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data-event-name="pinnable-header.vector-toc.pin">move to sidebar</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-toc.unpin">hide</button> </div> <ul class="vector-toc-contents" id="mw-panel-toc-list"> <li id="toc-mw-content-text" class="vector-toc-list-item vector-toc-level-1"> <a href="#" class="vector-toc-link"> <div class="vector-toc-text">(Top)</div> </a> </li> <li id="toc-Classification" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Classification"> <div class="vector-toc-text"> <span class="vector-toc-numb">1</span> <span>Classification</span> </div> </a> <button aria-controls="toc-Classification-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 Classification subsection</span> </button> <ul id="toc-Classification-sublist" class="vector-toc-list"> <li id="toc-Aldohexoses" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Aldohexoses"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.1</span> <span>Aldohexoses</span> </div> </a> <ul id="toc-Aldohexoses-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Ketohexoses" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Ketohexoses"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.2</span> <span>Ketohexoses</span> </div> </a> <ul id="toc-Ketohexoses-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-3-Ketohexoses" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#3-Ketohexoses"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>3-Ketohexoses</span> </div> </a> <ul id="toc-3-Ketohexoses-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Cyclic_forms" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Cyclic_forms"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Cyclic forms</span> </div> </a> <ul id="toc-Cyclic_forms-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Chemical_properties" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Chemical_properties"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Chemical properties</span> </div> </a> <ul id="toc-Chemical_properties-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Natural_occurrence_and_uses" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Natural_occurrence_and_uses"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Natural occurrence and uses</span> </div> </a> <ul id="toc-Natural_occurrence_and_uses-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Deoxyhexoses" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Deoxyhexoses"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Deoxyhexoses</span> </div> </a> <ul id="toc-Deoxyhexoses-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</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 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</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 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</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">Hexose</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 43 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-43" 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">43 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/Heksose" title="Heksose – Afrikaans" lang="af" hreflang="af" data-title="Heksose" 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%87%D9%83%D8%B3%D9%88%D8%B2" title="هكسوز – Arabic" lang="ar" hreflang="ar" data-title="هكسوز" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-bn mw-list-item"><a href="https://bn.wikipedia.org/wiki/%E0%A6%B9%E0%A7%87%E0%A6%95%E0%A7%8D%E0%A6%B8%E0%A7%8B%E0%A6%9C" title="হেক্সোজ – Bangla" lang="bn" hreflang="bn" data-title="হেক্সোজ" 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%93%D0%B5%D0%BA%D1%81%D0%BE%D0%B7%D1%8B" title="Гексозы – Belarusian" lang="be" hreflang="be" data-title="Гексозы" data-language-autonym="Беларуская" data-language-local-name="Belarusian" class="interlanguage-link-target"><span>Беларуская</span></a></li><li class="interlanguage-link interwiki-be-x-old mw-list-item"><a href="https://be-tarask.wikipedia.org/wiki/%D0%93%D0%B5%D0%BA%D1%81%D0%BE%D0%B7%D1%8B" title="Гексозы – Belarusian (Taraškievica orthography)" lang="be-tarask" hreflang="be-tarask" data-title="Гексозы" 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%A5%D0%B5%D0%BA%D1%81%D0%BE%D0%B7%D0%B0" title="Хексоза – Bulgarian" lang="bg" hreflang="bg" data-title="Хексоза" 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/Heksoza" title="Heksoza – Bosnian" lang="bs" hreflang="bs" data-title="Heksoza" 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/Hexosa" title="Hexosa – Catalan" lang="ca" hreflang="ca" data-title="Hexosa" 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/Hex%C3%B3zy" title="Hexózy – Czech" lang="cs" hreflang="cs" data-title="Hexózy" 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/Hexose" title="Hexose – Danish" lang="da" hreflang="da" data-title="Hexose" 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/Hexosen" title="Hexosen – German" lang="de" hreflang="de" data-title="Hexosen" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Hexosa" title="Hexosa – Spanish" lang="es" hreflang="es" data-title="Hexosa" 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/Heksozo" title="Heksozo – Esperanto" lang="eo" hreflang="eo" data-title="Heksozo" 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/Hexosa" title="Hexosa – Basque" lang="eu" hreflang="eu" data-title="Hexosa" 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%87%DA%AF%D8%B2%D9%88%D8%B2" title="هگزوز – Persian" lang="fa" hreflang="fa" data-title="هگزوز" 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/Hexose" title="Hexose – French" lang="fr" hreflang="fr" data-title="Hexose" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Hexosa" title="Hexosa – Galician" lang="gl" hreflang="gl" data-title="Hexosa" 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/%EC%9C%A1%ED%83%84%EB%8B%B9" title="육탄당 – Korean" lang="ko" hreflang="ko" data-title="육탄당" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Heksoza" title="Heksoza – Croatian" lang="hr" hreflang="hr" data-title="Heksoza" 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/Heksosa" title="Heksosa – Indonesian" lang="id" hreflang="id" data-title="Heksosa" 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-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Zucchero_esoso" title="Zucchero esoso – Italian" lang="it" hreflang="it" data-title="Zucchero esoso" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-la mw-list-item"><a href="https://la.wikipedia.org/wiki/Hexosum" title="Hexosum – Latin" lang="la" hreflang="la" data-title="Hexosum" data-language-autonym="Latina" data-language-local-name="Latin" class="interlanguage-link-target"><span>Latina</span></a></li><li class="interlanguage-link interwiki-lmo mw-list-item"><a href="https://lmo.wikipedia.org/wiki/Exosa" title="Exosa – Lombard" lang="lmo" hreflang="lmo" data-title="Exosa" data-language-autonym="Lombard" data-language-local-name="Lombard" class="interlanguage-link-target"><span>Lombard</span></a></li><li class="interlanguage-link interwiki-ml mw-list-item"><a href="https://ml.wikipedia.org/wiki/%E0%B4%B9%E0%B5%86%E0%B4%95%E0%B5%8D%E0%B4%B8%E0%B5%8B%E0%B4%B8%E0%B5%8D" title="ഹെക്സോസ് – Malayalam" lang="ml" hreflang="ml" data-title="ഹെക്സോസ്" data-language-autonym="മലയാളം" data-language-local-name="Malayalam" class="interlanguage-link-target"><span>മലയാളം</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Hexose" title="Hexose – Dutch" lang="nl" hreflang="nl" data-title="Hexose" 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%98%E3%82%AD%E3%82%BD%E3%83%BC%E3%82%B9" title="ヘキソース – Japanese" lang="ja" hreflang="ja" data-title="ヘキソース" 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/Heksose" title="Heksose – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Heksose" 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-oc mw-list-item"><a href="https://oc.wikipedia.org/wiki/Ex%C3%B2sa" title="Exòsa – Occitan" lang="oc" hreflang="oc" data-title="Exòsa" 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/Geksozalar" title="Geksozalar – Uzbek" lang="uz" hreflang="uz" data-title="Geksozalar" 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/Heksozy" title="Heksozy – Polish" lang="pl" hreflang="pl" data-title="Heksozy" 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/Hexose" title="Hexose – Portuguese" lang="pt" hreflang="pt" data-title="Hexose" 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/Hexoz%C4%83" title="Hexoză – Romanian" lang="ro" hreflang="ro" data-title="Hexoză" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%93%D0%B5%D0%BA%D1%81%D0%BE%D0%B7%D1%8B" title="Гексозы – Russian" lang="ru" hreflang="ru" data-title="Гексозы" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Hex%C3%B3za" title="Hexóza – Slovak" lang="sk" hreflang="sk" data-title="Hexóza" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Heksoza" title="Heksoza – Serbian" lang="sr" hreflang="sr" data-title="Heksoza" 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/Heksoza" title="Heksoza – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Heksoza" 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-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Heksoosit" title="Heksoosit – Finnish" lang="fi" hreflang="fi" data-title="Heksoosit" 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/Hexos" title="Hexos – Swedish" lang="sv" hreflang="sv" data-title="Hexos" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Heksoz" title="Heksoz – Turkish" lang="tr" hreflang="tr" data-title="Heksoz" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%93%D0%B5%D0%BA%D1%81%D0%BE%D0%B7%D0%B8" title="Гексози – Ukrainian" lang="uk" hreflang="uk" data-title="Гексози" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Hexose" title="Hexose – Vietnamese" lang="vi" hreflang="vi" data-title="Hexose" 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-zh-yue mw-list-item"><a href="https://zh-yue.wikipedia.org/wiki/%E5%B7%B1%E9%86%A3" title="己醣 – Cantonese" lang="yue" hreflang="yue" data-title="己醣" 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/%E5%B7%B1%E7%B3%96" title="己糖 – Chinese" lang="zh" hreflang="zh" data-title="己糖" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target"><span>中文</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span class="wb-langlinks-edit wb-langlinks-link"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q339725#sitelinks-wikipedia" title="Edit interlanguage links" class="wbc-editpage">Edit links</a></span></div> </div> </div> </div> </header> <div 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data-mw-deduplicate="TemplateStyles:r1237032888/mw-parser-output/.tmulti">.mw-parser-output .tmulti .multiimageinner{display:flex;flex-direction:column}.mw-parser-output .tmulti .trow{display:flex;flex-direction:row;clear:left;flex-wrap:wrap;width:100%;box-sizing:border-box}.mw-parser-output .tmulti .tsingle{margin:1px;float:left}.mw-parser-output .tmulti .theader{clear:both;font-weight:bold;text-align:center;align-self:center;background-color:transparent;width:100%}.mw-parser-output .tmulti .thumbcaption{background-color:transparent}.mw-parser-output .tmulti .text-align-left{text-align:left}.mw-parser-output .tmulti .text-align-right{text-align:right}.mw-parser-output .tmulti .text-align-center{text-align:center}@media all and (max-width:720px){.mw-parser-output .tmulti .thumbinner{width:100%!important;box-sizing:border-box;max-width:none!important;align-items:center}.mw-parser-output .tmulti .trow{justify-content:center}.mw-parser-output .tmulti .tsingle{float:none!important;max-width:100%!important;box-sizing:border-box;text-align:center}.mw-parser-output .tmulti .tsingle .thumbcaption{text-align:left}.mw-parser-output .tmulti .trow>.thumbcaption{text-align:center}}@media screen{html.skin-theme-clientpref-night .mw-parser-output .tmulti .multiimageinner img{background-color:white}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .tmulti .multiimageinner img{background-color:white}}</style><div class="thumb tmulti tright"><div class="thumbinner multiimageinner" style="width:312px;max-width:312px"><div class="trow"><div class="tsingle" style="width:153px;max-width:153px"><div class="thumbimage" style="height:254px;overflow:hidden"><span typeof="mw:File"><a href="/wiki/File:DGlucose_Fischer.svg" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/1/14/DGlucose_Fischer.svg/151px-DGlucose_Fischer.svg.png" decoding="async" width="151" height="255" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/14/DGlucose_Fischer.svg/227px-DGlucose_Fischer.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/14/DGlucose_Fischer.svg/302px-DGlucose_Fischer.svg.png 2x" data-file-width="83" data-file-height="140" /></a></span></div><div class="thumbcaption text-align-center"><span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">D</span></span>-<a href="/wiki/Glucose" title="Glucose">Glucose</a>.</div></div><div class="tsingle" style="width:155px;max-width:155px"><div class="thumbimage" style="height:254px;overflow:hidden"><span typeof="mw:File"><a href="/wiki/File:D-Fructose.svg" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e5/D-Fructose.svg/153px-D-Fructose.svg.png" decoding="async" width="153" height="254" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e5/D-Fructose.svg/230px-D-Fructose.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e5/D-Fructose.svg/306px-D-Fructose.svg.png 2x" data-file-width="126" data-file-height="209" /></a></span></div><div class="thumbcaption text-align-center"><span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">D</span></span>-<a href="/wiki/Fructose" title="Fructose">Fructose</a>.</div></div></div><div class="trow" style="display:flow-root"><div class="thumbcaption" style="text-align:center">Two important hexoses, in the <a href="/wiki/Fischer_projection" title="Fischer projection">Fischer projection</a>.</div></div></div></div> <p>In <a href="/wiki/Chemistry" title="Chemistry">chemistry</a>, a <b>hexose</b> is a <a href="/wiki/Monosaccharide" title="Monosaccharide">monosaccharide</a> (simple sugar) with six <a href="/wiki/Carbon" title="Carbon">carbon</a> atoms.<sup id="cite_ref-lind2007_1-0" class="reference"><a href="#cite_note-lind2007-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-robyt1997_2-0" class="reference"><a href="#cite_note-robyt1997-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> The chemical formula for all hexoses is <style data-mw-deduplicate="TemplateStyles:r1123817410">.mw-parser-output .template-chem2-su{display:inline-block;font-size:80%;line-height:1;vertical-align:-0.35em}.mw-parser-output .template-chem2-su>span{display:block;text-align:left}.mw-parser-output sub.template-chem2-sub{font-size:80%;vertical-align:-0.35em}.mw-parser-output sup.template-chem2-sup{font-size:80%;vertical-align:0.65em}</style><span class="chemf nowrap">C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">12</sub>O<sub class="template-chem2-sub">6</sub></span>, and their <a href="/wiki/Molecular_weight" class="mw-redirect" title="Molecular weight">molecular weight</a> is 180.156 g/mol.<sup id="cite_ref-:0_3-0" class="reference"><a href="#cite_note-:0-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p><p>Hexoses exist in two forms, open-chain or cyclic, that easily convert into each other in aqueous solutions.<sup id="cite_ref-morr1998_4-0" class="reference"><a href="#cite_note-morr1998-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> The open-chain form of a hexose, which usually is favored in solutions, has the general structure <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">H−(CHOH)<sub class="template-chem2-sub"><i>n</i>−1</sub>−C(=O)−(CHOH)<sub class="template-chem2-sub">6−<i>n</i></sub>−H</span>, where <i>n</i> is 1, 2, 3, 4, 5. Namely, five of the carbons have one <a href="/wiki/Hydroxyl" class="mw-redirect" title="Hydroxyl">hydroxyl</a> functional group (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−OH</span>) each, connected by a <a href="/wiki/Single_bond" title="Single bond">single bond</a>, and one has an oxo group (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">=O</span>), forming a <a href="/wiki/Carbonyl" class="mw-redirect" title="Carbonyl">carbonyl</a> group (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C=O</span>). The remaining bonds of the carbon atoms are satisfied by seven <a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a> atoms. The carbons are commonly numbered 1 to 6 starting at the end closest to the carbonyl. </p><p>Hexoses are extremely important in <a href="/wiki/Biochemistry" title="Biochemistry">biochemistry</a>, both as isolated molecules (such as <a href="/wiki/Glucose" title="Glucose">glucose</a> and <a href="/wiki/Fructose" title="Fructose">fructose</a>) and as building blocks of other compounds such as <a href="/wiki/Starch" title="Starch">starch</a>, <a href="/wiki/Cellulose" title="Cellulose">cellulose</a>, and <a href="/wiki/Glycoside" title="Glycoside">glycosides</a>. Hexoses can form <a href="/wiki/Disaccharide" title="Disaccharide">dihexose</a> (like <a href="/wiki/Sucrose" title="Sucrose">sucrose</a>) by a condensation reaction that makes 1,6-<a href="/wiki/Glycosidic_bond" title="Glycosidic bond">glycosidic bond</a>. </p><p>When the carbonyl is in position 1, forming an <a href="/wiki/Formyl_group" class="mw-redirect" title="Formyl group">formyl group</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−CH=O</span>), the sugar is called an <b>aldohexose</b>, a special case of <a href="/wiki/Aldose" title="Aldose">aldose</a>. Otherwise, if the carbonyl position is 2 or 3, the sugar is a derivative of a <a href="/wiki/Ketone" title="Ketone">ketone</a>, and is called a <b>ketohexose</b>, a special case of <a href="/wiki/Ketose" title="Ketose">ketose</a>; specifically, an <b><i>n</i>-ketohexose</b>.