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href="https://cs.wikipedia.org/wiki/Kyselina_beta-hydroxym%C3%A1seln%C3%A1" title="Kyselina beta-hydroxymáselná – Czech" lang="cs" hreflang="cs" data-title="Kyselina beta-hydroxymáselná" 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/3-Hydroxybutters%C3%A4ure" title="3-Hydroxybuttersäure – German" lang="de" hreflang="de" data-title="3-Hydroxybuttersäure" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/%C3%81cido_betahidroxibut%C3%ADrico" title="Ácido betahidroxibutírico – Spanish" lang="es" hreflang="es" data-title="Ácido betahidroxibutírico" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eo mw-list-item"><a href="https://eo.wikipedia.org/wiki/Beta-hidroksibutera_acido" title="Beta-hidroksibutera acido – Esperanto" lang="eo" hreflang="eo" data-title="Beta-hidroksibutera acido" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%A8%D8%AA%D8%A7-%D9%87%DB%8C%D8%AF%D8%B1%D9%88%DA%A9%D8%B3%DB%8C%E2%80%8C%D8%A8%D9%88%D8%AA%DB%8C%D8%B1%DB%8C%DA%A9_%D8%A7%D8%B3%DB%8C%D8%AF" title="بتا-هیدروکسی‌بوتیریک اسید – Persian" lang="fa" hreflang="fa" data-title="بتا-هیدروکسی‌بوتیریک اسید" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Acide_b%C3%AAta-hydroxybutyrique" title="Acide bêta-hydroxybutyrique – French" lang="fr" hreflang="fr" data-title="Acide bêta-hydroxybutyrique" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/%C3%81cido_beta-hidroxibut%C3%ADrico" title="Ácido beta-hidroxibutírico – Galician" lang="gl" hreflang="gl" data-title="Ácido beta-hidroxibutírico" 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/%EB%B2%A0%ED%83%80-%ED%95%98%EC%9D%B4%EB%93%9C%EB%A1%9D%EC%8B%9C%EB%B7%B0%ED%8B%B0%EB%A5%B4%EC%82%B0" title="베타-하이드록시뷰티르산 – Korean" lang="ko" hreflang="ko" data-title="베타-하이드록시뷰티르산" 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/Acido_%CE%B2-idrossibutirrico" title="Acido β-idrossibutirrico – Italian" lang="it" hreflang="it" data-title="Acido β-idrossibutirrico" 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/3-hydroxybutaanzuur" title="3-hydroxybutaanzuur – Dutch" lang="nl" hreflang="nl" data-title="3-hydroxybutaanzuur" 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/3-%E3%83%92%E3%83%89%E3%83%AD%E3%82%AD%E3%82%B7%E9%85%AA%E9%85%B8" title="3-ヒドロキシ酪酸 – Japanese" lang="ja" hreflang="ja" data-title="3-ヒドロキシ酪酸" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Kwas_3-hydroksymas%C5%82owy" title="Kwas 3-hydroksymasłowy – Polish" lang="pl" hreflang="pl" data-title="Kwas 3-hydroksymasłowy" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/%C3%81cido_beta-hidroxibut%C3%ADrico" title="Ácido beta-hidroxibutírico – Portuguese" lang="pt" hreflang="pt" data-title="Ácido beta-hidroxibutírico" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%91%D0%B5%D1%82%D0%B0-%D0%B3%D0%B8%D0%B4%D1%80%D0%BE%D0%BA%D1%81%D0%B8%D0%BC%D0%B0%D1%81%D0%BB%D1%8F%D0%BD%D0%B0%D1%8F_%D0%BA%D0%B8%D1%81%D0%BB%D0%BE%D1%82%D0%B0" title="Бета-гидроксимасляная кислота – Russian" lang="ru" hreflang="ru" data-title="Бета-гидроксимасляная кислота" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Kyselina_%CE%B2-hydroxybutyrov%C3%A1" title="Kyselina β-hydroxybutyrová – Slovak" lang="sk" hreflang="sk" data-title="Kyselina β-hydroxybutyrová" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Beta-Hidroksibutirinska_kiselina" title="Beta-Hidroksibutirinska kiselina – Serbian" lang="sr" hreflang="sr" data-title="Beta-Hidroksibutirinska kiselina" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Beta-Hidroksibutirinska_kiselina" title="Beta-Hidroksibutirinska kiselina – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Beta-Hidroksibutirinska kiselina" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/3-hydroksivoihappo" title="3-hydroksivoihappo – Finnish" lang="fi" hreflang="fi" data-title="3-hydroksivoihappo" data-language-autonym="Suomi" data-language-local-name="Finnish" 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acid</a>)</span></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><p class="mw-empty-elt"> </p> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">Not to be confused with <a href="/wiki/%CE%92-Hydroxy_%CE%B2-methylbutyric_acid" title="Β-Hydroxy β-methylbutyric acid">β-Hydroxy β-methylbutyric acid</a>.</div> <style data-mw-deduplicate="TemplateStyles:r1084375498">.mw-parser-output .ib-chembox{border-collapse:collapse;text-align:left}.mw-parser-output .ib-chembox td,.mw-parser-output .ib-chembox th{border:1px solid #a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}</style> <table class="infobox ib-chembox"> <caption>β-Hydroxybutyric acid </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Beta-Hydroxybutyric_acid-2D-skeletal.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0a/Beta-Hydroxybutyric_acid-2D-skeletal.svg/200px-Beta-Hydroxybutyric_acid-2D-skeletal.svg.png" decoding="async" width="200" height="105" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0a/Beta-Hydroxybutyric_acid-2D-skeletal.svg/300px-Beta-Hydroxybutyric_acid-2D-skeletal.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/0a/Beta-Hydroxybutyric_acid-2D-skeletal.svg/400px-Beta-Hydroxybutyric_acid-2D-skeletal.svg.png 2x" data-file-width="334" data-file-height="176" /></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/Preferred_IUPAC_name" title="Preferred IUPAC name">Preferred 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;">3-Hydroxybutanoic acid</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=300-85-6">300-85-6</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=O%3DC%28O%29CC%28O%29C">Interactive image</a></span></li><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=CC%28CC%28%3DO%29O%29O">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td>3DMet </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.3dmet.dna.affrc.go.jp"><a rel="nofollow" class="external text" href="http://www.3dmet.dna.affrc.go.jp/cgi/show_data.php?acc=B00239">B00239</a></span></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Beilstein_database" title="Beilstein database">Beilstein Reference</a></div> </td> <td>773861 </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=20067">CHEBI:20067</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/ChEMBL1162496">ChEMBL1162496</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.428.html">428</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/100.005.546">100.005.546</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q223092#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=1593">1593</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/KEGG" title="KEGG">KEGG</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.kegg.jp"><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/C01089">C01089</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/Medical_Subject_Headings" title="Medical Subject Headings">MeSH</a> </td> <td><span title="www.