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occurrence</span> </div> </a> <button aria-controls="toc-Natural_occurrence-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 Natural occurrence subsection</span> </button> <ul id="toc-Natural_occurrence-sublist" class="vector-toc-list"> <li id="toc-Biological_function" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Biological_function"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1</span> <span>Biological function</span> </div> </a> <ul id="toc-Biological_function-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Metabolism" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Metabolism"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.2</span> <span>Metabolism</span> </div> </a> <ul id="toc-Metabolism-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Derivatives" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Derivatives"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Derivatives</span> </div> </a> <ul id="toc-Derivatives-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Uses" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Uses"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Uses</span> </div> </a> <ul id="toc-Uses-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Toxicity" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Toxicity"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>Toxicity</span> </div> </a> <ul id="toc-Toxicity-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">9</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">Coumarin</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 47 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-47" 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">47 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%83%D9%88%D9%85%D8%A7%D8%B1%D9%8A%D9%86" title="كومارين – Arabic" lang="ar" hreflang="ar" data-title="كومارين" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-az mw-list-item"><a href="https://az.wikipedia.org/wiki/Kumarin" title="Kumarin – Azerbaijani" lang="az" hreflang="az" data-title="Kumarin" data-language-autonym="Azərbaycanca" data-language-local-name="Azerbaijani" class="interlanguage-link-target"><span>Azərbaycanca</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%DA%A9%D9%88%D9%85%D8%A7%D8%B1%DB%8C%D9%86" title="کومارین – South Azerbaijani" lang="azb" hreflang="azb" data-title="کومارین" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-be mw-list-item"><a href="https://be.wikipedia.org/wiki/%D0%9A%D1%83%D0%BC%D0%B0%D1%80%D1%8B%D0%BD" title="Кумарын – Belarusian" lang="be" hreflang="be" data-title="Кумарын" data-language-autonym="Беларуская" data-language-local-name="Belarusian" class="interlanguage-link-target"><span>Беларуская</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%9A%D1%83%D0%BC%D0%B0%D1%80%D0%B8%D0%BD" title="Кумарин – Bulgarian" lang="bg" hreflang="bg" data-title="Кумарин" 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/Cumarina" title="Cumarina – Catalan" lang="ca" hreflang="ca" data-title="Cumarina" 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/Kumarin" title="Kumarin – Czech" lang="cs" hreflang="cs" data-title="Kumarin" 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/Kumarin" title="Kumarin – Danish" lang="da" hreflang="da" data-title="Kumarin" 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/Cumarin" title="Cumarin – German" lang="de" hreflang="de" data-title="Cumarin" 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/Kumariin" title="Kumariin – Estonian" lang="et" hreflang="et" data-title="Kumariin" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%9A%CE%BF%CF%85%CE%BC%CE%B1%CF%81%CE%AF%CE%BD%CE%B7" title="Κουμαρίνη – Greek" lang="el" hreflang="el" data-title="Κουμαρίνη" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target"><span>Ελληνικά</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Cumarina" title="Cumarina – Spanish" lang="es" hreflang="es" data-title="Cumarina" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eo mw-list-item"><a href="https://eo.wikipedia.org/wiki/Kumarino" title="Kumarino – Esperanto" lang="eo" hreflang="eo" data-title="Kumarino" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Kumarina" title="Kumarina – Basque" lang="eu" hreflang="eu" data-title="Kumarina" 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%D9%88%D9%85%D8%A7%D8%B1%DB%8C%D9%86" title="کومارین – Persian" lang="fa" hreflang="fa" data-title="کومارین" 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/Coumarine" title="Coumarine – French" lang="fr" hreflang="fr" data-title="Coumarine" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EC%BF%A0%EB%A7%88%EB%A6%B0" title="쿠마린 – Korean" lang="ko" hreflang="ko" data-title="쿠마린" 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%BF%D5%B8%D6%82%D5%B4%D5%A1%D6%80%D5%AB%D5%B6" title="Կումարին – Armenian" lang="hy" hreflang="hy" data-title="Կումարին" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-hi mw-list-item"><a href="https://hi.wikipedia.org/wiki/%E0%A4%95%E0%A5%82%E0%A4%AE%E0%A4%B0%E0%A4%BF%E0%A4%A8" title="कूमरिन – Hindi" lang="hi" hreflang="hi" data-title="कूमरिन" data-language-autonym="हिन्दी" data-language-local-name="Hindi" class="interlanguage-link-target"><span>हिन्दी</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Kumarin" title="Kumarin – Indonesian" lang="id" hreflang="id" data-title="Kumarin" 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/Cumarina" title="Cumarina – Italian" lang="it" hreflang="it" data-title="Cumarina" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%A7%D7%95%D7%9E%D7%A8%D7%99%D7%9F" title="קומרין – Hebrew" lang="he" hreflang="he" data-title="קומרין" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-jv mw-list-item"><a href="https://jv.wikipedia.org/wiki/Kumarin" title="Kumarin – Javanese" lang="jv" hreflang="jv" data-title="Kumarin" data-language-autonym="Jawa" data-language-local-name="Javanese" class="interlanguage-link-target"><span>Jawa</span></a></li><li class="interlanguage-link interwiki-ky mw-list-item"><a href="https://ky.wikipedia.org/wiki/%D0%9A%D1%83%D0%BC%D0%B0%D1%80%D0%B8%D0%BD" title="Кумарин – Kyrgyz" lang="ky" hreflang="ky" data-title="Кумарин" 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/Kumarin" title="Kumarin – Hungarian" lang="hu" hreflang="hu" data-title="Kumarin" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%9A%D1%83%D0%BC%D0%B0%D1%80%D0%B8%D0%BD" title="Кумарин – Macedonian" lang="mk" hreflang="mk" data-title="Кумарин" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-ml mw-list-item"><a href="https://ml.wikipedia.org/wiki/%E0%B4%95%E0%B5%82%E0%B4%AE%E0%B4%B1%E0%B5%88%E0%B5%BB" title="കൂമറൈൻ – Malayalam" lang="ml" hreflang="ml" data-title="കൂമറൈൻ" data-language-autonym="മലയാളം" data-language-local-name="Malayalam" class="interlanguage-link-target"><span>മലയാളം</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Cumarine" title="Cumarine – Dutch" lang="nl" hreflang="nl" data-title="Cumarine" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%AF%E3%83%9E%E3%83%AA%E3%83%B3" title="クマリン – Japanese" lang="ja" hreflang="ja" data-title="クマリン" 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-frr mw-list-item"><a href="https://frr.wikipedia.org/wiki/Cumarin" title="Cumarin – Northern Frisian" lang="frr" hreflang="frr" data-title="Cumarin" data-language-autonym="Nordfriisk" data-language-local-name="Northern Frisian" class="interlanguage-link-target"><span>Nordfriisk</span></a></li><li class="interlanguage-link interwiki-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Kumarin" title="Kumarin – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Kumarin" data-language-autonym="Norsk bokmål" data-language-local-name="Norwegian Bokmål" class="interlanguage-link-target"><span>Norsk bokmål</span></a></li><li class="interlanguage-link interwiki-uz mw-list-item"><a href="https://uz.wikipedia.org/wiki/Kumarin" title="Kumarin – Uzbek" lang="uz" hreflang="uz" data-title="Kumarin" 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-nds mw-list-item"><a href="https://nds.wikipedia.org/wiki/Cumarin" title="Cumarin – Low German" lang="nds" hreflang="nds" data-title="Cumarin" data-language-autonym="Plattdüütsch" data-language-local-name="Low German" class="interlanguage-link-target"><span>Plattdüütsch</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Kumaryna" title="Kumaryna – Polish" lang="pl" hreflang="pl" data-title="Kumaryna" 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/Cumarina" title="Cumarina – Portuguese" lang="pt" hreflang="pt" data-title="Cumarina" 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/Cumarin%C4%83" title="Cumarină – Romanian" lang="ro" hreflang="ro" data-title="Cumarină" 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%9A%D1%83%D0%BC%D0%B0%D1%80%D0%B8%D0%BD" title="Кумарин – Russian" lang="ru" hreflang="ru" data-title="Кумарин" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Kumarin" title="Kumarin – Slovenian" lang="sl" hreflang="sl" data-title="Kumarin" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Kumarin" title="Kumarin – Serbian" lang="sr" hreflang="sr" data-title="Kumarin" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Kumarin" title="Kumarin – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Kumarin" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Kumariini" title="Kumariini – Finnish" lang="fi" hreflang="fi" data-title="Kumariini" 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/Kumarin" title="Kumarin – Swedish" lang="sv" hreflang="sv" data-title="Kumarin" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B8%84%E0%B8%B9%E0%B8%A1%E0%B8%B2%E0%B8%A3%E0%B8%B4%E0%B8%99" title="คูมาริน – Thai" lang="th" hreflang="th" data-title="คูมาริน" data-language-autonym="ไทย" data-language-local-name="Thai" class="interlanguage-link-target"><span>ไทย</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Kumarin" title="Kumarin – Turkish" lang="tr" hreflang="tr" data-title="Kumarin" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%9A%D1%83%D0%BC%D0%B0%D1%80%D0%B8%D0%BD" title="Кумарин – Ukrainian" lang="uk" hreflang="uk" data-title="Кумарин" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Coumarin" title="Coumarin – Vietnamese" lang="vi" hreflang="vi" data-title="Coumarin" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target"><span>Tiếng Việt</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E9%A6%99%E8%B1%86%E7%B4%A0" title="香豆素 – Chinese" lang="zh" hreflang="zh" data-title="香豆素" 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/Q111812#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/Coumarin" title="View the content page [c]" 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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"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Aromatic chemical compound</div> <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">This article is about the natural compound. For the anticoagulants and rodenticides called "coumarins" or "coumadins", see <a href="/wiki/4-Hydroxycoumarins" title="4-Hydroxycoumarins">4-Hydroxycoumarins</a>. For other uses, see <a href="/wiki/Coumarin_derivatives" title="Coumarin derivatives">Coumarin derivatives</a>.</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Not to be confused with the medication <a href="/wiki/Warfarin" title="Warfarin">warfarin</a>, often known by the trade name "Coumadin".</div> <style data-mw-deduplicate="TemplateStyles:r1084375498">.mw-parser-output .ib-chembox{border-collapse:collapse;text-align:left}.mw-parser-output .ib-chembox td,.mw-parser-output .ib-chembox th{border:1px solid #a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}</style> <table class="infobox ib-chembox"> <caption>Coumarin </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Coumarin_acsv.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b6/Coumarin_acsv.svg/220px-Coumarin_acsv.svg.png" decoding="async" width="220" height="125" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b6/Coumarin_acsv.svg/330px-Coumarin_acsv.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b6/Coumarin_acsv.svg/440px-Coumarin_acsv.svg.png 2x" data-file-width="760" data-file-height="433" /></a></span> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Coumarin.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/71/Coumarin.png/220px-Coumarin.png" decoding="async" width="220" height="153" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/71/Coumarin.png/330px-Coumarin.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/71/Coumarin.png/440px-Coumarin.png 2x" data-file-width="1437" data-file-height="1000" /></a></span> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Coumarin_spacefill.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/4a/Coumarin_spacefill.png/220px-Coumarin_spacefill.png" decoding="async" width="220" height="168" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/4a/Coumarin_spacefill.png/330px-Coumarin_spacefill.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/4a/Coumarin_spacefill.png/440px-Coumarin_spacefill.png 2x" data-file-width="1311" data-file-height="1000" /></a></span> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Chemical_nomenclature" title="Chemical nomenclature">IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">2<i>H</i>-Chromen-2-one</div> </td></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Preferred_IUPAC_name" title="Preferred IUPAC name">Preferred IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;">2<i>H</i>-1-Benzopyran-2-one</div></div> </td></tr> <tr> <td colspan="2" style="text-align:left;">Other names <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">1-Benzopyran-2-one</div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=91-64-5">91-64-5</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=O%3DC1C%3DCc2ccccc2O1">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Beilstein_database" title="Beilstein database">Beilstein Reference</a></div> </td> <td>383644 </td></tr> <tr> <td><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=28794">CHEBI:28794</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembl/explore/compound/ChEMBL6466">ChEMBL6466</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.13848793.html">13848793</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/DrugBank" title="DrugBank">DrugBank</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.drugbank.ca"><a rel="nofollow" class="external text" href="https://www.drugbank.ca/drugs/DB04665">DB04665</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a> </td> <td><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.001.897">100.001.897</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q111812#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span> </td></tr> <tr> <td><a href="/wiki/European_Community_number" title="European Community number"><span title="European Community number (chemical identifier)">EC Number</span></a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>202-086-7</li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Gmelin_database" title="Gmelin database">Gmelin Reference</a></div> </td> <td>165222 </td></tr> <tr> <td><a href="/wiki/KEGG" title="KEGG">KEGG</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.kegg.jp"><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/D07751">D07751</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/323">323</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/RTECS" class="mw-redirect" title="RTECS">RTECS number</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>GN4200000</li></ul></div> </td></tr> <tr> <td><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/A4VZ22K1WT">A4VZ22K1WT</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID7020348">DTXSID7020348</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q111812#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></span></li></ul></div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/C9H6O2/c10-9-6-5-7-3-1-2-4-8(7)11-9/h1-6H<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: ZYGHJZDHTFUPRJ-UHFFFAOYSA-N<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div></div></li><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1/C9H6O2/c10-9-6-5-7-3-1-2-4-8(7)11-9/h1-6H</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: ZYGHJZDHTFUPRJ-UHFFFAOYAC</div></div></li></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">O=C1C=Cc2ccccc2O1</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td><span title="Carbon">C</span><sub>9</sub><span title="Hydrogen">H</span><sub>6</sub><span title="Oxygen">O</span><sub>2</sub> </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td><span class="nowrap"><span data-sort-value="7002146145000000000♠"></span>146.145</span> g·mol<sup>−1</sup>   </td></tr> <tr> <td>Appearance </td> <td>colorless to white crystals </td></tr> <tr> <td><a href="/wiki/Odor" title="Odor">Odor</a> </td> <td>pleasant, like vanilla beans </td></tr> <tr> <td><a href="/wiki/Density" title="Density">Density</a> </td> <td>0.935 