<sup id="cite_ref-lind2007_1-1" class="reference"><a href="#cite_note-lind2007-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-robyt1997_2-1" class="reference"><a href="#cite_note-robyt1997-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> However, the 3-ketohexoses have not been observed in nature, and are difficult to synthesize;<sup id="cite_ref-yuen1961_5-0" class="reference"><a href="#cite_note-yuen1961-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> so the term "ketohexose" usually means 2-ketohexose. </p><p>In the linear form, there are 16 aldohexoses and eight 2-ketohexoses, <a href="/wiki/Stereoisomer" class="mw-redirect" title="Stereoisomer">stereoisomers</a> that differ in the spatial position of the hydroxyl groups. These species occur in pairs of <a href="/wiki/Optical_isomer" class="mw-redirect" title="Optical isomer">optical isomers</a>. Each pair has a conventional name (like "glucose" or "fructose"), and the two members are labeled "<span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">D</span></span>-" or "<span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">L</span></span>-", depending on whether the hydroxyl in position 5, in the <a href="/wiki/Fischer_projection" title="Fischer projection">Fischer projection</a> of the molecule, is to the right or to the left of the axis, respectively. These labels are independent of the <a href="/wiki/Optical_activity" class="mw-redirect" title="Optical activity">optical activity</a> of the isomers. In general, only one of the two enantiomers occurs naturally (for example, <span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">D</span></span>-glucose) and can be <a href="/wiki/Metabolism" title="Metabolism">metabolized</a> by animals or <a href="/wiki/Fermentation" title="Fermentation">fermented</a> by <a href="/wiki/Yeast" title="Yeast">yeasts</a>. </p><p>The term "hexose" sometimes is assumed to include <b>deoxyhexoses</b>, such as <a href="/wiki/Fucose" title="Fucose">fucose</a> and <a href="/wiki/Rhamnose" title="Rhamnose">rhamnose</a>: compounds with general formula <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">12</sub>O<sub class="template-chem2-sub">6−<i>y</i></sub></span> that can be described as derived from hexoses by replacement of one or more hydroxyl groups with hydrogen atoms. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Classification">Classification</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Hexose&action=edit&section=1" title="Edit section: Classification"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Aldohexoses">Aldohexoses</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Hexose&action=edit&section=2" title="Edit section: Aldohexoses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The aldohexoses are a subclass of the hexoses which, in the linear form, have the carbonyl at carbon 1, forming an <a href="/wiki/Aldehyde" title="Aldehyde">aldehyde</a> derivative with structure <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">H−C(=O)−(CHOH)<sub class="template-chem2-sub">5</sub>−H</span>.<sup id="cite_ref-lind2007_1-2" class="reference"><a href="#cite_note-lind2007-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-robyt1997_2-2" class="reference"><a href="#cite_note-robyt1997-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> The most important example is <a href="/wiki/Glucose" title="Glucose">glucose</a>. </p><p>In linear form, an aldohexose has four <a href="/wiki/Chiral_centre" class="mw-redirect" title="Chiral centre">chiral centres</a>, which give 16 possible aldohexose <a href="/wiki/Stereoisomer" class="mw-redirect" title="Stereoisomer">stereoisomers</a> (2<sup>4</sup>),comprising 8 pairs of <a href="/wiki/Enantiomer" title="Enantiomer">enantiomers</a>. The linear forms of the eight <span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">D</span></span>-aldohexoses, in the <a href="/wiki/Fischer_projection" title="Fischer projection">Fischer projection</a>, are </p> <ul class="gallery mw-gallery-traditional"> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:DAllose_Fischer.svg" class="mw-file-description" title="D-Allose 000"><img alt="D-Allose 000" src="//upload.wikimedia.org/wikipedia/commons/thumb/1/1e/DAllose_Fischer.svg/61px-DAllose_Fischer.svg.png" decoding="async" width="61" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/1e/DAllose_Fischer.svg/92px-DAllose_Fischer.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/1e/DAllose_Fischer.svg/123px-DAllose_Fischer.svg.png 2x" data-file-width="72" data-file-height="140" /></a></span></div> <div class="gallerytext"> <div align="center"><span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">D</span></span>-<a href="/wiki/Allose" title="Allose">Allose</a><br />000</div></div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:DAltrose_Fischer.svg" class="mw-file-description" title="D-Altrose 001"><img alt="D-Altrose 001" src="//upload.wikimedia.org/wikipedia/commons/thumb/7/78/DAltrose_Fischer.svg/71px-DAltrose_Fischer.svg.png" decoding="async" width="71" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/78/DAltrose_Fischer.svg/107px-DAltrose_Fischer.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/78/DAltrose_Fischer.svg/142px-DAltrose_Fischer.svg.png 2x" data-file-width="83" data-file-height="140" /></a></span></div> <div class="gallerytext"> <div align="center"><span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">D</span></span>-<a href="/wiki/Altrose" title="Altrose">Altrose</a><br />001</div></div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:DGlucose_Fischer.svg" class="mw-file-description" title="D-Glucose 010"><img alt="D-Glucose 010" src="//upload.wikimedia.org/wikipedia/commons/thumb/1/14/DGlucose_Fischer.svg/71px-DGlucose_Fischer.svg.png" decoding="async" width="71" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/14/DGlucose_Fischer.svg/107px-DGlucose_Fischer.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/14/DGlucose_Fischer.svg/142px-DGlucose_Fischer.svg.png 2x" data-file-width="83" data-file-height="140" /></a></span></div> <div class="gallerytext"> <div align="center"><span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">D</span></span>-<a href="/wiki/Glucose" title="Glucose">Glucose</a><br />010</div></div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Mannose.svg" class="mw-file-description" title="D-Mannose 011"><img alt="D-Mannose 011" src="//upload.wikimedia.org/wikipedia/commons/thumb/4/45/Mannose.svg/71px-Mannose.svg.png" decoding="async" width="71" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/45/Mannose.svg/107px-Mannose.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/45/Mannose.svg/142px-Mannose.svg.png 2x" data-file-width="83" data-file-height="140" /></a></span></div> <div class="gallerytext"> <div align="center"><span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">D</span></span>-<a href="/wiki/Mannose" title="Mannose">Mannose</a><br />011</div></div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:DGulose_Fischer.svg" class="mw-file-description" title="D-Gulose 100"><img alt="D-Gulose 100" src="//upload.wikimedia.org/wikipedia/commons/thumb/8/80/DGulose_Fischer.svg/71px-DGulose_Fischer.svg.png" decoding="async" width="71" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/80/DGulose_Fischer.svg/107px-DGulose_Fischer.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/80/DGulose_Fischer.svg/142px-DGulose_Fischer.svg.png 2x" data-file-width="83" data-file-height="140" /></a></span></div> <div class="gallerytext"> <div align="center"><span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">D</span></span>-<a href="/wiki/Gulose" title="Gulose">Gulose</a><br />100</div></div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:DIdose_Fischer.svg" class="mw-file-description" title="D-Idose 101"><img alt="D-Idose 101" src="//upload.wikimedia.org/wikipedia/commons/thumb/4/45/DIdose_Fischer.svg/71px-DIdose_Fischer.svg.png" decoding="async" width="71" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/45/DIdose_Fischer.svg/107px-DIdose_Fischer.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/45/DIdose_Fischer.svg/142px-DIdose_Fischer.svg.png 2x" data-file-width="83" data-file-height="140" /></a></span></div> <div class="gallerytext"> <div align="center"><span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">D</span></span>-<a href="/wiki/Idose" title="Idose">Idose</a><br />101</div></div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:DGalactose_Fischer.svg" class="mw-file-description" title="D-Galactose 110"><img alt="D-Galactose 110" src="//upload.wikimedia.org/wikipedia/commons/thumb/7/7b/DGalactose_Fischer.svg/71px-DGalactose_Fischer.svg.png" decoding="async" width="71" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/7b/DGalactose_Fischer.svg/107px-DGalactose_Fischer.