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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">Ergosterol</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 30 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-30" 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">30 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%A5%D8%B1%D8%BA%D9%88%D8%B3%D8%AA%D9%8A%D8%B1%D9%88%D9%84" title="إرغوستيرول – Arabic" lang="ar" hreflang="ar" data-title="إرغوستيرول" 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/%D8%A7%D8%B1%D9%82%D9%88%D8%B3%D8%AA%D8%B1%D9%88%D9%84" title="ارقوسترول – South Azerbaijani" lang="azb" hreflang="azb" data-title="ارقوسترول" 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%86%E0%A6%B0%E0%A7%8D%E0%A6%97%E0%A7%8B%E0%A6%B8%E0%A7%8D%E0%A6%9F%E0%A7%87%E0%A6%B0%E0%A6%B2" title="আর্গোস্টেরল – Bangla" lang="bn" hreflang="bn" data-title="আর্গোস্টেরল" data-language-autonym="বাংলা" data-language-local-name="Bangla" class="interlanguage-link-target"><span>বাংলা</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Ergosterol" title="Ergosterol – Catalan" lang="ca" hreflang="ca" data-title="Ergosterol" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Ergosterin" title="Ergosterin – German" lang="de" hreflang="de" data-title="Ergosterin" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Ergosterol" title="Ergosterol – Spanish" lang="es" hreflang="es" data-title="Ergosterol" 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/Ergosterolo" title="Ergosterolo – Esperanto" lang="eo" hreflang="eo" data-title="Ergosterolo" 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/Ergosterol" title="Ergosterol – Basque" lang="eu" hreflang="eu" data-title="Ergosterol" 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%B1%DA%AF%D9%88%D8%B3%D8%AA%D8%B1%D9%88%D9%84" title="ارگوسترول – Persian" lang="fa" hreflang="fa" data-title="ارگوسترول" 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/Ergost%C3%A9rol" title="Ergostérol – French" lang="fr" hreflang="fr" data-title="Ergostérol" 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/Ergosterol" title="Ergosterol – Galician" lang="gl" hreflang="gl" data-title="Ergosterol" 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%97%90%EB%A5%B4%EA%B3%A0%EC%8A%A4%ED%85%8C%EB%A1%A4" title="에르고스테롤 – Korean" lang="ko" hreflang="ko" data-title="에르고스테롤" 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/Ergosterol" title="Ergosterol – Indonesian" lang="id" hreflang="id" data-title="Ergosterol" 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/Ergosterolo" title="Ergosterolo – Italian" lang="it" hreflang="it" data-title="Ergosterolo" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-kn mw-list-item"><a href="https://kn.wikipedia.org/wiki/%E0%B2%8E%E0%B2%B0%E0%B3%8D%E0%B2%97%E0%B3%8A%E0%B2%B8%E0%B3%8D%E0%B2%9F%E0%B3%80%E0%B2%B0%E0%B2%BE%E0%B2%B2%E0%B3%8D" title="ಎರ್ಗೊಸ್ಟೀರಾಲ್ – Kannada" lang="kn" hreflang="kn" data-title="ಎರ್ಗೊಸ್ಟೀರಾಲ್" data-language-autonym="ಕನ್ನಡ" data-language-local-name="Kannada" class="interlanguage-link-target"><span>ಕನ್ನಡ</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%95%D1%80%D0%B3%D0%BE%D1%81%D1%82%D0%B5%D1%80%D0%BE%D0%BB" title="Ергостерол – Macedonian" lang="mk" hreflang="mk" data-title="Ергостерол" 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/Ergosterol" title="Ergosterol – Dutch" lang="nl" hreflang="nl" data-title="Ergosterol" 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%A8%E3%83%AB%E3%82%B4%E3%82%B9%E3%83%86%E3%83%AD%E3%83%BC%E3%83%AB" title="エルゴステロール – Japanese" lang="ja" hreflang="ja" data-title="エルゴステロール" 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/Ergosterol" title="Ergosterol – Norwegian Nynorsk" lang="nn" hreflang="nn" data-title="Ergosterol" 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/Ergosterol" title="Ergosterol – Polish" lang="pl" hreflang="pl" data-title="Ergosterol" 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/Ergosterol" title="Ergosterol – Portuguese" lang="pt" hreflang="pt" data-title="Ergosterol" 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/Ergosterol" title="Ergosterol – Romanian" lang="ro" hreflang="ro" data-title="Ergosterol" 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%AD%D1%80%D0%B3%D0%BE%D1%81%D1%82%D0%B5%D1%80%D0%BE%D0%BB" title="Эргостерол – Russian" lang="ru" hreflang="ru" data-title="Эргостерол" 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/Ergosterol" title="Ergosterol – Slovenian" lang="sl" hreflang="sl" data-title="Ergosterol" 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/Ergosterol" title="Ergosterol – Serbian" lang="sr" hreflang="sr" data-title="Ergosterol" 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/Ergosterol" title="Ergosterol – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Ergosterol" 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/Ergosteroli" title="Ergosteroli – Finnish" lang="fi" hreflang="fi" data-title="Ergosteroli" 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/Ergosterol" title="Ergosterol – Swedish" lang="sv" hreflang="sv" data-title="Ergosterol" 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%95%D1%80%D0%B3%D0%BE%D1%81%D1%82%D0%B5%D1%80%D0%B8%D0%BD" title="Ергостерин – Ukrainian" lang="uk" hreflang="uk" data-title="Ергостерин" 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/%E9%BA%A6%E8%A7%92%E5%9B%BA%E9%86%87" title="麦角固醇 – Chinese" lang="zh" hreflang="zh" data-title="麦角固醇" 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 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dir="ltr"><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>Ergosterol </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Ergosterol_structure.