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</a> <ul id="toc-Uses_and_reactions-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Dietary_sources" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Dietary_sources"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Dietary sources</span> </div> </a> <button aria-controls="toc-Dietary_sources-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 Dietary sources subsection</span> </button> <ul id="toc-Dietary_sources-sublist" class="vector-toc-list"> <li id="toc-Other_occurrences" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Other_occurrences"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.1</span> <span>Other occurrences</span> </div> </a> <ul id="toc-Other_occurrences-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Health_effects" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Health_effects"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Health effects</span> </div> </a> <ul id="toc-Health_effects-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-Further_reading" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Further_reading"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>Further reading</span> </div> </a> <ul id="toc-Further_reading-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">9</span> <span>External links</span> </div> </a> <ul id="toc-External_links-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span class="vector-dropdown-label-text">Toggle the table of contents</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Linoleic acid</span></h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="Go to an article in another language. Available in 42 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-42" 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">42 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%AD%D9%85%D8%B6_%D8%A7%D9%84%D9%84%D9%8A%D9%86%D9%88%D9%84%D9%8A%D9%8A%D9%83" title="حمض اللينولييك – Arabic" lang="ar" hreflang="ar" data-title="حمض اللينولييك" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D8%A7%D8%B3%DB%8C%D8%AF_%D9%84%DB%8C%D9%86%D9%88%D9%84%D8%A6%DB%8C%DA%A9" title="اسید لینولئیک – South Azerbaijani" lang="azb" hreflang="azb" data-title="اسید لینولئیک" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-be mw-list-item"><a href="https://be.wikipedia.org/wiki/%D0%9B%D1%96%D0%BD%D0%BE%D0%BB%D0%B5%D0%B2%D0%B0%D1%8F_%D0%BA%D1%96%D1%81%D0%BB%D0%B0%D1%82%D0%B0" title="Лінолевая кіслата – Belarusian" lang="be" hreflang="be" data-title="Лінолевая кіслата" data-language-autonym="Беларуская" data-language-local-name="Belarusian" class="interlanguage-link-target"><span>Беларуская</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/%C3%80cid_linoleic" title="Àcid linoleic – Catalan" lang="ca" hreflang="ca" data-title="Àcid linoleic" 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/Kyselina_linolov%C3%A1" title="Kyselina linolová – Czech" lang="cs" hreflang="cs" data-title="Kyselina linolová" 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/Linolsyre" title="Linolsyre – Danish" lang="da" hreflang="da" data-title="Linolsyre" 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/Linols%C3%A4ure" title="Linolsäure – German" lang="de" hreflang="de" data-title="Linolsäure" 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%9B%CE%B9%CE%BD%CE%B5%CE%BB%CE%B1%CF%8A%CE%BA%CF%8C_%CE%BF%CE%BE%CF%8D" title="Λινελαϊκό οξύ – Greek" lang="el" hreflang="el" data-title="Λινελαϊκό οξύ" 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/%C3%81cido_linoleico" title="Ácido linoleico – Spanish" lang="es" hreflang="es" data-title="Ácido linoleico" 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/Linoleata_acido" title="Linoleata acido – Esperanto" lang="eo" hreflang="eo" data-title="Linoleata acido" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Azido_linoleiko" title="Azido linoleiko – Basque" lang="eu" hreflang="eu" data-title="Azido linoleiko" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%A7%D8%B3%DB%8C%D8%AF_%D9%84%DB%8C%D9%86%D9%88%D9%84%D8%A6%DB%8C%DA%A9" title="اسید لینولئیک – Persian" lang="fa" hreflang="fa" data-title="اسید لینولئیک" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Acide_linol%C3%A9ique" title="Acide linoléique – French" lang="fr" hreflang="fr" data-title="Acide linoléique" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/%C3%81cido_linoleico" title="Ácido linoleico – Galician" lang="gl" hreflang="gl" data-title="Ácido linoleico" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EB%A6%AC%EB%86%80%EB%A0%88%EC%82%B0" title="리놀레산 – Korean" lang="ko" hreflang="ko" data-title="리놀레산" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hi mw-list-item"><a href="https://hi.wikipedia.org/wiki/%E0%A4%B2%E0%A4%BF%E0%A4%A8%E0%A5%8B%E0%A4%B2%E0%A5%87%E0%A4%A8%E0%A4%BF%E0%A4%95_%E0%A4%85%E0%A4%AE%E0%A5%8D%E0%A4%B2" title="लिनोलेनिक अम्ल – Hindi" lang="hi" hreflang="hi" data-title="लिनोलेनिक अम्ल" data-language-autonym="हिन्दी" data-language-local-name="Hindi" class="interlanguage-link-target"><span>हिन्दी</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Asam_linoleat" title="Asam linoleat – Indonesian" lang="id" hreflang="id" data-title="Asam linoleat" 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/Acido_linoleico" title="Acido linoleico – Italian" lang="it" hreflang="it" data-title="Acido linoleico" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%97%D7%95%D7%9E%D7%A6%D7%94_%D7%9C%D7%99%D7%A0%D7%95%D7%9C%D7%90%D7%99%D7%AA" title="חומצה לינולאית – Hebrew" lang="he" hreflang="he" data-title="חומצה לינולאית" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-jv mw-list-item"><a href="https://jv.wikipedia.org/wiki/Asem_linol%C3%A9at" title="Asem linoléat – Javanese" lang="jv" hreflang="jv" data-title="Asem linoléat" data-language-autonym="Jawa" data-language-local-name="Javanese" class="interlanguage-link-target"><span>Jawa</span></a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Linolsk%C4%81be" title="Linolskābe – Latvian" lang="lv" hreflang="lv" data-title="Linolskābe" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target"><span>Latviešu</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Linolsav" title="Linolsav – Hungarian" lang="hu" hreflang="hu" data-title="Linolsav" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-ml mw-list-item"><a href="https://ml.wikipedia.org/wiki/%E0%B4%B2%E0%B4%BF%E0%B4%A8%E0%B5%8B%E0%B4%B2%E0%B5%86%E0%B4%AF%E0%B4%BF%E0%B4%95%E0%B5%8D_%E0%B4%86%E0%B4%B8%E0%B4%BF%E0%B4%A1%E0%B5%8D" title="ലിനോലെയിക് ആസിഡ് – Malayalam" lang="ml" hreflang="ml" data-title="ലിനോലെയിക് ആസിഡ്" data-language-autonym="മലയാളം" data-language-local-name="Malayalam" class="interlanguage-link-target"><span>മലയാളം</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Linolzuur" title="Linolzuur – Dutch" lang="nl" hreflang="nl" data-title="Linolzuur" 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%83%AA%E3%83%8E%E3%83%BC%E3%83%AB%E9%85%B8" title="リノール酸 – Japanese" lang="ja" hreflang="ja" data-title="リノール酸" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-uz mw-list-item"><a href="https://uz.wikipedia.org/wiki/Linol_kislota" title="Linol kislota – Uzbek" lang="uz" hreflang="uz" data-title="Linol kislota" data-language-autonym="Oʻzbekcha / ўзбекча" data-language-local-name="Uzbek" class="interlanguage-link-target"><span>Oʻzbekcha / ўзбекча</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Kwas_linolowy" title="Kwas linolowy – Polish" lang="pl" hreflang="pl" data-title="Kwas linolowy" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/%C3%81cido_linoleico" title="Ácido linoleico – Portuguese" lang="pt" hreflang="pt" data-title="Ácido linoleico" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Acid_linoleic" title="Acid linoleic – Romanian" lang="ro" hreflang="ro" data-title="Acid linoleic" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%9B%D0%B8%D0%BD%D0%BE%D0%BB%D0%B5%D0%B2%D0%B0%D1%8F_%D0%BA%D0%B8%D1%81%D0%BB%D0%BE%D1%82%D0%B0" title="Линолевая кислота – Russian" lang="ru" hreflang="ru" data-title="Линолевая кислота" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Linolna_kislina" title="Linolna kislina – Slovenian" lang="sl" hreflang="sl" data-title="Linolna kislina" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Linolna_kiselina" title="Linolna kiselina – Serbian" lang="sr" hreflang="sr" data-title="Linolna kiselina" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Linolna_kiselina" title="Linolna kiselina – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Linolna kiselina" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Linolihappo" title="Linolihappo – Finnish" lang="fi" hreflang="fi" data-title="Linolihappo" 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/Linolsyra" title="Linolsyra – Swedish" lang="sv" hreflang="sv" data-title="Linolsyra" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%B2%E0%AE%BF%E0%AE%A9%E0%AF%8B%E0%AE%B2%E0%AF%86%E0%AE%AF%E0%AE%BF%E0%AE%95%E0%AF%8D_%E0%AE%85%E0%AE%AE%E0%AE%BF%E0%AE%B2%E0%AE%AE%E0%AF%8D" title="லினோலெயிக் அமிலம் – Tamil" lang="ta" hreflang="ta" data-title="லினோலெயிக் அமிலம்" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-te mw-list-item"><a href="https://te.wikipedia.org/wiki/%E0%B0%B2%E0%B0%BF%E0%B0%A8%E0%B1%8A%E0%B0%B2%E0%B0%BF%E0%B0%95%E0%B1%8D_%E0%B0%86%E0%B0%AE%E0%B1%8D%E0%B0%B2%E0%B0%82" title="లినొలిక్ ఆమ్లం – Telugu" lang="te" hreflang="te" data-title="లినొలిక్ ఆమ్లం" data-language-autonym="తెలుగు" data-language-local-name="Telugu" class="interlanguage-link-target"><span>తెలుగు</span></a></li><li class="interlanguage-link interwiki-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B8%81%E0%B8%A3%E0%B8%94%E0%B8%A5%E0%B8%B4%E0%B9%82%E0%B8%99%E0%B9%80%E0%B8%A5%E0%B8%AD%E0%B8%B4%E0%B8%81" title="กรดลิโนเลอิก – Thai" lang="th" hreflang="th" data-title="กรดลิโนเลอิก" data-language-autonym="ไทย" data-language-local-name="Thai" class="interlanguage-link-target"><span>ไทย</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Linoleik_asit" title="Linoleik asit – Turkish" lang="tr" hreflang="tr" data-title="Linoleik asit" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%9B%D1%96%D0%BD%D0%BE%D0%BB%D0%B5%D0%B2%D0%B0_%D0%BA%D0%B8%D1%81%D0%BB%D0%BE%D1%82%D0%B0" title="Лінолева кислота – Ukrainian" lang="uk" hreflang="uk" data-title="Лінолева кислота" 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/Acid_linoleic" title="Acid linoleic – Vietnamese" lang="vi" hreflang="vi" data-title="Acid linoleic" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target"><span>Tiếng Việt</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E4%BA%9A%E6%B2%B9%E9%85%B8" title="亚油酸 – Chinese" lang="zh" hreflang="zh" data-title="亚油酸" 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/Q407426#sitelinks-wikipedia" title="Edit interlanguage 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dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Polyunsaturated omega−6 fatty acid</div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">Not to be confused with <a href="/wiki/Linolenic_acid" title="Linolenic acid">linolenic acid</a>, <a href="/wiki/Alpha-linolenic_acid" class="mw-redirect" title="Alpha-linolenic acid">alpha-linolenic acid</a>, <a href="/wiki/Lipoic_acid" title="Lipoic acid">lipoic acid</a>, or <a href="/wiki/Linolelaidic_acid" title="Linolelaidic acid">linolelaidic acid</a>.