g/cm<sup>3</sup> (20 °C (68 °F)) </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>71 °C (160 °F; 344 K) </td></tr> <tr> <td><a href="/wiki/Boiling_point" title="Boiling point">Boiling point</a> </td> <td>301.71 °C (575.08 °F; 574.86 K) </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Aqueous_solution" title="Aqueous solution">Solubility in water</a></div> </td> <td>0.17 g / 100 mL </td></tr> <tr> <td><a href="/wiki/Solubility" title="Solubility">Solubility</a> </td> <td>very soluble in <a href="/wiki/Diethyl_ether" title="Diethyl ether">ether</a>, <a href="/wiki/Diethyl_ether" title="Diethyl ether">diethyl ether</a>, <a href="/wiki/Chloroform" title="Chloroform">chloroform</a>, <a href="/wiki/Oil" title="Oil">oil</a>, <a href="/wiki/Pyridine" title="Pyridine">pyridine</a> <br /> soluble in <a href="/wiki/Ethanol" title="Ethanol">ethanol</a> </td></tr> <tr> <td><a href="/wiki/Partition_coefficient" title="Partition coefficient">log <i>P</i></a> </td> <td>1.39 </td></tr> <tr> <td><a href="/wiki/Vapor_pressure" title="Vapor pressure">Vapor pressure</a> </td> <td>1.3 hPa (106 °C (223 °F)) </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Magnetic_susceptibility" title="Magnetic susceptibility">Magnetic susceptibility</a> (χ)</div> </td> <td><span class="nowrap"><span data-sort-value="3004175000000000000♠"></span>−82.5<span style="margin-left:0.25em;margin-right:0.15em;">×</span>10<sup>−6</sup> cm<sup>3</sup>/mol</span> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Structure </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Crystal_structure" title="Crystal structure">Crystal structure</a></div> </td> <td>orthorhombic </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Hazards </th></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;"><a href="/wiki/Globally_Harmonized_System_of_Classification_and_Labelling_of_Chemicals" title="Globally Harmonized System of Classification and Labelling of Chemicals"><b>GHS</b> labelling</a>: </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_hazard_pictograms" title="GHS hazard pictograms">Pictograms</a></div> </td> <td><span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-exclam.svg" class="mw-file-description" title="GHS07: Exclamation mark"><img alt="GHS07: Exclamation mark" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/50px-GHS-pictogram-exclam.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/75px-GHS-pictogram-exclam.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/100px-GHS-pictogram-exclam.svg.png 2x" data-file-width="512" data-file-height="512" /></a></span><span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-silhouette.svg" class="mw-file-description" title="GHS08: Health hazard"><img alt="GHS08: Health hazard" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/GHS-pictogram-silhouette.svg/50px-GHS-pictogram-silhouette.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/GHS-pictogram-silhouette.svg/75px-GHS-pictogram-silhouette.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/21/GHS-pictogram-silhouette.svg/100px-GHS-pictogram-silhouette.svg.png 2x" data-file-width="724" data-file-height="724" /></a></span> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Globally_Harmonized_System_of_Classification_and_Labelling_of_Chemicals#Signal_word" title="Globally Harmonized System of Classification and Labelling of Chemicals">Signal word</a></div> </td> <td><b>Warning</b> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_hazard_statements" title="GHS hazard statements">Hazard statements</a></div> </td> <td><abbr class="abbr" title="H302: Harmful if swallowed">H302</abbr>, <abbr class="abbr" title="H317: May cause an allergic skin reaction">H317</abbr>, <abbr class="abbr" title="H373: May cause damage to organs through prolonged or repeated exposure">H373</abbr> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_precautionary_statements" title="GHS precautionary statements">Precautionary statements</a></div> </td> <td><abbr class="abbr" title="P260: Do not breathe dust/fume/gas/mist/vapours/spray.">P260</abbr>, <abbr class="abbr" title="P261: Avoid breathing dust/fume/gas/mist/vapours/spray.">P261</abbr>, <abbr class="abbr" title="P264: Wash ... thoroughly after handling.">P264</abbr>, <abbr class="abbr" title="P270: Do not eat, drink or smoke when using this product.">P270</abbr>, <abbr class="abbr" title="P272: Contaminated work clothing should not be allowed out of the workplace.">P272</abbr>, <abbr class="abbr" title="P280: Wear protective gloves/protective clothing/eye protection/face protection.">P280</abbr>, <abbr class="abbr" title="P301+P312: IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell.">P301+P312</abbr>, <abbr class="abbr" title="P302+P352: IF ON SKIN: Wash with soap and water.">P302+P352</abbr>, <abbr class="abbr" title="P314: Get Medical advice/attention if you feel unwell.">P314</abbr>, <abbr class="abbr" title="P321: Specific treatment (see ... on this label).">P321</abbr>, <abbr class="abbr" title="P330: Rinse mouth.">P330</abbr>, <abbr class="abbr" title="P333+P313: If skin irritation or a rash occurs: Get medical advice/attention.">P333+P313</abbr>, <abbr class="abbr" title="P363: Wash contaminated clothing before reuse.">P363</abbr>, <abbr class="abbr" title="P501: Dispose of contents/container to ...">P501</abbr> </td></tr> <tr> <td><a href="/wiki/NFPA_704" title="NFPA 704"><b>NFPA 704</b></a> (fire diamond) </td> <td><style data-mw-deduplicate="TemplateStyles:r1170367383">.mw-parser-output .nfpa-704-diamond-ref{float:right;padding:1px;text-align:right}.mw-parser-output .nfpa-704-diamond-container{width:82px;font-family:sans-serif;margin:0 auto}.mw-parser-output .nfpa-704-diamond-container-ref{float:left;margin-left:1em}.mw-parser-output .nfpa-704-diamond-images{float:left;font-size:20px;text-align:center;position:relative;height:80px;width:80px;padding:1px}.mw-parser-output .nfpa-704-diamond-map{position:absolute;height:80px;width:80px}.mw-parser-output .nfpa-704-diamond .noresize{margin:0 auto}.mw-parser-output .nfpa-704-diamond-code{line-height:1em;text-align:center;position:absolute}.mw-parser-output .nfpa-704-diamond-code>a{color:black}.mw-parser-output .nfpa-704-diamond-blue{width:13px;top:31px;left:15px}.mw-parser-output .nfpa-704-diamond-red{width:12px;top:12px;left:35px}.mw-parser-output .nfpa-704-diamond-yellow{width:13px;top:31px;left:54px}.mw-parser-output .nfpa-704-diamond-white-image{position:relative;top:51px;left:0}.mw-parser-output .nfpa-704-diamond-white-text{vertical-align:middle;text-align:center;line-height:80%;position:absolute;top:52px}.mw-parser-output .nfpa-704-diamond-white-text a>span{position:absolute;color:black}.mw-parser-output .nfpa-704-diamond-white-wors{font-size:15px;width:23px;left:29px}.mw-parser-output .nfpa-704-diamond-white-wox{font-size:15px;font-stretch:condensed;width:21px;line-height:80%;top:-4px;left:29px}.mw-parser-output .nfpa-704-diamond-white-abcp{font-size:13.5px;font-stretch:condensed;width:28px;left:26px}.mw-parser-output .nfpa-704-diamond-white-ac{font-size:10px;width:30px;left:25px}.mw-parser-output .nfpa-704-diamond-white-strike{text-decoration:line-through}</style><div class="nfpa-704-diamond notheme"><div class="nfpa-704-diamond-container"><div class="nfpa-704-diamond-images nounderlines"> <div class="nfpa-704-diamond-map"><figure class="noresize" typeof="mw:File"><span><img alt="NFPA 704 four-colored diamond" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/80px-NFPA_704.svg.png" decoding="async" width="80" height="80" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/120px-NFPA_704.