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/7b/DGalactose_Fischer.svg/142px-DGalactose_Fischer.svg.png 2x" data-file-width="83" data-file-height="140" /></a></span></div> <div class="gallerytext"> <div align="center"><span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">D</span></span>-<a href="/wiki/Galactose" title="Galactose">Galactose</a><br />110</div></div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:DTalose_Fischer.svg" class="mw-file-description" title="D-Talose 111"><img alt="D-Talose 111" src="//upload.wikimedia.org/wikipedia/commons/thumb/8/8b/DTalose_Fischer.svg/71px-DTalose_Fischer.svg.png" decoding="async" width="71" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/8b/DTalose_Fischer.svg/107px-DTalose_Fischer.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/8b/DTalose_Fischer.svg/142px-DTalose_Fischer.svg.png 2x" data-file-width="83" data-file-height="140" /></a></span></div> <div class="gallerytext"> <div align="center"><span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">D</span></span>-<a href="/wiki/Talose" title="Talose">Talose</a><br />111</div></div> </li> </ul> <p>Of these <span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">D</span></span>-isomers, all except <span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">D</span></span>-altrose occur in living organisms, but only three are common: <span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">D</span></span>-glucose, <span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">D</span></span>-galactose, and <span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">D</span></span>-mannose. The <span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">L</span></span>-isomers are generally absent in living organisms; however, <span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">L</span></span>-altrose has been isolated from strains of the bacterium <i><a href="/wiki/Butyrivibrio_fibrisolvens" class="mw-redirect" title="Butyrivibrio fibrisolvens">Butyrivibrio fibrisolvens</a></i>.<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>When drawn in this order, the Fischer projections of the <span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">D</span></span>-aldohexoses can be identified with the 3-digit <a href="/wiki/Binary_number" title="Binary number">binary numbers</a> from 0 to 7, namely 000, 001, 010, 011, 100, 101, 110, 111. The three <a href="/wiki/Bit" title="Bit">bits</a>, from left to right, indicate the position of the hydroxyls on carbons 4, 3, and 2, respectively: to the right if the bit value is 0, and to the left if the value is 1. </p><p>The chemist <a href="/wiki/Hermann_Emil_Fischer" class="mw-redirect" title="Hermann Emil Fischer">Emil Fischer</a> is said<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (July 2020)">citation needed</span></a></i>]</sup> to have devised the following <a href="/wiki/Mnemonic" title="Mnemonic">mnemonic</a> device for remembering the order given above, which corresponds to the configurations about the chiral centers when ordered as 3-bit binary strings: </p> <dl><dd><b>All</b> <b>altr</b>uists <b>gl</b>adly <b>ma</b>ke <b>gu</b>m <b>i</b>n <b>gal</b>lon <b>ta</b>nks.</dd></dl> <p>referring to <b>all</b>ose, <b>altr</b>ose, <b>gl</b>ucose, <b>ma</b>nnose, <b>gu</b>lose, <b>i</b>dose, <b>gal</b>actose, <b>ta</b>lose. </p><p>The Fischer diagrams of the eight <span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">L</span></span>-aldohexoses are the mirror images of the corresponding <span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">D</span></span>-isomers; with all hydroxyls reversed, including the one on carbon 5. </p> <div class="mw-heading mw-heading3"><h3 id="Ketohexoses">Ketohexoses</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Hexose&action=edit&section=3" title="Edit section: Ketohexoses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>A ketohexose is a <a href="/wiki/Ketone" title="Ketone">ketone</a>-containing hexose.<sup id="cite_ref-lind2007_1-3" class="reference"><a href="#cite_note-lind2007-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-robyt1997_2-3" class="reference"><a href="#cite_note-robyt1997-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-orch1980_7-0" class="reference"><a href="#cite_note-orch1980-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> The important ketohexoses are the 2-ketohexoses, and the most important 2-ketose is <a href="/wiki/Fructose" title="Fructose">fructose</a>. </p><p>Besides the 2-ketoses, there are only the 3-Ketoses, and they do not exist in nature, although at least one 3-ketohexose has been synthesized, with great difficulty. </p><p>In the linear form, the 2-ketohexoses have three chiral centers and therefore eight possible stereoisomers (2<sup>3</sup>), comprising four pairs of enantiomers. The four <span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">D</span></span>-isomers are: </p> <ul class="gallery mw-gallery-traditional"> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:DPsicose_Fischer.svg" class="mw-file-description" title="D-Psicose[8]"><img alt="D-Psicose[8]" src="//upload.wikimedia.org/wikipedia/commons/thumb/7/7c/DPsicose_Fischer.svg/62px-DPsicose_Fischer.svg.png" decoding="async" width="62" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/7c/DPsicose_Fischer.svg/92px-DPsicose_Fischer.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/7c/DPsicose_Fischer.svg/123px-DPsicose_Fischer.svg.png 2x" data-file-width="70" data-file-height="136" /></a></span></div> <div class="gallerytext"> <div align="center"><span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">D</span></span>-<a href="/wiki/Psicose" title="Psicose">Psicose</a><sup id="cite_ref-pub-D-psicose_8-0" class="reference"><a href="#cite_note-pub-D-psicose-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup></div></div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:D-Fructose.svg" class="mw-file-description" title="D-Fructose[9]"><img alt="D-Fructose[9]" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e5/D-Fructose.svg/72px-D-Fructose.svg.png" decoding="async" width="72" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e5/D-Fructose.svg/108px-D-Fructose.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e5/D-Fructose.svg/144px-D-Fructose.svg.png 2x" data-file-width="126" data-file-height="209" /></a></span></div> <div class="gallerytext"> <div align="center"><span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">D</span></span>-<a href="/wiki/Fructose" title="Fructose">Fructose</a><sup id="cite_ref-pub-fructose_9-0" class="reference"><a href="#cite_note-pub-fructose-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup></div></div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:DSorbose_Fischer.svg" class="mw-file-description" title="D-Sorbose[10]"><img alt="D-Sorbose[10]" src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/DSorbose_Fischer.svg/70px-DSorbose_Fischer.svg.png" decoding="async" width="70" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/DSorbose_Fischer.svg/106px-DSorbose_Fischer.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d6/DSorbose_Fischer.svg/141px-DSorbose_Fischer.svg.png 2x" data-file-width="80" data-file-height="136" /></a></span></div> <div class="gallerytext"> <div align="center"><span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">D</span></span>-<a href="/wiki/Sorbose" title="Sorbose">Sorbose</a><sup id="cite_ref-pub-sorbose_10-0" class="reference"><a href="#cite_note-pub-sorbose-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup></div></div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:DTagatose_Fischer.svg" class="mw-file-description" title="D-Tagatose[11]"><img alt="D-Tagatose[11]" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6c/DTagatose_Fischer.svg/70px-DTagatose_Fischer.svg.png" decoding="async" width="70" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6c/DTagatose_Fischer.svg/106px-DTagatose_Fischer.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6c/DTagatose_Fischer.svg/141px-DTagatose_Fischer.svg.png 2x" data-file-width="80" data-file-height="136" /></a></span></div> <div class="gallerytext"> <div align="center"><span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">D</span></span>-<a href="/wiki/Tagatose" title="Tagatose">Tagatose</a><sup id="cite_ref-pub-tagatose_11-0" class="reference"><a href="#cite_note-pub-tagatose-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup></div></div> </li> </ul> <p>The corresponding <span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">L</span></span> forms have the hydroxyls on carbons 3, 4,and 5 reversed. Below are depiction of the eight isomers in an alternative style: </p> <ul class="gallery mw-gallery-traditional"> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Psicose.png" class="mw-file-description" title="D-Psicose"><img alt="D-Psicose" src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d0/Psicose.png/120px-Psicose.png" decoding="async" width="120" height="48" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d0/Psicose.png/180px-Psicose.