabolic_syndrome" title="Metabolic syndrome">metabolic syndrome</a>. The <a href="/wiki/European_Food_Safety_Authority" title="European Food Safety Authority">European Food Safety Authority</a> (EFSA) stated in 2011 that fructose may be preferable over sucrose and glucose in sugar-sweetened foods and beverages because of its lower effect on <a href="/wiki/Postprandial" class="mw-redirect" title="Postprandial">postprandial</a> <a href="/wiki/Blood_sugar" class="mw-redirect" title="Blood sugar">blood sugar</a> levels,<sup id="cite_ref-efsa11_12-0" class="reference"><a href="#cite_note-efsa11-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> while also noting the potential downside that "high intakes of fructose may lead to metabolic complications such as <a href="/wiki/Dyslipidaemia" class="mw-redirect" title="Dyslipidaemia">dyslipidaemia</a>, insulin resistance, and increased visceral adiposity".<sup id="cite_ref-efsa11_12-1" class="reference"><a href="#cite_note-efsa11-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-efsa2-22_13-0" class="reference"><a href="#cite_note-efsa2-22-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> The UK's Scientific Advisory Committee on Nutrition in 2015 disputed the claims of fructose causing metabolic disorders, stating that "there is insufficient evidence to demonstrate that fructose intake, at levels consumed in the normal UK diet, leads to adverse health outcomes independent of any effects related to its presence as a component of total and free sugars."<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Etymology">Etymology</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fructose&action=edit&section=1" title="Edit section: Etymology"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The word "fructose" was coined in 1857 from the Latin for <i>fructus</i> (fruit) and the generic chemical suffix for sugars, <i><a href="/wiki/-ose" title="-ose">-ose</a></i>.<sup id="cite_ref-Miller_9-1" class="reference"><a href="#cite_note-Miller-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-oed_15-0" class="reference"><a href="#cite_note-oed-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> It is also called fruit sugar and levulose or laevulose, due to its ability to rotate plane polarised light in a <a href="/wiki/Optical_rotation" title="Optical rotation">laevorotary</a> fashion (anti-clockwise/to the left) when a beam is shone through it in solution. Likewise, <a href="/wiki/Glucose" title="Glucose">dextrose</a> (an isomer of glucose) is given its name due to its ability to rotate plane polarised light in a <a href="/wiki/Optical_rotation" title="Optical rotation">dextrorotary</a> fashion (clockwise/to the right).<sup id="cite_ref-oed_15-1" class="reference"><a href="#cite_note-oed-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Chemical_properties">Chemical properties</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fructose&action=edit&section=2" title="Edit section: Chemical properties"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Isomeric_forms_of_fructose.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b0/Isomeric_forms_of_fructose.svg/375px-Isomeric_forms_of_fructose.svg.png" decoding="async" width="375" height="182" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b0/Isomeric_forms_of_fructose.svg/563px-Isomeric_forms_of_fructose.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b0/Isomeric_forms_of_fructose.svg/750px-Isomeric_forms_of_fructose.svg.png 2x" data-file-width="512" data-file-height="248" /></a><figcaption><b>Figure 1:</b> Relationship between the <a href="/wiki/Open-chain" class="mw-redirect" title="Open-chain">acyclic</a> and the cyclic (<a href="/wiki/Hemiketal" class="mw-redirect" title="Hemiketal">hemiketal</a>) isomers of fructose</figcaption></figure> <figure typeof="mw:File/Thumb"><a href="/wiki/File:DL-Fructose_num.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/50/DL-Fructose_num.svg/255px-DL-Fructose_num.svg.png" decoding="async" width="255" height="208" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/50/DL-Fructose_num.svg/383px-DL-Fructose_num.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/50/DL-Fructose_num.svg/510px-DL-Fructose_num.svg.png 2x" data-file-width="512" data-file-height="418" /></a><figcaption><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>-isomers of fructose (open-chain form)</figcaption></figure> <p>Fructose is a 6-carbon polyhydroxyketone.<sup id="cite_ref-pubchem_16-0" class="reference"><a href="#cite_note-pubchem-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> Crystalline fructose adopts a cyclic six-membered structure, called β-<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-fructopyranose, owing to the stability of its <a href="/wiki/Hemiketal" class="mw-redirect" title="Hemiketal">hemiketal</a> and internal hydrogen-bonding. In solution, fructose exists as an <a href="/wiki/Chemical_equilibrium" title="Chemical equilibrium">equilibrium</a> mixture of the <a href="/wiki/Tautomers" class="mw-redirect" title="Tautomers">tautomers</a> β-<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-fructo<a href="/wiki/Pyranose" title="Pyranose">pyranose</a>, β-<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-fructo<a href="/wiki/Furanose" title="Furanose">furanose</a>, α-<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-fructofuranose, α-<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-fructopyranose and <i>keto</i>-<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-fructose (the non-cyclic form).<sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </p><p>The distribution of <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-fructose tautomers in solution is related to several variables, such as solvent and temperature.<sup id="cite_ref-18" class="reference"><a href="#cite_note-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-Fructopyranose and <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-fructofuranose distributions in water have been identified multiple times as roughly 70% fructopyranose and 22% fructofuranose.<sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Reactions">Reactions</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fructose&action=edit&section=3" title="Edit section: Reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading4"><h4 id="Fructose_and_fermentation">Fructose and fermentation</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fructose&action=edit&section=4" title="Edit section: Fructose and fermentation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Fructose may be anaerobically <a href="/wiki/Ethanol_fermentation" title="Ethanol fermentation">fermented</a> by <a href="/wiki/Yeast" title="Yeast">yeast</a> and <a href="/wiki/Bacteria" title="Bacteria">bacteria</a>.<sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> Yeast enzymes convert sugar (<a href="/wiki/Sucrose" title="Sucrose">sucrose</a>, <a href="/wiki/Glucose" title="Glucose">glucose</a>, and fructose, but not <a href="/wiki/Lactose" title="Lactose">lactose</a>) to <a href="/wiki/Ethanol" title="Ethanol">ethanol</a> and <a href="/wiki/Carbon_dioxide" title="Carbon dioxide">carbon dioxide</a>.<sup id="cite_ref-21" class="reference"><a href="#cite_note-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> Some of the carbon dioxide produced during fermentation will remain dissolved in water, where it will reach equilibrium with <a href="/wiki/Carbonic_acid" title="Carbonic acid">carbonic acid</a>. The dissolved carbon dioxide and carbonic acid produce the carbonation in some <a href="/wiki/Fermented_beverage" class="mw-redirect" title="Fermented beverage">fermented beverages</a>, such as <a href="/wiki/Champagne" title="Champagne">champagne</a>. </p> <div class="mw-heading mw-heading4"><h4 id="Fructose_and_Maillard_reaction">Fructose and Maillard reaction</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fructose&action=edit&section=5" title="Edit section: Fructose and Maillard reaction"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Fructose undergoes the <a href="/wiki/Maillard_reaction" title="Maillard reaction">Maillard reaction</a>, non-enzymatic browning, with <a href="/wiki/Amino_acid" title="Amino acid">amino acids</a>. Because fructose exists to a greater extent in the open-chain form than does glucose, the initial stages of the Maillard reaction occur more rapidly than with glucose. Therefore, fructose has potential to contribute to changes in food <a href="/wiki/Palatability" title="Palatability">palatability</a>, as well as other nutritional effects, such as excessive browning, volume and tenderness reduction during cake preparation, and formation of <a href="/wiki/Mutagenic" class="mw-redirect" title="Mutagenic">mutagenic</a> compounds.<sup id="cite_ref-22" class="reference"><a href="#cite_note-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Dehydration">Dehydration</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fructose&action=edit&section=6" title="Edit section: Dehydration"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Fructose readily dehydrates to give <a href="/wiki/Hydroxymethylfurfural" title="Hydroxymethylfurfural">hydroxymethylfurfural</a> ("HMF", <span class="chemf nowrap">C<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">6</sub></span></span>H<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">6</sub></span></span>O<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">3</sub></span></span></span>), which can be processed into liquid <a href="/wiki/2,5-Dimethylfuran" title="2,5-Dimethylfuran">dimethylfuran</a> (<span class="chemf nowrap">C<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">6</sub></span></span>H<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">8</sub></span></span>O</span>). This process, in the future, may become part of a low-cost, carbon-neutral system to produce replacements for petrol and diesel from plants.<sup id="cite_ref-23" class="reference"><a href="#cite_note-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Physical_and_functional_properties">Physical and functional properties</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fructose&action=edit&section=7" title="Edit section: Physical and functional properties"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Sweetness_of_fructose">Sweetness of fructose</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fructose&action=edit&section=8" title="Edit section: Sweetness of fructose"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></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">See also: <a href="/wiki/Sweetness#Examples_of_sweet_substances" title="Sweetness">Sweetness § Examples of sweet substances</a></div> <p>The primary reason that fructose is used commercially in foods and beverages, besides its low cost, is its high relative sweetness. It is the sweetest of all naturally occurring <a href="/wiki/Carbohydrate" title="Carbohydrate">carbohydrates</a>. The relative sweetness of fructose has been reported in the range of 1.2–1.8 times that of sucrose.<sup id="cite_ref-Hanover_24-0" class="reference"><a href="#cite_note-Hanover-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Oregon_State_University_25-0" class="reference"><a href="#cite_note-Oregon_State_University-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Kirk-Othmer_26-0" class="reference"><a href="#cite_note-Kirk-Othmer-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-27" class="reference"><a href="#cite_note-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> However, it is the 6-membered ring form of fructose that is sweeter; the 5-membered ring form tastes about the same as usual table sugar. Warming fructose leads to formation of the 5-membered ring form.