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class="vector-toc-numb">2</span> <span>Biological occurrence</span> </div> </a> <ul id="toc-Biological_occurrence-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Biosynthesis" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Biosynthesis"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Biosynthesis</span> </div> </a> <ul id="toc-Biosynthesis-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Preservation" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Preservation"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Preservation</span> </div> </a> <ul id="toc-Preservation-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Use_as_a_Biomarker" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Use_as_a_Biomarker"> <div 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class="vector-toc-numb">5.2</span> <span>Peruvian Shelf</span> </div> </a> <ul id="toc-Peruvian_Shelf-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Measurement_techniques" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Measurement_techniques"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Measurement techniques</span> </div> </a> <button aria-controls="toc-Measurement_techniques-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Measurement techniques subsection</span> </button> <ul id="toc-Measurement_techniques-sublist" class="vector-toc-list"> <li id="toc-GC-MS" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#GC-MS"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.1</span> <span>GC-MS</span> </div> </a> <ul id="toc-GC-MS-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Ozonolysis" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Ozonolysis"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.2</span> <span>Ozonolysis</span> </div> </a> <ul id="toc-Ozonolysis-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>See also</span> </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span class="vector-dropdown-label-text">Toggle the table of contents</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Desmosterol</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. 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href="https://ko.wikipedia.org/wiki/%EB%8D%B0%EC%8A%A4%EB%AA%A8%EC%8A%A4%ED%85%8C%EB%A1%A4" title="데스모스테롤 – Korean" lang="ko" hreflang="ko" data-title="데스모스테롤" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%87%E3%82%B9%E3%83%A2%E3%82%B9%E3%83%86%E3%83%AD%E3%83%BC%E3%83%AB" title="デスモステロール – Japanese" lang="ja" hreflang="ja" data-title="デスモステロール" 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-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Desmosterol" title="Desmosterol – Portuguese" lang="pt" hreflang="pt" data-title="Desmosterol" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Dezmosterol" title="Dezmosterol – Serbian" lang="sr" hreflang="sr" data-title="Dezmosterol" 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/Dezmosterol" title="Dezmosterol – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Dezmosterol" 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-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E9%93%BE%E7%94%BE%E9%86%87" title="链甾醇 – Chinese" lang="zh" hreflang="zh" data-title="链甾醇" data-language-autonym="中文" data-language-local-name="Chinese" 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The present address (URL) is a <a href="/wiki/Help:Permanent_link" title="Help:Permanent link">permanent link</a> to this version.</b></p><div id="revision-info-current-plain" style="display: none;">Revision as of 21:26, 12 March 2024 by <a href="/wiki/User:Chris_Capoccia" class="mw-userlink" title="User:Chris Capoccia" data-mw-revid="1213406819"><bdi>Chris Capoccia</bdi></a> <span class="mw-usertoollinks">(<a href="/wiki/User_talk:Chris_Capoccia" class="mw-usertoollinks-talk" title="User talk:Chris Capoccia">talk</a> | <a href="/wiki/Special:Contributions/Chris_Capoccia" class="mw-usertoollinks-contribs" title="Special:Contributions/Chris Capoccia">contribs</a>)</span></div></div><div id="mw-revision-nav">(<a href="/w/index.php?title=Desmosterol&diff=prev&oldid=1213406819" title="Desmosterol">diff</a>) <a href="/w/index.php?title=Desmosterol&direction=prev&oldid=1213406819" title="Desmosterol">← Previous revision</a> | Latest revision (diff) | Newer revision → (diff)</div></div></div></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" 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>Desmosterol </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Desmosterol.png" class="mw-file-description"><img alt="Skeletal formula of desmosterol" src="//upload.wikimedia.org/wikipedia/commons/thumb/3/3c/Desmosterol.png/220px-Desmosterol.png" decoding="async" width="220" height="158" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/3c/Desmosterol.png/330px-Desmosterol.