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class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>Uses</span> </div> </a> <button aria-controls="toc-Uses-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 Uses subsection</span> </button> <ul id="toc-Uses-sublist" class="vector-toc-list"> <li id="toc-Flavoring" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Flavoring"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.1</span> <span>Flavoring</span> </div> </a> <ul id="toc-Flavoring-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Precursor_to_other_compounds" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Precursor_to_other_compounds"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.2</span> <span>Precursor to other compounds</span> </div> </a> <ul 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id="toc-Antimicrobial_and_antifungal_activity-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Insecticidal_activity" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Insecticidal_activity"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.2</span> <span>Insecticidal activity</span> </div> </a> <ul id="toc-Insecticidal_activity-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Ouzo_effect" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Ouzo_effect"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.3</span> <span>Ouzo effect</span> </div> </a> <ul id="toc-Ouzo_effect-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Precursor_to_illicit_drugs" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Precursor_to_illicit_drugs"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.4</span> <span>Precursor to illicit drugs</span> </div> </a> <ul id="toc-Precursor_to_illicit_drugs-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Estrogen_and_prolactin" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Estrogen_and_prolactin"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.5</span> <span>Estrogen and prolactin</span> </div> </a> <ul id="toc-Estrogen_and_prolactin-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Safety" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Safety"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Safety</span> </div> </a> <ul id="toc-Safety-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-History" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#History"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>History</span> </div> </a> <ul id="toc-History-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>See also</span> </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>External links</span> </div> </a> <ul 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Available in 27 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-27" 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">27 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/%D8%A3%D9%86%D9%8A%D8%AB%D9%88%D9%84" title="أنيثول – Arabic" lang="ar" hreflang="ar" data-title="أنيثول" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Anetol" title="Anetol – Catalan" lang="ca" hreflang="ca" data-title="Anetol" 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/Anetol" title="Anetol – Czech" lang="cs" hreflang="cs" data-title="Anetol" 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/Anethol" title="Anethol – Danish" lang="da" hreflang="da" data-title="Anethol" 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/Anethol" title="Anethol – German" lang="de" hreflang="de" data-title="Anethol" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%91%CE%BD%CE%B7%CE%B8%CF%8C%CE%BB%CE%B7" title="Ανηθόλη – Greek" lang="el" hreflang="el" data-title="Ανηθόλη" 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/Anetol" title="Anetol – Spanish" lang="es" hreflang="es" data-title="Anetol" 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/Anetolo" title="Anetolo – Esperanto" lang="eo" hreflang="eo" data-title="Anetolo" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/An%C3%A9thol" title="Anéthol – French" lang="fr" hreflang="fr" data-title="Anéthol" 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%95%84%EB%84%A4%ED%86%A8" title="아네톨 – Korean" lang="ko" hreflang="ko" data-title="아네톨" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Anetol" title="Anetol – Indonesian" lang="id" hreflang="id" data-title="Anetol" 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/Anetolo" title="Anetolo – Italian" lang="it" hreflang="it" data-title="Anetolo" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Anethol" title="Anethol – Dutch" lang="nl" hreflang="nl" data-title="Anethol" 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%A2%E3%83%8D%E3%83%88%E3%83%BC%E3%83%AB" title="アネトール – Japanese" lang="ja" hreflang="ja" data-title="アネトール" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Anetol" title="Anetol – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Anetol" 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-oc mw-list-item"><a href="https://oc.wikipedia.org/wiki/Anet%C3%B2l" title="Anetòl – Occitan" lang="oc" hreflang="oc" data-title="Anetòl" data-language-autonym="Occitan" data-language-local-name="Occitan" class="interlanguage-link-target"><span>Occitan</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Anetol" title="Anetol – Polish" lang="pl" hreflang="pl" data-title="Anetol" 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/Anetol" title="Anetol – Portuguese" lang="pt" hreflang="pt" data-title="Anetol" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%90%D0%BD%D0%B5%D1%82%D0%BE%D0%BB" title="Анетол – Russian" lang="ru" hreflang="ru" data-title="Анетол" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Anetol" title="Anetol – Serbian" lang="sr" hreflang="sr" data-title="Anetol" 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/Anetol" title="Anetol – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Anetol" 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/Anetoli" title="Anetoli – Finnish" lang="fi" hreflang="fi" data-title="Anetoli" 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/Anetol" title="Anetol – Swedish" lang="sv" hreflang="sv" data-title="Anetol" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%90%D0%BD%D0%B5%D1%82%D0%BE%D0%BB" title="Анетол – Ukrainian" lang="uk" hreflang="uk" data-title="Анетол" 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/Anethol" title="Anethol – Vietnamese" lang="vi" hreflang="vi" data-title="Anethol" 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-wuu mw-list-item"><a href="https://wuu.wikipedia.org/wiki/%E8%8C%B4%E9%A6%99%E8%84%91" title="茴香脑 – Wu" lang="wuu" hreflang="wuu" data-title="茴香脑" data-language-autonym="吴语" data-language-local-name="Wu" class="interlanguage-link-target"><span>吴语</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E8%8C%B4%E9%A6%99%E8%84%91" title="茴香脑 – Chinese" lang="zh" hreflang="zh" data-title="茴香脑" 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/Q27105777#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/Anethole" 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"><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>Anethole </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Anethole_acsv.svg" class="mw-file-description"><img alt="Skeletal formula of anethole" src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f2/Anethole_acsv.svg/220px-Anethole_acsv.svg.png" decoding="async" width="220" height="84" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f2/Anethole_acsv.svg/330px-Anethole_acsv.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f2/Anethole_acsv.svg/440px-Anethole_acsv.svg.png 2x" data-file-width="512" data-file-height="196" /></a></span> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Anethole-3D-balls.png" class="mw-file-description"><img alt="Ball-and-stick model of the anethole molecule" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c7/Anethole-3D-balls.png/220px-Anethole-3D-balls.png" decoding="async" width="220" height="131" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c7/Anethole-3D-balls.png/330px-Anethole-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c7/Anethole-3D-balls.png/440px-Anethole-3D-balls.png 2x" data-file-width="2000" data-file-height="1188" /></a></span> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Preferred_IUPAC_name" title="Preferred IUPAC name">Preferred IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;">1-Methoxy-4-[(<i>E</i>)-prop-1-enyl]benzene<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup></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;">(<i>E</i>)-1-Methoxy-4-(prop-1-en-1-yl)benzene<br />(<i>E</i>)-1-Methoxy-4-(1-propenyl)benzene<br /><i>para</i>-Methoxyphenylpropene<br /><i>p</i>-Propenylanisole<br />Isoestragole<br /><i>trans</i>-1-Methoxy-4-(prop-1-enyl)benzene</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=4180-23-8">4180-23-8</a></span> <i>E</i> isomer</li><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=104-46-1">104-46-1</a></span> Unspecified stereochemistry (most commonly used CAS, implicitly <i>E</i>)</li><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=25679-28-1">25679-28-1</a></span> <i>Z</i> isomer</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%28c1ccc%28%5CC%3DC%5CC%29cc1%29C">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=35616">CHEBI:35616</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/ChEMBL452630">ChEMBL452630</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.553166.html">553166</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/100.002.914">100.002.914</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q27105777#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/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/D02377">D02377</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/637563">637563</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/Q3JEK5DO4K">Q3JEK5DO4K</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/DTXSID4020086">DTXSID4020086</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q27105777#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/C10H12O/c1-3-4-9-5-7-10(11-2)8-6-9/h3-8H,1-2H3/b4-3+<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: RUVINXPYWBROJD-ONEGZZNKSA-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/C10H12O/c1-3-4-9-5-7-10(11-2)8-6-9/h3-8H,1-2H3/b4-3+</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: RUVINXPYWBROJD-ONEGZZNKBR</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(c1ccc(\C=C\C)cc1)C</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>10</sub><span title="Hydrogen">H</span><sub>12</sub><span title="Oxygen">O</span> </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td><span class="nowrap"><span data-sort-value="7002148205000000000♠"></span>148.205</span> g/mol   </td></tr> <tr> <td><a href="/wiki/Density" title="Density">Density</a> </td> <td>0.998 g/cm<sup>3</sup> </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>20 to 21 °C (68 to 70 °F; 293 to 294 K) </td></tr> <tr> <td><a href="/wiki/Boiling_point" title="Boiling point">Boiling point</a> </td> <td>234 °C (453 °F; 507 K) <br />81 °C (178 °F; 354 K) at 2 mmHg </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="3004040000000000000♠"></span>−9.60<span style="margin-left:0.25em;margin-right:0.15em;">×</span>10<sup>−5</sup> cm<sup>3</sup>/mol</span> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Hazards </th></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="https://web.archive.org/web/20010905233920/http://physchem.ox.ac.uk/MSDS/AN/anethole.html">External MSDS</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/Anisole" title="Anisole">anisole</a><br /><a href="/wiki/Estragole" title="Estragole">estragole</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=443390450&page2=Anethole">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>Anethole</b> (also known as <b>anise camphor</b>)<sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> is an <a href="/wiki/Organic_compound" title="Organic compound">organic compound</a> that is widely used as a <a href="/wiki/Flavoring" title="Flavoring">flavoring</a> substance. It is a derivative of the <a href="/wiki/Aromatic" class="mw-redirect" title="Aromatic">aromatic</a> compound <a href="/wiki/Allylbenzene" title="Allylbenzene">allylbenzene</a> and occurs widely in the <a href="/wiki/Essential_oil" title="Essential oil">essential oils</a> of plants. It is in the class of <a href="/wiki/Phenylpropanoid" title="Phenylpropanoid">phenylpropanoid</a> organic compounds. It contributes a large component of the odor and flavor of <a href="/wiki/Anise" title="Anise">anise</a> and <a href="/wiki/Fennel" title="Fennel">fennel</a> (both in the botanical family <a href="/wiki/Apiaceae" title="Apiaceae">Apiaceae</a>), <a href="/wiki/Syzygium_anisatum" title="Syzygium anisatum">anise myrtle</a> (<a href="/wiki/Myrtaceae" title="Myrtaceae">Myrtaceae</a>), <a href="/wiki/Liquorice" title="Liquorice">liquorice</a> (<a href="/wiki/Fabaceae" title="Fabaceae">Fabaceae</a>), magnolia blossoms, and <a href="/wiki/Star_anise" title="Star anise">star anise</a> (<a href="/wiki/Schisandraceae" title="Schisandraceae">Schisandraceae</a>). Closely related to anethole is its <a href="/wiki/Isomer" title="Isomer">isomer</a> <a href="/wiki/Estragole" title="Estragole">estragole</a>, which is abundant in <a href="/wiki/Tarragon" title="Tarragon">tarragon</a> (<a href="/wiki/Asteraceae" title="Asteraceae">Asteraceae</a>) and <a href="/wiki/Basil" title="Basil">basil</a> (<a href="/wiki/Lamiaceae" title="Lamiaceae">Lamiaceae</a>), and has a flavor reminiscent of anise. It is a colorless, fragrant, mildly volatile liquid.