</div> <p> <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> </p> <table class="infobox ib-chembox"> <caption>Linoleic acid </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:LAnumbering.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/70/LAnumbering.png/300px-LAnumbering.png" decoding="async" width="300" height="37" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/70/LAnumbering.png/450px-LAnumbering.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/70/LAnumbering.png/600px-LAnumbering.png 2x" data-file-width="1208" data-file-height="149" /></a></span> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Linoleic-acid-from-xtal-1979-3D-balls.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a8/Linoleic-acid-from-xtal-1979-3D-balls.png/300px-Linoleic-acid-from-xtal-1979-3D-balls.png" decoding="async" width="300" height="70" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a8/Linoleic-acid-from-xtal-1979-3D-balls.png/450px-Linoleic-acid-from-xtal-1979-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a8/Linoleic-acid-from-xtal-1979-3D-balls.png/600px-Linoleic-acid-from-xtal-1979-3D-balls.png 2x" data-file-width="1100" data-file-height="258" /></a></span> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Linoleic-acid-from-xtal-1979-3D-vdW.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/5b/Linoleic-acid-from-xtal-1979-3D-vdW.png/300px-Linoleic-acid-from-xtal-1979-3D-vdW.png" decoding="async" width="300" height="87" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/5b/Linoleic-acid-from-xtal-1979-3D-vdW.png/450px-Linoleic-acid-from-xtal-1979-3D-vdW.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/5b/Linoleic-acid-from-xtal-1979-3D-vdW.png/600px-Linoleic-acid-from-xtal-1979-3D-vdW.png 2x" data-file-width="1100" data-file-height="320" /></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;">(9<i>Z</i>,12<i>Z</i>)-Octadeca-9,12-dienoic acid</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>cis</i>,<i>cis</i>-9,12-Octadecadienoic acid<br />C18:2 (<a href="/wiki/Fatty_acid#Nomenclature" title="Fatty acid">Lipid numbers</a>)</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=60-33-3">60-33-3</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=CCCCC%2FC%3DC%5CC%2FC%3DC%5CCCCCCCCC%28%3DO%29O">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td>3DMet </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.3dmet.dna.affrc.go.jp"><a rel="nofollow" class="external text" href="http://www.3dmet.dna.affrc.go.jp/cgi/show_data.php?acc=B00328">B00328</a></span></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Beilstein_database" title="Beilstein database">Beilstein Reference</a></div> </td> <td>1727101 </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=17351">CHEBI:17351</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/chembldb/index.php/compound/inspect/ChEMBL267476">ChEMBL267476</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.4444105.html">4444105</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/DrugBank" title="DrugBank">DrugBank</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.drugbank.ca"><a rel="nofollow" class="external text" href="https://www.drugbank.ca/drugs/DB14104">DB14104</a></span></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/100.000.428">100.000.428</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q407426#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span> </td></tr> <tr> <td><a href="/wiki/European_Community_number" title="European Community number"><span title="European Community number (chemical identifier)">EC Number</span></a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>200-470-9</li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Gmelin_database" title="Gmelin database">Gmelin Reference</a></div> </td> <td>57557 </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/IUPHAR/BPS" class="mw-redirect" title="IUPHAR/BPS">IUPHAR/BPS</a></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.guidetopharmacology.org"><a rel="nofollow" class="external text" href="http://www.guidetopharmacology.org/GRAC/LigandDisplayForward?tab=summary&ligandId=1052">1052</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/KEGG" title="KEGG">KEGG</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.kegg.jp"><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/C01595">C01595</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/5280450">5280450</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/9KJL21T0QJ">9KJL21T0QJ</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/DTXSID2025505">DTXSID2025505</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q407426#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/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10H,2-5,8,11-17H2,1H3,(H,19,20)/b7-6-,10-9-<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: OYHQOLUKZRVURQ-HZJYTTRNSA-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/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10H,2-5,8,11-17H2,1H3,(H,19,20)/b7-6-,10-9-</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: OYHQOLUKZRVURQ-HZJYTTRNBX</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%;">CCCCC/C=C\C/C=C\CCCCCCCC(=O)O</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td><span title="Carbon">C</span><sub>18</sub><span title="Hydrogen">H</span><sub>32</sub><span title="Oxygen">O</span><sub>2</sub> </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td><span class="nowrap"><span data-sort-value="7002280452000000000♠"></span>280.452</span> g·mol<sup>−1</sup>   </td></tr> <tr> <td>Appearance </td> <td>Colorless oil </td></tr> <tr> <td><a href="/wiki/Density" title="Density">Density</a> </td> <td>0.9 g/cm<sup>3</sup><sup id="cite_ref-Merck_1-0" class="reference"><a href="#cite_note-Merck-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>−12 °C (10 °F)<sup id="cite_ref-Merck_1-1" class="reference"><a href="#cite_note-Merck-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><br />−6.9 °C (19.6 °F)<sup id="cite_ref-crc97_2-0" class="reference"><a href="#cite_note-crc97-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><br />−5 °C (23 °F)<sup id="cite_ref-GESTIS_3-0" class="reference"><a href="#cite_note-GESTIS-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Boiling_point" title="Boiling point">Boiling point</a> </td> <td>229 °C (444 °F) at 16 mmHg<sup id="cite_ref-crc97_2-1" class="reference"><a href="#cite_note-crc97-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><br />230 °C (446 °F) at 21 mbar<sup id="cite_ref-GESTIS_3-1" class="reference"><a href="#cite_note-GESTIS-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><br />230 °C (446 °F) at 16 mmHg<sup id="cite_ref-Merck_1-2" class="reference"><a href="#cite_note-Merck-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Aqueous_solution" title="Aqueous solution">Solubility in water</a></div> </td> <td>0.139 mg/L<sup id="cite_ref-GESTIS_3-2" class="reference"><a href="#cite_note-GESTIS-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Vapor_pressure" title="Vapor pressure">Vapor pressure</a> </td> <td>16 Torr at 229 °C<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (June 2011)">citation needed</span></a></i>]</sup> </td></tr> <tr> <td><a href="/wiki/Acid_dissociation_constant" title="Acid dissociation constant">Acidity</a> (p<i>K</i><sub>a</sub>) </td> <td>4.77 at 25°C<sup id="cite_ref-pubchem_4-0" class="reference"><a href="#cite_note-pubchem-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Hazards </th></tr> <tr> <td><a href="/wiki/NFPA_704" title="NFPA 704"><b>NFPA 704</b></a> (fire diamond) </td> <td><style data-mw-deduplicate="TemplateStyles:r1170367383">.mw-parser-output .nfpa-704-diamond-ref{float:right;padding:1px;text-align:right}.mw-parser-output .nfpa-704-diamond-container{width:82px;font-family:sans-serif;margin:0 auto}.mw-parser-output .nfpa-704-diamond-container-ref{float:left;margin-left:1em}.mw-parser-output .nfpa-704-diamond-images{float:left;font-size:20px;text-align:center;position:relative;height:80px;width:80px;padding:1px}.mw-parser-output .nfpa-704-diamond-map{position:absolute;height:80px;width:80px}.mw-parser-output .nfpa-704-diamond .noresize{margin:0 auto}.mw-parser-output .nfpa-704-diamond-code{line-height:1em;text-align:center;position:absolute}.mw-parser-output .nfpa-704-diamond-code>a{color:black}.mw-parser-output .nfpa-704-diamond-blue{width:13px;top:31px;left:15px}.mw-parser-output .nfpa-704-diamond-red{width:12px;top:12px;left:35px}.mw-parser-output .nfpa-704-diamond-yellow{width:13px;top:31px;left:54px}.mw-parser-output .nfpa-704-diamond-white-image{position:relative;top:51px;left:0}.mw-parser-output .nfpa-704-diamond-white-text{vertical-align:middle;text-align:center;line-height:80%;position:absolute;top:52px}.mw-parser-output .nfpa-704-diamond-white-text a>span{position:absolute;color:black}.mw-parser-output .nfpa-704-diamond-white-wors{font-size:15px;width:23px;left:29px}.mw-parser-output .nfpa-704-diamond-white-wox{font-size:15px;font-stretch:condensed;width:21px;line-height:80%;top:-4px;left:29px}.mw-parser-output .nfpa-704-diamond-white-abcp{font-size:13.5px;font-stretch:condensed;width:28px;left:26px}.mw-parser-output .nfpa-704-diamond-white-ac{font-size:10px;width:30px;left:25px}.mw-parser-output .nfpa-704-diamond-white-strike{text-decoration:line-through}</style><div class="nfpa-704-diamond notheme"><div class="nfpa-704-diamond-container"><div class="nfpa-704-diamond-images nounderlines"> <div class="nfpa-704-diamond-map"><figure class="noresize" typeof="mw:File"><span><img alt="NFPA 704 four-colored diamond" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/80px-NFPA_704.svg.png" decoding="async" width="80" height="80" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/120px-NFPA_704.