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/5d/Ergosterol_structure.svg/250px-Ergosterol_structure.svg.png" decoding="async" width="250" height="130" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/5d/Ergosterol_structure.svg/375px-Ergosterol_structure.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/5d/Ergosterol_structure.svg/500px-Ergosterol_structure.svg.png 2x" data-file-width="512" data-file-height="267" /></a></span> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Ergosterol_molecule_ball.png" class="mw-file-description"><img alt="Ball-and-stick model of ergosterol" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e1/Ergosterol_molecule_ball.png/260px-Ergosterol_molecule_ball.png" decoding="async" width="260" height="142" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e1/Ergosterol_molecule_ball.png/390px-Ergosterol_molecule_ball.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e1/Ergosterol_molecule_ball.png/520px-Ergosterol_molecule_ball.png 2x" data-file-width="2000" data-file-height="1096" /></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;">(22<i>E</i>)-Ergosta-5,7,22-trien-3β-ol</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;">(1<i>R</i>,3a<i>R</i>,7<i>S</i>,9a<i>R</i>,9b<i>S</i>,11a<i>R</i>)-1-[(2<i>R</i>,3<i>E</i>,5<i>R</i>)-5,6-Dimethylhept-3-en-2-yl]-7-hydroxy-9a,11a-dimethyl-2,3,3a,6,7,8,9,9a,9b,10,11,11a-dodecahydro-1<i>H</i>-cyclopenta[<i>a</i>]phenanthren-7-ol</div></div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=57-87-4">57-87-4</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=O%5BC%40%40H%5D4C%2FC3%3DC%2FC%3DC1%5C%5BC%40H%5D%28CC%5BC%40%5D2%28%5BC%40H%5D1CC%5BC%40%40H%5D2%5BC%40%40H%5D%28%2FC%3DC%2F%5BC%40H%5D%28C%29C%28C%29C%29C%29C%29%5BC%40%40%5D3%28C%29CC4">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=16933">CHEBI:16933</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembldb/index.php/compound/inspect/ChEMBL1232562">ChEMBL1232562</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.392539.html">392539</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a> </td> <td><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.000.320">100.000.320</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q143263#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>200-352-7</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=Ergosterol">Ergosterol</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/444679">444679</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/Z30RAY509F">Z30RAY509F</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/DTXSID90878679">DTXSID90878679</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q143263#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/C28H44O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h7-10,18-20,22,24-26,29H,11-17H2,1-6H3/b8-7+/t19-,20+,22-,24+,25-,26-,27-,28+/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: DNVPQKQSNYMLRS-APGDWVJJSA-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/C28H44O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h7-10,18-20,22,24-26,29H,11-17H2,1-6H3/b8-7+/t19-,20+,22-,24+,25-,26-,27-,28+/m0/s1</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: DNVPQKQSNYMLRS-APGDWVJJBI</div></div></li></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">O[C@@H]4C/C3=C/C=C1\[C@H](CC[C@]2([C@H]1CC[C@@H]2[C@@H](/C=C/[C@H](C)C(C)C)C)C)[C@@]3(C)CC4</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>C<sub>28</sub>H<sub>44</sub>O  </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td>396.65 g/mol    </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>160 °C (320 °F; 433 K) </td></tr> <tr> <td><a href="/wiki/Boiling_point" title="Boiling point">Boiling point</a> </td> <td>250 °C (482 °F; 523 K) </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Magnetic_susceptibility" title="Magnetic susceptibility">Magnetic susceptibility</a> (χ)</div> </td> <td>-279.6·10<sup>−6</sup> cm<sup>3</sup>/mol </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=461094825&page2=Ergosterol">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>Ergosterol</b> (ergosta-5,7,22-trien-3β-ol) is a <a href="/wiki/Sterol#Types" title="Sterol">mycosterol</a> found in <a href="/wiki/Cell_membrane" title="Cell membrane">cell membranes</a> of <a href="/wiki/Fungus" title="Fungus">fungi</a> and <a href="/wiki/Protozoa" title="Protozoa">protozoa</a>, serving many of the same functions that <a href="/wiki/Cholesterol" title="Cholesterol">cholesterol</a> serves