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Xylose - Wikipedia

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class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Human_consumption"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.2</span> <span>Human consumption</span> </div> </a> <ul id="toc-Human_consumption-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Animal_medicine" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Animal_medicine"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.3</span> <span>Animal medicine</span> </div> </a> <ul id="toc-Animal_medicine-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Derivatives" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Derivatives"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.4</span> <span>Derivatives</span> </div> </a> <ul id="toc-Derivatives-sublist" class="vector-toc-list"> </ul> </li> </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">4</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">5</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" 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Available in 41 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-41" 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">41 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/Houtsuiker" title="Houtsuiker – Afrikaans" lang="af" hreflang="af" data-title="Houtsuiker" data-language-autonym="Afrikaans" data-language-local-name="Afrikaans" class="interlanguage-link-target"><span>Afrikaans</span></a></li><li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%B2%D9%8A%D9%84%D9%88%D8%B2" title="زيلوز – Arabic" lang="ar" hreflang="ar" data-title="زيلوز" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D9%82%D8%B2%DB%8C%D9%84%D9%88%D8%B2" title="قزیلوز – South Azerbaijani" lang="azb" hreflang="azb" data-title="قزیلوز" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-bn mw-list-item"><a href="https://bn.wikipedia.org/wiki/%E0%A6%9C%E0%A6%BE%E0%A6%87%E0%A6%B2%E0%A7%8B%E0%A6%9C" title="জাইলোজ – Bangla" lang="bn" hreflang="bn" data-title="জাইলোজ" 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%9A%D1%81%D1%96%D0%BB%D0%BE%D0%B7%D0%B0" title="Ксілоза – Belarusian" lang="be" hreflang="be" data-title="Ксілоза" 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%9A%D1%81%D1%8B%D0%BB%D1%91%D0%B7%D0%B0" title="Ксылёза – Belarusian (Taraškievica orthography)" lang="be-tarask" hreflang="be-tarask" data-title="Ксылёза" 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%9A%D1%81%D0%B8%D0%BB%D0%BE%D0%B7%D0%B0" title="Ксилоза – Bulgarian" lang="bg" hreflang="bg" data-title="Ксилоза" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target"><span>Български</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Xilosa" title="Xilosa – Catalan" lang="ca" hreflang="ca" data-title="Xilosa" 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/Xyl%C3%B3za" title="Xylóza – Czech" lang="cs" hreflang="cs" data-title="Xylóza" 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/Xylose" title="Xylose – Danish" lang="da" hreflang="da" data-title="Xylose" 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/Xylose" title="Xylose – German" lang="de" hreflang="de" data-title="Xylose" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%9E%CF%85%CE%BB%CF%8C%CE%B6%CE%B7" title="Ξυλόζη – Greek" lang="el" hreflang="el" data-title="Ξυλόζη" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target"><span>Ελληνικά</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Xilosa" title="Xilosa – Spanish" lang="es" hreflang="es" data-title="Xilosa" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Xilosa" title="Xilosa – Basque" lang="eu" hreflang="eu" data-title="Xilosa" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%DA%AF%D8%B2%DB%8C%D9%84%D9%88%D8%B2" title="گزیلوز – Persian" lang="fa" hreflang="fa" data-title="گزیلوز" 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/Xylose" title="Xylose – French" lang="fr" hreflang="fr" data-title="Xylose" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-fy mw-list-item"><a href="https://fy.wikipedia.org/wiki/Ksyloaze" title="Ksyloaze – Western Frisian" lang="fy" hreflang="fy" data-title="Ksyloaze" data-language-autonym="Frysk" data-language-local-name="Western Frisian" class="interlanguage-link-target"><span>Frysk</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Xilosa" title="Xilosa – Galician" lang="gl" hreflang="gl" data-title="Xilosa" 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%9E%90%EC%9D%BC%EB%A1%9C%EC%8A%A4" title="자일로스 – Korean" lang="ko" hreflang="ko" data-title="자일로스" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Xilosa" title="Xilosa – Indonesian" lang="id" hreflang="id" data-title="Xilosa" 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/D(%2B)-xilosio" title="D(+)-xilosio – Italian" lang="it" hreflang="it" data-title="D(+)-xilosio" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%A7%D7%A1%D7%99%D7%9C%D7%95%D7%96" title="קסילוז – Hebrew" lang="he" hreflang="he" data-title="קסילוז" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-lt mw-list-item"><a href="https://lt.wikipedia.org/wiki/Ksiloz%C4%97" title="Ksilozė – Lithuanian" lang="lt" hreflang="lt" data-title="Ksilozė" data-language-autonym="Lietuvių" data-language-local-name="Lithuanian" class="interlanguage-link-target"><span>Lietuvių</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Xil%C3%B3z" title="Xilóz – Hungarian" lang="hu" hreflang="hu" data-title="Xilóz" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Xylose" title="Xylose – Dutch" lang="nl" hreflang="nl" data-title="Xylose" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%AD%E3%82%B7%E3%83%AD%E3%83%BC%E3%82%B9" title="キシロース – Japanese" lang="ja" hreflang="ja" data-title="キシロース" 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-nn mw-list-item"><a href="https://nn.wikipedia.org/wiki/Xylose" title="Xylose – Norwegian Nynorsk" lang="nn" hreflang="nn" data-title="Xylose" data-language-autonym="Norsk nynorsk" data-language-local-name="Norwegian Nynorsk" class="interlanguage-link-target"><span>Norsk nynorsk</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Ksyloza" title="Ksyloza – Polish" lang="pl" hreflang="pl" data-title="Ksyloza" 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/Xilose" title="Xilose – Portuguese" lang="pt" hreflang="pt" data-title="Xilose" 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/Xiloz%C4%83" title="Xiloză – Romanian" lang="ro" hreflang="ro" data-title="Xiloză" 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%9A%D1%81%D0%B8%D0%BB%D0%BE%D0%B7%D0%B0" title="Ксилоза – Russian" lang="ru" hreflang="ru" data-title="Ксилоза" 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/Xyl%C3%B3za" title="Xylóza – Slovak" lang="sk" hreflang="sk" data-title="Xylóza" 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/Ksiloza" title="Ksiloza – Serbian" lang="sr" hreflang="sr" data-title="Ksiloza" 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/Ksiloza" title="Ksiloza – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Ksiloza" 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/Ksyloosi" title="Ksyloosi – Finnish" lang="fi" hreflang="fi" data-title="Ksyloosi" 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/Xylos" title="Xylos – Swedish" lang="sv" hreflang="sv" data-title="Xylos" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%9A%E0%AF%88%E0%AE%B2%E0%AF%8B%E0%AE%9A%E0%AF%81" title="சைலோசு – Tamil" lang="ta" hreflang="ta" data-title="சைலோசு" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-chr mw-list-item"><a href="https://chr.wikipedia.org/wiki/%E1%8E%B6%E1%8F%8E%E1%8E%A2" title="ᎶᏎᎢ – Cherokee" lang="chr" hreflang="chr" data-title="ᎶᏎᎢ" data-language-autonym="ᏣᎳᎩ" data-language-local-name="Cherokee" class="interlanguage-link-target"><span>ᏣᎳᎩ</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Ksiloz" title="Ksiloz – Turkish" lang="tr" hreflang="tr" data-title="Ksiloz" 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%9A%D1%81%D0%B8%D0%BB%D0%BE%D0%B7%D0%B0" title="Ксилоза – Ukrainian" lang="uk" hreflang="uk" data-title="Ксилоза" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E6%9C%A8%E7%B3%96" title="木糖 – Chinese" lang="zh" hreflang="zh" data-title="木糖" data-language-autonym="中文" data-language-local-name="Chinese" 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data-pinnable-element-id="vector-appearance" data-pinned-container-id="vector-appearance-pinned-container" data-unpinned-container-id="vector-appearance-unpinned-container" > <div class="vector-pinnable-header-label">Appearance</div> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-appearance.pin">move to sidebar</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-appearance.unpin">hide</button> </div> </div> </div> </nav> </div> </div> <div id="bodyContent" class="vector-body" aria-labelledby="firstHeading" data-mw-ve-target-container> <div class="vector-body-before-content"> <div class="mw-indicators"> </div> <div id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Sugar</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">"Wood sugar" redirects here. For the related sugar alcohol, see <a href="/wiki/Xylitol" title="Xylitol">Xylitol</a>.</div> <style data-mw-deduplicate="TemplateStyles:r1084375498">.mw-parser-output .ib-chembox{border-collapse:collapse;text-align:left}.mw-parser-output .ib-chembox td,.mw-parser-output .ib-chembox th{border:1px solid #a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}</style> <table class="infobox ib-chembox"> <caption><style data-mw-deduplicate="TemplateStyles:r920966791">.mw-parser-output span.smallcaps{font-variant:small-caps}.mw-parser-output span.smallcaps-smaller{font-size:85%}</style><span class="smallcaps">d</span>-Xylose </caption> <tbody><tr> <td colspan="2" class="borderless" style="text-align:center"> <table border="0" style="width:100%;display:inline-table;"> <tbody><tr> <td style="border-right:1px solid #aaa; width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Xylose.svg" class="mw-file-description" title="D-Xylopyranose"><img alt="D-Xylopyranose" src="//upload.wikimedia.org/wikipedia/commons/thumb/9/9e/Xylose.svg/110px-Xylose.svg.png" decoding="async" width="110" height="84" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/9e/Xylose.svg/165px-Xylose.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/9e/Xylose.svg/220px-Xylose.svg.png 2x" data-file-width="315" data-file-height="241" /></a><figcaption>D-Xylopyranose</figcaption></figure> </td> <td style="width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Xylofuranose.png" class="mw-file-description" title="Xylofuranose"><img alt="Xylofuranose" src="//upload.wikimedia.org/wikipedia/commons/thumb/7/78/Xylofuranose.png/130px-Xylofuranose.png" decoding="async" width="130" height="65" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/78/Xylofuranose.png/195px-Xylofuranose.