<sup class="noprint Inline-Template" style="margin-left:0.1em; white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Please_clarify" title="Wikipedia:Please clarify"><span title="does this statement refer to anethole or estragole? (October 2023)">clarification needed</span></a></i>]</sup><sup id="cite_ref-Ullmann_3-0" class="reference"><a href="#cite_note-Ullmann-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> Anethole is only slightly soluble in <a href="/wiki/Water" title="Water">water</a> but exhibits high solubility in <a href="/wiki/Ethanol" title="Ethanol">ethanol</a>. This trait causes certain anise-flavored <a href="/wiki/Liqueur" title="Liqueur">liqueurs</a> to become opaque when diluted with water; this is called the <a href="/wiki/Ouzo_effect" title="Ouzo effect">ouzo effect</a>. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Structure_and_production">Structure and production</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Anethole&action=edit&section=1" title="Edit section: Structure and production"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Anethole is an aromatic, <a href="/wiki/Saturated_and_unsaturated_compounds" title="Saturated and unsaturated compounds">unsaturated</a> <a href="/wiki/Ether" title="Ether">ether</a> related to <a href="/wiki/Monolignol" title="Monolignol">lignols</a>. It exists as both <a href="/wiki/Cis-trans_isomerism" class="mw-redirect" title="Cis-trans isomerism"><i>cis</i>–<i>trans</i> isomers</a> (see also <a href="/wiki/E-Z_notation" class="mw-redirect" title="E-Z notation"><i>E</i>–<i>Z</i> notation</a>), involving the double bond outside the ring. The more abundant isomer, and the one preferred for use, is the <i>trans</i> or <i>E</i> isomer.<sup id="cite_ref-chemistry-europe.onlinelibrary.wiley.com_4-0" class="reference"><a href="#cite_note-chemistry-europe.onlinelibrary.wiley.com-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p><p>Like related compounds, anethole is poorly soluble in water. Historically, this property was used to detect adulteration in samples.<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p><p>Most anethole is obtained from <a href="/wiki/Turpentine" title="Turpentine">turpentine</a>-like extracts from trees.<sup id="cite_ref-Ullmann_3-1" class="reference"><a href="#cite_note-Ullmann-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> Of only minor commercial significance, anethole can also be isolated from essential oils.<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Ashurst_8-0" class="reference"><a href="#cite_note-Ashurst-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p> <table class="wikitable"> <tbody><tr> <th>Essential oil </th> <th>World production </th> <th><i>Trans</i>-anethole </th></tr> <tr> <td>Anise </td> <td>8 tonnes (1999) </td> <td>95% </td></tr> <tr> <td>Star anise </td> <td>400 tonnes (1999), mostly from China </td> <td>87% </td></tr> <tr> <td>Fennel </td> <td>25 tonnes (1999), mostly from Spain </td> <td>70% </td></tr></tbody></table> <p>Currently Banwari Chemicals Pvt Ltd situated in Bhiwadi, Rajasthan, India is the leading manufacturer of anethole. It is prepared commercially from 4-methoxy<a href="/wiki/Propiophenone" title="Propiophenone">propiophenone</a>,<sup id="cite_ref-chemistry-europe.onlinelibrary.wiley.com_4-1" class="reference"><a href="#cite_note-chemistry-europe.onlinelibrary.wiley.com-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> which is prepared from <a href="/wiki/Anisole" title="Anisole">anisole</a>.<sup id="cite_ref-Ullmann_3-2" class="reference"><a href="#cite_note-Ullmann-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </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=Anethole&action=edit&section=2" title="Edit section: Uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Flavoring">Flavoring</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Anethole&action=edit&section=3" title="Edit section: Flavoring"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Anethole is distinctly <a href="/wiki/Sweet" class="mw-redirect" title="Sweet">sweet</a>, measuring 13 times sweeter than <a href="/wiki/Sugar" title="Sugar">sugar</a>. It is perceived as being pleasant to the taste even at higher concentrations. It is used in alcoholic drinks <a href="/wiki/Ouzo" title="Ouzo">ouzo</a>, <a href="/wiki/Rak%C4%B1" title="Rakı">rakı</a>, <a href="/wiki/Anisette" title="Anisette">anisette</a> and <a href="/wiki/Absinthe" title="Absinthe">absinthe</a>, among others. It is also used in seasoning and confectionery applications, such as German <a href="/wiki/Lebkuchen" title="Lebkuchen">Lebkuchen</a>, oral hygiene products, and in small quantities in natural berry <a href="/wiki/Flavoring" title="Flavoring">flavors</a>.<sup id="cite_ref-Ashurst_8-1" class="reference"><a href="#cite_note-Ashurst-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Precursor_to_other_compounds">Precursor to other compounds</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Anethole&action=edit&section=4" title="Edit section: Precursor to other compounds"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Because they <a href="/wiki/Metabolism" title="Metabolism">metabolize</a> anethole into several <a href="/wiki/Aromatic_chemical_compound" class="mw-redirect" title="Aromatic chemical compound">aromatic chemical compounds</a>, some bacteria are candidates for use in commercial <a href="/wiki/Bioconversion" title="Bioconversion">bioconversion</a> of anethole to more valuable materials.<sup id="cite_ref-pmid11805095_11-0" class="reference"><a href="#cite_note-pmid11805095-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> Bacterial strains capable of using trans-anethole as the sole carbon source include JYR-1 (<i><a href="/wiki/Pseudomonas_putida" title="Pseudomonas putida">Pseudomonas putida</a></i>)<sup id="cite_ref-pmid16028980_12-0" class="reference"><a href="#cite_note-pmid16028980-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> and TA13 (<i><a href="/wiki/Arthrobacter_aurescens" class="mw-redirect" title="Arthrobacter aurescens">Arthrobacter aurescens</a></i>).<sup id="cite_ref-pmid11805095_11-1" class="reference"><a href="#cite_note-pmid11805095-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Research">Research</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Anethole&action=edit&section=5" title="Edit section: Research"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Antimicrobial_and_antifungal_activity">Antimicrobial and antifungal activity</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Anethole&action=edit&section=6" title="Edit section: Antimicrobial and antifungal activity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Anethole has potent <a href="/wiki/Antimicrobial" title="Antimicrobial">antimicrobial</a> properties, against <a href="/wiki/Bacteria" title="Bacteria">bacteria</a>, <a href="/wiki/Yeast" title="Yeast">yeasts</a>, and <a href="/wiki/Fungi" class="mw-redirect" title="Fungi">fungi</a>.<sup id="cite_ref-pmid11807977_13-0" class="reference"><a href="#cite_note-pmid11807977-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> Reported antibacterial properties include both <a href="/wiki/Bacteriostatic" class="mw-redirect" title="Bacteriostatic">bacteriostatic</a> and <a href="/wiki/Bactericidal" class="mw-redirect" title="Bactericidal">bactericidal</a> action against <i><a href="/wiki/Salmonella_enterica" title="Salmonella enterica">Salmonella enterica</a></i><sup id="cite_ref-pmid11743758_14-0" class="reference"><a href="#cite_note-pmid11743758-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> but not when used against <i>Salmonella</i> via a <a href="/wiki/Fumigation" title="Fumigation">fumigation</a> method.<sup id="cite_ref-pmid11307877_15-0" class="reference"><a href="#cite_note-pmid11307877-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> Antifungal activity includes increasing the effectiveness of some other <a href="/wiki/Phytochemical" title="Phytochemical">phytochemicals</a> (such as <a href="/wiki/Polygodial" title="Polygodial">polygodial</a>) against <i><a href="/wiki/Saccharomyces_cerevisiae" title="Saccharomyces cerevisiae">Saccharomyces cerevisiae</a></i> and <i><a href="/wiki/Candida_albicans" title="Candida albicans">Candida albicans</a></i>;<sup id="cite_ref-pmid17078111_16-0" class="reference"><a href="#cite_note-pmid17078111-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p><p><i><a href="/wiki/In_vitro" title="In vitro">In vitro</a></i>, anethole has <a href="/wiki/Antihelmintic" class="mw-redirect" title="Antihelmintic">antihelmintic</a> action on eggs and larvae of the <a href="/wiki/Domestic_sheep" class="mw-redirect" title="Domestic sheep">sheep</a> gastrointestinal <a href="/wiki/Nematode" title="Nematode">nematode</a> <i><a href="/wiki/Haemonchus_contortus" title="Haemonchus contortus">Haemonchus contortus</a></i>.<sup id="cite_ref-pmid17629623_17-0" class="reference"><a href="#cite_note-pmid17629623-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> Anethole also has nematicidal activity against the plant nematode <i><a href="/wiki/Meloidogyne_javanica" title="Meloidogyne javanica">Meloidogyne javanica</a></i> in vitro and in pots of <a href="/w/index.php?title=Cucumber_seedlings&action=edit&redlink=1" class="new" title="Cucumber seedlings (page does not exist)">cucumber seedlings</a>.<sup id="cite_ref-pmid18944489_18-0" class="reference"><a href="#cite_note-pmid18944489-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Insecticidal_activity">Insecticidal activity</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Anethole&action=edit&section=7" title="Edit section: Insecticidal activity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Anethole also is a promising insecticide. Several essential oils consisting mostly of anethole have <a href="/wiki/Insecticide" title="Insecticide">insecticidal</a> action against <a href="/wiki/Larva" title="Larva">larvae</a> of the <a href="/wiki/Mosquito" title="Mosquito">mosquito</a> <i><a href="/wiki/Ochlerotatus" title="Ochlerotatus">Ochlerotatus</a> caspius</i><sup id="cite_ref-pmid17368893_19-0" class="reference"><a href="#cite_note-pmid17368893-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> and <i><a href="/wiki/Aedes_aegypti" title="Aedes aegypti">Aedes aegypti</a></i>.<sup id="cite_ref-pmid15237942_20-0" class="reference"><a href="#cite_note-pmid15237942-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid16646345_21-0" class="reference"><a href="#cite_note-pmid16646345-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> In a similar manner, anethole itself is effective against the <a href="/wiki/Fungus_gnat" title="Fungus gnat">fungus gnat</a> <i>Lycoriella ingenua</i> (<a href="/wiki/Sciaridae" title="Sciaridae">Sciaridae</a>)<sup id="cite_ref-pmid16786497_22-0" class="reference"><a href="#cite_note-pmid16786497-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> and the <a href="/wiki/Mold_mite" class="mw-redirect" title="Mold mite">mold mite</a> <i>Tyrophagus putrescentiae</i>.<sup id="cite_ref-pmid15954709_23-0" class="reference"><a href="#cite_note-pmid15954709-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> Against the mite, anethole is a slightly more effective <a href="/wiki/Pesticide" title="Pesticide">pesticide</a> than <a href="/wiki/DEET" title="DEET">DEET</a>, but <a href="/wiki/Anisaldehyde" class="mw-redirect" title="Anisaldehyde">anisaldehyde</a>, a related natural compound that occurs with anethole in many essential oils, is 14 times more effective.<sup id="cite_ref-pmid15954709_23-1" class="reference"><a href="#cite_note-pmid15954709-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> The insecticidal action of anethole is greater as a <a href="/wiki/Fumigation" title="Fumigation">fumigant</a> than as a contact agent. <i>trans</i>-Anethole is highly effective as a fumigant against the <a href="/wiki/Cockroach" title="Cockroach">cockroach</a> <i><a href="/wiki/Blattella_germanica" class="mw-redirect" title="Blattella germanica">Blattella germanica</a></i><sup id="cite_ref-pmid11852640_24-0" class="reference"><a href="#cite_note-pmid11852640-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> and against adults of the <a href="/wiki/Weevil" title="Weevil">weevils</a> <i><a href="/wiki/Sitophilus_oryzae" class="mw-redirect" title="Sitophilus oryzae">Sitophilus oryzae</a></i>, <i><a href="/wiki/Callosobruchus_chinensis" title="Callosobruchus chinensis">Callosobruchus chinensis</a></i> and <a href="/wiki/Beetle" title="Beetle">beetle</a> <i><a href="/wiki/Lasioderma_serricorne" title="Lasioderma serricorne">Lasioderma serricorne</a></i>.<sup id="cite_ref-pmid11455661_25-0" class="reference"><a href="#cite_note-pmid11455661-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> </p><p>As well as an insect pesticide, anethole is an effective <a href="/wiki/Insect_repellent" title="Insect repellent">insect repellent</a> against mosquitos.<sup id="cite_ref-pmid12963152_26-0" class="reference"><a href="#cite_note-pmid12963152-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Ouzo_effect">Ouzo effect</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Anethole&action=edit&section=8" title="Edit section: Ouzo effect"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Preparing_absinthe.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/22/Preparing_absinthe.jpg/220px-Preparing_absinthe.jpg" decoding="async" width="220" height="279" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/22/Preparing_absinthe.jpg/330px-Preparing_absinthe.