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://www.nlm.nih.gov/cgi/mesh/2014/MB_cgi?mode=&term=beta-Hydroxybutyrate">beta-Hydroxybutyrate</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/441">441</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/TZP1275679">TZP1275679</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/DTXSID60859511">DTXSID60859511</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q223092#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/C4H8O3/c1-3(5)2-4(6)7/h3,5H,2H2,1H3,(H,6,7)<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: WHBMMWSBFZVSSR-UHFFFAOYSA-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/C4H8O3/c1-3(5)2-4(6)7/h3,5H,2H2,1H3,(H,6,7)</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: WHBMMWSBFZVSSR-UHFFFAOYAO</div></div></li></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">O=C(O)CC(O)C</div></li><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%;">CC(CC(=O)O)O</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td><span title="Carbon">C</span><sub>4</sub><span title="Hydrogen">H</span><sub>8</sub><span title="Oxygen">O</span><sub>3</sub> </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td><span class="nowrap"><span data-sort-value="7002104105000000000♠"></span>104.105</span> g·mol<sup>−1</sup>   </td></tr> <tr> <td>Appearance </td> <td>white solid </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>44-46 </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Related compounds </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Other <a href="/wiki/Ion" title="Ion">anions</a></div> </td> <td><a href="/wiki/Hydroxybutyrate" class="mw-redirect" title="Hydroxybutyrate">hydroxybutyrate</a> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Related <a href="/wiki/Carboxylic_acid" title="Carboxylic acid">carboxylic acids</a></div> </td> <td><a href="/wiki/Propionic_acid" title="Propionic acid">propionic acid</a><br /><a href="/wiki/Lactic_acid" title="Lactic acid">lactic acid</a><br /><a href="/wiki/3-hydroxypropanoic_acid" class="mw-redirect" title="3-hydroxypropanoic acid">3-hydroxypropanoic acid</a><br /><a href="/wiki/Malonic_acid" title="Malonic acid">malonic acid</a><br /><a href="/wiki/%CE%92-hydroxyvaleric_acid" class="mw-redirect" title="Β-hydroxyvaleric acid">β-hydroxyvaleric acid</a><br /><a href="/wiki/Butyric_acid" title="Butyric acid">butyric acid</a><br /><a href="/wiki/%CE%92-methylbutyric_acid" class="mw-redirect" title="Β-methylbutyric acid">β-methylbutyric acid</a><br /><a href="/wiki/%CE%92-hydroxy_%CE%B2-methylbutyric_acid" class="mw-redirect" title="Β-hydroxy β-methylbutyric acid">β-hydroxy β-methylbutyric acid</a><br /><a href="/wiki/Crotonic_acid" title="Crotonic acid">crotonic acid</a> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Related compounds</div> </td> <td><a href="/wiki/Erythrose" title="Erythrose">erythrose</a><br /><a href="/wiki/Threose" title="Threose">threose</a><br /><a href="/wiki/1,2-butanediol" class="mw-redirect" title="1,2-butanediol">1,2-butanediol</a><br /><a href="/wiki/1,3-butanediol" class="mw-redirect" title="1,3-butanediol">1,3-butanediol</a><br /><a href="/wiki/2,3-butanediol" class="mw-redirect" title="2,3-butanediol">2,3-butanediol</a><br /><a href="/wiki/1,4-butanediol" class="mw-redirect" title="1,4-butanediol">1,4-butanediol</a> </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"><div style="text-align:center;"><span typeof="mw:File"><span><img alt="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=443420188&page2=%CE%92-Hydroxybutyric+acid">verify</a></span> (<a href="/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validation" title="Wikipedia:WikiProject Chemicals/Chembox validation">what is</a> <sup><span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup> ?) </div></div> <div style="margin-top: 0.3em; text-align: center;"><a href="/wiki/Wikipedia:Chemical_infobox#References" title="Wikipedia:Chemical infobox">Infobox references</a></div> </td></tr> </tbody></table><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound</div> <p><b>β-Hydroxybutyric acid</b>, also known as <b>3-hydroxybutyric acid</b> or <b>BHB</b>, is an organic compound and a <a href="/wiki/Beta_hydroxy_acid" class="mw-redirect" title="Beta hydroxy acid">beta hydroxy acid</a> with the <a href="/wiki/Chemical_formula" title="Chemical formula">chemical formula</a> CH<sub>3</sub>CH(OH)CH<sub>2</sub>CO<sub>2</sub>H; its <a href="/wiki/Conjugate_base" class="mw-redirect" title="Conjugate base">conjugate base</a> is <b>β-hydroxybutyrate</b>, also known as <b>3-hydroxybutyrate</b>. β-Hydroxybutyric acid is a <a href="/wiki/Chirality_(chemistry)" title="Chirality (chemistry)">chiral</a> compound with two <a href="/wiki/Enantiomers" class="mw-redirect" title="Enantiomers">enantiomers</a>: <small>D</small>-β-hydroxybutyric acid and <small>L</small>-β-hydroxybutyric acid. Its oxidized and polymeric derivatives occur widely in nature. In humans, <small>D</small>-β-hydroxybutyric acid is one of two primary <a href="/wiki/Endogenous" class="mw-redirect" title="Endogenous">endogenous</a> <a href="/wiki/Agonist" title="Agonist">agonists</a> of <a href="/wiki/Hydroxycarboxylic_acid_receptor_2" title="Hydroxycarboxylic acid receptor 2">hydroxycarboxylic acid receptor 2</a> (HCA<sub>2</sub>), a <span class="nowrap"><a href="/wiki/Gi_alpha_subunit" title="Gi alpha subunit">G<sub>i/o</sub>-coupled</a></span> <a href="/wiki/G_protein-coupled_receptor" title="G protein-coupled receptor">G protein-coupled receptor</a> (GPCR).<sup id="cite_ref-IUPHAR's_comprehensive_2011_review_on_HCARs_1-0" class="reference"><a href="#cite_note-IUPHAR's_comprehensive_2011_review_on_HCARs-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-IUPHAR-DB_HCAR_family_page_2-0" class="reference"><a href="#cite_note-IUPHAR-DB_HCAR_family_page-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </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=%CE%92-Hydroxybutyric_acid&action=edit&section=1" title="Edit section: Biosynthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In humans, <span class="nowrap"><small>D</small>-β-hydroxybutyrate</span> can be synthesized in the <a href="/wiki/Liver" title="Liver">liver</a> via the <a href="/wiki/Fatty_acid_metabolism" title="Fatty acid metabolism">metabolism of fatty acids</a> (e.g., <a href="/wiki/Butyric_acid" title="Butyric acid">butyrate</a>), <a href="/wiki/Beta-Hydroxy_beta-methylbutyric_acid" class="mw-redirect" title="Beta-Hydroxy beta-methylbutyric acid"><span class="nowrap">β-hydroxy</span> <span class="nowrap">β-methylbutyrate</span></a>, and <a href="/wiki/Ketogenic_amino_acid" title="Ketogenic amino acid">ketogenic amino acids</a> through a series of reactions that metabolize these compounds into <a href="/wiki/Acetoacetate" class="mw-redirect" title="Acetoacetate">acetoacetate</a>, which is the first <a href="/wiki/Ketone_body" class="mw-redirect" title="Ketone body">ketone body</a> that is produced in the <a