<sup id="cite_ref-28" class="reference"><a href="#cite_note-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> Therefore, the relative sweetness decreases with increasing temperature. However, it has been observed that the absolute sweetness of fructose is identical at 5 °C as 50 °C and thus the relative sweetness to sucrose is not due to <a href="/wiki/Anomeric" class="mw-redirect" title="Anomeric">anomeric</a> distribution but a decrease in the absolute sweetness of sucrose at higher temperatures.<sup id="cite_ref-Kirk-Othmer_26-1" class="reference"><a href="#cite_note-Kirk-Othmer-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-halign-center" 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/400px-Relativesweetness.svg.png" decoding="async" width="400" height="258" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/bd/Relativesweetness.svg/600px-Relativesweetness.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/bd/Relativesweetness.svg/800px-Relativesweetness.svg.png 2x" data-file-width="512" data-file-height="330" /></a><figcaption><b>Figure 2:</b> Relative sweetness of sugars and sweeteners</figcaption></figure> <p>The sweetness of fructose is perceived earlier than that of sucrose or glucose, and the taste sensation reaches a peak (higher than that of sucrose), and diminishes more quickly than that of sucrose. Fructose can also enhance other flavors in the system.<sup id="cite_ref-Hanover_24-1" class="reference"><a href="#cite_note-Hanover-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Kirk-Othmer_26-2" class="reference"><a href="#cite_note-Kirk-Othmer-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> </p><p>Fructose exhibits a sweetness synergy effect when used in combination with other sweeteners. The relative sweetness of fructose blended with sucrose, aspartame, or saccharin is perceived to be greater than the sweetness calculated from individual components.<sup id="cite_ref-Nabors_29-0" class="reference"><a href="#cite_note-Nabors-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Kirk-Othmer_26-3" class="reference"><a href="#cite_note-Kirk-Othmer-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Fructose_solubility_and_crystallization">Fructose solubility and crystallization</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fructose&action=edit&section=9" title="Edit section: Fructose solubility and crystallization"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Fructose has higher water solubility than other sugars, as well as other sugar alcohols. Fructose is, therefore, difficult to crystallize from an aqueous solution.<sup id="cite_ref-Hanover_24-2" class="reference"><a href="#cite_note-Hanover-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> Sugar mixes containing fructose, such as candies, are softer than those containing other sugars because of the greater solubility of fructose.<sup id="cite_ref-30" class="reference"><a href="#cite_note-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Fructose_hygroscopicity_and_humectancy">Fructose hygroscopicity and humectancy</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fructose&action=edit&section=10" title="Edit section: Fructose hygroscopicity and humectancy"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Fructose is quicker to absorb moisture and slower to release it to the environment than sucrose, glucose, or other nutritive sweeteners.<sup id="cite_ref-Nabors_29-1" class="reference"><a href="#cite_note-Nabors-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> Fructose is an excellent humectant and retains moisture for a long period of time even at low <a href="/wiki/Relative_humidity" class="mw-redirect" title="Relative humidity">relative humidity</a> (RH). Therefore, fructose can contribute a more palatable texture, and longer shelf life to the food products in which it is used.<sup id="cite_ref-Hanover_24-3" class="reference"><a href="#cite_note-Hanover-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Freezing_point">Freezing point</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fructose&action=edit&section=11" title="Edit section: Freezing point"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Fructose has a greater effect on freezing point depression than disaccharides or oligosaccharides, which may protect the integrity of cell walls of fruit by reducing ice crystal formation. However, this characteristic may be undesirable in soft-serve or hard-frozen dairy desserts.<sup id="cite_ref-Hanover_24-4" class="reference"><a href="#cite_note-Hanover-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Fructose_and_starch_functionality_in_food_systems">Fructose and starch functionality in food systems</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fructose&action=edit&section=12" title="Edit section: Fructose and starch functionality in food systems"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Fructose increases starch viscosity more rapidly and achieves a higher final viscosity than sucrose because fructose lowers the temperature required during <a href="/wiki/Starch_gelatinization" title="Starch gelatinization">gelatinizing of starch</a>, causing a greater final viscosity.<sup id="cite_ref-31" class="reference"><a href="#cite_note-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> </p><p>Although some artificial sweeteners are not suitable for home baking, many traditional recipes use fructose.<sup id="cite_ref-32" class="reference"><a href="#cite_note-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Food_sources">Food sources</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fructose&action=edit&section=13" title="Edit section: Food sources"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1251242444"><table class="box-More_citations_needed plainlinks metadata ambox ambox-content ambox-Refimprove" role="presentation"><tbody><tr><td class="mbox-image"><div class="mbox-image-div"><span typeof="mw:File"><a href="/wiki/File:Question_book-new.svg" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/9/99/Question_book-new.svg/50px-Question_book-new.svg.png" decoding="async" width="50" height="39" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/9/99/Question_book-new.svg/75px-Question_book-new.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/9/99/Question_book-new.svg/100px-Question_book-new.svg.png 2x" data-file-width="512" data-file-height="399" /></a></span></div></td><td class="mbox-text"><div class="mbox-text-span">This section <b>needs additional citations for <a href="/wiki/Wikipedia:Verifiability" title="Wikipedia:Verifiability">verification</a></b>.<span class="hide-when-compact"> Please help <a href="/wiki/Special:EditPage/Fructose" title="Special:EditPage/Fructose">improve this article</a> by <a href="/wiki/Help:Referencing_for_beginners" title="Help:Referencing for beginners">adding citations to reliable sources</a> in this section. Unsourced material may be challenged and removed.<br /><small><span class="plainlinks"><i>Find sources:</i> <a rel="nofollow" class="external text" href="https://www.google.com/search?as_eq=wikipedia&q=%22Fructose%22">"Fructose"</a> – <a rel="nofollow" class="external text" href="https://www.google.com/search?tbm=nws&q=%22Fructose%22+-wikipedia&tbs=ar:1">news</a> <b>·</b> <a rel="nofollow" class="external text" href="https://www.google.com/search?&q=%22Fructose%22&tbs=bkt:s&tbm=bks">newspapers</a> <b>·</b> <a rel="nofollow" class="external text" href="https://www.google.com/search?tbs=bks:1&q=%22Fructose%22+-wikipedia">books</a> <b>·</b> <a rel="nofollow" class="external text" href="https://scholar.google.com/scholar?q=%22Fructose%22">scholar</a> <b>·</b> <a rel="nofollow" class="external text" href="https://www.jstor.org/action/doBasicSearch?Query=%22Fructose%22&acc=on&wc=on">JSTOR</a></span></small></span> <span class="date-container"><i>(<span class="date">December 2017</span>)</i></span><span class="hide-when-compact"><i> (<small><a href="/wiki/Help:Maintenance_template_removal" title="Help:Maintenance template removal">Learn how and when to remove this message</a></small>)</i></span></div></td></tr></tbody></table> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Table_fructose.JPG" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/73/Table_fructose.JPG/220px-Table_fructose.JPG" decoding="async" width="220" height="147" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/73/Table_fructose.JPG/330px-Table_fructose.JPG 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/73/Table_fructose.JPG/440px-Table_fructose.JPG 2x" data-file-width="6000" data-file-height="4000" /></a><figcaption>Crystalline fructose</figcaption></figure> <p>Natural sources of fructose include fruits, vegetables (including sugar cane), and honey.<sup id="cite_ref-33" class="reference"><a href="#cite_note-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> Fructose is often further concentrated from these sources. The highest dietary sources of fructose, besides pure crystalline fructose, are foods containing <a href="/wiki/White_sugar" title="White sugar">white sugar</a> (sucrose), <a href="/wiki/High-fructose_corn_syrup" title="High-fructose corn syrup">high-fructose corn syrup</a>, <a href="/wiki/Agave_nectar" class="mw-redirect" title="Agave nectar">agave nectar</a>, <a href="/wiki/Honey" title="Honey">honey</a>, <a href="/wiki/Molasses" title="Molasses">molasses</a>, <a href="/wiki/Maple_syrup" title="Maple syrup">maple syrup</a>, fruit and fruit <a href="/wiki/Juice" title="Juice">juices</a>, as these have the highest percentages of fructose (including fructose in sucrose) per serving compared to other common foods and ingredients. Fructose exists in foods either as a free <a href="/wiki/Monosaccharide" title="Monosaccharide">monosaccharide</a> or bound to glucose as sucrose, a <a href="/wiki/Disaccharide" title="Disaccharide">disaccharide</a>. Fructose, glucose, and sucrose may all be present in food; however, different foods will have varying levels of each of these three sugars. </p><p>The sugar contents of common fruits and vegetables are presented in Table 1. In general, in foods that contain free fructose, the ratio of fructose to glucose is approximately 1:1; that is, foods with fructose usually contain about an equal amount of free glucose. A value that is above 1 indicates a higher proportion of fructose to glucose and below 1 a lower proportion. Some fruits have larger proportions of fructose to glucose compared to others. For example, <a href="/wiki/Apple" title="Apple">apples</a> and <a href="/wiki/Pear" title="Pear">pears</a> contain more than twice as much free fructose as glucose, while for <a href="/wiki/Apricot" title="Apricot">apricots</a> the proportion is less than half as much fructose as glucose. </p><p>Apple and pear juices are of particular interest to <a href="/wiki/Pediatrics" title="Pediatrics">pediatricians</a> because the high concentrations of free fructose in these juices can cause <a href="/wiki/Diarrhea" title="Diarrhea">diarrhea</a> in children. The cells (<a href="/wiki/Enterocyte" title="Enterocyte">enterocytes</a>) that line children's <a href="/wiki/Small_intestine" title="Small intestine">small intestines</a> have less affinity for fructose <a href="/wiki/Small_Intestine#Absorptions" class="mw-redirect" title="Small Intestine">absorption</a> than for glucose and sucrose.