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d0/Psicose.png/240px-Psicose.png 2x" data-file-width="1381" data-file-height="558" /></a></span></div> <div class="gallerytext"> <div align="center"><span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">D</span></span>-<a href="/wiki/Psicose" title="Psicose">Psicose</a></div></div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:D-fructose_CASCC.png" class="mw-file-description" title="D-Fructose"><img alt="D-Fructose" src="//upload.wikimedia.org/wikipedia/commons/thumb/f/fb/D-fructose_CASCC.png/120px-D-fructose_CASCC.png" decoding="async" width="120" height="48" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/fb/D-fructose_CASCC.png/180px-D-fructose_CASCC.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/fb/D-fructose_CASCC.png/240px-D-fructose_CASCC.png 2x" data-file-width="1381" data-file-height="558" /></a></span></div> <div class="gallerytext"> <div align="center"><span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">D</span></span>-<a href="/wiki/Fructose" title="Fructose">Fructose</a></div></div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:D-sorbose.png" class="mw-file-description" title="D-Sorbose"><img alt="D-Sorbose" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/28/D-sorbose.png/120px-D-sorbose.png" decoding="async" width="120" height="48" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/28/D-sorbose.png/180px-D-sorbose.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/28/D-sorbose.png/240px-D-sorbose.png 2x" data-file-width="1381" data-file-height="558" /></a></span></div> <div class="gallerytext"> <div align="center"><span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">D</span></span>-<a href="/wiki/Sorbose" title="Sorbose">Sorbose</a></div></div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Tagatose.png" class="mw-file-description" title="D-Tagatose"><img alt="D-Tagatose" src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b3/Tagatose.png/120px-Tagatose.png" decoding="async" width="120" height="48" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b3/Tagatose.png/180px-Tagatose.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b3/Tagatose.png/240px-Tagatose.png 2x" data-file-width="1381" data-file-height="558" /></a></span></div> <div class="gallerytext"> <div align="center"><span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">D</span></span>-<a href="/wiki/Tagatose" title="Tagatose">Tagatose</a></div></div> </li> </ul> <ul class="gallery mw-gallery-traditional"> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:L-psicose.png" class="mw-file-description" title="L-Psicose"><img alt="L-Psicose" src="//upload.wikimedia.org/wikipedia/commons/thumb/4/4b/L-psicose.png/120px-L-psicose.png" decoding="async" width="120" height="48" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/4b/L-psicose.png/180px-L-psicose.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/4b/L-psicose.png/240px-L-psicose.png 2x" data-file-width="1381" data-file-height="558" /></a></span></div> <div class="gallerytext"> <div align="center"><span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">L</span></span>-<a href="/wiki/Psicose" title="Psicose">Psicose</a></div></div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:L-fructose.png" class="mw-file-description" title="L-Fructose"><img alt="L-Fructose" src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b6/L-fructose.png/120px-L-fructose.png" decoding="async" width="120" height="48" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b6/L-fructose.png/180px-L-fructose.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b6/L-fructose.png/240px-L-fructose.png 2x" data-file-width="1381" data-file-height="558" /></a></span></div> <div class="gallerytext"> <div align="center"><span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">L</span></span>-<a href="/wiki/Fructose" title="Fructose">Fructose</a></div></div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Sorbose.png" class="mw-file-description" title="L-Sorbose"><img alt="L-Sorbose" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6b/Sorbose.png/120px-Sorbose.png" decoding="async" width="120" height="48" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6b/Sorbose.png/180px-Sorbose.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6b/Sorbose.png/240px-Sorbose.png 2x" data-file-width="1381" data-file-height="558" /></a></span></div> <div class="gallerytext"> <div align="center"><span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">L</span></span>-<a href="/wiki/Sorbose" title="Sorbose">Sorbose</a></div></div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:L-tagatose.png" class="mw-file-description" title="L-Tagatose"><img alt="L-Tagatose" src="//upload.wikimedia.org/wikipedia/commons/thumb/f/fc/L-tagatose.png/120px-L-tagatose.png" decoding="async" width="120" height="48" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/fc/L-tagatose.png/180px-L-tagatose.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/fc/L-tagatose.png/240px-L-tagatose.png 2x" data-file-width="1381" data-file-height="558" /></a></span></div> <div class="gallerytext"> <div align="center"><span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">L</span></span>-<a href="/wiki/Tagatose" title="Tagatose">Tagatose</a></div></div> </li> </ul> <div class="mw-heading mw-heading2"><h2 id="3-Ketohexoses">3-Ketohexoses</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Hexose&action=edit&section=4" title="Edit section: 3-Ketohexoses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In theory, the ketohexoses include also the 3-ketohexoses, which have the carbonyl in position 3; namely <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">H−(CHOH)<sub class="template-chem2-sub">2</sub>−C(=O)−(CHOH)<sub class="template-chem2-sub">3</sub>−H</span>. However, these compounds are not known to occur in nature, and are difficult to synthesize.<sup id="cite_ref-yuen1961_5-1" class="reference"><a href="#cite_note-yuen1961-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p><p>In 1897, an <a href="/wiki/Fermentation" title="Fermentation">unfermentable</a> product obtained by treatment of fructose with <a href="/wiki/Base_(chemistry)" title="Base (chemistry)">bases</a>, in particular <a href="/wiki/Lead(II)_hydroxide" title="Lead(II) hydroxide">lead(II) hydroxide</a>, was given the name <i>glutose</i>, a <a href="/wiki/Portmanteau" class="mw-redirect" title="Portmanteau">portmanteau</a> of <i>glucose</i> and <i>fructose</i>, and was claimed to be a 3-ketohexose.<sup id="cite_ref-bruyn1897_12-0" class="reference"><a href="#cite_note-bruyn1897-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-clark1949_13-0" class="reference"><a href="#cite_note-clark1949-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> However, subsequent studies showed that the substance was a mixture of various other compounds.<sup id="cite_ref-clark1949_13-1" class="reference"><a href="#cite_note-clark1949-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-sera1962_14-0" class="reference"><a href="#cite_note-sera1962-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p><p>The unequivocal synthesis and isolation of a 3-ketohexose, <a href="/w/index.php?title=Xylo-3-hexulose&action=edit&redlink=1" class="new" title="Xylo-3-hexulose (page does not exist)"><i>xylo</i>-3-hexulose</a>, through a rather complex route, was first reported in 1961 by <a href="/w/index.php?title=George_U._Yuen&action=edit&redlink=1" class="new" title="George U. Yuen (page does not exist)">George U. Yuen</a> and <a href="/w/index.php?title=James_M._Sugihara&action=edit&redlink=1" class="new" title="James M. Sugihara (page does not exist)">James M. Sugihara</a>.<sup id="cite_ref-yuen1961_5-2" class="reference"><a href="#cite_note-yuen1961-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Cyclic_forms">Cyclic forms</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Hexose&action=edit&section=5" title="Edit section: Cyclic forms"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Like most monosaccharides with five or more carbons, each aldohexose or 2-ketohexose also exists in one or more cyclic (closed-chain) forms, derived from the open-chain form by an <a href="/wiki/Intramolecular_reaction" title="Intramolecular reaction">internal rearrangement</a> between the carbonyl group and one of the hydroxyl groups. </p><p>The reaction turns the <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">=O</span> group into a hydroxyl, and the hydroxyl into an <a href="/wiki/Ether_group" class="mw-redirect" title="Ether group">ether bridge</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−O−</span>) between the two carbon atoms, thus creating a ring with one <a href="/wiki/Oxygen" title="Oxygen">oxygen</a> atom and four or five carbons. </p><p>If the cycle has five carbon atoms (six atoms in total), the closed form is called a <a href="/wiki/Pyranose" title="Pyranose">pyranose</a>, after the <a href="/wiki/Ether" title="Ether">cyclic ether</a> <a href="/wiki/Tetrahydropyran" title="Tetrahydropyran">tetrahydropyran</a>, that has the same ring. If the cycle has four carbon atoms (five in total), the form is called <a href="/wiki/Furanose" title="Furanose">furanose</a> after the compound <a href="/wiki/Tetrahydrofuran" title="Tetrahydrofuran">tetrahydrofuran</a>.