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/22/Preparing_absinthe.jpg/440px-Preparing_absinthe.jpg 2x" data-file-width="464" data-file-height="588" /></a><figcaption>Diluting <a href="/wiki/Absinthe" title="Absinthe">absinthe</a> with water produces a spontaneous microemulsion (<a href="/wiki/Ouzo_effect" title="Ouzo effect">ouzo effect</a>)</figcaption></figure> <p>Anethole is responsible for the "<a href="/wiki/Ouzo_effect" title="Ouzo effect">ouzo effect</a>" (also "louche effect"), the spontaneous formation of a <a href="/wiki/Microemulsion" title="Microemulsion">microemulsion</a><sup id="cite_ref-Sitnikova+2005_27-0" class="reference"><a href="#cite_note-Sitnikova+2005-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup><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> that gives many alcoholic beverages containing anethole and water their cloudy appearance.<sup id="cite_ref-Sanchez-Dominguez_Rodriguez-Abreu_2016_p._369_29-0" class="reference"><a href="#cite_note-Sanchez-Dominguez_Rodriguez-Abreu_2016_p._369-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> Such a spontaneous microemulsion has many potential commercial applications in the food and pharmaceutical industries.<sup id="cite_ref-pmid17229398_30-0" class="reference"><a href="#cite_note-pmid17229398-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Precursor_to_illicit_drugs">Precursor to illicit drugs</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Anethole&action=edit&section=9" title="Edit section: Precursor to illicit drugs"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Anethole is an inexpensive chemical precursor for <a href="/wiki/Paramethoxyamphetamine" class="mw-redirect" title="Paramethoxyamphetamine">paramethoxyamphetamine</a> (PMA),<sup id="cite_ref-pmid12742705_31-0" class="reference"><a href="#cite_note-pmid12742705-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> and is used in its clandestine manufacture.<sup id="cite_ref-pmid15240033_32-0" class="reference"><a href="#cite_note-pmid15240033-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> Anethole is present in the essential oil from <a href="/wiki/Guarana" title="Guarana">guarana</a>, which has psychoactive effects typically attributed to its caffeine content. The absence of PMA or any other known psychoactive derivative of anethole in human urine after ingestion of guarana leads to the conclusion that any psychoactive effect of guarana is not due to aminated anethole metabolites.<sup id="cite_ref-pmid8765992_33-0" class="reference"><a href="#cite_note-pmid8765992-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> </p><p>Anethole is also present in <a href="/wiki/Absinthe" title="Absinthe">absinthe</a>, a <a href="/wiki/Liquor" title="Liquor">liquor</a> with a reputation for <a href="/wiki/Psychedelics,_dissociatives_and_deliriants" class="mw-redirect" title="Psychedelics, dissociatives and deliriants">psychoactive</a> effects; these effects, however, are attributed to <a href="/wiki/Ethanol" title="Ethanol">ethanol</a>.<sup id="cite_ref-pmid18429531_34-0" class="reference"><a href="#cite_note-pmid18429531-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> (See also <a href="/wiki/Thujone" title="Thujone">thujone</a>, <a href="/wiki/Anethole_dithione" class="mw-redirect" title="Anethole dithione">anethole dithione</a> (ADT), and <a href="/wiki/Anethole_trithione" title="Anethole trithione">anethole trithione</a> (ATT).) </p> <div class="mw-heading mw-heading3"><h3 id="Estrogen_and_prolactin">Estrogen and prolactin</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Anethole&action=edit&section=10" title="Edit section: Estrogen and prolactin"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Anethole has <a href="/wiki/Estrogen" title="Estrogen">estrogenic</a> activity.<sup id="cite_ref-Jordan1986_35-0" class="reference"><a href="#cite_note-Jordan1986-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-36" class="reference"><a href="#cite_note-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-37" class="reference"><a href="#cite_note-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup> It has been found to significantly increase <a href="/wiki/Uterine" class="mw-redirect" title="Uterine">uterine</a> weight in immature female rats.<sup id="cite_ref-TisserandYoung2013_38-0" class="reference"><a href="#cite_note-TisserandYoung2013-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup> </p><p>Fennel, which contains anethole, has been found to have a <a href="/wiki/Galactagogue" title="Galactagogue">galactagogue</a> effect in animals. Anethole bears a structural resemblance to <a href="/wiki/Catecholamine" title="Catecholamine">catecholamines</a> like <a href="/wiki/Dopamine" title="Dopamine">dopamine</a> and may displace dopamine from its receptors and thereby disinhibit <a href="/wiki/Prolactin" title="Prolactin">prolactin</a> secretion, which in turn may be responsible for the galactagogue effects.<sup id="cite_ref-BoneMills2013_39-0" class="reference"><a href="#cite_note-BoneMills2013-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Safety">Safety</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Anethole&action=edit&section=11" title="Edit section: Safety"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In the USA, anethole is <a href="/wiki/Generally_recognized_as_safe" title="Generally recognized as safe">generally recognized as safe</a> (GRAS). After a hiatus due to safety concerns, anethole was reaffirmed by <a href="/wiki/Flavor_and_Extract_Manufacturers_Association" title="Flavor and Extract Manufacturers Association">Flavor and Extract Manufacturers Association</a> (FEMA) as GRAS.<sup id="cite_ref-pmid10496381_40-0" class="reference"><a href="#cite_note-pmid10496381-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup> The concerns related to liver toxicity and possible carcinogenic activity reported in <a href="/wiki/Rat" title="Rat">rats</a>.<sup id="cite_ref-pmid2467866_41-0" class="reference"><a href="#cite_note-pmid2467866-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> Anethole is associated with a slight increase in <a href="/wiki/Liver_cancer" title="Liver cancer">liver cancer</a> in rats,<sup id="cite_ref-pmid2467866_41-1" class="reference"><a href="#cite_note-pmid2467866-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> although the evidence is scant and generally regarded as evidence that anethole is <i>not</i> a <a href="/wiki/Carcinogen" title="Carcinogen">carcinogen</a>.<sup id="cite_ref-pmid2467866_41-2" class="reference"><a href="#cite_note-pmid2467866-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid12151622_42-0" class="reference"><a href="#cite_note-pmid12151622-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup> An evaluation of anethole by the <a href="/wiki/Joint_FAO/WHO_Expert_Committee_on_Food_Additives" title="Joint FAO/WHO Expert Committee on Food Additives">Joint FAO/WHO Expert Committee on Food Additives</a> (JECFA) found its notable <a href="/wiki/Pharmacology" title="Pharmacology">pharmacologic</a> properties to be reduction in motor activity, lowering of <a href="/wiki/Normal_human_body_temperature" class="mw-redirect" title="Normal human body temperature">body temperature</a>, and <a href="/wiki/Hypnotic" title="Hypnotic">hypnotic</a>, <a href="/wiki/Analgesic" title="Analgesic">analgesic</a>, and <a href="/wiki/Anticonvulsant" title="Anticonvulsant">anticonvulsant</a> effects.<sup id="cite_ref-JECFA466_43-0" class="reference"><a href="#cite_note-JECFA466-43"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup> A subsequent evaluation by JECFA found some reason for concern regarding <a href="/wiki/Carcinogenicity" class="mw-redirect" title="Carcinogenicity">carcinogenicity</a>, but there is currently insufficient data to support this.<sup id="cite_ref-JECFA717_44-0" class="reference"><a href="#cite_note-JECFA717-44"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup> At this time, the JECFA summary of these evaluations is that anethole has "no safety concern at current levels of intake when used as a flavoring agent".<sup id="cite_ref-JECeval_45-0" class="reference"><a href="#cite_note-JECeval-45"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup> </p><p>In large quantities, anethole is slightly <a href="/wiki/Toxic" class="mw-redirect" title="Toxic">toxic</a> and may act as an irritant.<sup id="cite_ref-46" class="reference"><a href="#cite_note-46"><span class="cite-bracket">[</span>46<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=Anethole&action=edit&section=12" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>That an oil could be extracted from anise and fennel had been known since the <a href="/wiki/Renaissance" title="Renaissance">Renaissance</a> by the German alchemist <a href="/wiki/Hieronymus_Brunschwig" title="Hieronymus Brunschwig">Hieronymus Brunschwig</a> (<abbr title="circa">c.</abbr><span style="white-space:nowrap;"> 1450</span> – c.<span style="white-space:nowrap;"> 1512</span>), the German botanist <a href="/wiki/Adam_Lonicer" title="Adam Lonicer">Adam Lonicer</a> (1528–1586), and the German physician <a href="/wiki/Valerius_Cordus" title="Valerius Cordus">Valerius Cordus</a> (1515–1544), among others.<sup id="cite_ref-semmler_47-0" class="reference"><a href="#cite_note-semmler-47"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup> Anethole was first investigated chemically by the Swiss chemist <a href="/wiki/Nicolas-Th%C3%A9odore_de_Saussure" class="mw-redirect" title="Nicolas-Théodore de Saussure">Nicolas-Théodore de Saussure</a> in 1820.<sup id="cite_ref-48" class="reference"><a href="#cite_note-48"><span class="cite-bracket">[</span>48<span class="cite-bracket">]</span></a></sup> In 1832, the French chemist <a href="/wiki/Jean_Baptiste_Dumas" class="mw-redirect" title="Jean Baptiste Dumas">Jean Baptiste Dumas</a> determined that the crystallizable components of anise oil and fennel oil were identical, and he determined anethole's empirical formula.<sup id="cite_ref-49" class="reference"><a href="#cite_note-49"><span class="cite-bracket">[</span>49<span class="cite-bracket">]</span></a></sup> In 1845, the French chemist <a href="/wiki/Charles_Fr%C3%A9d%C3%A9ric_Gerhardt" title="Charles Frédéric Gerhardt">Charles Gerhardt</a> coined the term <i>anethol</i> – from the Latin <i>anethum</i> (anise) + <i>oleum</i> (oil) – for the fundamental compound from which a family of related compounds was derived.<sup id="cite_ref-50" class="reference"><a href="#cite_note-50"><span class="cite-bracket">[</span>50<span class="cite-bracket">]</span></a></sup> Although the German chemist <a href="/wiki/Emil_Erlenmeyer" title="Emil Erlenmeyer">Emil Erlenmeyer</a> proposed the correct molecular structure for anethole in 1866,<sup id="cite_ref-51" class="reference"><a href="#cite_note-51"><span class="cite-bracket">[</span>51<span class="cite-bracket">]</span></a></sup> it was not until 1872, that the structure was accepted as correct.<sup id="cite_ref-semmler_47-1" class="reference"><a href="#cite_note-semmler-47"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Anethole&action=edit&section=13" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Category:Anise_liqueurs_and_spirits" title="Category:Anise liqueurs and spirits">Category:Anise liqueurs and spirits</a></li> <li><a href="/wiki/List_of_liqueurs#Anise-flavored_liqueurs" class="mw-redirect" title="List of liqueurs">List of liqueurs § Anise-flavored liqueurs</a></li> <li><a href="/wiki/Anol" title="Anol">Anol</a></li> <li><a href="/wiki/Chavicol" title="Chavicol">Chavicol</a></li> <li><a href="/wiki/Dianethole" title="Dianethole">Dianethole</a></li> <li><a href="/wiki/Fenchone" title="Fenchone">Fenchone</a></li> <li><a href="/wiki/Pseudoisoeugenol" title="Pseudoisoeugenol">Pseudoisoeugenol</a></li> <li><a href="/wiki/Safrole" title="Safrole">Safrole</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Anethole&action=edit&section=14" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist reflist-columns references-column-width" style="column-width: 30em;"> <ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/637563#section=IUPAC-Name&fullscreen=true">"Anethole"</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Anethole&rft_id=https%3A%2F%2Fpubchem.ncbi.nlm.nih.gov%2Fcompound%2F637563%23section%3DIUPAC-Name%26fullscreen%3Dtrue&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnethole" class="Z3988"></span></span> </li> <li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.collinsdictionary.com/us/dictionary/english/anise-camphor">"Anise camphor definition and meaning | Collins English Dictionary"</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Anise+camphor+definition+and+meaning+%26%23124%3B+Collins+English+Dictionary&rft_id=https%3A%2F%2Fwww.collinsdictionary.com%2Fus%2Fdictionary%2Fenglish%2Fanise-camphor&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnethole" class="Z3988"></span></span> </li> <li id="cite_note-Ullmann-3"><span class="mw-cite-backlink">^ <a href="#cite_ref-Ullmann_3-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Ullmann_3-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Ullmann_3-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFahlbuschHammerschmidtPantenPickenhagen" class="citation encyclopaedia cs1">Fahlbusch, Karl-Georg; Hammerschmidt, Franz-Josef; Panten, Johannes; Pickenhagen, Wilhelm; Schatkowski, Dietmar; Bauer, Kurt; Garbe, 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University of Wisconsin Press. pp. 21–22. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-299-10480-1" title="Special:BookSources/978-0-299-10480-1"><bdi>978-0-299-10480-1</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Estrogen%2FAntiestrogen+Action+and+Breast+Cancer+Therapy&rft.pages=21-22&rft.pub=University+of+Wisconsin+Press&rft.date=1986&rft.isbn=978-0-299-10480-1&rft.aulast=Jordan&rft.aufirst=Virgil+Craig&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D7WmLZfGXST0C%26pg%3DPA21&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnethole" class="Z3988"></span></span> </li> <li id="cite_note-36"><span class="mw-cite-backlink"><b><a href="#cite_ref-36">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHowesHoughtonBarlowPocock2002" class="citation journal cs1">Howes, M.-J. R.; Houghton, P. J.; Barlow, D. J.; Pocock, V. J.; Milligan, S. R. (November 2002). <a rel="nofollow" class="external text" href="https://doi.org/10.1211%2F002235702216">"Assessment of estrogenic activity in some common essential oil constituents"</a>. <i>The Journal of Pharmacy and Pharmacology</i>. <b>54</b> (11): 1521–1528. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1211%2F002235702216">10.1211/002235702216</a></span>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0022-3573">0022-3573</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/12495555">12495555</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:28650422">28650422</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Journal+of+Pharmacy+and+Pharmacology&rft.atitle=Assessment+of+estrogenic+activity+in+some+common+essential+oil+constituents&rft.volume=54&rft.issue=11&rft.pages=1521-1528&rft.date=2002-11&rft.issn=0022-3573&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A28650422%23id-name%3DS2CID&rft_id=info%3Apmid%2F12495555&rft_id=info%3Adoi%2F10.1211%2F002235702216&rft.aulast=Howes&rft.aufirst=M.-J.+R.&rft.au=Houghton%2C+P.+J.&rft.au=Barlow%2C+D.+J.&rft.au=Pocock%2C+V.+J.&rft.au=Milligan%2C+S.+R.&rft_id=https%3A%2F%2Fdoi.org%2F10.1211%252F002235702216&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnethole" class="Z3988"></span></span> </li> <li id="cite_note-37"><span class="mw-cite-backlink"><b><a href="#cite_ref-37">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFAlbert-Puleo1980" class="citation journal cs1">Albert-Puleo, M. (December 1980). <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/6999244/">"Fennel and anise as estrogenic agents"</a>. <i>Journal of Ethnopharmacology</i>. <b>2</b> (4): 337–344. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fs0378-8741%2880%2981015-4">10.1016/s0378-8741(80)81015-4</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0378-8741">0378-8741</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/6999244">6999244</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Ethnopharmacology&rft.atitle=Fennel+and+anise+as+estrogenic+agents&rft.volume=2&rft.issue=4&rft.pages=337-344&rft.date=1980-12&rft.issn=0378-8741&rft_id=info%3Apmid%2F6999244&rft_id=info%3Adoi%2F10.1016%2Fs0378-8741%2880%2981015-4&rft.aulast=Albert-Puleo&rft.aufirst=M.&rft_id=https%3A%2F%2Fpubmed.ncbi.nlm.nih.gov%2F6999244%2F&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnethole" class="Z3988"></span></span> </li> <li id="cite_note-TisserandYoung2013-38"><span class="mw-cite-backlink"><b><a href="#cite_ref-TisserandYoung2013_38-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFTisserandYoung2013" class="citation book cs1">Tisserand, Robert; Young, Rodney (2013). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=DbEKAQAAQBAJ&pg=PA150"><i>Essential Oil Safety: A Guide for Health Care Professionals</i></a>. Elsevier Health Sciences. p. 150. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-7020-5434-1" title="Special:BookSources/978-0-7020-5434-1"><bdi>978-0-7020-5434-1</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Essential+Oil+Safety%3A+A+Guide+for+Health+Care+Professionals&rft.pages=150&rft.pub=Elsevier+Health+Sciences&rft.date=2013&rft.isbn=978-0-7020-5434-1&rft.aulast=Tisserand&rft.aufirst=Robert&rft.au=Young%2C+Rodney&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DDbEKAQAAQBAJ%26pg%3DPA150&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnethole" class="Z3988"></span></span> </li> <li id="cite_note-BoneMills2013-39"><span class="mw-cite-backlink"><b><a href="#cite_ref-BoneMills2013_39-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBoneMills2013" class="citation book cs1">Bone, Kerry; Mills, Simon Y. (2013). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=5V1QlqHazcwC&pg=PA559"><i>Principles and Practice of Phytotherapy</i></a>. Modern Herbal Medicine. Vol. 2. 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L.; Doull, J.; Goodman, J. I.; Munro, I. C.; Portoghese, P. S.; Wagner, B. M.; Weil, C. S.; Woods, L. A.; Adams, T. B.; Lucas, C. D.; Ford, R. A. (1999). "The FEMA GRAS assessment of <i>trans</i>-anethole used as a flavouring substance". <i>Food and Chemical Toxicology</i>. <b>37</b> (7): 789–811. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FS0278-6915%2899%2900037-X">10.1016/S0278-6915(99)00037-X</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/10496381">10496381</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Food+and+Chemical+Toxicology&rft.atitle=The+FEMA+GRAS+assessment+of+trans-anethole+used+as+a+flavouring+substance&rft.volume=37&rft.issue=7&rft.pages=789-811&rft.date=1999&rft_id=info%3Adoi%2F10.1016%2FS0278-6915%2899%2900037-X&rft_id=info%3Apmid%2F10496381&rft.aulast=Newberne&rft.aufirst=P.&rft.au=Smith%2C+R.+L.&rft.au=Doull%2C+J.&rft.au=Goodman%2C+J.+I.&rft.au=Munro%2C+I.+C.&rft.au=Portoghese%2C+P.+S.&rft.au=Wagner%2C+B.+M.&rft.au=Weil%2C+C.+S.&rft.au=Woods%2C+L.+A.&rft.au=Adams%2C+T.+B.&rft.au=Lucas%2C+C.+D.&rft.au=Ford%2C+R.+A.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnethole" class="Z3988"></span></span> </li> <li id="cite_note-pmid2467866-41"><span class="mw-cite-backlink">^ <a href="#cite_ref-pmid2467866_41-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-pmid2467866_41-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-pmid2467866_41-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFNewberneCarltonBrown1989" class="citation journal cs1">Newberne, P. M.; Carlton, W. W.; Brown, W. R. (1989). "Histopathological evaluation of proliferative liver lesions in rats fed trans-anethole in chronic studies". <i>Food and Chemical Toxicology</i>. <b>27</b> (1): 21–26. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2F0278-6915%2889%2990087-2">10.1016/0278-6915(89)90087-2</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/2467866">2467866</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Food+and+Chemical+Toxicology&rft.atitle=Histopathological+evaluation+of+proliferative+liver+lesions+in+rats+fed+trans-anethole+in+chronic+studies&rft.volume=27&rft.issue=1&rft.pages=21-26&rft.date=1989&rft_id=info%3Adoi%2F10.1016%2F0278-6915%2889%2990087-2&rft_id=info%3Apmid%2F2467866&rft.aulast=Newberne&rft.aufirst=P.+M.&rft.au=Carlton%2C+W.+W.&rft.au=Brown%2C+W.+R.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnethole" class="Z3988"></span></span> </li> <li id="cite_note-pmid12151622-42"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid12151622_42-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWaddell2002" class="citation journal cs1">Waddell, W. J. (2002). <a rel="nofollow" class="external text" href="https://doi.org/10.1093%2Ftoxsci%2F68.2.275">"Thresholds of carcinogenicity of flavors"</a>. <i>Toxicological Sciences</i>. <b>68</b> (2): 275–279. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1093%2Ftoxsci%2F68.2.275">10.1093/toxsci/68.2.275</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/12151622">12151622</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Toxicological+Sciences&rft.atitle=Thresholds+of+carcinogenicity+of+flavors&rft.volume=68&rft.issue=2&rft.pages=275-279&rft.date=2002&rft_id=info%3Adoi%2F10.1093%2Ftoxsci%2F68.2.275&rft_id=info%3Apmid%2F12151622&rft.aulast=Waddell&rft.aufirst=W.+J.&rft_id=https%3A%2F%2Fdoi.org%2F10.1093%252Ftoxsci%252F68.2.275&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnethole" class="Z3988"></span></span> </li> <li id="cite_note-JECFA466-43"><span class="mw-cite-backlink"><b><a href="#cite_ref-JECFA466_43-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFJoint_FAO/WHO_Expert_Committee_on_Food_Additives" class="citation web cs1">Joint FAO/WHO Expert Committee on Food Additives. <a rel="nofollow" class="external text" href="http://www.inchem.org/documents/jecfa/jecmono/v14je02.htm">"<i>trans</i>-Anethole"</a>. WHO Food Additives Series. International Program on Chemical Safety (IPCS).</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=trans-Anethole&rft.series=WHO+Food+Additives+Series&rft.pub=International+Program+on+Chemical+Safety+%28IPCS%29&rft.au=Joint+FAO%2FWHO+Expert+Committee+on+Food+Additives&rft_id=http%3A%2F%2Fwww.inchem.org%2Fdocuments%2Fjecfa%2Fjecmono%2Fv14je02.htm&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnethole" class="Z3988"></span></span> </li> <li id="cite_note-JECFA717-44"><span class="mw-cite-backlink"><b><a href="#cite_ref-JECFA717_44-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFJoint_FAO/WHO_Expert_Committee_on_Food_Additives1998" class="citation web cs1">Joint FAO/WHO Expert Committee on Food Additives (1998). <a rel="nofollow" class="external text" href="http://www.inchem.org/documents/jecfa/jecmono/v28je10.htm">"<i>trans</i>-Anethole"</a>. WHO Food Additives Series. International Program on Chemical Safety (IPCS).</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=trans-Anethole&rft.series=WHO+Food+Additives+Series&rft.pub=International+Program+on+Chemical+Safety+%28IPCS%29&rft.date=1998&rft.au=Joint+FAO%2FWHO+Expert+Committee+on+Food+Additives&rft_id=http%3A%2F%2Fwww.inchem.org%2Fdocuments%2Fjecfa%2Fjecmono%2Fv28je10.htm&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnethole" class="Z3988"></span></span> </li> <li id="cite_note-JECeval-45"><span class="mw-cite-backlink"><b><a href="#cite_ref-JECeval_45-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://www.inchem.org/documents/jecfa/jeceval/jec_137.htm">"Summary of Evaluations Performed by the Joint FAO/WHO Expert Committee on Food Additives: <i>trans</i>-Anethole"</a>. International Program on Chemical Safety (IPCS). 2001-11-12. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20090311035152/http://www.inchem.org/documents/jecfa/jeceval/jec_137.htm">Archived</a> from the original on 2009-03-11<span class="reference-accessdate">. Retrieved <span class="nowrap">2009-03-10</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Summary+of+Evaluations+Performed+by+the+Joint+FAO%2FWHO+Expert+Committee+on+Food+Additives%3A+trans-Anethole&rft.pub=International+Program+on+Chemical+Safety+%28IPCS%29&rft.date=2001-11-12&rft_id=http%3A%2F%2Fwww.inchem.org%2Fdocuments%2Fjecfa%2Fjeceval%2Fjec_137.htm&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnethole" class="Z3988"></span></span> </li> <li id="cite_note-46"><span class="mw-cite-backlink"><b><a href="#cite_ref-46">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20080615174611/http://msds.chem.ox.ac.uk/AN/anethole.html">"Safety data for anethole"</a>. Physical & Theoretical Chemistry Laboratory Safety, Oxford University. Archived from <a rel="nofollow" class="external text" href="http://msds.chem.ox.ac.uk/AN/anethole.html">the original</a> on 2008-06-15<span class="reference-accessdate">. Retrieved <span class="nowrap">2009-03-10</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Safety+data+for+anethole&rft.pub=Physical+%26+Theoretical+Chemistry+Laboratory+Safety%2C+Oxford+University&rft_id=http%3A%2F%2Fmsds.chem.ox.ac.uk%2FAN%2Fanethole.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnethole" class="Z3988"></span></span> </li> <li id="cite_note-semmler-47"><span class="mw-cite-backlink">^ <a href="#cite_ref-semmler_47-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-semmler_47-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text">See: <ul><li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSemmler1907" class="citation book cs1 cs1-prop-foreign-lang-source">Semmler, F. W. (1907). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=JlA3AQAAMAAJ&pg=PA76"><i>Die ätherischen Öle nach ihren chemischen Bestandteilen unter Berücksichtigung der geschichtlichen Entwicklung</i></a> [<i>The volatile oils according to their chemical components with regard to their historical development</i>] (in German). Vol. 4. Leipzig: Veit & Co. p. 76.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Die+%C3%A4therischen+%C3%96le+nach+ihren+chemischen+Bestandteilen+unter+Ber%C3%BCcksichtigung+der+geschichtlichen+Entwicklung&rft.place=Leipzig&rft.pages=76&rft.pub=Veit+%26+Co.&rft.date=1907&rft.aulast=Semmler&rft.aufirst=F.+W.&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DJlA3AQAAMAAJ%26pg%3DPA76&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnethole" class="Z3988"></span></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLippmann1921" class="citation book cs1 cs1-prop-foreign-lang-source">Lippmann, Edmund Oskar von (1921). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=LDyHBwAAQBAJ&pg=PA1">"§ 339. Anethol"</a>. <i>Zeittafeln zur Geschichte der Organischen Chemie</i> [<i>Timeline of the history of organic chemistry</i>] (in German). Berlin: Springer-Verlag. p. 1. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9783662246665" title="Special:BookSources/9783662246665"><bdi>9783662246665</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=%C2%A7+339.