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/160px-NFPA_704.svg.png 2x" data-file-width="512" data-file-height="512" usemap="#ImageMap_482e25fdfe95519d" /></span><map name="ImageMap_482e25fdfe95519d"><area href="/wiki/NFPA_704#Blue" shape="poly" coords="23,23,47,47,23,70,0,47" alt="Health 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroform" title="Health 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroform" /><area href="/wiki/NFPA_704#Red" shape="poly" coords="47,0,70,23,47,47,23,23" alt="Flammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oil" title="Flammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oil" /><area href="/wiki/NFPA_704#Yellow" shape="poly" coords="70,23,94,47,70,70,47,47" alt="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" title="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" /><area href="/wiki/NFPA_704#White" shape="poly" coords="47,47,70,70,47,94,23,70" alt="Special hazards (white): no code" title="Special hazards (white): no code" /></map><figcaption></figcaption></figure></div><div class="nfpa-704-diamond-code nfpa-704-diamond-blue"> <a href="/wiki/NFPA_704#Blue" title="NFPA 704"><span title="Health 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroform" class="notheme mw-no-invert">2</span></a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-red"> <a href="/wiki/NFPA_704#Red" title="NFPA 704"><span title="Flammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oil" class="notheme mw-no-invert">1</span></a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-yellow"> <a href="/wiki/NFPA_704#Yellow" title="NFPA 704"><span title="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" class="notheme mw-no-invert">0</span></a></div></div></div></div> </td></tr> <tr> <td><a href="/wiki/Flash_point" title="Flash point">Flash point</a> </td> <td>112 °C (234 °F)<sup id="cite_ref-GESTIS_3-3" class="reference"><a href="#cite_note-GESTIS-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </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=476999843&page2=Linoleic+acid">verify</a></span> (<a href="/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validation" title="Wikipedia:WikiProject Chemicals/Chembox validation">what is</a> <sup><span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup> ?) </div></div> <div style="margin-top: 0.3em; text-align: center;"><a href="/wiki/Wikipedia:Chemical_infobox#References" title="Wikipedia:Chemical infobox">Infobox references</a></div> </td></tr> </tbody></table><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound</div> <p><b>Linoleic acid</b> (<b>LA</b>) is an <a href="/wiki/Organic_compound" title="Organic compound">organic compound</a> with the formula <style data-mw-deduplicate="TemplateStyles:r1123817410">.mw-parser-output .template-chem2-su{display:inline-block;font-size:80%;line-height:1;vertical-align:-0.35em}.mw-parser-output .template-chem2-su>span{display:block;text-align:left}.mw-parser-output sub.template-chem2-sub{font-size:80%;vertical-align:-0.35em}.mw-parser-output sup.template-chem2-sup{font-size:80%;vertical-align:0.65em}</style><span class="chemf nowrap">HOOC(CH<sub class="template-chem2-sub">2</sub>)<sub class="template-chem2-sub">7</sub>CH=CHCH<sub class="template-chem2-sub">2</sub>CH=CH(CH<sub class="template-chem2-sub">2</sub>)<sub class="template-chem2-sub">4</sub>CH<sub class="template-chem2-sub">3</sub></span>. Both <a href="/wiki/Alkene" title="Alkene">alkene</a> groups (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−CH=CH−</span>) are <a href="/wiki/Cis-trans_isomerism" class="mw-redirect" title="Cis-trans isomerism"><i>cis</i></a>. It is a <a href="/wiki/Fatty_acid" title="Fatty acid">fatty acid</a> sometimes denoted 18:2 (n−6) or 18:2 <i>cis</i>-9,12. A <b>linoleate</b> is a <a href="/wiki/Salt_(chemistry)" title="Salt (chemistry)">salt</a> or <a href="/wiki/Ester" title="Ester">ester</a> of this acid.<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>Linoleic acid is a <a href="/wiki/Polyunsaturated_fatty_acid" class="mw-redirect" title="Polyunsaturated fatty acid">polyunsaturated</a>, <a href="/wiki/Omega-6_fatty_acid" title="Omega-6 fatty acid">omega−6 fatty acid</a>. It is a colorless liquid that is virtually <a href="/wiki/Insoluble" class="mw-redirect" title="Insoluble">insoluble</a> in water but soluble in many <a href="/wiki/Organic_solvent" class="mw-redirect" title="Organic solvent">organic solvents</a>.<sup id="cite_ref-crc97_2-2" class="reference"><a href="#cite_note-crc97-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> It typically occurs in nature as a <a href="/wiki/Triglyceride" title="Triglyceride">triglyceride</a> (ester of <a href="/wiki/Glycerol" title="Glycerol">glycerin</a>) rather than as a <a href="/wiki/Free_fatty_acid" class="mw-redirect" title="Free fatty acid">free fatty acid</a>.<sup id="cite_ref-Is_there_a_fatty_acid_taste_6-0" class="reference"><a href="#cite_note-Is_there_a_fatty_acid_taste-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> It is one of two <a href="/wiki/Essential_fatty_acid" title="Essential fatty acid">essential fatty acids</a> for humans, who must obtain it through their diet,<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> and the most essential, because the body uses it as a base to make the others. </p><p>The word "linoleic" derives from <a href="/wiki/Latin_language" class="mw-redirect" title="Latin language">Latin</a> <i> linum</i> '<a href="/wiki/Flax" title="Flax">flax</a>' and <i> oleum</i> 'oil', reflecting the fact that it was first isolated from <a href="/wiki/Linseed_oil" title="Linseed oil">linseed oil</a>. </p> <meta property="mw:PageProp/toc" /> <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=Linoleic_acid&action=edit&section=1" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In 1844, <a href="/w/index.php?title=Fritz_Sacc&action=edit&redlink=1" class="new" title="Fritz Sacc (page does not exist)">F. Sacc</a>, working at the laboratory of <a href="/wiki/Justus_von_Liebig" title="Justus von Liebig">Justus von Liebig</a>, isolated linoleic acid from linseed oil.<sup id="cite_ref-sacc1844_8-0" class="reference"><a href="#cite_note-sacc1844-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-sacc1845_9-0" class="reference"><a href="#cite_note-sacc1845-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> In 1886, <a href="/w/index.php?title=Karl_Peters_(chemist)&action=edit&redlink=1" class="new" title="Karl Peters (chemist) (page does not exist)">K. Peters</a> determined the existence of two double bonds.<sup id="cite_ref-Peters_10-0" class="reference"><a href="#cite_note-Peters-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> Its essential role in human diet was discovered by <a href="/w/index.php?title=George_O._Burr&action=edit&redlink=1" class="new" title="George O. Burr (page does not exist)">G. O. Burr</a> and others in 1930.<sup id="cite_ref-burr1930_11-0" class="reference"><a href="#cite_note-burr1930-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> Its chemical structure was determined by <a href="/wiki/Thomas_Percy_Hilditch" title="Thomas Percy Hilditch">T. P. Hilditch</a> and others in 1939, and it was synthesized by <a href="/wiki/Ralph_Raphael" title="Ralph Raphael">R. A. Raphael</a> and <a href="/wiki/Franz_Sondheimer" title="Franz Sondheimer">F. Sondheimer</a> in 1950.<sup id="cite_ref-raph1950_12-0" class="reference"><a href="#cite_note-raph1950-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="In_physiology">In physiology</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Linoleic_acid&action=edit&section=2" title="Edit section: In physiology"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main articles: <a href="/wiki/Fatty_acid_desaturase" title="Fatty acid desaturase">Fatty acid desaturase</a> and <a href="/wiki/Fatty_acid_synthesis" title="Fatty acid synthesis">Fatty acid synthesis</a></div> <p>The consumption of linoleic acid is vital to proper health, as it is an essential fatty acid.<sup id="cite_ref-Whelan_&_Fritsche_13-0" class="reference"><a href="#cite_note-Whelan_&_Fritsche-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Metabolism_and_eicosanoids">Metabolism and eicosanoids</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Linoleic_acid&action=edit&section=3" title="Edit section: Metabolism and eicosanoids"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><span class="mw-default-size" typeof="mw:File"><a href="/wiki/File:Linoleic_Acid_Metabolism.gif" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/b/bb/Linoleic_Acid_Metabolism.gif" decoding="async" width="457" height="471" class="mw-file-element" data-file-width="457" data-file-height="471" /></a></span></p><div style="clear:left;" class=""></div> <p>Linoleic acid (LA: <span class="chemf nowrap"><a href="/wiki/Carbon" title="Carbon">C</a><span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">18</sub></span></span><a href="/wiki/Hydrogen" title="Hydrogen">H</a><span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">32</sub></span></span><a href="/wiki/Oxygen" title="Oxygen">O</a><span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2</sub></span></span></span>; 18:<a href="/wiki/Double_bond" title="Double bond">2</a>,<a href="/wiki/Omega-6_fatty_acid" title="Omega-6 fatty acid">n−6</a>) is a precursor to <a href="/wiki/Arachidonic_acid" title="Arachidonic acid">arachidonic acid</a> (AA: <span class="chemf nowrap">C<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">20</sub></span></span>H<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">32</sub></span></span>O<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2</sub></span></span></span>; 20:<a href="/wiki/Double_bond" title="Double bond">4</a>,n−6) with elongation and unsaturation.<sup id="cite_ref-Whelan_&_Fritsche_13-1" class="reference"><a href="#cite_note-Whelan_&_Fritsche-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> AA is the precursor to some <a href="/wiki/Prostaglandin" title="Prostaglandin">prostaglandins</a>,<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Leukotriene" title="Leukotriene">leukotrienes</a> (LTA, LTB, LTC), <a href="/wiki/Thromboxane" title="Thromboxane">thromboxane</a> (TXA)<sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> and the <a href="/wiki/N-Acylethanolamine" title="N-Acylethanolamine">N-acylethanolamine</a> (NAE) <a href="/wiki/Anandamide" title="Anandamide">arachidonoylethanolamine</a> (AEA: <span class="chemf nowrap">C<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">22</sub></span></span>H<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">37</sub></span></span><a href="/wiki/Biological_functions_of_nitric_oxide" title="Biological functions of nitric oxide">NO</a><span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2</sub></span></span></span>; 20:4,n−6),<sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> and other <a href="/wiki/Endocannabinoid_system" title="Endocannabinoid system">endocannabinoids</a> and <a href="/wiki/Eicosanoid" title="Eicosanoid">eicosanoids</a>.<sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </p><p>The metabolism of LA to AA begins with the conversion of LA into <a href="/wiki/Gamma-Linolenic_acid" class="mw-redirect" title="Gamma-Linolenic acid">gamma-linolenic acid</a> (GLA), effected by <a href="/wiki/Delta_6_desaturase" class="mw-redirect" title="Delta 6 desaturase">Δ6 desaturase</a>.<sup id="cite_ref-David_F._Horrobin_1993_18-0" class="reference"><a href="#cite_note-David_F._Horrobin_1993-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> GLA is converted to <a href="/wiki/Dihomo-%CE%B3-linolenic_acid" title="Dihomo-γ-linolenic acid">dihomo-γ-linolenic acid</a> (DGLA), the immediate precursor to AA. </p><p>LA is also converted by various <a href="/wiki/Lipoxygenase" title="Lipoxygenase">lipoxygenases</a>, <a href="/wiki/Cyclooxygenase" title="Cyclooxygenase">cyclooxygenases</a>, <a href="/wiki/Cytochrome_P450" title="Cytochrome P450">cytochrome P450</a> enzymes (the CYP <a href="/wiki/Monooxygenase" title="Monooxygenase">monooxygenases</a>), and non-enzymatic <a href="/wiki/Autoxidation" title="Autoxidation">autoxidation</a> mechanisms to mono-<a href="/wiki/Hydroxy_group" title="Hydroxy group">hydroxyl</a> products viz., <a href="/wiki/13-Hydroxyoctadecadienoic_acid" title="13-Hydroxyoctadecadienoic acid">13-Hydroxyoctadecadienoic acid</a>, and <a href="/wiki/9-Hydroxyoctadecadienoic_acid" title="9-Hydroxyoctadecadienoic acid">9-Hydroxyoctadecadienoic acid</a>; these two hydroxy metabolites are enzymatically oxidized to their keto metabolites, 13-oxo-octadecadienoic acid and 9-oxo-octadecdienoic acid. Certain cytochrome P450 enzymes, the CYP <a href="/wiki/Epoxygenase" title="Epoxygenase">epoxygenases</a>, catalyze oxidation of LA to epoxide products viz., its 12,13-epoxide, <a href="/wiki/Vernolic_acid" title="Vernolic acid">vernolic acid</a>, and its 9,10-epoxide, <a href="/wiki/Coronaric_acid" title="Coronaric acid">coronaric acid</a>. These linoleic acid products are implicated in human physiology and pathology.<sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> </p><p><a href="/wiki/Hydroperoxide" title="Hydroperoxide">Hydroperoxides</a> derived from the metabolism of <a href="/wiki/Anandamide" title="Anandamide">anandamide</a> (AEA: <span class="chemf nowrap">C<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">22</sub></span></span>H<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">37</sub></span></span><a href="/wiki/Biological_functions_of_nitric_oxide" title="Biological functions of nitric oxide">NO</a><span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2</sub></span></span></span>; 20:4,n−6), or its <a href="/wiki/Linoleyl_alcohol" title="Linoleyl alcohol">linoleoyl</a> analogues, are by a <a href="/wiki/Lipoxygenase" title="Lipoxygenase">lipoxygenase</a> action found to be competitive inhibitors of <a href="/wiki/Brain" title="Brain">brain</a> and <a href="/wiki/White_blood_cell" title="White blood cell">immune cell</a> <a href="/wiki/Fatty_acid_amide_hydrolase" class="mw-redirect" title="Fatty acid amide hydrolase">FAAH</a>, the <a href="/wiki/Enzyme" title="Enzyme">enzyme</a> that breaks down AEA and other endocannabinoids, and the compound linoleoyl-ethanol-amide (<span class="chemf nowrap">C<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">20</sub></span></span>H<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">37</sub></span></span>NO<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2</sub></span></span></span>; 18:2,n−6), an <a href="/wiki/N-Acylethanolamine" title="N-Acylethanolamine">N-acylethanolamine</a>,<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="Style of this sentence makes it incomprehensible to the reader. It needs to be reworded. (February 2023)">clarification needed</span></a></i>]</sup> - the <a href="/wiki/Ethanolamide" title="Ethanolamide">ethanolamide</a> of linoleic acid (LA: <span class="chemf nowrap">C<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">18</sub></span></span>H<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">32</sub></span></span>O<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2</sub></span></span></span>; 18:<a href="/wiki/Double_bond" title="Double bond">2</a>,n−6) and its metabolized incorporated <a href="/wiki/Ethanolamine" title="Ethanolamine">ethanolamine</a> (MEA: <span class="chemf nowrap">C<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2</sub></span></span>H<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">7</sub></span></span>NO</span>),<sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> is the first natural inhibitor of FAAH, discovered.<sup id="cite_ref-21" class="reference"><a href="#cite_note-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-22" class="reference"><a href="#cite_note-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Uses_and_reactions">Uses and reactions</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Linoleic_acid&action=edit&section=4" title="Edit section: Uses and reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Linoleic acid is a component of quick-<a href="/wiki/Drying_oil" title="Drying oil">drying oils</a>, which are useful in <a href="/wiki/Oil_paint" title="Oil paint">oil paints</a> and <a href="/wiki/Varnish" title="Varnish">varnishes</a>. These applications exploit the lability of the doubly <a href="/wiki/Allylic" class="mw-redirect" title="Allylic">allylic</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C−H</span> groups (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−CH=CH−C<i>H</i><sub class="template-chem2-sub">2</sub>−CH=CH−</span>) toward oxygen in air (<a href="/wiki/Autoxidation" title="Autoxidation">autoxidation</a>). Addition of oxygen leads to <a href="/wiki/Cross-link" title="Cross-link">crosslinking</a> and formation of a stable film.<sup id="cite_ref-23" class="reference"><a href="#cite_note-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> </p><p>Reduction of the carboxylic acid group of linoleic acid yields <a href="/wiki/Linoleyl_alcohol" title="Linoleyl alcohol">linoleyl alcohol</a>.<sup id="cite_ref-24" class="reference"><a href="#cite_note-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> </p><p>Linoleic acid is a <a href="/wiki/Surfactant" title="Surfactant">surfactant</a> with a critical micelle concentration of 1.5 x 10<sup>−4</sup> M @ pH 7.5.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (February 2021)">citation needed</span></a></i>]</sup> </p><p>Linoleic acid has become increasingly popular in the beauty products industry because of its beneficial properties on the skin. Research points to linoleic acid's anti-inflammatory, acne reductive, skin-lightening and moisture retentive properties when applied topically on the <a href="/wiki/Human_skin" title="Human skin">skin</a>.<sup id="cite_ref-25" class="reference"><a href="#cite_note-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-26" class="reference"><a href="#cite_note-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-27" class="reference"><a href="#cite_note-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> </p><p>Linoleic acid is also used in some <a href="/wiki/Soap" title="Soap">bar of soap</a> products. </p> <div class="mw-heading mw-heading2"><h2 id="Dietary_sources">Dietary sources</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Linoleic_acid&action=edit&section=5" title="Edit section: Dietary sources"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/Vegetable_oil#Composition_of_fats" title="Vegetable oil">Vegetable oil § Composition of fats</a></div> <p>It is abundant in <a href="/wiki/Safflower" title="Safflower">safflower</a>, and <a href="/wiki/Corn_oil" title="Corn oil">corn</a> oil, and comprises over half their composition by weight. It is present in medium quantities in <a href="/wiki/Soybean_oil" title="Soybean oil">soybean oils</a>, <a href="/wiki/Sesame" title="Sesame">sesame</a>, and <a href="/wiki/Almonds" class="mw-redirect" title="Almonds">almonds</a>.<sup id="cite_ref-USDA_29-0" class="reference"><a href="#cite_note-USDA-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-30" class="reference"><a href="#cite_note-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> </p> <table class="wikitable sortable"> <tbody><tr> <th>Name</th> <th>% LA<sup>†</sup></th> <th>ref. </th></tr> <tr> <td><a href="/wiki/Salicornia_oil" title="Salicornia oil">Salicornia oil</a></td> <td>75%</td> <td><sup id="cite_ref-Alfheeaid_31-0" class="reference"><a href="#cite_note-Alfheeaid-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Safflower" title="Safflower">Safflower</a> oil</td> <td>72–78%</td> <td><sup id="cite_ref-Hall2015_32-0" class="reference"><a href="#cite_note-Hall2015-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Oenothera" title="Oenothera">Evening Primrose oil</a></td> <td>65–80%</td> <td><sup id="cite_ref-33" class="reference"><a href="#cite_note-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Melon_seed" class="mw-redirect" title="Melon seed">Melon seed</a> oil</td> <td>50–70%</td> <td><sup id="cite_ref-Cucumis_melo_34-0" class="reference"><a href="#cite_note-Cucumis_melo-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Poppyseed_oil" title="Poppyseed oil">Poppyseed oil</a></td> <td>74%</td> <td><sup id="cite_ref-Bozan_35-0" class="reference"><a href="#cite_note-Bozan-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Grape_seed_oil" title="Grape seed oil">Grape seed oil</a></td> <td>70%</td> <td><sup id="cite_ref-Martin_36-0" class="reference"><a href="#cite_note-Martin-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Opuntia_ficus-indica" title="Opuntia ficus-indica">Prickly Pear</a> seed oil</td> <td>50–78%</td> <td><sup id="cite_ref-Al-Naqeb_37-0" class="reference"><a href="#cite_note-Al-Naqeb-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Cardoon" title="Cardoon">Cardoon</a> oil</td> <td>60%</td> <td><sup id="cite_ref-Varvouni_38-0" class="reference"><a href="#cite_note-Varvouni-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Barbosa_39-0" class="reference"><a href="#cite_note-Barbosa-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Hemp_oil" title="Hemp oil">Hemp oil</a></td> <td>54.3%</td> <td><sup id="cite_ref-40" class="reference"><a href="#cite_note-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Wheat_germ_oil" title="Wheat germ oil">Wheat germ oil</a></td> <td>56%</td> <td><sup id="cite_ref-Rahim_41-0" class="reference"><a href="#cite_note-Rahim-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Siraj_42-0" class="reference"><a href="#cite_note-Siraj-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Cottonseed_oil" title="Cottonseed oil">Cottonseed oil</a></td> <td>54%</td> <td><sup id="cite_ref-Lukonge_43-0" class="reference"><a href="#cite_note-Lukonge-43"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Yang_44-0" class="reference"><a href="#cite_note-Yang-44"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Corn_oil" title="Corn oil">Corn oil</a></td> <td>51.9%</td> <td><sup id="cite_ref-45" class="reference"><a href="#cite_note-45"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Walnut_oil" title="Walnut oil">Walnut oil</a></td> <td>50–72%</td> <td><sup id="cite_ref-Masoodi_46-0" class="reference"><a href="#cite_note-Masoodi-46"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Walnut_47-0" class="reference"><a href="#cite_note-Walnut-47"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Soybean_oil" title="Soybean oil">Soybean oil</a></td> <td>50.9%</td> <td><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> </td></tr> <tr> <td><a href="/wiki/Sesame_oil" title="Sesame oil">Sesame oil</a></td> <td>45%</td> <td><sup id="cite_ref-Dunford_49-0" class="reference"><a href="#cite_note-Dunford-49"><span class="cite-bracket">[</span>49<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Oboulbiga_50-0" class="reference"><a href="#cite_note-Oboulbiga-50"><span class="cite-bracket">[</span>50<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Pumpkin_seed_oil" title="Pumpkin seed oil">Pumpkin seed oil</a></td> <td>42–59%</td> <td><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> </td></tr> <tr> <td><a href="/wiki/Rice_bran_oil" title="Rice bran oil">Rice bran oil</a></td> <td>39%</td> <td> </td></tr> <tr> <td><a href="/wiki/Argan_oil" title="Argan oil">Argan oil</a></td> <td>37%</td> <td> </td></tr> <tr> <td><a href="/wiki/Pistachio_oil" title="Pistachio oil">Pistachio oil</a></td> <td>32.7%</td> <td> </td></tr> <tr> <td><a href="/wiki/Peach" title="Peach">Peach</a> oil</td> <td>29%</td> <td><sup id="cite_ref-sdpk_52-0" class="reference"><a href="#cite_note-sdpk-52"><span class="cite-bracket">[</span>52<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Almond" title="Almond">Almonds</a></td> <td>24%</td> <td> </td></tr> <tr> <td><a