<sup id="cite_ref-AJCN_fructose_absorption_34-0" class="reference"><a href="#cite_note-AJCN_fructose_absorption-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> Unabsorbed fructose creates higher <a href="/wiki/Osmolarity" class="mw-redirect" title="Osmolarity">osmolarity</a> in the small intestine, which draws water into the gastrointestinal tract, resulting in osmotic diarrhea. This phenomenon is discussed in greater detail in the <a href="#Potential_health_effects">Health Effects</a> section. </p><p>Table 1 also shows the amount of sucrose found in common fruits and vegetables. <a href="/wiki/Sugarcane" title="Sugarcane">Sugarcane</a> and <a href="/wiki/Sugar_beet" title="Sugar beet">sugar beet</a> have a high concentration of sucrose, and are used for commercial preparation of pure sucrose. Extracted cane or beet juice is clarified, removing impurities; and concentrated by removing excess water. The end product is 99.9%-pure sucrose. Sucrose-containing sugars include common white sugar and <a href="/wiki/Powdered_sugar" title="Powdered sugar">powdered sugar</a>, as well as <a href="/wiki/Brown_sugar" title="Brown sugar">brown sugar</a>.<sup id="cite_ref-Kretchmer_35-0" class="reference"><a href="#cite_note-Kretchmer-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> </p> <table class="wikitable" style="text-align:center; margin:auto"> <caption>Sugar content of selected common plant foods (g/100g)<sup id="cite_ref-www.nal.usda.gov_36-0" class="reference"><a href="#cite_note-www.nal.usda.gov-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup><br /><sup class="noprint Inline-Template" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Cleanup" title="Wikipedia:Cleanup"><span title="Wikipedia:Cleanup">Some of these ratios don't agree</span></a></i>]</sup> </caption> <tbody><tr> <th>Food Item </th> <th>Total<br />carbohydrate<sup class="plainlinks nourlexpansion citation" id="ref_2"><a href="#endnote_2">A</a></sup><br />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>Fructose/<br />glucose<br />ratio </th> <th>Sucrose<br />as a % of<br />total sugars </th> <th>Free fructose<br />as a % of<br />total sugars </th></tr> <tr> <th colspan="9">Fruits </th></tr> <tr> <td><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> <td>57 </td></tr> <tr> <td><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> <td>10 </td></tr> <tr> <td><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> <td>40 </td></tr> <tr> <td><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>1.9 </td> <td>47.8 </td></tr> <tr> <td><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> <td>52 </td></tr> <tr> <td><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> <td>26 </td></tr> <tr> <td><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> <td>18 </td></tr> <tr> <td><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> <td>63 </td></tr> <tr> <td><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> <td>21 </td></tr> <tr> <td><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> <td>31 </td></tr> <tr> <th colspan="9">Vegetables </th></tr> <tr> <td><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> <td>1.5 </td></tr> <tr> <td><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> <td>13 </td></tr> <tr> <td><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> <td>55 </td></tr> <tr> <td><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> <td>40 </td></tr> <tr> <td><a href="/wiki/Sweet_Potato" class="mw-redirect" 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> <td>17 </td></tr> <tr> <td><a href="/wiki/Yam_(vegetable)" title="Yam (vegetable)">Yam</a></td> <td>27.9</td> <td>0.5</td> <td>tr</td> <td>tr</td> <td>tr</td> <td>na</td> <td>tr </td> <td> </td></tr> <tr> <td><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> <td>1.5-5.6 </td></tr> <tr> <td><a href="/wiki/Sugar_Beet" class="mw-redirect" 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> <td>0.59-2.8 </td></tr> <tr> <th colspan="9">Grains </th></tr> <tr> <td><a href="/wiki/Maize" title="Maize">Maize</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> <td>31 </td></tr></tbody></table> <dl><dd><style data-mw-deduplicate="TemplateStyles:r1041539562">.mw-parser-output .citation{word-wrap:break-word}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}</style><span class="citation wikicite" id="endnote_2"><b><a href="#ref_2">^A</a></b></span> The carbohydrate figure is calculated in FoodData Central and does not always correspond to the sum of the sugars, the starch, and the "dietary fiber".</dd></dl> <p>All data with a unit of g (gram) are based on 100 g of a food item. The fructose/glucose ratio is calculated by dividing the sum of free fructose plus half sucrose by the sum of free glucose plus half sucrose. </p><p>Fructose is also found in the manufactured <a href="/wiki/Sugar_substitute" title="Sugar substitute">sweetener</a>, high-fructose corn syrup (HFCS), which is produced by treating <a href="/wiki/Corn_syrup" title="Corn syrup">corn syrup</a> with <a href="/wiki/Enzyme" title="Enzyme">enzymes</a>, converting glucose into fructose.<sup id="cite_ref-fda2014_37-0" class="reference"><a href="#cite_note-fda2014-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup> The common designations for fructose content, HFCS-42 and HFCS-55, indicate the percentage of fructose present in HFCS.<sup id="cite_ref-fda2014_37-1" class="reference"><a href="#cite_note-fda2014-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup> HFCS-55 is commonly used as a sweetener for <a href="/wiki/Soft_drink" title="Soft drink">soft drinks</a>, whereas HFCS-42 is used to sweeten processed foods, <a href="/wiki/Breakfast_cereals" class="mw-redirect" title="Breakfast cereals">breakfast cereals</a>, <a href="/wiki/Bakery" title="Bakery">bakery</a> foods, and some soft drinks.<sup id="cite_ref-fda2014_37-2" class="reference"><a href="#cite_note-fda2014-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Carbohydrate_content_of_commercial_sweeteners_(percent_on_dry_basis)"><span id="Carbohydrate_content_of_commercial_sweeteners_.28percent_on_dry_basis.29"></span>Carbohydrate content of commercial sweeteners (percent on dry basis)</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fructose&action=edit&section=14" title="Edit section: Carbohydrate content of commercial sweeteners (percent on dry basis)"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <table class="wikitable sortable" style="text-align:center; margin:auto"> <tbody><tr> <th>Sugar </th> <th>Fructose </th> <th><a href="/wiki/Glucose" title="Glucose">Glucose</a> </th> <th><a href="/wiki/Sucrose" title="Sucrose">Sucrose</a><br />(Fructose+Glucose) </th> <th>Other<br />sugars </th></tr> <tr> <td>Granulated sugar </td> <td>0 </td> <td>0 </td> <td>100 </td> <td>0 </td></tr> <tr> <td>Caramel </td> <td>1 </td> <td>1 </td> <td>97 </td> <td>1 </td></tr> <tr> <td>HFCS-42 </td> <td>42 </td> <td>53 </td> <td>0 </td> <td>5 </td></tr> <tr> <td>HFCS-55 </td> <td>55 </td> <td>41 </td> <td>0 </td> <td>4 </td></tr> <tr> <td>HFCS-90 </td> <td>90 </td> <td>5 </td> <td>0 </td> <td>5 </td></tr> <tr> <td>Honey </td> <td>50 </td> <td>44 </td> <td>1 </td> <td>5 </td></tr> <tr> <td>Maple syrup </td> <td>1 </td> <td>4 </td> <td>95 </td> <td>0 </td></tr> <tr> <td>Molasses </td> <td>23 </td> <td>21 </td> <td>53 </td> <td>3 </td></tr> <tr> <td>Tapioca Syrup </td> <td>55 </td> <td>45 </td> <td>0 </td> <td>0 </td></tr> <tr> <td>Corn syrup </td> <td>0 </td> <td>98 </td> <td>0 </td> <td>2 </td></tr></tbody></table> <p><sup id="cite_ref-Kretchmer_35-1" class="reference"><a href="#cite_note-Kretchmer-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> for HFCS, and USDA for fruits and vegetables and the other refined sugars.<sup id="cite_ref-www.nal.usda.gov_36-1" class="reference"><a href="#cite_note-www.nal.usda.gov-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup> </p><p>Cane and beet sugars have been used as the major sweetener in food manufacturing for centuries. However, with the development of HFCS, a significant shift occurred in the type of sweetener consumption in certain countries, particularly the United States.<sup id="cite_ref-white_38-0" class="reference"><a href="#cite_note-white-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup> Contrary to the popular belief, however, with the increase of HFCS consumption, the total fructose intake relative to the total glucose intake has not dramatically changed. Granulated sugar is 99.9%-pure sucrose, which means that it has equal ratio of fructose to glucose. The most commonly used forms of HFCS, HFCS-42, and HFCS-55, have a roughly equal ratio of fructose to glucose, with minor differences. HFCS has simply replaced sucrose as a sweetener. Therefore, despite the changes in the sweetener consumption, the ratio of glucose to fructose intake has remained relatively constant.<sup id="cite_ref-39" class="reference"><a href="#cite_note-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:U.s.sugarconsumption.2.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d5/U.s.sugarconsumption.2.svg/400px-U.s.sugarconsumption.2.svg.png" decoding="async" width="400" height="260" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d5/U.s.sugarconsumption.2.svg/600px-U.s.sugarconsumption.2.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d5/U.s.sugarconsumption.2.svg/800px-U.s.sugarconsumption.2.svg.png 2x" data-file-width="512" data-file-height="333" /></a><figcaption><b>Figure 3:</b> Adjusted consumption of refined sugar per capita in the US</figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="Nutritional_information">Nutritional information</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fructose&action=edit&section=15" title="Edit section: Nutritional information"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Providing 368 kcal per 100 grams of dry powder (table), fructose has 95% the <a href="/wiki/Calorie" title="Calorie">caloric value</a> of sucrose by weight.