<sup id="cite_ref-morr1998_4-1" class="reference"><a href="#cite_note-morr1998-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> The conventional numbering of the carbons in the closed form is the same as in the open-chain form. </p><p>If the sugar is an aldohexose, with the carbonyl in position 1, the reaction may involve the hydroxyl on carbon 4 or carbon 5, creating a <a href="/wiki/Hemiacetal" title="Hemiacetal">hemiacetal</a> with five- or six-membered ring, respectively. If the sugar is a 2-ketohexose, it can only involve the hydroxyl in carbon 5, and will create a <a href="/wiki/Hemiketal" class="mw-redirect" title="Hemiketal">hemiketal</a> with a five-membered ring. </p><p>The closure turns the carboxyl carbon into a <a href="/wiki/Stereocenter" title="Stereocenter">chiral center</a>, which may have either of two configurations, depending on the position of the new hydroxyl. Therefore, each hexose in linear form can produce two distinct closed forms, identified by prefixes "α" and "β". </p> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1237032888/mw-parser-output/.tmulti"><div class="thumb tmulti tnone center"><div class="thumbinner multiimageinner" style="width:592px;max-width:592px"><div class="trow"><div class="tsingle" style="width:135px;max-width:135px"><div class="thumbimage" style="height:144px;overflow:hidden"><span typeof="mw:File"><a href="/wiki/File:Alpha-D-Glucopyranose-with-H.png" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b1/Alpha-D-Glucopyranose-with-H.png/133px-Alpha-D-Glucopyranose-with-H.png" decoding="async" width="133" height="144" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b1/Alpha-D-Glucopyranose-with-H.png/200px-Alpha-D-Glucopyranose-with-H.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b1/Alpha-D-Glucopyranose-with-H.png/266px-Alpha-D-Glucopyranose-with-H.png 2x" data-file-width="946" data-file-height="1024" /></a></span></div><div class="thumbcaption">α-<span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">D</span></span>-Glucopyranose.</div></div><div class="tsingle" style="width:135px;max-width:135px"><div class="thumbimage" style="height:144px;overflow:hidden"><span typeof="mw:File"><a href="/wiki/File:Beta-D-Glucopyranose-with-H.png" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/1/19/Beta-D-Glucopyranose-with-H.png/133px-Beta-D-Glucopyranose-with-H.png" decoding="async" width="133" height="144" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/19/Beta-D-Glucopyranose-with-H.png/200px-Beta-D-Glucopyranose-with-H.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/19/Beta-D-Glucopyranose-with-H.png/266px-Beta-D-Glucopyranose-with-H.png 2x" data-file-width="946" data-file-height="1024" /></a></span></div><div class="thumbcaption">β-<span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">D</span></span>-Glucopyranose.</div></div><div class="tsingle" style="width:157px;max-width:157px"><div class="thumbimage" style="height:144px;overflow:hidden"><span typeof="mw:File"><a href="/wiki/File:Alpha-D-Fructofuranose-with-H.png" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/63/Alpha-D-Fructofuranose-with-H.png/155px-Alpha-D-Fructofuranose-with-H.png" decoding="async" width="155" height="144" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/63/Alpha-D-Fructofuranose-with-H.png/233px-Alpha-D-Fructofuranose-with-H.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/63/Alpha-D-Fructofuranose-with-H.png/310px-Alpha-D-Fructofuranose-with-H.png 2x" data-file-width="1099" data-file-height="1024" /></a></span></div><div class="thumbcaption">α-<span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">D</span></span>-Fructofuranose.</div></div><div class="tsingle" style="width:157px;max-width:157px"><div class="thumbimage" style="height:144px;overflow:hidden"><span typeof="mw:File"><a href="/wiki/File:Beta-D-Fructofuranose-with-H.png" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/9/99/Beta-D-Fructofuranose-with-H.png/155px-Beta-D-Fructofuranose-with-H.png" decoding="async" width="155" height="144" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/99/Beta-D-Fructofuranose-with-H.png/233px-Beta-D-Fructofuranose-with-H.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/99/Beta-D-Fructofuranose-with-H.png/310px-Beta-D-Fructofuranose-with-H.png 2x" data-file-width="1099" data-file-height="1024" /></a></span></div><div class="thumbcaption">β-<span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">D</span></span>-Fructofuranose.</div></div></div><div class="trow" style="display:flex"><div class="thumbcaption">Closed forms of <span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">D</span></span>-glucose and <span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">D</span></span>-fructose, in the <a href="/wiki/Haworth_projection" title="Haworth projection">Haworth projection</a>.</div></div></div></div> <p>It has been known since 1926 that hexoses in the crystalline solid state assume the cyclic form. The "α" and "β" forms, which are not enantiomers, will usually crystallize separately as distinct species. For example, <span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">D</span></span>-glucose forms an α crystal that has <a href="/wiki/Specific_rotation" title="Specific rotation">specific rotation</a> of +112° and melting point of 146 °C, as well as a β crystal that has specific rotation of +19° and melting point of 150 °C.<sup id="cite_ref-morr1998_4-2" class="reference"><a href="#cite_note-morr1998-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p><p>The linear form does not crystallize, and exists only in small amounts in water solutions, where it is in equilibrium with the closed forms.<sup id="cite_ref-morr1998_4-3" class="reference"><a href="#cite_note-morr1998-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> Nevertheless, it plays an essential role as the intermediate stage between those closed forms. </p><p>In particular, the "α" and "β" forms can convert to into each other by returning to the open-chain form and then closing in the opposite configuration. This process is called <a href="/wiki/Mutarotation" title="Mutarotation">mutarotation</a>. </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=Hexose&action=edit&section=6" title="Edit section: Chemical properties"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Although all hexoses have similar structures and share some general properties, each enantiomer pair has its own chemistry. Fructose is soluble in water, alcohol, and ether.<sup id="cite_ref-pub-fructose_9-1" class="reference"><a href="#cite_note-pub-fructose-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> The two enantiomers of each pair generally have vastly different biological properties. </p><p>2-Ketohexoses are stable over a wide pH range, and with a primary p<i>K</i><sub>a</sub> of 10.28, will only deprotonate at high pH, so are marginally less stable than <a href="/wiki/Aldohexose" class="mw-redirect" title="Aldohexose">aldohexoses</a> in solution. </p> <div class="mw-heading mw-heading2"><h2 id="Natural_occurrence_and_uses">Natural occurrence and uses</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Hexose&action=edit&section=7" title="Edit section: Natural occurrence and uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The aldohexose that is most important in biochemistry is <span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">D</span></span>-<a href="/wiki/Glucose" title="Glucose">glucose</a>, which is the main "fuel" for metabolism in many living organisms. </p><p>The 2-ketohexoses <a href="/wiki/Psicose" title="Psicose">psicose</a>, <a href="/wiki/Fructose" title="Fructose">fructose</a> and <a href="/wiki/Tagatose" title="Tagatose">tagatose</a> occur naturally as the <span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">D</span></span>-isomers, whereas <a href="/wiki/Sorbose" title="Sorbose">sorbose</a> occurs naturally as the <span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">L</span></span>-isomer. </p><p><span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">D</span></span>-Sorbose is commonly used in the commercial synthesis of <a href="/wiki/Ascorbic_acid_(molecular_aspects)" class="mw-redirect" title="Ascorbic acid (molecular aspects)">ascorbic acid.