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/160px-NFPA_704.svg.png 2x" data-file-width="512" data-file-height="512" usemap="#ImageMap_482e25fdfe95519d" /></span><map name="ImageMap_482e25fdfe95519d"><area href="/wiki/NFPA_704#Blue" shape="poly" coords="23,23,47,47,23,70,0,47" alt="Health 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroform" title="Health 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroform" /><area href="/wiki/NFPA_704#Red" shape="poly" coords="47,0,70,23,47,47,23,23" alt="Flammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oil" title="Flammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oil" /><area href="/wiki/NFPA_704#Yellow" shape="poly" coords="70,23,94,47,70,70,47,47" alt="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" title="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" /><area href="/wiki/NFPA_704#White" shape="poly" coords="47,47,70,70,47,94,23,70" alt="Special hazards (white): no code" title="Special hazards (white): no code" /></map><figcaption></figcaption></figure></div><div class="nfpa-704-diamond-code nfpa-704-diamond-blue"> <a href="/wiki/NFPA_704#Blue" title="NFPA 704"><span title="Health 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroform" class="notheme mw-no-invert">2</span></a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-red"> <a href="/wiki/NFPA_704#Red" title="NFPA 704"><span title="Flammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oil" class="notheme mw-no-invert">1</span></a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-yellow"> <a href="/wiki/NFPA_704#Yellow" title="NFPA 704"><span title="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" class="notheme mw-no-invert">0</span></a></div></div></div></div> </td></tr> <tr> <td><a href="/wiki/Flash_point" title="Flash point">Flash point</a> </td> <td>150 °C (302 °F; 423 K) </td></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;"><b>Lethal dose</b> or concentration (LD, LC): </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">LD<sub>50</sub> (<a href="/wiki/Lethal_dose#LD50" title="Lethal dose">median dose</a>)</div> </td> <td>293 mg/kg (rat, oral) </td></tr> <tr> <td><a href="/wiki/Safety_data_sheet" title="Safety data sheet">Safety data sheet</a> (SDS) </td> <td><a rel="nofollow" class="external text" href="http://www.sigmaaldrich.com/MSDS/MSDS/DisplayMSDSPage.do?country=PL&language=EN-generic&productNumber=W504300&brand=ALDRICH&PageToGoToURL=http%3A%2F%2Fwww.sigmaaldrich.com%2Fcatalog%2Fproduct%2Faldrich%2Fw504300%3Flang%3Dpl">Sigma-Aldrich</a> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Related compounds </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Related compounds</div> </td> <td><a href="/wiki/Chromone" title="Chromone">Chromone</a>; <a href="/wiki/2-Cumaranone" title="2-Cumaranone">2-Cumaranone</a> </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"><div style="text-align:center;"><span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/12px-Yes_check.svg.png" decoding="async" width="12" height="12" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/18px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/24px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span> <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=443678400&page2=Coumarin">verify</a></span> (<a href="/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validation" title="Wikipedia:WikiProject Chemicals/Chembox validation">what is</a> <sup><span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup> ?) </div></div> <div style="margin-top: 0.3em; text-align: center;"><a href="/wiki/Wikipedia:Chemical_infobox#References" title="Wikipedia:Chemical infobox">Infobox references</a></div> </td></tr> </tbody></table><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound</div> <p><b>Coumarin</b> (<span class="rt-commentedText nowrap"><span class="IPA nopopups noexcerpt" lang="en-fonipa"><a href="/wiki/Help:IPA/English" title="Help:IPA/English">/<span style="border-bottom:1px dotted"><span title="/ˈ/: primary stress follows">ˈ</span><span title="'k' in 'kind'">k</span><span title="/uː/: 'oo' in 'goose'">uː</span><span title="'m' in 'my'">m</span><span title="/ər/: 'er' in 'letter'">ər</span><span title="/ɪ/: 'i' in 'kit'">ɪ</span><span title="'n' in 'nigh'">n</span></span>/</a></span></span>) or <b>2<i>H</i>-chromen-2-one</b> is an aromatic organic <a href="/wiki/Chemical_compound" title="Chemical compound">chemical compound</a> with formula <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<sub class="template-chem2-sub">9</sub>H<sub class="template-chem2-sub">6</sub>O<sub class="template-chem2-sub">2</sub></span>. Its molecule can be described as a <a href="/wiki/Benzene" title="Benzene">benzene</a> molecule with two adjacent <a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a> atoms replaced by an unsaturated <a href="/wiki/Lactone" title="Lactone">lactone</a> ring <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−(CH)=(CH)−(C=O)−O−</span>, forming a second six-membered <a href="/wiki/Heterocycle" class="mw-redirect" title="Heterocycle">heterocycle</a> that shares two <a href="/wiki/Carbon" title="Carbon">carbons</a> with the benzene ring. It belongs to the <a href="/wiki/Benzopyrone" title="Benzopyrone">benzopyrone</a> chemical class and considered as a lactone.<sup id="cite_ref-pubchem19_1-0" class="reference"><a href="#cite_note-pubchem19-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p><p>Coumarin is a colorless crystalline solid with a sweet <a href="/wiki/Odor" title="Odor">odor</a> resembling the scent of <a href="/wiki/Vanilla" title="Vanilla">vanilla</a> and a bitter taste.<sup id="cite_ref-pubchem19_1-1" class="reference"><a href="#cite_note-pubchem19-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> It is found in many plants, where it may serve as a <a href="/wiki/Plant_defense_against_herbivory" title="Plant defense against herbivory">chemical defense against predators</a>. Coumarin inhibits synthesis of <a href="/wiki/Vitamin_K" title="Vitamin K">vitamin K</a>, a key component in <a href="/wiki/Blood_clotting" class="mw-redirect" title="Blood clotting">blood clotting</a>. A related compound, the <a href="/wiki/Prescription_drug" title="Prescription drug">prescription drug</a> <a href="/wiki/Anticoagulant" title="Anticoagulant">anticoagulant</a> <a href="/wiki/Warfarin" title="Warfarin">warfarin</a>, is used to inhibit formation of <a href="/wiki/Blood_clot" class="mw-redirect" title="Blood clot">blood clots</a>, <a href="/wiki/Deep_vein_thrombosis" title="Deep vein thrombosis">deep vein thrombosis</a>, and <a href="/wiki/Pulmonary_embolism" title="Pulmonary embolism">pulmonary embolism</a>.<sup id="cite_ref-pubchem19_1-2" class="reference"><a href="#cite_note-pubchem19-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-drugs19_2-0" class="reference"><a href="#cite_note-drugs19-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Etymology">Etymology</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Coumarin&action=edit&section=1" title="Edit section: Etymology"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Coumarin is derived from <span title="French-language text"><i lang="fr">coumarou</i></span>, the French word for the <a href="/wiki/Tonka_bean" class="mw-redirect" title="Tonka bean">tonka bean</a>, from the <a href="/wiki/Tupi_language" title="Tupi language">Old Tupi</a> word for its tree, <span title="Tupi languages collective text"><i lang="tup">kumarú</i></span>.<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="History">History</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Coumarin&action=edit&section=2" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Coumarin was first isolated from <a href="/wiki/Tonka_beans" class="mw-redirect" title="Tonka beans">tonka beans</a> in 1820 by A. Vogel of Munich, who initially mistook it for <a href="/wiki/Benzoic_acid" title="Benzoic acid">benzoic acid</a>.<sup id="cite_ref-vogel1820a_4-0" class="reference"><a href="#cite_note-vogel1820a-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-vogel1820b_5-0" class="reference"><a href="#cite_note-vogel1820b-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p><p>Also in 1820, Nicholas Jean Baptiste Gaston Guibourt (1790–1867) of France independently isolated coumarin, but he realized that it was not benzoic acid.<sup id="cite_ref-guib1820_6-0" class="reference"><a href="#cite_note-guib1820-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> In a subsequent essay he presented to the pharmacy section of the <a href="/wiki/Acad%C3%A9mie_Royale_de_M%C3%A9decine" class="mw-redirect" title="Académie Royale de Médecine">Académie Royale de Médecine</a>, Guibourt named the new substance <i>coumarine</i>.<sup id="cite_ref-guib1825_7-0" class="reference"><a href="#cite_note-guib1825-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-guib1869_8-0" class="reference"><a href="#cite_note-guib1869-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p><p>In 1835, the French pharmacist A. Guillemette proved that Vogel and Guibourt had isolated the same substance.<sup id="cite_ref-guil1835_9-0" class="reference"><a href="#cite_note-guil1835-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> Coumarin was first synthesized in 1868 by the English chemist <a href="/wiki/William_Henry_Perkin" title="William Henry Perkin">William Henry Perkin</a>.