CINXE.COM

<!DOCTYPE html> <html class="client-nojs vector-feature-language-in-header-enabled vector-feature-language-in-main-page-header-disabled vector-feature-sticky-header-disabled vector-feature-page-tools-pinned-disabled vector-feature-toc-pinned-clientpref-1 vector-feature-main-menu-pinned-disabled vector-feature-limited-width-clientpref-1 vector-feature-limited-width-content-enabled vector-feature-custom-font-size-clientpref-1 vector-feature-appearance-pinned-clientpref-1 vector-feature-night-mode-enabled skin-theme-clientpref-day vector-toc-available" lang="en" dir="ltr"> <head> <meta charset="UTF-8"> <title>Decarboxylation - Wikipedia</title> <script>(function(){var className="client-js vector-feature-language-in-header-enabled vector-feature-language-in-main-page-header-disabled vector-feature-sticky-header-disabled vector-feature-page-tools-pinned-disabled vector-feature-toc-pinned-clientpref-1 vector-feature-main-menu-pinned-disabled vector-feature-limited-width-clientpref-1 vector-feature-limited-width-content-enabled vector-feature-custom-font-size-clientpref-1 vector-feature-appearance-pinned-clientpref-1 vector-feature-night-mode-enabled skin-theme-clientpref-day vector-toc-available";var cookie=document.cookie.match(/(?:^|; )enwikimwclientpreferences=([^;]+)/);if(cookie){cookie[1].split('%2C').forEach(function(pref){className=className.replace(new RegExp('(^| )'+pref.replace(/-clientpref-\w+$|[^\w-]+/g,'')+'-clientpref-\\w+( |$)'),'$1'+pref+'$2');});}document.documentElement.className=className;}());RLCONF={"wgBreakFrames":false,"wgSeparatorTransformTable":["",""],"wgDigitTransformTable":["",""],"wgDefaultDateFormat":"dmy", "wgMonthNames":["","January","February","March","April","May","June","July","August","September","October","November","December"],"wgRequestId":"d49a7a23-d344-4555-a7f1-36919282dc28","wgCanonicalNamespace":"","wgCanonicalSpecialPageName":false,"wgNamespaceNumber":0,"wgPageName":"Decarboxylation","wgTitle":"Decarboxylation","wgCurRevisionId":1258036795,"wgRevisionId":1258036795,"wgArticleId":193461,"wgIsArticle":true,"wgIsRedirect":false,"wgAction":"view","wgUserName":null,"wgUserGroups":["*"],"wgCategories":["Articles with short description","Short description matches Wikidata","Wikipedia articles needing page number citations from April 2024","Substitution reactions"],"wgPageViewLanguage":"en","wgPageContentLanguage":"en","wgPageContentModel":"wikitext","wgRelevantPageName":"Decarboxylation","wgRelevantArticleId":193461,"wgIsProbablyEditable":true,"wgRelevantPageIsProbablyEditable":true,"wgRestrictionEdit":[],"wgRestrictionMove":[],"wgNoticeProject":"wikipedia", "wgCiteReferencePreviewsActive":false,"wgFlaggedRevsParams":{"tags":{"status":{"levels":1}}},"wgMediaViewerOnClick":true,"wgMediaViewerEnabledByDefault":true,"wgPopupsFlags":0,"wgVisualEditor":{"pageLanguageCode":"en","pageLanguageDir":"ltr","pageVariantFallbacks":"en"},"wgMFDisplayWikibaseDescriptions":{"search":true,"watchlist":true,"tagline":false,"nearby":true},"wgWMESchemaEditAttemptStepOversample":false,"wgWMEPageLength":10000,"wgRelatedArticlesCompat":[],"wgCentralAuthMobileDomain":false,"wgEditSubmitButtonLabelPublish":true,"wgULSPosition":"interlanguage","wgULSisCompactLinksEnabled":false,"wgVector2022LanguageInHeader":true,"wgULSisLanguageSelectorEmpty":false,"wgWikibaseItemId":"Q898436","wgCheckUserClientHintsHeadersJsApi":["brands","architecture","bitness","fullVersionList","mobile","model","platform","platformVersion"],"GEHomepageSuggestedEditsEnableTopics":true,"wgGETopicsMatchModeEnabled":false,"wgGEStructuredTaskRejectionReasonTextInputEnabled":false, "wgGELevelingUpEnabledForUser":false};RLSTATE={"ext.globalCssJs.user.styles":"ready","site.styles":"ready","user.styles":"ready","ext.globalCssJs.user":"ready","user":"ready","user.options":"loading","ext.cite.styles":"ready","skins.vector.search.codex.styles":"ready","skins.vector.styles":"ready","skins.vector.icons":"ready","ext.wikimediamessages.styles":"ready","ext.visualEditor.desktopArticleTarget.noscript":"ready","ext.uls.interlanguage":"ready","wikibase.client.init":"ready","ext.wikimediaBadges":"ready"};RLPAGEMODULES=["ext.cite.ux-enhancements","mediawiki.page.media","site","mediawiki.page.ready","mediawiki.toc","skins.vector.js","ext.centralNotice.geoIP","ext.centralNotice.startUp","ext.gadget.ReferenceTooltips","ext.gadget.switcher","ext.urlShortener.toolbar","ext.centralauth.centralautologin","mmv.bootstrap","ext.popups","ext.visualEditor.desktopArticleTarget.init","ext.visualEditor.targetLoader","ext.echo.centralauth","ext.eventLogging","ext.wikimediaEvents", "ext.navigationTiming","ext.uls.interface","ext.cx.eventlogging.campaigns","ext.cx.uls.quick.actions","wikibase.client.vector-2022","ext.checkUser.clientHints","ext.growthExperiments.SuggestedEditSession","wikibase.sidebar.tracking"];</script> <script>(RLQ=window.RLQ||[]).push(function(){mw.loader.impl(function(){return["user.options@12s5i",function($,jQuery,require,module){mw.user.tokens.set({"patrolToken":"+\\","watchToken":"+\\","csrfToken":"+\\"}); }];});});</script> <link rel="stylesheet" href="/w/load.php?lang=en&modules=ext.cite.styles%7Cext.uls.interlanguage%7Cext.visualEditor.desktopArticleTarget.noscript%7Cext.wikimediaBadges%7Cext.wikimediamessages.styles%7Cskins.vector.icons%2Cstyles%7Cskins.vector.search.codex.styles%7Cwikibase.client.init&only=styles&skin=vector-2022"> <script async="" src="/w/load.php?lang=en&modules=startup&only=scripts&raw=1&skin=vector-2022"></script> <meta name="ResourceLoaderDynamicStyles" content=""> <link rel="stylesheet" href="/w/load.php?lang=en&modules=site.styles&only=styles&skin=vector-2022"> <meta name="generator" content="MediaWiki 1.44.0-wmf.4"> <meta name="referrer" content="origin"> <meta name="referrer" content="origin-when-cross-origin"> <meta name="robots" content="max-image-preview:standard"> <meta name="format-detection" content="telephone=no"> <meta name="viewport" content="width=1120"> <meta property="og:title" content="Decarboxylation - Wikipedia"> <meta property="og:type" content="website"> <link rel="preconnect" href="//upload.wikimedia.org"> <link rel="alternate" media="only screen and (max-width: 640px)" href="//en.m.wikipedia.org/wiki/Decarboxylation"> <link rel="alternate" type="application/x-wiki" title="Edit this page" href="/w/index.php?title=Decarboxylation&action=edit"> <link rel="apple-touch-icon" href="/static/apple-touch/wikipedia.png"> <link rel="icon" href="/static/favicon/wikipedia.ico"> <link rel="search" type="application/opensearchdescription+xml" href="/w/rest.php/v1/search" title="Wikipedia (en)"> <link rel="EditURI" type="application/rsd+xml" href="//en.wikipedia.org/w/api.php?action=rsd"> <link rel="canonical" href="https://en.wikipedia.org/wiki/Decarboxylation"> <link rel="license" href="https://creativecommons.org/licenses/by-sa/4.0/deed.en"> <link rel="alternate" type="application/atom+xml" title="Wikipedia Atom feed" href="/w/index.php?title=Special:RecentChanges&feed=atom"> <link rel="dns-prefetch" href="//meta.wikimedia.org" /> <link rel="dns-prefetch" href="//login.wikimedia.org"> </head> <body class="skin--responsive skin-vector skin-vector-search-vue mediawiki ltr sitedir-ltr mw-hide-empty-elt ns-0 ns-subject mw-editable page-Decarboxylation rootpage-Decarboxylation skin-vector-2022 action-view"><a class="mw-jump-link" href="#bodyContent">Jump to content</a> <div class="vector-header-container"> <header class="vector-header mw-header"> <div class="vector-header-start"> <nav class="vector-main-menu-landmark" aria-label="Site"> <div id="vector-main-menu-dropdown" class="vector-dropdown vector-main-menu-dropdown vector-button-flush-left vector-button-flush-right" > <input type="checkbox" id="vector-main-menu-dropdown-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-main-menu-dropdown" class="vector-dropdown-checkbox " aria-label="Main menu" > <label id="vector-main-menu-dropdown-label" for="vector-main-menu-dropdown-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-menu mw-ui-icon-wikimedia-menu"></span> <span class="vector-dropdown-label-text">Main menu</span> </label> <div class="vector-dropdown-content"> <div id="vector-main-menu-unpinned-container" class="vector-unpinned-container"> <div id="vector-main-menu" class="vector-main-menu vector-pinnable-element"> <div class="vector-pinnable-header vector-main-menu-pinnable-header vector-pinnable-header-unpinned" data-feature-name="main-menu-pinned" data-pinnable-element-id="vector-main-menu" data-pinned-container-id="vector-main-menu-pinned-container" data-unpinned-container-id="vector-main-menu-unpinned-container" > <div class="vector-pinnable-header-label">Main menu</div> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-main-menu.pin">move to sidebar</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-main-menu.unpin">hide</button> </div> <div id="p-navigation" class="vector-menu mw-portlet mw-portlet-navigation" > <div class="vector-menu-heading"> Navigation </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="n-mainpage-description" class="mw-list-item"><a href="/wiki/Main_Page" title="Visit the main page [z]" accesskey="z"><span>Main page</span></a></li><li id="n-contents" class="mw-list-item"><a href="/wiki/Wikipedia:Contents" title="Guides to browsing Wikipedia"><span>Contents</span></a></li><li id="n-currentevents" class="mw-list-item"><a href="/wiki/Portal:Current_events" title="Articles related to current events"><span>Current events</span></a></li><li id="n-randompage" class="mw-list-item"><a href="/wiki/Special:Random" title="Visit a randomly selected article [x]" accesskey="x"><span>Random article</span></a></li><li id="n-aboutsite" class="mw-list-item"><a href="/wiki/Wikipedia:About" title="Learn about Wikipedia and how it