href="/wiki/Fasting" title="Fasting">fasting</a> state. The biosynthesis of <span class="nowrap"><small>D</small>-β-hydroxybutyrate</span> from acetoacetate is catalyzed by the <a href="/wiki/3-hydroxybutyrate_dehydrogenase" class="mw-redirect" title="3-hydroxybutyrate dehydrogenase">β-hydroxybutyrate dehydrogenase</a> <a href="/wiki/Enzyme" title="Enzyme">enzyme</a>. </p><p>Butyrate can also be metabolized into <span class="nowrap"><small>D</small>-β-hydroxybutyrate</span> via a second <a href="/wiki/Metabolic_pathway" title="Metabolic pathway">metabolic pathway</a> that does not involve acetoacetate as a metabolic intermediate. This metabolic pathway is as follows:<sup id="cite_ref-Butyrate_metabolism_3-0" class="reference"><a href="#cite_note-Butyrate_metabolism-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p> <dl><dd>butyrate→<a href="/wiki/Butyryl-CoA" title="Butyryl-CoA">butyryl-CoA</a>→<a href="/wiki/Crotonyl-CoA" title="Crotonyl-CoA">crotonyl-CoA</a>→<a href="/wiki/%CE%92-hydroxybutyryl-CoA" class="mw-redirect" title="Β-hydroxybutyryl-CoA">β-hydroxybutyryl-CoA</a>→<a href="/wiki/Poly-%CE%B2-hydroxybutyrate" class="mw-redirect" title="Poly-β-hydroxybutyrate">poly-β-hydroxybutyrate</a>→<span class="nowrap"><small>D</small>-β-</span>(<span class="nowrap"><small>D</small>-β-hydroxybutyryloxy</span>)<span class="nowrap">-butyrate</span>→<span class="nowrap"><small>D</small>-β-hydroxybutyrate</span></dd></dl> <p>The last reaction in this metabolic pathway, which involves the conversion of <span class="nowrap"><small>D</small>-β-</span>(<span class="nowrap"><small>D</small>-β-hydroxybutyryloxy</span>)<span class="nowrap">-butyrate</span> into <span class="nowrap"><small>D</small>-β-hydroxybutyrate</span>, is catalyzed by the <a href="/wiki/Hydroxybutyrate-dimer_hydrolase" title="Hydroxybutyrate-dimer hydrolase">hydroxybutyrate-dimer hydrolase</a> enzyme.<sup id="cite_ref-Butyrate_metabolism_3-1" class="reference"><a href="#cite_note-Butyrate_metabolism-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p><p>The concentration of β-hydroxybutyrate in human blood plasma, as with other <a href="/wiki/Ketone_bodies" title="Ketone bodies">ketone bodies</a>, increases through <a href="/wiki/Ketosis" title="Ketosis">ketosis</a>.<sup id="cite_ref-Medscape2015_4-0" class="reference"><a href="#cite_note-Medscape2015-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> This elevated β-hydroxybutyrate level is naturally expected, as β-hydroxybutyrate is formed from acetoacetate. The compound can be used as an energy source by the brain and skeletal muscle when <a href="/wiki/Blood_glucose" class="mw-redirect" title="Blood glucose">blood glucose</a> is low.<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><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><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><sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Diabetic" class="mw-redirect" title="Diabetic">Diabetic</a> patients can have their ketone levels tested via urine or blood to indicate <a href="/wiki/Diabetic_ketoacidosis" title="Diabetic ketoacidosis">diabetic ketoacidosis</a>. In <a href="/wiki/Alcoholic_ketoacidosis" title="Alcoholic ketoacidosis">alcoholic ketoacidosis</a>, this ketone body is produced in greatest concentration. Ketogenesis occurs if <a href="/wiki/Oxaloacetate" class="mw-redirect" title="Oxaloacetate">oxaloacetate</a> in the liver cells is depleted, a circumstance created by reduced carbohydrate intake (through diet or starvation); prolonged, excessive <a href="/wiki/Alcohol_(drug)" title="Alcohol (drug)">alcohol</a> consumption; and/or insulin deficiency. Because oxaloacetate is crucial for entry of <a href="/wiki/Acetyl-CoA" title="Acetyl-CoA">acetyl-CoA</a> into the TCA cycle, the rapid production of acetyl-CoA from fatty acid oxidation in the absence of ample oxaloacetate overwhelms the decreased capacity of the TCA cycle, and the resultant excess of acetyl-CoA is shunted towards ketone body production.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (June 2016)">citation needed</span></a></i>]</sup> </p> <div class="skin-invert-image"> <table role="presentation" cellpadding="0" style="border-spacing:0; clear:left; float:left;"> <tbody><tr> <td><div class="thumb tleft"> <div class="thumbinner" style="width:602px;"> <div style="clear: both; font-weight: bold; font-size: 106.4%; text-align: center; background-color: #F0F8FF;margin-bottom:3px;"><a href="/wiki/Leucine#Metabolism_in_humans" title="Leucine">Leucine metabolism in humans</a></div> <div style="position:relative; width:600px; height:436px; overflow:hidden; border:solid #ccc 1px; background-color:white;"> <div style="left:0px; top:0px; width:600px; position:absolute"> <span typeof="mw:File"><a href="https://commons.wikimedia.org/wiki/File:HMB_biosynthesis_and_metabolism_diagram_-_no_labels.svg" title="commons:File:HMB biosynthesis and metabolism diagram - no labels.svg"><img alt="Diagram of leucine, HMB, and isovaleryl-CoA metabolism in humans" src="//upload.wikimedia.org/wikipedia/commons/thumb/0/03/HMB_biosynthesis_and_metabolism_diagram_-_no_labels.svg/600px-HMB_biosynthesis_and_metabolism_diagram_-_no_labels.svg.png" decoding="async" width="600" height="436" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/03/HMB_biosynthesis_and_metabolism_diagram_-_no_labels.svg/900px-HMB_biosynthesis_and_metabolism_diagram_-_no_labels.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/03/HMB_biosynthesis_and_metabolism_diagram_-_no_labels.svg/1200px-HMB_biosynthesis_and_metabolism_diagram_-_no_labels.svg.png 2x" data-file-width="2126" data-file-height="1545" /></a></span> </div> <div style="text-align:center; font-size:12px; line-height:110%"> <div style="background-color:transparent; color:black"><div id="annotation_180x2" style="position:absolute; left:180px; top:2px; font-size:18px; font-size:18; line-height:20px;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Leucine" title="Leucine"><span class="nowrap"><span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">L</span></span>-Leucine</span></a></span></div> <div id="annotation_96x37" style="position:absolute; left:96px; top:37px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Branched-chain_amino_acid_aminotransferase" title="Branched-chain amino acid aminotransferase">Branched-chain amino<br />acid aminotransferase</a></span></div> <div id="annotation_240x30" style="position:absolute; left:240px; top:30px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/%CE%91-Ketoglutarate" class="mw-redirect" title="Α-Ketoglutarate">α-Ketoglutarate</a></span></div> <div id="annotation_243x61" style="position:absolute; left:243px; top:61px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Glutamate" class="mw-redirect" title="Glutamate">Glutamate</a></span></div> <div id="annotation_466x75" style="position:absolute; left:466px; top:75px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Glutamate" class="mw-redirect" title="Glutamate">Glutamate</a></span></div> <div