<sup id="cite_ref-perkin1868_10-0" class="reference"><a href="#cite_note-perkin1868-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p><p>Coumarin has been an integral part of the <a href="/wiki/Foug%C3%A8re" title="Fougère">fougère</a> genre of perfume since it was first used in Houbigant's Fougère Royale in 1882.<sup id="cite_ref-fragrantica_11-0" class="reference"><a href="#cite_note-fragrantica-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Synthesis">Synthesis</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Coumarin&action=edit&section=3" title="Edit section: Synthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Coumarin can be prepared by a number of <a href="/wiki/Name_reaction" title="Name reaction">name reactions</a>, with the <a href="/wiki/Perkin_reaction" title="Perkin reaction">Perkin reaction</a> between <a href="/wiki/Salicylaldehyde" title="Salicylaldehyde">salicylaldehyde</a> and <a href="/wiki/Acetic_anhydride" title="Acetic anhydride">acetic anhydride</a> being a popular example. The <a href="/wiki/Pechmann_condensation" title="Pechmann condensation">Pechmann condensation</a> provides another route to coumarin and its derivatives starting from <a href="/wiki/Phenol" title="Phenol">phenol</a>, as does the <a href="/wiki/Kostanecki_acylation" title="Kostanecki acylation">Kostanecki acylation</a>,<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> which can also be used to produce <a href="/wiki/Chromones" class="mw-redirect" title="Chromones">chromones</a>. </p> <div class="mw-heading mw-heading2"><h2 id="Biosynthesis">Biosynthesis</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Coumarin&action=edit&section=4" title="Edit section: Biosynthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>From <a href="/wiki/Lactonization" class="mw-redirect" title="Lactonization">lactonization</a> of <i>ortho</i>-hydroxylated <i>cis</i>-<a href="/wiki/Hydroxycinnamic_acid" title="Hydroxycinnamic acid">hydroxycinnamic acid</a>.<sup id="cite_ref-Jacobowitz-Weng-2020_13-0" class="reference"><a href="#cite_note-Jacobowitz-Weng-2020-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Natural_occurrence">Natural occurrence</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Coumarin&action=edit&section=5" title="Edit section: Natural occurrence"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Coumarin is found naturally in many plants. Freshly ground plant parts contain higher amount of desired and undesired phytochemicals than powder. In addition, whole plant parts are harder to counterfeit; for example, one study showed that authentic <a href="/wiki/Ceylon_cinnamon" class="mw-redirect" title="Ceylon cinnamon">Ceylon cinnamon</a> bark contained 0.012 to 0.143 mg/g coumarin, but samples purchased at markets contained up to 3.462 mg/g, possibly because those were mixed with other cinnamon varieties.<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> <ul><li>Vanilla grass (<i><a href="/wiki/Anthoxanthum_odoratum" title="Anthoxanthum odoratum">Anthoxanthum odoratum</a></i>)</li> <li>Sweet woodruff (<i><a href="/wiki/Galium_odoratum" title="Galium odoratum">Galium odoratum</a></i>)</li> <li>Sweet grass (<i><a href="/wiki/Hierochloe_odorata" title="Hierochloe odorata">Hierochloe odorata</a></i>)</li> <li>Sweet-clover (genus <i><a href="/wiki/Melilotus" title="Melilotus">Melilotus</a></i>)</li> <li>Meranti trees (genus <i><a href="/wiki/Shorea" title="Shorea">Shorea</a></i>)</li> <li><a href="/wiki/Dipteryx_odorata" title="Dipteryx odorata">Tonka bean</a> (<i>Dipteryx odorata</i>)</li> <li><a href="/wiki/Cinnamon" title="Cinnamon">Cinnamon</a>; a 2013 study showed different varieties containing different levels of coumarin:<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> <ul><li>Ceylon cinnamon or true cinnamon (<i><a href="/wiki/Cinnamomum_verum" title="Cinnamomum verum">Cinnamomum verum</a></i>): 0.005 to 0.090 mg/g</li> <li>Chinese cinnamon or Chinese cassia (<i><a href="/wiki/Cinnamomum_cassia" title="Cinnamomum cassia">C. cassia</a></i>): 0.085 to 0.310 mg/g</li> <li>Indonesian cinnamon or Padang cassia (<i><a href="/wiki/Cinnamomum_burmannii" class="mw-redirect" title="Cinnamomum burmannii">C. burmannii</a></i>): 2.14 to 9.30 mg/g</li> <li><a href="/wiki/Saigon_cinnamon" title="Saigon cinnamon">Saigon cinnamon</a> or Vietnamese cassia (<i>C. loureiroi</i>): 1.06 to 6.97 mg/g</li></ul></li> <li>Deertongue (<i><a href="/wiki/Carphephorus_odoratissimus" title="Carphephorus odoratissimus">Carphephorus odoratissimus</a></i>),<sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup></li> <li>Tilo (<i><a href="/wiki/Justicia_pectoralis" class="mw-redirect" title="Justicia pectoralis">Justicia pectoralis</a></i>),<sup id="cite_ref-leal2010_17-0" class="reference"><a href="#cite_note-leal2010-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-lino1997_18-0" class="reference"><a href="#cite_note-lino1997-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup></li> <li>Mullein (genus <i><a href="/wiki/Verbascum" title="Verbascum">Verbascum</a></i>)</li> <li>Many <a href="/wiki/Cherry_blossom" title="Cherry blossom">cherry blossom</a> tree varieties (of the genus <i><a href="/wiki/Prunus" title="Prunus">Prunus</a></i>).<sup id="cite_ref-ieri2012_19-0" class="reference"><a href="#cite_note-ieri2012-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup></li> <li>Related compounds are found in some but not all specimens of genus <i><a href="/wiki/Glycyrrhiza" title="Glycyrrhiza">Glycyrrhiza</a></i>, from which the root and flavour <a href="/wiki/Licorice" class="mw-redirect" title="Licorice">licorice</a> derives.<sup id="cite_ref-hata2018_20-0" class="reference"><a href="#cite_note-hata2018-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup></li></ul> <p>Coumarin is found naturally also in many edible plants such as <a href="/wiki/Strawberries" class="mw-redirect" title="Strawberries">strawberries</a>, <a href="/wiki/Black_currant" class="mw-redirect" title="Black currant">black currants</a>, <a href="/wiki/Apricot" title="Apricot">apricots</a>, and <a href="/wiki/Cherries" class="mw-redirect" title="Cherries">cherries</a>.<sup id="cite_ref-pubchem19_1-3" class="reference"><a href="#cite_note-pubchem19-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p><p>Coumarins were found to be uncommon but occasional components of <a href="/wiki/Propolis" title="Propolis">propolis</a> by Santos-Buelga and Gonzalez-Paramas 2017.<sup id="cite_ref-Berenbaum-Calla-2021_21-0" class="reference"><a href="#cite_note-Berenbaum-Calla-2021-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Biological_function">Biological function</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Coumarin&action=edit&section=6" title="Edit section: Biological function"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Coumarin has appetite-suppressing properties, which may discourage animals from eating plants that contain it. Though the compound has a pleasant sweet odor, it has a bitter taste, and animals tend to avoid it.<sup id="cite_ref-link1959_22-0" class="reference"><a href="#cite_note-link1959-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Metabolism">Metabolism</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Coumarin&action=edit&section=7" title="Edit section: Metabolism"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The <a href="/wiki/Biosynthesis" title="Biosynthesis">biosynthesis</a> of coumarin in plants is via <a href="/wiki/Hydroxylation" title="Hydroxylation">hydroxylation</a>, <a href="/wiki/Glycolysis" title="Glycolysis">glycolysis</a>, and <a href="/wiki/Cyclization" class="mw-redirect" title="Cyclization">cyclization</a> of <a href="/wiki/Cinnamic_acid" title="Cinnamic acid">cinnamic acid</a>.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (December 2018)">citation needed</span></a></i>]</sup> In humans, the enzyme encoded by the gene <i><a href="/wiki/UGT1A8" title="UGT1A8">UGT1A8</a></i> has <a href="https://en.wiktionary.org/wiki/glucuronidase" class="extiw" title="wikt:glucuronidase">glucuronidase</a> activity with many substrates, including coumarins.