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/78/Xylofuranose.png/260px-Xylofuranose.png 2x" data-file-width="665" data-file-height="335" /></a><figcaption>Xylofuranose</figcaption></figure> </td></tr></tbody></table> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:D-Xylose.svg" class="mw-file-description" title="Xylose chair"><img alt="Xylose chair" src="//upload.wikimedia.org/wikipedia/commons/thumb/5/58/D-Xylose.svg/180px-D-Xylose.svg.png" decoding="async" width="180" height="71" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/58/D-Xylose.svg/270px-D-Xylose.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/58/D-Xylose.svg/360px-D-Xylose.svg.png 2x" data-file-width="620" data-file-height="245" /></a></span> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Xylose_linear.png" class="mw-file-description" title="Xylose linear"><img alt="Xylose linear" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c0/Xylose_linear.png/180px-Xylose_linear.png" decoding="async" width="180" height="89" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c0/Xylose_linear.png/270px-Xylose_linear.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c0/Xylose_linear.png/360px-Xylose_linear.png 2x" data-file-width="1128" data-file-height="557" /></a></span> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Chemical_nomenclature" title="Chemical nomenclature">IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-Xylose</div> </td></tr> <tr> <td colspan="2" style="text-align:left;">Other names <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">(+)-Xylose<br />Wood sugar</div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=58-86-6">58-86-6</a></span><sup>&#160;<span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=609-06-3">609-06-3</a></span>&#x20;(<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">l</span>-isomer)<sup>&#160;<span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span>&#91;<a href="/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validation" title="Wikipedia:WikiProject Chemicals/Chembox validation">ESIS</a>&#93;</sup></li><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=41247-05-6">41247-05-6</a></span>&#x20;(racemate)<sup>&#160;<span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span>&#91;<a href="/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validation" title="Wikipedia:WikiProject Chemicals/Chembox validation">ESIS</a>&#93;</sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=C1%5BC%40H%5D%28%5BC%40%40H%5D%28%5BC%40H%5D%28C%28O1%29O%29O%29O%29O">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembldb/index.php/compound/inspect/ChEMBL502135">ChEMBL502135</a></span><sup>&#160;<span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.119104.html">119104</a></span><sup>&#160;<span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a> </td> <td><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.043.072">100.043.072</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q66589603#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span> </td></tr> <tr> <td><a href="/wiki/European_Community_number" title="European Community number"><span title="European Community number (chemical identifier)">EC Number</span></a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>200-400-7</li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/135191">135191</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/A1TA934AKO">A1TA934AKO</a></span><sup>&#160;<span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/A4JW0V2MYA">A4JW0V2MYA</a></span>&#160;(<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">l</span>-isomer)<sup>&#160;<span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/C5H10O5/c6-2-1-10-5(9)4(8)3(2)7/h2-9H,1H2/t2-,3+,4-,5?/m1/s1<sup>&#160;<span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup></div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key:&#160;SRBFZHDQGSBBOR-IOVATXLUSA-N<sup>&#160;<span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup></div></div></li><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1/C5H10O5/c6-2-1-10-5(9)4(8)3(2)7/h2-9H,1H2/t2-,3+,4-,5?/m1/s1</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key:&#160;SRBFZHDQGSBBOR-IOVATXLUBL</div></div></li></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">C1[C@H]([C@@H]([C@H](C(O1)O)O)O)O</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Properties<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">&#91;</span>1<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">&#91;</span>2<span class="cite-bracket">&#93;</span></a></sup> </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td><span class="chemf nowrap">C<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">5</sub></span></span>H<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">10</sub></span></span>O<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">5</sub></span></span></span>&#x20; </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td>150.13 g/mol&#x20; &#x20; </td></tr> <tr> <td>Appearance </td> <td>monoclinic needles or prisms, colourless </td></tr> <tr> <td><a href="/wiki/Density" title="Density">Density</a> </td> <td>1.525 g/cm<sup>3</sup> (20&#160;°C) </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>144 to 145&#160;°C (291 to 293&#160;°F; 417 to 418&#160;K) </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Specific_rotation" title="Specific rotation">Chiral rotation</a> ([α]<sub>D</sub>)</div> </td> <td>+22.5° (<span class="chemf nowrap">CHCl<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">3</sub></span></span></span>) </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Magnetic_susceptibility" title="Magnetic susceptibility">Magnetic