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/3c/Desmosterol.png/440px-Desmosterol.png 2x" data-file-width="1237" data-file-height="888" /></a></span> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Desmosterol_3D_ball.png" class="mw-file-description"><img alt="Ball-and-stick model of the desmosterol molecule" src="//upload.wikimedia.org/wikipedia/commons/thumb/0/00/Desmosterol_3D_ball.png/220px-Desmosterol_3D_ball.png" decoding="async" width="220" height="132" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/00/Desmosterol_3D_ball.png/330px-Desmosterol_3D_ball.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/00/Desmosterol_3D_ball.png/440px-Desmosterol_3D_ball.png 2x" data-file-width="2000" data-file-height="1202" /></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;">Cholesta-5,24-dien-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>S</i>,3b<i>S</i>,7<i>S</i>,9a<i>R</i>,9b<i>S</i>,11a<i>R</i>)-9a,11a-Dimethyl-1-[(2<i>R</i>)-6-methylhept-5-en-2-yl]-2,3,3a,3b,4,6,7,8,9,9a,9b,10,11,11a-tetradecahydro-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=313-04-2">313-04-2</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%5BC%40%40H%5D1%5BC%40H%5D%28CC%5BC%40%5D2%28%5BC%40H%5D1CC%5BC%40%40H%5D2%5BC%40H%5D%28C%29CC%5CC%3DC%28%2FC%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=17737">CHEBI:17737</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/chembl/explore/compound/ChEMBL455876">ChEMBL455876</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.388662.html">388662</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/100.005.671">100.005.671</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q3024529#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><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/IUPHAR/BPS" class="mw-redirect" title="IUPHAR/BPS">IUPHAR/BPS</a></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.guidetopharmacology.org"><a rel="nofollow" class="external text" href="http://www.guidetopharmacology.org/GRAC/LigandDisplayForward?tab=summary&ligandId=2748">2748</a></span></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/439577">439577</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/ANP93865R8">ANP93865R8</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/DTXSID10878676">DTXSID10878676</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q3024529#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/C27H44O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h7,9,19,21-25,28H,6,8,10-17H2,1-5H3/t19-,21+,22+,23-,24+,25+,26+,27-/m1/s1<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: AVSXSVCZWQODGV-DPAQBDIFSA-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/C27H44O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h7,9,19,21-25,28H,6,8,10-17H2,1-5H3/t19-,21+,22+,23-,24+,25+,26+,27-/m1/s1</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: AVSXSVCZWQODGV-DPAQBDIFBV</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[C@@H]1[C@H](CC[C@]2([C@H]1CC[C@@H]2[C@H](C)CC\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>27</sub>H<sub>44</sub>O  </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td>384.64 g/mol    </td></tr> <tr> <td>Appearance </td> <td>White powder </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>121.5 °C (250.7 °F; 394.6 K) </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="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/12px-Yes_check.svg.png" decoding="async" width="12" height="12" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/18px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/24px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span> <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=443583337&page2=Desmosterol">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>Desmosterol</b> (Cholesta-5,24-dien-3β-ol) is a <a href="/wiki/Lipid" title="Lipid">lipid</a> present in the membrane of <a href="/wiki/Phytoplankton" title="Phytoplankton">phytoplankton</a> and an intermediate product in cholesterol synthesis in mammal 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> Structurally, desmosterol has a similar backbone to <a href="/wiki/Cholesterol" title="Cholesterol">cholesterol</a>, with the exception of an additional double bond in the structure of desmosterol. </p><p>The similarity can be seen biologically through the synthesis of cholesterol in the human body, as desmosterol is the immediate precursor to cholesterol in the <a href="/w/index.php?title=Bloch_pathway&action=edit&redlink=1" class="new" title="Bloch pathway (page does not exist)">Bloch pathway</a>.