in <a href="/wiki/Animal" title="Animal">animal</a> <a href="/wiki/Cell_(biology)" title="Cell (biology)">cells</a>. Because many fungi and protozoa cannot survive without ergosterol, the <a href="/wiki/Enzyme" title="Enzyme">enzymes</a> that synthesize it have become important targets for <a href="/wiki/Drug_discovery" title="Drug discovery">drug discovery</a>. In human nutrition, ergosterol is a <a href="/wiki/Provitamin" title="Provitamin">provitamin</a> form of <a href="/wiki/Ergocalciferol" title="Ergocalciferol">vitamin D<sub>2</sub></a>; exposure to <a href="/wiki/Ultraviolet" title="Ultraviolet">ultraviolet</a> (UV) light causes a chemical reaction that produces <a href="/wiki/Ergocalciferol" title="Ergocalciferol">vitamin D<sub>2</sub></a>. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Role_in_fungi">Role in fungi</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ergosterol&action=edit&section=1" title="Edit section: Role in fungi"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Ergosterol (ergosta-5,7,22-trien-3β-ol) is a <a href="/wiki/Sterol" title="Sterol">sterol</a> found in fungi, and named after <a href="/wiki/Ergot" title="Ergot">ergot</a>, the common name of members of the fungal genus <i><a href="/wiki/Claviceps" class="mw-redirect" title="Claviceps">Claviceps</a></i> from which ergosterol was first isolated. Ergosterol is a component of <a href="/wiki/Yeast" title="Yeast">yeast</a> and other <a href="/wiki/Fungus" title="Fungus">fungal</a> <a href="/wiki/Cell_membrane" title="Cell membrane">cell membranes</a>, serving many of the same functions that cholesterol serves in animal cells.<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> Its specificity in higher fungi is thought to be related to the climatic instabilities (highly varying humidity and moisture conditions) encountered by these organisms in their typical ecological niches (plant and animal surfaces, soil). Thus, despite the added energy requirements of ergosterol synthesis (if compared to cholesterol), ergosterol is thought to have evolved as a nearly ubiquitous, evolutionarily advantageous fungal alternative to cholesterol.<sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> This advantage could be linked to the presence of two conjugated double bonds in the structure (B-ring) of ergosterol giving it antioxidant properties.<sup id="cite_ref-pmid34202105_3-0" class="reference"><a href="#cite_note-pmid34202105-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Target_for_antifungal_drugs">Target for antifungal drugs</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ergosterol&action=edit&section=2" title="Edit section: Target for antifungal drugs"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Because ergosterol is present in cell membranes of fungi, yet absent in those of animals, it is a useful target for <a href="/wiki/Antifungal" title="Antifungal">antifungal</a> drugs. Ergosterol is also present in the cell membranes of some protists, such as <a href="/wiki/Trypanosomatida" title="Trypanosomatida">trypanosomes</a>.<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> This is the basis for the use of some antifungals against West African <a href="/wiki/African_trypanosomiasis" title="African trypanosomiasis">sleeping sickness</a>. </p><p><a href="/wiki/Amphotericin_B" title="Amphotericin B">Amphotericin B</a>, an antifungal drug, targets ergosterol. It binds physically to ergosterol within the membrane, thus creating a polar pore in fungal membranes. This causes ions (predominantly <a href="/wiki/Potassium" title="Potassium">potassium</a> and <a href="/wiki/Hydron_(chemistry)" title="Hydron (chemistry)">hydrons</a>) and other molecules to leak out, which will kill the cell.<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> Amphotericin B has been replaced by safer agents in most circumstances, but is still used, despite its side effects, for life-threatening fungal or protozoan infections. </p><p><a href="/wiki/Fluconazole" title="Fluconazole">Fluconazole</a>, <a href="/wiki/Miconazole" title="Miconazole">miconazole</a>, <a href="/wiki/Itraconazole" title="Itraconazole">itraconazole</a>, <a href="/wiki/Clotrimazole" title="Clotrimazole">clotrimazole</a>, and <a href="/wiki/Myclobutanil" title="Myclobutanil">myclobutanil</a> work in a different way, inhibiting synthesis of ergosterol from <a href="/wiki/Lanosterol" title="Lanosterol">lanosterol</a> by interfering with <a href="/wiki/Lanosterol_14_alpha-demethylase" title="Lanosterol 14 alpha-demethylase">14α-demethylase</a>.<sup id="cite_ref-lv_6-0" class="reference"><a href="#cite_note-lv-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> Ergosterol is a smaller molecule than lanosterol; it is synthesized by combining two molecules of farnesyl pyrophosphate, a 15-carbon-long terpenoid, into lanosterol, which has 30 carbons. Then, two methyl groups are removed, making ergosterol. The "azole" class of antifungal agents <a href="/wiki/Enzyme_inhibitor" title="Enzyme inhibitor">inhibit</a> the enzyme that performs these <a href="/wiki/Demethylation" title="Demethylation">demethylation</a> steps in the biosynthetic pathway between lanosterol and ergosterol.