href="/wiki/Canola" class="mw-redirect" title="Canola">Canola</a> oil</td> <td>17.8%</td> <td><sup id="cite_ref-53" class="reference"><a href="#cite_note-53"><span class="cite-bracket">[</span>53<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Sunflower_oil" title="Sunflower oil">Sunflower oil</a></td> <td>20.5%</td> <td><sup id="cite_ref-54" class="reference"><a href="#cite_note-54"><span class="cite-bracket">[</span>54<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Chicken_fat" title="Chicken fat">Chicken fat</a></td> <td>18–23%</td> <td><sup id="cite_ref-55" class="reference"><a href="#cite_note-55"><span class="cite-bracket">[</span>55<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Peanut_oil" title="Peanut oil">Peanut oil</a></td> <td>19.6%</td> <td><sup id="cite_ref-56" class="reference"><a href="#cite_note-56"><span class="cite-bracket">[</span>56<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td>Egg <a href="/wiki/Yolk" title="Yolk">yolk</a></td> <td>16%</td> <td> </td></tr> <tr> <td><a href="/wiki/Linseed_oil" title="Linseed oil">Linseed oil</a> (flax), cold pressed</td> <td>14.2%</td> <td><sup id="cite_ref-57" class="reference"><a href="#cite_note-57"><span class="cite-bracket">[</span>57<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Lard" title="Lard">Lard</a></td> <td>10%</td> <td> </td></tr> <tr> <td><a href="/wiki/Palm_oil" title="Palm oil">Palm oil</a></td> <td>10%</td> <td> </td></tr> <tr> <td><a href="/wiki/Olive_oil" title="Olive oil">Olive oil</a></td> <td>8.4%</td> <td><sup id="cite_ref-58" class="reference"><a href="#cite_note-58"><span class="cite-bracket">[</span>58<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Tallow" title="Tallow">Tallow</a> </td> <td>3% </td> <td> </td></tr> <tr> <td><a href="/wiki/Cocoa_butter" title="Cocoa butter">Cocoa butter</a></td> <td>3%</td> <td> </td></tr> <tr> <td><a href="/wiki/Macadamia_oil" title="Macadamia oil">Macadamia oil</a></td> <td>2%</td> <td> </td></tr> <tr> <td><a href="/wiki/Butter" title="Butter">Butter</a></td> <td>2%</td> <td> </td></tr> <tr> <td><a href="/wiki/Coconut_oil" title="Coconut oil">Coconut oil</a></td> <td>2%</td> <td> </td></tr> <tr> <td>  </td> <td colspan="2"><small><sup>†</sup>average val, except the items where a range is given</small> </td></tr></tbody></table> <div class="mw-heading mw-heading3"><h3 id="Other_occurrences">Other occurrences</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Linoleic_acid&action=edit&section=6" title="Edit section: Other occurrences"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Cockroach" title="Cockroach">Cockroaches</a> release oleic and linoleic acid upon death, which discourages other roaches from entering the area. This is similar to the mechanism found in ants and bees, which release oleic acid upon death.<sup id="cite_ref-BBC_59-0" class="reference"><a href="#cite_note-BBC-59"><span class="cite-bracket">[</span>59<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Health_effects">Health effects</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Linoleic_acid&action=edit&section=7" title="Edit section: Health effects"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Consumption of linoleic acid has been associated with lowering the risk of <a href="/wiki/Cardiovascular_disease" title="Cardiovascular disease">cardiovascular disease</a>, diabetes and premature death.<sup id="cite_ref-60" class="reference"><a href="#cite_note-60"><span class="cite-bracket">[</span>60<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-61" class="reference"><a href="#cite_note-61"><span class="cite-bracket">[</span>61<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-62" class="reference"><a href="#cite_note-62"><span class="cite-bracket">[</span>62<span class="cite-bracket">]</span></a></sup> There is high-quality evidence that increased intake of linoleic acid decreases total blood cholesterol and <a href="/wiki/Low-density_lipoprotein" title="Low-density lipoprotein">low-density lipoprotein</a>.<sup id="cite_ref-63" class="reference"><a href="#cite_note-63"><span class="cite-bracket">[</span>63<span class="cite-bracket">]</span></a></sup> Higher in vivo circulating and tissue levels of linoleic acid are associated with a lower risk of major cardiovascular events.<sup id="cite_ref-64" class="reference"><a href="#cite_note-64"><span class="cite-bracket">[</span>64<span class="cite-bracket">]</span></a></sup> Clinical trials have shown that increased linoleic acid intake does not increase markers of inflammation or oxidative stress.<sup id="cite_ref-65" class="reference"><a href="#cite_note-65"><span class="cite-bracket">[</span>65<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-66" class="reference"><a href="#cite_note-66"><span class="cite-bracket">[</span>66<span class="cite-bracket">]</span></a></sup> </p><p>The <a href="/wiki/American_Heart_Association" title="American Heart Association">American Heart Association</a> advises people to replace saturated fat with linoleic acid to reduce CVD risk.<sup id="cite_ref-67" class="reference"><a href="#cite_note-67"><span class="cite-bracket">[</span>67<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=Linoleic_acid&action=edit&section=8" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Conjugated_linoleic_acid" title="Conjugated linoleic acid">Conjugated linoleic acid</a></li> <li><a href="/wiki/Essential_fatty_acid_interactions" title="Essential fatty acid interactions">Essential fatty acid interactions</a></li> <li><a href="/wiki/Essential_nutrient" class="mw-redirect" title="Essential nutrient">Essential nutrients</a></li> <li><a href="/wiki/Linolein" title="Linolein">Linolein</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=Linoleic_acid&action=edit&section=9" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-Merck-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-Merck_1-0"><sup><i><b>a</b></i></sup></a> <a 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"Perspective on the health effects of unsaturated fatty acids and commonly consumed plant oils high in unsaturated fat". <i>British Journal of Nutrition</i>. <b>30</b>: 1–12. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1017%2FS0007114524002459">10.1017/S0007114524002459</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/39475012">39475012</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=British+Journal+of+Nutrition&rft.atitle=Perspective+on+the+health+effects+of+unsaturated+fatty+acids+and+commonly+consumed+plant+oils+high+in+unsaturated+fat&rft.volume=30&rft.pages=1-12&rft.date=2024&rft_id=info%3Adoi%2F10.1017%2FS0007114524002459&rft_id=info%3Apmid%2F39475012&rft.au=Petersen+KS%2C+Maki+KC%2C+Calder+PC%2C+Belury+MA%2C+Messina+M%2C+Kirkpatrick+CF%2C+Harris+WS.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALinoleic+acid" class="Z3988"></span><span class="cs1-maint citation-comment"><code class="cs1-code">{{<a href="/wiki/Template:Cite_journal" title="Template:Cite journal">cite journal</a>}}</code>: CS1 maint: multiple names: authors list (<a href="/wiki/Category:CS1_maint:_multiple_names:_authors_list" title="Category:CS1 maint: multiple names: authors list">link</a>)</span></span> </li> <li id="cite_note-67"><span class="mw-cite-backlink"><b><a href="#cite_ref-67">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSacksLichtensteinWuAppel2017" class="citation journal cs1">Sacks FM, Lichtenstein AH, Wu JH, Appel LJ, Creager MA, Kris-Etherton PM, Miller M, Rimm EB, Rudel LL, Robinson JG, Stone NJ, Van Horn LV (July 2017). <a rel="nofollow" class="external text" href="https://doi.org/10.1161%2FCIR.0000000000000510">"Dietary Fats and Cardiovascular Disease: A Presidential Advisory From the American Heart Association"</a>. <i>Circulation</i>. <b>136</b> (3): e1–e23. <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/10.1161%2FCIR.0000000000000510">10.1161/CIR.0000000000000510</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/28620111">28620111</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:367602">367602</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Circulation&rft.atitle=Dietary+Fats+and+Cardiovascular+Disease%3A+A+Presidential+Advisory+From+the+American+Heart+Association&rft.volume=136&rft.issue=3&rft.pages=e1-e23&rft.date=2017-07&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A367602%23id-name%3DS2CID&rft_id=info%3Apmid%2F28620111&rft_id=info%3Adoi%2F10.1161%2FCIR.0000000000000510&rft.aulast=Sacks&rft.aufirst=FM&rft.au=Lichtenstein%2C+AH&rft.au=Wu%2C+JH&rft.au=Appel%2C+LJ&rft.au=Creager%2C+MA&rft.au=Kris-Etherton%2C+PM&rft.au=Miller%2C+M&rft.au=Rimm%2C+EB&rft.au=Rudel%2C+LL&rft.au=Robinson%2C+JG&rft.au=Stone%2C+NJ&rft.au=Van+Horn%2C+LV&rft_id=https%3A%2F%2Fdoi.org%2F10.1161%252FCIR.0000000000000510&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALinoleic+acid" class="Z3988"></span></span> </li> </ol></div> <div class="mw-heading mw-heading2"><h2 id="Further_reading">Further reading</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Linoleic_acid&action=edit&section=10" title="Edit section: Further reading"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/linoleic_acid">"Compound Summary: Linoleic acid"</a>. <i>PubChem</i>. U.S. National Library of Medicine.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=PubChem&rft.atitle=Compound+Summary%3A+Linoleic+acid&rft_id=https%3A%2F%2Fpubchem.ncbi.nlm.nih.gov%2Fcompound%2Flinoleic_acid&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALinoleic+acid" class="Z3988"></span></li></ul> <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=Linoleic_acid&action=edit&section=11" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a rel="nofollow" class="external text" href="http://gmd.mpimp-golm.mpg.de/Spectrums/36c6cc53-c36d-4485-8c63-615d001552d3.aspx">Linoleic acid MS Spectrum</a></li> <li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20110827030232/http://lipidlibrary.aocs.org/Lipids/fa_poly/index.htm">Fatty Acids: Methylene-Interrupted Double Bonds</a>, AOCS Lipid Library</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 dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output .hlist.inline,.mw-parser-output .hlist.inline dl,.mw-parser-output .hlist.inline ol,.mw-parser-output .hlist.inline ul,.mw-parser-output .hlist dl dl,.mw-parser-output .hlist dl ol,.mw-parser-output .hlist dl ul,.mw-parser-output .hlist ol dl,.mw-parser-output .hlist ol ol,.mw-parser-output .hlist ol ul,.mw-parser-output .hlist ul dl,.mw-parser-output .hlist ul ol,.mw-parser-output .hlist ul ul{display:inline}.mw-parser-output .hlist .mw-empty-li{display:none}.mw-parser-output .hlist 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4em"><a href="/wiki/Lipid" title="Lipid">Lipids</a>: <a href="/wiki/Fatty_acid" title="Fatty acid">fatty acids</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Saturated_fat" title="Saturated fat">Saturated</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Propionic_acid" title="Propionic acid">Propionic</a> (C3)</li> <li><a href="/wiki/Butyric_acid" title="Butyric acid">Butyric</a> (C4)</li> <li><a href="/wiki/Valeric_acid" title="Valeric acid">Valeric</a> (C5)</li> <li><a href="/wiki/Caproic_acid" title="Caproic acid">Caproic</a> (C6)</li> <li><a