<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> Desmosterol is accumulated in <a href="/wiki/Desmosterolosis" title="Desmosterolosis">desmosterolosis</a> and undergoes reduction with the catalyst <i><a href="/wiki/24-Dehydrocholesterol_reductase" title="24-Dehydrocholesterol reductase">24-dehydrocholesterol reductase</a></i> to form cholesterol.<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> </p><p>In 2014, desmosterol was named the <a href="/wiki/Molecule_of_the_Year" class="mw-redirect" title="Molecule of the Year">Molecule of the Year</a> 2012 by the International Society for Molecular and Cell Biology and Biotechnology Protocols and Researches (<a href="/wiki/ISMCBBPR" class="mw-redirect" title="ISMCBBPR">ISMCBBPR</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> </p> <figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Desmosterol_and_Cholesterol_Chemical_Structures.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/42/Desmosterol_and_Cholesterol_Chemical_Structures.svg/500px-Desmosterol_and_Cholesterol_Chemical_Structures.svg.png" decoding="async" width="500" height="137" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/42/Desmosterol_and_Cholesterol_Chemical_Structures.svg/750px-Desmosterol_and_Cholesterol_Chemical_Structures.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/42/Desmosterol_and_Cholesterol_Chemical_Structures.svg/1000px-Desmosterol_and_Cholesterol_Chemical_Structures.svg.png 2x" data-file-width="512" data-file-height="140" /></a><figcaption>Structure of cholesterol and its immediate precursor, desmosterol.</figcaption></figure> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Background">Background</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Desmosterol&action=edit&section=1" title="Edit section: Background"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Desmosterol is classified as a cholestadienol, a subgroup of a wider known group of <a href="/wiki/Sterol" title="Sterol">sterols</a>, which naturally occur in eukaryotes. The presence of desmosterol in oceans and lakes has the potential to diagnose <a href="/wiki/Anoxic_waters" title="Anoxic waters">anoxic</a> conditions and to study trends in steroid chemistry during the early stages of <a href="/wiki/Diagenesis" title="Diagenesis">diagenesis</a>.<sup id="cite_ref-:0_5-0" class="reference"><a href="#cite_note-:0-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> Desmosterol has been found in high yields in samples of <i>Rhizosolenia setigera</i> (Brightwell) in Western Svalbard,<sup id="cite_ref-:12_6-0" class="reference"><a href="#cite_note-:12-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> and from surface sediment off of the Peruvian Shelf sediment-water interface.<sup id="cite_ref-:0_5-1" class="reference"><a href="#cite_note-:0-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p><p>In 1955, desmosterol was first described and isolated from chick embryo sterol with a 2% yield and was postulated as being a biological precursor to cholesterol by Stokes et al.<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> The first known isolation of desmosterol in invertebrates was published in 1957 by Fagerlund and Idler.<sup id="cite_ref-:22_8-0" class="reference"><a href="#cite_note-:22-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> This new sterol was isolated in large amounts from <a href="/wiki/Balanus_glandula" title="Balanus glandula">balanus glandula</a>, a <a href="/wiki/Barnacle" title="Barnacle">barnacle</a> species found on the North American Pacific coast. Additionally, small amounts of desmosterol have been found in other crustaceans such as lobster and shrimp in the <i><a href="/wiki/Homarus_americanus" class="mw-redirect" title="Homarus americanus">homarus americanus</a></i> and <i><a href="/wiki/Pandalus_borealis" title="Pandalus borealis">pandalus borealis</a></i> species<b>.</b> This strengthens the conclusion that desmosterol must be created exogenously, as crustaceans have not been seen to <a href="/wiki/Biosynthesis" title="Biosynthesis">biosynthesise</a> sterols.