id="annotation_383x30" style="position:absolute; left:383px; top:30px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Alanine" title="Alanine">Alanine</a></span></div> <div id="annotation_383x62" style="position:absolute; left:383px; top:62px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Pyruvate" class="mw-redirect" title="Pyruvate">Pyruvate</a></span></div> <div id="annotation_75x85" style="position:absolute; left:75px; top:85px; font-size:15px; font-size:15; line-height:17px;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Skeletal_muscle" title="Skeletal muscle">Muscle</a>: <a href="/wiki/Alpha-Ketoisocaproic_acid" class="mw-redirect" title="Alpha-Ketoisocaproic acid">α-Ketoisocaproate</a> (α-KIC)</span></div> <div id="annotation_82x128" style="position:absolute; left:82px; top:128px; font-size:15px; font-size:15; line-height:17px;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Liver" title="Liver">Liver</a>: <a href="/wiki/Alpha-Ketoisocaproic_acid" class="mw-redirect" title="Alpha-Ketoisocaproic acid">α-Ketoisocaproate</a> (α-KIC)</span></div> <div id="annotation_300x106" style="position:absolute; left:300px; top:106px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Branched-chain_%CE%B1-ketoacid_dehydrogenase" class="mw-redirect" title="Branched-chain α-ketoacid dehydrogenase">Branched-chain α-ketoacid<br />dehydrogenase</a> (<a href="/wiki/Mitochondria" class="mw-redirect" title="Mitochondria">mitochondria</a>)</span></div> <div id="annotation_93x156" style="position:absolute; left:93px; top:156px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/4-Hydroxyphenylpyruvate_dioxygenase" title="4-Hydroxyphenylpyruvate dioxygenase">KIC-dioxygenase</a><br />(<a href="/wiki/Cytosol" title="Cytosol">cytosol</a>)</span></div> <div id="annotation_465x126" style="position:absolute; left:465px; top:126px; font-size:15px; font-size:15; line-height:17px;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Isovaleryl-CoA" title="Isovaleryl-CoA">Isovaleryl-CoA</a></span></div> <div id="annotation_85x198" style="position:absolute; left:85px; top:198px; font-size:15px; font-size:15; line-height:17px;"><span style="background-color:; color:inherit;"><a href="/wiki/%CE%92-Hydroxy_%CE%B2-methylbutyric_acid" title="Β-Hydroxy β-methylbutyric acid"><b>β-Hydroxy<br />β-methylbutyrate</b></a><br />(<b>HMB</b>)</span></div> <div id="annotation_2x205" style="position:absolute; left:2px; top:205px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Excretion" title="Excretion">Excreted</a><br />in urine<br />(10–40%)</span></div> <p><br /> </p> <div id="annotation_239x217" style="position:absolute; left:239px; top:217px; font-size:13px; font-size:13; line-height:15px;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Beta-Hydroxy_beta-methylbutyryl-CoA" class="mw-redirect" title="Beta-Hydroxy beta-methylbutyryl-CoA">HMB-CoA</a></span></div> <div id="annotation_175x269" style="position:absolute; left:175px; top:269px; font-size:13px; font-size:13; line-height:15px;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/HMG-CoA" title="HMG-CoA">β-Hydroxy β-methylglutaryl-CoA</a><br />(HMG-CoA)</span></div> <div id="annotation_445x208" style="position:absolute; left:445px; top:208px; font-size:13px; font-size:13; line-height:15px;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Methylcrotonyl-CoA" title="Methylcrotonyl-CoA">β-Methylcrotonyl-CoA</a><br />(MC-CoA)</span></div> <div id="annotation_442x269" style="position:absolute; left:442px; top:269px; font-size:13px; font-size:13; line-height:15px;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/3-Methylglutaconyl-CoA" title="3-Methylglutaconyl-CoA">β-Methylglutaconyl-CoA</a><br />(MG-CoA)</span></div> <div id="annotation_395x148" style="position:absolute; left:395px; top:148px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Carbon_dioxide" title="Carbon dioxide">CO<sub>2</sub></a></span></div> <div id="annotation_221x246" style="position:absolute; left:221px; top:246px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Carbon_dioxide" title="Carbon dioxide">CO<sub>2</sub></a></span></div> <div id="annotation_214x163" style="position:absolute; left:214px; top:163px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Oxygen" title="Oxygen">O<sub>2</sub></a></span></div> <div id="annotation_211x186" style="position:absolute; left:211px; top:186px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Carbon_dioxide" title="Carbon dioxide">CO<sub>2</sub></a></span></div> <div id="annotation_426x239" style="position:absolute; left:426px; top:239px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Properties_of_water" title="Properties of water">H<sub>2</sub>O</a></span></div> <div id="annotation_458x246" style="position:absolute; left:458px; top:246px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Carbon_dioxide" title="Carbon dioxide">CO<sub>2</sub></a></span></div> <div id="annotation_422x297" style="position:absolute; left:422px; top:297px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Properties_of_water" title="Properties of water">H<sub>2</sub>O</a></span></div> <div id="annotation_242x316" style="position:absolute; left:242px; top:316px; line-height:110%;"><span style="background-color:transparent; color:inherit;">(<a href="/wiki/Liver" title="Liver">liver</a>)<br /><a href="/wiki/HMG-CoA_lyase" class="mw-redirect" title="HMG-CoA lyase">HMG-CoA<br />lyase</a></span></div> <div id="annotation_314x208" style="position:absolute; left:314px; top:208px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Enoyl-CoA_hydratase" title="Enoyl-CoA hydratase">Enoyl-CoA hydratase</a></span></div> <div id="annotation_511x163" style="position:absolute; left:511px; top:163px; font-size:12px; font-size:12; line-height:14px; text-align:left;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Isovaleryl-CoA_dehydrogenase" title="Isovaleryl-CoA dehydrogenase">Isovaleryl-CoA<br />dehydrogenase</a></span></div> <div id="annotation_511x238" style="position:absolute; left:511px; top:238px; font-size:12px; font-size:12; line-height:14px; text-align:left;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Methylcrotonyl-CoA_carboxylase" title="Methylcrotonyl-CoA carboxylase">MC-CoA<br />carboxylase</a></span></div> <div id="annotation_376x254" style="position:absolute; left:376px; top:254px; font-size:12px; font-size:12; line-height:14px; text-align:center;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Methylglutaconyl-CoA_hydratase" title="Methylglutaconyl-CoA hydratase">MG-CoA<br />hydratase</a></span></div> <div id="annotation_59x316" style="position:absolute; left:59px; top:316px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/HMG-CoA_reductase" title="HMG-CoA reductase">HMG-CoA<br />reductase</a></span></div> <div