works"><span>About Wikipedia</span></a></li><li id="n-contactpage" class="mw-list-item"><a href="//en.wikipedia.org/wiki/Wikipedia:Contact_us" title="How to contact Wikipedia"><span>Contact us</span></a></li> </ul> </div> </div> <div id="p-interaction" class="vector-menu mw-portlet mw-portlet-interaction" > <div class="vector-menu-heading"> Contribute </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="n-help" class="mw-list-item"><a href="/wiki/Help:Contents" title="Guidance on how to use and edit Wikipedia"><span>Help</span></a></li><li id="n-introduction" class="mw-list-item"><a href="/wiki/Help:Introduction" title="Learn how to edit Wikipedia"><span>Learn to edit</span></a></li><li id="n-portal" class="mw-list-item"><a href="/wiki/Wikipedia:Community_portal" title="The hub for editors"><span>Community portal</span></a></li><li id="n-recentchanges" class="mw-list-item"><a href="/wiki/Special:RecentChanges" title="A list of recent changes to Wikipedia [r]" accesskey="r"><span>Recent changes</span></a></li><li id="n-upload" class="mw-list-item"><a href="/wiki/Wikipedia:File_upload_wizard" title="Add images or other media for use on Wikipedia"><span>Upload file</span></a></li> </ul> </div> </div> </div> </div> </div> </div> </nav> <a href="/wiki/Main_Page" class="mw-logo"> <img class="mw-logo-icon" src="/static/images/icons/wikipedia.png" alt="" aria-hidden="true" height="50" width="50"> <span class="mw-logo-container skin-invert"> <img class="mw-logo-wordmark" alt="Wikipedia" src="/static/images/mobile/copyright/wikipedia-wordmark-en.svg" style="width: 7.5em; height: 1.125em;"> <img class="mw-logo-tagline" alt="The Free Encyclopedia" src="/static/images/mobile/copyright/wikipedia-tagline-en.svg" width="117" height="13" style="width: 7.3125em; height: 0.8125em;"> </span> </a> </div> <div class="vector-header-end"> <div id="p-search" role="search" class="vector-search-box-vue vector-search-box-collapses vector-search-box-show-thumbnail vector-search-box-auto-expand-width vector-search-box"> <a href="/wiki/Special:Search" class="cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only search-toggle" title="Search Wikipedia [f]" accesskey="f"><span class="vector-icon mw-ui-icon-search mw-ui-icon-wikimedia-search"></span> <span>Search</span> </a> <div class="vector-typeahead-search-container"> <div class="cdx-typeahead-search cdx-typeahead-search--show-thumbnail cdx-typeahead-search--auto-expand-width"> <form action="/w/index.php" id="searchform" class="cdx-search-input cdx-search-input--has-end-button"> <div id="simpleSearch" class="cdx-search-input__input-wrapper" data-search-loc="header-moved"> <div class="cdx-text-input cdx-text-input--has-start-icon"> <input class="cdx-text-input__input" type="search" name="search" placeholder="Search Wikipedia" aria-label="Search Wikipedia" autocapitalize="sentences" title="Search Wikipedia [f]" accesskey="f" id="searchInput" > <span class="cdx-text-input__icon cdx-text-input__start-icon"></span> </div> <input type="hidden" name="title" value="Special:Search"> </div> <button class="cdx-button cdx-search-input__end-button">Search</button> </form> </div> </div> </div> <nav class="vector-user-links vector-user-links-wide" aria-label="Personal tools"> <div class="vector-user-links-main"> <div id="p-vector-user-menu-preferences" class="vector-menu mw-portlet emptyPortlet" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> </ul> </div> </div> <div id="p-vector-user-menu-userpage" class="vector-menu mw-portlet emptyPortlet" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> </ul> </div> </div> <nav class="vector-appearance-landmark" aria-label="Appearance"> <div id="vector-appearance-dropdown" class="vector-dropdown " title="Change the appearance of the page's font size, width, and color" > <input type="checkbox" id="vector-appearance-dropdown-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-appearance-dropdown" class="vector-dropdown-checkbox " aria-label="Appearance" > <label id="vector-appearance-dropdown-label" for="vector-appearance-dropdown-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-appearance mw-ui-icon-wikimedia-appearance"></span> <span class="vector-dropdown-label-text">Appearance</span> </label> <div class="vector-dropdown-content"> <div id="vector-appearance-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <div id="p-vector-user-menu-notifications" class="vector-menu mw-portlet emptyPortlet" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> </ul> </div> </div> <div id="p-vector-user-menu-overflow" class="vector-menu mw-portlet" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="pt-sitesupport-2" class="user-links-collapsible-item mw-list-item user-links-collapsible-item"><a data-mw="interface" href="https://donate.wikimedia.org/wiki/Special:FundraiserRedirector?utm_source=donate&utm_medium=sidebar&utm_campaign=C13_en.wikipedia.org&uselang=en" class=""><span>Donate</span></a> </li> <li id="pt-createaccount-2" class="user-links-collapsible-item mw-list-item user-links-collapsible-item"><a data-mw="interface" href="/w/index.php?title=Special:CreateAccount&returnto=Decarboxylation" title="You are encouraged to create an account and log in; however, it is not mandatory" class=""><span>Create account</span></a> </li> <li id="pt-login-2" class="user-links-collapsible-item mw-list-item user-links-collapsible-item"><a data-mw="interface" href="/w/index.php?title=Special:UserLogin&returnto=Decarboxylation" title="You're encouraged to log in; however, it's not mandatory. [o]" accesskey="o" class=""><span>Log in</span></a> </li> </ul> </div> </div> </div> <div id="vector-user-links-dropdown" class="vector-dropdown vector-user-menu vector-button-flush-right vector-user-menu-logged-out" title="Log in and more options" > <input type="checkbox" id="vector-user-links-dropdown-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-user-links-dropdown" class="vector-dropdown-checkbox " aria-label="Personal tools" > <label id="vector-user-links-dropdown-label" for="vector-user-links-dropdown-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-ellipsis mw-ui-icon-wikimedia-ellipsis"></span> <span class="vector-dropdown-label-text">Personal tools</span> </label> <div class="vector-dropdown-content"> <div id="p-personal" class="vector-menu mw-portlet mw-portlet-personal user-links-collapsible-item" title="User menu" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="pt-sitesupport" class="user-links-collapsible-item mw-list-item"><a href="https://donate.wikimedia.org/wiki/Special:FundraiserRedirector?utm_source=donate&utm_medium=sidebar&utm_campaign=C13_en.wikipedia.org&uselang=en"><span>Donate</span></a></li><li id="pt-createaccount" class="user-links-collapsible-item mw-list-item"><a href="/w/index.php?title=Special:CreateAccount&returnto=Decarboxylation" title="You are encouraged to create an account and log in; however, it is not mandatory"><span class="vector-icon mw-ui-icon-userAdd mw-ui-icon-wikimedia-userAdd"></span> <span>Create account</span></a></li><li id="pt-login" class="user-links-collapsible-item mw-list-item"><a href="/w/index.php?title=Special:UserLogin&returnto=Decarboxylation" title="You're encouraged to log in; however, it's not mandatory. [o]" accesskey="o"><span class="vector-icon mw-ui-icon-logIn mw-ui-icon-wikimedia-logIn"></span> <span>Log in</span></a></li> </ul> </div> </div> <div id="p-user-menu-anon-editor" class="vector-menu mw-portlet mw-portlet-user-menu-anon-editor" > <div class="vector-menu-heading"> Pages for logged out editors <a href="/wiki/Help:Introduction" aria-label="Learn more about editing"><span>learn more</span></a> </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="pt-anoncontribs" class="mw-list-item"><a href="/wiki/Special:MyContributions" title="A list of edits made from this IP address [y]" accesskey="y"><span>Contributions</span></a></li><li id="pt-anontalk" class="mw-list-item"><a href="/wiki/Special:MyTalk" title="Discussion about edits from this IP address [n]" accesskey="n"><span>Talk</span></a></li> </ul> </div> </div> </div> </div> </nav> </div> </header> </div> <div class="mw-page-container"> <div class="mw-page-container-inner"> <div class="vector-sitenotice-container"> <div id="siteNotice"></div> </div> <div class="vector-column-start"> <div class="vector-main-menu-container"> <div id="mw-navigation"> <nav id="mw-panel" class="vector-main-menu-landmark" aria-label="Site"> <div id="vector-main-menu-pinned-container" class="vector-pinned-container"> </div> </nav> </div> </div> <div class="vector-sticky-pinned-container"> <nav id="mw-panel-toc" aria-label="Contents" data-event-name="ui.sidebar-toc" class="mw-table-of-contents-container vector-toc-landmark"> <div id="vector-toc-pinned-container" class="vector-pinned-container"> <div id="vector-toc" class="vector-toc vector-pinnable-element"> <div class="vector-pinnable-header vector-toc-pinnable-header vector-pinnable-header-pinned" data-feature-name="toc-pinned" data-pinnable-element-id="vector-toc" > <h2 class="vector-pinnable-header-label">Contents</h2> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-toc.pin">move to sidebar</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-toc.unpin">hide</button> </div> <ul class="vector-toc-contents" id="mw-panel-toc-list"> <li id="toc-mw-content-text" class="vector-toc-list-item vector-toc-level-1"> <a href="#" class="vector-toc-link"> <div class="vector-toc-text">(Top)</div> </a> </li> <li id="toc-In_organic_chemistry" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#In_organic_chemistry"> <div class="vector-toc-text"> <span class="vector-toc-numb">1</span> <span>In organic chemistry</span> </div> </a> <ul