<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> </p> <div class="mw-heading mw-heading2"><h2 id="Biological_occurrence">Biological occurrence</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Desmosterol&action=edit&section=2" title="Edit section: Biological occurrence"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Desmosterol has been largely found within a large population of marine invertebrates. Major sources include <a href="/wiki/Barnacle" title="Barnacle">barnacles</a>,<sup id="cite_ref-:22_8-1" class="reference"><a href="#cite_note-:22-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Red_algae" title="Red algae">red algae</a>,<sup id="cite_ref-:4_10-0" class="reference"><a href="#cite_note-:4-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Annelid" title="Annelid">annelida</a>,<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> and <a href="/wiki/Mollusca" title="Mollusca">molluscs</a>.<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> This has led to the idea of an <a href="/wiki/Exogenous" class="mw-redirect" title="Exogenous">exogenous</a> origin of desmosterol in phytoplankton. In 1967, desmosterol was also identified in large percentages in the red algae <a href="/wiki/Laurencia_pinnatifida" class="mw-redirect" title="Laurencia pinnatifida">Laurencia pinnatifida</a>, Polusiphonia nigrescens, <a href="/wiki/Porphyra_purpurea" title="Porphyra purpurea">Porphyra purpurea</a>, and <a href="/wiki/Palmaria_palmata" title="Palmaria palmata">Dulse (Rhodymenia palmata)</a> after previously having been undetected. </p><p>In the 1968 paper by Idler, Saito and Wiseman,<sup id="cite_ref-:4_10-1" class="reference"><a href="#cite_note-:4-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Palmaria_palmata" title="Palmaria palmata">dulse</a> samples were analysed and the sterols present were determined by <a href="/wiki/Gas_chromatography" title="Gas chromatography">gas liquid chromatography</a>. Samples were collected near Grand Manan Island, New York in 1964 and 1965, and showed a significant difference in the presence of desmosterol. Samples 1 and 2 were from the same source, as were samples 3 and 4, and all samples were harvested at different times. Samples 2, 3, and 4 had the major sterol as desmosterol, compared to sample 1, with the major sterol being cholesterol.<sup id="cite_ref-:4_10-2" class="reference"><a href="#cite_note-:4-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> This indicates a 70% difference in desmosterol composition in the sterol samples (1 and 2) over a period of one year. There has been no conclusive evidence to show whether seasonal variation of sterols in barnacles occur. </p> <figure class="mw-halign-none" typeof="mw:File/Thumb"><a href="/wiki/File:Sterol_composition_of_dulse_samples.pdf" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0d/Sterol_composition_of_dulse_samples.pdf/page1-500px-Sterol_composition_of_dulse_samples.pdf.jpg" decoding="async" width="500" height="204" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0d/Sterol_composition_of_dulse_samples.pdf/page1-750px-Sterol_composition_of_dulse_samples.pdf.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/0d/Sterol_composition_of_dulse_samples.pdf/page1-1000px-Sterol_composition_of_dulse_samples.pdf.jpg 2x" data-file-width="1016" data-file-height="414" /></a><figcaption>Sterol composition of dulse samples from Grand Manan Island, New York, with data taken from Idler's 1968 paper.<sup id="cite_ref-:4_10-3" class="reference"><a href="#cite_note-:4-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup></figcaption></figure> <div class="mw-heading mw-heading2"><h2 id="Biosynthesis">Biosynthesis</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Desmosterol&action=edit&section=3" title="Edit section: Biosynthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>There are two major pathways for cholesterol biosynthesis, being the Kandutsch-Russell and Bloch pathways.<sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> The Bloch pathway, named after <a href="/wiki/Konrad_Emil_Bloch" title="Konrad Emil Bloch">Konrad Bloch</a>, occurs naturally alongside the <a href="/wiki/Mevalonate_pathway" title="Mevalonate pathway">mevalonate</a> pathway in humans within the cell. The discovery of this pathway led Bloch, joint with <a href="/wiki/Feodor_Lynen" title="Feodor Lynen">Feodor Lynen</a>, to receive a Nobel Prize in Physiology or Medicine in 1964. The award was awarded “for their discoveries concerning the mechanism and regulation of the cholesterol and fatty acid metabolism”.<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Desmosterol_to_cholesterol_Bloch_pathway.