id="annotation_410x331" style="position:absolute; left:410px; top:331px; font-size:12px; font-size:12; line-height:14px; text-align:right;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/HMG-CoA_synthase" class="mw-redirect" title="HMG-CoA synthase">HMG-CoA <br />synthase</a></span></div> <div id="annotation_205x387" style="position:absolute; left:205px; top:387px; font-size:12px; font-size:12; line-height:14px; text-align:left;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/3-Hydroxybutyrate_dehydrogenase" title="3-Hydroxybutyrate dehydrogenase">β-Hydroxybutyrate<br />dehydrogenase</a></span></div> <div id="annotation_80x385" style="position:absolute; left:80px; top:385px; font-size:12px; font-size:12; line-height:14px; text-align:left;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/File:Mevalonate_pathway.svg" title="File:Mevalonate pathway.svg">Mevalonate<br />pathway</a></span></div> <div id="annotation_389x385" style="position:absolute; left:389px; top:385px; font-size:12px; font-size:12; line-height:14px;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Thiolase" title="Thiolase">Thiolase</a></span></div> <div id="annotation_274x236" style="position:absolute; left:274px; top:236px; font-size:12px; font-size:12; line-height:14px; text-align:left;"><span style="background-color:transparent; color:inherit;">Unknown<br />enzyme</span></div> <div id="annotation_152x420" style="position:absolute; left:152px; top:420px; font-size:13px; font-size:13; line-height:15px;"><span style="background-color:; color:inherit;"><a href="/wiki/Beta-Hydroxybutyric_acid" class="mw-redirect" title="Beta-Hydroxybutyric acid">β-Hydroxybutyrate</a></span></div> <div id="annotation_432x395" style="position:absolute; left:432px; top:395px; font-size:13px; font-size:13; line-height:15px;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Acetoacetyl-CoA" title="Acetoacetyl-CoA">Acetoacetyl-CoA</a></span></div> <div id="annotation_328x395" style="position:absolute; left:328px; top:395px; font-size:13px; font-size:13; line-height:15px;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Acetyl-CoA" title="Acetyl-CoA">Acetyl-CoA</a></span></div> <div id="annotation_164x365" style="position:absolute; left:164px; top:365px; font-size:13px; font-size:13; line-height:15px;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Acetoacetate" class="mw-redirect" title="Acetoacetate">Acetoacetate</a></span></div> <div id="annotation_44x365" style="position:absolute; left:44px; top:365px; font-size:13px; font-size:13; line-height:15px;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Mevalonate" class="mw-redirect" title="Mevalonate">Mevalonate</a></span></div> <div id="annotation_43x420" style="position:absolute; left:43px; top:420px; font-size:13px; font-size:13; line-height:15px;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Cholesterol" title="Cholesterol">Cholesterol</a></span></div> <div id="annotation_206x209" style="position:absolute; left:206px; top:209px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>note 1<span class="cite-bracket">]</span></a></sup></span></div></div> </div> </div> <div class="thumbcaption" style="clear:left"><div style="float:left;margin-right:0.5em"><span typeof="mw:File"><span title="The image above contains clickable links"><img alt="The image above contains clickable links" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Interactive_icon.svg/18px-Interactive_icon.svg.png" decoding="async" width="18" height="27" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Interactive_icon.svg/27px-Interactive_icon.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Interactive_icon.svg/36px-Interactive_icon.svg.png 2x" data-file-width="133" data-file-height="200" /></span></span></div>Acetoacetate, the metabolic precursor of β-hydroxybutyrate, is a metabolite of <a href="/wiki/Fatty_acid" title="Fatty acid">fatty acids</a>, <a href="/wiki/Ketogenic_amino_acid" title="Ketogenic amino acid">ketogenic amino acids</a> such as <a href="/wiki/Leucine" title="Leucine">leucine</a><sup id="cite_ref-HMG_biosynthesis_12-0" class="reference"><a href="#cite_note-HMG_biosynthesis-12"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> and <a href="/wiki/Isoleucine" title="Isoleucine">isoleucine</a>,<sup id="cite_ref-HMG_biosynthesis_12-1" class="reference"><a href="#cite_note-HMG_biosynthesis-12"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> and <a href="/wiki/Beta-Hydroxy_beta-methylbutyric_acid" class="mw-redirect" title="Beta-Hydroxy beta-methylbutyric acid"><span class="nowrap">β-hydroxy</span> <span class="nowrap">β-methylbutyrate</span></a></div> </div> </div> </td></tr></tbody></table> </div> <div style="clear:both;" class=""></div> <div class="mw-heading mw-heading2"><h2 id="Biological_activity">Biological activity</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%CE%92-Hydroxybutyric_acid&action=edit&section=2" title="Edit section: Biological activity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1251242444">.mw-parser-output .ambox{border:1px solid #a2a9b1;border-left:10px solid #36c;background-color:#fbfbfb;box-sizing:border-box}.mw-parser-output .ambox+link+.ambox,.mw-parser-output .ambox+link+style+.ambox,.mw-parser-output .ambox+link+link+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+style+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+link+.ambox{margin-top:-1px}html body.mediawiki .mw-parser-output .ambox.mbox-small-left{margin:4px 1em 4px 0;overflow:hidden;width:238px;border-collapse:collapse;font-size:88%;line-height:1.25em}.mw-parser-output .ambox-speedy{border-left:10px solid #b32424;background-color:#fee7e6}.mw-parser-output .ambox-delete{border-left:10px solid #b32424}.mw-parser-output .ambox-content{border-left:10px solid #f28500}.mw-parser-output .ambox-style{border-left:10px solid #fc3}.mw-parser-output .ambox-move{border-left:10px solid #9932cc}.mw-parser-output .ambox-protection{border-left:10px solid #a2a9b1}.mw-parser-output .ambox .mbox-text{border:none;padding:0.25em 0.5em;width:100%}.mw-parser-output .ambox .mbox-image{border:none;padding:2px 0 2px 0.5em;text-align:center}.mw-parser-output .ambox .mbox-imageright{border:none;padding:2px 0.5em 2px 0;text-align:center}.mw-parser-output .ambox .mbox-empty-cell{border:none;padding:0;width:1px}.mw-parser-output .ambox .mbox-image-div{width:52px}@media(min-width:720px){.mw-parser-output .ambox{margin:0 10%}}@media print{body.ns-0 .mw-parser-output .ambox{display:none!important}}</style><table class="box-Expand_section plainlinks metadata ambox ambox-content" role="presentation"><tbody><tr><td class="mbox-image"><div class="mbox-image-div"><span typeof="mw:File"><a href="/wiki/File:Wiki_letter_w_cropped.svg" class="mw-file-description"><img alt="[icon]" src="//upload.wikimedia.org/wikipedia/commons/thumb/1/1c/Wiki_letter_w_cropped.svg/44px-Wiki_letter_w_cropped.svg.png" decoding="async" width="44" height="31" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/1c/Wiki_letter_w_cropped.svg/66px-Wiki_letter_w_cropped.