id="toc-In_organic_chemistry-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-In_biochemistry" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#In_biochemistry"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>In biochemistry</span> </div> </a> <button aria-controls="toc-In_biochemistry-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle In biochemistry subsection</span> </button> <ul id="toc-In_biochemistry-sublist" class="vector-toc-list"> <li id="toc-Decarboxylation_of_amino_acids" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Decarboxylation_of_amino_acids"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.1</span> <span>Decarboxylation of amino acids</span> </div> </a> <ul id="toc-Decarboxylation_of_amino_acids-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Fatty_acid_synthesis" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Fatty_acid_synthesis"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.2</span> <span>Fatty acid synthesis</span> </div> </a> <ul id="toc-Fatty_acid_synthesis-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Case_studies" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Case_studies"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Case studies</span> </div> </a> <ul id="toc-Case_studies-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span class="vector-dropdown-label-text">Toggle the table of contents</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Decarboxylation</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 32 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-32" 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">32 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/%D9%86%D8%B2%D8%B9_%D8%A7%D9%84%D9%83%D8%B1%D8%A8%D9%88%D9%83%D8%B3%D9%8A%D9%84" title="نزع الكربوكسيل – Arabic" lang="ar" hreflang="ar" data-title="نزع الكربوكسيل" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%94%D0%B5%D0%BA%D0%B0%D1%80%D0%B1%D0%BE%D0%BA%D1%81%D0%B8%D0%BB%D0%B8%D1%80%D0%B0%D0%BD%D0%B5" title="Декарбоксилиране – Bulgarian" lang="bg" hreflang="bg" data-title="Декарбоксилиране" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target"><span>Български</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Descarboxilaci%C3%B3" title="Descarboxilació – Catalan" lang="ca" hreflang="ca" data-title="Descarboxilació" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Dekarboxylace" title="Dekarboxylace – Czech" lang="cs" hreflang="cs" data-title="Dekarboxylace" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Decarboxylase" title="Decarboxylase – Danish" lang="da" hreflang="da" data-title="Decarboxylase" data-language-autonym="Dansk" data-language-local-name="Danish" class="interlanguage-link-target"><span>Dansk</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Decarboxylierung" title="Decarboxylierung – German" lang="de" hreflang="de" data-title="Decarboxylierung" 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/Dekarboks%C3%BC%C3%BClimine" title="Dekarboksüülimine – Estonian" lang="et" hreflang="et" data-title="Dekarboksüülimine" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Descarboxilaci%C3%B3n" title="Descarboxilación – Spanish" lang="es" hreflang="es" data-title="Descarboxilación" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Deskarboxilazio" title="Deskarboxilazio – Basque" lang="eu" hreflang="eu" data-title="Deskarboxilazio" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%DA%A9%D8%B1%D8%A8%D9%88%DA%A9%D8%B3%DB%8C%D9%84%E2%80%8C%D8%B2%D8%AF%D8%A7%DB%8C%DB%8C" title="کربوکسیل‌زدایی – Persian" lang="fa" hreflang="fa" data-title="کربوکسیل‌زدایی" 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/D%C3%A9carboxylation" title="Décarboxylation – French" lang="fr" hreflang="fr" data-title="Décarboxylation" 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/Descarboxilaci%C3%B3n" title="Descarboxilación – Galician" lang="gl" hreflang="gl" data-title="Descarboxilación" 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/%ED%83%88%EC%B9%B4%EB%B3%B5%EC%8B%A4%ED%99%94" title="탈카복실화 – Korean" lang="ko" hreflang="ko" data-title="탈카복실화" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D4%B4%D5%A5%D5%AF%D5%A1%D6%80%D5%A2%D6%85%D6%84%D5%BD%D5%AB%D5%AC%D5%A1%D6%81%D5%B8%D6%82%D5%B4" title="Դեկարբօքսիլացում – Armenian" lang="hy" hreflang="hy" data-title="Դեկարբօքսիլացում" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Dekarboksilasi" title="Dekarboksilasi – Indonesian" lang="id" hreflang="id" data-title="Dekarboksilasi" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target"><span>Bahasa Indonesia</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Decarbossilazione" title="Decarbossilazione – Italian" lang="it" hreflang="it" data-title="Decarbossilazione" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-ky mw-list-item"><a href="https://ky.wikipedia.org/wiki/%D0%94%D0%B5%D0%BA%D0%B0%D1%80%D0%B1%D0%BE%D0%BA%D1%81%D0%B8%D0%BB%D0%B4%D3%A9%D3%A9" title="Декарбоксилдөө – Kyrgyz" lang="ky" hreflang="ky" data-title="Декарбоксилдөө" data-language-autonym="Кыргызча" data-language-local-name="Kyrgyz" class="interlanguage-link-target"><span>Кыргызча</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Dekarboxilez%C3%A9s" title="Dekarboxilezés – Hungarian" lang="hu" hreflang="hu" data-title="Dekarboxilezés" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Penyahkarboksilan" title="Penyahkarboksilan – Malay" lang="ms" hreflang="ms" data-title="Penyahkarboksilan" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" class="interlanguage-link-target"><span>Bahasa Melayu</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Decarboxylering" title="Decarboxylering – Dutch" lang="nl" hreflang="nl" data-title="Decarboxylering" 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/%E8%84%B1%E7%82%AD%E9%85%B8" title="脱炭酸 – Japanese" lang="ja" hreflang="ja" data-title="脱炭酸" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-uz mw-list-item"><a href="https://uz.wikipedia.org/wiki/Dekarboksillanish" title="Dekarboksillanish – Uzbek" lang="uz" hreflang="uz" data-title="Dekarboksillanish" data-language-autonym="Oʻzbekcha / ўзбекча" data-language-local-name="Uzbek" class="interlanguage-link-target"><span>Oʻzbekcha / ўзбекча</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Dekarboksylacja" title="Dekarboksylacja – Polish" lang="pl" hreflang="pl" data-title="Dekarboksylacja" 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/Descarboxila%C3%A7%C3%A3o" title="Descarboxilação – Portuguese" lang="pt" hreflang="pt" data-title="Descarboxilação" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Decarboxilare" title="Decarboxilare – Romanian" lang="ro" hreflang="ro" data-title="Decarboxilare" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%94%D0%B5%D0%BA%D0%B0%D1%80%D0%B1%D0%BE%D0%BA%D1%81%D0%B8%D0%BB%D0%B8%D1%80%D0%BE%D0%B2%D0%B0%D0%BD%D0%B8%D0%B5" title="Декарбоксилирование – Russian" lang="ru" hreflang="ru" data-title="Декарбоксилирование" 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/Dekarboxyl%C3%A1cia" title="Dekarboxylácia – Slovak" lang="sk" hreflang="sk" data-title="Dekarboxylácia" 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/Dekarboksilacija" title="Dekarboksilacija – Serbian" lang="sr" hreflang="sr" data-title="Dekarboksilacija" 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-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Dekarboksylaatio" title="Dekarboksylaatio – Finnish" lang="fi" hreflang="fi" data-title="Dekarboksylaatio" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Dekarboxylering" title="Dekarboxylering – Swedish" lang="sv" hreflang="sv" data-title="Dekarboxylering" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%94%D0%B5%D0%BA%D0%B0%D1%80%D0%B1%D0%BE%D0%BA%D1%81%D0%B8%D0%BB%D1%8E%D0%B2%D0%B0%D0%BD%D0%BD%D1%8F" title="Декарбоксилювання – Ukrainian" lang="uk" hreflang="uk" data-title="Декарбоксилювання" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E8%84%B1%E7%BE%A7%E5%8F%8D%E5%BA%94" title="脱羧反应 – Chinese" lang="zh" hreflang="zh" data-title="脱羧反应" 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/Q898436#sitelinks-wikipedia" title="Edit interlanguage links" class="wbc-editpage">Edit links</a></span></div> </div> </div> </div> </header> <div class="vector-page-toolbar"> <div class="vector-page-toolbar-container"> <div id="left-navigation"> <nav aria-label="Namespaces"> <div id="p-associated-pages" class="vector-menu vector-menu-tabs mw-portlet mw-portlet-associated-pages" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="ca-nstab-main" class="selected vector-tab-noicon mw-list-item"><a href="/wiki/Decarboxylation" title="View the content page [c]" accesskey="c"><span>Article</span></a></li><li id="ca-talk" class="vector-tab-noicon mw-list-item"><a href="/wiki/Talk:Decarboxylation" rel="discussion" title="Discuss improvements to the content page [t]" accesskey="t"><span>Talk</span></a></li> </ul> </div> </div> <div id="vector-variants-dropdown" class="vector-dropdown emptyPortlet" > <input type="checkbox" id="vector-variants-dropdown-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-variants-dropdown" class="vector-dropdown-checkbox " aria-label="Change language variant" > <label id="vector-variants-dropdown-label" for="vector-variants-dropdown-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet" aria-hidden="true" ><span class="vector-dropdown-label-text">English</span> </label> <div class="vector-dropdown-content"> <div id="p-variants" class="vector-menu mw-portlet mw-portlet-variants emptyPortlet" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> </ul> </div> </div> </div> </div> </nav> </div> <div id="right-navigation" class="vector-collapsible"> <nav aria-label="Views"> <div id="p-views" class="vector-menu vector-menu-tabs mw-portlet mw-portlet-views" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="ca-view" class="selected