<sup id="cite_ref-lv_6-1" class="reference"><a href="#cite_note-lv-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Target_for_antiprotozoal_drugs">Target for antiprotozoal drugs</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ergosterol&action=edit&section=3" title="Edit section: Target for antiprotozoal drugs"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Some protozoa, including <i><a href="/wiki/Trichomonas" title="Trichomonas">Trichomonas</a></i> and <i><a href="/wiki/Leishmania" title="Leishmania">Leishmania</a></i> are inhibited by drugs that target ergosterol synthesis and function<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> <div class="mw-heading mw-heading2"><h2 id="As_a_vitamin_D2_precursor">As a vitamin D<sub>2</sub> precursor</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ergosterol&action=edit&section=4" title="Edit section: As a vitamin D2 precursor"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Ergosterol is a <a href="/wiki/Provitamin" title="Provitamin">biological precursor</a> of <a href="/wiki/Ergocalciferol" title="Ergocalciferol">vitamin D<sub>2</sub></a>, the chemical name of which is <a href="/wiki/Ergocalciferol" title="Ergocalciferol">ergocalciferol</a>. Exposure of <a href="/wiki/Agaricus_bisporus" title="Agaricus bisporus">white button mushrooms</a> to <a href="/wiki/Ultraviolet_light" class="mw-redirect" title="Ultraviolet light">UV-C irradiation</a> produces time-dependent increases in vitamin D2 concentrations in the mushrooms.<sup id="cite_ref-Koyy_8-0" class="reference"><a href="#cite_note-Koyy-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Hirsch_10-0" class="reference"><a href="#cite_note-Hirsch-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> Fungi are grown industrially to enable ergosterol <a href="/wiki/Extract" title="Extract">extraction</a> and preparation as a powder for sale as a vitamin D<sub>2</sub> <a href="/wiki/Dietary_supplement" title="Dietary supplement">dietary supplement</a> and <a href="/wiki/Food_additive" title="Food additive">food additive</a>.<sup id="cite_ref-Koyy_8-1" class="reference"><a href="#cite_note-Koyy-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Hirsch_10-1" class="reference"><a href="#cite_note-Hirsch-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p><p>Preparations of irradiated ergosterol containing a mixture of previtamin and vitamin D<sub>2</sub> were called <i>viosterol</i> in the 1930s.<sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Toxicity">Toxicity</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ergosterol&action=edit&section=5" title="Edit section: Toxicity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Ergosterol powder is an irritant to skin, eyes, and the respiratory tract. Ingestion of large amounts can cause <a href="/wiki/Hypercalcemia" class="mw-redirect" title="Hypercalcemia">hypercalcemia</a>, which (if prolonged) can lead to calcium salt deposits in the soft tissues and kidneys.<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ergosterol&action=edit&section=6" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Mushrooms_and_vitamin_D" class="mw-redirect" title="Mushrooms and vitamin D">Mushrooms and vitamin D</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=Ergosterol&action=edit&section=7" 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 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href="https://ui.adsabs.harvard.edu/abs/2010PLoSO...510899W">2010PLoSO...510899W</a>. <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/10.1371%2Fjournal.pone.0010899">10.1371/journal.pone.0010899</a></span>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2878339">2878339</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/20526375">20526375</a>.</cite><span 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.navbox{display:none!important}}</style><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"></div><div role="navigation" class="navbox" aria-labelledby="Vitamins_(A11)" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><style data-mw-deduplicate="TemplateStyles:r1239400231">.mw-parser-output .navbar{display:inline;font-size:88%;font-weight:normal}.mw-parser-output .navbar-collapse{float:left;text-align:left}.mw-parser-output .navbar-boxtext{word-spacing:0}.mw-parser-output .navbar ul{display:inline-block;white-space:nowrap;line-height:inherit}.mw-parser-output .navbar-brackets::before{margin-right:-0.125em;content:"[ "}.mw-parser-output .navbar-brackets::after{margin-left:-0.125em;content:" ]"}.mw-parser-output .navbar li{word-spacing:-0.125em}.mw-parser-output .navbar a>span,.mw-parser-output .navbar a>abbr{text-decoration:inherit}.mw-parser-output .navbar-mini abbr{font-variant:small-caps;border-bottom:none;text-decoration:none;cursor:inherit}.mw-parser-output .navbar-ct-full{font-size:114%;margin:0 7em}.mw-parser-output .navbar-ct-mini{font-size:114%;margin:0 4em}html.skin-theme-clientpref-night .