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/1c/Wiki_letter_w_cropped.svg/88px-Wiki_letter_w_cropped.svg.png 2x" data-file-width="44" data-file-height="31" /></a></span></div></td><td class="mbox-text"><div class="mbox-text-span">This section <b>needs expansion</b> with: transporter proteins<sup id="cite_ref-β-D-hydroxybutyric_acid_IUPHAR_13-0" class="reference"><a href="#cite_note-β-D-hydroxybutyric_acid_IUPHAR-13"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> that move it across lipid membranes. You can help by <a class="external text" href="https://en.wikipedia.org/w/index.php?title=%CE%92-Hydroxybutyric_acid&action=edit&section=">adding to it</a>. <span class="date-container"><i>(<span class="date">February 2018</span>)</i></span></div></td></tr></tbody></table> <p><small>D</small>-β-Hydroxybutyric acid, along with <a href="/wiki/Butyric_acid" title="Butyric acid">butyric acid</a>, are the two primary <a href="/wiki/Endogenous" class="mw-redirect" title="Endogenous">endogenous</a> <a href="/wiki/Agonist" title="Agonist">agonists</a> of <a href="/wiki/Hydroxycarboxylic_acid_receptor_2" title="Hydroxycarboxylic acid receptor 2">hydroxycarboxylic acid receptor 2</a> (HCA<sub>2</sub>), a <span class="nowrap"><a href="/wiki/Gi_alpha_subunit" title="Gi alpha subunit">G<sub>i/o</sub>-coupled</a></span> <a href="/wiki/GPCR" class="mw-redirect" title="GPCR">GPCR</a>.<sup id="cite_ref-IUPHAR's_comprehensive_2011_review_on_HCARs_1-1" class="reference"><a href="#cite_note-IUPHAR's_comprehensive_2011_review_on_HCARs-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-IUPHAR-DB_HCAR_family_page_2-1" class="reference"><a href="#cite_note-IUPHAR-DB_HCAR_family_page-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-β-D-hydroxybutyric_acid_IUPHAR_13-1" class="reference"><a href="#cite_note-β-D-hydroxybutyric_acid_IUPHAR-13"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> </p><p>β-Hydroxybutyric acid is able to cross the <a href="/wiki/Blood-brain-barrier" class="mw-redirect" title="Blood-brain-barrier">blood-brain-barrier</a> into the <a href="/wiki/Central_nervous_system" title="Central nervous system">central nervous system</a>.<sup id="cite_ref-pmid27253067_14-0" class="reference"><a href="#cite_note-pmid27253067-14"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> Levels of β-hydroxybutyric acid increase in the <a href="/wiki/Liver" title="Liver">liver</a>, <a href="/wiki/Heart" title="Heart">heart</a>, <a href="/wiki/Muscle" title="Muscle">muscle</a>, <a href="/wiki/Brain" title="Brain">brain</a>, and other tissues with <a href="/wiki/Exercise" title="Exercise">exercise</a>, <a href="/wiki/Calorie_restriction" title="Calorie restriction">calorie restriction</a>, <a href="/wiki/Fasting" title="Fasting">fasting</a>, and <a href="/wiki/Ketogenic_diet" title="Ketogenic diet">ketogenic diets</a>.<sup id="cite_ref-pmid27253067_14-1" class="reference"><a href="#cite_note-pmid27253067-14"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> The compound has been found to act as a <a href="/wiki/Histone_deacetylase_inhibitor" title="Histone deacetylase inhibitor">histone deacetylase (HDAC) inhibitor</a>.<sup id="cite_ref-pmid27253067_14-2" class="reference"><a href="#cite_note-pmid27253067-14"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> Through inhibition of the HDAC class I <a href="/wiki/Isoenzyme" class="mw-redirect" title="Isoenzyme">isoenzymes</a> <a href="/wiki/HDAC2" class="mw-redirect" title="HDAC2">HDAC2</a> and <a href="/wiki/HDAC3" title="HDAC3">HDAC3</a>, β-hydroxybutyric acid has been found to increase <a href="/wiki/Brain-derived_neurotrophic_factor" title="Brain-derived neurotrophic factor">brain-derived neurotrophic factor</a> (BDNF) levels and <a href="/wiki/TrkB" class="mw-redirect" title="TrkB">TrkB</a> <a href="/wiki/Cell_signaling" title="Cell signaling">signaling</a> in the <a href="/wiki/Hippocampus" title="Hippocampus">hippocampus</a>.<sup id="cite_ref-pmid27253067_14-3" class="reference"><a href="#cite_note-pmid27253067-14"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> Moreover, a rodent study found that prolonged exercise increases plasma β-hydroxybutyrate concentrations, which induces <a href="/wiki/Promoter_(genetics)" title="Promoter (genetics)">promoters</a> of the BDNF gene in the hippocampus.<sup id="cite_ref-pmid27253067_14-4" class="reference"><a href="#cite_note-pmid27253067-14"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> These findings may have clinical relevance in the treatment of <a href="/wiki/Depression_(mood)" title="Depression (mood)">depression</a>, <a href="/wiki/Anxiety" title="Anxiety">anxiety</a>, and <a href="/wiki/Cognitive_impairment" title="Cognitive impairment">cognitive impairment</a>.<sup id="cite_ref-pmid27253067_14-5" class="reference"><a href="#cite_note-pmid27253067-14"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> </p><p>In <a href="/wiki/Epilepsy" title="Epilepsy">epilepsy</a> patients on the ketogenic diet, blood β-hydroxybutyrate levels correlate best with degree of <a href="/wiki/Seizure" title="Seizure">seizure</a> control. The threshold for optimal <a href="/wiki/Anticonvulsant" title="Anticonvulsant">anticonvulsant</a> effect appears to be approximately 4 mmol/L.<sup id="cite_ref-pmid11198492_15-0" class="reference"><a href="#cite_note-pmid11198492-15"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Laboratory_and_industrial_chemistry">Laboratory and industrial chemistry</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%CE%92-Hydroxybutyric_acid&action=edit&section=3" title="Edit section: Laboratory and industrial chemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>β-Hydroxybutyric acid is the precursor to polyesters, which are <a href="/wiki/Biodegradable_plastics" class="mw-redirect" title="Biodegradable plastics">biodegradable plastics</a>. This polymer, <a href="/wiki/Polyhydroxybutyrate" title="Polyhydroxybutyrate">poly(3-hydroxybutyrate)</a>, is also <a href="/wiki/Natural_product" title="Natural product">naturally produced</a> by the bacteria <i><a href="/wiki/Alcaligenes_eutrophus" class="mw-redirect" title="Alcaligenes eutrophus">Alcaligenes eutrophus</a></i>.<sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> </p><p>β-Hydroxybutyrate can be extracted from poly(3-hydroxybutyrate) by acid <a href="/wiki/Hydrolysis" title="Hydrolysis">hydrolysis</a>.<sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p><p>The concentration of <span class="nowrap">β-hydroxybutyrate</span> in <a href="/wiki/Blood_plasma" title="Blood plasma">blood plasma</a> is measured through a test that uses <a href="/wiki/%CE%92-hydroxybutyrate_dehydrogenase" class="mw-redirect" title="Β-hydroxybutyrate dehydrogenase">β-hydroxybutyrate dehydrogenase</a>, with <a href="/wiki/Nicotinamide_adenine_dinucleotide" title="Nicotinamide adenine dinucleotide">NAD<sup>+</sup></a> as an electron-accepting cofactor. The conversion of <span class="nowrap">β-hydroxybutyrate</span> to acetoacetate, which is catalyzed by this enzyme, reduces the NAD<sup>+</sup> to <a href="/wiki/Nicotinamide_adenine_dinucleotide" title="Nicotinamide adenine dinucleotide">NADH</a>, generating an electrical change; the magnitude of this change can then be used to extrapolate the amount of <span class="nowrap">β-hydroxybutyrate</span> in the sample. </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=%CE%92-Hydroxybutyric_acid&action=edit&section=4" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Gamma-Hydroxybutyric_acid" class="mw-redirect" title="Gamma-Hydroxybutyric acid">Gamma-Hydroxybutyric acid</a></li> <li><a href="/wiki/%CE%92-Hydroxy_%CE%B2-methylbutyric_acid" title="Β-Hydroxy β-methylbutyric acid">β-Hydroxy β-methylbutyric acid</a> (HMB)</li> <li><a href="/wiki/Hydroxybutyric_acid" title="Hydroxybutyric acid">Hydroxybutyric acid</a></li> <li><a href="/wiki/Ketogenesis" title="Ketogenesis">Ketogenesis</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="Notes">Notes</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%CE%92-Hydroxybutyric_acid&action=edit&section=5" title="Edit section: Notes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap"><ol class="references"> <li id="cite_note-11"><span class="mw-cite-backlink"><b><a href="#cite_ref-11">^</a></b></span> <span class="reference-text">This reaction is catalyzed by an unknown <a href="/wiki/Thioesterase" title="Thioesterase">thioesterase</a> enzyme.<sup id="cite_ref-HMB-CoA_⇔_HMB_9-0" class="reference"><a href="#cite_note-HMB-CoA_⇔_HMB-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid21918059_10-0" class="reference"><a href="#cite_note-pmid21918059-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup></span> </li> </ol></div></div> <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=%CE%92-Hydroxybutyric_acid&action=edit&section=6" 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-IUPHAR's_comprehensive_2011_review_on_HCARs-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-IUPHAR's_comprehensive_2011_review_on_HCARs_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-IUPHAR's_comprehensive_2011_review_on_HCARs_1-1"><sup><i><b>b</b></i></sup></a></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="CITEREFOffermannsCollettiLovenbergSemple2011" class="citation journal cs1">Offermanns S, Colletti SL, Lovenberg TW, Semple G, Wise A, IJzerman AP (June 2011). <a rel="nofollow" class="external text" href="https://doi.org/10.1124%2Fpr.110.003301">"International Union of Basic and Clinical Pharmacology. 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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" 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href="/wiki/Geranyl_pyrophosphate" title="Geranyl pyrophosphate">Geranyl pyrophosphate</a></li> <li><a href="/wiki/Geranylgeranyl_pyrophosphate" title="Geranylgeranyl pyrophosphate">Geranylgeranyl pyrophosphate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Carotenoid" title="Carotenoid">Carotenoid</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Prephytoene_diphosphate" title="Prephytoene diphosphate">Prephytoene diphosphate</a></li> <li><a href="/wiki/Phytoene" title="Phytoene">Phytoene</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Non-mevalonate_pathway" title="Non-mevalonate pathway">Non-mevalonate pathway</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/1-Deoxy-D-xylulose_5-phosphate" title="1-Deoxy-D-xylulose 5-phosphate">DOXP</a></li> <li><a href="/wiki/2-C-methylerythritol_4-phosphate" class="mw-redirect" title="2-C-methylerythritol 4-phosphate">MEP</a></li> <li><a href="/wiki/4-diphosphocytidyl-2-C-methylerythritol" class="mw-redirect" title="4-diphosphocytidyl-2-C-methylerythritol">CDP-ME</a></li> <li><a href="/wiki/4-diphosphocytidyl-2-C-methyl-D-erythritol_2-phosphate" class="mw-redirect" title="4-diphosphocytidyl-2-C-methyl-D-erythritol 2-phosphate">CDP-MEP</a></li> <li><a href="/wiki/2-C-methyl-D-erythritol_2,4-cyclopyrophosphate" class="mw-redirect" title="2-C-methyl-D-erythritol 2,4-cyclopyrophosphate">MEcPP</a></li> <li><a href="/wiki/(E)-4-Hydroxy-3-methyl-but-2-enyl_pyrophosphate" title="(E)-4-Hydroxy-3-methyl-but-2-enyl pyrophosphate">HMB-PP</a></li> <li><a href="/wiki/Isopentenyl_pyrophosphate" title="Isopentenyl pyrophosphate">IPP</a></li> <li><a href="/wiki/Dimethylallyl_pyrophosphate" title="Dimethylallyl pyrophosphate">DMAPP</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">To <a href="/wiki/Cholesterol" title="Cholesterol">Cholesterol</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Farnesyl_pyrophosphate" title="Farnesyl pyrophosphate">Farnesyl pyrophosphate</a></li> <li><a href="/wiki/Squalene" title="Squalene">Squalene</a></li> <li><a href="/wiki/2,3-Oxidosqualene" title="2,3-Oxidosqualene">2,3-Oxidosqualene</a></li> <li><a href="/wiki/Lanosterol" title="Lanosterol">Lanosterol</a></li></ul> <ul><li><a href="/wiki/Lanosterol" title="Lanosterol">Lanosterol</a></li> <li><a href="/w/index.php?title=14-demethyllanosterol&action=edit&redlink=1" class="new" title="14-demethyllanosterol (page does not exist)">14-demethyllanosterol</a></li> <li><a href="/w/index.php?title=4alpha-Methylzymosterol&action=edit&redlink=1" class="new" title="4alpha-Methylzymosterol (page does not exist)">4alpha-Methylzymosterol</a></li> <li><a href="/w/index.php?title=Zymosterone&action=edit&redlink=1" class="new" title="Zymosterone (page does not exist)">Zymosterone</a></li> <li><a href="/wiki/Zymosterol" title="Zymosterol">Zymosterol</a></li></ul> <ul><li><a href="/wiki/Zymosterol" title="Zymosterol">Zymosterol</a></li> <li><a href="/w/index.php?title=Zymostenol&action=edit&redlink=1" class="new" title="Zymostenol (page does not exist)">Zymostenol</a></li> <li><a href="/wiki/Lathosterol" title="Lathosterol">Lathosterol</a></li> <li><a href="/wiki/7-Dehydrocholesterol" title="7-Dehydrocholesterol">7-Dehydrocholesterol</a></li> <li><a href="/wiki/Cholesterol" title="Cholesterol">Cholesterol</a></li></ul> <ul><li><a href="/wiki/Zymosterol" title="Zymosterol">Zymosterol</a></li> <li><a href="/w/index.php?title=Cholesta-7,24-dien-3-ol&action=edit&redlink=1" class="new" title="Cholesta-7,24-dien-3-ol (page does not exist)">Cholesta-7,24-dien-3-ol</a></li> <li><a href="/wiki/7-Dehydrodesmosterol" title="7-Dehydrodesmosterol">7-Dehydrodesmosterol</a></li> <li><a href="/wiki/Desmosterol" title="Desmosterol">Desmosterol</a></li> <li><a href="/wiki/Cholesterol" title="Cholesterol">Cholesterol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">From <a href="/wiki/Cholesterol" title="Cholesterol">Cholesterol</a> <br />to <a href="/wiki/Steroid" title="Steroid">Steroid hormones</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/22R-Hydroxycholesterol" title="22R-Hydroxycholesterol">22<i>R</i>-Hydroxycholesterol</a></li> <li><a href="/wiki/20%CE%B1,22R-Dihydroxycholesterol" title="20α,22R-Dihydroxycholesterol">20α,22<i>R</i>-Dihydroxycholesterol</a></li> <li>See <a href="/wiki/Template:Steroid_hormones" title="Template:Steroid hormones">here</a> instead.