vector-tab-noicon mw-list-item"><a href="/wiki/Decarboxylation"><span>Read</span></a></li><li id="ca-edit" class="vector-tab-noicon mw-list-item"><a href="/w/index.php?title=Decarboxylation&action=edit" title="Edit this page [e]" accesskey="e"><span>Edit</span></a></li><li id="ca-history" class="vector-tab-noicon mw-list-item"><a href="/w/index.php?title=Decarboxylation&action=history" title="Past revisions of this page [h]" accesskey="h"><span>View history</span></a></li> </ul> </div> </div> </nav> <nav class="vector-page-tools-landmark" aria-label="Page tools"> <div id="vector-page-tools-dropdown" class="vector-dropdown vector-page-tools-dropdown" > <input type="checkbox" id="vector-page-tools-dropdown-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-tools-dropdown" class="vector-dropdown-checkbox " aria-label="Tools" > <label id="vector-page-tools-dropdown-label" for="vector-page-tools-dropdown-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet" aria-hidden="true" ><span class="vector-dropdown-label-text">Tools</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-tools-unpinned-container" class="vector-unpinned-container"> <div id="vector-page-tools" class="vector-page-tools vector-pinnable-element"> <div class="vector-pinnable-header vector-page-tools-pinnable-header vector-pinnable-header-unpinned" data-feature-name="page-tools-pinned" data-pinnable-element-id="vector-page-tools" data-pinned-container-id="vector-page-tools-pinned-container" data-unpinned-container-id="vector-page-tools-unpinned-container" > <div class="vector-pinnable-header-label">Tools</div> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-page-tools.pin">move to sidebar</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-page-tools.unpin">hide</button> </div> <div id="p-cactions" class="vector-menu mw-portlet mw-portlet-cactions emptyPortlet vector-has-collapsible-items" title="More options" > <div class="vector-menu-heading"> Actions </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="ca-more-view" class="selected vector-more-collapsible-item mw-list-item"><a href="/wiki/Decarboxylation"><span>Read</span></a></li><li id="ca-more-edit" class="vector-more-collapsible-item mw-list-item"><a href="/w/index.php?title=Decarboxylation&action=edit" title="Edit this page [e]" accesskey="e"><span>Edit</span></a></li><li id="ca-more-history" class="vector-more-collapsible-item mw-list-item"><a href="/w/index.php?title=Decarboxylation&action=history"><span>View history</span></a></li> </ul> </div> </div> <div id="p-tb" class="vector-menu mw-portlet mw-portlet-tb" > <div class="vector-menu-heading"> General </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="t-whatlinkshere" class="mw-list-item"><a href="/wiki/Special:WhatLinksHere/Decarboxylation" title="List of all English Wikipedia pages containing links to this page [j]" accesskey="j"><span>What links here</span></a></li><li id="t-recentchangeslinked" class="mw-list-item"><a href="/wiki/Special:RecentChangesLinked/Decarboxylation" rel="nofollow" title="Recent changes in pages linked from this page [k]" accesskey="k"><span>Related changes</span></a></li><li id="t-upload" class="mw-list-item"><a href="/wiki/Wikipedia:File_Upload_Wizard" title="Upload files [u]" accesskey="u"><span>Upload file</span></a></li><li id="t-specialpages" class="mw-list-item"><a href="/wiki/Special:SpecialPages" title="A list of all special pages [q]" accesskey="q"><span>Special pages</span></a></li><li id="t-permalink" class="mw-list-item"><a href="/w/index.php?title=Decarboxylation&oldid=1258036795" title="Permanent link to this revision of this page"><span>Permanent link</span></a></li><li id="t-info" class="mw-list-item"><a href="/w/index.php?title=Decarboxylation&action=info" title="More information about this page"><span>Page information</span></a></li><li id="t-cite" class="mw-list-item"><a href="/w/index.php?title=Special:CiteThisPage&page=Decarboxylation&id=1258036795&wpFormIdentifier=titleform" title="Information on how to cite this page"><span>Cite this page</span></a></li><li id="t-urlshortener" class="mw-list-item"><a href="/w/index.php?title=Special:UrlShortener&url=https%3A%2F%2Fen.wikipedia.org%2Fwiki%2FDecarboxylation"><span>Get shortened URL</span></a></li><li id="t-urlshortener-qrcode" class="mw-list-item"><a href="/w/index.php?title=Special:QrCode&url=https%3A%2F%2Fen.wikipedia.org%2Fwiki%2FDecarboxylation"><span>Download QR code</span></a></li> </ul> </div> </div> <div id="p-coll-print_export" class="vector-menu mw-portlet mw-portlet-coll-print_export" > <div class="vector-menu-heading"> Print/export </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="coll-download-as-rl" class="mw-list-item"><a href="/w/index.php?title=Special:DownloadAsPdf&page=Decarboxylation&action=show-download-screen" title="Download this page as a PDF file"><span>Download as PDF</span></a></li><li id="t-print" class="mw-list-item"><a href="/w/index.php?title=Decarboxylation&printable=yes" title="Printable version of this page [p]" accesskey="p"><span>Printable version</span></a></li> </ul> </div> </div> <div id="p-wikibase-otherprojects" class="vector-menu mw-portlet mw-portlet-wikibase-otherprojects" > <div class="vector-menu-heading"> In other projects </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="wb-otherproject-link wb-otherproject-commons mw-list-item"><a href="https://commons.wikimedia.org/wiki/Category:Decarboxylation" hreflang="en"><span>Wikimedia Commons</span></a></li><li id="t-wikibase" class="wb-otherproject-link wb-otherproject-wikibase-dataitem mw-list-item"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q898436" title="Structured data on this page hosted by Wikidata [g]" accesskey="g"><span>Wikidata item</span></a></li> </ul> </div> </div> </div> </div> </div> </div> </nav> </div> </div> </div> <div class="vector-column-end"> <div class="vector-sticky-pinned-container"> <nav class="vector-page-tools-landmark" aria-label="Page tools"> <div id="vector-page-tools-pinned-container" class="vector-pinned-container"> </div> </nav> <nav class="vector-appearance-landmark" aria-label="Appearance"> <div id="vector-appearance-pinned-container" class="vector-pinned-container"> <div id="vector-appearance" class="vector-appearance vector-pinnable-element"> <div class="vector-pinnable-header vector-appearance-pinnable-header vector-pinnable-header-pinned" data-feature-name="appearance-pinned" data-pinnable-element-id="vector-appearance" data-pinned-container-id="vector-appearance-pinned-container" data-unpinned-container-id="vector-appearance-unpinned-container" > <div class="vector-pinnable-header-label">Appearance</div> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-appearance.pin">move to sidebar</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-appearance.unpin">hide</button> </div> </div> </div> </nav> </div> </div> <div id="bodyContent" class="vector-body" aria-labelledby="firstHeading" data-mw-ve-target-container> <div class="vector-body-before-content"> <div class="mw-indicators"> </div> <div id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><style data-mw-deduplicate="TemplateStyles: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/Decarbonylation" title="Decarbonylation">Decarbonylation</a>.</div><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical reaction that removes a carboxyl group and releases carbon dioxide</div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Decarboxylation_reaction.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b7/Decarboxylation_reaction.png/440px-Decarboxylation_reaction.png" decoding="async" width="440" height="77" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b7/Decarboxylation_reaction.png/660px-Decarboxylation_reaction.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b7/Decarboxylation_reaction.png/880px-Decarboxylation_reaction.png 2x" data-file-width="2162" data-file-height="378" /></a><figcaption>Decarboxylation</figcaption></figure> <p><b>Decarboxylation</b> is a <a href="/wiki/Chemical_reaction" title="Chemical reaction">chemical reaction</a> that removes a <a href="/wiki/Carboxyl_group" class="mw-redirect" title="Carboxyl group">carboxyl group</a> and releases <a href="/wiki/Carbon_dioxide" title="Carbon dioxide">carbon dioxide</a> (CO<sub>2</sub>). Usually, decarboxylation refers to a reaction of <a href="/wiki/Carboxylic_acids" class="mw-redirect" title="Carboxylic acids">carboxylic acids</a>, removing a carbon atom from a carbon chain. The reverse process, which is the first chemical step in <a href="/wiki/Photosynthesis" title="Photosynthesis">photosynthesis</a>, is called <a href="/wiki/Carboxylation" title="Carboxylation">carboxylation</a>, the addition of CO<sub>2</sub> to a compound. Enzymes that catalyze decarboxylations are called <a href="/wiki/Decarboxylase" class="mw-redirect" title="Decarboxylase">decarboxylases</a> or, the more formal term, <a href="/wiki/Carboxy-lyases" title="Carboxy-lyases">carboxy-lyases</a> (<a href="/wiki/Enzyme_Commission_number" title="Enzyme Commission number">EC number</a> 4.1.1). </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="In_organic_chemistry">In organic chemistry</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Decarboxylation&action=edit&section=1" title="Edit section: In organic chemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The term "decarboxylation" usually means replacement of a <a href="/wiki/Carboxyl_group" class="mw-redirect" title="Carboxyl group">carboxyl group</a> (<style data-mw-deduplicate="TemplateStyles:r1123817410">.mw-parser-output .template-chem2-su{display:inline-block;font-size:80%;line-height:1;vertical-align:-0.35em}.mw-parser-output .template-chem2-su>span{display:block;text-align:left}.mw-parser-output sub.template-chem2-sub{font-size:80%;vertical-align:-0.35em}.mw-parser-output sup.template-chem2-sup{font-size:80%;vertical-align:0.65em}</style><span class="chemf nowrap">−C(O)OH</span>) with a <a href="/wiki/Hydrogen_atom" title="Hydrogen atom">hydrogen atom</a>: </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">RCO<sub class="template-chem2-sub">2</sub>H → RH + CO<sub class="template-chem2-sub">2</sub></span></dd></dl> <p>Decarboxylation is one of the oldest known organic reactions. It is one of the processes assumed to accompany <a href="/wiki/Pyrolysis" title="Pyrolysis">pyrolysis</a> and <a href="/wiki/Destructive_distillation" title="Destructive distillation">destructive distillation</a>. </p><p>Overall, decarboxylation depends upon stability of the carbanion <a href="/wiki/Synthon" title="Synthon">synthon</a> <span class="chemf nowrap">R<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:0.8em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">−</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sub></span></span></span>,<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> although the anion may not be a true <a href="/wiki/Chemical_intermediate" class="mw-redirect" title="Chemical intermediate">chemical intermediate</a>.