susceptibility</a> (&#967;)</div> </td> <td>-84.80·10<sup>−6</sup> cm<sup>3</sup>/mol </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Hazards </th></tr> <tr> <td><a href="/wiki/NFPA_704" title="NFPA 704"><b>NFPA 704</b></a> (fire&#160;diamond) </td> <td><style data-mw-deduplicate="TemplateStyles:r1170367383">.mw-parser-output .nfpa-704-diamond-ref{float:right;padding:1px;text-align:right}.mw-parser-output .nfpa-704-diamond-container{width:82px;font-family:sans-serif;margin:0 auto}.mw-parser-output .nfpa-704-diamond-container-ref{float:left;margin-left:1em}.mw-parser-output .nfpa-704-diamond-images{float:left;font-size:20px;text-align:center;position:relative;height:80px;width:80px;padding:1px}.mw-parser-output .nfpa-704-diamond-map{position:absolute;height:80px;width:80px}.mw-parser-output .nfpa-704-diamond .noresize{margin:0 auto}.mw-parser-output .nfpa-704-diamond-code{line-height:1em;text-align:center;position:absolute}.mw-parser-output .nfpa-704-diamond-code>a{color:black}.mw-parser-output .nfpa-704-diamond-blue{width:13px;top:31px;left:15px}.mw-parser-output .nfpa-704-diamond-red{width:12px;top:12px;left:35px}.mw-parser-output .nfpa-704-diamond-yellow{width:13px;top:31px;left:54px}.mw-parser-output .nfpa-704-diamond-white-image{position:relative;top:51px;left:0}.mw-parser-output .nfpa-704-diamond-white-text{vertical-align:middle;text-align:center;line-height:80%;position:absolute;top:52px}.mw-parser-output .nfpa-704-diamond-white-text a>span{position:absolute;color:black}.mw-parser-output .nfpa-704-diamond-white-wors{font-size:15px;width:23px;left:29px}.mw-parser-output .nfpa-704-diamond-white-wox{font-size:15px;font-stretch:condensed;width:21px;line-height:80%;top:-4px;left:29px}.mw-parser-output .nfpa-704-diamond-white-abcp{font-size:13.5px;font-stretch:condensed;width:28px;left:26px}.mw-parser-output .nfpa-704-diamond-white-ac{font-size:10px;width:30px;left:25px}.mw-parser-output .nfpa-704-diamond-white-strike{text-decoration:line-through}</style><div class="nfpa-704-diamond notheme"><div class="nfpa-704-diamond-container"><div class="nfpa-704-diamond-images nounderlines"> <div class="nfpa-704-diamond-map"><figure class="noresize" typeof="mw:File"><span><img alt="NFPA 704 four-colored diamond" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/80px-NFPA_704.svg.png" decoding="async" width="80" height="80" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/120px-NFPA_704.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/160px-NFPA_704.svg.png 2x" data-file-width="512" data-file-height="512" usemap="#ImageMap_811dcee2cbfc5fb2" /></span><map name="ImageMap_811dcee2cbfc5fb2"><area href="/wiki/NFPA_704#Blue" shape="poly" coords="23,23,47,47,23,70,0,47" alt="Health 1: Exposure would cause irritation but only minor residual injury. E.g. turpentine" title="Health 1: Exposure would cause irritation but only minor residual injury. E.g. turpentine" /><area href="/wiki/NFPA_704#Red" shape="poly" coords="47,0,70,23,47,47,23,23" alt="Flammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oil" title="Flammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oil" /><area href="/wiki/NFPA_704#Yellow" shape="poly" coords="70,23,94,47,70,70,47,47" alt="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" title="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" /><area href="/wiki/NFPA_704#White" shape="poly" coords="47,47,70,70,47,94,23,70" alt="Special hazards (white): no code" title="Special hazards (white): no code" /></map><figcaption></figcaption></figure></div><div class="nfpa-704-diamond-code nfpa-704-diamond-blue"> <a href="/wiki/NFPA_704#Blue" title="NFPA 704"><span title="Health 1: Exposure would cause irritation but only minor residual injury. E.g. turpentine" class="notheme mw-no-invert">1</span></a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-red"> <a href="/wiki/NFPA_704#Red" title="NFPA 704"><span title="Flammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oil" class="notheme mw-no-invert">1</span></a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-yellow"> <a href="/wiki/NFPA_704#Yellow" title="NFPA 704"><span title="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" class="notheme mw-no-invert">0</span></a></div></div></div></div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Related compounds </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Related <a href="/wiki/Pentose" title="Pentose">aldopentoses</a></div> </td> <td><a href="/wiki/Arabinose" title="Arabinose">Arabinose</a><br /><a href="/wiki/Ribose" title="Ribose">Ribose</a><br /><a href="/wiki/Lyxose" title="Lyxose">Lyxose</a> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Related compounds</div> </td> <td><a href="/wiki/Xylulose" title="Xylulose">Xylulose</a> </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25&#160;°C [77&#160;°F], 100&#160;kPa).</div> <div style="margin-top: 0.3em;"><div style="text-align:center;"><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/12px-X_mark.svg.png" decoding="async" width="12" height="14" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/18px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/24px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span>&#160;<span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&amp;rev1=458276050&amp;page2=Xylose">verify</a></span>&#160;(<a href="/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validation" title="Wikipedia:WikiProject Chemicals/Chembox validation">what is</a>&#160;<sup><span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup>&#160;?) </div></div> <div style="margin-top: 0.3em; text-align: center;"><a href="/wiki/Wikipedia:Chemical_infobox#References" title="Wikipedia:Chemical infobox">Infobox references</a></div> </td></tr> </tbody></table><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound</div> <p><b>Xylose</b> (<abbr title="compare with">cf.