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}@media(prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}}@media print{.mw-parser-output .navbar{display:none!important}}</style><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Vitamins" title="Template:Vitamins"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Vitamins" title="Template talk:Vitamins"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Vitamins" title="Special:EditPage/Template:Vitamins"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Vitamins_(A11)" style="font-size:114%;margin:0 4em"><a href="/wiki/Vitamin" title="Vitamin">Vitamins</a> (<a href="/wiki/ATC_code_A11" title="ATC code A11">A11</a>)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">Fat <br />soluble</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Vitamin_A" title="Vitamin A">A</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/%CE%91-Carotene" title="Α-Carotene">α-Carotene</a></li> <li><a href="/wiki/%CE%92-Carotene" title="Β-Carotene">β-Carotene</a></li> <li><a href="/wiki/Retinol" title="Retinol">Retinol</a><sup>#</sup></li> <li><a href="/wiki/Tretinoin" title="Tretinoin">Tretinoin</a><sup>#</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Vitamin_D" title="Vitamin D">D</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>D<sub>2</sub> <ul><li><a class="mw-selflink selflink">Ergosterol</a></li> <li><a href="/wiki/Ergocalciferol" title="Ergocalciferol">Ergocalciferol</a><sup>#</sup></li></ul></li> <li>D<sub>3</sub> <ul><li><a href="/wiki/7-Dehydrocholesterol" title="7-Dehydrocholesterol">7-Dehydrocholesterol</a></li> <li><a href="/wiki/Previtamin_D3" title="Previtamin D3">Previtamin D<sub>3</sub></a></li> <li><a href="/wiki/Cholecalciferol" title="Cholecalciferol">Cholecalciferol</a><sup>#</sup></li> <li><a href="/wiki/Calcifediol" title="Calcifediol">25-hydroxycholecalciferol</a></li> <li><a href="/wiki/Calcitriol" title="Calcitriol">Calcitriol (1,25-dihydroxycholecalciferol)</a></li> <li><a href="/wiki/Calcitroic_acid" title="Calcitroic acid">Calcitroic acid</a></li></ul></li> <li>D<sub>4</sub> <ul><li><a href="/wiki/22-Dihydroergocalciferol" title="22-Dihydroergocalciferol">Dihydroergocalciferol</a></li></ul></li> <li><a href="/wiki/Vitamin_D5" title="Vitamin D5">D<sub>5</sub></a></li> <li>D analogues <ul><li><a href="/wiki/Alfacalcidol" title="Alfacalcidol">Alfacalcidol</a></li> <li><a href="/wiki/Dihydrotachysterol" title="Dihydrotachysterol">Dihydrotachysterol</a></li> <li><a href="/wiki/Calcipotriol" title="Calcipotriol">Calcipotriol</a></li> <li><a href="/wiki/Tacalcitol" title="Tacalcitol">Tacalcitol</a></li> <li><a href="/wiki/Paricalcitol" title="Paricalcitol">Paricalcitol</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Vitamin_E" title="Vitamin E">E</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/Tocopherol" title="Tocopherol">Tocopherol</a> <ul><li><a href="/wiki/%CE%91-Tocopherol" title="Α-Tocopherol">Alpha</a></li> <li><a href="/wiki/%CE%92-Tocopherol" title="Β-Tocopherol">Beta</a></li> <li><a href="/wiki/%CE%93-Tocopherol" title="Γ-Tocopherol">Gamma</a></li> <li><a href="/wiki/%CE%94-Tocopherol" title="Δ-Tocopherol">Delta</a></li></ul></li> <li><a href="/wiki/Tocotrienol" title="Tocotrienol">Tocotrienol</a> <ul><li><a href="/wiki/%CE%91-Tocotrienol" title="Α-Tocotrienol">Alpha</a></li> <li><a href="/wiki/%CE%92-Tocotrienol" title="Β-Tocotrienol">Beta</a></li> <li><a href="/wiki/%CE%93-Tocotrienol" title="Γ-Tocotrienol">Gamma</a></li> <li>Delta</li></ul></li> <li><a href="/wiki/Tocofersolan" title="Tocofersolan">Tocofersolan</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Vitamin_K" title="Vitamin K">K</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/1,4-Naphthoquinone" title="1,4-Naphthoquinone">Naphthoquinone</a></li> <li><a href="/wiki/Phytomenadione" title="Phytomenadione">Phylloquinone (K<sub>1</sub>)</a><sup>#</sup></li> <li><a href="/wiki/Vitamin_K2" title="Vitamin K2">Menaquinones (K<sub>2</sub>)</a></li> <li><a href="/wiki/Menadione" title="Menadione">Menadione (K<sub>3</sub>)</a><sup>‡</sup></li> <li><a href="/wiki/Vitamin_K4" class="mw-redirect" title="Vitamin K4">Various (K<sub>4</sub>)</a></li> <li><a href="/wiki/4-Amino-2-methyl-1-naphthol" title="4-Amino-2-methyl-1-naphthol">4-Amino-2-methyl-1-naphthol (K<sub>5</sub>)</a><sup>‡</sup></li> <li><a href="/wiki/2-Methylnaphthalene-1,4-diamine" title="2-Methylnaphthalene-1,4-diamine">2-Methylnaphthalene-1,4-diamine (K<sub>6</sub>)</a></li> <li><a href="/wiki/4-Amino-3-methyl-1-naphthol" title="4-Amino-3-methyl-1-naphthol">4-Amino-3-methyl-1-naphthol (K<sub>7</sub>)</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Water <br />soluble</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/B_vitamins" title="B vitamins">B</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>B<sub>1</sub> <ul><li><a href="/wiki/Thiamine" title="Thiamine">Thiamine</a><sup>#</sup></li></ul></li> <li><a href="/wiki/Vitamin_B1_analogues" title="Vitamin B1 analogues">B<sub>1</sub> analogues</a> <ul><li><a