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class="firstHeading mw-first-heading"><span class="mw-page-title-main">7-Dehydrocholesterol</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 19 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-19" 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">19 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/7-%D8%AF%D9%8A%D9%87%D9%8A%D8%AF%D8%B1%D9%88%D9%83%D9%88%D9%84%D9%8A%D8%B3%D8%AA%D9%8A%D8%B1%D9%88%D9%84" title="7-ديهيدروكوليستيرول – Arabic" lang="ar" hreflang="ar" data-title="7-ديهيدروكوليستيرول" 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/%DB%B7-%D8%AF%D9%87%DB%8C%D8%AF%D8%B1%D9%88%DA%A9%D9%84%D8%B3%D8%AA%D8%B1%D9%88%D9%84" title="۷-دهیدروکلسترول – South Azerbaijani" lang="azb" hreflang="azb" data-title="۷-دهیدروکلسترول" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/7-dehydrocholesterol" title="7-dehydrocholesterol – Czech" lang="cs" hreflang="cs" data-title="7-dehydrocholesterol" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/7-Dehydrocholesterin" title="7-Dehydrocholesterin – German" lang="de" hreflang="de" data-title="7-Dehydrocholesterin" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/7-deh%C3%BCdrokolesterool" title="7-dehüdrokolesterool – Estonian" lang="et" hreflang="et" data-title="7-dehüdrokolesterool" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%DB%B7-%D8%AF%D9%87%DB%8C%D8%AF%D8%B1%D9%88%DA%A9%D9%84%D8%B3%D8%AA%D8%B1%D9%88%D9%84" title="۷-دهیدروکلسترول – Persian" lang="fa" hreflang="fa" data-title="۷-دهیدروکلسترول" 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/7-D%C3%A9shydrocholest%C3%A9rol" title="7-Déshydrocholestérol – French" lang="fr" hreflang="fr" data-title="7-Déshydrocholestérol" 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/7-Deshidrocolesterol" title="7-Deshidrocolesterol – Galician" lang="gl" hreflang="gl" data-title="7-Deshidrocolesterol" 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/7-%EB%94%94%ED%95%98%EC%9D%B4%EB%93%9C%EB%A1%9C%EC%BD%9C%EB%A0%88%EC%8A%A4%ED%85%8C%EB%A1%A4" title="7-디하이드로콜레스테롤 – Korean" lang="ko" hreflang="ko" data-title="7-디하이드로콜레스테롤" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/7-deidrocolesterolo" title="7-deidrocolesterolo – Italian" lang="it" hreflang="it" data-title="7-deidrocolesterolo" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/7-dehydrocholesterol" title="7-dehydrocholesterol – Dutch" lang="nl" hreflang="nl" data-title="7-dehydrocholesterol" 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/7-%E3%83%87%E3%83%92%E3%83%89%E3%83%AD%E3%82%B3%E3%83%AC%E3%82%B9%E3%83%86%E3%83%AD%E3%83%BC%E3%83%AB" title="7-デヒドロコレステロール – Japanese" lang="ja" hreflang="ja" data-title="7-デヒドロコレステロール" 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-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/7-Dehydrocholesterol" title="7-Dehydrocholesterol – Polish" lang="pl" hreflang="pl" data-title="7-Dehydrocholesterol" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/7-dehidrocolesterol" title="7-dehidrocolesterol – Romanian" lang="ro" hreflang="ro" data-title="7-dehidrocolesterol" 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/7-%D0%94%D0%B8%D0%B3%D0%B8%D0%B4%D1%80%D0%BE%D1%85%D0%BE%D0%BB%D0%B5%D1%81%D1%82%D0%B5%D1%80%D0%B8%D0%BD" title="7-Дигидрохолестерин – Russian" lang="ru" hreflang="ru" data-title="7-Дигидрохолестерин" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/7-Dehidroholesterol" title="7-Dehidroholesterol – Serbian" lang="sr" hreflang="sr" data-title="7-Dehidroholesterol" 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/7-Dehidroholesterol" title="7-Dehidroholesterol – Serbo-Croatian" lang="sh" hreflang="sh" data-title="7-Dehidroholesterol" 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-ur mw-list-item"><a href="https://ur.wikipedia.org/wiki/7-Dehydrocholesterol" title="7-Dehydrocholesterol – Urdu" lang="ur" hreflang="ur" data-title="7-Dehydrocholesterol" data-language-autonym="اردو" data-language-local-name="Urdu" class="interlanguage-link-target"><span>اردو</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/7-%E8%84%B1%E6%B0%A2%E8%83%86%E5%9B%BA%E9%86%87" title="7-脱氢胆固醇 – Chinese" lang="zh" hreflang="zh" data-title="7-脱氢胆固醇" 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 after-portlet-lang"><span class="wb-langlinks-edit wb-langlinks-link"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q139350#sitelinks-wikipedia" title="Edit 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data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">"Provitamin D3" redirects here. For the inactive form of vitamin D<sub>3</sub> synthesized from 7-dehydrocholesterol, see <a href="/wiki/Cholecalciferol" title="Cholecalciferol">Cholecalciferol</a>.</div> <style data-mw-deduplicate="TemplateStyles:r1268415487">.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%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}</style> <table class="infobox ib-chembox"> <caption>7-Dehydrocholesterol </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><figure class="mw-halign-center skin-invert-image" typeof="mw:File"><a href="/wiki/File:7-Dehydrocholesterol.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/bb/7-Dehydrocholesterol.svg/220px-7-Dehydrocholesterol.svg.png" decoding="async" width="220" height="174" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/bb/7-Dehydrocholesterol.svg/330px-7-Dehydrocholesterol.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/bb/7-Dehydrocholesterol.svg/440px-7-Dehydrocholesterol.svg.png 2x" data-file-width="1540" data-file-height="1215" /></a><figcaption></figcaption></figure> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:7-Dehydrocholesterol_molecule_ball.png" class="mw-file-description"><img alt="Ball-and-stick model of 7-dehydrocholesterol" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/2b/7-Dehydrocholesterol_molecule_ball.png/250px-7-Dehydrocholesterol_molecule_ball.png" decoding="async" width="250" height="121" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/2b/7-Dehydrocholesterol_molecule_ball.png/375px-7-Dehydrocholesterol_molecule_ball.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/2b/7-Dehydrocholesterol_molecule_ball.png/500px-7-Dehydrocholesterol_molecule_ball.png 2x" data-file-width="2064" data-file-height="1000" /></a><figcaption></figcaption></figure> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; 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-5,7-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>R</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-methylheptan-2-yl]-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;color:inherit; 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=434-16-2">434-16-2</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%3DC1%5C%5BC%40H%5D%28CC%5BC%40%5D2%28%5BC%40H%5D1CC%5BC%40%40H%5D2%5BC%40H%5D%28C%29CCCC%28C%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=17759">CHEBI:17759</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.388534.html">388534</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/100.006.456">100.006.456</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q139350#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/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=7-dehydrocholesterol">7-dehydrocholesterol</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/172">172</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/BK1IU07GKF">BK1IU07GKF</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/DTXSID20861933">DTXSID20861933</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q139350#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;"><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/h9-10,18-19,21,23-25,28H,6-8,11-17H2,1-5H3/t19-,21+,23-,24+,25+,26+,27-/m1/s1-dehydrocholesterol<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></div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: UCTLRSWJYQTBFZ-DDPQNLDTSA-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/h9-10,18-19,21,23-25,28H,6-8,11-17H2,1-5H3/t19-,21+,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: UCTLRSWJYQTBFZ-DDPQNLDTBZ</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;"><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)CCCC(C)C)C)[C@@]3(C)CC4</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; 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>384.638    </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; color:inherit; 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=477226494&page2=7-Dehydrocholesterol">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> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Skinlayers.