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class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Role_in_disease"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.3</span> <span>Role in disease</span> </div> </a> <ul id="toc-Role_in_disease-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Use" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Use"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Use</span> </div> </a> <ul id="toc-Use-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">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 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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">Glucuronic acid</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 35 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-35" 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">35 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D8%A7%D8%B3%DB%8C%D8%AF_%D9%82%D9%84%D9%88%DA%A9%D9%88%D8%B1%D9%88%D9%86%DB%8C%DA%A9" title="اسید قلوکورونیک – South Azerbaijani" lang="azb" hreflang="azb" data-title="اسید قلوکورونیک" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%93%D0%BB%D1%8E%D0%BA%D1%83%D1%80%D0%BE%D0%BD%D0%BE%D0%B2%D0%B0_%D0%BA%D0%B8%D1%81%D0%B5%D0%BB%D0%B8%D0%BD%D0%B0" title="Глюкуронова киселина – Bulgarian" lang="bg" hreflang="bg" data-title="Глюкуронова киселина" 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/Glukuronska_kiselina" title="Glukuronska kiselina – Bosnian" lang="bs" hreflang="bs" data-title="Glukuronska kiselina" 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/%C3%80cid_glucur%C3%B2nic" title="Àcid glucurònic – Catalan" lang="ca" hreflang="ca" data-title="Àcid glucurònic" 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/Kyselina_glukuronov%C3%A1" title="Kyselina glukuronová – Czech" lang="cs" hreflang="cs" data-title="Kyselina glukuronová" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Glucurons%C3%A4ure" title="Glucuronsäure – German" lang="de" hreflang="de" data-title="Glucuronsäure" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/Gl%C3%BCkuroonhape" title="Glükuroonhape – Estonian" lang="et" hreflang="et" data-title="Glükuroonhape" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/%C3%81cido_glucur%C3%B3nico" title="Ácido glucurónico – Spanish" lang="es" hreflang="es" data-title="Ácido glucurónico" 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/Glukuronata_acido" title="Glukuronata acido – Esperanto" lang="eo" hreflang="eo" data-title="Glukuronata acido" 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/Azido_glukuroniko" title="Azido glukuroniko – Basque" lang="eu" hreflang="eu" data-title="Azido glukuroniko" 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/%D8%A7%D8%B3%DB%8C%D8%AF_%DA%AF%D9%84%D9%88%DA%A9%D9%88%D8%B1%D9%88%D9%86%DB%8C%DA%A9" title="اسید گلوکورونیک – Persian" lang="fa" hreflang="fa" data-title="اسید گلوکورونیک" 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/Acide_glucuronique" title="Acide glucuronique – French" lang="fr" hreflang="fr" data-title="Acide glucuronique" 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/%C3%81cido_glicur%C3%B3nico" title="Ácido glicurónico – Galician" lang="gl" hreflang="gl" data-title="Ácido glicurónico" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EA%B8%80%EB%A3%A8%EC%BF%A0%EB%A1%A0%EC%82%B0" title="글루쿠론산 – Korean" lang="ko" hreflang="ko" data-title="글루쿠론산" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D4%B3%D5%AC%D5%B5%D5%B8%D6%82%D5%AF%D5%B8%D6%82%D6%80%D5%B8%D5%B6%D5%A1%D5%A9%D5%A9%D5%B8%D6%82" title="Գլյուկուրոնաթթու – Armenian" lang="hy" hreflang="hy" data-title="Գլյուկուրոնաթթու" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-io mw-list-item"><a href="https://io.wikipedia.org/wiki/Glikuron-acido" title="Glikuron-acido – Ido" lang="io" hreflang="io" data-title="Glikuron-acido" data-language-autonym="Ido" data-language-local-name="Ido" class="interlanguage-link-target"><span>Ido</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Asam_glukuronat" title="Asam glukuronat – Indonesian" lang="id" hreflang="id" data-title="Asam glukuronat" 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/Acido_glucuronico" title="Acido glucuronico – Italian" lang="it" hreflang="it" data-title="Acido glucuronico" 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%97%D7%95%D7%9E%D7%A6%D7%94_%D7%92%D7%9C%D7%95%D7%A7%D7%95%D7%A8%D7%95%D7%A0%D7%99%D7%AA" title="חומצה גלוקורונית – Hebrew" lang="he" hreflang="he" data-title="חומצה גלוקורונית" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-kk mw-list-item"><a href="https://kk.wikipedia.org/wiki/%D0%93%D0%BB%D1%8E%D0%BA%D1%83%D1%80%D0%BE%D0%BD_%D2%9B%D1%8B%D1%88%D2%9B%D1%8B%D0%BB%D1%8B" title="Глюкурон қышқылы – Kazakh" lang="kk" hreflang="kk" data-title="Глюкурон қышқылы" data-language-autonym="Қазақша" data-language-local-name="Kazakh" class="interlanguage-link-target"><span>Қазақша</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%93%D0%BB%D0%B8%D0%BA%D1%83%D1%80%D0%BE%D0%BD%D1%81%D0%BA%D0%B0_%D0%BA%D0%B8%D1%81%D0%B5%D0%BB%D0%B8%D0%BD%D0%B0" title="Гликуронска киселина – Macedonian" lang="mk" hreflang="mk" data-title="Гликуронска киселина" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Glucuronzuur" title="Glucuronzuur – Dutch" lang="nl" hreflang="nl" data-title="Glucuronzuur" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%B0%E3%83%AB%E3%82%AF%E3%83%AD%E3%83%B3%E9%85%B8" title="グルクロン酸 – Japanese" lang="ja" hreflang="ja" data-title="グルクロン酸" 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-uz mw-list-item"><a href="https://uz.wikipedia.org/wiki/Glyukuron_kislota" title="Glyukuron kislota – Uzbek" lang="uz" hreflang="uz" data-title="Glyukuron kislota" 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/Kwas_glukuronowy" title="Kwas glukuronowy – Polish" lang="pl" hreflang="pl" data-title="Kwas glukuronowy" 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/%C3%81cido_glicur%C3%B4nico" title="Ácido glicurônico – Portuguese" lang="pt" hreflang="pt" data-title="Ácido glicurônico" 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/Acid_glucuronic" title="Acid glucuronic – Romanian" lang="ro" hreflang="ro" data-title="Acid glucuronic" 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%BB%D1%8E%D0%BA%D1%83%D1%80%D0%BE%D0%BD%D0%BE%D0%B2%D0%B0%D1%8F_%D0%BA%D0%B8%D1%81%D0%BB%D0%BE%D1%82%D0%B0" title="Глюкуроновая кислота – Russian" lang="ru" hreflang="ru" data-title="Глюкуроновая кислота" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Glukuronska_kislina" title="Glukuronska kislina – Slovenian" lang="sl" hreflang="sl" data-title="Glukuronska kislina" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Glukuronska_kiselina" title="Glukuronska kiselina – Serbian" lang="sr" hreflang="sr" data-title="Glukuronska kiselina" 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/Glukuronska_kiselina" title="Glukuronska kiselina – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Glukuronska kiselina" 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/Glukuronihappo" title="Glukuronihappo – Finnish" lang="fi" hreflang="fi" data-title="Glukuronihappo" 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/Glukuronsyra" title="Glukuronsyra – Swedish" lang="sv" hreflang="sv" data-title="Glukuronsyra" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%93%D0%BB%D1%8E%D0%BA%D1%83%D1%80%D0%BE%D0%BD%D0%BE%D0%B2%D0%B0_%D0%BA%D0%B8%D1%81%D0%BB%D0%BE%D1%82%D0%B0" title="Глюкуронова кислота – Ukrainian" lang="uk" hreflang="uk" data-title="Глюкуронова кислота" 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/%E8%91%A1%E8%90%84%E7%B3%96%E9%86%9B%E9%85%B8" title="葡萄糖醛酸 – Chinese" lang="zh" hreflang="zh" data-title="葡萄糖醛酸" 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/Q409216#sitelinks-wikipedia" title="Edit interlanguage links" class="wbc-editpage">Edit links</a></span></div> </div> </div> </div> </header> <div class="vector-page-toolbar"> <div class="vector-page-toolbar-container"> <div id="left-navigation"> <nav aria-label="Namespaces"> <div id="p-associated-pages" class="vector-menu vector-menu-tabs mw-portlet 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</div> </nav> </div> </div> </div> <div class="vector-column-end"> <div class="vector-sticky-pinned-container"> <nav class="vector-page-tools-landmark" aria-label="Page tools"> <div id="vector-page-tools-pinned-container" class="vector-pinned-container"> </div> </nav> <nav class="vector-appearance-landmark" aria-label="Appearance"> <div id="vector-appearance-pinned-container" class="vector-pinned-container"> <div id="vector-appearance" class="vector-appearance vector-pinnable-element"> <div class="vector-pinnable-header vector-appearance-pinnable-header vector-pinnable-header-pinned" data-feature-name="appearance-pinned" 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" 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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">Not to be confused with <a href="/wiki/Gluconic_acid" title="Gluconic acid">Gluconic acid</a> or <a href="/wiki/Guluronic_acid" title="Guluronic acid">Guluronic acid</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>Glucuronic acid </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Beta_D-Glucuronic_acid.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6c/Beta_D-Glucuronic_acid.svg/220px-Beta_D-Glucuronic_acid.svg.png" decoding="async" width="220" height="122" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6c/Beta_D-Glucuronic_acid.svg/330px-Beta_D-Glucuronic_acid.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6c/Beta_D-Glucuronic_acid.svg/440px-Beta_D-Glucuronic_acid.svg.png 2x" data-file-width="512" data-file-height="283" /></a></span> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Beta-D-glucuronic-acid-3D-balls.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/9d/Beta-D-glucuronic-acid-3D-balls.png/220px-Beta-D-glucuronic-acid-3D-balls.png" decoding="async" width="220" height="212" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/9d/Beta-D-glucuronic-acid-3D-balls.png/330px-Beta-D-glucuronic-acid-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/9d/Beta-D-glucuronic-acid-3D-balls.png/440px-Beta-D-glucuronic-acid-3D-balls.png 2x" data-file-width="1100" data-file-height="1062" /></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;">β-<small>D</small>-Glucopyranuronic acid</div> </td></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Chemical_nomenclature#Systematic_name" title="Chemical nomenclature">Systematic IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;">(2<i>S</i>,3<i>S</i>,4<i>S</i>,5<i>R</i>,6<i>R</i>)-3,4,5,6-Tetrahydroxyoxane-2-carboxylic acid</div></div> </td></tr> <tr> <td colspan="2" style="text-align:left;">Other names <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">β-<small>D</small>-Glucuronic acid, GlcA</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=6556-12-3">6556-12-3</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=O%3DC%28O%29%5BC%40H%5D1O%5BC%40H%5D%28O%29%5BC%40H%5D%28O%29%5BC%40%40H%5D%28O%29%5BC%40%40H%5D1O">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=28860">CHEBI:28860</a></span><sup> <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.392615.html">392615</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/DrugBank" title="DrugBank">DrugBank</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.drugbank.ca"><a rel="nofollow" class="external text" href="https://www.drugbank.ca/drugs/DB03156">DB03156</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a> </td> <td><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.026.807">100.026.807</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q409216#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/KEGG" title="KEGG">KEGG</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.kegg.jp"><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/C00191">C00191</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/Medical_Subject_Headings" title="Medical Subject Headings">MeSH</a> </td> <td><span title="www.