<sup id="cite_ref-usda-fructose_40-0" class="reference"><a href="#cite_note-usda-fructose-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-usda-sucrose_41-0" class="reference"><a href="#cite_note-usda-sucrose-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> Fructose powder is 100% carbohydrates and supplies no other <a href="/wiki/Nutrient" title="Nutrient">nutrients</a> in significant amount (table). </p> <style data-mw-deduplicate="TemplateStyles:r1257001546">.mw-parser-output .infobox-subbox{padding:0;border:none;margin:-3px;width:auto;min-width:100%;font-size:100%;clear:none;float:none;background-color:transparent}.mw-parser-output .infobox-3cols-child{margin:auto}.mw-parser-output .infobox .navbar{font-size:100%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .infobox-full-data:not(.notheme)>div:not(.notheme)[style]{background:#1f1f23!important;color:#f8f9fa}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .infobox-full-data:not(.notheme) div:not(.notheme){background:#1f1f23!important;color:#f8f9fa}}@media(min-width:640px){body.skin--responsive .mw-parser-output .infobox-table{display:table!important}body.skin--responsive .mw-parser-output .infobox-table>caption{display:table-caption!important}body.skin--responsive .mw-parser-output .infobox-table>tbody{display:table-row-group}body.skin--responsive .mw-parser-output .infobox-table tr{display:table-row!important}body.skin--responsive .mw-parser-output .infobox-table th,body.skin--responsive .mw-parser-output .infobox-table td{padding-left:inherit;padding-right:inherit}}</style><table class="infobox nowrap"><caption class="infobox-title" style="white-space:normal; padding-bottom:0.15em;">Fructose, dry powdered</caption><tbody><tr><th colspan="2" class="infobox-header">Nutritional value per 100 g (3.5 oz)</th></tr><tr><th scope="row" class="infobox-label"><a href="/wiki/Food_energy" title="Food energy">Energy</a></th><td class="infobox-data">368 kcal (1,540 kJ)</td></tr><tr><td colspan="2" class="infobox-full-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1257001546"></td></tr><tr><th scope="row" class="infobox-label" style="padding-left:0.65em;line-height:1.1em;font-weight:normal;padding-right:0.25em;"><div style="position:relative;left:-0.65em;"><b><a href="/wiki/Carbohydrate" title="Carbohydrate">Carbohydrates</a></b></div></th><td class="infobox-data" style="vertical-align:middle;padding-left:0.65em;line-height:1.1em;"><div style="position:relative;left:-0.65em;">100 g</div></td></tr><tr style="display:none"><td colspan="2"> </td></tr><tr><td colspan="2" class="infobox-full-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1257001546"></td></tr><tr><th scope="row" class="infobox-label" style="padding-left:0.65em;line-height:1.1em;font-weight:normal;padding-right:0.25em;"><div style="position:relative;left:-0.65em;"><b><a href="/wiki/Fat" title="Fat">Fat</a></b></div></th><td class="infobox-data" style="vertical-align:middle;padding-left:0.65em;line-height:1.1em;"><div style="position:relative;left:-0.65em;">0 g</div></td></tr><tr style="display:none"><td colspan="2"> </td></tr><tr><td colspan="2" class="infobox-full-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1257001546"></td></tr><tr><th scope="row" class="infobox-label" style="padding-left:0.65em;line-height:1.1em;font-weight:normal;padding-right:0.25em;"><div style="position:relative;left:-0.65em;"><b><a href="/wiki/Protein_(nutrient)" title="Protein (nutrient)">Protein</a></b></div></th><td class="infobox-data" style="vertical-align:middle;padding-left:0.65em;line-height:1.1em;"><div style="position:relative;left:-0.65em;">0 g</div></td></tr> <tr><td colspan="2"> <table class="mw-collapsible mw-collapsed" style="; ; width:100%;"> <tbody><tr> <th colspan="2" style="line-height:normal; padding:0.2em; ;"><div style="text-align: center; padding: 0 0.4em; margin: 0 3.3em">Vitamins and minerals</div></th> </tr><tr style="display:none"><td colspan="2"> </td></tr><tr><td colspan="2" class="infobox-full-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1257001546"></td></tr><tr><th scope="row" class="infobox-label" style="padding-left:0.65em;line-height:1.1em;font-weight:normal;padding-right:0.25em;"><b style="margin-left:-0.65em"><a href="/wiki/Mineral_(nutrient)" title="Mineral (nutrient)">Minerals</a></b></th><td class="infobox-data" style="vertical-align:middle;padding-left:0.65em;line-height:1.1em;"><b>Quantity</b> <div style="float: right;"><abbr title="Percentage of Daily Value"><b>%DV</b></abbr><sup>†</sup></div></td></tr><tr><th scope="row" class="infobox-label" style="padding-left:0.65em;line-height:1.1em;font-weight:normal;padding-right:0.25em;"><a href="/wiki/Calcium_in_biology#Humans" title="Calcium in biology">Calcium</a></th><td class="infobox-data" style="vertical-align:middle;padding-left:0.65em;line-height:1.1em;"><div style="float: right;">0%</div> 0 mg</td></tr><tr><th scope="row" class="infobox-label" style="padding-left:0.65em;line-height:1.1em;font-weight:normal;padding-right:0.25em;"><a href="/wiki/Human_iron_metabolism" title="Human iron metabolism">Iron</a></th><td class="infobox-data" style="vertical-align:middle;padding-left:0.65em;line-height:1.1em;"><div style="float: right;">1%</div> 0.1 mg</td></tr><tr><th scope="row" class="infobox-label" style="padding-left:0.65em;line-height:1.1em;font-weight:normal;padding-right:0.25em;"><a href="/wiki/Phosphorus#Biological_role" title="Phosphorus">Phosphorus</a></th><td class="infobox-data" style="vertical-align:middle;padding-left:0.65em;line-height:1.1em;"><div style="float: right;">0%</div> 0 mg</td></tr><tr><th scope="row" class="infobox-label" style="padding-left:0.65em;line-height:1.1em;font-weight:normal;padding-right:0.25em;"><a href="/wiki/Potassium_in_biology" title="Potassium in biology">Potassium</a></th><td class="infobox-data" style="vertical-align:middle;padding-left:0.65em;line-height:1.1em;"><div style="float: right;">0%</div> 0 mg</td></tr><tr><th scope="row" class="infobox-label" style="padding-left:0.65em;line-height:1.1em;font-weight:normal;padding-right:0.25em;"><a href="/wiki/Sodium_in_biology" title="Sodium in biology">Sodium</a></th><td class="infobox-data" style="vertical-align:middle;padding-left:0.65em;line-height:1.1em;"><div style="float: right;">1%</div> 12 mg</td></tr><tr><td colspan="2"> </td></tr></tbody></table></td></tr><tr><td colspan="2" class="infobox-full-data"><hr /><div class="wrap" style="padding:0.3em;line-height:1.2em;"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20170208033356/https://ndb.nal.usda.gov/ndb/foods/show/8681">Full Link to USDA Database entry</a></div></td></tr><tr><td colspan="2" class="infobox-below wrap" style="background:#e0e0e0;padding:0.3em;line-height:1.5em;font-weight:normal;font-size:0.9em"><sup>†</sup>Percentages estimated using <a href="/wiki/Reference_Daily_Intake#Daily_Values" title="Reference Daily Intake">US recommendations</a> for adults,<sup id="cite_ref-FDADailyValues_42-0" class="reference"><a href="#cite_note-FDADailyValues-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup> except for potassium, which is estimated based on expert recommendation from <a href="/wiki/National_Academies_of_Sciences,_Engineering,_and_Medicine" title="National Academies of Sciences, Engineering, and Medicine">the National Academies</a>.<sup id="cite_ref-NationalAcademiesPotassium_43-0" class="reference"><a href="#cite_note-NationalAcademiesPotassium-43"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup></td></tr></tbody></table> <div class="mw-heading mw-heading2"><h2 id="Fructose_digestion_and_absorption_in_humans">Fructose digestion and absorption in humans</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fructose&action=edit&section=16" title="Edit section: Fructose digestion and absorption in humans"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1251242444"><table class="box-More_citations_needed plainlinks metadata ambox ambox-content ambox-Refimprove" role="presentation"><tbody><tr><td class="mbox-image"><div class="mbox-image-div"><span typeof="mw:File"><a href="/wiki/File:Question_book-new.svg" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/9/99/Question_book-new.svg/50px-Question_book-new.svg.png" decoding="async" width="50" height="39" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/9/99/Question_book-new.svg/75px-Question_book-new.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/9/99/Question_book-new.svg/100px-Question_book-new.svg.png 2x" data-file-width="512" data-file-height="399" /></a></span></div></td><td class="mbox-text"><div class="mbox-text-span">This section <b>needs additional citations for <a href="/wiki/Wikipedia:Verifiability" title="Wikipedia:Verifiability">verification</a></b>.<span class="hide-when-compact"> Please help <a href="/wiki/Special:EditPage/Fructose" title="Special:EditPage/Fructose">improve this article</a> by <a href="/wiki/Help:Referencing_for_beginners" title="Help:Referencing for beginners">adding citations to reliable sources</a> in this section. Unsourced material may be challenged and removed.<br /><small><span class="plainlinks"><i>Find sources:</i> <a rel="nofollow" class="external text" href="https://www.google.com/search?as_eq=wikipedia&q=%22Fructose%22">"Fructose"</a> – <a rel="nofollow" class="external text" href="https://www.google.com/search?tbm=nws&q=%22Fructose%22+-wikipedia&tbs=ar:1">news</a> <b>·</b> <a rel="nofollow" class="external text" href="https://www.google.com/search?&q=%22Fructose%22&tbs=bkt:s&tbm=bks">newspapers</a> <b>·</b> <a rel="nofollow" class="external text" href="https://www.google.com/search?tbs=bks:1&q=%22Fructose%22+-wikipedia">books</a> <b>·</b> <a rel="nofollow" class="external text" href="https://scholar.google.com/scholar?q=%22Fructose%22">scholar</a> <b>·</b> <a rel="nofollow" class="external text" href="https://www.jstor.org/action/doBasicSearch?Query=%22Fructose%22&acc=on&wc=on">JSTOR</a></span></small></span> <span class="date-container"><i>(<span class="date">May 2020</span>)</i></span><span class="hide-when-compact"><i> (<small><a href="/wiki/Help:Maintenance_template_removal" title="Help:Maintenance template removal">Learn how and when to remove this message</a></small>)</i></span></div></td></tr></tbody></table> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Sucrase.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/07/Sucrase.svg/300px-Sucrase.svg.png" decoding="async" width="300" height="170" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/07/Sucrase.svg/450px-Sucrase.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/07/Sucrase.svg/600px-Sucrase.svg.png 2x" data-file-width="1658" data-file-height="939" /></a><figcaption><b>Figure 4:</b> Hydrolysis of sucrose to glucose and fructose by sucrase</figcaption></figure> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Fructosetransporter.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e9/Fructosetransporter.svg/300px-Fructosetransporter.svg.png" decoding="async" width="300" height="180" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e9/Fructosetransporter.svg/450px-Fructosetransporter.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e9/Fructosetransporter.svg/600px-Fructosetransporter.svg.png 2x" data-file-width="512" data-file-height="307" /></a><figcaption><b>Figure 5:</b> Intestinal sugar transport proteins</figcaption></figure> <p>Fructose exists in foods either as a monosaccharide (free fructose) or as a unit of a disaccharide (sucrose). Free fructose is a ketonic simple sugar and one of the three dietary monosaccharides absorbed directly by the intestine. When fructose is consumed in the form of sucrose, it is digested (broken down) and then absorbed as free fructose. As sucrose comes into contact with the membrane of the small intestine, the enzyme <a href="/wiki/Sucrase" title="Sucrase">sucrase</a> catalyzes the cleavage of sucrose to yield one glucose unit and one fructose unit, which are then each absorbed. After absorption, it enters the <a href="/wiki/Hepatic_portal_vein" class="mw-redirect" title="Hepatic portal vein">hepatic portal vein</a> and is directed toward the liver. </p><p>The mechanism of fructose absorption in the small intestine is not completely understood. Some evidence suggests <a href="/wiki/Active_transport" title="Active transport">active transport</a>, because fructose uptake has been shown to occur against a concentration gradient.<sup id="cite_ref-44" class="reference"><a href="#cite_note-44"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup> However, the majority of research supports the claim that fructose absorption occurs on the mucosal membrane via <a href="/wiki/Facilitated_diffusion" title="Facilitated diffusion">facilitated transport</a> involving <a href="/wiki/GLUT5" title="GLUT5">GLUT5</a> transport proteins.<sup id="cite_ref-Shi_45-0" class="reference"><a href="#cite_note-Shi-45"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup> Since the concentration of fructose is higher in the lumen, fructose is able to flow down a concentration gradient into the <a href="/wiki/Enterocytes" class="mw-redirect" title="Enterocytes">enterocytes</a>, assisted by transport proteins. Fructose may be transported out of the enterocyte across the basolateral membrane by either <a href="/wiki/GLUT2" title="GLUT2">GLUT2</a> or GLUT5, although the GLUT2 transporter has a greater capacity for transporting fructose, and, therefore, the majority of fructose is transported out of the enterocyte through GLUT2.