href="/wiki/Acefurtiamine" title="Acefurtiamine">Acefurtiamine</a></li> <li><a href="/wiki/Allithiamine" title="Allithiamine">Allithiamine</a></li> <li><a href="/wiki/Benfotiamine" title="Benfotiamine">Benfotiamine</a></li> <li><a href="/wiki/Fursultiamine" title="Fursultiamine">Fursultiamine</a></li> <li><a href="/wiki/Octotiamine" title="Octotiamine">Octotiamine</a></li> <li><a href="/wiki/Prosultiamine" title="Prosultiamine">Prosultiamine</a></li> <li><a href="/wiki/Sulbutiamine" title="Sulbutiamine">Sulbutiamine</a></li></ul></li> <li>B<sub>2</sub> <ul><li><a href="/wiki/Riboflavin" title="Riboflavin">Riboflavin</a><sup>#</sup></li></ul></li> <li><a href="/wiki/Vitamin_B3" title="Vitamin B3">B<sub>3</sub></a> <ul><li><a href="/wiki/Niacin" title="Niacin">Niacin</a></li> <li><a href="/wiki/Nicotinamide" title="Nicotinamide">Niacinamide</a><sup>#</sup></li></ul></li> <li>B<sub>5</sub> <ul><li><a href="/wiki/Pantothenic_acid" title="Pantothenic acid">Pantothenic acid</a></li> <li><a href="/wiki/Panthenol" title="Panthenol">Dexpanthenol</a></li> <li><a href="/wiki/Pantethine" title="Pantethine">Pantethine</a></li></ul></li> <li><a href="/wiki/Vitamin_B6" title="Vitamin B6">B<sub>6</sub></a> <ul><li><a href="/wiki/Pyridoxine" title="Pyridoxine">Pyridoxine</a><sup>#</sup>, <a href="/wiki/Pyridoxal_phosphate" title="Pyridoxal phosphate">Pyridoxal phosphate</a></li> <li><a href="/wiki/Pyridoxamine" title="Pyridoxamine">Pyridoxamine</a></li> <li><a href="/wiki/Pyritinol" title="Pyritinol">Pyritinol</a></li></ul></li> <li>B<sub>7</sub> <ul><li><a href="/wiki/Biotin" title="Biotin">Biotin</a></li></ul></li> <li>B<sub>9</sub> <ul><li><a href="/wiki/Folate" title="Folate">Folic acid</a><sup>#</sup></li> <li><a href="/wiki/Dihydrofolic_acid" title="Dihydrofolic acid">Dihydrofolic acid</a></li> <li><a href="/wiki/Folinic_acid" title="Folinic acid">Folinic acid</a></li> <li><a href="/wiki/Levomefolic_acid" title="Levomefolic acid">Levomefolic acid</a></li></ul></li> <li><a href="/wiki/Vitamin_B12" title="Vitamin B12">B<sub>12</sub></a> <ul><li><a href="/wiki/Adenosylcobalamin" title="Adenosylcobalamin">Adenosylcobalamin</a></li> <li><a href="/wiki/Cyanocobalamin" title="Cyanocobalamin">Cyanocobalamin</a></li> <li><a href="/wiki/Hydroxocobalamin" title="Hydroxocobalamin">Hydroxocobalamin</a><sup>#</sup></li> <li><a href="/wiki/Methylcobalamin" title="Methylcobalamin">Methylcobalamin</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Vitamin_C" title="Vitamin C">C</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/Vitamin_C" title="Vitamin C">Ascorbic acid</a><sup>#</sup></li> <li><a href="/wiki/Dehydroascorbic_acid" title="Dehydroascorbic acid">Dehydroascorbic acid</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Combinations</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Multivitamin" title="Multivitamin">Multivitamins</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"><div class="hlist"> <ul><li><sup>#</sup><a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">WHO-EM</a></li> <li><sup>‡</sup><a href="/wiki/List_of_withdrawn_drugs" title="List of withdrawn drugs">Withdrawn</a> from market</li> <li><a href="/wiki/Clinical_trial" title="Clinical trial">Clinical trials</a>: <ul><li><sup>†</sup><a href="/wiki/Phases_of_clinical_research#Phase_III" title="Phases of clinical research">Phase III</a></li> <li><sup>§</sup>Never to phase III</li></ul></li></ul> </div></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Cholesterol_and_steroid_metabolic_intermediates" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Cholesterol_and_steroid_intermediates" title="Template:Cholesterol and steroid intermediates"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Cholesterol_and_steroid_intermediates" title="Template talk:Cholesterol and steroid intermediates"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Cholesterol_and_steroid_intermediates" title="Special:EditPage/Template:Cholesterol and steroid intermediates"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Cholesterol_and_steroid_metabolic_intermediates" style="font-size:114%;margin:0 4em"><a href="/wiki/Cholesterol" title="Cholesterol">Cholesterol</a> and <a href="/wiki/Steroid" title="Steroid">steroid</a> <a href="/wiki/Metabolic_intermediate" title="Metabolic intermediate">metabolic intermediates</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Mevalonate_pathway" title="Mevalonate pathway">Mevalonate pathway</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">to <a href="/wiki/HMG-CoA" title="HMG-CoA">HMG-CoA</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/Acetyl-CoA" title="Acetyl-CoA">Acetyl-CoA</a></li> <li><a href="/wiki/Acetoacetyl-CoA" title="Acetoacetyl-CoA">Acetoacetyl-CoA</a></li> <li><a href="/wiki/Beta-Hydroxy_beta-methylbutyric_acid" class="mw-redirect" title="Beta-Hydroxy beta-methylbutyric acid">HMB</a></li> <li><a href="/wiki/Beta-Hydroxy_beta-methylbutyryl-CoA" class="mw-redirect" title="Beta-Hydroxy beta-methylbutyryl-CoA">HMB-CoA</a></li> <li><a href="/wiki/HMG-CoA" title="HMG-CoA">HMG-CoA</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Ketone_bodies" title="Ketone