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://www.nlm.nih.gov/cgi/mesh/2014/MB_cgi?mode=&term=Glucuronic+acid">Glucuronic+acid</a></span> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/441478">441478</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/8A5D83Q4RW">8A5D83Q4RW</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID40273973">DTXSID40273973</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q409216#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></span></li></ul></div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/C6H10O7/c7-1-2(8)4(5(10)11)13-6(12)3(1)9/h1-4,6-9,12H,(H,10,11)/t1-,2-,3+,4-,6-/m0/s1<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: AEMOLEFTQBMNLQ-WAXACMCWSA-N<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div></div></li><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/C6H10O7/c7-1-2(8)4(5(10)11)13-6(12)3(1)9/h1-4,6-9,12H,(H,10,11)/t1-,2-,3+,4-,6-/m0/s1</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: AEMOLEFTQBMNLQ-WAXACMCWBB</div></div></li></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">O=C(O)[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@@H]1O</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td><span title="Carbon">C</span><sub>6</sub><span title="Hydrogen">H</span><sub>10</sub><span title="Oxygen">O</span><sub>7</sub> </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td><span class="nowrap"><span data-sort-value="7002194139000000000♠"></span>194.139</span> g·mol<sup>−1</sup>   </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>159 to 161 °C (318 to 322 °F; 432 to 434 K)<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </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/Uronic_acid" title="Uronic acid">uronic acids</a></div> </td> <td><a href="/w/index.php?title=Alluronic_acid&action=edit&redlink=1" class="new" title="Alluronic acid (page does not exist)">Alluronic acid</a>, <a href="/w/index.php?title=Altruronic_acid&action=edit&redlink=1" class="new" title="Altruronic acid (page does not exist)">Altruronic acid</a>, <a href="/w/index.php?title=Arabinuronic_acid&action=edit&redlink=1" class="new" title="Arabinuronic acid (page does not exist)">Arabinuronic acid</a>, <a href="/wiki/Fructuronic_acid" class="mw-redirect" title="Fructuronic acid">Fructuronic acid</a>, <a href="/wiki/Galacturonic_acid" class="mw-redirect" title="Galacturonic acid">Galacturonic acid</a>, <a href="/wiki/Guluronic_acid" title="Guluronic acid">Guluronic acid</a>, <a href="/wiki/Iduronic_acid" title="Iduronic acid">Iduronic acid</a>, <a href="/w/index.php?title=Lyxuronic_acid&action=edit&redlink=1" class="new" title="Lyxuronic acid (page does not exist)">Lyxuronic acid</a>, <a href="/wiki/Mannuronic_acid" title="Mannuronic acid">Mannuronic acid</a>, <a href="/w/index.php?title=Psicuronic_acid&action=edit&redlink=1" class="new" title="Psicuronic acid (page does not exist)">Psicuronic acid</a>, <a href="/w/index.php?title=Riburonic_acid&action=edit&redlink=1" class="new" title="Riburonic acid (page does not exist)">Riburonic acid</a>, <a href="/w/index.php?title=Ribuluronic_acid&action=edit&redlink=1" class="new" title="Ribuluronic acid (page does not exist)">Ribuluronic acid</a>, <a href="/w/index.php?title=Sorburonic_acid&action=edit&redlink=1" class="new" title="Sorburonic acid (page does not exist)">Sorburonic acid</a>, <a href="/w/index.php?title=Tagaturonic_acid&action=edit&redlink=1" class="new" title="Tagaturonic acid (page does not exist)">Tagaturonic acid</a>, <a href="/w/index.php?title=Taluronic_acid&action=edit&redlink=1" class="new" title="Taluronic acid (page does not exist)">Taluronic acid</a>, <a href="/w/index.php?title=Xyluluronic_acid&action=edit&redlink=1" class="new" title="Xyluluronic acid (page does not exist)">Xyluluronic acid</a>, <a href="/w/index.php?title=Xyluronic_acid&action=edit&redlink=1" class="new" title="Xyluronic acid (page does not exist)">Xyluronic acid</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 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"><div style="text-align:center;"><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/12px-X_mark.svg.png" decoding="async" width="12" height="14" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/18px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/24px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span> <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=476992728&page2=Glucuronic+acid">verify</a></span> (<a href="/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validation" title="Wikipedia:WikiProject Chemicals/Chembox validation">what is</a> <sup><span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup> ?) </div></div> <div style="margin-top: 0.3em; text-align: center;"><a href="/wiki/Wikipedia:Chemical_infobox#References" title="Wikipedia:Chemical infobox">Infobox references</a></div> </td></tr> </tbody></table><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound</div> <p><b>Glucuronic acid</b> (from <a href="/wiki/Ancient_Greek" title="Ancient Greek">Greek</a> γλεῦκος "<i>sweet wine, must</i>" and οὖρον "<i>urine</i>") is a <a href="/wiki/Uronic_acid" title="Uronic acid">uronic acid</a> that was first isolated from <a href="/wiki/Urine" title="Urine">urine</a> (hence the name "uronic acid"). It is found in many <a href="/wiki/Natural_gum" title="Natural gum">gums</a> such as <a href="/wiki/Gum_arabic" title="Gum arabic">gum arabic</a> (<abbr title="approximately">approx.