+Anethol&rft.btitle=Zeittafeln+zur+Geschichte+der+Organischen+Chemie&rft.place=Berlin&rft.pages=1&rft.pub=Springer-Verlag&rft.date=1921&rft.isbn=9783662246665&rft.aulast=Lippmann&rft.aufirst=Edmund+Oskar+von&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DLDyHBwAAQBAJ%26pg%3DPA1&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnethole" class="Z3988"></span></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGildemeisterHoffmann1900" class="citation book cs1">Gildemeister, Eduard; Hoffmann, Friedrich (1900). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=EAdKAAAAMAAJ&pg=PA563">"§ 307. Oil of anise"</a>. <i>The Volatile Oils</i>. Translated by Kremers, Edward. Milwaukee, Wisconsin: Review Publishing Co. pp. s558–s563.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=%C2%A7+307.+Oil+of+anise&rft.btitle=The+Volatile+Oils&rft.place=Milwaukee%2C+Wisconsin&rft.pages=s558-s563&rft.pub=Review+Publishing+Co.&rft.date=1900&rft.aulast=Gildemeister&rft.aufirst=Eduard&rft.au=Hoffmann%2C+Friedrich&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DEAdKAAAAMAAJ%26pg%3DPA563&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnethole" class="Z3988"></span></li></ul> </span></li> <li id="cite_note-48"><span class="mw-cite-backlink"><b><a href="#cite_ref-48">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFDe_Saussure1820" class="citation journal cs1 cs1-prop-foreign-lang-source">De Saussure, N.-T. (1820). <a rel="nofollow" class="external text" href="https://babel.hathitrust.org/cgi/pt?id=nyp.33433062741594;view=1up;seq=265">"Observations sur la combinaison de l'essence de citron avec l'acide muriatique, et sur quelques substances huileuses"</a> [Observations on the combination of lemon essence with muriatic acid, and on several oily substances]. <i>Annales de Chimie et de Physique</i>. Série 2 (in French). <b>13</b>: 259–284.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Annales+de+Chimie+et+de+Physique&rft.atitle=Observations+sur+la+combinaison+de+l%27essence+de+citron+avec+l%27acide+muriatique%2C+et+sur+quelques+substances+huileuses&rft.volume=13&rft.pages=259-284&rft.date=1820&rft.aulast=De+Saussure&rft.aufirst=N.-T.&rft_id=https%3A%2F%2Fbabel.hathitrust.org%2Fcgi%2Fpt%3Fid%3Dnyp.33433062741594%3Bview%3D1up%3Bseq%3D265&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnethole" class="Z3988"></span> See especially pp. 280–284.</span> </li> <li id="cite_note-49"><span class="mw-cite-backlink"><b><a href="#cite_ref-49">^</a></b></span> <span class="reference-text">See: <ul><li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFDumas1832" class="citation journal cs1 cs1-prop-foreign-lang-source">Dumas, J. (1832). <a rel="nofollow" class="external text" href="https://babel.hathitrust.org/cgi/pt?id=hvd.hx3dwm;view=1up;seq=235">"Mémoire sur les substances végétales qui se rapprochent du camphre, et sur quelques huiles essentielles"</a> [Memoir on plant substances that resemble camphor, and on several essential oils]. <i>Annales de Chimie et de Physique</i>. Série 2 (in French). <b>50</b>: 225–240.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Annales+de+Chimie+et+de+Physique&rft.atitle=M%C3%A9moire+sur+les+substances+v%C3%A9g%C3%A9tales+qui+se+rapprochent+du+camphre%2C+et+sur+quelques+huiles+essentielles&rft.volume=50&rft.pages=225-240&rft.date=1832&rft.aulast=Dumas&rft.aufirst=J.&rft_id=https%3A%2F%2Fbabel.hathitrust.org%2Fcgi%2Fpt%3Fid%3Dhvd.hx3dwm%3Bview%3D1up%3Bseq%3D235&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnethole" class="Z3988"></span> On p. 234, Dumas provides an <a href="/wiki/Empirical_formula" title="Empirical formula">empirical formula</a> C<sub>10</sub>H<sub>6</sub>O<sub><style data-mw-deduplicate="TemplateStyles:r1214402035">.mw-parser-output .sfrac{white-space:nowrap}.mw-parser-output .sfrac.tion,.mw-parser-output .sfrac .tion{display:inline-block;vertical-align:-0.5em;font-size:85%;text-align:center}.mw-parser-output .sfrac .num{display:block;line-height:1em;margin:0.0em 0.1em;border-bottom:1px solid}.mw-parser-output .sfrac .den{display:block;line-height:1em;margin:0.1em 0.1em}.mw-parser-output .sr-only{border:0;clip:rect(0,0,0,0);clip-path:polygon(0px 0px,0px 0px,0px 0px);height:1px;margin:-1px;overflow:hidden;padding:0;position:absolute;width:1px}</style><span class="sfrac">⁠<span class="tion"><span class="num">1</span><span class="sr-only">/</span><span class="den">2</span></span>⁠</span></sub> for anethol. If the subscripts are doubled and if the subscript for carbon is then halved (because Dumas, like many of his contemporaries, used the wrong <a href="/wiki/Atomic_mass" title="Atomic mass">atomic mass</a> for carbon, 6 instead of 12), then Dumas' empirical formula is correct.</li> <li>Dumas' finding that the crystallizable components of anise oil and fennel oil were identical was confirmed in 1833 by the team of Rodolphe Blanchet (1807–1864) and Ernst Sell (1808–1854). See: <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBlanchet1833" class="citation journal cs1 cs1-prop-foreign-lang-source">Blanchet, Sell (1833). <a rel="nofollow" class="external text" href="https://babel.hathitrust.org/cgi/pt?id=uva.x002457885;view=1up;seq=649">"Ueber die Zusammensetzung einiger organischer Substanzen"</a> [On the composition of some organic substances]. <i>Annalen der Pharmacie</i> (in German). <b>6</b> (3): 259–313. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fjlac.18330060304">10.1002/jlac.18330060304</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Annalen+der+Pharmacie&rft.atitle=Ueber+die+Zusammensetzung+einiger+organischer+Substanzen&rft.volume=6&rft.issue=3&rft.pages=259-313&rft.date=1833&rft_id=info%3Adoi%2F10.1002%2Fjlac.18330060304&rft.aulast=Blanchet&rft.aufirst=Sell&rft_id=https%3A%2F%2Fbabel.hathitrust.org%2Fcgi%2Fpt%3Fid%3Duva.x002457885%3Bview%3D1up%3Bseq%3D649&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnethole" class="Z3988"></span> See especially pp. 287–288.</li> <li>Dumas' empirical formula for anethole was confirmed in 1841 by the French chemist <a href="/wiki/Auguste_Andr%C3%A9_Thomas_Cahours" title="Auguste André Thomas Cahours">Auguste Cahours</a>. See: <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCahours1841" class="citation journal cs1 cs1-prop-foreign-lang-source">Cahours, A. A. T. (1841). <a rel="nofollow" class="external text" href="https://babel.hathitrust.org/cgi/pt?id=uva.x002489035;view=1up;seq=278">"Sur les essences de fenouil, de badiane et d'anis"</a> [On the essential oils of fennel, star anise, and anise]. <i>Annales de Chimie et de Physique</i>. Série 3 (in French). <b>2</b>: 274–308.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Annales+de+Chimie+et+de+Physique&rft.atitle=Sur+les+essences+de+fenouil%2C+de+badiane+et+d%27anis&rft.volume=2&rft.pages=274-308&rft.date=1841&rft.aulast=Cahours&rft.aufirst=A.+A.+T.&rft_id=https%3A%2F%2Fbabel.hathitrust.org%2Fcgi%2Fpt%3Fid%3Duva.x002489035%3Bview%3D1up%3Bseq%3D278&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnethole" class="Z3988"></span> See pp. 278–279. Note that the subscripts of Cahours' empirical formula (C<sub>40</sub>H<sub>24</sub>O<sub>2</sub>) must be divided by 2 and then the subscript for carbon must be divided again by 2 (because, like many chemists of his time, Cahours used the wrong atomic mass for carbon, 6 instead of 12). If these changes are made, the resulting empirical formula is correct.</li></ul> </span></li> <li id="cite_note-50"><span class="mw-cite-backlink"><b><a href="#cite_ref-50">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGerhardt1845" class="citation journal cs1 cs1-prop-foreign-lang-source">Gerhardt, Charles (1845). <a rel="nofollow" class="external text" href="https://babel.hathitrust.org/cgi/pt?id=njp.32101076785581;view=1up;seq=279">"Ueber die Identität des Dragonöls und des Anisöls"</a> [On the identity of tarragon oil and anise oil]. <i>Journal für praktische Chemie</i> (in German). <b>36</b>: 267–276. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fprac.18450360159">10.1002/prac.18450360159</a>. <q>[From p. 269:] Ich werde keinen neuen Namen für jede einzelne Art der folgenden physisch verschiedenen Arten annehmen. In meinem Werke bezeichne ich sie als Varietäten der Gattung „Anethol".</q> [I will adopt no new name for any individual species of the following physically different species. In my work, I designate them as varieties of the genus <i>anethol</i>.]</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+f%C3%BCr+praktische+Chemie&rft.atitle=Ueber+die+Identit%C3%A4t+des+Dragon%C3%B6ls+und+des+Anis%C3%B6ls&rft.volume=36&rft.pages=267-276&rft.date=1845&rft_id=info%3Adoi%2F10.1002%2Fprac.18450360159&rft.aulast=Gerhardt&rft.aufirst=Charles&rft_id=https%3A%2F%2Fbabel.hathitrust.org%2Fcgi%2Fpt%3Fid%3Dnjp.32101076785581%3Bview%3D1up%3Bseq%3D279&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnethole" class="Z3988"></span></span> </li> <li id="cite_note-51"><span class="mw-cite-backlink"><b><a href="#cite_ref-51">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFErlenmeyer1866" class="citation journal cs1 cs1-prop-foreign-lang-source">Erlenmeyer, Emil (1866). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=6sEwAAAAYAAJ&pg=PA472">"Ueber die Constitution des Anisols (Anethols)"</a> [On the constitution of anisol (anethol)]. <i>Zeitschrift für Chemie</i>. 2nd Series (in German). <b>2</b>: 472–474.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Zeitschrift+f%C3%BCr+Chemie&rft.atitle=Ueber+die+Constitution+des+Anisols+%28Anethols%29&rft.volume=2&rft.pages=472-474&rft.date=1866&rft.aulast=Erlenmeyer&rft.aufirst=Emil&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D6sEwAAAAYAAJ%26pg%3DPA472&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAnethole" class="Z3988"></span></span> </li> </ol></div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Anethole&action=edit&section=15" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><span class="noviewer" typeof="mw:File"><a href="/wiki/File:Commons-logo.svg" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/12px-Commons-logo.svg.png" decoding="async" width="12" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/18px-Commons-logo.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/24px-Commons-logo.svg.png 2x" data-file-width="1024" data-file-height="1376" /></a></span> Media related to <a href="https://commons.wikimedia.org/wiki/Category:Anethole" class="extiw" title="commons:Category:Anethole">Anethole</a> at Wikimedia Commons</li></ul> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist 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href="/wiki/Template:Phenylpropene" title="Template:Phenylpropene"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Phenylpropene" title="Template talk:Phenylpropene"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Phenylpropene" title="Special:EditPage/Template:Phenylpropene"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Types_of_phenylpropenes" style="font-size:114%;margin:0 4em">Types of <a href="/wiki/Phenylpropene" title="Phenylpropene">phenylpropenes</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phenylpropene" title="Phenylpropene">Phenylpropenes</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 class="mw-selflink selflink">Anethole</a></li> <li><a href="/wiki/Apiole" title="Apiole">Apiole</a></li> <li><a href="/w/index.php?title=Asaricin&action=edit&redlink=1" class="new" title="Asaricin (page does not exist)">Asaricin</a></li> <li><a href="/wiki/Asarone" title="Asarone">Asarone</a></li> <li><a href="/wiki/Carpacin" title="Carpacin">Carpacin</a></li> <li><a href="/wiki/Chavibetol" title="Chavibetol">Chavibetol</a></li> <li><a href="/wiki/Chavicol" title="Chavicol">Chavicol</a></li> <li><a href="/w/index.php?title=Croweacin&action=edit&redlink=1" class="new" title="Croweacin (page does not exist)">Croweacin</a></li> <li><a href="/wiki/Dillapiole" title="Dillapiole">Dillapiole</a></li> <li><a href="/wiki/Elemicin" title="Elemicin">Elemicin</a></li> <li><a href="/wiki/Estragole" title="Estragole">Estragole</a></li> <li><a href="/wiki/Eugenol" title="Eugenol">Eugenol</a></li> <li><a href="/w/index.php?title=Exalatacin&action=edit&redlink=1" class="new" title="Exalatacin (page does not exist)">Exalatacin</a></li> <li><a href="/w/index.php?title=Isoapiole&action=edit&redlink=1" class="new" title="Isoapiole (page does not exist)">Isoapiole</a></li> <li><a href="/w/index.php?title=Isodillapiole&action=edit&redlink=1" class="new" title="Isodillapiole (page does not exist)">Isodillapiole</a></li> <li><a href="/wiki/Isoeugenol" title="Isoeugenol">Isoeugenol</a></li> <li><a href="/w/index.php?title=Isomyristicin&action=edit&redlink=1" class="new" title="Isomyristicin (page does not exist)">Isomyristicin</a></li> <li><a href="/wiki/Isosafrole" title="Isosafrole">Isosafrole</a></li> <li><a href="/wiki/Methyl_eugenol" title="Methyl eugenol">Methyl eugenol</a></li> <li><a href="/wiki/Methyl_isoeugenol" title="Methyl isoeugenol">Methyl isoeugenol</a></li> <li><a href="/wiki/Myristicin" title="Myristicin">Myristicin</a></li> <li><a href="/wiki/Nothoapiole" title="Nothoapiole">Nothoapiole</a></li> <li><a href="/w/index.php?title=Osmorhizole&action=edit&redlink=1" class="new" title="Osmorhizole (page does not exist)">Osmorhizole</a></li> <li><a href="/wiki/Pseudoisoeugenol" title="Pseudoisoeugenol">Pseudoisoeugenol</a></li> <li><a href="/wiki/Safrole" title="Safrole">Safrole</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="Estrogen_receptor_modulators" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Estrogen_receptor_modulators" title="Template:Estrogen receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Estrogen_receptor_modulators" title="Template