<sup id="cite_ref-Shi_45-1" class="reference"><a href="#cite_note-Shi-45"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Capacity_and_rate_of_absorption">Capacity and rate of absorption</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fructose&action=edit&section=17" title="Edit section: Capacity and rate of absorption"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The absorption capacity for fructose in monosaccharide form ranges from less than 5 g to 50 g (per individual serving) and adapts with changes in dietary fructose intake.<sup id="cite_ref-fuji_46-0" class="reference"><a href="#cite_note-fuji-46"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup> Studies show the greatest absorption rate occurs when glucose and fructose are administered in equal quantities.<sup id="cite_ref-fuji_46-1" class="reference"><a href="#cite_note-fuji-46"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup> When fructose is ingested as part of the disaccharide sucrose, absorption capacity is much higher because fructose exists in a 1:1 ratio with glucose. It appears that the <a href="/wiki/GLUT5" title="GLUT5">GLUT5</a> transfer rate may be saturated at low levels, and absorption is increased through joint absorption with glucose.<sup id="cite_ref-47" class="reference"><a href="#cite_note-47"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup> One proposed mechanism for this phenomenon is a glucose-dependent <a href="/wiki/Cotransport" class="mw-redirect" title="Cotransport">cotransport</a> of fructose. In addition, fructose transfer activity increases with dietary fructose intake. The presence of fructose in the lumen causes increased mRNA transcription of GLUT5, leading to increased transport proteins. High-fructose diets (>2.4 g/kg body wt) increase the transport proteins within three days of intake.<sup id="cite_ref-48" class="reference"><a href="#cite_note-48"><span class="cite-bracket">[</span>48<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Malabsorption">Malabsorption</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fructose&action=edit&section=18" title="Edit section: Malabsorption"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></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/Fructose_malabsorption" title="Fructose malabsorption">Fructose malabsorption</a></div> <p>Several studies have measured the intestinal absorption of fructose using the <a href="/wiki/Hydrogen_breath_test" title="Hydrogen breath test">hydrogen breath test</a>.<sup id="cite_ref-Beyer_49-0" class="reference"><a href="#cite_note-Beyer-49"><span class="cite-bracket">[</span>49<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-50" class="reference"><a href="#cite_note-50"><span class="cite-bracket">[</span>50<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-51" class="reference"><a href="#cite_note-51"><span class="cite-bracket">[</span>51<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-52" class="reference"><a href="#cite_note-52"><span class="cite-bracket">[</span>52<span class="cite-bracket">]</span></a></sup> These studies indicate that fructose is not completely absorbed in the small intestine. When fructose is not absorbed in the small intestine, it is transported into the large intestine, where it is fermented by the colonic flora. Hydrogen is produced during the <a href="/wiki/Fermentation_(biochemistry)" class="mw-redirect" title="Fermentation (biochemistry)">fermentation</a> process and dissolves into the blood of the <a href="/wiki/Portal_vein" title="Portal vein">portal vein</a>. This hydrogen is transported to the lungs, where it is exchanged across the lungs and is measurable by the hydrogen breath test. The colonic flora also produces carbon dioxide, <a href="/wiki/Short-chain_fatty_acid" title="Short-chain fatty acid">short-chain fatty acids</a>, organic acids, and trace gases in the presence of unabsorbed fructose.<sup id="cite_ref-53" class="reference"><a href="#cite_note-53"><span class="cite-bracket">[</span>53<span class="cite-bracket">]</span></a></sup> The presence of gases and organic acids in the large intestine causes gastrointestinal symptoms such as bloating, diarrhea, flatulence, and gastrointestinal pain.<sup id="cite_ref-Beyer_49-1" class="reference"><a href="#cite_note-Beyer-49"><span class="cite-bracket">[</span>49<span class="cite-bracket">]</span></a></sup> Exercise immediately after consumption can exacerbate these symptoms by decreasing transit time in the small intestine, resulting in a greater amount of fructose emptied into the large intestine.<sup id="cite_ref-54" class="reference"><a href="#cite_note-54"><span class="cite-bracket">[</span>54<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Fructose_metabolism">Fructose metabolism</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fructose&action=edit&section=19" title="Edit section: Fructose metabolism"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>All three dietary monosaccharides are transported into the liver by the GLUT2 transporter.<sup id="cite_ref-55" class="reference"><a href="#cite_note-55"><span class="cite-bracket">[</span>55<span class="cite-bracket">]</span></a></sup> Fructose and <a href="/wiki/Galactose" title="Galactose">galactose</a> are <a href="/wiki/Phosphorylation" title="Phosphorylation">phosphorylated</a> in the liver by <a href="/wiki/Fructokinase" title="Fructokinase">fructokinase</a> (<a href="/wiki/Michaelis%E2%80%93Menten_kinetics" title="Michaelis–Menten kinetics">K<sub>m</sub></a>= 0.5 mM) and <a href="/wiki/Galactokinase" title="Galactokinase">galactokinase</a> (K<sub>m</sub> = 0.8 mM), respectively. By contrast, glucose tends to pass through the liver (K<sub>m</sub> of hepatic glucokinase = 10 mM) and can be metabolised anywhere in the body. Uptake of fructose by the liver is not regulated by insulin. However, insulin is capable of increasing the abundance and functional activity of GLUT5, fructose transporter, in skeletal muscle cells.<sup id="cite_ref-56" class="reference"><a href="#cite_note-56"><span class="cite-bracket">[</span>56<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Fructolysis">Fructolysis</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fructose&action=edit&section=20" title="Edit section: Fructolysis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></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/Fructolysis" title="Fructolysis">Fructolysis</a></div> <p>The initial <a href="/wiki/Catabolism" title="Catabolism">catabolism</a> of fructose is sometimes referred to as <a href="/wiki/Fructolysis" title="Fructolysis">fructolysis</a>, in analogy with <a href="/wiki/Glycolysis" title="Glycolysis">glycolysis</a>, the catabolism of glucose. In fructolysis, the enzyme <a href="/wiki/Fructokinase" title="Fructokinase">fructokinase</a> initially produces <a href="/wiki/Fructose_1-phosphate" title="Fructose 1-phosphate">fructose 1-phosphate</a>, which is split by <a href="/wiki/Aldolase_B" title="Aldolase B">aldolase B</a> to produce the <a href="/wiki/Triose" title="Triose">trioses</a> <a href="/wiki/Dihydroxyacetone_phosphate" title="Dihydroxyacetone phosphate">dihydroxyacetone phosphate</a> (DHAP) and <a href="/wiki/Glyceraldehyde" title="Glyceraldehyde">glyceraldehyde</a>. Unlike glycolysis, in fructolysis the triose <a href="/wiki/Glyceraldehyde" title="Glyceraldehyde">glyceraldehyde</a> lacks a <a href="/wiki/Phosphate_group" class="mw-redirect" title="Phosphate group">phosphate group</a>. A third enzyme, <a href="/wiki/Triokinase" title="Triokinase">triokinase</a>, is therefore required to phosphorylate glyceraldehyde, producing <a href="/wiki/Glyceraldehyde_3-phosphate" title="Glyceraldehyde 3-phosphate">glyceraldehyde 3-phosphate</a>. The resulting trioses are identical to those obtained in glycolysis and can enter the <a href="/wiki/Gluconeogenesis" title="Gluconeogenesis">gluconeogenic</a> pathway for glucose or glycogen synthesis, or be further catabolized through the lower glycolytic pathway to <a href="/wiki/Pyruvic_acid" title="Pyruvic acid">pyruvate</a>. </p> <div class="mw-heading mw-heading3"><h3 id="Metabolism_of_fructose_to_DHAP_and_glyceraldehyde">Metabolism of fructose to DHAP and glyceraldehyde</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fructose&action=edit&section=21" title="Edit section: Metabolism of fructose to DHAP and glyceraldehyde"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The first step in the metabolism of fructose is the phosphorylation of fructose to fructose 1-phosphate by fructokinase, thus trapping fructose for metabolism in the liver. Fructose 1-phosphate then undergoes <a href="/wiki/Hydrolysis" title="Hydrolysis">hydrolysis</a> by <a href="/wiki/Aldolase_B" title="Aldolase B">aldolase B</a> to form DHAP and glyceraldehydes; DHAP can either be <a href="/wiki/Isomerization" title="Isomerization">isomerized</a> to glyceraldehyde 3-phosphate by triosephosphate isomerase or undergo reduction to glycerol 3-phosphate by glycerol 3-phosphate dehydrogenase. The glyceraldehyde produced may also be converted to glyceraldehyde 3-phosphate by glyceraldehyde kinase or further converted to glycerol 3-phosphate by glycerol 3-phosphate dehydrogenase. The metabolism of fructose at this point yields intermediates in the gluconeogenic pathway leading to glycogen synthesis as well as fatty acid and triglyceride synthesis. </p> <div class="mw-heading mw-heading3"><h3 id="Synthesis_of_glycogen_from_DHAP_and_glyceraldehyde_3-phosphate">Synthesis of glycogen from DHAP and glyceraldehyde 3-phosphate</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fructose&action=edit&section=22" title="Edit section: Synthesis of glycogen from DHAP and glyceraldehyde 3-phosphate"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The resultant glyceraldehyde formed by aldolase B then undergoes phosphorylation to glyceraldehyde 3-phosphate. Increased concentrations of DHAP and glyceraldehyde 3-phosphate in the liver drive the gluconeogenic pathway toward glucose and subsequent glycogen synthesis.<sup id="cite_ref-57" class="reference"><a href="#cite_note-57"><span class="cite-bracket">[</span>57<span class="cite-bracket">]</span></a></sup> It appears that fructose is a better substrate for glycogen synthesis than glucose and that glycogen replenishment takes precedence over triglyceride formation.<sup id="cite_ref-58" class="reference"><a href="#cite_note-58"><span class="cite-bracket">[</span>58<span class="cite-bracket">]</span></a></sup> Once liver glycogen is replenished, the intermediates of fructose metabolism are primarily directed toward triglyceride synthesis.<sup id="cite_ref-59" class="reference"><a href="#cite_note-59"><span class="cite-bracket">[</span>59<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Fructose-glycogen.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/30/Fructose-glycogen.svg/400px-Fructose-glycogen.svg.png" decoding="async" width="400" height="297" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/30/Fructose-glycogen.svg/600px-Fructose-glycogen.