</abbr> <a href="/wiki/Ancient_Greek_language" class="mw-redirect" title="Ancient Greek language">Ancient Greek</a>: <span lang="grc">ξύλον</span>, <span title="Ancient Greek (to 1453)-language romanization"><i lang="grc-Latn">xylon</i></span>, "wood") is a sugar first isolated from wood, and named for it. Xylose is classified as a <a href="/wiki/Monosaccharide" title="Monosaccharide">monosaccharide</a> of the <a href="/wiki/Aldopentose" class="mw-redirect" title="Aldopentose">aldopentose</a> type, which means that it contains five <a href="/wiki/Carbon" title="Carbon">carbon</a> atoms and includes an <a href="/wiki/Aldehyde" title="Aldehyde">aldehyde</a> <a href="/wiki/Functional_group" title="Functional group">functional group</a>. It is derived from <a href="/wiki/Hemicellulose" title="Hemicellulose">hemicellulose</a>, one of the main constituents of <a href="/wiki/Biomass" title="Biomass">biomass</a>. Like most sugars, it can adopt several structures depending on conditions. With its free <a href="/wiki/Aldehyde_group" class="mw-redirect" title="Aldehyde group">aldehyde group</a>, it is a <a href="/wiki/Reducing_sugar" title="Reducing sugar">reducing sugar</a>. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Structure">Structure</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Xylose&amp;action=edit&amp;section=1" title="Edit section: Structure"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The <a href="/wiki/Open_chain_compound" class="mw-redirect" title="Open chain compound">acyclic</a> form of xylose has <a href="/wiki/Chemical_formula" title="Chemical formula">chemical formula</a> <span class="chemf nowrap">HOCH<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2</sub></span></span>(CH(OH))3CHO</span>. The cyclic <a href="/wiki/Hemiacetal" title="Hemiacetal">hemiacetal</a> isomers are more prevalent in solution and are of two types: the <a href="/wiki/Pyranose" title="Pyranose">pyranoses</a>, which feature six-membered <span class="chemf nowrap">C<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">5</sub></span></span>O</span> rings, and the <a href="/wiki/Furanose" title="Furanose">furanoses</a>, which feature five-membered <span class="chemf nowrap">C<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">4</sub></span></span>O</span> rings (with a pendant <span class="chemf nowrap">CH<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2</sub></span></span>OH</span> group). Each of these rings is subject to further isomerism, depending on the relative orientation of the anomeric hydroxy group. </p><p>The <a href="/wiki/Dextrorotation_and_levorotation" class="mw-redirect" title="Dextrorotation and levorotation">dextrorotary</a> form, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>-xylose, is the one that usually occurs <a href="/wiki/Endogeny_(biology)" title="Endogeny (biology)">endogenously</a> in <a href="/wiki/Life" title="Life">living things</a>. A levorotary form, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">l</span>-xylose, can be <a href="/wiki/Organic_synthesis" title="Organic synthesis">synthesized</a>. </p> <div class="mw-heading mw-heading2"><h2 id="Occurrence">Occurrence</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Xylose&amp;action=edit&amp;section=2" title="Edit section: Occurrence"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Xylose is the main building block for the <a href="/wiki/Hemicellulose" title="Hemicellulose">hemicellulose</a> <a href="/wiki/Xylan" title="Xylan">xylan</a>, which comprises about 30% of some plants (birch for example), far less in others (spruce and pine have about 9% xylan). Xylose is otherwise pervasive, being found in the <a href="/wiki/Embryo" title="Embryo">embryos</a> of most edible plants. It was first isolated from wood by Finnish scientist, Koch, in 1881,<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">&#91;</span>3<span class="cite-bracket">&#93;</span></a></sup> but first became commercially viable, with a price close to <a href="/wiki/Sucrose" title="Sucrose">sucrose</a>, in 1930.<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">&#91;</span>4<span class="cite-bracket">&#93;</span></a></sup> </p><p>Xylose is also the first saccharide added to the <a href="/wiki/Serine" title="Serine">serine</a> or <a href="/wiki/Threonine" title="Threonine">threonine</a> in the <a href="/wiki/Proteoglycan" title="Proteoglycan">proteoglycan</a> type <a href="/wiki/O-glycosylation" class="mw-redirect" title="O-glycosylation">O-glycosylation</a>, and, so, it is the first saccharide in biosynthetic pathways of most <a href="/wiki/Anionic" class="mw-redirect" title="Anionic">anionic</a> <a href="/wiki/Polysaccharide" title="Polysaccharide">polysaccharides</a> such as <a href="/wiki/Heparan_sulfate" title="Heparan sulfate">heparan sulfate</a> and <a href="/wiki/Chondroitin_sulfate" title="Chondroitin sulfate">chondroitin sulfate</a>.<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup> </p><p>Xylose is also found in some species of Chrysolinina beetles, including <i>Chrysolina coerulans</i>. They have <a href="/wiki/Cardiac_glycosides" class="mw-redirect" title="Cardiac glycosides">cardiac glycosides</a> (including xylose) in their defensive glands.