</a><sup id="cite_ref-pub-sorbose_10-1" class="reference"><a href="#cite_note-pub-sorbose-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> <span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">D</span></span>-Tagatose is a rare natural ketohexose that is found in small quantities in food.<sup id="cite_ref-pub-tagatose_11-1" class="reference"><a href="#cite_note-pub-tagatose-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> <span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">D</span></span>-<a href="/wiki/Fructose" title="Fructose">Fructose</a> is responsible for the sweet taste of many fruits, and is a building block of <a href="/wiki/Sucrose" title="Sucrose">sucrose</a>, the common sugar. </p> <div class="mw-heading mw-heading2"><h2 id="Deoxyhexoses">Deoxyhexoses</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Hexose&action=edit&section=8" title="Edit section: Deoxyhexoses"><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/Deoxy_sugar" title="Deoxy sugar">Deoxy sugar</a></div> <p>The term "hexose" may sometimes be used to include the deoxyhexoses, which have one or more <a href="/wiki/Hydroxyl_group" class="mw-redirect" title="Hydroxyl group">hydroxyls</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−OH</span>) replaced by <a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a> atoms (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−H</span>). It is named as the parent hexose, with the prefix "<i>x</i>-deoxy-", the <i>x</i> indicating the carbon with the affected hydroxyl. Some examples of biological interest are </p> <ul><li><a href="/wiki/Fucose" title="Fucose"><span style="font-size:85%;">L</span>-Fucose</a> (6-deoxy-<span style="font-size:85%;">L</span>-galactose)</li> <li><a href="/wiki/Rhamnose" title="Rhamnose"><span style="font-size:85%;">L</span>-Rhamnose</a> (6-deoxy-<span style="font-size:85%;">L</span>-mannose)</li> <li><a href="/w/index.php?title=Quinovose&action=edit&redlink=1" class="new" title="Quinovose (page does not exist)"><span style="font-size:85%;">D</span>-Quinovose</a> (6-deoxy-<span style="font-size:85%;">D</span>-glucose), found as part of the <a href="/wiki/Sulfolipid" title="Sulfolipid">sulfolipid</a> <a href="/wiki/Sulfoquinovosyl_diacylglycerol" title="Sulfoquinovosyl diacylglycerol">sulfoquinovosyl diacylglycerol</a> (SQDG)</li> <li><a href="/w/index.php?title=Pneumose&action=edit&redlink=1" class="new" title="Pneumose (page does not exist)"><span style="font-size:85%;">L</span>-Pneumose</a> (6-deoxy-<span style="font-size:85%;">L</span>-talose)</li> <li><a href="/wiki/Fuculose" title="Fuculose"><span style="font-size:85%;">L</span>-Fuculose</a> (6-deoxy-<span style="font-size:85%;">L</span>-tagatose)</li></ul> <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=Hexose&action=edit&section=9" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Diose" title="Diose">Diose</a></li> <li><a href="/wiki/Triose" title="Triose">Triose</a></li> <li><a href="/wiki/Tetrose" title="Tetrose">Tetrose</a></li> <li><a href="/wiki/Pentose" title="Pentose">Pentose</a></li> <li><a href="/wiki/Heptose" title="Heptose">Heptose</a></li> <li><a href="/wiki/Octose" title="Octose">Octose</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=Hexose&action=edit&section=10" 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-lind2007-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-lind2007_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-lind2007_1-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-lind2007_1-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-lind2007_1-3"><sup><i><b>d</b></i></sup></a></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 id="CITEREFThisbe_K._Lindhorst2007" class="citation book cs1"><a href="/wiki/Thisbe_Lindhorst" title="Thisbe 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Lindhorst</a> (2007). <i>Essentials of Carbohydrate Chemistry and Biochemistry</i> (1 ed.). 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Retrieved <span class="nowrap">2018-04-26</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=pubchem.ncbi.nlm.nih.gov&rft.atitle=%3Csmall%3ED%3C%2Fsmall%3E-Psicose&rft.au=Pubchem&rft_id=https%3A%2F%2Fpubchem.ncbi.nlm.nih.gov%2Fcompound%2FD-Psicose%23section%3DNames-and-Identifiers&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHexose" class="Z3988"></span></span> </li> <li id="cite_note-morr1998-4"><span class="mw-cite-backlink">^ <a href="#cite_ref-morr1998_4-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-morr1998_4-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-morr1998_4-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-morr1998_4-3"><sup><i><b>d</b></i></sup></a></span> <span class="reference-text">Robert Thornton Morrison and Robert Neilson Boyd (1998): <i>Organic Chemistry</i>, 6th edition. <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780138924645" title="Special:BookSources/9780138924645">9780138924645</a></span> </li> <li id="cite_note-yuen1961-5"><span class="mw-cite-backlink">^ <a href="#cite_ref-yuen1961_5-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-yuen1961_5-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-yuen1961_5-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text">George U. Yuen and James M. Sugihara (1961): "". <i>Journal of Organic Chemistry</i>, volume 26, issue 5, pages 1598-1601. <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><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%2Fjo01064a070">10.1021/jo01064a070</a></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"><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 patent" id="CITEREFStack;_Robert_J.1990"><a rel="nofollow" class="external text" href="https://worldwide.espacenet.com/textdoc?DB=EPODOC&IDX=US4966845">US patent 4966845</a>, Stack; Robert J., "Microbial production of <span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">L</span></span>-altrose", issued 1990-10-30,  assigned to Government of the United States of America, Secretary of Agriculture</span><span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Apatent&rft.number=4966845&rft.cc=US&rft.title=Microbial+production+of+%3Cspan+class%3D%22smallcaps%22%3E%3Cspan+style%3D%22font-variant%3A+small-caps%3B+text-transform%3A+lowercase%3B%22%3EL%3C%2Fspan%3E%3C%2Fspan%3E-altrose&rft.inventor=Stack%3B+Robert+J.&rft.assignee=Government+of+the+United+States+of+America%2C+Secretary+of+Agriculture&rft.date=1990-10-30"><span style="display: none;"> </span></span></span> </li> <li id="cite_note-orch1980-7"><span class="mw-cite-backlink"><b><a href="#cite_ref-orch1980_7-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMilton_Orchin1980" class="citation book cs1">Milton Orchin, ed. 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Wiley. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-471-04491-8" title="Special:BookSources/978-0-471-04491-8"><bdi>978-0-471-04491-8</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+vocabulary+of+organic+chemistry&rft.pub=Wiley&rft.date=1980&rft.isbn=978-0-471-04491-8&rft_id=https%3A%2F%2Farchive.org%2Fdetails%2Fvocabularyoforga0000unse&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHexose" class="Z3988"></span></span> </li> <li id="cite_note-pub-D-psicose-8"><span class="mw-cite-backlink"><b><a href="#cite_ref-pub-D-psicose_8-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPubchem" class="citation web cs1">Pubchem. <a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/D-Psicose#section=Names-and-Identifiers">"<span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">D</span></span>-Psicose"</a>. <i>pubchem.ncbi.nlm.nih.gov</i><span class="reference-accessdate">. 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Retrieved <span class="nowrap">2018-04-26</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=pubchem.ncbi.nlm.nih.gov&rft.atitle=Sorbose%2C+%3Cspan+class%3D%22smallcaps%22%3E%3Cspan+style%3D%22font-variant%3A+small-caps%3B+text-transform%3A+lowercase%3B%22%3ED%3C%2Fspan%3E%3C%2Fspan%3E-&rft.au=Pubchem&rft_id=https%3A%2F%2Fpubchem.ncbi.nlm.nih.gov%2Fcompound%2F107428%23section%3DTop&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHexose" class="Z3988"></span></span> </li> <li id="cite_note-pub-tagatose-11"><span class="mw-cite-backlink">^ <a href="#cite_ref-pub-tagatose_11-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-pub-tagatose_11-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPubchem" class="citation web cs1">Pubchem. <a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/92092#section=Top">"Tagatose"</a>. <i>pubchem.ncbi.nlm.nih.gov</i><span class="reference-accessdate">. Retrieved <span class="nowrap">2018-04-26</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=pubchem.ncbi.nlm.nih.gov&rft.atitle=Tagatose&rft.au=Pubchem&rft_id=https%3A%2F%2Fpubchem.ncbi.nlm.nih.gov%2Fcompound%2F92092%23section%3DTop&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHexose" class="Z3988"></span></span> </li> <li id="cite_note-bruyn1897-12"><span class="mw-cite-backlink"><b><a