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/20/Skinlayers.png/250px-Skinlayers.png" decoding="async" width="250" height="248" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/2/20/Skinlayers.png 1.5x" data-file-width="332" data-file-height="329" /></a><figcaption>The epidermal strata of the skin</figcaption></figure> <p><b>7-Dehydrocholesterol</b> (<b>7-DHC</b>) is a <a href="/wiki/Zoosterol" class="mw-redirect" title="Zoosterol">zoosterol</a> that functions in the <a href="/wiki/Blood_plasma" title="Blood plasma">serum</a> as a <a href="/wiki/Cholesterol" title="Cholesterol">cholesterol</a> precursor, and is <a href="/wiki/Photochemically" class="mw-redirect" title="Photochemically">photochemically</a> converted to <a href="/wiki/Cholecalciferol" title="Cholecalciferol">vitamin D<sub>3</sub></a> in the <a href="/wiki/Skin" title="Skin">skin</a>, therefore functioning as <a href="/wiki/Provitamin" title="Provitamin">provitamin</a>-D<sub>3</sub>. The presence of this compound in human skin enables humans to manufacture vitamin D<sub>3</sub> (<a href="/wiki/Cholecalciferol" title="Cholecalciferol">cholecalciferol</a>). Upon exposure to <a href="/wiki/Ultraviolet" title="Ultraviolet">ultraviolet</a> UV-B rays in the sun light, 7-DHC is converted into vitamin D<sub>3</sub> via <a href="/wiki/Previtamin_D3" title="Previtamin D3">previtamin D<sub>3</sub></a> as an intermediate <a href="/wiki/Isomer" title="Isomer">isomer</a>. It is also found in the <a href="/wiki/Milk" title="Milk">milk</a> of several mammalian species.<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><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> <a href="/wiki/Lanolin" title="Lanolin">Lanolin</a>, a waxy substance that is naturally secreted by wool-bearing mammals, contains 7-DHC which is converted into vitamin D by sunlight and then ingested during grooming as a nutrient. In insects 7-dehydrocholesterol is a precursor for the hormone <a href="/wiki/Ecdysone" title="Ecdysone">ecdysone</a>, required for reaching adulthood.<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> 7-DHC was discovered by Nobel-laureate organic chemist <a href="/wiki/Adolf_Windaus" title="Adolf Windaus">Adolf Windaus</a>. </p> <meta property="mw:PageProp/toc" /> <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=7-Dehydrocholesterol&action=edit&section=1" title="Edit section: Biosynthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>It is synthesized from <a href="/wiki/Lathosterol" title="Lathosterol">lathosterol</a> by the enzyme <a href="/wiki/Lathosterol_oxidase" class="mw-redirect" title="Lathosterol oxidase">lathosterol oxidase</a> (lathosterol 5-desaturase). This is the next-to-last step of cholesterol biosynthesis.<sup id="cite_ref-pmid12812989_4-0" class="reference"><a href="#cite_note-pmid12812989-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> Defective synthesis results in the human inherited disorder <a href="/wiki/Lathosterolosis" title="Lathosterolosis">lathosterolosis</a> resembling <a href="/wiki/Smith%E2%80%93Lemli%E2%80%93Opitz_syndrome" title="Smith–Lemli–Opitz syndrome">Smith–Lemli–Opitz syndrome</a>.<sup id="cite_ref-pmid12812989_4-1" class="reference"><a href="#cite_note-pmid12812989-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> Mice where this gene has been deleted lose the ability to increase vitamin D<sub>3</sub> in the blood following UV exposure of the skin.