<sup id="cite_ref-Keton_3-0" class="reference"><a href="#cite_note-Keton-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Malon_4-0" class="reference"><a href="#cite_note-Malon-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> Typically, carboxylic acids decarboxylate slowly, but carboxylic acids with an α <a href="/wiki/Electron-withdrawing_group" title="Electron-withdrawing group">electron-withdrawing group</a> (e.g. β‑<a href="/wiki/Keto_acid" title="Keto acid">keto acids</a>, β‑nitriles, α‑<a href="/wiki/Nitro_compound" title="Nitro compound">nitro</a> acids, or <a href="/wiki/Benzoic_acid" title="Benzoic acid">arylcarboxylic acids</a>) decarboxylate easily. Decarboxylation of <a href="/wiki/Sodium_chlorodifluoroacetate" title="Sodium chlorodifluoroacetate">sodium chlorodifluoroacetate</a> generates <a href="/wiki/Difluorocarbene" title="Difluorocarbene">difluorocarbene</a>: </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CF<sub class="template-chem2-sub">2</sub>ClCO<sub class="template-chem2-sub">2</sub>Na → NaCl + CF<sub class="template-chem2-sub">2</sub> + CO<sub class="template-chem2-sub">2</sub></span><sup id="cite_ref-eEROS_5-0" class="reference"><a href="#cite_note-eEROS-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup></dd></dl> <p>Decarboxylations are an important in the <a href="/wiki/Malonic_ester_synthesis" title="Malonic ester synthesis">malonic</a> and <a href="/wiki/Acetoacetic_ester_synthesis" title="Acetoacetic ester synthesis">acetoacetic ester synthesis</a>. The <a href="/wiki/Knoevenagel_condensation" title="Knoevenagel condensation">Knoevenagel condensation</a> and they allow keto acids serve as a stabilizing <a href="/wiki/Protecting_group" title="Protecting group">protecting group</a> for carboxylic acid <a href="/wiki/Enol" title="Enol">enols</a>.<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 class="noprint Inline-Template" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citing_sources" title="Wikipedia:Citing sources"><span title="This citation requires a reference to the specific page or range of pages in which the material appears. (April 2024)">page needed</span></a></i>]</sup><sup id="cite_ref-Malon_4-1" class="reference"><a href="#cite_note-Malon-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p><p>For the free acids, conditions that deprotonate the carboxyl group (possibly protonating the electron-withdrawing group to form a <a href="/wiki/Zwitterionic" class="mw-redirect" title="Zwitterionic">zwitterionic</a> <a href="/wiki/Tautomer" title="Tautomer">tautomer</a>) accelerate decarboxylation.<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> A strong <a href="/wiki/Base_(chem)" class="mw-redirect" title="Base (chem)">base</a> is key to <a href="/wiki/Ketonization" class="mw-redirect" title="Ketonization">ketonization</a>, in which a pair of carboxylic acids combine to <a href="/wiki/Ketone" title="Ketone">the eponymous functional group</a>:<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><sup id="cite_ref-Keton_3-1" class="reference"><a href="#cite_note-Keton-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-default-size mw-halign-center" typeof="mw:File/Frameless"><a href="/wiki/File:Barium_adipate_pyrolysis.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c4/Barium_adipate_pyrolysis.png/390px-Barium_adipate_pyrolysis.png" decoding="async" width="390" height="58" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c4/Barium_adipate_pyrolysis.png/585px-Barium_adipate_pyrolysis.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c4/Barium_adipate_pyrolysis.png/780px-Barium_adipate_pyrolysis.png 2x" data-file-width="2199" data-file-height="329" /></a><figcaption></figcaption></figure> <p><a href="/wiki/Transition_metal" title="Transition metal">Transition metal</a> salts, especially <a href="/wiki/Copper" title="Copper">copper</a> compounds,<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> facilitate decarboxylation via <a href="/wiki/Metal_carboxylate_complex" class="mw-redirect" title="Metal carboxylate complex">carboxylate complex</a> intermediates. Metals that catalyze <a href="/wiki/Cross-coupling_reaction" title="Cross-coupling reaction">cross-coupling reactions</a> thus treat aryl carboxylates as an aryl anion synthon; this synthetic strategy is the <a href="/wiki/Decarboxylative_cross-coupling" title="Decarboxylative cross-coupling">decarboxylative cross-coupling</a> reaction.<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p><p>Upon heating in <a href="/wiki/Cyclohexanone" title="Cyclohexanone">cyclohexanone</a>, <a href="/wiki/Amino_acid" title="Amino acid">amino acids</a> decarboxylate. In the related <a href="/wiki/Hammick_reaction" title="Hammick reaction">Hammick reaction</a>, uncatalyzed decarboxylation of a <a href="/wiki/Picolinic_acid" title="Picolinic acid">picolinic acid</a> gives a <a href="/wiki/Stable_carbene" class="mw-redirect" title="Stable carbene">stable carbene</a> that attacks a <a href="/wiki/Carbonyl" class="mw-redirect" title="Carbonyl">carbonyl</a> electrophile. </p><p><a href="/wiki/Oxidative_decarboxylation" title="Oxidative decarboxylation">Oxidative decarboxylations</a> are generally radical reactions. These include the <a href="/wiki/Kolbe_electrolysis" title="Kolbe electrolysis">Kolbe electrolysis</a> and <a href="/wiki/Hunsdiecker_reaction" title="Hunsdiecker reaction">Hunsdiecker</a>-<a href="/wiki/Kochi_reaction" title="Kochi reaction">Kochi reactions</a>. The <a href="/wiki/Barton_decarboxylation" title="Barton decarboxylation">Barton decarboxylation</a> is an unusual radical reductive decarboxylation. </p><p>As described above, most decarboxylations start with a carboxylic acid or its alkali metal salt, but the <a href="/wiki/Krapcho_decarboxylation" title="Krapcho decarboxylation">Krapcho decarboxylation</a> starts with methyl <a href="/wiki/Ester" title="Ester">esters</a>. In this case, the reaction begins with <a href="/wiki/Halide" title="Halide">halide</a>-mediated cleavage of the ester, forming the carboxylate. </p> <div class="mw-heading mw-heading2"><h2 id="In_biochemistry">In biochemistry</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Decarboxylation&action=edit&section=2" title="Edit section: In biochemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Decarboxylations are pervasive in biology. They are often classified according to the cofactors that catalyze the transformations.<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> <a href="/wiki/Biotin" title="Biotin">Biotin</a>-coupled processes effect the decarboxylation of <a href="/wiki/Malonyl-CoA" title="Malonyl-CoA">malonyl-CoA</a> to <a href="/wiki/Acetyl-CoA" title="Acetyl-CoA">acetyl-CoA</a>. <a href="/wiki/Thiamine" title="Thiamine">Thiamine</a> (T:) is the active component for decarboxylation of <a href="/wiki/Alpha-ketoacid" class="mw-redirect" title="Alpha-ketoacid">alpha-ketoacids</a>, including pyruvate: </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">T: + RC(O)CO<sub class="template-chem2-sub">2</sub>H → T=C(OH)R + CO<sub class="template-chem2-sub">2</sub></span></dd> <dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">T=C(OH)R + R'COOH → T! : + RC(O)CH(OH)R'</span></dd></dl> <p><a href="/wiki/Pyridoxal_phosphate" title="Pyridoxal phosphate">Pyridoxal phosphate</a> promotes decarboxylation of amino acids. <a href="/wiki/Flavin_group" title="Flavin group">Flavin</a>-dependent decarboxylases are involved in transformations of cysteine. Iron-based hydroxylases operate by reductive activation of <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">O<sub class="template-chem2-sub">2</sub></span> using the decarboxylation of <a href="/wiki/Alpha-ketoglutarate" class="mw-redirect" title="Alpha-ketoglutarate">alpha-ketoglutarate</a> as an electron donor. The decarboxylation can be depicted as such: </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">RC(O)CO<sub class="template-chem2-sub">2</sub>Fe O<sub class="template-chem2-sub">2</sub> → RCO<sub class="template-chem2-sub">2</sub>Fe{IV}=O + CO<sub class="template-chem2-sub">2</sub></span></dd> <dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">RCO<sub class="template-chem2-sub">2</sub>Fe=O + R'H → RCO<sub class="template-chem2-sub">2</sub>Fe + R'OH</span></dd></dl> <div class="mw-heading mw-heading3"><h3 id="Decarboxylation_of_amino_acids">Decarboxylation of amino acids</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Decarboxylation&action=edit&section=3" title="Edit