talk:Estrogen receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Estrogen_receptor_modulators" title="Special:EditPage/Template:Estrogen receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Estrogen_receptor_modulators" style="font-size:114%;margin:0 4em"><a href="/wiki/Estrogen_receptor" title="Estrogen receptor">Estrogen receptor</a> <a href="/wiki/Receptor_modulator" title="Receptor modulator">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Estrogen_receptor" title="Estrogen receptor"><abbr title="Estrogen receptor">ER</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Estrogen receptor</span></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:6em;;text-align:center">Agonists</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><i>Steroidal:</i> <a href="/wiki/2-Hydroxyestradiol" title="2-Hydroxyestradiol">2-Hydroxyestradiol</a></li> <li><a href="/wiki/2-Hydroxyestrone" title="2-Hydroxyestrone">2-Hydroxyestrone</a></li> <li><a href="/wiki/3-Methyl-19-methyleneandrosta-3,5-dien-17%CE%B2-ol" title="3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol">3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol</a></li> <li><a href="/wiki/3%CE%B1-Androstanediol" title="3α-Androstanediol">3α-Androstanediol</a></li> <li><a href="/w/index.php?title=3%CE%B1,5%CE%B1-Dihydrolevonorgestrel&action=edit&redlink=1" class="new" title="3α,5α-Dihydrolevonorgestrel (page does not exist)">3α,5α-Dihydrolevonorgestrel</a></li> <li><a href="/w/index.php?title=3%CE%B2,5%CE%B1-Dihydrolevonorgestrel&action=edit&redlink=1" class="new" title="3β,5α-Dihydrolevonorgestrel (page does not exist)">3β,5α-Dihydrolevonorgestrel</a></li> <li><a href="/wiki/3%CE%B1-Hydroxytibolone" title="3α-Hydroxytibolone">3α-Hydroxytibolone</a></li> <li><a href="/wiki/3%CE%B2-Hydroxytibolone" title="3β-Hydroxytibolone">3β-Hydroxytibolone</a></li> <li><a href="/wiki/3%CE%B2-Androstanediol" title="3β-Androstanediol">3β-Androstanediol</a></li> <li><a href="/wiki/4-Androstenediol" title="4-Androstenediol">4-Androstenediol</a></li> <li><a href="/wiki/4-Androstenedione" class="mw-redirect" title="4-Androstenedione">4-Androstenedione</a></li> <li><a href="/wiki/4-Fluoroestradiol" title="4-Fluoroestradiol">4-Fluoroestradiol</a></li> <li><a href="/wiki/4-Hydroxyestradiol" title="4-Hydroxyestradiol">4-Hydroxyestradiol</a></li> <li><a href="/wiki/4-Hydroxyestrone" title="4-Hydroxyestrone">4-Hydroxyestrone</a></li> <li><a href="/wiki/4-Methoxyestradiol" title="4-Methoxyestradiol">4-Methoxyestradiol</a></li> <li><a href="/wiki/4-Methoxyestrone" title="4-Methoxyestrone">4-Methoxyestrone</a></li> <li><a href="/wiki/5-Androstenediol" class="mw-redirect" title="5-Androstenediol">5-Androstenediol</a></li> <li><a href="/wiki/7-Keto-DHEA" title="7-Keto-DHEA">7-Oxo-DHEA</a></li> <li><a href="/wiki/7%CE%B1-Hydroxy-DHEA" title="7α-Hydroxy-DHEA">7α-Hydroxy-DHEA</a></li> <li><a href="/wiki/7%CE%B1-Methylestradiol" title="7α-Methylestradiol">7α-Methylestradiol</a></li> <li><a href="/wiki/7%CE%B2-Hydroxyepiandrosterone" title="7β-Hydroxyepiandrosterone">7β-Hydroxyepiandrosterone</a></li> <li><a href="/wiki/8,9-Dehydroestradiol" title="8,9-Dehydroestradiol">8,9-Dehydroestradiol</a></li> <li><a href="/wiki/8,9-Dehydroestrone" title="8,9-Dehydroestrone">8,9-Dehydroestrone</a></li> <li><a href="/wiki/8%CE%B2-VE2" title="8β-VE2">8β-VE2</a></li> <li><a href="/wiki/10%CE%B2,17%CE%B2-Dihydroxyestra-1,4-dien-3-one" title="10β,17β-Dihydroxyestra-1,4-dien-3-one">10β,17β-Dihydroxyestra-1,4-dien-3-one (DHED)</a></li> <li><a href="/wiki/11%CE%B2-Chloromethylestradiol" title="11β-Chloromethylestradiol">11β-Chloromethylestradiol</a></li> <li><a href="/wiki/11%CE%B2-Methoxyestradiol" title="11β-Methoxyestradiol">11β-Methoxyestradiol</a></li> <li><a href="/wiki/15%CE%B1-Hydroxyestradiol" title="15α-Hydroxyestradiol">15α-Hydroxyestradiol</a></li> <li><a href="/wiki/16-Ketoestradiol" title="16-Ketoestradiol">16-Ketoestradiol</a></li> <li><a href="/wiki/16-Ketoestrone" title="16-Ketoestrone">16-Ketoestrone</a></li> <li><a href="/wiki/16%CE%B1-Fluoroestradiol" class="mw-redirect" title="16α-Fluoroestradiol">16α-Fluoroestradiol</a></li> <li><a href="/wiki/16%CE%B1-Hydroxy-DHEA" title="16α-Hydroxy-DHEA">16α-Hydroxy-DHEA</a></li> <li><a href="/wiki/16%CE%B1-Hydroxyestrone" title="16α-Hydroxyestrone">16α-Hydroxyestrone</a></li> <li><a href="/wiki/16%CE%B1-Iodoestradiol" class="mw-redirect" title="16α-Iodoestradiol">16α-Iodoestradiol</a></li> <li><a href="/wiki/16%CE%B1-LE2" title="16α-LE2">16α-LE2</a></li> <li><a href="/wiki/16%CE%B2-Hydroxyestrone" title="16β-Hydroxyestrone">16β-Hydroxyestrone</a></li> <li><a href="/wiki/16%CE%B2,17%CE%B1-Epiestriol" title="16β,17α-Epiestriol">16β,17α-Epiestriol (16β-hydroxy-17α-estradiol)</a></li> <li><a href="/wiki/17%CE%B1-Estradiol" title="17α-Estradiol">17α-Estradiol</a> (<a href="/wiki/Alfatradiol" title="Alfatradiol">alfatradiol</a>)</li> <li><a href="/wiki/17%CE%B1-Dihydroequilenin" title="17α-Dihydroequilenin">17α-Dihydroequilenin</a></li> <li><a href="/wiki/17%CE%B1-Dihydroequilin" title="17α-Dihydroequilin">17α-Dihydroequilin</a></li> <li><a href="/wiki/17%CE%B1-Epiestriol" title="17α-Epiestriol">17α-Epiestriol (16α-hydroxy-17α-estradiol)</a></li> <li><a href="/wiki/17%CE%B1-Ethynyl-3%CE%B1-androstanediol" title="17α-Ethynyl-3α-androstanediol">17α-Ethynyl-3α-androstanediol</a></li> <li><a href="/wiki/17%CE%B1-Ethynyl-3%CE%B2-androstanediol" title="17α-Ethynyl-3β-androstanediol">17α-Ethynyl-3β-androstanediol</a></li> <li><a href="/wiki/17%CE%B2-Dihydroequilenin" title="17β-Dihydroequilenin">17β-Dihydroequilenin</a></li> <li><a href="/wiki/17%CE%B2-Dihydroequilin" title="17β-Dihydroequilin">17β-Dihydroequilin</a></li> <li><a href="/wiki/17%CE%B2-Methyl-17%CE%B1-dihydroequilenin" title="17β-Methyl-17α-dihydroequilenin">17β-Methyl-17α-dihydroequilenin</a></li> <li><a href="/wiki/Abiraterone" class="mw-redirect" title="Abiraterone">Abiraterone</a></li> <li><a href="/wiki/Abiraterone_acetate" title="Abiraterone acetate">Abiraterone acetate</a></li> <li><a href="/wiki/Alestramustine" title="Alestramustine">Alestramustine</a></li> <li><a href="/wiki/Almestrone" title="Almestrone">Almestrone</a></li> <li><a href="/wiki/Anabolic_steroid" title="Anabolic steroid">Anabolic steroids</a> (e.g., <a href="/wiki/Testosterone" title="Testosterone">testosterone</a> and <a href="/wiki/List_of_androgen_esters#Testosterone_esters" title="List of androgen esters">esters</a>, <a href="/wiki/Methyltestosterone" title="Methyltestosterone">methyltestosterone</a>, <a href="/wiki/Metandienone" title="Metandienone">metandienone (methandrostenolone)</a>, <a href="/wiki/Nandrolone" title="Nandrolone">nandrolone</a> and <a href="/wiki/List_of_androgen_esters#Nandrolone_esters" title="List of androgen esters">esters</a>, many others; via estrogenic metabolites)</li> <li><a href="/wiki/Atrimustine" title="Atrimustine">Atrimustine</a></li> <li><a href="/wiki/Bolandiol" title="Bolandiol">Bolandiol</a></li> <li><a href="/wiki/Bolandiol_dipropionate" title="Bolandiol dipropionate">Bolandiol dipropionate</a></li> <li><a href="/wiki/Butolame" title="Butolame">Butolame</a></li> <li><a href="/wiki/Clomestrone" title="Clomestrone">Clomestrone</a></li> <li><a href="/wiki/Cloxestradiol" title="Cloxestradiol">Cloxestradiol</a> <ul><li><a href="/wiki/Cloxestradiol_acetate" title="Cloxestradiol acetate">Cloxestradiol acetate</a></li></ul></li> <li><a href="/wiki/Conjugated_estriol" title="Conjugated estriol">Conjugated estriol</a></li> <li><a href="/wiki/Conjugated_estrogens" title="Conjugated estrogens">Conjugated estrogens</a></li> <li><a href="/wiki/Cyclodiol" title="Cyclodiol">Cyclodiol</a></li> <li><a href="/wiki/Cyclotriol" title="Cyclotriol">Cyclotriol</a></li> <li><a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone">DHEA</a></li> <li><a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone">DHEA-S</a></li> <li><a href="/wiki/Ent-Estradiol" title="Ent-Estradiol"><i>ent</i>-Estradiol</a></li> <li><a href="/wiki/Epiestriol" title="Epiestriol">Epiestriol (16β-epiestriol, 16β-hydroxy-17β-estradiol)</a></li> <li><a href="/wiki/Epimestrol" title="Epimestrol">Epimestrol</a></li> <li><a href="/wiki/Equilenin" title="Equilenin">Equilenin</a></li> <li><a href="/wiki/Equilin" title="Equilin">Equilin</a></li> <li><a href="/wiki/ERA-63" title="ERA-63">ERA-63 (ORG-37663)</a></li> <li><a href="/wiki/Esterified_estrogens" title="Esterified estrogens">Esterified estrogens</a></li> <li><a href="/wiki/Estetrol" title="Estetrol">Estetrol</a></li> <li><a href="/wiki/Estradiol" title="Estradiol">Estradiol</a> <ul><li><a href="/wiki/List_of_estrogen_esters#Estradiol_esters" title="List of estrogen esters">Estradiol esters</a></li> <li><a href="/wiki/Lipoidal_estradiol" title="Lipoidal estradiol">Lipoidal estradiol</a></li> <li><a href="/wiki/Polyestradiol_phosphate" title="Polyestradiol phosphate">Polyestradiol phosphate</a></li></ul></li> <li><a href="/wiki/Estramustine" title="Estramustine">Estramustine</a></li> <li><a href="/wiki/Estramustine_phosphate" title="Estramustine phosphate">Estramustine phosphate</a></li> <li><a href="/wiki/Estrapronicate" title="Estrapronicate">Estrapronicate</a></li> <li><a href="/wiki/Estrazinol" title="Estrazinol">Estrazinol</a></li> <li><a href="/wiki/Estriol" title="Estriol">Estriol</a> <ul><li><a href="/wiki/List_of_estrogen_esters#Estriol_esters" title="List of estrogen esters">Estriol esters</a></li> <li><a href="/wiki/Polyestriol_phosphate" title="Polyestriol phosphate">Polyestriol phosphate</a></li></ul></li> <li><a href="/wiki/Estrofurate" title="Estrofurate">Estrofurate</a></li> <li><a href="/wiki/Estrogenic_substances" title="Estrogenic substances">Estrogenic substances</a></li> <li><a href="/wiki/Estromustine" title="Estromustine">Estromustine</a></li> <li><a href="/wiki/Estrone" title="Estrone">Estrone</a> <ul><li><a href="/wiki/List_of_estrogen_esters#Estrone_esters" title="List of estrogen esters">Estrone esters</a></li> <li><a href="/wiki/Estrone_methyl_ether" title="Estrone methyl ether">Estrone methyl ether</a></li> <li><a href="/wiki/Estropipate" title="Estropipate">Estropipate</a></li></ul></li> <li><a href="/wiki/Etamestrol" title="Etamestrol">Etamestrol (eptamestrol)</a></li> <li><a href="/wiki/Ethinylandrostenediol" title="Ethinylandrostenediol">Ethinylandrostenediol</a> <ul><li><a href="/wiki/Ethandrostate" title="Ethandrostate">Ethandrostate</a></li></ul></li> <li><a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">Ethinylestradiol</a> <ul><li><a href="/wiki/Ethinylestradiol_3-benzoate" class="mw-redirect" title="Ethinylestradiol 3-benzoate">Ethinylestradiol 3-benzoate</a></li> <li><a href="/wiki/Ethinylestradiol_sulfonate" title="Ethinylestradiol sulfonate">Ethinylestradiol sulfonate</a></li></ul></li> <li><a href="/wiki/Ethinylestriol" title="Ethinylestriol">Ethinylestriol</a></li> <li><a href="/wiki/Ethylestradiol" title="Ethylestradiol">Ethylestradiol</a></li> <li><a href="/wiki/Etynodiol" title="Etynodiol">Etynodiol</a></li> <li><a href="/wiki/Etynodiol_diacetate" title="Etynodiol diacetate">Etynodiol diacetate</a></li> <li><a href="/wiki/Hexolame" title="Hexolame">Hexolame</a></li> <li><a href="/wiki/Hippulin" title="Hippulin">Hippulin</a></li> <li><a href="/wiki/Hydroxyestrone_diacetate" title="Hydroxyestrone diacetate">Hydroxyestrone diacetate</a></li> <li><a href="/wiki/Lynestrenol" title="Lynestrenol">Lynestrenol</a></li> <li><a href="/wiki/Lynestrenol_phenylpropionate" title="Lynestrenol phenylpropionate">Lynestrenol phenylpropionate</a></li> <li><a href="/wiki/Mestranol" title="Mestranol">Mestranol</a></li> <li><a href="/wiki/Methylestradiol" title="Methylestradiol">Methylestradiol</a></li> <li><a href="/wiki/Moxestrol" title="Moxestrol">Moxestrol</a></li> <li><a href="/wiki/Mytatrienediol" title="Mytatrienediol">Mytatrienediol</a></li> <li><a href="/wiki/Nilestriol" title="Nilestriol">Nilestriol</a></li> <li><a href="/wiki/Norethisterone" title="Norethisterone">Norethisterone</a></li> <li><a href="/wiki/Noretynodrel" title="Noretynodrel">Noretynodrel</a></li> <li><a href="/wiki/Orestrate" title="Orestrate">Orestrate</a></li> <li><a href="/wiki/Pentolame" title="Pentolame">Pentolame</a></li> <li><a href="/wiki/Prodiame" title="Prodiame">Prodiame</a></li> <li><a href="/wiki/Prolame" title="Prolame">Prolame</a></li> <li><a href="/wiki/Promestriene" title="Promestriene">Promestriene</a></li> <li><a href="/wiki/RU-16117" title="RU-16117">RU-16117</a></li> <li><a href="/wiki/Quinestradol" title="Quinestradol">Quinestradol</a></li> <li><a href="/wiki/Quinestrol" title="Quinestrol">Quinestrol</a></li> <li><a href="/wiki/Tibolone" title="Tibolone">Tibolone</a></li></ul> <ul><li><i>Nonsteroidal:</i> <a href="/wiki/(R,R)-Tetrahydrochrysene" title="(R,R)-Tetrahydrochrysene">(R,R)-THC</a></li> <li><a href="/wiki/(S,S)-Tetrahydrochrysene" title="(S,S)-Tetrahydrochrysene">(S,S)-THC</a></li> <li><a href="/wiki/2,8-Dihydroxyhexahydrochrysene" title="2,8-Dihydroxyhexahydrochrysene">2,8-DHHHC</a></li> <li><a href="/w/index.php?title=%CE%92-LGND1&action=edit&redlink=1" class="new" title="Β-LGND1 (page does not exist)">β-LGND1</a></li> <li><a href="/wiki/%CE%92-LGND2" title="Β-LGND2">β-LGND2 (GTx-878)</a></li> <li><a href="/w/index.php?title=AC-186&action=edit&redlink=1" class="new" title="AC-186 (page does not exist)">AC-186</a></li> <li><a href="/wiki/Allenestrol" title="Allenestrol">Allenestrol</a></li> <li><a href="/wiki/Allenolic_acid" title="Allenolic acid">Allenolic acid</a></li> <li><a href="/wiki/Benzestrol" title="Benzestrol">Benzestrol</a></li> <li><a href="/wiki/Bifluranol" title="Bifluranol">Bifluranol</a></li> <li><a