</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Nonhuman</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">To <a href="/wiki/Sitosterol" class="mw-redirect" title="Sitosterol">Sitosterol</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cycloartenol" title="Cycloartenol">Cycloartenol</a></li> <li><a href="/w/index.php?title=Cycloeucalenol&action=edit&redlink=1" class="new" title="Cycloeucalenol (page does not exist)">Cycloeucalenol</a></li> <li><a href="/wiki/Obtusifoliol" title="Obtusifoliol">Obtusifoliol</a></li> <li><a href="/wiki/4%CE%B1-methylfecosterol" class="mw-redirect" title="4α-methylfecosterol">4α-methylfecosterol</a></li> <li><a href="/wiki/Isofucosterol" title="Isofucosterol">Isofucosterol</a></li> <li><a href="/wiki/24-Methylenelophenol" title="24-Methylenelophenol">24-Methylenelophenol</a></li> <li><a href="/wiki/Sitosterol" class="mw-redirect" title="Sitosterol">Sitosterol</a></li> <li>More <a href="/wiki/Phytosterol" title="Phytosterol">Phytosterols</a> see <a href="/wiki/Template:Steroid_hormones" title="Template:Steroid hormones">here</a> instead.</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">To <a href="/wiki/Ergocalciferol" title="Ergocalciferol">Ergocalciferol</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Fecosterol" title="Fecosterol">Fecosterol</a></li> <li><a href="/wiki/Episterol" title="Episterol">Episterol</a></li> <li><a href="/wiki/Ergostatrienol" class="mw-redirect" title="Ergostatrienol">Ergostatrienol</a></li> <li><a href="/w/index.php?title=Ergostatetraenol&action=edit&redlink=1" class="new" title="Ergostatetraenol (page does not exist)">Ergostatetraenol</a></li> <li><a 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="Histone_deacetylase_inhibitors" 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:Histone_deacetylase_inhibitors" title="Template:Histone deacetylase inhibitors"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Histone_deacetylase_inhibitors" title="Template talk:Histone deacetylase inhibitors"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Histone_deacetylase_inhibitors" title="Special:EditPage/Template:Histone deacetylase inhibitors"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Histone_deacetylase_inhibitors" style="font-size:114%;margin:0 4em"><a href="/wiki/Histone_deacetylase_inhibitor" title="Histone deacetylase inhibitor">Histone deacetylase inhibitors</a></div></th></tr><tr><td colspan="2" class="navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/3,3%27-Diindolylmethane" title="3,3'-Diindolylmethane">3,3'-Diindolylmethane</a></li> <li><a href="/wiki/Beta-Hydroxybutyric_acid" class="mw-redirect" title="Beta-Hydroxybutyric acid">β-Hydroxybutyric acid (β-hydroxybutyrate)</a></li> <li><a href="/wiki/Abexinostat" title="Abexinostat">Abexinostat</a></li> <li><a href="/wiki/Acetoacetic_acid" title="Acetoacetic acid">Acetoacetic acid (acetoacetate)</a></li> <li><a href="/wiki/Allyl_mercaptan" title="Allyl mercaptan">Allyl mercaptan</a></li> <li><a href="/wiki/Apicidin" title="Apicidin">Apicidin</a></li> <li><a href="/wiki/Belinostat" title="Belinostat">Belinostat</a></li> <li><a href="/wiki/Butyric_acid" title="Butyric acid">Butyric acid (butyrate)</a></li> <li><a href="/wiki/Capsaicin" title="Capsaicin">Capsaicin</a></li> <li><a href="/w/index.php?title=Citarinostat&action=edit&redlink=1" class="new" title="Citarinostat (page does not exist)">Citarinostat</a></li> <li><a href="/wiki/Curcumin" title="Curcumin">Curcumin</a></li> <li><a href="/wiki/Diallyl_disulfide" title="Diallyl disulfide">Diallyl disulfide</a></li> <li><a href="/wiki/Entinostat" title="Entinostat">Entinostat</a></li> <li><a href="/w/index.php?title=Fimepinostat&action=edit&redlink=1" class="new" title="Fimepinostat (page does not exist)">Fimepinostat</a></li> <li><a href="/wiki/Givinostat" title="Givinostat">Givinostat</a></li> <li><a href="/wiki/Indole-3-carbinol" title="Indole-3-carbinol">Indole-3-carbinol</a></li> <li><a href="/w/index.php?title=Kevetrin&action=edit&redlink=1" class="new" title="Kevetrin (page does not exist)">Kevetrin</a></li> <li><a href="/wiki/Martinostat" title="Martinostat">Martinostat</a></li> <li><a href="/wiki/Mocetinostat" title="Mocetinostat">Mocetinostat</a></li> <li><a href="/wiki/Niacinamide" class="mw-redirect" title="Niacinamide">Niacinamide</a></li> <li><a href="/wiki/Panobinostat" title="Panobinostat">Panobinostat</a></li> <li><a href="/wiki/Parthenolide" title="Parthenolide">Parthenolide</a></li> <li><a href="/wiki/Phenylbutyrate" class="mw-redirect" title="Phenylbutyrate">Phenylbutyrate</a></li> <li><a href="/wiki/Pracinostat" title="Pracinostat">Pracinostat</a></li> <li><a href="/wiki/Quisinostat" title="Quisinostat">Quisinostat</a></li> <li><a href="/wiki/Resminostat" title="Resminostat">Resminostat</a></li> <li><a href="/wiki/Romidepsin" title="Romidepsin">Romidepsin</a></li> <li><a href="/wiki/Scriptaid" title="Scriptaid">Scriptaid</a></li> <li><a href="/wiki/Sodium_butyrate" title="Sodium butyrate">Sodium butyrate</a></li> <li><a href="/wiki/Sodium_oxybate" title="Sodium oxybate">Sodium oxybate (GHB sodium)</a></li> <li><a href="/wiki/Sodium_phenylbutyrate" title="Sodium phenylbutyrate">Sodium phenylbutyrate</a></li> <li><a href="/wiki/Sodium_valproate" class="mw-redirect" title="Sodium valproate">Sodium valproate</a></li> <li><a href="/wiki/Sulforaphane" title="Sulforaphane">Sulforaphane</a></li> <li><a href="/w/index.php?title=Trapoxin_B&action=edit&redlink=1" class="new" title="Trapoxin B (page does not exist)">Trapoxin B</a></li> <li><a href="/wiki/Trichostatin_A" title="Trichostatin A">Trichostatin A</a></li> <li><a href="/wiki/Tucidinostat" title="Tucidinostat">Tucidinostat</a></li> <li><a href="/wiki/Valnoctamide" title="Valnoctamide">Valnoctamide</a></li> <li><a href="/wiki/Valproate" title="Valproate">Valproic acid (valproate)</a></li> <li><a href="/wiki/Valproate_pivoxil" title="Valproate pivoxil">Valproate pivoxil</a></li> <li><a href="/wiki/Valproate_semisodium" class="mw-redirect" title="Valproate semisodium">Valproate semisodium</a></li> <li><a href="/wiki/Valpromide" title="Valpromide">Valpromide</a></li> <li><a href="/wiki/Vorinostat" title="Vorinostat">Vorinostat (SAHA)</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div><i><b>See also:</b> <a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></i></div></td></tr></tbody></table></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?type=1x1" 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=Β-Hydroxybutyric_acid&oldid=1256976936">https://en.wikipedia.org/w/index.php?title=Β-Hydroxybutyric_acid&oldid=1256976936</a>"</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div id="mw-normal-catlinks" class="mw-normal-catlinks"><a 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