<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">&#91;</span>6<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Applications">Applications</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Xylose&amp;action=edit&amp;section=3" title="Edit section: Applications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Chemicals">Chemicals</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Xylose&amp;action=edit&amp;section=4" title="Edit section: Chemicals"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The acid-catalysed degradation of hemicellulose gives <a href="/wiki/Furfural" title="Furfural">furfural</a>,<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">&#91;</span>7<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">&#91;</span>8<span class="cite-bracket">&#93;</span></a></sup> a precursor to synthetic polymers and to <a href="/wiki/Tetrahydrofuran" title="Tetrahydrofuran">tetrahydrofuran</a>.<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">&#91;</span>9<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Human_consumption">Human consumption</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Xylose&amp;action=edit&amp;section=5" title="Edit section: Human consumption"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Xylose is metabolised by humans, although it is not a major human nutrient and is largely excreted by the kidneys.<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">&#91;</span>10<span class="cite-bracket">&#93;</span></a></sup> Humans can obtain xylose only from their diet. An <a href="/wiki/Oxidoreductase" title="Oxidoreductase">oxidoreductase</a> pathway is present in <a href="/wiki/Eukaryotic_microorganism" class="mw-redirect" title="Eukaryotic microorganism">eukaryotic microorganisms</a>. Humans have enzymes called <a href="/wiki/Protein_xylosyltransferase" title="Protein xylosyltransferase">protein xylosyltransferases</a> (<a href="/wiki/XYLT1" title="XYLT1">XYLT1</a>, <a href="/wiki/XYLT2" title="XYLT2">XYLT2</a>) which transfer xylose from UDP to a serine in the core protein of proteoglycans. </p><p>Xylose contains 2.4 calories per gram<sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">&#91;</span>11<span class="cite-bracket">&#93;</span></a></sup> (lower than glucose or sucrose, approx. 4 calories per gram). </p> <div class="mw-heading mw-heading3"><h3 id="Animal_medicine">Animal medicine</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Xylose&amp;action=edit&amp;section=6" title="Edit section: Animal medicine"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In animal medicine, <a href="/wiki/D-Xylose_absorption_test" class="mw-redirect" title="D-Xylose absorption test">xylose is used to test</a> for <a href="/wiki/Malabsorption" title="Malabsorption">malabsorption</a> by administration in water to the patient after <a href="/wiki/Fasting" title="Fasting">fasting</a>. If xylose is detected in <a href="/wiki/Blood" title="Blood">blood</a> and/or <a href="/wiki/Urine" title="Urine">urine</a> within the next few hours, it has been absorbed by the intestines.<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">&#91;</span>12<span class="cite-bracket">&#93;</span></a></sup> </p><p>High xylose intake on the order of approximately 100&#160;g/kg of animal body weight is relatively well tolerated in pigs, and in a similar manner to results from human studies, a portion of the xylose intake is passed out in urine undigested.<sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">&#91;</span>13<span class="cite-bracket">&#93;</span></a></sup> </p><p><br /> </p> <div class="mw-heading mw-heading3"><h3 id="Derivatives">Derivatives</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Xylose&amp;action=edit&amp;section=7" title="Edit section: Derivatives"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Organic_redox_reaction" title="Organic redox reaction">Reduction</a> of xylose by catalytic <a href="/wiki/Hydrogenation" title="Hydrogenation">hydrogenation</a> produces the <a href="/wiki/Sugar_substitute" title="Sugar substitute">sugar substitute</a> <a href="/wiki/Xylitol" title="Xylitol">xylitol</a>. </p> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Xylose&amp;action=edit&amp;section=8" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><i><a href="/wiki/Saccharophagus_degradans" class="mw-redirect" title="Saccharophagus degradans">Saccharophagus degradans</a></i></li> <li><a href="/wiki/Xylonic_acid" title="Xylonic acid">Xylonic acid</a></li> <li><a href="/wiki/Xylose_metabolism" title="Xylose metabolism">Xylose metabolism</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=Xylose&amp;action=edit&amp;section=9" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite class="citation cs2"><i><a href="/wiki/Merck_Index" title="Merck Index">The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals</a></i> (11th&#160;ed.), Merck, 1989, <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a>&#160;<a href="/wiki/Special:BookSources/091191028X" title="Special:BookSources/091191028X"><bdi>091191028X</bdi></a></cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=book&amp;rft.btitle=The+Merck+Index%3A+An+Encyclopedia+of+Chemicals%2C+Drugs%2C+and+Biologicals&amp;rft.edition=11th&amp;rft.pub=Merck&amp;rft.date=1989&amp;rft.isbn=091191028X&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AXylose" class="Z3988"></span>,&#32;9995.</span> </li> <li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWeast1981" class="citation book cs1">Weast, Robert C., ed. (1981). <i>CRC Handbook of Chemistry and Physics</i> (62nd&#160;ed.). Boca Raton, FL: CRC Press. p.