</abbr> 18%), <a href="/wiki/Xanthan" class="mw-redirect" title="Xanthan">xanthan</a>, and <a href="/wiki/Kombucha" title="Kombucha">kombucha</a> tea and is important for the <a href="/wiki/Metabolism" title="Metabolism">metabolism</a> of microorganisms, plants and animals. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Properties">Properties</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Glucuronic_acid&action=edit&section=1" title="Edit section: Properties"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1251242444">.mw-parser-output .ambox{border:1px solid #a2a9b1;border-left:10px solid #36c;background-color:#fbfbfb;box-sizing:border-box}.mw-parser-output .ambox+link+.ambox,.mw-parser-output .ambox+link+style+.ambox,.mw-parser-output .ambox+link+link+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+style+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+link+.ambox{margin-top:-1px}html body.mediawiki .mw-parser-output .ambox.mbox-small-left{margin:4px 1em 4px 0;overflow:hidden;width:238px;border-collapse:collapse;font-size:88%;line-height:1.25em}.mw-parser-output .ambox-speedy{border-left:10px solid #b32424;background-color:#fee7e6}.mw-parser-output .ambox-delete{border-left:10px solid #b32424}.mw-parser-output .ambox-content{border-left:10px solid #f28500}.mw-parser-output .ambox-style{border-left:10px solid #fc3}.mw-parser-output .ambox-move{border-left:10px solid #9932cc}.mw-parser-output .ambox-protection{border-left:10px solid #a2a9b1}.mw-parser-output .ambox .mbox-text{border:none;padding:0.25em 0.5em;width:100%}.mw-parser-output .ambox .mbox-image{border:none;padding:2px 0 2px 0.5em;text-align:center}.mw-parser-output .ambox .mbox-imageright{border:none;padding:2px 0.5em 2px 0;text-align:center}.mw-parser-output .ambox .mbox-empty-cell{border:none;padding:0;width:1px}.mw-parser-output .ambox .mbox-image-div{width:52px}@media(min-width:720px){.mw-parser-output .ambox{margin:0 10%}}@media print{body.ns-0 .mw-parser-output .ambox{display:none!important}}</style><table class="box-More_citations_needed_section plainlinks metadata ambox ambox-content ambox-Refimprove" role="presentation"><tbody><tr><td class="mbox-image"><div class="mbox-image-div"><span typeof="mw:File"><a href="/wiki/File:Question_book-new.svg" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/9/99/Question_book-new.svg/50px-Question_book-new.svg.png" decoding="async" width="50" height="39" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/9/99/Question_book-new.svg/75px-Question_book-new.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/9/99/Question_book-new.svg/100px-Question_book-new.svg.png 2x" data-file-width="512" data-file-height="399" /></a></span></div></td><td class="mbox-text"><div class="mbox-text-span">This section <b>needs additional citations for <a href="/wiki/Wikipedia:Verifiability" title="Wikipedia:Verifiability">verification</a></b>.<span class="hide-when-compact"> Please help <a href="/wiki/Special:EditPage/Glucuronic_acid" title="Special:EditPage/Glucuronic acid">improve this article</a> by <a href="/wiki/Help:Referencing_for_beginners" title="Help:Referencing for beginners">adding citations to reliable sources</a> in this section. Unsourced material may be challenged and removed.</span> <span class="date-container"><i>(<span class="date">March 2023</span>)</i></span><span class="hide-when-compact"><i> (<small><a href="/wiki/Help:Maintenance_template_removal" title="Help:Maintenance template removal">Learn how and when to remove this message</a></small>)</i></span></div></td></tr></tbody></table> <figure class="mw-default-size mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:GlcA.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/1d/GlcA.jpg/220px-GlcA.jpg" decoding="async" width="220" height="119" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/1d/GlcA.jpg/330px-GlcA.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/1d/GlcA.jpg/440px-GlcA.jpg 2x" data-file-width="466" data-file-height="252" /></a><figcaption>The <i>β</i>-<small>D</small>-methyl glycoside of glucuronic acid in the low energy <sup>4</sup>C<sub>1</sub> conformation of <small>D</small>-glucose</figcaption></figure> <p>Glucuronic acid is a <a href="/wiki/Sugar_acid" title="Sugar acid">sugar acid</a> derived from <a href="/wiki/Glucose" title="Glucose">glucose</a>, with its sixth carbon atom oxidized to a carboxylic acid. In living beings, this primary oxidation occurs with <a href="/wiki/Uridine_diphosphate_glucose" title="Uridine diphosphate glucose">UDP-α-<small>D</small>-glucose</a> (UDPG), not with the free sugar. </p><p>Glucuronic acid, like its precursor <a href="/wiki/Glucose" title="Glucose">glucose</a>, can exist as a linear (carboxo-)<a href="/wiki/Aldohexose" class="mw-redirect" title="Aldohexose">aldohexose</a> (<1%), or as a cyclic <a href="/wiki/Hemiacetal" title="Hemiacetal">hemiacetal</a> (<a href="/wiki/Furanose" title="Furanose">furanose</a> or <a href="/wiki/Pyranose" title="Pyranose">pyranose</a>). Aldohexoses such as <small>D</small>-glucose are capable of forming two furanose forms (α and