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/30/Fructose-glycogen.svg/800px-Fructose-glycogen.svg.png 2x" data-file-width="795" data-file-height="591" /></a><figcaption><b>Figure 6:</b> Metabolic conversion of fructose to glycogen in the liver</figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="Synthesis_of_triglyceride_from_DHAP_and_glyceraldehyde_3-phosphate">Synthesis of triglyceride from DHAP and glyceraldehyde 3-phosphate</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fructose&action=edit&section=23" title="Edit section: Synthesis of triglyceride from DHAP and glyceraldehyde 3-phosphate"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Carbons from dietary fructose are found in both the <a href="/wiki/Free_fatty_acid" class="mw-redirect" title="Free fatty acid">free fatty acid</a> and glycerol <a href="/wiki/Moiety_(chemistry)" title="Moiety (chemistry)">moieties</a> of plasma triglycerides. High fructose consumption can lead to excess <a href="/wiki/Pyruvate" class="mw-redirect" title="Pyruvate">pyruvate</a> production, causing a buildup of <a href="/wiki/Krebs_cycle" class="mw-redirect" title="Krebs cycle">Krebs cycle</a> intermediates.<sup id="cite_ref-McGrane_60-0" class="reference"><a href="#cite_note-McGrane-60"><span class="cite-bracket">[</span>60<span class="cite-bracket">]</span></a></sup> Accumulated citrate can be transported from the <a href="/wiki/Mitochondrion" title="Mitochondrion">mitochondria</a> into the <a href="/wiki/Cytosol" title="Cytosol">cytosol</a> of <a href="/wiki/Hepatocytes" class="mw-redirect" title="Hepatocytes">hepatocytes</a>, converted to <a href="/wiki/Acetyl_CoA" class="mw-redirect" title="Acetyl CoA">acetyl CoA</a> by citrate lyase and directed toward fatty acid synthesis.<sup id="cite_ref-McGrane_60-1" class="reference"><a href="#cite_note-McGrane-60"><span class="cite-bracket">[</span>60<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Sul_61-0" class="reference"><a href="#cite_note-Sul-61"><span class="cite-bracket">[</span>61<span class="cite-bracket">]</span></a></sup> In addition, DHAP can be converted to glycerol 3-phosphate, providing the glycerol backbone for the triglyceride molecule.<sup id="cite_ref-Sul_61-1" class="reference"><a href="#cite_note-Sul-61"><span class="cite-bracket">[</span>61<span class="cite-bracket">]</span></a></sup> Triglycerides are incorporated into <a href="/wiki/Very-low-density_lipoprotein" class="mw-redirect" title="Very-low-density lipoprotein">very-low-density lipoproteins</a> (VLDL), which are released from the liver destined toward peripheral tissues for storage in both fat and muscle cells. </p> <figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Fructose-triglyceride.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b0/Fructose-triglyceride.svg/400px-Fructose-triglyceride.svg.png" decoding="async" width="400" height="324" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b0/Fructose-triglyceride.svg/600px-Fructose-triglyceride.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b0/Fructose-triglyceride.svg/800px-Fructose-triglyceride.svg.png 2x" data-file-width="795" data-file-height="644" /></a><figcaption><b>Figure 7:</b> Metabolic conversion of fructose to triglyceride in the liver</figcaption></figure> <div class="mw-heading mw-heading2"><h2 id="Potential_health_effects">Potential health effects</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fructose&action=edit&section=24" title="Edit section: Potential health effects"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In 2022, the European Food Safety Authority stated that there is research evidence that fructose and other added free sugars may be associated with increased risk of several chronic diseases:<sup id="cite_ref-efsa11_12-2" class="reference"><a href="#cite_note-efsa11-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-efsa2-22_13-1" class="reference"><a href="#cite_note-efsa2-22-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> the risk is moderate for obesity and <a href="/wiki/Dyslipidemia" title="Dyslipidemia">dyslipidemia</a> (more than 50%), and low for <a href="/wiki/Non-alcoholic_fatty_liver_disease" class="mw-redirect" title="Non-alcoholic fatty liver disease">non-alcoholic fatty liver disease</a>, <a href="/wiki/Type_2_diabetes" title="Type 2 diabetes">type 2 diabetes</a> (from 15% to 50%) and <a href="/wiki/Hypertension" title="Hypertension">hypertension</a>. EFSA further stated that clinical research did "not support a positive relationship between the intake of dietary sugars, in isocaloric exchange with other macronutrients, and any of the chronic metabolic diseases or pregnancy-related endpoints assessed" but advised "the intake of added and free sugars should be as low as possible in the context of a nutritionally adequate diet."<sup id="cite_ref-efsa2-22_13-2" class="reference"><a href="#cite_note-efsa2-22-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Cardiometabolic_diseases">Cardiometabolic diseases</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fructose&action=edit&section=25" title="Edit section: Cardiometabolic diseases"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>When fructose is consumed in excess as a sweetening agent in foods or beverages, it may be associated with increased risk of obesity, diabetes, and cardiovascular disorders that are part of <a href="/wiki/Metabolic_syndrome" title="Metabolic syndrome">metabolic syndrome</a>.<sup id="cite_ref-efsa2-22_13-3" class="reference"><a href="#cite_note-efsa2-22-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Compared_with_sucrose">Compared with sucrose</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fructose&action=edit&section=26" title="Edit section: Compared with sucrose"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Fructose was found to increase <a href="/wiki/Triglyceride" title="Triglyceride">triglycerides</a> in type-2 but not type-1 diabetes and moderate use of it has previously been considered acceptable as a sweetener for diabetics,<sup id="cite_ref-Rizkalla_62-0" class="reference"><a href="#cite_note-Rizkalla-62"><span class="cite-bracket">[</span>62<span class="cite-bracket">]</span></a></sup> possibly because it does not trigger the production of insulin by pancreatic <a href="/wiki/Beta_cell" title="Beta cell">β cells</a>.<sup id="cite_ref-Thorens_63-0" class="reference"><a href="#cite_note-Thorens-63"><span class="cite-bracket">[</span>63<span class="cite-bracket">]</span></a></sup> For a 50 gram reference amount, fructose has a <a href="/wiki/Glycemic_index" title="Glycemic index">glycemic index</a> of 23, compared with 100 for glucose and 60 for sucrose.<sup id="cite_ref-gitr_64-0" class="reference"><a href="#cite_note-gitr-64"><span class="cite-bracket">[</span>64<span class="cite-bracket">]</span></a></sup> Fructose is also 73% <a href="#Sweetness_of_fructose">sweeter</a> than sucrose at room temperature, allowing diabetics to use less of it per serving. Fructose consumed before a meal may reduce the glycemic response of the meal.<sup id="cite_ref-:0_65-0" class="reference"><a href="#cite_note-:0-65"><span class="cite-bracket">[</span>65<span class="cite-bracket">]</span></a></sup> Fructose-sweetened food and beverage products cause less of a rise in blood glucose levels than do those manufactured with either sucrose or glucose.<sup id="cite_ref-efsa11_12-3" class="reference"><a href="#cite_note-efsa11-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fructose&action=edit&section=27" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Hereditary_fructose_intolerance" title="Hereditary fructose intolerance">Hereditary fructose intolerance</a></li> <li><a href="/wiki/Inverted_sugar_syrup" title="Inverted sugar syrup">Inverted sugar syrup</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fructose&action=edit&section=28" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></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 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"><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="https://web.archive.org/web/20110419073934/http://mw4.m-w.com/dictionary/fructose">"Fructose"</a>. <i>m-w.com</i>. Merriam-Webster. Archived from <a rel="nofollow" class="external text" href="http://mw4.m-w.com/dictionary/fructose">the original</a> on 19 April 2011<span class="reference-accessdate">. Retrieved <span class="nowrap">10 December</span> 2014</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=m-w.com&rft.atitle=Fructose&rft_id=http%3A%2F%2Fmw4.m-w.com%2Fdictionary%2Ffructose&rfr_id=info%3Asid%2Fen.wikipedia.org%3AFructose" class="Z3988"></span></span> </li> <li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text">Levulose comes from the Latin word <i>laevus</i>, "left"; levulose is the old word for the most occurring <a href="/wiki/Isomer" title="Isomer">isomer</a> of fructose. D-fructose rotates plane-polarised light to the left, hence the name.<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.monashscientific.com.au/Levulose.htm">"Levulose"</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20091008032809/http://www.monashscientific.com.au/Levulose.htm">Archived</a> from the original on 2009-10-08<span class="reference-accessdate">. Retrieved <span class="nowrap">2010-01-28</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Levulose&rft_id=http%3A%2F%2Fwww.monashscientific.com.au%2FLevulose.htm&rfr_id=info%3Asid%2Fen.wikipedia.org%3AFructose" 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 class="citation web cs1"><a rel="nofollow" class="external text" href="https://iupac.qmul.ac.uk/2carb/10.html">"2-Carb-10"</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20230618145008/https://iupac.qmul.ac.uk/2carb/10.html">Archived</a> from the original on 2023-06-18<span class="reference-accessdate">. Retrieved <span class="nowrap">2023-06-18</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=2-Carb-10&rft_id=https%3A%2F%2Fiupac.qmul.ac.uk%2F2carb%2F10.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AFructose" class="Z3988"></span></span> </li> <li id="cite_note-CRC-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-CRC_4-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation book cs1 cs1-prop-year-range-abbreviated"><i><a href="/wiki/CRC_Handbook_of_Chemistry_and_Physics" title="CRC Handbook of Chemistry and Physics">CRC Handbook of Chemistry and Physics</a></i> (49th ed.). 1968–69. p. D-186.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=CRC+Handbook+of+Chemistry+and+Physics&rft.pages=D-186&rft.edition=49th&rft.date=1968%2F1969&rfr_id=info%3Asid%2Fen.wikipedia.org%3AFructose" class="Z3988"></span></span> </li> <li id="cite_note-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-5">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFChambers" class="citation web cs1">Chambers, Michael. <a rel="nofollow" class="external text" href="https://chem.nlm.nih.gov/chemidplus/rn/57-48-7">"ChemIDplus – 57-48-7 – BJHIKXHVCXFQLS-UYFOZJQFSA-N – Fructose [USP:JAN] – Similar structures search, synonyms, formulas, resource links, and other chemical information"</a>. <i>chem.sis.nlm.nih.gov</i>. US National Institutes of Health. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20141210194215/https://chem.nlm.nih.gov/chemidplus/rn/57-48-7">Archived</a> from the original on 10 December 2014<span class="reference-accessdate">. Retrieved <span class="nowrap">10 December</span> 2014</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=chem.sis.nlm.nih.gov&rft.atitle=ChemIDplus+%E2%80%93+57-48-7+%E2%80%93+BJHIKXHVCXFQLS-UYFOZJQFSA-N+%E2%80%93+Fructose+%5BUSP%3AJAN%5D+%E2%80%93+Similar+structures+search%2C+synonyms%2C+formulas%2C+resource+links%2C+and+other+chemical+information.