href="/wiki/Bisdehydrodoisynolic_acid" title="Bisdehydrodoisynolic acid">Bisdehydrodoisynolic acid</a></li> <li><a href="/wiki/Butestrol" title="Butestrol">Butestrol</a></li> <li><a href="/wiki/Carbestrol" title="Carbestrol">Carbestrol</a></li> <li><a href="/wiki/D-15414" title="D-15414">D-15414</a></li> <li><a href="/wiki/DCW234" title="DCW234">DCW234</a></li> <li><a href="/wiki/Diarylpropionitrile" title="Diarylpropionitrile">Diarylpropionitrile</a></li> <li><a href="/wiki/Dienestrol" title="Dienestrol">Dienestrol</a> <ul><li><a href="/wiki/Dienestrol_diacetate" title="Dienestrol diacetate">Dienestrol diacetate</a></li></ul></li> <li><a href="/wiki/Diethylstilbestrol" title="Diethylstilbestrol">Diethylstilbestrol</a> <ul><li><a href="/wiki/List_of_estrogen_esters#Diethylstilbestrol_esters" title="List of estrogen esters">Diethylstilbestrol esters</a></li></ul></li> <li><a href="/wiki/Dimestrol" title="Dimestrol">Dimestrol (dianisylhexene)</a></li> <li><a href="/wiki/Dimethylstilbestrol" title="Dimethylstilbestrol">Dimethylstilbestrol</a></li> <li><a href="/wiki/Doisynoestrol" title="Doisynoestrol">Doisynoestrol (fenocycline)</a></li> <li><a href="/wiki/Doisynolic_acid" title="Doisynolic acid">Doisynolic acid</a></li> <li><a href="/wiki/Efavirenz" title="Efavirenz">Efavirenz</a></li> <li><a href="/wiki/Elacestrant" title="Elacestrant">Elacestrant</a></li> <li><a href="/wiki/ERB-196" title="ERB-196">ERB-196 (WAY-202196)</a></li> <li><a href="/wiki/Erteberel" title="Erteberel">Erteberel (SERBA-1, LY-500307)</a></li> <li><a href="/wiki/Estrobin" title="Estrobin">Estrobin (DBE)</a></li> <li><a href="/wiki/Fenestrel" title="Fenestrel">Fenestrel</a></li> <li><a href="/wiki/FERb_033" title="FERb 033">FERb 033</a></li> <li><a href="/wiki/Fosfestrol" title="Fosfestrol">Fosfestrol (diethylstilbestrol diphosphate)</a></li> <li><a href="/wiki/Furostilbestrol" title="Furostilbestrol">Furostilbestrol (diethylstilbestrol difuroate)</a></li> <li><a href="/wiki/GTx-758" title="GTx-758">GTx-758</a></li> <li><a href="/wiki/Hexestrol" title="Hexestrol">Hexestrol</a> <ul><li><a href="/wiki/List_of_estrogen_esters#Hexestrol_esters" title="List of estrogen esters">Hexestrol esters</a></li></ul></li> <li><a href="/wiki/ICI-85966" title="ICI-85966">ICI-85966 (Stilbostat)</a></li> <li><a href="/wiki/M2613" title="M2613">M2613</a></li> <li><a href="/wiki/Meso-Butestrol" title="Meso-Butestrol"><i>meso</i>-Butestrol</a></li> <li><a href="/wiki/Meso-Hexestrol" class="mw-redirect" title="Meso-Hexestrol"><i>meso</i>-Hexestrol</a></li> <li><a href="/wiki/Mestilbol" title="Mestilbol">Mestilbol</a></li> <li><a href="/wiki/Methallenestril" title="Methallenestril">Methallenestril</a></li> <li><a href="/wiki/Methestrol" title="Methestrol">Methestrol</a></li> <li><a href="/wiki/Methestrol_dipropionate" title="Methestrol dipropionate">Methestrol dipropionate</a></li> <li><a href="/wiki/Paroxypropione" title="Paroxypropione">Paroxypropione</a></li> <li><a href="/wiki/Pentafluranol" title="Pentafluranol">Pentafluranol</a></li> <li><a href="/wiki/Phenestrol" title="Phenestrol">Phenestrol</a></li> <li><a href="/wiki/Prinaberel" title="Prinaberel">Prinaberel (ERB-041, WAY-202041)</a></li> <li><a href="/wiki/Propylpyrazoletriol" title="Propylpyrazoletriol">Propylpyrazoletriol</a></li> <li><a href="/wiki/Quadrosilan" title="Quadrosilan">Quadrosilan</a></li> <li><a href="/w/index.php?title=SC-3296&action=edit&redlink=1" class="new" title="SC-3296 (page does not exist)">SC-3296</a></li> <li><a href="/wiki/SC-4289" title="SC-4289">SC-4289</a></li> <li><a href="/wiki/SERBA-2" title="SERBA-2">SERBA-2</a></li> <li><a href="/wiki/SKF-82,958" title="SKF-82,958">SKF-82,958</a></li> <li><a href="/wiki/Terfluranol" title="Terfluranol">Terfluranol</a></li> <li><a href="/wiki/Triphenylbromoethylene" title="Triphenylbromoethylene">Triphenylbromoethylene</a></li> <li><a href="/wiki/Triphenylchloroethylene" title="Triphenylchloroethylene">Triphenylchloroethylene</a></li> <li><a href="/wiki/Triphenyliodoethylene" title="Triphenyliodoethylene">Triphenyliodoethylene</a></li> <li><a href="/wiki/Triphenylmethylethylene" title="Triphenylmethylethylene">Triphenylmethylethylene (triphenylpropene)</a></li> <li><a href="/wiki/WAY-166818" title="WAY-166818">WAY-166818</a></li> <li><a href="/w/index.php?title=WAY-169916&action=edit&redlink=1" class="new" title="WAY-169916 (page does not exist)">WAY-169916</a></li> <li><a href="/wiki/WAY-200070" title="WAY-200070">WAY-200070</a></li> <li><a href="/wiki/WAY-204688" title="WAY-204688">WAY-204688 (SIM-688)</a></li> <li><a href="/wiki/WAY-214156" title="WAY-214156">WAY-214156</a></li></ul> <ul><li><i>Unknown/unsorted:</i> <a href="/wiki/ERB-26" title="ERB-26">ERB-26</a></li> <li><a href="/wiki/ERA-45" title="ERA-45">ERA-45</a></li> <li><a href="/wiki/ERB-79" title="ERB-79">ERB-79</a></li> <li><a href="/wiki/ZK-283197" title="ZK-283197">ZK-283197</a></li></ul> <ul><li><i>Xenoestrogens:</i> <a href="/wiki/Anise" title="Anise">Anise</a>-related (e.g., <a class="mw-selflink selflink">anethole</a>, <a href="/wiki/Anol" title="Anol">anol</a>, <a href="/wiki/Dianethole" title="Dianethole">dianethole</a>, <a href="/wiki/Dianol" title="Dianol">dianol</a>, <a href="/wiki/Photoanethole" title="Photoanethole">photoanethole</a>)</li> <li><a href="/wiki/Chalconoid" title="Chalconoid">Chalconoids</a> (e.g., <a href="/wiki/Isoliquiritigenin" title="Isoliquiritigenin">isoliquiritigenin</a>, <a href="/wiki/Phloretin" title="Phloretin">phloretin</a>, <a href="/wiki/Phlorizin" title="Phlorizin">phlorizin (phloridzin)</a>, <a href="/wiki/Wedelolactone" title="Wedelolactone">wedelolactone</a>)</li> <li><a href="/wiki/Coumestan" title="Coumestan">Coumestans</a> (e.g., <a href="/wiki/Coumestrol" title="Coumestrol">coumestrol</a>, <a href="/wiki/Psoralidin" title="Psoralidin">psoralidin</a>)</li> <li><a href="/wiki/Flavonoid" title="Flavonoid">Flavonoids</a> (incl. <a href="/wiki/7,8-Dihydroxyflavone" class="mw-redirect" title="7,8-Dihydroxyflavone">7,8-DHF</a>, <a href="/wiki/8-Prenylnaringenin" title="8-Prenylnaringenin">8-prenylnaringenin</a>, <a href="/wiki/Apigenin" title="Apigenin">apigenin</a>, <a href="/wiki/Baicalein" title="Baicalein">baicalein</a>, <a href="/wiki/Baicalin" title="Baicalin">baicalin</a>, <a href="/wiki/Biochanin_A" title="Biochanin A">biochanin A</a>, <a href="/wiki/Calycosin" title="Calycosin">calycosin</a>, <a href="/wiki/Catechin" title="Catechin">catechin</a>, <a href="/wiki/Daidzein" title="Daidzein">daidzein</a>, <a href="/wiki/Daidzin" title="Daidzin">daidzin</a>, <a href="/wiki/Epicatechin_gallate" title="Epicatechin gallate">ECG</a>, <a href="/wiki/Epigallocatechin_gallate" title="Epigallocatechin gallate">EGCG</a>, <a href="/wiki/Epicatechin" class="mw-redirect" title="Epicatechin">epicatechin</a>, <a href="/wiki/Equol" title="Equol">equol</a>, <a href="/wiki/Formononetin" title="Formononetin">formononetin</a>, <a href="/wiki/Glabrene" title="Glabrene">glabrene</a>, <a href="/wiki/Glabridin" title="Glabridin">glabridin</a>, <a href="/wiki/Genistein" title="Genistein">genistein</a>, <a href="/wiki/Genistin" title="Genistin">genistin</a>, <a href="/wiki/Glycitein" title="Glycitein">glycitein</a>, <a href="/wiki/Kaempferol" title="Kaempferol">kaempferol</a>, <a href="/wiki/Liquiritigenin" title="Liquiritigenin">liquiritigenin</a>, <a href="/wiki/Mirificin" title="Mirificin">mirificin</a>, <a href="/wiki/Myricetin" title="Myricetin">myricetin</a>, <a href="/wiki/Naringenin" title="Naringenin">naringenin</a>, <a href="/w/index.php?title=Penduletin&action=edit&redlink=1" class="new" title="Penduletin (page does not exist)">penduletin</a>, <a href="/wiki/Pinocembrin" title="Pinocembrin">pinocembrin</a>, <a href="/wiki/Prunetin" title="Prunetin">prunetin</a>, <a href="/wiki/Puerarin" title="Puerarin">puerarin</a>, <a href="/wiki/Quercetin" title="Quercetin">quercetin</a>, <a href="/wiki/Tectoridin" title="Tectoridin">tectoridin</a>, <a href="/wiki/Tectorigenin" title="Tectorigenin">tectorigenin</a>)</li> <li><a href="/wiki/Lavender_oil" title="Lavender oil">Lavender oil</a></li> <li><a href="/wiki/Lignan" title="Lignan">Lignans</a> (e.g., <a href="/wiki/Enterodiol" title="Enterodiol">enterodiol</a>, <a href="/wiki/Enterolactone" title="Enterolactone">enterolactone</a>, <a href="/wiki/Nyasol" title="Nyasol">nyasol (<i>cis</i>-hinokiresinol)</a>)</li> <li><a href="/wiki/Metalloestrogen" title="Metalloestrogen">Metalloestrogens</a> (e.g., <a href="/wiki/Cadmium" title="Cadmium">cadmium</a>)</li> <li><a href="/wiki/Pesticide" title="Pesticide">Pesticides</a> (e.g., <a href="/wiki/Alternariol" title="Alternariol">alternariol</a>, <a href="/wiki/Dieldrin" title="Dieldrin">dieldrin</a>, <a href="/wiki/Endosulfan" title="Endosulfan">endosulfan</a>, <a href="/wiki/Fenarimol" title="Fenarimol">fenarimol</a>, <a href="/wiki/HPTE" title="HPTE">HPTE</a>, <a href="/wiki/Methiocarb" title="Methiocarb">methiocarb</a>, <a href="/wiki/Methoxychlor" title="Methoxychlor">methoxychlor</a>, <a href="/wiki/Triclocarban" title="Triclocarban">triclocarban</a>, <a href="/wiki/Triclosan" title="Triclosan">triclosan</a>)</li> <li><a href="/wiki/Phytosteroid" title="Phytosteroid">Phytosteroids</a> (e.g., <a href="/wiki/Digitoxin" title="Digitoxin">digitoxin</a> (<a href="/wiki/Digitalis" title="Digitalis">digitalis</a>), <a href="/wiki/Diosgenin" title="Diosgenin">diosgenin</a>, <a href="/wiki/Guggulsterone" title="Guggulsterone">guggulsterone</a>)</li> <li><a href="/wiki/Phytosterol" title="Phytosterol">Phytosterols</a> (e.g., <a href="/wiki/%CE%92-sitosterol" class="mw-redirect" title="Β-sitosterol">β-sitosterol</a>, <a href="/wiki/Campesterol" title="Campesterol">campesterol</a>, <a href="/wiki/Stigmasterol" title="Stigmasterol">stigmasterol</a>)</li> <li><a href="/wiki/Resorcylic_acid_lactone" title="Resorcylic acid lactone">Resorcylic acid lactones</a> (e.g., <a href="/wiki/Zearalanone" title="Zearalanone">zearalanone</a>, <a href="/wiki/%CE%91-zearalenol" class="mw-redirect" title="Α-zearalenol">α-zearalenol</a>, <a href="/wiki/%CE%92-zearalenol" class="mw-redirect" title="Β-zearalenol">β-zearalenol</a>, <a href="/wiki/Zearalenone" title="Zearalenone">zearalenone</a>, <a href="/wiki/Zeranol" title="Zeranol">zeranol (α-zearalanol)</a>, <a href="/wiki/Taleranol" title="Taleranol">taleranol (teranol, β-zearalanol)</a>)</li> <li><a href="/wiki/Steroid" title="Steroid">Steroid</a>-like (e.g., <a href="/wiki/Deoxymiroestrol" class="mw-redirect" title="Deoxymiroestrol">deoxymiroestrol</a>, <a href="/wiki/Miroestrol" title="Miroestrol">miroestrol</a>)</li> <li><a href="/wiki/Stilbenoid" title="Stilbenoid">Stilbenoids</a> (e.g., <a href="/wiki/Resveratrol" title="Resveratrol">resveratrol</a>, <a href="/wiki/Rhaponticin" title="Rhaponticin">rhaponticin</a>)</li> <li><a href="/wiki/Synthetic_xenoestrogen" class="mw-redirect" title="Synthetic xenoestrogen">Synthetic xenoestrogens</a> (e.g., <a href="/wiki/Alkylphenol" title="Alkylphenol">alkylphenols</a>, <a href="/wiki/Bisphenol" title="Bisphenol">bisphenols</a> (e.g., <a href="/wiki/Bisphenol_A" title="Bisphenol A">BPA</a>, <a href="/wiki/Bisphenol_F" title="Bisphenol F">BPF</a>, <a href="/wiki/Bisphenol_S" title="Bisphenol S">BPS</a>), <a href="/wiki/Dichlorodiphenyltrichloroethane" class="mw-redirect" title="Dichlorodiphenyltrichloroethane">DDT</a>, <a href="/wiki/Paraben" title="Paraben">parabens</a>, <a href="/wiki/Polybrominated_biphenyl" title="Polybrominated biphenyl">PBBs</a>, <a href="/wiki/4-hydroxybenzoic_acid" class="mw-redirect" title="4-hydroxybenzoic acid">PHBA</a>, <a href="/wiki/Phthalate" class="mw-redirect" title="Phthalate">phthalates</a>, <a href="/wiki/Polychlorinated_biphenyl" title="Polychlorinated biphenyl">PCBs</a>)</li> <li>Others (e.g., <a href="/wiki/Agnuside" title="Agnuside">agnuside</a>, <a href="/w/index.php?title=Rotundifuran&action=edit&redlink=1" class="new" title="Rotundifuran (page does not exist)">rotundifuran</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Mixed<br />(<a href="/wiki/Selective_estrogen_receptor_modulators" class="mw-redirect" title="Selective estrogen receptor modulators"><abbr title="Selective estrogen receptor modulators">SERMs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Selective estrogen receptor modulators</span>)</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2-Phenylbenzofuran" title="2-Phenylbenzofuran">2-Phenylbenzofuran</a></li> <li><a href="/w/index.php?title=2-Phenylbenzothiophene&action=edit&redlink=1" class="new" title="2-Phenylbenzothiophene (page does not exist)">2-Phenylbenzothiophene</a></li> <li><a href="/wiki/4%27-Hydroxynorendoxifen" title="4'-Hydroxynorendoxifen">4'-Hydroxynorendoxifen</a></li> <li><a href="/wiki/27-Hydroxycholesterol" title="27-Hydroxycholesterol">27-Hydroxycholesterol</a></li> <li><a href="/wiki/Acefluranol" title="Acefluranol">Acefluranol</a></li> <li><a href="/wiki/Acolbifene" title="Acolbifene">Acolbifene</a></li> <li><a href="/wiki/Afimoxifene" title="Afimoxifene">Afimoxifene</a></li> <li><a href="/wiki/Anordiol" title="Anordiol">Anordiol</a></li> <li><a href="/wiki/Anordrin" title="Anordrin">Anordrin</a></li> <li><a href="/wiki/Arzoxifene" title="Arzoxifene">Arzoxifene</a></li> <li><a href="/wiki/Bazedoxifene" title="Bazedoxifene">Bazedoxifene</a></li> <li><a href="/wiki/Brilanestrant" title="Brilanestrant">Brilanestrant</a></li> <li><a href="/wiki/Broparestrol" title="Broparestrol">Broparestrol</a></li> <li><a href="/wiki/Camizestrant" title="Camizestrant">Camizestrant</a></li> <li><a href="/wiki/Chlorotrianisene" title="Chlorotrianisene">Chlorotrianisene</a></li> <li><a