β) and two pyranose forms (α and β). By the <a href="/wiki/Fischer_projection" title="Fischer projection">Fischer convention</a>, glucuronic acid has two stereoisomers (<a href="/wiki/Enantiomers" class="mw-redirect" title="Enantiomers">enantiomers</a>), <small>D</small>- and <small>L</small>-glucuronic acid, depending on its configuration at C-5. Most physiological sugars are of the <small>D</small>-configuration. Due to ring closure, cyclic sugars have another asymmetric carbon atom (C-1), resulting in two more stereoisomers, named <a href="/wiki/Anomer" title="Anomer">anomers</a>. Depending on the configuration at C-1, there are two anomers of glucuronic acid, α- and β-form. In β-<small>D</small>-glucuronic acid the C-1 hydroxy group is on the same side of the pyranose ring as the carboxyl group. In the free sugar acid, the β-form is prevalent (~64%), whereas in the organism, the α-form <a href="/wiki/Uridine_diphosphate_glucuronic_acid" title="Uridine diphosphate glucuronic acid">UDP-α-<small>D</small>-glucuronic acid</a> (UDPGA) predominates. </p><p>Carbohydrate stereoisomers, which differ in configuration at only one (other) asymmetric C-atom, are named <a href="/wiki/Epimer" title="Epimer">epimers</a>. For example, <a href="/wiki/Mannuronic_acid" title="Mannuronic acid"><small>D</small>-mannuronic</a> (C-2), <a href="/w/index.php?title=Alluronic_acid&action=edit&redlink=1" class="new" title="Alluronic acid (page does not exist)"><small>D</small>-alluronic</a> (C-3), <a href="/wiki/Galacturonic_acid" class="mw-redirect" title="Galacturonic acid"><small>D</small>-galacturonic</a> (C-4), and <a href="/wiki/Iduronic_acid" title="Iduronic acid"><small>L</small>-iduronic acid</a> (C-5) are epimers of glucuronic acid. </p><p>The nonplanar pyranose rings can assume either chair (in 2 variants) or boat conformation. The preferred conformation depends on spatial interference or other interactions of the substituents. The pyranose form of <small>D</small>-glucose and its derivative <small>D</small>-glucuronic acid prefer the chair <sup>4</sup>C<sub>1</sub>. </p><p>Additional oxidation at C-1 to the carboxyl level yields the dicarboxylic <a href="/wiki/Saccharic_acid" title="Saccharic acid">glucaric acid</a>. <a href="/wiki/Glucuronolactone" title="Glucuronolactone">Glucuronolactone</a> is the self-ester (<a href="/wiki/Lactone" title="Lactone">lactone</a>) of glucuronic acid. </p><p>Direct oxidation of an aldose affects the aldehyde group first. A laboratory synthesis of a uronic acid from an aldose requires protecting the aldehyde and hydroxy groups from oxidation, for example by conversion to cyclic <a href="/wiki/Acetal" title="Acetal">acetals</a> (e. g., <a href="/wiki/Acetonide" title="Acetonide">acetonides</a>). </p><p>Sodium glucuronate can be produced by the direct oxidation of starch with concentrated nitric acid. In this preparation the low availability of water keeps the starch polymers from hydrolyzing and only oxidizes the free hydroxyls, in much the same way that nitrogen dioxide would oxidize the starch. Once this reaction is complete, and the starch/nitric acid mix turns clear (after giving off nitrogen dioxide gas), the solution can be diluted, and hydrolyzed with another mineral acid. Then the oxidation is slowly quenched with sodium hydroxide (or sodium bicarbonate), forming sodium glucuronate, which can be crystallized out of solution. With transition metals, it forms complexes such as <a href="/w/index.php?title=Iron(III)_glucuronate&action=edit&redlink=1" class="new" title="Iron(III) glucuronate (page does not exist)">iron(III) glucuronate</a>, <a href="/w/index.php?title=Iron(II)_glucuronate&action=edit&redlink=1" class="new" title="Iron(II) glucuronate (page does not exist)">iron(II) glucuronate</a>, and <a href="/w/index.php?title=Copper(II)_glucuronate&action=edit&redlink=1" class="new" title="Copper(II) glucuronate (page does not exist)">copper(II) glucuronate</a>. </p> <div class="mw-heading mw-heading2"><h2 id="Functions">Functions</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Glucuronic_acid&action=edit&section=2" title="Edit section: Functions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Proteoglycans">Proteoglycans</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Glucuronic_acid&action=edit&section=3" title="Edit section: Proteoglycans"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Glucuronic acid is a common building block of <a href="/wiki/Proteoglycan" title="Proteoglycan">proteoglycans</a> and <a href="/w/index.php?title=Glycoglycerolipid&action=edit&redlink=1" class="new" title="Glycoglycerolipid (page does not exist)">glycoglycerolipids</a>:<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. (March 2022)">citation needed</span></a></i>]</sup> </p> <ul><li><a href="/wiki/Heparin" title="Heparin">Heparin</a> is an inhibitor of blood coagulation, and occurs in mast cells, lung and liver.</li> <li><a href="/wiki/Chondroitin_sulfate" title="Chondroitin sulfate">Chondroitin sulfate</a> is found in large quantities in cartilage, aorta, connective tissue, bone, and skin.</li> <li><a href="/wiki/Dermatan_sulfate" title="Dermatan sulfate">Dermatan sulfate</a> is a proteoglycan in skin, heart, and blood vessels.</li> <li><a href="/wiki/Keratan_sulfate" title="Keratan sulfate">Keratan sulfate</a> is found in the cornea, cartilage, and bone.</li> <li><a href="/wiki/Hyaluronic_acid" title="Hyaluronic acid">Hyaluronic acid</a> occurs in large quantities in connective tissues, skin, cartilage, and synovial fluid.