href="/wiki/Enanthic_acid" title="Enanthic acid">Enanthic</a> (C7)</li> <li><a href="/wiki/Caprylic_acid" title="Caprylic acid">Caprylic</a> (C8)</li> <li><a href="/wiki/Pelargonic_acid" title="Pelargonic acid">Pelargonic</a> (C9)</li> <li><a href="/wiki/Capric_acid" title="Capric acid">Capric</a> (C10)</li> <li><a href="/wiki/Undecylic_acid" title="Undecylic acid">Undecylic</a> (C11)</li> <li><a href="/wiki/Lauric_acid" title="Lauric acid">Lauric</a> (C12)</li> <li><a href="/wiki/Tridecylic_acid" title="Tridecylic acid">Tridecylic</a> (C13)</li> <li><a href="/wiki/Myristic_acid" title="Myristic acid">Myristic</a> (C14)</li> <li><a href="/wiki/Pentadecylic_acid" title="Pentadecylic acid">Pentadecylic</a> (C15)</li> <li><a href="/wiki/Palmitic_acid" title="Palmitic acid">Palmitic</a> (C16)</li> <li><a href="/wiki/Margaric_acid" title="Margaric acid">Margaric</a> (C17)</li> <li><a href="/wiki/Stearic_acid" title="Stearic acid">Stearic</a> (C18)</li> <li><a href="/wiki/Nonadecylic_acid" title="Nonadecylic acid">Nonadecylic</a> (C19)</li> <li><a href="/wiki/Arachidic_acid" title="Arachidic acid">Arachidic</a> (C20)</li> <li><a href="/wiki/Heneicosylic_acid" title="Heneicosylic acid">Heneicosylic</a> (C21)</li> <li><a href="/wiki/Behenic_acid" title="Behenic acid">Behenic</a> (C22)</li> <li><a href="/wiki/Tricosylic_acid" title="Tricosylic acid">Tricosylic</a> (C23)</li> <li><a href="/wiki/Lignoceric_acid" title="Lignoceric acid">Lignoceric</a> (C24)</li> <li><a href="/wiki/Pentacosylic_acid" title="Pentacosylic acid">Pentacosylic</a> (C25)</li> <li><a href="/wiki/Cerotic_acid" title="Cerotic acid">Cerotic</a> (C26)</li> <li><a href="/wiki/Carboceric_acid" title="Carboceric acid">Carboceric</a> (C27)</li> <li><a href="/wiki/Montanic_acid" title="Montanic acid">Montanic</a> (C28)</li> <li><a href="/wiki/Nonacosylic_acid" title="Nonacosylic acid">Nonacosylic</a> (C29)</li> <li><a href="/wiki/Melissic_acid" title="Melissic acid">Melissic</a> (C30)</li> <li><a href="/wiki/Hentriacontylic_acid" title="Hentriacontylic acid">Hentriacontylic</a> (C31)</li> <li><a href="/wiki/Lacceroic_acid" title="Lacceroic acid">Lacceroic</a> (C32)</li> <li><a href="/wiki/Psyllic_acid" title="Psyllic acid">Psyllic</a> (C33)</li> <li><a href="/wiki/Geddic_acid" title="Geddic acid">Geddic</a> (C34)</li> <li><a href="/wiki/Ceroplastic_acid" title="Ceroplastic acid">Ceroplastic</a> (C35)</li> <li><a href="/wiki/Hexatriacontylic_acid" title="Hexatriacontylic acid">Hexatriacontylic</a> (C36)</li> <li><a href="/wiki/Heptatriacontanoic_acid" title="Heptatriacontanoic acid">Heptatriacontanoic</a> (C37)</li> <li><a href="/w/index.php?title=Octatriacontanoic_acid&action=edit&redlink=1" class="new" title="Octatriacontanoic acid (page does not exist)">Octatriacontanoic</a> (C38)</li> <li><a href="/w/index.php?title=Nonatriacontanoic_acid&action=edit&redlink=1" class="new" title="Nonatriacontanoic acid (page does not exist)">Nonatriacontanoic</a> (C39)</li> <li><a href="/w/index.php?title=Tetracontanoic_acid&action=edit&redlink=1" class="new" title="Tetracontanoic acid (page does not exist)">Tetracontanoic</a> (C40)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Omega-3_fatty_acid" title="Omega-3 fatty acid">ω−3 Unsaturated</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=5-Octenoic_acid&action=edit&redlink=1" class="new" title="5-Octenoic acid (page does not exist)">Octenoic</a> (8:1)</li> <li><a href="/w/index.php?title=7-Decenoic_acid&action=edit&redlink=1" class="new" title="7-Decenoic acid (page does not exist)">Decenoic</a> (10:1)</li> <li><a href="/w/index.php?title=4,7-Decadienoic_acid&action=edit&redlink=1" class="new" title="4,7-Decadienoic acid (page does not exist)">Decadienoic</a> (10:2)</li> <li><a href="/w/index.php?title=9-Dodecenoic_acid&action=edit&redlink=1" class="new" title="9-Dodecenoic acid (page does not exist)">Lauroleic</a> (12:1)</li> <li><a href="/w/index.php?title=6,9-Dodecadienoic_acid&action=edit&redlink=1" class="new" title="6,9-Dodecadienoic acid (page does not exist)">Laurolinoleic</a> (12:2)</li> <li><a href="/w/index.php?title=11-Tetradecenoic_acid&action=edit&redlink=1" class="new" title="11-Tetradecenoic acid (page does not exist)">Myristovaccenic</a> (14:1)</li> <li><a href="/w/index.php?title=8,11-Tetradecadienoic_acid&action=edit&redlink=1" class="new" title="8,11-Tetradecadienoic acid (page does not exist)">Myristolinoleic</a> (14:2)</li> <li><a href="/w/index.php?title=5,8,11-Tetradecatrienoic_acid&action=edit&redlink=1" class="new" title="5,8,11-Tetradecatrienoic acid (page does not exist)">Myristolinolenic</a> (14:3)</li> <li><a href="/w/index.php?title=7,10,13-Hexadecatrienoic_acid&action=edit&redlink=1" class="new" title="7,10,13-Hexadecatrienoic acid (page does not exist)">Palmitolinolenic</a> (16:3)</li> <li><a href="/w/index.php?title=4,7,10,13-Hexadecatetraenoic_acid&action=edit&redlink=1" class="new" title="4,7,10,13-Hexadecatetraenoic acid (page does not exist)">Palmitidonic</a> (16:4)</li> <li><a href="/wiki/%CE%91-Linolenic_acid" title="Α-Linolenic acid">α-Linolenic</a> (18:3)</li> <li><a href="/wiki/Stearidonic_acid" title="Stearidonic acid">Stearidonic</a> (18:4)</li> <li><a href="/wiki/%CE%91-Parinaric_acid" title="Α-Parinaric acid">α-Parinaric</a> (18:4)</li> <li><a href="/w/index.php?title=11,14,17-Eicosatrienoic_acid&action=edit&redlink=1" class="new" title="11,14,17-Eicosatrienoic acid (page does not exist)">Dihomo-α-linolenic</a> (20:3)</li> <li><a href="/wiki/Eicosatetraenoic_acid" title="Eicosatetraenoic acid">Eicosatetraenoic</a> (20:4)</li> <li><a href="/wiki/Eicosapentaenoic_acid" title="Eicosapentaenoic acid">Eicosapentaenoic</a> (20:5)</li> <li><a href="/wiki/Docosapentaenoic_acid" title="Docosapentaenoic acid">Clupanodonic</a> (22:5)</li> <li><a href="/wiki/Docosahexaenoic_acid" title="Docosahexaenoic acid">Docosahexaenoic</a> (22:6)</li> <li><a href="/w/index.php?title=9,12,15,18,21-Tetracosapentaenoic_acid&action=edit&redlink=1" class="new" title="9,12,15,18,21-Tetracosapentaenoic acid (page does not exist)">9,12,15,18,21-Tetracosapentaenoic</a> (24:5)</li> <li><a href="/w/index.php?title=6,9,12,15,18,21-Tetracosahexaenoic_acid&action=edit&redlink=1" class="new" title="6,9,12,15,18,21-Tetracosahexaenoic acid (page does not exist)">6,9,12,15,18,21-Tetracosahexaenoic</a> (24:6)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/w/index.php?title=Omega-5_fatty_acid&action=edit&redlink=1" class="new" title="Omega-5 fatty acid (page does not exist)">ω−5 Unsaturated</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Myristoleic_acid" title="Myristoleic acid">Myristoleic</a> (14:1)</li> <li><a href="/w/index.php?title=11-Hexadecenoic_acid&action=edit&redlink=1" class="new" title="11-Hexadecenoic acid (page does not exist)">Palmitovaccenic</a> (16:1)</li> <li><a href="/wiki/%CE%91-Eleostearic_acid" title="Α-Eleostearic acid">α-Eleostearic</a> (18:3)</li> <li><a href="/wiki/%CE%92-Eleostearic_acid" title="Β-Eleostearic acid">β-Eleostearic</a> (<i>trans</i>-18:3)</li> <li><a href="/wiki/Punicic_acid" title="Punicic acid">Punicic</a> (18:3)</li> <li><a href="/w/index.php?title=7,10,13-Octadecatrienoic_acid&action=edit&redlink=1" class="new" title="7,10,13-Octadecatrienoic acid (page does not exist)">7,10,13-Octadecatrienoic</a> (18:3)</li> <li><a href="/w/index.php?title=9,12,15-Eicosatrienoic_acid&action=edit&redlink=1" class="new" title="9,12,15-Eicosatrienoic acid (page does not exist)">9,12,15-Eicosatrienoic</a> (20:3)</li> <li><a href="/w/index.php?title=6,9,12,15-Eicosatetraenoic_acid&action=edit&redlink=1" class="new" title="6,9,12,15-Eicosatetraenoic acid (page does not exist)">β-Eicosatetraenoic</a> (20:4)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Omega-6_fatty_acid" title="Omega-6 fatty acid">ω−6 Unsaturated</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=8-Tetradecenoic_acid&action=edit&redlink=1" class="new" title="8-Tetradecenoic acid (page does not exist)">8-Tetradecenoic</a> (14:1)</li> <li><a href="/w/index.php?title=12-Octadecenoic_acid&action=edit&redlink=1" class="new" title="12-Octadecenoic acid (page does not exist)">12-Octadecenoic</a> (18:1)</li> <li><a class="mw-selflink selflink">Linoleic</a> (18:2)</li> <li><a href="/wiki/Linolelaidic_acid" title="Linolelaidic acid">Linolelaidic</a> (<i>trans</i>-18:2)</li> <li><a href="/wiki/Gamma-Linolenic_acid" class="mw-redirect" title="Gamma-Linolenic acid">γ-Linolenic</a> (18:3)</li> <li><a href="/wiki/Calendic_acid" title="Calendic acid">Calendic</a> (18:3)</li> <li><a href="/wiki/Pinolenic_acid" title="Pinolenic acid">Pinolenic</a> (18:3)</li> <li><a href="/w/index.php?title=Dihomo-linoleic_acid&action=edit&redlink=1" class="new" title="Dihomo-linoleic acid (page does not exist)">Dihomo-linoleic</a> (20:2)</li> <li><a href="/wiki/Dihomo-%CE%B3-linolenic_acid" title="Dihomo-γ-linolenic acid">Dihomo-γ-linolenic</a> (20:3)</li> <li><a href="/wiki/Sciadonic_acid" title="Sciadonic acid">Sciadonic</a> (20:3)</li> <li><a href="/wiki/Arachidonic_acid" title="Arachidonic acid">Arachidonic</a> (20:4)</li> <li><a href="/wiki/Docosatetraenoic_acid" title="Docosatetraenoic acid">Adrenic</a> (22:4)</li> <li><a href="/wiki/Docosapentaenoic_acid" title="Docosapentaenoic acid">Osbond</a> (22:5)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Omega-7_fatty_acid" title="Omega-7 fatty acid">ω−7 Unsaturated</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Palmitoleic_acid" title="Palmitoleic acid">Palmitoleic</a> (16:1)</li> <li><a href="/wiki/Vaccenic_acid" title="Vaccenic acid">Vaccenic</a> (18:1)</li> <li><a href="/wiki/Rumenic_acid" title="Rumenic acid">Rumenic</a> (18:2)</li> <li><a href="/wiki/Paullinic_acid" title="Paullinic acid">Paullinic</a> (20:1)</li> <li><a href="/w/index.php?title=7,10,13-Eicosatrienoic_acid&action=edit&redlink=1" class="new" title="7,10,13-Eicosatrienoic acid (page does not exist)">7,10,13-Eicosatrienoic</a> (20:3)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Omega-9_fatty_acid" title="Omega-9 fatty acid">ω−9 Unsaturated</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Oleic_acid" title="Oleic acid">Oleic</a> (18:1)</li> <li><a href="/wiki/Elaidic_acid" title="Elaidic acid">Elaidic</a> (<i>trans</i>-18:1)</li> <li><a href="/wiki/11-Eicosenoic_acid" title="11-Eicosenoic acid">Gondoic</a> (20:1)</li> <li><a href="/wiki/Erucic_acid" title="Erucic acid">Erucic</a> (22:1)</li> <li><a href="/wiki/Nervonic_acid" title="Nervonic acid">Nervonic</a> (24:1)</li> <li><a href="/w/index.php?title=8,11-Eicosadienoic_acid&action=edit&redlink=1" class="new" title="8,11-Eicosadienoic acid (page does not exist)">8,11-Eicosadienoic</a> (20:2)</li> <li><a href="/wiki/Mead_acid" title="Mead acid">Mead</a> (20:3)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/w/index.php?title=Omega-10_fatty_acid&action=edit&redlink=1" class="new" title="Omega-10 fatty acid (page does not exist)">ω−10 Unsaturated</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Sapienic_acid" title="Sapienic acid">Sapienic</a> (16:1)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/w/index.php?title=Omega-11_fatty_acid&action=edit&redlink=1" class="new" title="Omega-11 fatty acid (page does not exist)">ω−11 Unsaturated</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Gadoleic_acid" title="Gadoleic