bodies">Ketone bodies</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/Acetone" title="Acetone">Acetone</a></li> <li><a href="/wiki/Acetoacetic_acid" title="Acetoacetic acid">Acetoacetic acid</a></li> <li><a href="/wiki/Beta-Hydroxybutyric_acid" class="mw-redirect" title="Beta-Hydroxybutyric acid">β-Hydroxybutyric acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">to <a href="/wiki/Dimethylallyl_pyrophosphate" title="Dimethylallyl pyrophosphate">DMAPP</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/Mevalonic_acid" title="Mevalonic acid">Mevalonic acid</a></li> <li><a href="/wiki/Phosphomevalonic_acid" title="Phosphomevalonic acid">Phosphomevalonic acid</a></li> <li><a href="/wiki/5-Diphosphomevalonic_acid" title="5-Diphosphomevalonic acid">5-Diphosphomevalonic acid</a></li> <li><a href="/wiki/Isopentenyl_pyrophosphate" title="Isopentenyl pyrophosphate">Isopentenyl pyrophosphate</a></li> <li><a href="/wiki/Dimethylallyl_pyrophosphate" title="Dimethylallyl pyrophosphate">Dimethylallyl pyrophosphate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Geranyl-</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/Geranyl_pyrophosphate" title="Geranyl pyrophosphate">Geranyl pyrophosphate</a></li> <li><a href="/wiki/Geranylgeranyl_pyrophosphate" title="Geranylgeranyl pyrophosphate">Geranylgeranyl pyrophosphate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Carotenoid" title="Carotenoid">Carotenoid</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/Prephytoene_diphosphate" title="Prephytoene diphosphate">Prephytoene diphosphate</a></li> <li><a href="/wiki/Phytoene" title="Phytoene">Phytoene</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Non-mevalonate_pathway" title="Non-mevalonate pathway">Non-mevalonate pathway</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/1-Deoxy-D-xylulose_5-phosphate" title="1-Deoxy-D-xylulose 5-phosphate">DOXP</a></li> <li><a href="/wiki/2-C-methylerythritol_4-phosphate" class="mw-redirect" title="2-C-methylerythritol 4-phosphate">MEP</a></li> <li><a href="/wiki/4-diphosphocytidyl-2-C-methylerythritol" class="mw-redirect" title="4-diphosphocytidyl-2-C-methylerythritol">CDP-ME</a></li> <li><a href="/wiki/4-diphosphocytidyl-2-C-methyl-D-erythritol_2-phosphate" class="mw-redirect" title="4-diphosphocytidyl-2-C-methyl-D-erythritol 2-phosphate">CDP-MEP</a></li> <li><a href="/wiki/2-C-methyl-D-erythritol_2,4-cyclopyrophosphate" class="mw-redirect" title="2-C-methyl-D-erythritol 2,4-cyclopyrophosphate">MEcPP</a></li> <li><a href="/wiki/(E)-4-Hydroxy-3-methyl-but-2-enyl_pyrophosphate" title="(E)-4-Hydroxy-3-methyl-but-2-enyl pyrophosphate">HMB-PP</a></li> <li><a href="/wiki/Isopentenyl_pyrophosphate" title="Isopentenyl pyrophosphate">IPP</a></li> <li><a href="/wiki/Dimethylallyl_pyrophosphate" title="Dimethylallyl pyrophosphate">DMAPP</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">To <a href="/wiki/Cholesterol" title="Cholesterol">Cholesterol</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Farnesyl_pyrophosphate" title="Farnesyl pyrophosphate">Farnesyl pyrophosphate</a></li> <li><a href="/wiki/Squalene" title="Squalene">Squalene</a></li> <li><a href="/wiki/2,3-Oxidosqualene" title="2,3-Oxidosqualene">2,3-Oxidosqualene</a></li> <li><a href="/wiki/Lanosterol" title="Lanosterol">Lanosterol</a></li></ul> <ul><li><a href="/wiki/Lanosterol" title="Lanosterol">Lanosterol</a></li> <li><a href="/w/index.php?title=14-demethyllanosterol&action=edit&redlink=1" class="new" title="14-demethyllanosterol (page does not exist)">14-demethyllanosterol</a></li> <li><a href="/w/index.php?title=4alpha-Methylzymosterol&action=edit&redlink=1" class="new" title="4alpha-Methylzymosterol (page does not exist)">4alpha-Methylzymosterol</a></li> <li><a href="/w/index.php?title=Zymosterone&action=edit&redlink=1" class="new" title="Zymosterone (page does not exist)">Zymosterone</a></li> <li><a href="/wiki/Zymosterol" title="Zymosterol">Zymosterol</a></li></ul> <ul><li><a href="/wiki/Zymosterol" title="Zymosterol">Zymosterol</a></li> <li><a href="/w/index.php?title=Zymostenol&action=edit&redlink=1" class="new" title="Zymostenol (page does not exist)">Zymostenol</a></li> <li><a href="/wiki/Lathosterol" title="Lathosterol">Lathosterol</a></li> <li><a href="/wiki/7-Dehydrocholesterol" title="7-Dehydrocholesterol">7-Dehydrocholesterol</a></li> <li><a href="/wiki/Cholesterol" title="Cholesterol">Cholesterol</a></li></ul> <ul><li><a href="/wiki/Zymosterol" title="Zymosterol">Zymosterol</a></li> <li><a href="/w/index.php?title=Cholesta-7,24-dien-3-ol&action=edit&redlink=1" class="new" title="Cholesta-7,24-dien-3-ol (page does not exist)">Cholesta-7,24-dien-3-ol</a></li> <li><a href="/wiki/7-Dehydrodesmosterol" title="7-Dehydrodesmosterol">7-Dehydrodesmosterol</a></li> <li><a href="/wiki/Desmosterol" title="Desmosterol">Desmosterol</a></li> <li><a href="/wiki/Cholesterol" title="Cholesterol">Cholesterol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">From <a href="/wiki/Cholesterol" title="Cholesterol">Cholesterol</a> <br />to <a href="/wiki/Steroid" title="Steroid">Steroid hormones</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/22R-Hydroxycholesterol" title="22R-Hydroxycholesterol">22<i>R</i>-Hydroxycholesterol</a></li> <li><a href="/wiki/20%CE%B1,22R-Dihydroxycholesterol" title="20α,22R-Dihydroxycholesterol">20α,22<i>R</i>-Dihydroxycholesterol</a></li> <li>See <a href="/wiki/Template:Steroid_hormones" title="Template:Steroid hormones">here</a> instead.