</li> <li><a href="/w/index.php?title=Glycoglycerolipid&action=edit&redlink=1" class="new" title="Glycoglycerolipid (page does not exist)">Glycoglycerolipids</a> of glucuronic or <a href="/wiki/Galacturonic_acid" class="mw-redirect" title="Galacturonic acid">galacturonic acids</a> form the cell walls of bacteria.</li></ul> <div class="mw-heading mw-heading3"><h3 id="Glucuronidation">Glucuronidation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Glucuronic_acid&action=edit&section=4" title="Edit section: Glucuronidation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Glucuronidation" title="Glucuronidation">Glucuronidation</a></div> <figure class="mw-default-size mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:GlucuronidationBiphenylAmine.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/GlucuronidationBiphenylAmine.svg/330px-GlucuronidationBiphenylAmine.svg.png" decoding="async" width="330" height="77" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/GlucuronidationBiphenylAmine.svg/495px-GlucuronidationBiphenylAmine.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/GlucuronidationBiphenylAmine.svg/660px-GlucuronidationBiphenylAmine.svg.png 2x" data-file-width="512" data-file-height="119" /></a><figcaption>Glucuronidation of <a href="/wiki/4-aminobiphenyl" class="mw-redirect" title="4-aminobiphenyl">4-aminobiphenyl</a> by formation of a β-<a href="/wiki/Glycosidic_bond" title="Glycosidic bond">glycosidic bond</a>.</figcaption></figure> <p><a href="/wiki/UDP-glucuronic_acid" class="mw-redirect" title="UDP-glucuronic acid">UDP-α-<small>D</small>-glucuronic acid</a> (UDPGA) is often involved in the <a href="/wiki/Phase_II_metabolism" class="mw-redirect" title="Phase II metabolism">phase II metabolism</a> (<a href="/wiki/Conjugation_(biochemistry)" class="mw-redirect" title="Conjugation (biochemistry)">conjugation</a>) of <a href="/wiki/Lipophilic" class="mw-redirect" title="Lipophilic">lipophilic</a> <a href="/wiki/Xenobiotic" title="Xenobiotic">xeno</a>- and <a href="/wiki/Endobiotic" title="Endobiotic">endobiotics</a>. These linkages involve <a href="/wiki/Glycosidic_bond" title="Glycosidic bond">glycosidic bonds</a> with thiol, amine and hydroxy groups, or esterification with the carboxyl and hydroxyl groups. This linkage process is known as <a href="/wiki/Glucuronidation" title="Glucuronidation">glucuronidation</a> (or glucuronide conjugation). Glucuronidation occurs mainly in the liver, although the enzymes responsible for its catalysis, <a href="/wiki/Glucuronosyltransferase" title="Glucuronosyltransferase">UDP-glucuronyltransferases</a> (UDP-GT), have been found in all major body organs, e.g., intestine, kidneys, brain, adrenal gland, spleen, and thymus.<sup id="cite_ref-Ohno_2-0" class="reference"><a href="#cite_note-Ohno-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> Analogous reactions occur with other <a href="/wiki/Uridine_diphosphate" title="Uridine diphosphate">UDP</a>-<a href="/wiki/Uronic_acid" title="Uronic acid">uronic acids</a> (e. g., <a href="/wiki/D-Galacturonic_acid" title="D-Galacturonic acid"><small>D</small>-galacturonic acid</a>). </p><p><a href="/wiki/Glycoside" title="Glycoside">Glycosides</a> resulting from glucuronidation are named β-<small>D</small>-glucuronides, its salts and esters are named glucuronates. The human body uses glucuronidation to make <a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">alcohols</a>, <a href="/wiki/Phenol" title="Phenol">phenols</a>, <a href="/wiki/Carboxylic_acid" title="Carboxylic acid">carboxylic acids</a>, <a href="/wiki/Mercaptan" class="mw-redirect" title="Mercaptan">mercaptans</a>, primary and secondary aliphatic <a href="/wiki/Amine" title="Amine">amines</a>, and <a href="/wiki/Carbamate" title="Carbamate">carbamates</a> more water-soluble, and, in this way, allows for their subsequent elimination from the body through urine or faeces (via bile from the liver) at a significantly increased rate. The carboxyl group is ionized at physiological pH, making the conjugated compound water-soluble. Compounds with molecular masses > 60,000 are too large for renal excretion and will be excreted with bile into the intestine. Neonates are deficient in this conjugating system, making them particularly vulnerable to drugs such as <a href="/wiki/Chloramphenicol" title="Chloramphenicol">chloramphenicol</a>, which is inactivated by the addition of glucuronic acid, resulting in <a href="/wiki/Gray_baby_syndrome" title="Gray baby syndrome">gray baby syndrome</a>. <a href="/wiki/Bilirubin" title="Bilirubin">Bilirubin</a> is excreted in the bile as <a href="/wiki/Bilirubin_diglucuronide" title="Bilirubin diglucuronide">bilirubin diglucuronide</a> (80%), <a href="/wiki/Bilirubin_glucuronide" title="Bilirubin glucuronide">bilirubin glucuronide</a> (20%), and unconjugated bilirubin (< 1%). In the <a href="/wiki/Crigler%E2%80%93Najjar_syndrome" title="Crigler–Najjar syndrome">Crigler–Najjar syndrome</a> and the <a href="/wiki/Gilbert_syndrome" class="mw-redirect" title="Gilbert syndrome">Gilbert syndrome</a>, UDPGT activity is reduced or nearly absent due to mutations, resulting in <a href="/wiki/Jaundice" title="Jaundice">jaundice</a>. </p><p>It is possible to exhaust the body's supply of glucuronic acid by combining multiple drugs/substances whose metabolism and excretion are primarily or entirely dependent on glucuronidation. Although most such substances have secondary metabolic routes which become prominent following GCA depletion, the rate of metabolism is reduced enough to produce a marked accumulation of all GCA substrates in the system; this often increases drug concentrations in the blood by medically relevant amounts. In the most severe cases permanent and debilitating organ damage (particularly the liver, kidneys, heart, and