acid">Gadoleic</a> (20:1)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/w/index.php?title=Omega-12_fatty_acid&action=edit&redlink=1" class="new" title="Omega-12 fatty acid (page does not exist)">ω−12 Unsaturated</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=4-Hexadecenoic_acid&action=edit&redlink=1" class="new" title="4-Hexadecenoic acid (page does not exist)">4-Hexadecenoic</a> (16:1)</li> <li><a href="/wiki/Petroselinic_acid" title="Petroselinic acid">Petroselinic</a> (18:1)</li> <li><a href="/w/index.php?title=8-Eicosenoic_acid&action=edit&redlink=1" class="new" title="8-Eicosenoic acid (page does not exist)">8-Eicosenoic</a> (20:1)</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="Palm_oil" style="padding:3px"><table class="nowraplinks hlist mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Palm_oil" title="Template:Palm oil"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Palm_oil" title="Template talk:Palm oil"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Palm_oil" title="Special:EditPage/Template:Palm oil"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Palm_oil" style="font-size:114%;margin:0 4em"><a href="/wiki/Palm_oil" title="Palm oil">Palm oil</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_plants_known_as_oil_palm" title="List of plants known as oil palm">Oil palms</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i><a href="/wiki/Attalea_(plant)" title="Attalea (plant)">Attalea</a></i> <ul><li><i><a href="/wiki/Attalea_maripa" title="Attalea maripa">A. maripa</a></i></li> <li><i><a href="/wiki/Attalea_speciosa" title="Attalea speciosa">A. speciosa</a></i></li></ul></li> <li><i><a href="/wiki/Elaeis" title="Elaeis">Elaeis</a></i> <ul><li><i><a href="/wiki/Elaeis_guineensis" title="Elaeis guineensis">E. guineesis</a></i></li> <li><i><a href="/wiki/Elaeis_oleifera" title="Elaeis oleifera">E. oleifera</a></i></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Elaeis_guineensis#Pests" title="Elaeis guineensis">Diseases and<br />pests</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Bagworm_moth" title="Bagworm moth">Bagworm moth</a></li> <li>Basal stem rot (<i><a href="/wiki/Ganoderma_orbiforme" title="Ganoderma orbiforme">Ganoderma orbiforme</a></i>)</li> <li><a href="/wiki/Cadang-cadang" title="Cadang-cadang">Cadang-cadang disease</a></li> <li>Little leaf syndrome <ul><li><i><a href="/wiki/Oryctes_rhinoceros" title="Oryctes rhinoceros">Oryctes rhinoceros</a></i></li> <li><i><a href="/wiki/Rhynchophorus_palmarum" title="Rhynchophorus palmarum">Rhynchophorus palmarum</a></i></li></ul></li> <li>Oil palm bunch moth <ul><li><i><a href="/wiki/Tirathaba_mundella" title="Tirathaba mundella">Tirathaba mundella</a></i></li> <li><i><a href="/wiki/Tirathaba_rufivena" title="Tirathaba rufivena">Tirathaba rufivena</a></i></li></ul></li> <li>Red ring disease (<i><a href="/wiki/Bursaphelenchus_cocophilus" title="Bursaphelenchus cocophilus">Bursaphelenchus cocophilus</a></i>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Components</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Fruit_(plant_structure)#Mesocarp" title="Fruit (plant structure)">Mesocarp</a></li> <li><a href="/wiki/Palm_kernel" title="Palm kernel">Palm kernel</a> <ul><li><a href="/wiki/Lauric_acid" title="Lauric acid">lauric acid</a></li> <li><a href="/wiki/Palm_kernel_oil" title="Palm kernel oil">oil</a></li></ul></li> <li><a href="/wiki/Palm_oil" title="Palm oil">Palm oil</a> <ul><li><a class="mw-selflink selflink">linoleic acid</a></li> <li><a href="/wiki/Myristic_acid" title="Myristic acid">myristic acid</a></li> <li><a href="/wiki/Oleic_acid" title="Oleic acid">oleic acid</a></li> <li><a href="/wiki/Palmitic_acid" title="Palmitic acid">palmitic acid</a></li> <li><a href="/wiki/Stearic_acid" title="Stearic acid">stearic acid</a></li> <li><a href="/wiki/Palm_stearin" title="Palm stearin">stearin</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Processes</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Biodiesel_production" title="Biodiesel production">Biodiesel production</a></li> <li><a href="/wiki/Fat_hydrogenation" title="Fat hydrogenation">Fat hydrogenation</a></li> <li><a href="/wiki/Fractionation" title="Fractionation">Fractionation</a></li> <li><a href="/wiki/Hydrolysis" title="Hydrolysis">Hydrolysis</a></li> <li><a href="/wiki/Mill_(grinding)" title="Mill (grinding)">Milling</a></li> <li><a href="/wiki/Saponification" title="Saponification">Saponification</a></li> <li><a href="/wiki/Transesterification" title="Transesterification">Transesterification</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Products</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Biodiesel" title="Biodiesel">Biodiesel</a> <ul><li><a href="/wiki/Biodiesel_by_region" title="Biodiesel by region">by region</a></li> <li><a href="/wiki/Neste_Renewable_Diesel" title="Neste Renewable Diesel">Neste</a></li></ul></li> <li><a href="/wiki/Bioplastic" title="Bioplastic">Bioplastics</a></li> <li><a href="/wiki/Cellulosic_ethanol" title="Cellulosic ethanol">Cellulosic ethanol</a></li> <li><a href="/wiki/Girl_Scout_Cookies" title="Girl Scout Cookies">Girl Scout Cookies</a></li> <li><a href="/wiki/Oleochemistry" title="Oleochemistry">Oleochemicals</a></li> <li><a href="/wiki/Vegetable_oil" title="Vegetable oil">Vegetable oil</a> <ul><li><a href="/wiki/Cooking_oil" title="Cooking oil">cooking</a></li> <li><a href="/wiki/Vegetable_oil_fuel" title="Vegetable oil fuel">fuel</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Organisations</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%;font-weight:normal;">Producers</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Bumitama_Agri" title="Bumitama Agri">Bumitama Agri</a></li> <li><a href="/wiki/Cargill" title="Cargill">Cargill</a></li> <li><a href="/wiki/Carson_Cumberbatch" title="Carson Cumberbatch">Carson Cumberbatch</a></li> <li><a href="/wiki/Equatorial_Palm_Oil" title="Equatorial Palm Oil">Equatorial Palm Oil</a></li> <li><a href="/wiki/Feronia_Inc." title="Feronia Inc.">Feronia Inc.</a></li> <li><a href="/wiki/FGV_Holdings" title="FGV Holdings">FGV Holdings</a></li> <li><a href="/wiki/IOI_Group" title="IOI Group">IOI Group</a></li> <li><a href="/wiki/Kuala_Lumpur_Kepong_Berhad" title="Kuala Lumpur Kepong Berhad">Kuala Lumpur Kepong Berhad</a></li> <li><a href="/wiki/Sime_Darby" title="Sime Darby">Sime Darby</a></li> <li><a href="/wiki/TH_Plantations" title="TH Plantations">TH Plantations</a></li> <li><a href="/wiki/Wilmar_International" title="Wilmar International">Wilmar International</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;font-weight:normal;">Buyers / processors</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/AAK_(company)" title="AAK (company)">AAK</a> <ul><li><a href="/wiki/GreenPalm" title="GreenPalm">GreenPalm</a></li></ul></li> <li><a href="/wiki/Neste" title="Neste">Neste</a></li> <li><a href="/wiki/Unilever" title="Unilever">Unilever</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;font-weight:normal;">Governmental /<br />non-governmental</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/FELCRA_Berhad" title="FELCRA Berhad">FELCRA Berhad</a></li> <li><a href="/wiki/Federal_Land_Development_Authority" title="Federal Land Development Authority">Federal Land Development Authority</a></li> <li><a href="/wiki/Indonesia_Commodity_and_Derivatives_Exchange" title="Indonesia Commodity and Derivatives Exchange">Indonesia Commodity and Derivatives Exchange</a></li> <li><a href="/wiki/Malaysia_Derivatives_Exchange" title="Malaysia Derivatives Exchange">Malaysia Derivatives Exchange</a></li> <li><a href="/wiki/Malaysian_Palm_Oil_Board" title="Malaysian Palm Oil Board">Malaysian Palm Oil Board</a></li> <li><a href="/wiki/Roundtable_on_Sustainable_Palm_Oil" title="Roundtable on Sustainable Palm Oil">Roundtable on Sustainable Palm Oil</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Policies, impacts<br />and debates</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Biofuel_policy_of_Malaysia" title="Biofuel policy of Malaysia">Biofuel policy of Malaysia</a></li> <li><a href="/wiki/Certified_sustainable_palm_oil" class="mw-redirect" title="Certified sustainable palm oil">Certified sustainable palm oil</a></li> <li><a href="/wiki/Deforestation_by_continent" title="Deforestation by continent">Deforestation by continent</a> <ul><li><a href="/wiki/Southeast_Asian_haze" title="Southeast Asian haze">Southeast Asian haze</a></li></ul></li> <li><a href="/wiki/Environmental_impact_of_biodiesel" class="mw-redirect" title="Environmental impact of biodiesel">Environmental impact of biodiesel</a></li> <li><a href="/wiki/Food_vs._fuel" title="Food vs. fuel">Food vs. fuel</a></li> <li><a href="/wiki/Issues_relating_to_biofuels" title="Issues relating to biofuels">Issues relating to biofuels</a></li> <li><a href="/wiki/Social_and_environmental_impact_of_palm_oil" title="Social and environmental impact of palm oil">Social and environmental impact of palm oil</a></li> <li><a href="/wiki/Vegetable_oils_as_alternative_energy" title="Vegetable oils as alternative energy">Vegetable oils as alternative energy</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">By country</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Agriculture_in_Colombia#Palm_oil" title="Agriculture in Colombia">Colombia</a></li> <li><a href="/wiki/Palm_oil_production_in_Indonesia" title="Palm oil production in Indonesia">Indonesia</a></li> <li><a href="/wiki/Palm_oil_production_in_Malaysia" title="Palm oil production in Malaysia">Malaysia</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <ul><li><span class="noviewer" typeof="mw:File"><span title="Category"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/16px-Symbol_category_class.svg.png" decoding="async" width="16" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/23px-Symbol_category_class.