href="#cite_ref-bruyn1897_12-0">^</a></b></span> <span class="reference-text">C. A. Lobry de Bruyn and W. Alberda van Ekenstein (1897): "Action des alcalis sur les sucres. VI: La glutose et la pseudo‐fructose". <i>Recueil des Travaux Chimiques des Pays-Bas et de la Belgique</i>, volume 16, issue 9, pages 274-281. <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Frecl.18970160903">10.1002/recl.18970160903</a></span> </li> <li id="cite_note-clark1949-13"><span class="mw-cite-backlink">^ <a href="#cite_ref-clark1949_13-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-clark1949_13-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text">George L. Clark, Hung Kao, Louis Sattler, and F. W. Zerban (1949): "Chemical Nature of Glutose". <i>Industrial & Engineering Chemistry</i>, volume 41, issue 3, pages 530-533. <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><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%2Fie50471a020">10.1021/ie50471a020</a></span> </li> <li id="cite_note-sera1962-14"><span class="mw-cite-backlink"><b><a href="#cite_ref-sera1962_14-0">^</a></b></span> <span class="reference-text">Akira Sera (1962): "Studies on the Chemical Decomposition of Simple Sugars. XIII. Separation of the So-called Glutose (a 3-Ketohexose)". <i>Bulletin of the Chemical Society of Japan</i>, volume 35, issue 12, pages 2031-2033. <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1246%2Fbcsj.35.2031">10.1246/bcsj.35.2031</a></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=Hexose&action=edit&section=11" 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 href="/wiki/File:Commons-logo.svg" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/12px-Commons-logo.svg.png" decoding="async" width="12" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/18px-Commons-logo.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/24px-Commons-logo.svg.png 2x" data-file-width="1024" data-file-height="1376" /></a></span> Media related to <a href="https://commons.wikimedia.org/wiki/Category:Aldohexoses" class="extiw" title="commons:Category:Aldohexoses">Aldohexoses</a> at Wikimedia Commons</li> <li><span class="noviewer" typeof="mw:File"><a href="/wiki/File:Commons-logo.svg" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/12px-Commons-logo.svg.png" decoding="async" width="12" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/18px-Commons-logo.svg.png 1.5x, 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.navbox-abovebelow,.mw-parser-output .navbox-group,.mw-parser-output .navbox-subgroup .navbox-title{background-color:#ddf}.mw-parser-output .navbox-subgroup .navbox-group,.mw-parser-output .navbox-subgroup .navbox-abovebelow{background-color:#e6e6ff}.mw-parser-output .navbox-even{background-color:#f7f7f7}.mw-parser-output .navbox-odd{background-color:transparent}.mw-parser-output .navbox .hlist td dl,.mw-parser-output .navbox .hlist td ol,.mw-parser-output .navbox .hlist td ul,.mw-parser-output .navbox td.hlist dl,.mw-parser-output .navbox td.hlist ol,.mw-parser-output .navbox td.hlist ul{padding:0.125em 0}.mw-parser-output .navbox .navbar{display:block;font-size:100%}.mw-parser-output .navbox-title .navbar{float:left;text-align:left;margin-right:0.5em}body.skin--responsive .mw-parser-output .navbox-image img{max-width:none!important}@media print{body.ns-0 .mw-parser-output .navbox{display:none!important}}</style></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"><style data-mw-deduplicate="TemplateStyles:r1239400231">.mw-parser-output .navbar{display:inline;font-size:88%;font-weight:normal}.mw-parser-output .navbar-collapse{float:left;text-align:left}.mw-parser-output .navbar-boxtext{word-spacing:0}.mw-parser-output .navbar ul{display:inline-block;white-space:nowrap;line-height:inherit}.mw-parser-output .navbar-brackets::before{margin-right:-0.125em;content:"[ "}.mw-parser-output .navbar-brackets::after{margin-left:-0.125em;content:" ]"}.mw-parser-output .navbar li{word-spacing:-0.125em}.mw-parser-output .navbar a>span,.mw-parser-output .navbar a>abbr{text-decoration:inherit}.mw-parser-output .navbar-mini abbr{font-variant:small-caps;border-bottom:none;text-decoration:none;cursor:inherit}.mw-parser-output .navbar-ct-full{font-size:114%;margin:0 7em}.mw-parser-output .navbar-ct-mini{font-size:114%;margin:0 4em}html.skin-theme-clientpref-night .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}@media(prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}}@media print{.mw-parser-output .navbar{display:none!important}}</style><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 class="mw-selflink selflink">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 href="/wiki/Fructose" title="Fructose">Fructose</a></li> <li><a href="/wiki/Psicose" title="Psicose">Psicose</a></li> <li><a href="/wiki/Sorbose" title="Sorbose">Sorbose</a></li> <li><a href="/wiki/Tagatose" title="Tagatose">Tagatose</a></li></ul></li> <li>Deoxy sugars <ul><li><a href="/wiki/Fucose" title="Fucose">Fucose</a></li> <li><a href="/wiki/Fuculose" title="Fuculose">Fuculose</a></li> <li><a href="/wiki/Rhamnose" title="Rhamnose">Rhamnose</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Heptose" title="Heptose">Heptoses</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Ketoheptoses <ul><li><a href="/wiki/Mannoheptulose" title="Mannoheptulose">Mannoheptulose</a></li> <li><a href="/wiki/Sedoheptulose" title="Sedoheptulose">Sedoheptulose</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Above 7</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Octose" title="Octose">Octoses</a></li> <li><a href="/wiki/Nonose" title="Nonose">Nonoses</a> <ul><li><a href="/wiki/Neuraminic_acid" title="Neuraminic acid">Neuraminic acid</a></li></ul></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Multiple</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Disaccharide" title="Disaccharide">Disaccharides</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cellobiose" title="Cellobiose">Cellobiose</a></li> <li><a href="/wiki/Isomaltose" title="Isomaltose">Isomaltose</a></li> <li><a href="/wiki/Isomaltulose" title="Isomaltulose">Isomaltulose</a></li> <li><a href="/wiki/Lactose" title="Lactose">Lactose</a></li> <li><a href="/wiki/Lactulose" title="Lactulose">Lactulose</a></li> <li><a href="/wiki/Maltose" title="Maltose">Maltose</a></li> <li><a href="/wiki/Sucrose" title="Sucrose">Sucrose</a></li> <li><a href="/wiki/Trehalose" title="Trehalose">Trehalose</a></li> <li><a href="/wiki/Turanose" title="Turanose">Turanose</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Trisaccharide" title="Trisaccharide">Trisaccharides</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Maltotriose" title="Maltotriose">Maltotriose</a></li> <li><a href="/wiki/Melezitose" title="Melezitose">Melezitose</a></li> <li><a href="/wiki/Raffinose" title="Raffinose">Raffinose</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Tetrasaccharide" title="Tetrasaccharide">Tetrasaccharides</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Stachyose" title="Stachyose">Stachyose</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other<br /> <a href="/wiki/Oligosaccharide" title="Oligosaccharide">oligosaccharides</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acarbose" title="Acarbose">Acarbose</a></li> <li><a href="/wiki/Fructooligosaccharide" title="Fructooligosaccharide">Fructooligosaccharide</a> (FOS)</li> <li><a href="/wiki/Galactooligosaccharide" title="Galactooligosaccharide">Galactooligosaccharide</a> (GOS)</li> <li><a href="/wiki/Isomaltooligosaccharide" title="Isomaltooligosaccharide">Isomaltooligosaccharide</a> (IMO)</li> <li><a href="/wiki/Maltodextrin" title="Maltodextrin">Maltodextrin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Polysaccharide" title="Polysaccharide">Polysaccharides</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Beta-glucan" title="Beta-glucan">Beta-glucan</a> <ul><li><a href="/wiki/Oat_beta-glucan" title="Oat beta-glucan">Oat beta-glucan</a></li> <li><a href="/wiki/Lentinan" title="Lentinan">Lentinan</a></li> <li><a href="/wiki/Schizophyllan" title="Schizophyllan">Sizofiran</a></li> <li><a href="/wiki/Zymosan" title="Zymosan">Zymosan</a></li> <li><a href="/wiki/Cellulose" title="Cellulose">Cellulose</a></li> <li><a href="/wiki/Chitin" title="Chitin">Chitin</a></li></ul></li> <li><a href="/wiki/Chitosan" title="Chitosan">Chitosan</a></li> <li><a href="/wiki/Dextrin" title="Dextrin">Dextrin</a> / <a href="/wiki/Dextran" title="Dextran">Dextran</a></li> <li><i><a href="/wiki/Fructose" title="Fructose">Fructose</a> / <a href="/wiki/Fructan" title="Fructan">Fructan</a></i> <ul><li><a href="/wiki/Inulin" title="Inulin">Inulin</a></li></ul></li> <li><i><a href="/wiki/Galactose" title="Galactose">Galactose</a> / <a href="/wiki/Galactose" title="Galactose">Galactan</a></i></li> <li><i><a 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> 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