href="/wiki/Clomifene" title="Clomifene">Clomifene</a></li> <li><a href="/wiki/Clomifenoxide" title="Clomifenoxide">Clomifenoxide</a></li> <li><a href="/w/index.php?title=CN-55945-27&action=edit&redlink=1" class="new" title="CN-55945-27 (page does not exist)">CN-55945-27</a></li> <li><a href="/wiki/Cyclofenil" title="Cyclofenil">Cyclofenil</a></li> <li><a href="/w/index.php?title=D-15413&action=edit&redlink=1" class="new" title="D-15413 (page does not exist)">D-15413</a></li> <li><a href="/wiki/Desmethylchlorotrianisene" title="Desmethylchlorotrianisene">Desmethylchlorotrianisene</a></li> <li><a href="/wiki/Droloxifene" title="Droloxifene">Droloxifene</a></li> <li><a href="/wiki/Enclomifene" title="Enclomifene">Enclomifene</a></li> <li><a href="/wiki/Endoxifen" title="Endoxifen">Endoxifen</a></li> <li><a href="/wiki/Etacstil" title="Etacstil">Etacstil (GW-5638, DPC-974)</a></li> <li><a href="/wiki/Ethamoxytriphetol" title="Ethamoxytriphetol">Ethamoxytriphetol (MER-25)</a></li> <li><a href="/wiki/Femarelle" title="Femarelle">Femarelle</a></li> <li><a href="/wiki/Fispemifene" title="Fispemifene">Fispemifene</a></li> <li><a href="/w/index.php?title=GW-7604&action=edit&redlink=1" class="new" title="GW-7604 (page does not exist)">GW-7604</a></li> <li><a href="/wiki/ICI-55548" class="mw-redirect" title="ICI-55548">ICI-55548</a></li> <li><a href="/wiki/Idoxifene" title="Idoxifene">Idoxifene</a></li> <li><a href="/wiki/Lasofoxifene" title="Lasofoxifene">Lasofoxifene</a></li> <li><a href="/wiki/Levormeloxifene" title="Levormeloxifene">Levormeloxifene</a></li> <li><a href="/wiki/LN-1643" class="mw-redirect" title="LN-1643">LN-1643</a></li> <li><a href="/wiki/LN-2299" class="mw-redirect" title="LN-2299">LN-2299</a></li> <li><a href="/w/index.php?title=LY-117018&action=edit&redlink=1" class="new" title="LY-117018 (page does not exist)">LY-117018</a></li> <li><a href="/wiki/Menerba" title="Menerba">Menerba</a></li> <li><a href="/wiki/Miproxifene" title="Miproxifene">Miproxifene</a></li> <li><a href="/wiki/Miproxifene_phosphate" title="Miproxifene phosphate">Miproxifene phosphate</a></li> <li><a href="/w/index.php?title=MRL-37&action=edit&redlink=1" class="new" title="MRL-37 (page does not exist)">MRL-37</a></li> <li><a href="/wiki/Nafoxidine" title="Nafoxidine">Nafoxidine</a></li> <li><a href="/wiki/Nitromifene" title="Nitromifene">Nitromifene</a></li> <li><a href="/wiki/NNC_45-0095" title="NNC 45-0095">NNC 45-0095</a></li> <li><a href="/w/index.php?title=NNC_45-0320&action=edit&redlink=1" class="new" title="NNC 45-0320 (page does not exist)">NNC 45-0320</a></li> <li><a href="/w/index.php?title=NNC_45-0781&action=edit&redlink=1" class="new" title="NNC 45-0781 (page does not exist)">NNC 45-0781</a></li> <li><a href="/w/index.php?title=NNC_45-1506&action=edit&redlink=1" class="new" title="NNC 45-1506 (page does not exist)">NNC 45-1506</a></li> <li><a href="/wiki/Ormeloxifene" title="Ormeloxifene">Ormeloxifene</a></li> <li><a href="/wiki/Ospemifene" title="Ospemifene">Ospemifene</a></li> <li><a href="/wiki/Panomifene" title="Panomifene">Panomifene</a></li> <li><a href="/wiki/Pipendoxifene" title="Pipendoxifene">Pipendoxifene</a></li> <li><a href="/w/index.php?title=Promensil&action=edit&redlink=1" class="new" title="Promensil (page does not exist)">Promensil</a></li> <li><a href="/wiki/Raloxifene" title="Raloxifene">Raloxifene</a></li> <li><a href="/wiki/Rimostil" title="Rimostil">Rimostil (P-081)</a></li> <li><a href="/wiki/Spironolactone" title="Spironolactone">Spironolactone</a></li> <li><a href="/w/index.php?title=SS1010&action=edit&redlink=1" class="new" title="SS1010 (page does not exist)">SS1010</a></li> <li><a href="/wiki/Tamoxifen" title="Tamoxifen">Tamoxifen</a></li> <li><a href="/wiki/TAS-108" title="TAS-108">TAS-108 (SR-16234)</a></li> <li><a href="/wiki/Toremifene" title="Toremifene">Toremifene</a></li> <li><a href="/wiki/Trioxifene" title="Trioxifene">Trioxifene</a></li> <li><a href="/w/index.php?title=TZE-5323&action=edit&redlink=1" class="new" title="TZE-5323 (page does not exist)">TZE-5323</a></li> <li><a href="/w/index.php?title=U-11555A&action=edit&redlink=1" class="new" title="U-11555A (page does not exist)">U-11555A</a></li> <li><a href="/w/index.php?title=U-11634&action=edit&redlink=1" class="new" title="U-11634 (page does not exist)">U-11634</a></li> <li><a href="/w/index.php?title=Y-134&action=edit&redlink=1" class="new" title="Y-134 (page does not exist)">Y-134</a></li> <li><a href="/wiki/Zindoxifene" title="Zindoxifene">Zindoxifene</a></li> <li><a href="/wiki/Zuclomifene" title="Zuclomifene">Zuclomifene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Antagonists</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/(R,R)-Tetrahydrochrysene" title="(R,R)-Tetrahydrochrysene">(R,R)-THC</a></li> <li><a href="/wiki/7%CE%B2-Hydroxy-DHEA" title="7β-Hydroxy-DHEA">7β-Hydroxy-DHEA</a></li> <li><a href="/w/index.php?title=Chloroindazole&action=edit&redlink=1" class="new" title="Chloroindazole (page does not exist)">Chloroindazole</a></li> <li><a href="/wiki/Cytestrol_acetate" title="Cytestrol acetate">Cytestrol acetate</a></li> <li><a href="/w/index.php?title=EM-800&action=edit&redlink=1" class="new" title="EM-800 (page does not exist)">EM-800 (SCH-57050)</a></li> <li><a href="/wiki/Epitiostanol" title="Epitiostanol">Epitiostanol</a></li> <li><a href="/w/index.php?title=ERA-90&action=edit&redlink=1" class="new" title="ERA-90 (page does not exist)">ERA-90</a></li> <li><a href="/w/index.php?title=ERB-88&action=edit&redlink=1" class="new" title="ERB-88 (page does not exist)">ERB-88</a></li> <li><a href="/wiki/Fulvestrant" title="Fulvestrant">Fulvestrant (ICI-182780)</a></li> <li><a href="/wiki/Glyceollin" title="Glyceollin">Glyceollins</a> (<a href="/wiki/Glyceollin_I" title="Glyceollin I">I</a>, <a href="/w/index.php?title=Glyceollin_II&action=edit&redlink=1" class="new" title="Glyceollin II (page does not exist)">II</a>, <a href="/wiki/Glyceollin_III" title="Glyceollin III">III</a>, <a href="/w/index.php?title=Glyceollin_IV&action=edit&redlink=1" class="new" title="Glyceollin IV (page does not exist)">IV</a>)</li> <li><a href="/wiki/ICI-164384" title="ICI-164384">ICI-164384</a></li> <li><a href="/w/index.php?title=MDL-101906&action=edit&redlink=1" class="new" title="MDL-101906 (page does not exist)">MDL-101906</a></li> <li><a href="/wiki/Mepitiostane" title="Mepitiostane">Mepitiostane</a></li> <li><a href="/wiki/Methylepitiostanol" title="Methylepitiostanol">Methylepitiostanol</a></li> <li><a href="/wiki/Methylpiperidinopyrazole" title="Methylpiperidinopyrazole">Methylpiperidinopyrazole</a></li> <li><a href="/wiki/MIBE" title="MIBE">MIBE</a></li> <li><a href="/w/index.php?title=Oxabicycloheptene_sulfonate&action=edit&redlink=1" class="new" title="Oxabicycloheptene sulfonate (page does not exist)">Oxabicycloheptene sulfonate</a></li> <li><a href="/wiki/Phenytoin" title="Phenytoin">Phenytoin</a></li> <li><a href="/wiki/PHTPP" title="PHTPP">PHTPP</a></li> <li><a href="/wiki/Prochloraz" title="Prochloraz">Prochloraz</a></li> <li><a href="/w/index.php?title=RU-39411&action=edit&redlink=1" class="new" title="RU-39411 (page does not exist)">RU-39411</a></li> <li><a href="/w/index.php?title=RU-58668&action=edit&redlink=1" class="new" title="RU-58668 (page does not exist)">RU-58668</a></li> <li><a href="/w/index.php?title=SS1020&action=edit&redlink=1" class="new" title="SS1020 (page does not exist)">SS1020</a></li> <li><a href="/wiki/TAS-108" title="TAS-108">TAS-108 (SR-16234)</a></li> <li><a href="/wiki/ZB716" title="ZB716">ZB716</a></li> <li><a href="/w/index.php?title=ZK-164015&action=edit&redlink=1" class="new" title="ZK-164015 (page does not exist)">ZK-164015</a></li> <li><a href="/w/index.php?title=ZK-191703&action=edit&redlink=1" class="new" title="ZK-191703 (page does not exist)">ZK-191703</a></li></ul> <ul><li><i>Coregulator-binding modulators:</i> <a href="/wiki/ERX-11" title="ERX-11">ERX-11</a></li></ul> <ul><li><i>Noncompetitive inhibitors:</i> <a href="/wiki/Trilostane" title="Trilostane">Trilostane</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/G_protein-coupled_estrogen_receptor" class="mw-redirect" title="G protein-coupled estrogen receptor"><abbr title="G protein-coupled estrogen receptor">GPER</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip G protein-coupled estrogen receptor</span></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:6em;;text-align:center">Agonists</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2-Methoxyestradiol" title="2-Methoxyestradiol">2-Methoxyestradiol</a></li> <li><a href="/wiki/7%CE%B2-Hydroxyepiandrosterone" title="7β-Hydroxyepiandrosterone">7β-Hydroxyepiandrosterone</a></li> <li><a href="/wiki/Afimoxifene" title="Afimoxifene">Afimoxifene (4-hydroxytamoxifen)</a></li> <li><a href="/wiki/Aldosterone" title="Aldosterone">Aldosterone</a></li> <li><a href="/wiki/Atrazine" title="Atrazine">Atrazine</a></li> <li><a href="/wiki/Bisphenol_A" title="Bisphenol A">Bisphenol A</a></li> <li><a href="/wiki/Daidzein" title="Daidzein">Daidzein</a></li> <li><a href="/wiki/DDT" title="DDT">DDT</a> (<a href="/wiki/P,p%27-DDT" class="mw-redirect" title="P,p'-DDT">p,p'-DDT</a>, <a href="/w/index.php?title=O%27,p%27-DDE&action=edit&redlink=1" class="new" title="O',p'-DDE (page does not exist)">o',p'-DDE</a>)</li> <li><a href="/wiki/Diarylpropionitrile" title="Diarylpropionitrile">Diarylpropionitrile</a></li> <li><a href="/wiki/Equol" title="Equol">Equol</a></li> <li><a href="/wiki/Estradiol" title="Estradiol">Estradiol</a></li> <li><a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">Ethinylestradiol</a></li> <li><a href="/wiki/Fulvestrant" title="Fulvestrant">Fulvestrant (ICI-182780)</a></li> <li><a href="/w/index.php?title=G-1_(drug)&action=edit&redlink=1" class="new" title="G-1 (drug) (page does not exist)">G-1</a></li> <li><a href="/wiki/Genistein" title="Genistein">Genistein</a></li> <li><a href="/w/index.php?title=GPER-L1&action=edit&redlink=1" class="new" title="GPER-L1 (page does not exist)">GPER-L1</a></li> <li><a href="/w/index.php?title=GPER-L2&action=edit&redlink=1" class="new" title="GPER-L2 (page does not exist)">GPER-L2</a></li> <li><a href="/wiki/Hydroxytyrosol" title="Hydroxytyrosol">Hydroxytyrosol</a></li> <li><a href="/wiki/Kepone" class="mw-redirect" title="Kepone">Kepone</a></li> <li><a href="/wiki/Niacin" title="Niacin">Niacin</a></li> <li><a href="/wiki/Niacinamide" class="mw-redirect" title="Niacinamide">Niacinamide</a></li> <li><a href="/wiki/Nonylphenol" title="Nonylphenol">Nonylphenol</a></li> <li><a href="/wiki/Oleuropein" title="Oleuropein">Oleuropein</a></li> <li><a href="/wiki/Polychlorinated_biphenyl" title="Polychlorinated biphenyl">PCBs</a> (<a href="/w/index.php?title=2,2%27,5%27-PCB-4-OH&action=edit&redlink=1" class="new" title="2,2',5'-PCB-4-OH (page does not exist)">2,2',5'-PCB-4-OH</a>)</li> <li><a href="/wiki/Propylpyrazoletriol" title="Propylpyrazoletriol">Propylpyrazoletriol</a></li> <li><a href="/wiki/Quercetin" title="Quercetin">Quercetin</a></li> <li><a href="/wiki/Raloxifene" title="Raloxifene">Raloxifene</a></li> <li><a href="/wiki/Resveratrol" title="Resveratrol">Resveratrol</a></li> <li><a href="/w/index.php?title=STX_(drug)&action=edit&redlink=1" class="new" title="STX (drug) (page does not exist)">STX</a></li> <li><a href="/wiki/Tamoxifen" title="Tamoxifen">Tamoxifen</a></li> <li><a href="/wiki/Tectoridin" title="Tectoridin">Tectoridin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Antagonists</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/CCL18" title="CCL18">CCL18</a></li> <li><a href="/wiki/Estriol" title="Estriol">Estriol</a></li> <li><a href="/w/index.php?title=G-15_(drug)&action=edit&redlink=1" class="new" title="G-15 (drug) (page does not exist)">G-15</a></li> <li><a href="/w/index.php?title=G-36_(drug)&action=edit&redlink=1" class="new" title="G-36 (drug) (page does not exist)">G-36</a></li> <li><a href="/wiki/MIBE" title="MIBE">MIBE</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Unknown</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Diethylstilbestrol" title="Diethylstilbestrol">Diethylstilbestrol</a></li> <li><a href="/wiki/Zearalenone" title="Zearalenone">Zearalenone</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt>See also</dt> <dd><a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></dd> <dd><a href="/wiki/Template:Estrogens_and_antiestrogens" title="Template:Estrogens and antiestrogens">Estrogens and antiestrogens</a></dd> <dd><a href="/wiki/Template:Androgen_receptor_modulators" title="Template:Androgen receptor modulators">Androgen receptor modulators</a></dd> <dd><a href="/wiki/Template:Progesterone_receptor_modulators" title="Template:Progesterone receptor modulators">Progesterone receptor modulators</a></dd> <dd><a href="/wiki/List_of_steroidal_estrogens" class="mw-redirect" title="List of steroidal estrogens">List of estrogens</a></dd></dl> </div></td></tr></tbody></table></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?type=1x1" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Retrieved from "<a dir="ltr" href="https://en.wikipedia.org/w/index.php?title=Anethole&oldid=1250017114">https://en.wikipedia.org/w/index.php?title=Anethole&oldid=1250017114</a>"</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div id="mw-normal-catlinks" class="mw-normal-catlinks"><a href="/wiki/Help:Category" title="Help:Category">Categories</a>: <ul><li><a href="/wiki/Category:Flavors" title="Category:Flavors">Flavors</a></li><li><a href="/wiki/Category:Sugar_substitutes" title="Category:Sugar substitutes">Sugar substitutes</a></li><li><a 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