&#160;C-574. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a>&#160;<a href="/wiki/Special:BookSources/0-8493-0462-8" title="Special:BookSources/0-8493-0462-8"><bdi>0-8493-0462-8</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=book&amp;rft.btitle=CRC+Handbook+of+Chemistry+and+Physics&amp;rft.place=Boca+Raton%2C+FL&amp;rft.pages=C-574&amp;rft.edition=62nd&amp;rft.pub=CRC+Press&amp;rft.date=1981&amp;rft.isbn=0-8493-0462-8&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AXylose" class="Z3988"></span>.</span> </li> <li id="cite_note-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-3">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHudsonCantor2014" class="citation book cs1">Hudson, C.S.; Cantor, S.M., eds. (2014) [1950]. <a rel="nofollow" class="external text" href="https://books.google.com/books?id=rUapoxXf-v4C"><i>Advances in Carbohydrate Chemistry</i></a>. Vol.&#160;5. Elsevier. p.&#160;278. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a>&#160;<a href="/wiki/Special:BookSources/9780080562643" title="Special:BookSources/9780080562643"><bdi>9780080562643</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=book&amp;rft.btitle=Advances+in+Carbohydrate+Chemistry&amp;rft.pages=278&amp;rft.pub=Elsevier&amp;rft.date=2014&amp;rft.isbn=9780080562643&amp;rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DrUapoxXf-v4C&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AXylose" class="Z3988"></span></span> </li> <li id="cite_note-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-4">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMillerLewis1932" class="citation journal cs1">Miller, Mabel M.; Lewis, Howard B. (1932). <a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FS0021-9258%2818%2976145-0">"Pentose Metabolism: I. The Rate of Absorption of d-Xylose and the Formation of Glycogen in the Organism of the White Rat after Oral Administration of d-Xylose"</a>. <i>Journal of Biological Chemistry</i>. <b>98</b> (1): 133–140. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FS0021-9258%2818%2976145-0">10.1016/S0021-9258(18)76145-0</a></span>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=Journal+of+Biological+Chemistry&amp;rft.atitle=Pentose+Metabolism%3A+I.+The+Rate+of+Absorption+of+d-Xylose+and+the+Formation+of+Glycogen+in+the+Organism+of+the+White+Rat+after+Oral+Administration+of+d-Xylose&amp;rft.volume=98&amp;rft.issue=1&amp;rft.pages=133-140&amp;rft.date=1932&amp;rft_id=info%3Adoi%2F10.1016%2FS0021-9258%2818%2976145-0&amp;rft.aulast=Miller&amp;rft.aufirst=Mabel+M.&amp;rft.au=Lewis%2C+Howard+B.&amp;rft_id=https%3A%2F%2Fdoi.org%2F10.1016%252FS0021-9258%252818%252976145-0&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AXylose" class="Z3988"></span></span> </li> <li id="cite_note-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-5">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBuskasIngaleBoons2006" class="citation cs2">Buskas, Therese; Ingale, Sampat; Boons, Geert-Jan (2006), "Glycopeptides as versatile tool for glycobiology", <i>Glycobiology</i>, <b>16</b> (8): 113R–36R, <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1093%2Fglycob%2Fcwj125">10.1093/glycob/cwj125</a></span>, <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a>&#160;<a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/16675547">16675547</a></cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=Glycobiology&amp;rft.atitle=Glycopeptides+as+versatile+tool+for+glycobiology&amp;rft.volume=16&amp;rft.issue=8&amp;rft.pages=113R-36R&amp;rft.date=2006&amp;rft_id=info%3Adoi%2F10.1093%2Fglycob%2Fcwj125&amp;rft_id=info%3Apmid%2F16675547&amp;rft.aulast=Buskas&amp;rft.aufirst=Therese&amp;rft.au=Ingale%2C+Sampat&amp;rft.au=Boons%2C+Geert-Jan&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AXylose" class="Z3988"></span></span> </li> <li id="cite_note-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-6">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMorgan2004" class="citation book cs1">Morgan, E. David (2004). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=AbXid2E-17YC&amp;pg=PA112">"§ 7.3.1 Sterols in Insects"</a>. <i>Biosynthesis in Insects</i>. Royal Society of Chemistry. p.&#160;112. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a>&#160;<a href="/wiki/Special:BookSources/9780854046911" title="Special:BookSources/9780854046911"><bdi>9780854046911</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=bookitem&amp;rft.atitle=%C2%A7+7.3.1+Sterols+in+Insects&amp;rft.btitle=Biosynthesis+in+Insects&amp;rft.pages=112&amp;rft.pub=Royal+Society+of+Chemistry&amp;rft.date=2004&amp;rft.isbn=9780854046911&amp;rft.aulast=Morgan&amp;rft.aufirst=E.+David&amp;rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DAbXid2E-17YC%26pg%3DPA112&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AXylose" class="Z3988"></span></span> </li> <li id="cite_note-7"><span class="mw-cite-backlink"><b><a href="#cite_ref-7">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFAdamsVoorhees1921" class="citation journal cs1">Adams, Roger; Voorhees, V. (1921). <a rel="nofollow" class="external text" href="http://www.orgsyn.org/demo.aspx?prep=cv1p0280">"Furfural"</a>. <i><a href="/wiki/Organic_Syntheses" title="Organic Syntheses">Organic Syntheses</a></i>. <b>1</b>: 49. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.15227%2Forgsyn.001.0049">10.15227/orgsyn.001.0049</a></cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=Organic+Syntheses&amp;rft.atitle=Furfural&amp;rft.volume=1&amp;rft.pages=49&amp;rft.date=1921&amp;rft_id=info%3Adoi%2F10.15227%2Forgsyn.001.0049&amp;rft.aulast=Adams&amp;rft.aufirst=Roger&amp;rft.au=Voorhees%2C+V.