section: Decarboxylation of amino acids"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Common <a href="/wiki/Biosynthesis" title="Biosynthesis">biosynthetic</a> <a href="/wiki/Oxidative_decarboxylation" title="Oxidative decarboxylation">oxidative decarboxylations</a> of <a href="/wiki/Amino_acid" title="Amino acid">amino acids</a> to <a href="/wiki/Amine" title="Amine">amines</a> are: </p> <ul><li><a href="/wiki/Tryptophan" title="Tryptophan">tryptophan</a> to <a href="/wiki/Tryptamine" title="Tryptamine">tryptamine</a></li> <li><a href="/wiki/Phenylalanine" title="Phenylalanine">phenylalanine</a> to <a href="/wiki/Phenylethylamine" class="mw-redirect" title="Phenylethylamine">phenylethylamine</a></li> <li><a href="/wiki/Tyrosine" title="Tyrosine">tyrosine</a> to <a href="/wiki/Tyramine" title="Tyramine">tyramine</a></li> <li><a href="/wiki/Histidine" title="Histidine">histidine</a> to <a href="/wiki/Histamine" title="Histamine">histamine</a></li> <li><a href="/wiki/Serine" title="Serine">serine</a> to <a href="/wiki/Ethanolamine" title="Ethanolamine">ethanolamine</a></li> <li><a href="/wiki/Glutamic_acid" title="Glutamic acid">glutamic acid</a> to <a href="/wiki/GABA" title="GABA">GABA</a></li> <li><a href="/wiki/Lysine" title="Lysine">lysine</a> to <a href="/wiki/Cadaverine" title="Cadaverine">cadaverine</a></li> <li><a href="/wiki/Arginine" title="Arginine">arginine</a> to <a href="/wiki/Agmatine" title="Agmatine">agmatine</a></li> <li><a href="/wiki/Ornithine" title="Ornithine">ornithine</a> to <a href="/wiki/Putrescine" title="Putrescine">putrescine</a></li> <li><a href="/wiki/5-HTP" class="mw-redirect" title="5-HTP">5-HTP</a> to <a href="/wiki/Serotonin" title="Serotonin">serotonin</a></li> <li><a href="/wiki/L-DOPA" title="L-DOPA">L-DOPA</a> to <a href="/wiki/Dopamine" title="Dopamine">dopamine</a></li></ul> <p>Other decarboxylation reactions from the <a href="/wiki/Citric_acid_cycle" title="Citric acid cycle">citric acid cycle</a> include: </p> <ul><li><a href="/wiki/Pyruvate" class="mw-redirect" title="Pyruvate">pyruvate</a> to <a href="/wiki/Acetyl_coenzyme_A" class="mw-redirect" title="Acetyl coenzyme A">acetyl-CoA</a> (see <a href="/wiki/Pyruvate_decarboxylation" title="Pyruvate decarboxylation">pyruvate decarboxylation</a>)</li> <li><a href="/wiki/Oxalosuccinic_acid" title="Oxalosuccinic acid">oxalosuccinate</a> to α-<a href="/wiki/Alpha-Ketoglutaric_acid" class="mw-redirect" title="Alpha-Ketoglutaric acid">ketoglutarate</a></li> <li>α-<a href="/wiki/Alpha-Ketoglutaric_acid" class="mw-redirect" title="Alpha-Ketoglutaric acid">ketoglutarate</a> to <a href="/wiki/Succinyl_coenzyme_A" class="mw-redirect" title="Succinyl coenzyme A">succinyl-CoA</a>.</li></ul> <div class="mw-heading mw-heading3"><h3 id="Fatty_acid_synthesis">Fatty acid synthesis</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Decarboxylation&action=edit&section=4" title="Edit section: Fatty acid synthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:Saturated_Fatty_Acid_Synthesis.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f8/Saturated_Fatty_Acid_Synthesis.svg/400px-Saturated_Fatty_Acid_Synthesis.svg.png" decoding="async" width="400" height="206" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f8/Saturated_Fatty_Acid_Synthesis.svg/600px-Saturated_Fatty_Acid_Synthesis.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f8/Saturated_Fatty_Acid_Synthesis.svg/800px-Saturated_Fatty_Acid_Synthesis.svg.png 2x" data-file-width="512" data-file-height="264" /></a><figcaption> Synthesis of saturated fatty acids via fatty acid synthase II in <i>E. coli</i></figcaption></figure> <p>Straight-chain fatty acid synthesis occurs by recurring reactions involving decarboxylation of <a href="/wiki/Malonyl-CoA" title="Malonyl-CoA">malonyl-CoA</a>.<sup id="cite_ref-lipidlib_12-0" class="reference"><a href="#cite_note-lipidlib-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Case_studies">Case studies</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Decarboxylation&action=edit&section=5" title="Edit section: Case studies"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Tetrahydrocannabinolicacid.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/1d/Tetrahydrocannabinolicacid.svg/220px-Tetrahydrocannabinolicacid.svg.png" decoding="async" width="220" height="128" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/1d/Tetrahydrocannabinolicacid.svg/330px-Tetrahydrocannabinolicacid.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/1d/Tetrahydrocannabinolicacid.svg/440px-Tetrahydrocannabinolicacid.svg.png 2x" data-file-width="653" data-file-height="380" /></a><figcaption>Tetrahydrocannabinolic acid. The decarboxylation of this compound by heat is essential for the psychoactive effect of smoked <a href="/wiki/Cannabis" title="Cannabis">cannabis</a>, and depends on conversion of the <a href="/wiki/Enol" title="Enol">enol</a> to a keto group when the alpha carbon is protonated.</figcaption></figure> <p>Upon heating, Δ9-tetrahydrocannabinolic acid decarboxylates to give the psychoactive compound Δ9-<a href="/wiki/Tetrahydrocannabinol" title="Tetrahydrocannabinol">Tetrahydrocannabinol</a>.<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> When cannabis is heated in vacuum, the decarboxylation of <a href="/wiki/Tetrahydrocannabinolic_acid" title="Tetrahydrocannabinolic acid">tetrahydrocannabinolic acid</a> (THCA) appears to follow <a href="/wiki/First_order_kinetics" class="mw-redirect" title="First order kinetics">first order kinetics</a>. The log fraction of THCA present decreases steadily over time, and the rate of decrease varies according to temperature. At 10-degree increments from 100 to 140 °C, half of the THCA is consumed in 30, 11, 6, 3, and 2 minutes; hence the rate constant follows <a href="/wiki/Arrhenius%27_law" class="mw-redirect" title="Arrhenius' law">Arrhenius' law</a>, ranging between 10<sup>−8</sup> and 10<sup>−5</sup> in a linear log-log relationship with inverse temperature. However, modelling of decarboxylation of <a href="/wiki/Salicylic_acid" title="Salicylic acid">salicylic acid</a> with a water molecule had suggested an activation barrier of 150 kJ/mol for a single molecule in solvent, much too high for the observed rate. Therefore, it was concluded that this reaction, conducted in the solid phase in plant material with a high fraction of carboxylic acids, follows a pseudo first order kinetics in which a nearby carboxylic acid precipitates without affecting the observed rate constant. Two transition states corresponding to indirect and direct keto-enol routes are possible, with energies of 93 and 104 kJ/mol. Both intermediates involve protonation of the <a href="/wiki/Alpha_carbon" class="mw-redirect" title="Alpha carbon">alpha carbon</a>, disrupting one of the double bonds of the aromatic ring and permitting the beta-keto group (which takes the form of an <a href="/wiki/Enol" title="Enol">enol</a> in THCA and THC) to participate in decarboxylation.<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>In beverages stored for long periods, very small amounts of <a href="/wiki/Benzene" title="Benzene">benzene</a> may form from <a href="/wiki/Benzoic_acid" title="Benzoic acid">benzoic acid</a> by decarboxylation catalyzed by the presence of <a href="/wiki/Ascorbic_acid" class="mw-redirect" title="Ascorbic acid">ascorbic acid</a>.<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><p>The addition of catalytic amounts of <a href="/wiki/Cyclohexenone" title="Cyclohexenone">cyclohexenone</a> has been reported to catalyze the decarboxylation of <a href="/wiki/Amino_acids" class="mw-redirect" title="Amino acids">amino acids</a>.<sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> However, using such catalysts may also yield an amount of unwanted by-products. </p> <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=Decarboxylation&action=edit&section=6" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist reflist-columns references-column-width reflist-columns-2"> <ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFMarch,_Jerry1985" class="citation cs2"><a href="/wiki/Jerry_March" title="Jerry March">March, Jerry</a> (1985), <a rel="nofollow" class="external text" href="https://www.google.co.in/books/edition/_/ZKqWAQAACAAJ?hl=en"><i>Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 3rd edition</i></a>, New York: Wiley, <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780471854722" title="Special:BookSources/9780471854722"><bdi>9780471854722</bdi></a>, <a href="/wiki/OCLC_(identifier)" class="mw-redirect" title="OCLC (identifier)">OCLC</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/oclc/642506595">642506595</a></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Advanced+Organic+Chemistry%3A+Reactions%2C+Mechanisms%2C+and+Structure%2C+3rd+edition&rft.place=New+York&rft.pub=Wiley&rft.date=1985&rft_id=info%3Aoclcnum%2F642506595&rft.isbn=9780471854722&rft.au=March%2C+Jerry&rft_id=https%3A%2F%2Fwww.google.co.in%2Fbooks%2Fedition%2F_%2FZKqWAQAACAAJ%3Fhl%3Den&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADecarboxylation" class="Z3988"></span></span> </li> <li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://www.chem.ucalgary.ca/courses/350/Carey5th/Ch19/ch19-3-4.html">"Decarboxylation, Dr. Ian A. Hunt, Department of Chemistry, University of Calgary"</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20221221053807/http://www.chem.ucalgary.ca/courses/350/Carey5th/Ch19/ch19-3-4.html">Archived</a> from the original on 2022-12-21<span class="reference-accessdate">. Retrieved <span class="nowrap">2008-12-07</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Decarboxylation%2C+Dr.+Ian+A.