brain), and even death, have been known to occur. <a href="/wiki/Ethanol" title="Ethanol">Ethanol</a>, <a href="/wiki/Morphine" title="Morphine">morphine</a>, <a href="/wiki/Paracetamol" title="Paracetamol">paracetamol (acetaminophen)</a>, cyclooxygenase inhibitors (<a href="/wiki/NSAIDs" class="mw-redirect" title="NSAIDs">NSAIDs</a>), <a href="/wiki/Endogenous" class="mw-redirect" title="Endogenous">endogenous</a> <a href="/wiki/Steroid" title="Steroid">steroids</a>, and certain <a href="/wiki/Benzodiazepine" title="Benzodiazepine">benzodiazepines</a> are all capable of contributing to GCA depletion, with ethanol and acetaminophen being the most commonly implicated substances involved in cases of accidental overdoses which have been positively attributed to glucuronic acid depletion. </p><p>Excessive quantities of GCA can also be hazardous to health<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. (November 2016)">citation needed</span></a></i>]</sup>. Tobacco smoke, most <a href="/wiki/Barbiturate" title="Barbiturate">barbiturates</a>, and some carbamates are known to actually stimulate GCA production. Increased GCA activity results in a decrease of the concentration and metabolic half-life of glucuronic acid substrates, causing the plasma levels of glucuronidated drugs to fall below their therapeutic threshold. Excessive glucuronidation of the substrates may result in an inadequate response to traditional doses of affected medications and, unless the drug has a very wide therapeutic index, will generally result in the acute failure of the pharmacotherapy and necessitate the transition from one or more implicated drugs to an equivalent regimen of non-glucuronidated alternatives. A select number of antidepressants and a wide range of anti-psychotic agents are glucuronidation ligands, but due to their delayed mechanism of action and pharmacokinetic properties the decrease of their plasma concentrations may not be immediately apparent and tends to present as a sudden and intense relapse of symptoms instead of a gradual regression to the behaviors and thought patterns exhibited by the patient prior to the initiation of their pharmacological treatment. </p><p>Glucuronides may be <a href="/wiki/Hydrolysis" title="Hydrolysis">hydrolyzed</a> by <a href="/wiki/Beta-glucuronidase" class="mw-redirect" title="Beta-glucuronidase">β-glucuronidase</a> present in intestinal microflora to the respective aglycone, which may be reabsorbed from the intestine and translocated back to the liver with the blood. The resulting cycle is called <a href="/wiki/Enterohepatic_circulation" title="Enterohepatic circulation">enterohepatic circulation</a>. Compounds that undergo enterohepatic circulation are only slowly excreted and usually have a longer half-life in the body. </p><p>Certain glucuronides are electrophilic and may function in <a href="/wiki/Toxication" title="Toxication">toxication</a> processes. Covalent binding of the aglycone portions of several carboxylic acid (ester) glucuronides is known to occur to nucleophilic sites on <a href="/wiki/Serum_albumin" title="Serum albumin">serum albumin</a> via trans<a href="/wiki/Acylation" title="Acylation">acylation</a> reactions, for example.<sup id="cite_ref-et_4-0" class="reference"><a href="#cite_note-et-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p><p><a href="/wiki/Phenol" title="Phenol">Phenols</a>, quantitatively important <a href="/wiki/Cytochrome_P450" title="Cytochrome P450">P450</a>-derived metabolites of aromatic hydrocarbons, are substrates for both UDP-GT and <a href="/wiki/Sulfotransferase" title="Sulfotransferase">sulfotransferases</a>. Glucuronides predominate with phenol or a phenol precursor (<a href="/wiki/Benzene" title="Benzene">benzene</a>) in mammals because sulfate formation is a high-affinity, low-capacity system (due to sulfate depletion), whereas glucuronidation is a low-affinity, high-capacity (although still exhaustible) system.<sup id="cite_ref-et_4-1" class="reference"><a href="#cite_note-et-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Role_in_disease">Role in disease</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Glucuronic_acid&action=edit&section=5" title="Edit section: Role in disease"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Glucuronic acid, as well as the glucuronidated metabolite of <a href="/wiki/Drinking_alcohol" class="mw-redirect" title="Drinking alcohol">ethanol</a>, <a href="/wiki/Ethyl_glucuronide" title="Ethyl glucuronide">ethyl glucuronide</a> (ETG), act on <a href="/wiki/TLR4" class="mw-redirect" title="TLR4">toll-like receptor 4</a> to aggravate both acute and chronic inflammatory conditions as well as increasing the perceived severity of pain in patients with chronic pain conditions, via up-regulation of the production and release of <a href="/wiki/Endogeny_(biology)" title="Endogeny (biology)">endogenous</a> <a href="/wiki/Cytokines" class="mw-redirect" title="Cytokines">inflammatory signaling molecules</a> within the body. Long-term agonism of the TLR4 receptor (such as that which occurs from GCA, ETG, and <a href="/wiki/Opioid-induced_hyperalgesia" title="Opioid-induced hyperalgesia">opiates</a>) results in chronically painful conditions being perceived as considerably more severe than they did previously while pre-existing tolerable yet occasionally painful activities can become more painful than before and will begin to be aggravated by briefer and less physically demanding activities. It can also cause equally painful responses to decreasingly noxious (irritating) stimuli, eventually resulting in considerable agony from stimuli which wouldn't cause any amount of pain to most individuals.