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b5/Desmosterol_to_cholesterol_Bloch_pathway.svg/810px-Desmosterol_to_cholesterol_Bloch_pathway.svg.png" decoding="async" width="810" height="176" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b5/Desmosterol_to_cholesterol_Bloch_pathway.svg/1215px-Desmosterol_to_cholesterol_Bloch_pathway.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b5/Desmosterol_to_cholesterol_Bloch_pathway.svg/1620px-Desmosterol_to_cholesterol_Bloch_pathway.svg.png 2x" data-file-width="512" data-file-height="111" /></a><figcaption>Synthetic pathway from desmosterol to cholesterol</figcaption></figure> <div class="mw-heading mw-heading2"><h2 id="Preservation">Preservation</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Desmosterol&action=edit&section=4" title="Edit section: Preservation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Desmosterol has been seen to be present in <a href="/wiki/Marine_sponge" class="mw-redirect" title="Marine sponge">marine sponges</a> as a <a href="/wiki/Biomarkers_of_aging" title="Biomarkers of aging">biomarker</a>. However, bacterial symbiont sterol 24-C-methyltransferases is capable of the alkylation of desmosterol to other sponge biomarkers, 24-isopropenylcholesterol, and 24-isopropylidenecholesterol.<sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> There is insignificant data which shows that desmosterol has good <a href="/wiki/Preservation_potential" class="mw-redirect" title="Preservation potential">preservation potential</a>. </p> <div class="mw-heading mw-heading2"><h2 id="Use_as_a_Biomarker">Use as a Biomarker</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Desmosterol&action=edit&section=5" title="Edit section: Use as a Biomarker"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>As a biomarker, desmosterol is important for the <i>Chaetoceros calcitrans</i><sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> and <i>R. setigera</i> and <i>N. closterium</i><sup id="cite_ref-:5_17-0" class="reference"><a href="#cite_note-:5-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Diatom" title="Diatom">diatoms</a> as well as <a href="/wiki/Red_algae" title="Red algae"><i>Rhodophyceae</i></a>.<sup id="cite_ref-18" class="reference"><a href="#cite_note-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> However, desmosterol has the potential to be used as a <a href="/wiki/Taxonomy" title="Taxonomy">taxonomic</a> marker for diatoms where it exists as the dominant sterol, such as in <i>Rhizosolenia</i>.<sup id="cite_ref-:5_17-1" class="reference"><a href="#cite_note-:5-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Balsfjorden,_Northern_Norway"><span id="Balsfjorden.2C_Northern_Norway"></span>Balsfjorden, Northern Norway</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Desmosterol&action=edit&section=6" title="Edit section: Balsfjorden, Northern Norway"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Desmosterol has been used as a biomarker for the presence of <a href="/wiki/Copepod" title="Copepod">copepods</a>. The phytoplankton bloom of <i>P. pouchetii</i> and <i>Thalassiosira decipiens</i> resulted in low amounts of desmosterol at maximum chlorophyll levels, indicating the low abundance and efficient removal of copepods in these phytoplankton.<sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-halign-none" typeof="mw:File/Thumb"><a href="/wiki/File:Sterol_composition_at_maximum_chlorophuyll.pdf" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/62/Sterol_composition_at_maximum_chlorophuyll.pdf/page1-550px-Sterol_composition_at_maximum_chlorophuyll.pdf.jpg" decoding="async" width="550" height="418" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/62/Sterol_composition_at_maximum_chlorophuyll.pdf/page1-825px-Sterol_composition_at_maximum_chlorophuyll.pdf.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/62/Sterol_composition_at_maximum_chlorophuyll.pdf/page1-1100px-Sterol_composition_at_maximum_chlorophuyll.pdf.jpg 2x" data-file-width="945" data-file-height="718" /></a><figcaption>Biomarker patterns at maximum chlorophyll in Balsfjorden. (1) 24-norcholesta-5,22E-dien-3β-ol, (2) 27-nor-24-methylcholesta-5,22E-dien-3β-ol, (3) cholesterol-5,22E-dien-3β-ol, (4) cholesterol-5-en-3β-ol, (5) 24-methylcholesta-5,22E-dien-3β-ol, (6) cholesterol-5,24-dien-3β-ol, (7) 24-methylcholesta-5,24(28)-dien-3β-ol, (8) 24-ethylcholesta-5,24(28)dien-3β-ol</figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="Peruvian_Shelf">Peruvian Shelf</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Desmosterol&action=edit&section=7" title="Edit section: Peruvian Shelf"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Diatoms and Silicoflagellates are classes of phytoplankton present in sedimentary material from the sediment water interface in the Peruvian Shelf region.