+Hunt%2C+Department+of+Chemistry%2C+University+of+Calgary&rft_id=http%3A%2F%2Fwww.chem.ucalgary.ca%2Fcourses%2F350%2FCarey5th%2FCh19%2Fch19-3-4.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADecarboxylation" class="Z3988"></span></span> </li> <li id="cite_note-Keton-3"><span class="mw-cite-backlink">^ <a href="#cite_ref-Keton_3-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Keton_3-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRenz2005" class="citation journal cs1">Renz, M (2005). <a rel="nofollow" class="external text" href="https://www.thevespiary.org/rhodium/Rhodium/Vespiary/talk/files/835-Thermal.Ketonization.Mechanism.and.Scopecc88.pdf">"Ketonization of Carboxylic Acids by Decarboxylation: Mechanism and Scope"</a> <span class="cs1-format">(PDF)</span>. <i>Eur. J. Org. Chem</i>. <b>2005</b> (6): 979–988. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fejoc.200400546">10.1002/ejoc.200400546</a> – via The Vespiary.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Eur.+J.+Org.+Chem.&rft.atitle=Ketonization+of+Carboxylic+Acids+by+Decarboxylation%3A+Mechanism+and+Scope&rft.volume=2005&rft.issue=6&rft.pages=979-988&rft.date=2005&rft_id=info%3Adoi%2F10.1002%2Fejoc.200400546&rft.aulast=Renz&rft.aufirst=M&rft_id=https%3A%2F%2Fwww.thevespiary.org%2Frhodium%2FRhodium%2FVespiary%2Ftalk%2Ffiles%2F835-Thermal.Ketonization.Mechanism.and.Scopecc88.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADecarboxylation" class="Z3988"></span></span> </li> <li id="cite_note-Malon-4"><span class="mw-cite-backlink">^ <a href="#cite_ref-Malon_4-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Malon_4-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.organic-chemistry.org/namedreactions/malonic-ester-synthesis.shtm">"Malonic Ester Synthesis"</a>. Organic Chemistry Portal<span class="reference-accessdate">. Retrieved <span class="nowrap">2007-10-26</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Malonic+Ester+Synthesis&rft.pub=Organic+Chemistry+Portal&rft_id=https%3A%2F%2Fwww.organic-chemistry.org%2Fnamedreactions%2Fmalonic-ester-synthesis.shtm&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADecarboxylation" class="Z3988"></span></span> </li> <li id="cite_note-eEROS-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-eEROS_5-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFTaschner2001" class="citation book cs1">Taschner, Michael J. (2001). "Sodium Chlorodifluoroacetate". <i>Encyclopedia of Reagents for Organic Synthesis</i>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F047084289X.rs058">10.1002/047084289X.rs058</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/0-471-93623-5" title="Special:BookSources/0-471-93623-5"><bdi>0-471-93623-5</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Sodium+Chlorodifluoroacetate&rft.btitle=Encyclopedia+of+Reagents+for+Organic+Synthesis&rft.date=2001&rft_id=info%3Adoi%2F10.1002%2F047084289X.rs058&rft.isbn=0-471-93623-5&rft.aulast=Taschner&rft.aufirst=Michael+J.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADecarboxylation" class="Z3988"></span></span> </li> <li id="cite_note-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-6">^</a></b></span> <span class="reference-text"><i>Organic Synthesis: The disconnection approach</i>, 2nd ed.</span> </li> <li id="cite_note-7"><span class="mw-cite-backlink"><b><a href="#cite_ref-7">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFJim_Clark2004" class="citation web cs1">Jim Clark (2004). <a rel="nofollow" class="external text" href="http://www.chemguide.co.uk/organicprops/acids/decarbox.html">"The Decarboxylation of Carboxylic Acids and their Salts"</a>. Chemguide<span class="reference-accessdate">. Retrieved <span class="nowrap">2007-10-22</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=The+Decarboxylation+of+Carboxylic+Acids+and+their+Salts&rft.pub=Chemguide&rft.date=2004&rft.au=Jim+Clark&rft_id=http%3A%2F%2Fwww.chemguide.co.uk%2Forganicprops%2Facids%2Fdecarbox.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADecarboxylation" class="Z3988"></span></span> </li> <li id="cite_note-8"><span class="mw-cite-backlink"><b><a href="#cite_ref-8">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFThorpeKon1925" class="citation journal cs1">Thorpe, J. F.; Kon, G. A. R. (1925). "Cyclopentanone". <i>Org. Synth</i>. <b>5</b>: 37. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.15227%2Forgsyn.005.0037">10.15227/orgsyn.005.0037</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Org.+Synth.&rft.atitle=Cyclopentanone&rft.volume=5&rft.pages=37&rft.date=1925&rft_id=info%3Adoi%2F10.15227%2Forgsyn.005.0037&rft.aulast=Thorpe&rft.aufirst=J.+F.&rft.au=Kon%2C+G.+A.+R.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADecarboxylation" class="Z3988"></span></span> </li> <li id="cite_note-9"><span class="mw-cite-backlink"><b><a href="#cite_ref-9">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWileySmith1953" class="citation journal cs1">Wiley, Richard H.; Smith, Newton R. (1953). <a rel="nofollow" class="external text" href="http://orgsyn.org/demo.aspx?prep=CV4P0731">"m-Nitrostyrene"</a>. <i>Organic Syntheses</i>. <b>33</b>: 62. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.15227%2Forgsyn.033.0062">10.15227/orgsyn.033.0062</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Organic+Syntheses&rft.atitle=m-Nitrostyrene&rft.volume=33&rft.pages=62&rft.date=1953&rft_id=info%3Adoi%2F10.15227%2Forgsyn.033.0062&rft.aulast=Wiley&rft.aufirst=Richard+H.&rft.au=Smith%2C+Newton+R.&rft_id=http%3A%2F%2Forgsyn.org%2Fdemo.aspx%3Fprep%3DCV4P0731&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADecarboxylation" class="Z3988"></span></span> </li> <li id="cite_note-10"><span class="mw-cite-backlink"><b><a href="#cite_ref-10">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWeaverRecioGrenningTunge2011" class="citation journal cs1">Weaver, J. D.; Recio, A.; Grenning, A. J.; Tunge, J. A. (2011). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3116714">"Transition Metal-Catalyzed Decarboxylative Allylation and Benzylation Reactions"</a>. <i>Chem. Rev</i>. <b>111</b> (3): 1846–1913. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fcr1002744">10.1021/cr1002744</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3116714">3116714</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/21235271">21235271</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Chem.+Rev.&rft.atitle=Transition+Metal-Catalyzed+Decarboxylative+Allylation+and+Benzylation+Reactions&rft.volume=111&rft.issue=3&rft.pages=1846-1913&rft.date=2011&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3116714%23id-name%3DPMC&rft_id=info%3Apmid%2F21235271&rft_id=info%3Adoi%2F10.1021%2Fcr1002744&rft.aulast=Weaver&rft.aufirst=J.+D.&rft.au=Recio%2C+A.&rft.au=Grenning%2C+A.+J.&rft.au=Tunge%2C+J.+A.&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3116714&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADecarboxylation" class="Z3988"></span></span> </li> <li id="cite_note-11"><span class="mw-cite-backlink"><b><a href="#cite_ref-11">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLi,_T.Huo,_L.Pulley,_C.Liu,_A.2012" class="citation journal cs1">Li, T.; Huo, L.; Pulley, C.; Liu, A. (2012). "Decarboxylation mechanisms in biological system. Bioorganic Chemistry". <i>Bioorganic Chemistry</i>. <b>43</b>: 2–14. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.bioorg.2012.03.001">10.1016/j.bioorg.2012.03.001</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/22534166">22534166</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Bioorganic+Chemistry&rft.atitle=Decarboxylation+mechanisms+in+biological+system.+Bioorganic+Chemistry&rft.volume=43&rft.pages=2-14&rft.date=2012&rft_id=info%3Adoi%2F10.1016%2Fj.bioorg.2012.03.001&rft_id=info%3Apmid%2F22534166&rft.au=Li%2C+T.&rft.au=Huo%2C+L.&rft.au=Pulley%2C+C.&rft.au=Liu%2C+A.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADecarboxylation" class="Z3988"></span></span> </li> <li id="cite_note-lipidlib-12"><span class="mw-cite-backlink"><b><a href="#cite_ref-lipidlib_12-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20110721024641/http://lipidlibrary.aocs.org/lipids/fa_sat/index.htm">"Fatty Acids: Straight-chain Saturated, Structure, Occurrence and Biosynthesis"</a>. <i>lipidlibrary.aocs.org</i>. Lipid Library, The American Oil Chemists' Society. 30 April 2011. Archived from <a rel="nofollow" class="external text" href="http://lipidlibrary.aocs.org/lipids/fa_sat/index.htm">the original</a> on 21 July 2011.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=lipidlibrary.aocs.org&rft.atitle=Fatty+Acids%3A+Straight-chain+Saturated%2C+Structure%2C+Occurrence+and+Biosynthesis&rft.date=2011-04-30&rft_id=http%3A%2F%2Flipidlibrary.aocs.org%2Flipids%2Ffa_sat%2Findex.htm&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADecarboxylation" class="Z3988"></span></span> </li> <li id="cite_note-13"><span class="mw-cite-backlink"><b><a href="#cite_ref-13">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPerrotin-BrunelBuijsSpronsenRoosmalen2011" class="citation journal cs1">Perrotin-Brunel, Helene; Buijs, Wim; Spronsen, Jaap van; Roosmalen, Maaike J.E. van; Peters, Cor J.; Verpoorte, Rob; Witkamp, Geert-Jan (2011). "Decarboxylation of Δ9-tetrahydrocannabinol: Kinetics and molecular modeling". <i>Journal of Molecular Structure</i>. <b>987</b> (1–3): 67–73. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2011JMoSt.987...67P">2011JMoSt.987...67P</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.molstruc.2010.11.061">10.1016/j.molstruc.2010.11.061</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Molecular+Structure&rft.atitle=Decarboxylation+of+%CE%949-tetrahydrocannabinol%3A+Kinetics+and+molecular+modeling&rft.volume=987&rft.issue=1%E2%80%933&rft.pages=67-73&rft.date=2011&rft_id=info%3Adoi%2F10.1016%2Fj.molstruc.2010.11.061&rft_id=info%3Abibcode%2F2011JMoSt.987...67P&rft.aulast=Perrotin-Brunel&rft.aufirst=Helene&rft.au=Buijs%2C+Wim&rft.au=Spronsen%2C+Jaap+van&rft.au=Roosmalen%2C+Maaike+J.E.