<sup id="cite_ref-pmid28330720_5-0" class="reference"><a href="#cite_note-pmid28330720-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Location">Location</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=7-Dehydrocholesterol&action=edit&section=2" title="Edit section: Location"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The skin consists of two primary layers: an inner layer, the <a href="/wiki/Dermis" title="Dermis">dermis</a>, comprising largely <a href="/wiki/Connective_tissue" title="Connective tissue">connective tissue</a>, and an outer, thinner <a href="/wiki/Epidermis_(skin)" class="mw-redirect" title="Epidermis (skin)">epidermis</a>. The thickness of the epidermis ranges from 0.04 mm to greater than 0.6 mm.<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> The epidermis comprises five <i>strata</i>; from outer to inner, they are the <a href="/wiki/Stratum_corneum" title="Stratum corneum">stratum corneum</a>, <a href="/wiki/Stratum_lucidum" title="Stratum lucidum">stratum lucidum</a>, <a href="/wiki/Stratum_granulosum" title="Stratum granulosum">stratum granulosum</a>, <a href="/wiki/Stratum_spinosum" title="Stratum spinosum">stratum spinosum</a>, and <a href="/wiki/Stratum_basale" title="Stratum basale">stratum basale</a>. The highest concentrations of 7-dehydrocholesterol are found in the epidermal layer of skin—specifically in the stratum basale and stratum spinosum.<sup id="cite_ref-Norman_1998_7-0" class="reference"><a href="#cite_note-Norman_1998-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> The production of pre-vitamin D<sub>3</sub> is, therefore, greatest in these two layers. </p> <div class="mw-heading mw-heading2"><h2 id="Radiation">Radiation</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=7-Dehydrocholesterol&action=edit&section=3" title="Edit section: Radiation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Synthesis of pre-vitamin D<sub>3</sub> in the skin involves <a href="/wiki/UVB_radiation" class="mw-redirect" title="UVB radiation">UVB radiation</a>, which effectively penetrates only the epidermal layers of skin. 7-Dehydrocholesterol absorbs UV light most effectively at <a href="/wiki/Wavelength" title="Wavelength">wavelengths</a> between 295 and 300 <a href="/wiki/Nanometer" class="mw-redirect" title="Nanometer">nm</a> and, thus, the production of vitamin D<sub>3</sub> will occur primarily at those wavelengths.<sup id="cite_ref-pmid6281884_8-0" class="reference"><a href="#cite_note-pmid6281884-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> The two most important factors that govern the generation of pre-vitamin D<sub>3</sub> are the quantity (intensity) and quality (appropriate wavelength) of the UVB irradiation reaching the 7-dehydrocholesterol deep in the stratum basale and stratum spinosum.<sup id="cite_ref-Norman_1998_7-1" class="reference"><a href="#cite_note-Norman_1998-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> Light-emitting diodes (<a href="/wiki/LED" class="mw-redirect" title="LED">LEDs</a>) can be used to produce the radiation.<sup id="cite_ref-pmid28904394_9-0" class="reference"><a href="#cite_note-pmid28904394-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p><p>Another important consideration is the quantity of 7-dehydrocholesterol present in the skin. Under normal circumstances, ample quantities of 7-dehydrocholesterol (about 25–50 <a href="/wiki/Microgram" title="Microgram">μg</a>/cm<sup>2</sup> of skin) are available in the <a href="/wiki/Stratum_spinosum" title="Stratum spinosum">stratum spinosum</a> and <a href="/wiki/Stratum_basale" title="Stratum basale">stratum basale</a> of human skin to meet the body's vitamin D requirements. 7-DHC insufficiency has been proposed as an alternate cause for Vitamin D deficiency.<sup id="cite_ref-whackjob_10-0" class="reference"><a href="#cite_note-whackjob-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Sources">Sources</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=7-Dehydrocholesterol&action=edit&section=4" title="Edit section: Sources"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>7-DHC can be produced by animals and plants via different pathways. It is not produced by fungi in significant amounts. It is made by some <a href="/wiki/Algae" title="Algae">algae</a>, but the pathway is poorly understood.