<sup id="cite_ref-:0_5-2" class="reference"><a href="#cite_note-:0-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> Mineralogical analysis of this sedimentary material suggested large volumes of phytoplankton. Researchers at the University of Bristol examined the sterol composition of these sedimentary rocks which have gone through oxygen depletion, leading to anoxic conditions. These conditions have enhanced the preservation of lipids present during the time of formation, around 1 year prior, and have limited the degradation of these compounds. </p> <div class="mw-heading mw-heading2"><h2 id="Measurement_techniques">Measurement techniques</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Desmosterol&action=edit&section=8" title="Edit section: Measurement techniques"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Desmosterol has seen to be identified most commonly through chemical constants, <a href="/wiki/Ozonolysis" title="Ozonolysis">ozonolysis</a>, <a href="/wiki/Infrared_spectroscopy" title="Infrared spectroscopy">infrared spectroscopy</a>, <a href="/wiki/Nuclear_magnetic_resonance" title="Nuclear magnetic resonance">NMR</a>, and <a href="/wiki/Mass_spectrometry" title="Mass spectrometry">mass spectrometry</a> techniques.<sup id="cite_ref-:4_10-4" class="reference"><a href="#cite_note-:4-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> The use of thin-layer and gas-liquid chromatography to measure desmosterol is less common with the development of more advanced techniques. </p> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Desmosterol_Mass_Spec_new_2.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b4/Desmosterol_Mass_Spec_new_2.jpg/600px-Desmosterol_Mass_Spec_new_2.jpg" decoding="async" width="600" height="208" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b4/Desmosterol_Mass_Spec_new_2.jpg/900px-Desmosterol_Mass_Spec_new_2.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b4/Desmosterol_Mass_Spec_new_2.jpg/1200px-Desmosterol_Mass_Spec_new_2.jpg 2x" data-file-width="2880" data-file-height="1000" /></a><figcaption>Mass Spectra of Desmosterol, with data from NIST Standard Reference Database 69: <i>NIST Chemistry WebBook</i> <sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup></figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="GC-MS">GC-MS</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Desmosterol&action=edit&section=9" title="Edit section: GC-MS"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Samples from water sources are first extracted and partially purified before analysis. Sterols are commonly first derivatised after purification. Lipid extracts can be separated into their fragments by ionisation using Gas Chromatography followed by Mass Spectroscopy analysis. Desmosterol has a characteristic m/z peak at 384, as seen in the mass spectra.<sup id="cite_ref-:12_6-1" class="reference"><a href="#cite_note-:12-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Ozonolysis">Ozonolysis</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Desmosterol&action=edit&section=10" title="Edit section: Ozonolysis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Desmosterol has been identified through ozonolysis of the sample, with the ozonolysis product of desmosterol having a melting point of 128 °C, and an Rf value of 0.31 with paper-chromatography with n-hexane and N,N-dimethyl formamide. The ozonolysis product also has ratios C: 45.68; H: 4.45; N: 23.21.<sup id="cite_ref-:4_10-5" class="reference"><a href="#cite_note-:4-10"><span class="cite-bracket">[</span>10<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=Desmosterol&action=edit&section=11" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Cholesterol" title="Cholesterol">Cholesterol</a></li> <li><a href="/wiki/Triparanol" title="Triparanol">Triparanol</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=Desmosterol&action=edit&section=12" 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"><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="CITEREFKamalPal2023" class="citation journal cs1">Kamal, Md. 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February 1979. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1017%2Fs0033291700021735">10.1017/s0033291700021735</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Psychological+Medicine&rft.atitle=Handbook+of+Psychopharmacology.+Edited+by+L.+L.+Iversen%2C+S.+D.+Iversen+and+S.+H.+Snyder.+Plenum+Press%3A+New+York.+1978.+-+Volume+7Principles+of+Behavioral+Pharmacology.+%28Pp.+453%3B+illustrated%3B+%2434.50.%29+Plenum+Press%3A+New+York.+1978.+-+Volume+8Drugs%2C+Neurotransmitters%2C+and+Behavior.+%28Pp.+590%3B+illustrated%3B+%2439.50.%29+Plenum+Press%3A+New+York.+1978.+-+Volume+9Chemical+Pathways+in+the+Brain.+%28Pp.+410%3B+illustrated%3B+%2429.50.%29+Plenum+Press%3A+New+York.+1978.+-+Volume+10Neuroleptics+and+Schizophrenia.+%28Pp.+250%3B+illustrated%3B+%2425.00.%29+Plenum+Press%3A+New+York.+1978.+-+Volume+11Stimulants.+%28Pp.+476%3B+illustrated%3B+%2432.50.%29+Plenum+Press%3A+New+York.+1978.+-+Volume+12Drugs+of+Abuse.+%28Pp.+420%3B+illustrated%3B+%2432.50.%29+Plenum+Press%3A+New+York.+1978.+-+Volume+13Biology+of+Mood+and+Anti-anxiety+Drugs.+%28Pp.+440%3B+illustrated%3B+%2432.50.%29+Plenum+Press%3A+New+York.+1978.+-+Volume+14Affective+Disorders%3A+Drug+Actions+in+Animals+and+Man.+%28Pp.+379%3B+illustrated%3B+%2429.50.%29+Plenum+Press%3A+New+York.+1978.&rft.volume=9&rft.issue=1&rft.pages=194-195&rft.date=1979-02&rft_id=info%3Adoi%2F10.1017%2Fs0033291700021735&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADesmosterol" class="Z3988"></span></span> </li> <li id="cite_note-19"><span class="mw-cite-backlink"><b><a href="#cite_ref-19">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHammReigstadRiserMühlebach2001" class="citation journal cs1">Hamm, Christian; Reigstad, Marit; Riser, Christian Wexels; Mühlebach, Anneke; Wassmann, Paul (2001). <a rel="nofollow" class="external text" href="https://doi.org/10.3354%2Fmeps209055">"On the trophic fate of Phaeocystis pouchetii.: VII. Sterols and fatty acids reveal sedimentation of P. pouchetii-derived organic matter via krill fecal strings"</a>. <i>Marine Ecology Progress Series</i>. <b>209</b>: 55–69. <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/10.3354%2Fmeps209055">10.3354/meps209055</a></span>. <a href="/wiki/JSTOR_(identifier)" class="mw-redirect" title="JSTOR (identifier)">JSTOR</a> <a rel="nofollow" class="external text" href="https://www.jstor.org/stable/24863836">24863836</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Marine+Ecology+Progress+Series&rft.atitle=On+the+trophic+fate+of+Phaeocystis+pouchetii.%3A+VII.+Sterols+and+fatty+acids+reveal+sedimentation+of+P.+pouchetii-derived+organic+matter+via+krill+fecal+strings&rft.volume=209&rft.pages=55-69&rft.date=2001&rft_id=info%3Adoi%2F10.3354%2Fmeps209055&rft_id=https%3A%2F%2Fwww.jstor.org%2Fstable%2F24863836%23id-name%3DJSTOR&rft.aulast=Hamm&rft.aufirst=Christian&rft.au=Reigstad%2C+Marit&rft.au=Riser%2C+Christian+Wexels&rft.au=M%C3%BChlebach%2C+Anneke&rft.au=Wassmann%2C+Paul&rft_id=https%3A%2F%2Fdoi.org%2F10.3354%252Fmeps209055&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADesmosterol" class="Z3988"></span></span> </li> <li id="cite_note-20"><span class="mw-cite-backlink"><b><a href="#cite_ref-20">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://webbook.nist.gov/cgi/cbook.cgi?ID=C313042&Units=SI&Mask=200#Mass-Spec">"Desmosterol"</a>. <i>webbook.nist.gov</i>. 17 October 2019<span class="reference-accessdate">. Retrieved <span class="nowrap">2023-06-10</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=webbook.nist.gov&rft.atitle=Desmosterol&rft.date=2019-10-17&rft_id=https%3A%2F%2Fwebbook.nist.gov%2Fcgi%2Fcbook.cgi%3FID%3DC313042%26Units%3DSI%26Mask%3D200%23Mass-Spec&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADesmosterol" class="Z3988"></span></span> </li> </ol></div> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output .hlist.inline,.mw-parser-output .hlist.inline dl,.mw-parser-output .hlist.inline ol,.mw-parser-output .hlist.inline ul,.mw-parser-output .hlist dl dl,.mw-parser-output .hlist dl ol,.mw-parser-output .hlist dl ul,.mw-parser-output .hlist ol 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.navbox{display:none!important}}</style></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"><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 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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 class="mw-selflink selflink">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 href="/wiki/Ergosterol" title="Ergosterol">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><noscript><img 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