&rft.aulast=Chambers&rft.aufirst=Michael&rft_id=https%3A%2F%2Fchem.nlm.nih.gov%2Fchemidplus%2Frn%2F57-48-7&rfr_id=info%3Asid%2Fen.wikipedia.org%3AFructose" 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"><a rel="nofollow" class="external free" href="https://diabetesjournals.org/care/article/25/2/353/23338/Increased-Fructose-Concentrations-in-Blood-and">https://diabetesjournals.org/care/article/25/2/353/23338/Increased-Fructose-Concentrations-in-Blood-and</a></span> </li> <li id="cite_note-7"><span class="mw-cite-backlink"><b><a href="#cite_ref-7">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFDubrunfaut1847" class="citation journal cs1 cs1-prop-foreign-lang-source">Dubrunfaut (1847). <a rel="nofollow" class="external text" href="https://web.archive.org/web/20140627013828/http://books.google.com/books?id=PJ45AAAAcAAJ&pg=PA169">"Sur une propriété analytique des fermentations alcoolique et lactique, et sur leur application à l'étude des sucres"</a> [On an analytic property of alcoholic and lactic fermentations, and on their application to the study of sugars]. <i>Annales de Chimie et de Physique</i> (in French). <b>21</b>: 169–178. Archived from <a rel="nofollow" class="external text" href="https://books.google.com/books?id=PJ45AAAAcAAJ&pg=PA169">the original</a> on 2014-06-27.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Annales+de+Chimie+et+de+Physique&rft.atitle=Sur+une+propri%C3%A9t%C3%A9+analytique+des+fermentations+alcoolique+et+lactique%2C+et+sur+leur+application+%C3%A0+l%27%C3%A9tude+des+sucres&rft.volume=21&rft.pages=169-178&rft.date=1847&rft.au=Dubrunfaut&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DPJ45AAAAcAAJ%26pg%3DPA169&rfr_id=info%3Asid%2Fen.wikipedia.org%3AFructose" class="Z3988"></span> On page 174, Dubrunfaut relates the discovery and properties of fructose.</span> </li> <li id="cite_note-8"><span class="mw-cite-backlink"><b><a href="#cite_ref-8">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFruton1974" class="citation journal cs1">Fruton, J. 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Retrieved <span class="nowrap">2021-02-05</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Molecular+Nutrition+%26+Food+Research&rft.atitle=Molecules+and+Life+%E2%80%93+Historical+Essays+on+the+Interplay+of+Chemistry+and+Biology&rft.volume=18&rft.issue=4&rft.date=1974&rft_id=info%3Adoi%2F10.1002%2Ffood.19740180423&rft.aulast=Fruton&rft.aufirst=J.+S.&rft_id=https%3A%2F%2Fonlinelibrary.wiley.com%2Fdoi%2Fabs%2F10.1002%2Ffood.19740180423&rfr_id=info%3Asid%2Fen.wikipedia.org%3AFructose" class="Z3988"></span></span> </li> <li id="cite_note-Miller-9"><span class="mw-cite-backlink">^ <a href="#cite_ref-Miller_9-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Miller_9-1"><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="CITEREFMiller1857" class="citation book cs1">Miller, William Allen (1857). 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EFSA Panel on Dietetic Products, Nutrition and Allergies: 2223. 2011. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.2903%2Fj.efsa.2011.2223">10.2903/j.efsa.2011.2223</a></span>. <q>The Panel notes that these values support a significant decrease in post-prandial blood glucose responses when fructose replaces either sucrose or glucose.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=EFSA+Journal&rft.atitle=Scientific+Opinion+on+the+substantiation+of+health+claims+related+to+fructose+and+reduction+of+post-prandial+glycaemic+responses+%28ID+558%29+pursuant+to+Article+13%281%29+of+Regulation+%28EC%29+No+1924%2F2006&rft.volume=9&rft.issue=6&rft.pages=2223&rft.date=2011&rft_id=info%3Adoi%2F10.2903%2Fj.efsa.2011.2223&rft_id=https%3A%2F%2Fdoi.org%2F10.2903%252Fj.efsa.2011.2223&rfr_id=info%3Asid%2Fen.wikipedia.org%3AFructose" class="Z3988"></span></span> </li> <li id="cite_note-efsa2-22-13"><span class="mw-cite-backlink">^ <a href="#cite_ref-efsa2-22_13-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-efsa2-22_13-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-efsa2-22_13-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-efsa2-22_13-3"><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 id="CITEREFEFSA_Panel_on_Nutrition,_Novel_Foods_and_Food_Allergens2022" class="citation journal cs1">EFSA Panel on Nutrition, Novel Foods and Food Allergens (28 February 2022). <a rel="nofollow" class="external text" href="https://doi.org/10.2903/j.efsa.2022.7074">"Tolerable upper intake level for dietary sugars"</a>. <i>EFSA Journal</i>. <b>20</b> (2): 337. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.2903%2Fj.efsa.2022.7074">10.2903/j.efsa.2022.7074</a>. <a href="/wiki/Hdl_(identifier)" class="mw-redirect" title="Hdl (identifier)">hdl</a>:<a rel="nofollow" class="external text" href="https://hdl.handle.net/1854%2FLU-01GWHCPEH24E9RRDYANKYH53MJ">1854/LU-01GWHCPEH24E9RRDYANKYH53MJ</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/1831-4732">1831-4732</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8884083">8884083</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/35251356">35251356</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:247184182">247184182</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20231026085708/https://efsa.onlinelibrary.wiley.com/doi/full/10.2903/j.efsa.2022.7074">Archived</a> from the original on 26 October 2023<span class="reference-accessdate">. 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Upper Saddle River, NJ : Prentice Hall. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-13-021282-5" title="Special:BookSources/978-0-13-021282-5"><bdi>978-0-13-021282-5</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Foods%3A+Experimental+Perspectives%2C+4th+Edition&rft.pub=Upper+Saddle+River%2C+NJ+%3A+Prentice+Hall&rft.date=2001&rft.isbn=978-0-13-021282-5&rft.aulast=McWilliams&rft.aufirst=Margaret&rft_id=https%3A%2F%2Farchive.org%2Fdetails%2Ffoodsexperimenta00mcwi&rfr_id=info%3Asid%2Fen.wikipedia.org%3AFructose" class="Z3988"></span></span> </li> <li id="cite_note-31"><span class="mw-cite-backlink"><b><a href="#cite_ref-31">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWhiteLauer_GN1990" class="citation journal cs1">White, DC; Lauer GN (1990). 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Wittenberg (2007). <span class="id-lock-registration" title="Free registration required"><a rel="nofollow" class="external text" href="https://archive.org/details/isbn_9781580087506"><i>New Good Food: Essential Ingredients for Cooking and Eating Well. Diet and Nutrition Series; pages 249–51</i></a></span>. Ten Speed Press. p. <a rel="nofollow" class="external text" href="https://archive.org/details/isbn_9781580087506/page/249">249</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1580087506" title="Special:BookSources/978-1580087506"><bdi>978-1580087506</bdi></a>. <q>fructose traditional baking.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=New+Good+Food%3A+Essential+Ingredients+for+Cooking+and+Eating+Well.+Diet+and+Nutrition+Series%3B+pages+249%E2%80%9351&rft.pages=249&rft.pub=Ten+Speed+Press&rft.date=2007&rft.isbn=978-1580087506&rft.au=Margaret+M.+Wittenberg&rft_id=https%3A%2F%2Farchive.org%2Fdetails%2Fisbn_9781580087506&rfr_id=info%3Asid%2Fen.wikipedia.org%3AFructose" class="Z3988"></span></span> </li> <li id="cite_note-33"><span class="mw-cite-backlink"><b><a href="#cite_ref-33">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFParkYetley_AE1993" class="citation journal cs1">Park, KY; Yetley AE (1993). <a rel="nofollow" class="external text" href="https://doi.org/10.1093%2Fajcn%2F58.5.737S">"Intakes and food sources of fructose in the United States"</a>. <i>American Journal of Clinical Nutrition</i>. <b>58</b> (5 Suppl): 737S–747S. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1093%2Fajcn%2F58.5.737S">10.1093/ajcn/58.5.737S</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/8213605">8213605</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=American+Journal+of+Clinical+Nutrition&rft.atitle=Intakes+and+food+sources+of+fructose+in+the+United+States&rft.volume=58&rft.issue=5+Suppl&rft.pages=737S-747S&rft.date=1993&rft_id=info%3Adoi%2F10.1093%2Fajcn%2F58.5.737S&rft_id=info%3Apmid%2F8213605&rft.aulast=Park&rft.aufirst=KY&rft.au=Yetley+AE&rft_id=https%3A%2F%2Fdoi.org%2F10.1093%252Fajcn%252F58.5.737S&rfr_id=info%3Asid%2Fen.wikipedia.org%3AFructose" class="Z3988"></span></span> </li> <li id="cite_note-AJCN_fructose_absorption-34"><span class="mw-cite-backlink"><b><a href="#cite_ref-AJCN_fructose_absorption_34-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRibyFujisawa_TKretchmer_N1993" class="citation journal cs1">Riby, JE; Fujisawa T; Kretchmer N (1993). <a rel="nofollow" class="external text" href="https://doi.org/10.1093%2Fajcn%2F58.5.748S">"Fructose absorption"</a>. <i>American Journal of Clinical Nutrition</i>. <b>58</b> (5 Suppl): 748S–753S. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1093%2Fajcn%2F58.5.748S">10.1093/ajcn/58.5.748S</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/8213606">8213606</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=American+Journal+of+Clinical+Nutrition&rft.atitle=Fructose+absorption&rft.volume=58&rft.issue=5+Suppl&rft.pages=748S-753S&rft.date=1993&rft_id=info%3Adoi%2F10.1093%2Fajcn%2F58.5.748S&rft_id=info%3Apmid%2F8213606&rft.aulast=Riby&rft.aufirst=JE&rft.au=Fujisawa+T&rft.au=Kretchmer+N&rft_id=https%3A%2F%2Fdoi.org%2F10.1093%252Fajcn%252F58.5.748S&rfr_id=info%3Asid%2Fen.wikipedia.org%3AFructose" class="Z3988"></span></span> </li> <li id="cite_note-Kretchmer-35"><span class="mw-cite-backlink">^ <a href="#cite_ref-Kretchmer_35-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Kretchmer_35-1"><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="CITEREFKretchmerHollenbeck_CB1991" class="citation book cs1">Kretchmer, N; Hollenbeck CB (1991). <i>Sugars and Sweeteners</i>. 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USDA National Nutrient Database, version SR-28. May 2016. 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USDA National Nutrient Database, version SR-28. May 2016. 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Endocrinology and Metabolism</i>. <b>298</b> (2): E141–E145. <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.00712.2009">10.1152/ajpendo.00712.2009</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0193-1849">0193-1849</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2822486">2822486</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/20009031">20009031</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=American+Journal+of+Physiology.+Endocrinology+and+Metabolism&rft.atitle=Glucose+transporters+in+the+21st+Century+%28Review%29&rft.volume=298&rft.issue=2&rft.pages=E141-E145&rft.date=2010&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC2822486%23id-name%3DPMC&rft.issn=0193-1849&rft_id=info%3Apmid%2F20009031&rft_id=info%3Adoi%2F10.1152%2Fajpendo.00712.2009&rft.aulast=Thorens&rft.aufirst=Bernard&rft.au=Mueckler%2C+Mike&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC2822486&rfr_id=info%3Asid%2Fen.wikipedia.org%3AFructose" class="Z3988"></span></span> </li> <li id="cite_note-gitr-64"><span class="mw-cite-backlink"><b><a href="#cite_ref-gitr_64-0">^</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="http://www.glycemicindex.com/foodSearch.php">"Glycemic index"</a>. Glycemic Index Testing and Research, University of Sydney (Australia) Glycemic Index Research Service (SUGiRS). 2 May 2017. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20210116021928/https://glycemicindex.com/foodSearch.php">Archived</a> from the original on 16 January 2021<span class="reference-accessdate">. Retrieved <span class="nowrap">23 February</span> 2018</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Glycemic+index&rft.pub=Glycemic+Index+Testing+and+Research%2C+University+of+Sydney+%28Australia%29+Glycemic+Index+Research+Service+%28SUGiRS%29&rft.date=2017-05-02&rft_id=http%3A%2F%2Fwww.glycemicindex.com%2FfoodSearch.php&rfr_id=info%3Asid%2Fen.wikipedia.org%3AFructose" class="Z3988"></span></span> </li> <li id="cite_note-:0-65"><span class="mw-cite-backlink"><b><a href="#cite_ref-:0_65-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPatricia_M._HeacockSteven_R._HertzlerBryan_W._Wolf2002" class="citation journal cs1">Patricia M. Heacock; Steven R. Hertzler; Bryan W. Wolf (2002). <a rel="nofollow" class="external text" href="https://doi.org/10.1093%2Fjn%2F132.9.2601">"Fructose Prefeeding Reduces the Glycemic Response to a High-Glycemic Index, Starchy Food in Humans"</a>. <i>Journal of Nutrition</i>. <b>132</b> (9): 2601–2604. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1093%2Fjn%2F132.9.2601">10.1093/jn/132.9.2601</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/12221216">12221216</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Nutrition&rft.atitle=Fructose+Prefeeding+Reduces+the+Glycemic+Response+to+a+High-Glycemic+Index%2C+Starchy+Food+in+Humans&rft.volume=132&rft.issue=9&rft.pages=2601-2604&rft.date=2002&rft_id=info%3Adoi%2F10.1093%2Fjn%2F132.9.2601&rft_id=info%3Apmid%2F12221216&rft.au=Patricia+M.+Heacock&rft.au=Steven+R.+Hertzler&rft.au=Bryan+W.+Wolf&rft_id=https%3A%2F%2Fdoi.org%2F10.1093%252Fjn%252F132.9.2601&rfr_id=info%3Asid%2Fen.wikipedia.org%3AFructose" class="Z3988"></span></span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fructose&action=edit&section=29" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><span class="noviewer" typeof="mw:File"><a 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class="navbox-group" style="width:1%"><a class="mw-selflink selflink">Fructose</a></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/Fructose_1-phosphate" title="Fructose 1-phosphate">Fructose-1-phosphate</a> → <a href="/wiki/Dihydroxyacetone_phosphate" title="Dihydroxyacetone phosphate">DHAP</a>/<a href="/wiki/Glyceraldehyde" title="Glyceraldehyde">Glyceraldehyde</a> → <a href="/wiki/Glyceraldehyde_3-phosphate" title="Glyceraldehyde 3-phosphate">Glyceraldehyde 3-phosphate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Galactose" title="Galactose">Galactose</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><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Galactose_1-phosphate" title="Galactose 1-phosphate">Galactose-1-phosphate</a> → <a href="/wiki/Glucose_1-phosphate" title="Glucose 1-phosphate">Glucose 1-phosphate</a> → <a href="/wiki/Glucose_6-phosphate" title="Glucose 6-phosphate">Glucose 6-phosphate</a> → <a href="/wiki/Fructose_6-phosphate" title="Fructose 6-phosphate">Fructose 6-phosphate</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Uridine_diphosphate_galactose" title="Uridine diphosphate galactose">Uridine diphosphate galactose</a></li> <li><a href="/wiki/Uridine_diphosphate_glucose" title="Uridine diphosphate glucose">Uridine diphosphate glucose</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Galactitol" 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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 href="/wiki/Glucose" title="Glucose">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 class="mw-selflink selflink">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 href="/wiki/Glucose" title="Glucose">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&action=edit&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 href="/wiki/Glucose" title="Glucose">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="*_Metabolism:_carbohydrate_metabolism_*_fructose_and_galactose_enzymes" 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:Fructose_and_galactose_metabolism_enzymes" title="Template:Fructose and galactose metabolism enzymes"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Fructose_and_galactose_metabolism_enzymes" title="Template talk:Fructose and galactose metabolism enzymes"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Fructose_and_galactose_metabolism_enzymes" title="Special:EditPage/Template:Fructose and galactose metabolism enzymes"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="*_Metabolism:_carbohydrate_metabolism_*_fructose_and_galactose_enzymes" style="font-size:114%;margin:0 4em"> <ul><li><a href="/wiki/Metabolism" title="Metabolism">Metabolism</a>: <a href="/wiki/Carbohydrate_metabolism" title="Carbohydrate metabolism">carbohydrate metabolism</a></li> <li><a class="mw-selflink selflink">fructose</a> and <a href="/wiki/Galactose" title="Galactose">galactose</a> <a href="/wiki/Enzyme" title="Enzyme">enzymes</a></li></ul> </div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a class="mw-selflink selflink">Fructose</a> / <a href="/wiki/Fructolysis" title="Fructolysis">Fructolysis</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/Hepatic_fructokinase" title="Hepatic fructokinase">Hepatic fructokinase</a></li> <li><a href="/wiki/Aldolase_B" title="Aldolase B">Aldolase B</a></li> <li><a href="/wiki/Triokinase" title="Triokinase">Triokinase</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Sorbitol" title="Sorbitol">Sorbitol</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/Sorbitol_dehydrogenase" title="Sorbitol dehydrogenase">Sorbitol dehydrogenase</a></li> <li><a href="/wiki/Aldose_reductase" title="Aldose reductase">Aldose reductase</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Galactose" title="Galactose">Galactose</a> / <a href="/wiki/Galactolysis" title="Galactolysis">Galactolysis</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/Galactokinase" title="Galactokinase">Galactokinase</a></li> <li><a href="/wiki/Galactose-1-phosphate_uridylyltransferase" title="Galactose-1-phosphate uridylyltransferase">Galactose-1-phosphate uridylyltransferase</a>/<a href="/wiki/UDP-glucose_4-epimerase" title="UDP-glucose 4-epimerase">UDP-glucose 4-epimerase</a></li> <li><a href="/wiki/Aldose_reductase" title="Aldose reductase">Aldose reductase</a></li> <li><a href="/wiki/Galactose_mutarotase" title="Galactose mutarotase">Galactose mutarotase</a><sup id="cite_ref-66" class="reference"><a href="#cite_note-66"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Lactose" title="Lactose">Lactose</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/Lactose_synthase" title="Lactose synthase">Lactose synthase</a></li> <li><a href="/wiki/Lactase" title="Lactase">Lactase</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Mannose" title="Mannose">Mannose</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/Mannose_phosphate_isomerase" title="Mannose phosphate isomerase">Mannose phosphate isomerase</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 href="/wiki/Glucose" title="Glucose">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 class="mw-selflink selflink">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 class="mw-selflink selflink">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 href="/wiki/Glucose" title="Glucose">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 class="mw-selflink selflink">Fructose</a></li> <li><a href="/wiki/Galactose" title="Galactose">Galactose</a></li> <li><a href="/wiki/Glucose" title="Glucose">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'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' 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 & Lyle">Tate & 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 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_production" title="Category:Sugar production">Production</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"><style data-mw-deduplicate="TemplateStyles:r1038841319">.mw-parser-output .tooltip-dotted{border-bottom:1px dotted;cursor:help}</style><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1038841319"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1038841319"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1038841319"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1038841319"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1038841319"></div><div role="navigation" class="navbox authority-control" aria-label="Navbox" style="padding:3px"><table class="nowraplinks hlist navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Help:Authority_control" title="Help:Authority control">Authority control databases</a>: National <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q122043#identifiers" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></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><span class="uid"><a rel="nofollow" class="external text" href="https://d-nb.info/gnd/4155521-1">Germany</a></span></li><li><span class="uid"><span class="rt-commentedText tooltip tooltip-dotted" title="Fructose"><a rel="nofollow" class="external text" href="https://id.loc.gov/authorities/sh85052102">United States</a></span></span></li><li><span class="uid"><span class="rt-commentedText tooltip tooltip-dotted" title="Fructose"><a rel="nofollow" class="external text" href="https://catalogue.bnf.fr/ark:/12148/cb12426795f">France</a></span></span></li><li><span class="uid"><span class="rt-commentedText tooltip tooltip-dotted" title="Fructose"><a rel="nofollow" class="external text" href="https://data.bnf.fr/ark:/12148/cb12426795f">BnF data</a></span></span></li><li><span class="uid"><span class="rt-commentedText tooltip tooltip-dotted" title="果糖"><a rel="nofollow" class="external text" href="https://id.ndl.go.jp/auth/ndlna/01214659">Japan</a></span></span></li><li><span class="uid"><span class="rt-commentedText tooltip tooltip-dotted" title="fruktóza"><a rel="nofollow" class="external text" href="https://aleph.nkp.cz/F/?func=find-c&local_base=aut&ccl_term=ica=ph355396&CON_LNG=ENG">Czech Republic</a></span></span></li><li><span class="uid"><span class="rt-commentedText tooltip tooltip-dotted" title="Fruktoze"><a rel="nofollow" class="external text" href="https://kopkatalogs.lv/F?func=direct&local_base=lnc10&doc_number=000352928&P_CON_LNG=ENG">Latvia</a></span></span></li><li><span class="uid"><a rel="nofollow" class="external text" href="http://olduli.nli.org.il/F/?func=find-b&local_base=NLX10&find_code=UID&request=987007552997205171">Israel</a></span></li></ul></div></td></tr></tbody></table></div> <div class="mw-references-wrap"><ol class="references"> <li id="cite_note-66"><span class="mw-cite-backlink"><b><a href="#cite_ref-66">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBeebeFrey1998" class="citation journal cs1">Beebe, Jane A.; Frey, Perry A. (1998-10-01). <a rel="nofollow" class="external text" href="https://pubs.acs.org/doi/10.1021/bi9816047">"Galactose Mutarotase: Purification, Characterization, and Investigations of Two Important Histidine Residues"</a>. <i><a href="/wiki/Biochemistry_(journal)" title="Biochemistry (journal)"> Biochemistry</a></i>. <b>37</b> (42): 14989–14997. <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%2Fbi9816047">10.1021/bi9816047</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0006-2960">0006-2960</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Biochemistry&rft.atitle=Galactose+Mutarotase%3A+Purification%2C+Characterization%2C+and+Investigations+of+Two+Important+Histidine+Residues&rft.volume=37&rft.issue=42&rft.pages=14989-14997&rft.date=1998-10-01&rft_id=info%3Adoi%2F10.1021%2Fbi9816047&rft.issn=0006-2960&rft.aulast=Beebe&rft.aufirst=Jane+A.&rft.au=Frey%2C+Perry+A.&rft_id=https%3A%2F%2Fpubs.acs.org%2Fdoi%2F10.1021%2Fbi9816047&rfr_id=info%3Asid%2Fen.wikipedia.org%3AFructose" class="Z3988"></span></span> </li> </ol></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?type=1x1" alt="" width="1" height="1" style="border: none; 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