</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Nonhuman</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">To <a href="/wiki/Sitosterol" class="mw-redirect" title="Sitosterol">Sitosterol</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/Cycloartenol" title="Cycloartenol">Cycloartenol</a></li> <li><a href="/w/index.php?title=Cycloeucalenol&action=edit&redlink=1" class="new" title="Cycloeucalenol (page does not exist)">Cycloeucalenol</a></li> <li><a href="/wiki/Obtusifoliol" title="Obtusifoliol">Obtusifoliol</a></li> <li><a href="/wiki/4%CE%B1-methylfecosterol" class="mw-redirect" title="4α-methylfecosterol">4α-methylfecosterol</a></li> <li><a href="/wiki/Isofucosterol" title="Isofucosterol">Isofucosterol</a></li> <li><a href="/wiki/24-Methylenelophenol" title="24-Methylenelophenol">24-Methylenelophenol</a></li> <li><a href="/wiki/Sitosterol" class="mw-redirect" title="Sitosterol">Sitosterol</a></li> <li>More <a href="/wiki/Phytosterol" title="Phytosterol">Phytosterols</a> see <a href="/wiki/Template:Steroid_hormones" title="Template:Steroid hormones">here</a> instead.</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">To <a href="/wiki/Ergocalciferol" title="Ergocalciferol">Ergocalciferol</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/Fecosterol" title="Fecosterol">Fecosterol</a></li> <li><a href="/wiki/Episterol" title="Episterol">Episterol</a></li> <li><a href="/wiki/Ergostatrienol" class="mw-redirect" title="Ergostatrienol">Ergostatrienol</a></li> <li><a href="/w/index.php?title=Ergostatetraenol&action=edit&redlink=1" class="new" title="Ergostatetraenol (page does not exist)">Ergostatetraenol</a></li> <li><a class="mw-selflink selflink">Ergosterol</a></li> <li><a href="/wiki/Ergocalciferol" title="Ergocalciferol">Ergocalciferol</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Phytosterols" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Phytosterols" title="Template:Phytosterols"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Phytosterols" title="Template talk:Phytosterols"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Phytosterols" title="Special:EditPage/Template:Phytosterols"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Phytosterols" style="font-size:114%;margin:0 4em"><a href="/wiki/Phytosterol" title="Phytosterol">Phytosterols</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">C28</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Brassicasterol" title="Brassicasterol">Brassicasterol</a></li> <li><a href="/wiki/Campesterol" title="Campesterol">Campesterol</a></li> <li><a class="mw-selflink selflink">Ergosterol</a> (Vitamin D2)</li> <li><a href="/w/index.php?title=Ergostenol&action=edit&redlink=1" class="new" title="Ergostenol (page does not exist)">Ergostenol</a></li> <li><a href="/wiki/Ergostatrienol" class="mw-redirect" title="Ergostatrienol">Ergostatrienol</a></li> <li><a href="/w/index.php?title=Ergostadienol&action=edit&redlink=1" class="new" title="Ergostadienol (page does not exist)">Ergostadienol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">C29</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Avenasterol" title="Avenasterol">δ-7-avenasterol</a></li> <li><a href="/wiki/Isofucosterol" title="Isofucosterol">δ-5-avenasterol</a></li> <li><a href="/wiki/Beta-Sitosterol" class="mw-redirect" title="Beta-Sitosterol">β-Sitosterol</a></li> <li><a href="/w/index.php?title=%CE%94-7-stigmasterol&action=edit&redlink=1" class="new" title="Δ-7-stigmasterol (page does not exist)">δ-7-stigmasterol</a></li> <li><a href="/wiki/Momordenol" title="Momordenol">Momordenol</a></li> <li><a href="/wiki/Spinasterol" title="Spinasterol">Spinasterol</a></li> <li><a href="/wiki/Stigmastanol" title="Stigmastanol">Stigmastanol</a></li> <li><a href="/w/index.php?title=Stigmastenol&action=edit&redlink=1" class="new" title="Stigmastenol (page does not exist)">Stigmastenol</a></li> <li><a href="/w/index.php?title=Stigmastadienol&action=edit&redlink=1" class="new" title="Stigmastadienol (page does not exist)">Stigmastadienol</a></li> <li><a href="/w/index.php?title=Stigmastadienone&action=edit&redlink=1" class="new" title="Stigmastadienone (page does not exist)">Stigmastadienone</a></li> <li><a href="/wiki/Stigmasterol" title="Stigmasterol">Stigmasterol</a></li> <li><a href="/w/index.php?title=Stigmastenone&action=edit&redlink=1" class="new" title="Stigmastenone (page does not exist)">Stigmastenone</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"><style data-mw-deduplicate="TemplateStyles:r1038841319">.mw-parser-output .tooltip-dotted{border-bottom:1px dotted;cursor:help}</style></div><div 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