<sup id="cite_ref-ritter1992_23-0" class="reference"><a href="#cite_note-ritter1992-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Derivatives">Derivatives</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Coumarin&action=edit&section=8" title="Edit section: Derivatives"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main articles: <a href="/wiki/4-Hydroxycoumarins" title="4-Hydroxycoumarins">4-Hydroxycoumarins</a> and <a href="/wiki/Coumarin_derivatives" title="Coumarin derivatives">Coumarin derivatives</a></div> <p>Coumarin is used in the pharmaceutical industry as a precursor reagent in the synthesis of a number of synthetic anticoagulant pharmaceuticals similar to <a href="/wiki/Dicoumarol" title="Dicoumarol">dicoumarol</a>.<sup id="cite_ref-pubchem19_1-4" class="reference"><a href="#cite_note-pubchem19-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> <a href="/wiki/4-hydroxycoumarins" class="mw-redirect" title="4-hydroxycoumarins">4-hydroxycoumarins</a> are a type of <a href="/wiki/Vitamin_K_antagonist" title="Vitamin K antagonist">vitamin K antagonist</a>.<sup id="cite_ref-pubchem19_1-5" class="reference"><a href="#cite_note-pubchem19-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> They block the regeneration and recycling of <a href="/wiki/Vitamin_K" title="Vitamin K">vitamin K</a>.<sup id="cite_ref-pubchem19_1-6" class="reference"><a href="#cite_note-pubchem19-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-warfarin_24-0" class="reference"><a href="#cite_note-warfarin-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> These chemicals are sometimes also incorrectly referred to as "coumadins" rather than 4-hydroxycoumarins. Some of the 4-hydroxycoumarin anticoagulant class of chemicals are designed to have high potency and long residence times in the body, and these are used specifically as <a href="/wiki/Rodenticide" title="Rodenticide">rodenticides</a> ("rat poison").<sup id="cite_ref-pubchem19_1-7" class="reference"><a href="#cite_note-pubchem19-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Death occurs after a period of several days to two weeks, usually from internal hemorrhaging. </p> <div class="mw-heading mw-heading2"><h2 id="Uses">Uses</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Coumarin&action=edit&section=9" title="Edit section: Uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Coumarin is often found in <a href="/wiki/Artificial_vanilla" class="mw-redirect" title="Artificial vanilla">artificial vanilla</a> substitutes, despite having been banned as a food additive in numerous countries since the mid-20th century. It is still used as a legal flavorant in soaps, rubber products, and the tobacco industry,<sup id="cite_ref-pubchem19_1-8" class="reference"><a href="#cite_note-pubchem19-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> particularly for sweet <a href="/wiki/Pipe_tobacco" class="mw-redirect" title="Pipe tobacco">pipe tobacco</a> and certain alcoholic drinks.<sup class="noprint Inline-Template" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Avoid_weasel_words" class="mw-redirect" title="Wikipedia:Avoid weasel words"><span title="The material near this tag possibly uses too vague attribution or weasel words. (February 2024)">which?</span></a></i>]</sup><sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (February 2024)">citation needed</span></a></i>]</sup> </p> <div class="mw-heading mw-heading2"><h2 id="Toxicity">Toxicity</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Coumarin&action=edit&section=10" title="Edit section: Toxicity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Coumarin is moderately <a href="/wiki/Hepatotoxicity" title="Hepatotoxicity">toxic to the liver</a> and <a href="/wiki/Renal_toxicity" class="mw-redirect" title="Renal toxicity">kidneys</a> of rodents, with a <a href="/wiki/Median_lethal_dose" title="Median lethal dose">median lethal dose</a> (LD<sub>50</sub>) of 293 mg/kg in the rat,<sup id="cite_ref-25" class="reference"><a href="#cite_note-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> a low toxicity compared to related compounds. Coumarin is hepatotoxic in rats, but less so in mice. Rodents metabolize it mostly to 3,4-coumarin <a href="/wiki/Epoxide" title="Epoxide">epoxide</a>, a toxic, unstable compound that on further differential metabolism may cause liver cancer in rats and lung tumors in mice.<sup id="cite_ref-vassa2004_26-0" class="reference"><a href="#cite_note-vassa2004-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-born203_27-0" class="reference"><a href="#cite_note-born203-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> Humans metabolize it mainly to <a href="/wiki/7-hydroxycoumarin" class="mw-redirect" title="7-hydroxycoumarin">7-hydroxycoumarin</a>, a compound of lower toxicity, and no adverse affect has been directly measured in humans.<sup id="cite_ref-28" class="reference"><a href="#cite_note-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> The German Federal Institute for Risk Assessment has established a tolerable daily intake (TDI) of 0.1 mg coumarin per kg body weight, but also advises that higher intake for a short time is not dangerous.<sup id="cite_ref-bfrtdi_29-0" class="reference"><a href="#cite_note-bfrtdi-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> The <a href="/wiki/Occupational_Safety_and_Health_Administration" title="Occupational Safety and Health Administration">Occupational Safety and Health Administration</a> (OSHA) of the United States does not classify coumarin as a <a href="/wiki/Carcinogen" title="Carcinogen">carcinogen</a> for humans.<sup id="cite_ref-osha2015_30-0" class="reference"><a href="#cite_note-osha2015-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> </p><p>European health agencies have warned against consuming high amounts of <a href="/wiki/Cassia_bark" class="mw-redirect" title="Cassia bark">cassia bark</a>, one of the four main species of <a href="/wiki/Cinnamon" title="Cinnamon">cinnamon</a>, because of its coumarin content.<sup id="cite_ref-bund2015_31-0" class="reference"><a href="#cite_note-bund2015-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-npr2015_32-0" class="reference"><a href="#cite_note-npr2015-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> According to the German <a href="/wiki/Federal_Institute_for_Risk_Assessment" title="Federal Institute for Risk Assessment">Federal Institute for Risk Assessment</a> (BFR), 1 kg of (cassia) cinnamon powder contains about 2.1 to 4.4 g of coumarin.<sup id="cite_ref-bund2006_33-0" class="reference"><a href="#cite_note-bund2006-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> Powdered cassia cinnamon weighs 0.56 g/cm<sup>3</sup>,<sup id="cite_ref-powd2002_34-0" class="reference"><a href="#cite_note-powd2002-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> so a kilogram of cassia cinnamon powder equals 362.29 teaspoons. One teaspoon of cassia cinnamon powder therefore contains 5.8 to 12.1 mg of coumarin, which may be above the tolerable daily intake value for smaller individuals.<sup id="cite_ref-bund2006_33-1" class="reference"><a href="#cite_note-bund2006-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> However, the BFR only cautions against high daily intake of foods containing coumarin. Its report specifically states that Ceylon cinnamon (<i><a href="/wiki/Cinnamomum_verum" title="Cinnamomum verum">Cinnamomum verum</a></i>) contains "hardly any" coumarin.<sup id="cite_ref-bund2006_33-2" class="reference"><a href="#cite_note-bund2006-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> </p><p>The European Regulation (EC) No 1334/2008 describes the following maximum limits for coumarin: 50 mg/kg in traditional and/or seasonal bakery ware containing a reference to cinnamon in the labeling, 20 mg/kg in breakfast cereals including <a href="/wiki/Muesli" title="Muesli">muesli</a>, 15 mg/kg in fine bakery ware, with the exception of traditional and/or seasonal bakery ware containing a reference to cinnamon in the labeling, and 5 mg/kg in desserts. </p><p>An investigation from the Danish Veterinary and Food Administration in 2013 shows that bakery goods characterized as fine bakery ware exceeds the European limit (15 mg/kg) in almost 50% of the cases.<sup id="cite_ref-ball2014_35-0" class="reference"><a href="#cite_note-ball2014-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> The paper also mentions tea as an additional important contributor to the overall coumarin intake, especially for children with a sweet habit. </p><p>Coumarin was banned as a food additive in the United States in 1954, largely because of the hepatotoxicity results in rodents.