&amp;rft_id=http%3A%2F%2Fwww.orgsyn.org%2Fdemo.aspx%3Fprep%3Dcv1p0280&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AXylose" class="Z3988"></span>; <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation cs2"><i>Collected Volumes</i>, vol.&#160;1, p.&#160;280</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=book&amp;rft.btitle=Collected+Volumes&amp;rft.pages=280&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AXylose" class="Z3988"></span>.</span> </li> <li id="cite_note-8"><span class="mw-cite-backlink"><b><a href="#cite_ref-8">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGómez_MillánHellsten,_SannaKing,_Alistair_W.T.Pokki,_Juha-Pekka2019" class="citation journal cs1">Gómez Millán, Gerardo; Hellsten, Sanna; King, Alistair W.T.; Pokki, Juha-Pekka; Llorca, Jordi; Sixta, Herbert (25 April 2019). "A comparative study of water-immiscible organic solvents in the production of furfural from xylose and birch hydrolysate". <i>Journal of Industrial and Engineering Chemistry</i>. <b>72</b>: 354–363. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.jiec.2018.12.037">10.1016/j.jiec.2018.12.037</a>. <a href="/wiki/Hdl_(identifier)" class="mw-redirect" title="Hdl (identifier)">hdl</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://hdl.handle.net/10138%2F307298">10138/307298</a></span>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a>&#160;<a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:104358224">104358224</a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=Journal+of+Industrial+and+Engineering+Chemistry&amp;rft.atitle=A+comparative+study+of+water-immiscible+organic+solvents+in+the+production+of+furfural+from+xylose+and+birch+hydrolysate&amp;rft.volume=72&amp;rft.pages=354-363&amp;rft.date=2019-04-25&amp;rft_id=info%3Ahdl%2F10138%2F307298&amp;rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A104358224%23id-name%3DS2CID&amp;rft_id=info%3Adoi%2F10.1016%2Fj.jiec.2018.12.037&amp;rft.aulast=G%C3%B3mez+Mill%C3%A1n&amp;rft.aufirst=Gerardo&amp;rft.au=Hellsten%2C+Sanna&amp;rft.au=King%2C+Alistair+W.T.&amp;rft.au=Pokki%2C+Juha-Pekka&amp;rft.au=Llorca%2C+Jordi&amp;rft.au=Sixta%2C+Herbert&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3AXylose" class="Z3988"></span></span> </li> <li id="cite_note-9"><span class="mw-cite-backlink"><b><a href="#cite_ref-9">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHoydonckxVan_RhijnVan_RhijnDe_Vos2007" class="citation encyclopaedia cs1">Hoydonckx, H. 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(2007-08-24). <a rel="nofollow" class="external text" href="https://repository.up.ac.za/handle/2263/27501"><i>Physiological and microbiological studies of nectar xylose metabolism in the Namaqua rock mouse, </i>Aethomys namaquensis<i> (A. 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.citation:target{background-color:rgba(0,127,255,0.133)}</style><span class="citation patent"><a rel="nofollow" class="external text" href="https://patents.google.com/patent/US6239274B1/en">US US6239274B1</a>,&#32;"Method of producing xylose",&#32;issued 1999-08-06</span><span class="Z3988" title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Apatent&amp;rft.number=US6239274B1&amp;rft.cc=US&amp;rft.title=Method+of+producing+xylose&amp;rft.date=1999-08-06"><span style="display: none;">&#160;</span></span></span> </li> <li id="cite_note-12"><span class="mw-cite-backlink"><b><a href="#cite_ref-12">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation cs2"><a rel="nofollow" class="external text" href="https://www.nlm.nih.gov/medlineplus/ency/article/003606.htm">"D-xylose absorption"</a>, <i>MedlinePlus</i>, U.S. National Library of Medicine, July 2008<span 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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 class="mw-selflink selflink">Xylose</a></li></ul></li> <li>Ketopentoses <ul><li><a href="/wiki/Ribulose" title="Ribulose">Ribulose</a></li> <li><a href="/wiki/Xylulose" title="Xylulose">Xylulose</a></li></ul></li> <li><a href="/wiki/Deoxy_sugar" title="Deoxy sugar">Deoxy sugars</a> <ul><li><a href="/wiki/Deoxyribose" title="Deoxyribose">Deoxyribose</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Hexose" title="Hexose">Hexoses</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Aldohexose" class="mw-redirect" title="Aldohexose">Aldohexoses</a> <ul><li><a href="/wiki/Allose" title="Allose">Allose</a></li> <li><a href="/wiki/Altrose" title="Altrose">Altrose</a></li> <li><a href="/wiki/Galactose" title="Galactose">Galactose</a></li> <li><a href="/wiki/Glucose" title="Glucose">Glucose</a></li> <li><a href="/wiki/Gulose" title="Gulose">Gulose</a></li> <li><a href="/wiki/Idose" title="Idose">Idose</a></li> <li><a href="/wiki/Mannose" title="Mannose">Mannose</a></li> <li><a href="/wiki/Talose" title="Talose">Talose</a></li></ul></li> <li><a href="/wiki/Ketohexose" class="mw-redirect" title="Ketohexose">Ketohexoses</a> <ul><li><a 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> </div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <ul><li><span class="noviewer" typeof="mw:File"><span title="Category"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/16px-Symbol_category_class.svg.png" decoding="async" width="16" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/23px-Symbol_category_class.svg.png 1.5x, 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