<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Use">Use</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Glucuronic_acid&action=edit&section=6" title="Edit section: Use"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Determination of urinary steroids and of steroid conjugates in blood. <a href="/wiki/Ethyl_glucuronide" title="Ethyl glucuronide">Ethyl glucuronide</a> and <a href="/wiki/Ethyl_sulfate" title="Ethyl sulfate">ethyl sulfate</a> are excreted in urine as metabolites of <a href="/wiki/Ethanol" title="Ethanol">ethanol</a> and are used to monitor alcohol use or dependence. </p><p>Glucuronic acid and gluconic acid are <a href="/wiki/Fermentation" title="Fermentation">fermentation</a> products in <a href="/wiki/Kombucha" title="Kombucha">Kombucha</a> tea.<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>Glucuronic acid is a precursor of <a href="/wiki/Ascorbic_acid" class="mw-redirect" title="Ascorbic acid">ascorbic acid</a> (<a href="/wiki/Vitamin_C" title="Vitamin C">vitamin C</a>, formerly called L-hexuronic acid). Ascorbate can be biosynthesized by higher plants, algae, yeast and most animals. An adult goat produces ~13 g of vitamin C per day. This ability is lacking in some mammals (including humans and guinea pigs) and also in insects, invertebrates and most fishes. These species require external ascorbate supply, because they lack the biosynthetic enzyme <small>L</small>-<a href="/wiki/Gulonolactone_oxidase" class="mw-redirect" title="Gulonolactone oxidase">gulonolactone oxidase</a>.<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p><p>The glucuronide 4-methylumbelliferyl-β-<small>D</small>-glucuronide (MUG) is used to test for the presence of <i><a href="/wiki/Escherichia_coli" title="Escherichia coli">Escherichia coli</a></i>. <i>E. coli</i> produces the enzyme β-glucuronidase, which hydrolyzes the MUG molecule to a fluorescent product that is detectable under <a href="/wiki/Ultraviolet_light" class="mw-redirect" title="Ultraviolet light">ultraviolet light</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=Glucuronic_acid&action=edit&section=7" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Gluconic_acid" title="Gluconic acid">Gluconic acid</a></li> <li><a href="/wiki/Isosaccharinic_acid" title="Isosaccharinic acid">Isosaccharinic acid</a></li> <li><a href="/wiki/Uronic_acid" title="Uronic acid">Uronic acid</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=Glucuronic_acid&action=edit&section=8" 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 reflist-columns references-column-width reflist-columns-2"> <ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text"><a rel="nofollow" class="external text" href="http://www.sigmaaldrich.com/catalog/product/sigma/g5269?lang=en&region=US">D-Glucuronic acid</a> at <a href="/wiki/Sigma-Aldrich" title="Sigma-Aldrich">Sigma-Aldrich</a></span> </li> <li id="cite_note-Ohno-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-Ohno_2-0">^</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 id="CITEREFOhnoNakajin,_Shizuo2008" class="citation journal cs1">Ohno S, Nakajin, Shizuo (2008-10-06). <a rel="nofollow" class="external text" href="http://dmd.aspetjournals.org/content/37/1/32.abstract">"Determination of mRNA Expression of Human UDP-Glucuronosyltransferases and Application for Localization in Various Human Tissues by Real-Time Reverse Transcriptase-Polymerase Chain Reaction"</a>. <i><a href="/wiki/Drug_Metabolism_and_Disposition" title="Drug Metabolism and Disposition">Drug Metabolism and Disposition</a></i>. <b>37</b> (1). <a href="/wiki/American_Society_for_Pharmacology_and_Experimental_Therapeutics" title="American Society for Pharmacology and Experimental Therapeutics">American Society for Pharmacology and Experimental Therapeutics</a>: 32–40. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1124%2Fdmd.108.023598">10.1124/dmd.108.023598</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/18838504">18838504</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:5150289">5150289</a><span class="reference-accessdate">. Retrieved <span class="nowrap">2010-11-07</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Drug+Metabolism+and+Disposition&rft.atitle=Determination+of+mRNA+Expression+of+Human+UDP-Glucuronosyltransferases+and+Application+for+Localization+in+Various+Human+Tissues+by+Real-Time+Reverse+Transcriptase-Polymerase+Chain+Reaction&rft.volume=37&rft.issue=1&rft.pages=32-40&rft.date=2008-10-06&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A5150289%23id-name%3DS2CID&rft_id=info%3Apmid%2F18838504&rft_id=info%3Adoi%2F10.1124%2Fdmd.108.023598&rft.aulast=Ohno&rft.aufirst=Shuji&rft.au=Nakajin%2C+Shizuo&rft_id=http%3A%2F%2Fdmd.aspetjournals.org%2Fcontent%2F37%2F1%2F32.abstract&rfr_id=info%3Asid%2Fen.wikipedia.org%3AGlucuronic+acid" 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="CITEREFBockKöhle2005" class="citation book cs1">Bock K, Köhle C (2005). "UDP-Glucuronosyltransferase 1A6: Structural, Functional, and Regulatory Aspects". <i>Phase II Conjugation Enzymes and Transport Systems</i>. Methods in Enzymology. 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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="CITEREFGerhard_MichalDietmar_Schomburg2012" class="citation cs2">Gerhard Michal, Dietmar Schomburg (2012), <i>Biochemical Pathways: An Atlas of Biochemistry and Molecular Biology</i> (2nd ed.), Wiley, p. 145a, <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-470-14684-2" title="Special:BookSources/978-0-470-14684-2"><bdi>978-0-470-14684-2</bdi></a></cite><span 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