<sup id="cite_ref-marles1986_36-0" class="reference"><a href="#cite_note-marles1986-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup> Coumarin is currently listed by the <a href="/wiki/Food_and_Drug_Administration" title="Food and Drug Administration">Food and Drug Administration</a> (FDA) of the United States among "Substances Generally Prohibited From Direct Addition or Use as Human Food," according to 21 <a href="/wiki/Code_of_Federal_Regulations" title="Code of Federal Regulations">CFR</a> 189.130,<sup id="cite_ref-fodru2015_37-0" class="reference"><a href="#cite_note-fodru2015-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-eafus_38-0" class="reference"><a href="#cite_note-eafus-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup> but some natural additives containing coumarin, such as the <a href="/wiki/Flavoring" title="Flavoring">flavorant</a> <a href="/wiki/Galium_odoratum" title="Galium odoratum">sweet woodruff</a> are allowed "in alcoholic beverages only" under 21 <a href="/wiki/Code_of_Federal_Regulations" title="Code of Federal Regulations">CFR</a> 172.510.<sup id="cite_ref-fodu2015b_39-0" class="reference"><a href="#cite_note-fodu2015b-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup> In Europe, popular examples of such beverages are <i><a href="/wiki/Maiwein" class="mw-redirect" title="Maiwein">Maiwein</a>,</i> white wine with woodruff, and <i><a href="/wiki/%C5%BBubr%C3%B3wka" title="Żubrówka">Żubrówka</a>,</i> vodka flavoured with <a href="/wiki/Hierochloe_odorata" title="Hierochloe odorata">bison grass</a>. </p><p>Coumarin is subject to restrictions on its use in perfumery,<sup id="cite_ref-ifraorg_40-0" class="reference"><a href="#cite_note-ifraorg-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup> as some people may become sensitized to it, however the evidence that coumarin can cause an allergic reaction in humans is disputed.<sup id="cite_ref-crowat_41-0" class="reference"><a href="#cite_note-crowat-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> </p><p>Minor neurological dysfunction was found in children exposed to the anticoagulants <a href="/wiki/Acenocoumarol" title="Acenocoumarol">acenocoumarol</a> or <a href="/wiki/Phenprocoumon" title="Phenprocoumon">phenprocoumon</a> during pregnancy. A group of 306 children were tested at ages 7–15 years to determine subtle neurological effects from anticoagulant exposure. Results showed a <a href="/wiki/Dose%E2%80%93response_relationship" title="Dose–response relationship">dose–response relationship</a> between anticoagulant exposure and minor neurological dysfunction. Overall, a 1.9 (90%) increase in minor neurological dysfunction was observed for children exposed to these anticoagulants, which are collectively referred to as "coumarins." In conclusion, researchers stated, "The results suggest that coumarins have an influence on the development of the brain which can lead to mild neurologic dysfunctions in children of school age."<sup id="cite_ref-wess2001_42-0" class="reference"><a href="#cite_note-wess2001-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup> </p><p>Coumarin's addition to <a href="/wiki/Cigarette" title="Cigarette">cigarette</a> tobacco by <a href="/wiki/Brown_%26_Williamson" title="Brown & Williamson">Brown & Williamson</a> caused executive<sup id="cite_ref-60minutes_43-0" class="reference"><a href="#cite_note-60minutes-43"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup> Dr. <a href="/wiki/Jeffrey_Wigand" title="Jeffrey Wigand">Jeffrey Wigand</a> to contact <a href="/wiki/CBS" title="CBS">CBS</a>'s news show <i><a href="/wiki/60_Minutes" title="60 Minutes">60 Minutes</a></i> in 1995, charging that a "form of <a href="/wiki/Rat_poison" class="mw-redirect" title="Rat poison">rat poison</a>" was being used as an additive. He held that from a chemist’s point of view, coumarin is an "immediate precursor" to the rodenticide (and prescription drug) <a href="/wiki/Coumadin" class="mw-redirect" title="Coumadin">coumadin</a>.<sup id="cite_ref-drugs19_2-1" class="reference"><a href="#cite_note-drugs19-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> Dr. Wigand later stated that coumarin itself is dangerous, pointing out that the <a href="/wiki/Food_and_Drug_Administration" title="Food and Drug Administration">FDA</a> had banned its addition to human food in 1954.<sup id="cite_ref-tobtri_44-0" class="reference"><a href="#cite_note-tobtri-44"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup> Under his later testimony, he would repeatedly classify coumarin as a "lung-specific carcinogen."<sup id="cite_ref-indoc_45-0" class="reference"><a href="#cite_note-indoc-45"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup> In Germany, coumarin is banned as an additive in tobacco. </p><p>Alcoholic beverages sold in the <a href="/wiki/European_Union" title="European Union">European Union</a> are limited to a maximum of 10 mg/L coumarin by law.<sup id="cite_ref-thieme_46-0" class="reference"><a href="#cite_note-thieme-46"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup> Cinnamon flavor is generally cassia bark steam-distilled to concentrate the cinnamaldehyde, for example, to about 93%. Clear cinnamon-flavored alcoholic beverages generally test negative for coumarin, but if whole cassia bark is used to make <a href="/wiki/Mulled_wine" title="Mulled wine">mulled wine</a>, then coumarin shows up at significant levels.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (February 2024)">citation needed</span></a></i>]</sup> </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=Coumarin&action=edit&section=11" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-pubchem19-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-pubchem19_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-pubchem19_1-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-pubchem19_1-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-pubchem19_1-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-pubchem19_1-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-pubchem19_1-5"><sup><i><b>f</b></i></sup></a> <a href="#cite_ref-pubchem19_1-6"><sup><i><b>g</b></i></sup></a> <a href="#cite_ref-pubchem19_1-7"><sup><i><b>h</b></i></sup></a> <a href="#cite_ref-pubchem19_1-8"><sup><i><b>i</b></i></sup></a></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/323">"Coumarin"</a>. 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Retrieved <span class="nowrap">13 April</span> 2019</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Coumarin&rft.pub=PubChem%2C+National+Library+of+Medicine%2C+US+National+Institutes+of+Health&rft.date=2019-04-04&rft_id=https%3A%2F%2Fpubchem.ncbi.nlm.nih.gov%2Fcompound%2F323&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACoumarin" class="Z3988"></span></span> </li> <li id="cite_note-drugs19-2"><span class="mw-cite-backlink">^ <a href="#cite_ref-drugs19_2-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-drugs19_2-1"><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.drugs.com/drug-class/coumarins-and-indandiones.html">"Coumarins and indandiones"</a>. Drugs.com. 2016<span class="reference-accessdate">. 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Retrieved <span class="nowrap">2023-12-20</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=www.chm.bris.ac.uk&rft.atitle=Warfarin%2C+Molecule+of+the+Month+for+February+2011%2C+by+John+Maher&rft_id=https%3A%2F%2Fwww.chm.bris.ac.uk%2Fmotm%2Fwarfarin%2F&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACoumarin" class="Z3988"></span></span> </li> <li id="cite_note-vogel1820a-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-vogel1820a_4-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFVogel1820" class="citation journal cs1 cs1-prop-foreign-lang-source">Vogel, A. 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(1820). <a rel="nofollow" class="external text" href="http://gallica.bnf.fr/ark:/12148/bpt6k78140v/f311.image">"De l'existence de l'acide benzoïque dans la fève de tonka et dans les fleurs de mélilot"</a> [On the existence of benzoic acid in the tonka bean and in the flowers of melilot]. <i>Journal de Pharmacie</i> (in French). <b>6</b>: 305–309.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+de+Pharmacie&rft.atitle=De+l%27existence+de+l%27acide+benzo%C3%AFque+dans+la+f%C3%A8ve+de+tonka+et+dans+les+fleurs+de+m%C3%A9lilot&rft.volume=6&rft.pages=305-309&rft.date=1820&rft.aulast=Vogel&rft.aufirst=A.&rft_id=http%3A%2F%2Fgallica.bnf.fr%2Fark%3A%2F12148%2Fbpt6k78140v%2Ff311.image&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACoumarin" class="Z3988"></span></span> </li> <li id="cite_note-guib1820-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-guib1820_6-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGuibourt1820" class="citation book cs1 cs1-prop-foreign-lang-source">Guibourt, N. 