<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><p>Industrially, 7-DHC generally comes from <a href="/wiki/Lanolin" title="Lanolin">lanolin</a>, and is used to produce vitamin D3 by UV exposure.<sup id="cite_ref-Holick05_12-0" class="reference"><a href="#cite_note-Holick05-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Lichen" title="Lichen">Lichen</a> (<a href="/wiki/Cladonia_rangiferina" title="Cladonia rangiferina">Cladonia rangiferina</a>) is used to produce <a href="/wiki/Vegan" class="mw-redirect" title="Vegan">vegan</a> D3.<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><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><p>7-DHC is used for vitamin D3 synthesis via <a href="/wiki/Lanosterol" title="Lanosterol">lanosterol</a> in land animals, via <a href="/wiki/Cycloartenol" title="Cycloartenol">cycloartenol</a> in plants, and in algae together with another provitamin D <a href="/wiki/Ergosterol" title="Ergosterol">ergosterol</a> for D2. In fungi solely ergosterol is used for synthesis of D2 via lanosterol.<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> </p> <div class="mw-heading mw-heading2"><h2 id="Interactive_pathway_map">Interactive pathway map</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=7-Dehydrocholesterol&action=edit&section=5" title="Edit section: Interactive pathway map"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div style="overflow:auto;text-align: right"> <p><i>Click on genes, proteins and metabolites below to link to respective articles.</i> <sup id="cite_ref-WikiPathways_16-0" class="reference"><a href="#cite_note-WikiPathways-16"><span class="cite-bracket">[</span>§ 1<span class="cite-bracket">]</span></a></sup> </p> <div class="thumb tright"> <div class="thumbinner" style="width: 377px;"> <div class="thumbimage" style="width: 375px; height: 350px; overflow: hidden;"> <div style="position: relative; top: -25px; left: -98.2949283351709px; width: {{{bSize}}}px"><div class="noresize">[[File:<div class="noresize thumb tnone" style=";"> <div class="thumbinner" style="overflow:hidden;width:1118px;"> <div class="thumbimage" style="overflow:hidden; position:relative; background-color:white;"> <div style=";left:0px; top:0px; width:1116px; position:absolute;"> <figure class="mw-default-size mw-halign-right noresize" typeof="mw:File"><a href="/wiki/Vitamin_D#Interactive_pathway_map" title="Go to pathway article"><img alt="VitaminDSynthesis_WP1531" src="//upload.wikimedia.org/wikipedia/commons/2/27/VitaminDSynthesis_WP1531.png" decoding="async" width="1116" height="1069" class="mw-file-element" data-file-width="1116" data-file-height="1069" usemap="#ImageMap_80523bcf44d6d157" /></a><map name="ImageMap_80523bcf44d6d157"><area href="/wiki/7-Dehydrocholesterol" shape="rect" 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title="go to article" /><area href="/wiki/Parathyroid_hormone" shape="rect" coords="704,582,822,607" alt="go to article" title="go to article" /><area href="/wiki/CYP24A1" shape="rect" coords="857,474,933,499" alt="go to article" title="go to article" /><area href="/wiki/Vitamin_D-binding_protein" shape="rect" coords="656,814,797,843" alt="go to article" title="go to article" /><area href="/wiki/Calcium_in_biology" shape="rect" coords="762,709,789,729" alt="Go to article" title="Go to article" /><area href="/wiki/Phosphate" shape="rect" coords="789,709,816,729" alt="Go to article" title="Go to article" /><area href="/wiki/Calcitriol_receptor" shape="rect" coords="594,894,654,923" alt="go to article" title="go to article" /><area href="/wiki/Vitamin_D-binding_protein" shape="rect" coords="370,330,514,357" alt="Go to article" title="Go to article" /><area href="/wiki/CYP27A1" shape="rect" coords="246,400,305,422" alt="go to article" title="go to article" /><area href="/wiki/Retinoid_X_receptor_alpha" shape="rect" coords="676,911,732,934" alt="go to article" title="go to article" /><area href="/wiki/Retinoid_X_receptor_beta" shape="rect" coords="676,934,732,957" alt="go to article" title="go to article" /><area href="/wiki/Cholesterol" shape="rect" coords="235,29,315,49" alt="Go