+van&rft.au=Peters%2C+Cor+J.&rft.au=Verpoorte%2C+Rob&rft.au=Witkamp%2C+Geert-Jan&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADecarboxylation" class="Z3988"></span></span> </li> <li id="cite_note-14"><span class="mw-cite-backlink"><b><a href="#cite_ref-14">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPerrotin-BrunelBuijsSpronsenRoosmalen2011" class="citation journal cs1">Perrotin-Brunel, Helene; Buijs, Wim; Spronsen, Jaap van; Roosmalen, Maaike J.E. van; Peters, Cor J.; Verpoorte, Rob; Witkamp, Geert-Jan (February 2011). <a rel="nofollow" class="external text" href="https://www.researchgate.net/publication/251476768">"Decarboxylation of Δ9-tetrahydrocannabinol: Kinetics and molecular modeling"</a>. <i>Journal of Molecular Structure</i>. <b>987</b> (1–3): 67–73. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2011JMoSt.987...67P">2011JMoSt.987...67P</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.molstruc.2010.11.061">10.1016/j.molstruc.2010.11.061</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Molecular+Structure&rft.atitle=Decarboxylation+of+%CE%949-tetrahydrocannabinol%3A+Kinetics+and+molecular+modeling&rft.volume=987&rft.issue=1%E2%80%933&rft.pages=67-73&rft.date=2011-02&rft_id=info%3Adoi%2F10.1016%2Fj.molstruc.2010.11.061&rft_id=info%3Abibcode%2F2011JMoSt.987...67P&rft.aulast=Perrotin-Brunel&rft.aufirst=Helene&rft.au=Buijs%2C+Wim&rft.au=Spronsen%2C+Jaap+van&rft.au=Roosmalen%2C+Maaike+J.E.+van&rft.au=Peters%2C+Cor+J.&rft.au=Verpoorte%2C+Rob&rft.au=Witkamp%2C+Geert-Jan&rft_id=https%3A%2F%2Fwww.researchgate.net%2Fpublication%2F251476768&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADecarboxylation" class="Z3988"></span></span> </li> <li id="cite_note-15"><span class="mw-cite-backlink"><b><a href="#cite_ref-15">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20080326000150/http://www.cfsan.fda.gov/~dms/benzdata.html">"Data on Benzene in Soft Drinks and Other Beverages"</a>. Archived from <a rel="nofollow" class="external text" href="http://www.cfsan.fda.gov/~dms/benzdata.html">the original</a> on 2008-03-26<span class="reference-accessdate">. Retrieved <span class="nowrap">2008-03-26</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Data+on+Benzene+in+Soft+Drinks+and+Other+Beverages&rft_id=http%3A%2F%2Fwww.cfsan.fda.gov%2F~dms%2Fbenzdata.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADecarboxylation" class="Z3988"></span></span> </li> <li id="cite_note-16"><span class="mw-cite-backlink"><b><a href="#cite_ref-16">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHashimotoEdaOsanaiIwai1986" class="citation journal cs1">Hashimoto, Mitsunori; Eda, Yutaka; Osanai, Yasutomo; Iwai, Toshiaki; Aoki, Seiichi (1986). "A Novel Decarboxylation of α-Amino Acides. A Facile Method of Decarboxylation by the Use of 2-Cyclohexen-1-one as a Catalyst". <i>Chemistry Letters</i>. <b>15</b> (6): 893–896. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1246%2Fcl.1986.893">10.1246/cl.1986.893</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Chemistry+Letters&rft.atitle=A+Novel+Decarboxylation+of+%CE%B1-Amino+Acides.+A+Facile+Method+of+Decarboxylation+by+the+Use+of+2-Cyclohexen-1-one+as+a+Catalyst&rft.volume=15&rft.issue=6&rft.pages=893-896&rft.date=1986&rft_id=info%3Adoi%2F10.1246%2Fcl.1986.893&rft.aulast=Hashimoto&rft.aufirst=Mitsunori&rft.au=Eda%2C+Yutaka&rft.au=Osanai%2C+Yasutomo&rft.au=Iwai%2C+Toshiaki&rft.au=Aoki%2C+Seiichi&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADecarboxylation" class="Z3988"></span></span> </li> </ol></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=Decarboxylation&oldid=1258036795">https://en.wikipedia.org/w/index.php?title=Decarboxylation&oldid=1258036795</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">Category</a>: <ul><li><a href="/wiki/Category:Substitution_reactions" title="Category:Substitution reactions">Substitution reactions</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_with_short_description" title="Category:Articles with short description">Articles with short description</a></li><li><a href="/wiki/Category:Short_description_matches_Wikidata" title="Category:Short description matches Wikidata">Short description matches Wikidata</a></li><li><a href="/wiki/Category:Wikipedia_articles_needing_page_number_citations_from_April_2024" title="Category:Wikipedia articles needing page number citations from April 2024">Wikipedia articles needing page number citations from April 2024</a></li></ul></div></div> </div> </main> </div> <div class="mw-footer-container"> <footer id="footer" class="mw-footer" > <ul id="footer-info"> <li id="footer-info-lastmod"> This page was last edited on 17 November 2024, at 20:44<span class="anonymous-show"> (UTC)</span>.</li> <li id="footer-info-copyright">Text is available under the <a href="/wiki/Wikipedia:Text_of_the_Creative_Commons_Attribution-ShareAlike_4.0_International_License" title="Wikipedia:Text of the Creative Commons Attribution-ShareAlike 4.0 International License">Creative Commons Attribution-ShareAlike 4.0 License</a>; additional terms may apply. By using this site, you agree to the <a href="https://foundation.wikimedia.org/wiki/Special:MyLanguage/Policy:Terms_of_Use" class="extiw" title="foundation:Special:MyLanguage/Policy:Terms of Use">Terms of Use</a> and <a href="https://foundation.wikimedia.org/wiki/Special:MyLanguage/Policy:Privacy_policy" class="extiw" title="foundation:Special:MyLanguage/Policy:Privacy policy">Privacy Policy</a>. Wikipedia® is a registered trademark of the <a rel="nofollow" class="external text" href="https://wikimediafoundation.org/">Wikimedia Foundation, Inc.</a>, a non-profit organization.</li> </ul> <ul id="footer-places"> <li id="footer-places-privacy"><a href="https://foundation.wikimedia.org/wiki/Special:MyLanguage/Policy:Privacy_policy">Privacy policy</a></li> <li id="footer-places-about"><a href="/wiki/Wikipedia:About">About Wikipedia</a></li> <li id="footer-places-disclaimers"><a href="/wiki/Wikipedia:General_disclaimer">Disclaimers</a></li> <li id="footer-places-contact"><a href="//en.wikipedia.org/wiki/Wikipedia:Contact_us">Contact Wikipedia</a></li> <li id="footer-places-wm-codeofconduct"><a href="https://foundation.wikimedia.org/wiki/Special:MyLanguage/Policy:Universal_Code_of_Conduct">Code of Conduct</a></li> <li id="footer-places-developers"><a href="https://developer.wikimedia.org">Developers</a></li> <li id="footer-places-statslink"><a href="https://stats.wikimedia.org/#/en.wikipedia.org">Statistics</a></li> <li id="footer-places-cookiestatement"><a href="https://foundation.wikimedia.org/wiki/Special:MyLanguage/Policy:Cookie_statement">Cookie statement</a></li> <li id="footer-places-mobileview"><a href="//en.m.wikipedia.org/w/index.php?title=Decarboxylation&mobileaction=toggle_view_mobile" class="noprint stopMobileRedirectToggle">Mobile view</a></li> </ul> <ul id="footer-icons" class="noprint"> <li id="footer-copyrightico"><a href="https://wikimediafoundation.org/" class="cdx-button cdx-button--fake-button cdx-button--size-large cdx-button--fake-button--enabled"><img src="/static/images/footer/wikimedia-button.svg" width="84" height="29" alt="Wikimedia Foundation" loading="lazy"></a></li> <li id="footer-poweredbyico"><a href="https://www.mediawiki.org/" class="cdx-button cdx-button--fake-button cdx-button--size-large cdx-button--fake-button--enabled"><img src="/w/resources/assets/poweredby_mediawiki.svg" alt="Powered by MediaWiki" width="88" height="31" loading="lazy"></a></li> </ul> </footer> </div> </div> </div> <div class="vector-settings" id="p-dock-bottom"> <ul></ul> </div><script>(RLQ=window.RLQ||[]).push(function(){mw.config.set({"wgHostname":"mw-web.codfw.main-f69cdc8f6-b78pt","wgBackendResponseTime":145,"wgPageParseReport":{"limitreport":{"cputime":"0.347","walltime":"0.483","ppvisitednodes":{"value":1923,"limit":1000000},"postexpandincludesize":{"value":41369,"limit":2097152},"templateargumentsize":{"value":2391,"limit":2097152},"expansiondepth":{"value":17,"limit":100},"expensivefunctioncount":{"value":3,"limit":500},"unstrip-depth":{"value":1,"limit":20},"unstrip-size":{"value":59618,"limit":5000000},"entityaccesscount":{"value":0,"limit":400},"timingprofile":["100.00% 429.672 1 -total"," 45.25% 194.443 1 Template:Reflist"," 21.15% 90.882 1 Template:JerryMarch"," 19.32% 83.005 1 Template:Citation"," 16.87% 72.473 1 Template:Short_description"," 15.29% 65.679 1 Template:Page_needed"," 14.02% 60.254 1 Template:Fix"," 11.86% 50.979 8 Template:Cite_journal"," 9.42% 40.458 2 Template:Pagetype"," 8.98% 38.588 1 Template:Distinguish"]},"scribunto":{"limitreport-timeusage":{"value":"0.205","limit":"10.000"},"limitreport-memusage":{"value":6843350,"limit":52428800}},"cachereport":{"origin":"mw-web.eqiad.main-5dc468848-qsz2b","timestamp":"20241122140621","ttl":2592000,"transientcontent":false}}});});</script> <script type="application/ld+json">{"@context":"https:\/\/schema.org","@type":"Article","name":"Decarboxylation","url":"https:\/\/en.wikipedia.org\/wiki\/Decarboxylation","sameAs":"http:\/\/www.wikidata.org\/entity\/Q898436","mainEntity":"http:\/\/www.wikidata.org\/entity\/Q898436","author":{"@type":"Organization","name":"Contributors to Wikimedia projects"},"publisher":{"@type":"Organization","name":"Wikimedia Foundation, Inc.","logo":{"@type":"ImageObject","url":"https:\/\/www.wikimedia.org\/static\/images\/wmf-hor-googpub.png"}},"datePublished":"2003-03-08T13:32:56Z","dateModified":"2024-11-17T20:44:16Z","headline":"chemical reaction that removes a carboxyl group and releases carbon dioxide"}</script> </body> </html>