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[... more recently, in an essay on chemical nomenclature, [which was] read to the pharmacy section of the Royal Academy of Medicine, he [Guibourt] designated it by the name "coumarine," derived from the name of the vegetable <i>Coumarouna odorata</i> ...]</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+de+Chimie+M%C3%A9dicale%2C+de+Pharmacie+et+de+Toxicologie&rft.atitle=Societe+du+Pharmacie+de+Paris&rft.volume=1&rft.pages=303&rft.date=1825&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DL_IwAAAAYAAJ%26pg%3DPA303&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACoumarin" class="Z3988"></span></span> </li> <li id="cite_note-guib1869-8"><span class="mw-cite-backlink"><b><a href="#cite_ref-guib1869_8-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGuibourt1869" class="citation book cs1">Guibourt, N. J. B. G. 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Retrieved <span class="nowrap">2 December</span> 2018</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Legacy.library.ucsf.edu&rft.atitle=Industry+Documents+Library&rft_id=http%3A%2F%2Flegacy.library.ucsf.edu%2Ftid%2Ftnt32e00&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACoumarin" class="Z3988"></span></span> </li> <li id="cite_note-thieme-46"><span class="mw-cite-backlink"><b><a href="#cite_ref-thieme_46-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWangAvulaZhaoSmillie2010" class="citation journal cs1">Wang, YH; Avula, B.; Zhao, J.; Smillie, TJ; Nanayakkara, NPD; Khan, IA (2010). "Characterization and Distribution of Coumarin, Cinnamaldehyde and Related Compounds in Cinnamomum spp. by UPLC-UV/MS Combined with PCA". <i>Planta Medica</i>. <b>76</b> (5). <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1055%2Fs-0030-1251793">10.1055/s-0030-1251793</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Planta+Medica&rft.atitle=Characterization+and+Distribution+of+Coumarin%2C+Cinnamaldehyde+and+Related+Compounds+in+Cinnamomum+spp.+by+UPLC-UV%2FMS+Combined+with+PCA&rft.volume=76&rft.issue=5&rft.date=2010&rft_id=info%3Adoi%2F10.1055%2Fs-0030-1251793&rft.aulast=Wang&rft.aufirst=YH&rft.au=Avula%2C+B.&rft.au=Zhao%2C+J.&rft.au=Smillie%2C+TJ&rft.au=Nanayakkara%2C+NPD&rft.au=Khan%2C+IA&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACoumarin" class="Z3988"></span></span> </li> </ol></div> <div 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class="navbox-group" style="width:1%">Classes of <a href="/wiki/Phenylpropanoid" title="Phenylpropanoid">phenylpropanoids</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Hydroxycinnamic_acid" title="Hydroxycinnamic acid">Hydroxycinnamic acids</a></li> <li><a href="/wiki/Chromone" title="Chromone">Chromones</a> (<a href="/wiki/Furanochromone" title="Furanochromone">Furanochromones</a>)</li> <li><a href="/wiki/Cinnamaldehyde" title="Cinnamaldehyde">Cinnamaldehydes</a></li> <li><a href="/wiki/Monolignol" title="Monolignol">Monolignols</a></li> <li><a class="mw-selflink selflink">Coumarins</a></li> <li><a href="/wiki/Chalcone" title="Chalcone">Chalcones</a></li> <li><a href="/wiki/Flavonoid" title="Flavonoid">Flavonoids</a></li> <li><a href="/wiki/Allylbenzenes" class="mw-redirect" title="Allylbenzenes">Allylbenzenes</a></li> <li><a href="/wiki/Stilbenoid" title="Stilbenoid">Stilbenoids</a></li> <li><a href="/wiki/Lignan" title="Lignan">Lignans</a></li> <li><a href="/wiki/Lignin" title="Lignin">Lignins</a></li> <li><a href="/wiki/Suberin" title="Suberin">Suberins</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Examples</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Rhododendrin" title="Rhododendrin">Rhododendrin</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Types_of_coumarins" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Coumarin" title="Template:Coumarin"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Coumarin" title="Template talk:Coumarin"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Coumarin" title="Special:EditPage/Template:Coumarin"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Types_of_coumarins" style="font-size:114%;margin:0 4em">Types of <a class="mw-selflink selflink">coumarins</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Aglycone" title="Aglycone">Aglycones</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Aesculetin" title="Aesculetin">Aesculetin</a></li> <li><a href="/wiki/Ferujol" title="Ferujol">Ferujol</a></li> <li><a href="/wiki/Umbelliferone" title="Umbelliferone">Umbelliferone</a></li></ul> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="O-Methylated" scope="row" class="navbox-group" style="width:1%">O-Methylated</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Fraxetin" title="Fraxetin">Fraxetin</a></li> <li><a href="/wiki/Herniarin" title="Herniarin">Herniarin</a></li> <li><a href="/wiki/Osthol" title="Osthol">Osthol</a></li> <li><a href="/wiki/Scopoletin" title="Scopoletin">Scopoletin</a></li></ul> </div></td></tr></tbody></table><div> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Glycoside" title="Glycoside">Glycosides</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Aesculin" title="Aesculin">Aesculin</a></li> <li><a href="/wiki/Fraxin" title="Fraxin">Fraxin</a></li> <li><a href="/wiki/Skimmin" title="Skimmin">Skimmin</a></li> <li><a href="/wiki/Scopolin" title="Scopolin">Scopolin</a></li> <li><a href="/w/index.php?title=Umbelliferone_7-apiosylglucoside&action=edit&redlink=1" class="new" title="Umbelliferone 7-apiosylglucoside (page does not exist)">Umbelliferone 7-apiosylglucoside</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Derivatives</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Furanocoumarins" scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Furanocoumarin" title="Furanocoumarin">Furanocoumarins</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">Aglycones</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Angelicin" title="Angelicin">Angelicin</a></li> <li><a href="/wiki/Marmesin" title="Marmesin">Marmesin</a></li> <li><a href="/wiki/Psoralen" title="Psoralen">Psoralen</a></li> <li><a href="/wiki/Vaginol" title="Vaginol">Vaginol</a></li> <li><a href="/wiki/Xanthotoxol" title="Xanthotoxol">Xanthotoxol</a></li></ul> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="O-Methylated" scope="row" class="navbox-group" style="width:1%">O-Methylated</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Bergapten" title="Bergapten">Bergapten</a></li> <li><a href="/wiki/Isopimpinellin" title="Isopimpinellin">Isopimpinellin</a></li> <li><a href="/wiki/Methoxsalen" title="Methoxsalen">Methoxsalen</a></li> <li><a href="/wiki/Trioxsalen" title="Trioxsalen">Trioxsalen</a></li></ul> </div></td></tr></tbody></table><div> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Furanocoumarin glycosides</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Apterin" title="Apterin">Apterin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Meroterpene furanocoumarin ether</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Auraptene" title="Auraptene">Auraptene</a></li> <li><a href="/wiki/Bergamottin" title="Bergamottin">Bergamottin</a></li> <li><a href="/wiki/Imperatorin" title="Imperatorin">Imperatorin</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Oligomers</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Dicoumarol" title="Dicoumarol">Dicoumarol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Synthetic</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acenocoumarol" title="Acenocoumarol">Acenocoumarol</a></li> <li><a href="/wiki/Coumatetralyl" title="Coumatetralyl">Coumatetralyl</a></li> <li><a href="/wiki/Ensaculin" title="Ensaculin">Ensaculin</a></li> <li><a href="/wiki/Ethyl_biscoumacetate" title="Ethyl biscoumacetate">Ethyl biscoumacetate</a></li> <li><a href="/wiki/4-Hydroxycoumarins" title="4-Hydroxycoumarins">4-Hydroxycoumarins</a></li> <li><a href="/wiki/Hymecromone" title="Hymecromone">Hymecromone</a></li> <li><a href="/wiki/Phenprocoumon" title="Phenprocoumon">Phenprocoumon</a></li> <li><a href="/wiki/Warfarin" title="Warfarin">Warfarin</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox authority-control" aria-label="Navbox" style="padding:3px"><table class="nowraplinks hlist navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Help:Authority_control" 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