to article" title="Go to article" /><area href="/wiki/7-Dehydrocholesterol_reductase" shape="rect" coords="245,72,307,92" alt="go to article" title="go to article" /></map><figcaption></figcaption></figure></div> <div style="text-align:left; background-color:transparent; color:white; line-height:110%;"> <div id="annotation_0x0" style="position:absolute; left:0px; top:0px; line-height:110%;"><span style="background-color:transparent; color:inherit;">[[<div style="display:block; width:76px; height:0px; overflow:hidden; position:relative; left:237.79492833517088px; top:121.919335370502px; background:transparent; border-top:3px blue solid"></div>]]</span></div> <div 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style="position:absolute; left:0px; top:0px; line-height:110%;"><span style="background-color:transparent; color:inherit;">[[<div style="display:block; width:61.882028665932px; height:0px; overflow:hidden; position:relative; left:245.117971334068px; top:76.6613419857165px; background:transparent; border-top:3px blue solid"></div>]]</span></div> <div id="annotation_0x0" style="position:absolute; left:0px; top:0px; line-height:110%;"><span style="background-color:transparent; color:inherit;">[[<div style="display:block; width:69px; height:20px; overflow:hidden; position:relative; left:237.79492833517088px; top:96.9193353705016px; background:transparent; border:4px black solid"></div>]]</span></div> </div> <div style="visibility:hidden"><figure class="mw-default-size mw-halign-right noresize" typeof="mw:File"><a href="/wiki/Vitamin_D#Interactive_pathway_map" title="Go to pathway article"><img alt="VitaminDSynthesis_WP1531" src="//upload.wikimedia.org/wikipedia/commons/2/27/VitaminDSynthesis_WP1531.png" decoding="async" width="1116" height="1069" class="mw-file-element" data-file-width="1116" data-file-height="1069" usemap="#ImageMap_80523bcf44d6d157" /></a><map name="ImageMap_80523bcf44d6d157"><area href="/wiki/7-Dehydrocholesterol" shape="rect" coords="238,109,314,137" alt="Go to article" title="Go to article" /><area href="/wiki/Previtamin_D3" shape="rect" coords="233,227,318,252" alt="Go to article" title="Go to article" /><area href="/wiki/Cholecalciferol" shape="rect" coords="228,307,321,332" alt="Go to article" title="Go to article" /><area href="/wiki/Calcifediol" shape="rect" coords="243,471,306,501" alt="Go to article" title="Go to article" /><area href="/wiki/CYP2R1" shape="rect" coords="246,377,305,400" alt="go to article" title="go to article" /><area href="/wiki/Calcifediol" shape="rect" coords="593,471,655,501" alt="Go to article" title="Go to article" /><area href="/wiki/24,25-Dihydroxycholecalciferol" shape="rect" coords="1001,465,1087,505" alt="Go to article" title="Go to article" /><area href="/wiki/Calcitriol" shape="rect" coords="586,751,662,778" alt="Go to article" title="Go to article" /><area href="/wiki/25-Hydroxyvitamin_D3_1-alpha-hydroxylase" shape="rect" coords="581,680,664,707" alt="go to article" title="go to article" /><area href="/wiki/Parathyroid_hormone" shape="rect" coords="704,582,822,607" alt="go to article" title="go to article" /><area href="/wiki/CYP24A1" shape="rect" coords="857,474,933,499" alt="go to article" title="go to article" /><area href="/wiki/Vitamin_D-binding_protein" shape="rect" coords="656,814,797,843" alt="go to article" title="go to article" /><area href="/wiki/Calcium_in_biology" shape="rect" coords="762,709,789,729" alt="Go to article" title="Go to article" /><area href="/wiki/Phosphate" shape="rect" coords="789,709,816,729" alt="Go to article" title="Go to article" /><area href="/wiki/Calcitriol_receptor" shape="rect" coords="594,894,654,923" alt="go to article" title="go to article" /><area href="/wiki/Vitamin_D-binding_protein" shape="rect" coords="370,330,514,357" alt="Go to article" title="Go to article" /><area href="/wiki/CYP27A1" shape="rect" coords="246,400,305,422" alt="go to article" title="go to article" /><area href="/wiki/Retinoid_X_receptor_alpha" shape="rect" coords="676,911,732,934" alt="go to article" title="go to article" /><area href="/wiki/Retinoid_X_receptor_beta" shape="rect" coords="676,934,732,957" alt="go to article" title="go to article" /><area href="/wiki/Cholesterol" shape="rect" coords="235,29,315,49" alt="Go to article" title="Go to article" /><area href="/wiki/7-Dehydrocholesterol_reductase" shape="rect" coords="245,72,307,92" alt="go to article" title="go to article" /></map><figcaption></figcaption></figure></div> </div> <div class="thumbcaption"></div> </div></div>|alt=Vitamin D Synthesis Pathway (<a rel="nofollow" class="external text" href="http://www.wikipathways.org/index.php/Pathway:WP1531">view</a> / <a rel="nofollow" class="external text" href="http://www.wikipathways.org/index.php?title=Pathway:WP1531&action=edit">edit</a>)]]</div></div> </div> <div class="thumbcaption"> <div class="magnify"><a href="/wiki/File:VitaminDSynthesis_WP1531.png" title="File:VitaminDSynthesis WP1531.png"> </a></div>Vitamin D Synthesis Pathway (<a rel="nofollow" class="external text" href="http://www.wikipathways.org/index.php/Pathway:WP1531">view</a> / <a rel="nofollow" class="external text" href="http://www.wikipathways.org/index.php?title=Pathway:WP1531&action=edit">edit</a>) </div> </div> </div> <div style="clear:both;" class=""></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 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<style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://www.wikipathways.org/index.php/Pathway:WP1531">"VitaminDSynthesis_WP1531"</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=VitaminDSynthesis_WP1531&rft_id=http%3A%2F%2Fwww.wikipathways.org%2Findex.php%2FPathway%3AWP1531&rfr_id=info%3Asid%2Fen.wikipedia.org%3A7-Dehydrocholesterol" class="Z3988"></span></span> </li> </ol></div></div> </div> <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=7-Dehydrocholesterol&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/Vitamin_D" title="Vitamin D">Vitamin D</a></li> <li><a href="/wiki/Smith%E2%80%93Lemli%E2%80%93Opitz_syndrome" title="Smith–Lemli–Opitz syndrome">Smith–Lemli–Opitz syndrome</a></li> <li><a href="/wiki/7-Dehydrocholesterol_reductase" title="7-Dehydrocholesterol reductase">7-Dehydrocholesterol reductase</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=7-Dehydrocholesterol&action=edit&section=7" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239543626" /><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 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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)79" 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 href="/wiki/Ergosterol" title="Ergosterol">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 class="mw-selflink selflink">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/Nicotinic_acid" title="Nicotinic acid">Nicotinic acid</a></li> <li><a href="/wiki/Nicotinamide" title="Nicotinamide">Nicotinamide</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_intermediates189" 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_intermediates189" 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 class="mw-selflink selflink">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 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 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="Vitamin_D_receptor_modulators524" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><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:Vitamin_D_receptor_modulators" title="Template:Vitamin D receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Vitamin_D_receptor_modulators" title="Template talk:Vitamin D receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Vitamin_D_receptor_modulators" title="Special:EditPage/Template:Vitamin D receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Vitamin_D_receptor_modulators524" style="font-size:114%;margin:0 4em"><a href="/wiki/Vitamin_D_receptor" title="Vitamin D receptor">Vitamin D receptor</a> <a href="/wiki/Receptor_modulator" title="Receptor modulator">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Vitamin_D_receptor" title="Vitamin D receptor"><abbr title="Vitamin D receptor">VDR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Vitamin D receptor</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Agonists:</i> <a class="mw-selflink selflink">7-Dehydrocholesterol</a></li> <li><a href="/w/index.php?title=25-Hydroxyergocalciferol&action=edit&redlink=1" class="new" title="25-Hydroxyergocalciferol (page does not exist)">25-Hydroxyergocalciferol</a></li> <li><a href="/wiki/Alfacalcidol" title="Alfacalcidol">Alfacalcidol</a></li> <li><a href="/wiki/Calcifediol" title="Calcifediol">Calcifediol</a></li> <li><a href="/wiki/Calciferol" class="mw-redirect" title="Calciferol">Calciferol</a></li> <li><a href="/wiki/Calcipotriol" title="Calcipotriol">Calcipotriol</a></li> <li><a href="/wiki/Calcitriol" title="Calcitriol">Calcitriol</a></li> <li><a href="/wiki/Cholecalciferol" title="Cholecalciferol">Cholecalciferol</a> (<a href="/wiki/Vitamin_D3" class="mw-redirect" title="Vitamin D3">vitamin D<sub>3</sub></a>)</li> <li><a href="/wiki/Dihydrotachysterol" title="Dihydrotachysterol">Dihydrotachysterol</a></li> <li><a href="/wiki/Doxercalciferol" title="Doxercalciferol">Doxercalciferol</a></li> <li><a href="/w/index.php?title=EB-1089&action=edit&redlink=1" class="new" title="EB-1089 (page does not exist)">EB-1089</a></li> <li><a href="/wiki/Eldecalcitol" title="Eldecalcitol">Eldecalcitol</a></li> <li><a href="/w/index.php?title=Ercalcidiol&action=edit&redlink=1" class="new" title="Ercalcidiol (page does not exist)">Ercalcidiol</a></li> <li><a href="/w/index.php?title=Ercalcitriol&action=edit&redlink=1" class="new" title="Ercalcitriol (page does not exist)">Ercalcitriol</a></li> <li><a href="/wiki/Ergocalciferol" title="Ergocalciferol">Ergocalciferol</a> (<a href="/wiki/Vitamin_D2" class="mw-redirect" title="Vitamin D2">vitamin D<sub>2</sub></a>)</li> <li><a href="/wiki/Lithocholic_acid" title="Lithocholic acid">Lithocholic acid</a></li> <li><a href="/wiki/Maxacalcitol" title="Maxacalcitol">Maxacalcitol</a></li> <li><a href="/wiki/Paricalcitol" title="Paricalcitol">Paricalcitol</a></li> <li><a href="/wiki/Tacalcitol" title="Tacalcitol">Tacalcitol</a></li></ul> <ul><li><i>Antagonists:</i> <a href="/w/index.php?title=ZK159222&action=edit&redlink=1" class="new" title="ZK159222 (page does not exist)">ZK159222</a></li> <li><a href="/w/index.php?title=TEI-9647&action=edit&redlink=1" class="new" title="TEI-9647 (page does not exist)">TEI-9647</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt>See also</dt> <dd><i><a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></i></dd></dl> </div></td></tr></tbody></table></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?useformat=desktop&type=1x1&usesul3=0" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Retrieved from "<a dir="ltr" href="https://en.wikipedia.org/w/index.php?title=7-Dehydrocholesterol&oldid=1278548447">https://en.wikipedia.org/w/index.php?title=7-Dehydrocholesterol&oldid=1278548447</a>"</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div id="mw-normal-catlinks" class="mw-normal-catlinks"><a href="/wiki/Help:Category" title="Help:Category">Categories</a>: <ul><li><a href="/wiki/Category:Cholestanes" title="Category:Cholestanes">Cholestanes</a></li><li><a href="/wiki/Category:Sterols" title="Category:Sterols">Sterols</a></li><li><a href="/wiki/Category:Nutrition" title="Category:Nutrition">Nutrition</a></li><li><a href="/wiki/Category:Vitamin_D" title="Category:Vitamin D">Vitamin D</a></li></ul></div><div id="mw-hidden-catlinks" class="mw-hidden-catlinks mw-hidden-cats-hidden">Hidden categories: <ul><li><a href="/wiki/Category:Articles_without_KEGG_source" title="Category:Articles without KEGG source">Articles without KEGG source</a></li><li><a href="/wiki/Category:ECHA_InfoCard_ID_from_Wikidata" title="Category:ECHA InfoCard ID from Wikidata">ECHA InfoCard ID from Wikidata</a></li><li><a href="/wiki/Category:Articles_with_changed_InChI_identifier" title="Category:Articles with changed InChI identifier">Articles with changed InChI identifier</a></li><li><a href="/wiki/Category:Articles_containing_unverified_chemical_infoboxes" 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