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/31px-Symbol_category_class.svg.png 2x" data-file-width="180" data-file-height="185" /></span></span> <b><a href="/wiki/Category:Oil_palm" title="Category:Oil palm">Category</a></b> <ul><li><b><a href="/wiki/Category:Palm_oil_production_by_country" title="Category:Palm oil production by country">by country</a></b></li></ul></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="Prostanoid_signaling_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:Prostanoid_signaling_modulators" title="Template:Prostanoid signaling modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Prostanoid_signaling_modulators" title="Template talk:Prostanoid signaling modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Prostanoid_signaling_modulators" title="Special:EditPage/Template:Prostanoid signaling modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Prostanoid_signaling_modulators" style="font-size:114%;margin:0 4em"><a href="/wiki/Prostanoid" title="Prostanoid">Prostanoid</a> <a href="/wiki/Cell_signaling" title="Cell signaling">signaling</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/Receptor_(biochemistry)" title="Receptor (biochemistry)">Receptor</a><br /><small>(<a href="/wiki/Ligand_(biochemistry)" title="Ligand (biochemistry)">ligands</a>)</small></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:5em;;text-align:center;"><a href="/wiki/Prostaglandin_D2_receptor" title="Prostaglandin D2 receptor"><abbr title="Prostaglandin D2 receptor">DP (D<sub>2</sub>)</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 Prostaglandin D2 receptor</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="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:5em;;text-align:center;"><a href="/wiki/Prostaglandin_D2_receptor_1" class="mw-redirect" title="Prostaglandin D2 receptor 1"><abbr title="Prostaglandin D2 receptor 1">DP<sub>1</sub></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 Prostaglandin D2 receptor 1</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Agonists:</b> <a href="/wiki/Prostaglandin_D2" title="Prostaglandin D2">Prostaglandin D<sub>2</sub></a></li> <li><a href="/wiki/Treprostinil" title="Treprostinil">Treprostinil</a></li></ul> <ul><li><b>Antagonists:</b> <a href="/w/index.php?title=Asapiprant&action=edit&redlink=1" class="new" title="Asapiprant (page does not exist)">Asapiprant</a></li> <li><a href="/wiki/Laropiprant" title="Laropiprant">Laropiprant</a></li> <li><a href="/w/index.php?title=Vidupiprant&action=edit&redlink=1" class="new" title="Vidupiprant (page does not exist)">Vidupiprant</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:5em;;text-align:center;"><a href="/wiki/Prostaglandin_D2_receptor_2" class="mw-redirect" title="Prostaglandin D2 receptor 2"><abbr title="Prostaglandin D2 receptor 2">DP<sub>2</sub></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 Prostaglandin D2 receptor 2</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Agonists:</b> <a href="/wiki/Indometacin" title="Indometacin">Indometacin</a></li> <li><a href="/wiki/Prostaglandin_D2" title="Prostaglandin D2">Prostaglandin D<sub>2</sub></a></li></ul> <ul><li><b>Antagonists:</b> <a href="/w/index.php?title=ADC-3680&action=edit&redlink=1" class="new" title="ADC-3680 (page does not exist)">ADC-3680</a></li> <li><a href="/w/index.php?title=AZD-1981&action=edit&redlink=1" class="new" title="AZD-1981 (page does not exist)">AZD-1981</a></li> <li><a href="/w/index.php?title=Bay_U3405&action=edit&redlink=1" class="new" title="Bay U3405 (page does not exist)">Bay U3405</a></li> <li><a href="/wiki/Fevipiprant" title="Fevipiprant">Fevipiprant</a></li> <li><a href="/w/index.php?title=MK-1029&action=edit&redlink=1" class="new" title="MK-1029 (page does not exist)">MK-1029</a></li> <li><a href="/w/index.php?title=MK-7246&action=edit&redlink=1" class="new" title="MK-7246 (page does not exist)">MK-7246</a></li> <li><a href="/w/index.php?title=QAV-680&action=edit&redlink=1" class="new" title="QAV-680 (page does not exist)">QAV-680</a></li> <li><a href="/wiki/Ramatroban" title="Ramatroban">Ramatroban</a></li> <li><a href="/wiki/Setipiprant" title="Setipiprant">Setipiprant</a></li> <li><a href="/w/index.php?title=Timapiprant&action=edit&redlink=1" class="new" title="Timapiprant (page does not exist)">Timapiprant</a></li> <li><a href="/w/index.php?title=TM30089&action=edit&redlink=1" class="new" title="TM30089 (page does not exist)">TM30089</a></li> <li><a href="/w/index.php?title=Vidupiprant&action=edit&redlink=1" class="new" title="Vidupiprant (page does not exist)">Vidupiprant</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:5em;;text-align:center;"><a href="/wiki/Prostaglandin_E2_receptor" title="Prostaglandin E2 receptor"><abbr title="Prostaglandin E2 receptor">EP (E<sub>2</sub>)</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 Prostaglandin E2 receptor</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="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:5em;;text-align:center;"><a href="/wiki/Prostaglandin_EP1_receptor" title="Prostaglandin EP1 receptor"><abbr title="Prostaglandin EP1 receptor">EP<sub>1</sub></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 Prostaglandin EP1 receptor</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Agonists:</b> <a href="/wiki/Beraprost" title="Beraprost">Beraprost</a></li> <li><a href="/wiki/Enprostil" title="Enprostil">Enprostil</a></li> <li><a href="/wiki/Iloprost" title="Iloprost">Iloprost (ciloprost)</a></li> <li><a href="/wiki/Latanoprost" title="Latanoprost">Latanoprost</a></li> <li><a href="/wiki/Lubiprostone" title="Lubiprostone">Lubiprostone</a></li> <li><a href="/wiki/Misoprostol" title="Misoprostol">Misoprostol</a></li> <li><a href="/wiki/Prostaglandin_E1" title="Prostaglandin E1">Prostaglandin E<sub>1</sub> (alprostadil)</a></li> <li><a href="/wiki/Prostaglandin_E2" title="Prostaglandin E2">Prostaglandin E<sub>2</sub> (dinoprostone)</a></li> <li><a href="/wiki/Sulprostone" title="Sulprostone">Sulprostone</a></li></ul> <ul><li><b>Antagonists:</b> <a href="/w/index.php?title=AH-6809&action=edit&redlink=1" class="new" title="AH-6809 (page does not exist)">AH-6809</a></li> <li><a href="/w/index.php?title=ONO-8130&action=edit&redlink=1" class="new" title="ONO-8130 (page does not exist)">ONO-8130</a></li> <li><a href="/w/index.php?title=SC-19220&action=edit&redlink=1" class="new" title="SC-19220 (page does not exist)">SC-19220</a></li> <li><a href="/w/index.php?title=SC-51089&action=edit&redlink=1" class="new" title="SC-51089 (page does not exist)">SC-51089</a></li> <li><a href="/w/index.php?title=SC-51322&action=edit&redlink=1" class="new" title="SC-51322 (page does not exist)">SC-51322</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:5em;;text-align:center;"><a href="/wiki/Prostaglandin_EP2_receptor" title="Prostaglandin EP2 receptor"><abbr title="Prostaglandin EP2 receptor">EP<sub>2</sub></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 Prostaglandin EP2 receptor</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Agonists:</b> <a href="/w/index.php?title=Butaprost&action=edit&redlink=1" class="new" title="Butaprost (page does not exist)">Butaprost</a></li> <li><a href="/wiki/Misoprostol" title="Misoprostol">Misoprostol</a></li> <li><a href="/wiki/Prostaglandin_E1" title="Prostaglandin E1">Prostaglandin E<sub>1</sub> (alprostadil)</a></li> <li><a href="/wiki/Prostaglandin_E2" title="Prostaglandin E2">Prostaglandin E<sub>2</sub> (dinoprostone)</a></li> <li><a href="/wiki/Treprostinil" title="Treprostinil">Treprostinil</a></li></ul> <ul><li><b>Antagonists:</b> <a href="/w/index.php?title=AH-6809&action=edit&redlink=1" class="new" title="AH-6809 (page does not exist)">AH-6809</a></li> <li><a href="/w/index.php?title=PF-04418948&action=edit&redlink=1" class="new" title="PF-04418948 (page does not exist)">PF-04418948</a></li> <li><a href="/w/index.php?title=TG_4-155&action=edit&redlink=1" class="new" title="TG 4-155 (page does not exist)">TG 4-155</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:5em;;text-align:center;"><a href="/wiki/Prostaglandin_EP3_receptor" title="Prostaglandin EP3 receptor"><abbr title="Prostaglandin EP3 receptor">EP<sub>3</sub></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 Prostaglandin EP3 receptor</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Agonists:</b> <a href="/wiki/Beraprost" title="Beraprost">Beraprost</a></li> <li><a href="/w/index.php?title=Carbacyclin&action=edit&redlink=1" class="new" title="Carbacyclin (page does not exist)">Carbacyclin</a></li> <li><a href="/w/index.php?title=Cicaprost&action=edit&redlink=1" class="new" title="Cicaprost (page does not exist)">Cicaprost</a></li> <li><a href="/wiki/Enprostil" title="Enprostil">Enprostil</a></li> <li><a href="/wiki/Iloprost" title="Iloprost">Iloprost (ciloprost)</a></li> <li><a href="/w/index.php?title=Isocarbacyclin&action=edit&redlink=1" class="new" title="Isocarbacyclin (page does not exist)">Isocarbacyclin</a></li> <li><a href="/wiki/Latanoprost" title="Latanoprost">Latanoprost</a></li> <li><a href="/wiki/Misoprostol" title="Misoprostol">Misoprostol</a></li> <li><a href="/wiki/Prostaglandin_D2" title="Prostaglandin D2">Prostaglandin D<sub>2</sub></a></li> <li><a href="/wiki/Prostaglandin_E1" title="Prostaglandin E1">Prostaglandin E<sub>1</sub> (alprostadil)</a></li> <li><a href="/wiki/Prostaglandin_E2" title="Prostaglandin E2">Prostaglandin E<sub>2</sub> (dinoprostone)</a></li> <li><a href="/w/index.php?title=Remiprostol&action=edit&redlink=1" class="new" title="Remiprostol (page does not exist)">Remiprostol</a></li> <li><a href="/wiki/Ricinoleic_acid" title="Ricinoleic acid">Ricinoleic acid</a></li> <li><a href="/wiki/Sulprostone" title="Sulprostone">Sulprostone</a></li></ul> <ul><li><b>Antagonists:</b> <a href="/w/index.php?title=L-798106&action=edit&redlink=1" class="new" title="L-798106 (page does not exist)">L-798106</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:5em;;text-align:center;"><a href="/wiki/Prostaglandin_EP4_receptor" title="Prostaglandin EP4 receptor"><abbr title="Prostaglandin EP4 receptor">EP<sub>4</sub></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 Prostaglandin EP4 receptor</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Agonists:</b> <a href="/wiki/Lubiprostone" title="Lubiprostone">Lubiprostone</a></li> <li><a href="/wiki/Misoprostol" title="Misoprostol">Misoprostol</a></li> <li><a href="/wiki/Prostaglandin_E1" title="Prostaglandin E1">Prostaglandin E<sub>1</sub> (alprostadil)</a></li> <li><a href="/wiki/Prostaglandin_E2" title="Prostaglandin E2">Prostaglandin E<sub>2</sub> (dinoprostone)</a></li> <li><a href="/w/index.php?title=TCS-2510&action=edit&redlink=1" class="new" title="TCS-2510 (page does not exist)">TCS-2510</a></li></ul> <ul><li><b>Antagonists:</b> <a href="/wiki/Grapiprant" title="Grapiprant">Grapiprant</a></li> <li><a href="/w/index.php?title=GW-627368&action=edit&redlink=1" class="new" title="GW-627368 (page does not exist)">GW-627368</a></li> <li><a href="/w/index.php?title=L-161982&action=edit&redlink=1" class="new" title="L-161982 (page does not exist)">L-161982</a></li> <li><a href="/w/index.php?title=ONO-AE3-208&action=edit&redlink=1" class="new" title="ONO-AE3-208 (page does not exist)">ONO-AE3-208</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:5em;;text-align:center;">Unsorted</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Agonists:</b> <a href="/w/index.php?title=16,16-Dimethyl_Prostaglandin_E2&action=edit&redlink=1" class="new" title="16,16-Dimethyl Prostaglandin E2 (page does not exist)">16,16-Dimethyl Prostaglandin E<sub>2</sub></a></li> <li><a href="/w/index.php?title=Aganepag&action=edit&redlink=1" class="new" title="Aganepag (page does not exist)">Aganepag</a></li> <li><a href="/wiki/Carboprost" title="Carboprost">Carboprost</a></li> <li><a href="/w/index.php?title=Evatanepag&action=edit&redlink=1" class="new" title="Evatanepag (page does not exist)">Evatanepag</a></li> <li><a href="/wiki/Gemeprost" title="Gemeprost">Gemeprost</a></li> <li><a href="/w/index.php?title=Nocloprost&action=edit&redlink=1" class="new" title="Nocloprost (page does not exist)">Nocloprost</a></li> <li><a href="/wiki/Omidenepag" title="Omidenepag">Omidenepag</a></li> <li><a href="/wiki/Prostaglandin_F2%CE%B1" class="mw-redirect" title="Prostaglandin F2α">Prostaglandin F<sub>2α</sub> (dinoprost)</a></li> <li><a href="/w/index.php?title=Simenepag&action=edit&redlink=1" class="new" title="Simenepag (page does not exist)">Simenepag</a></li> <li><a href="/w/index.php?title=Taprenepag&action=edit&redlink=1" class="new" title="Taprenepag (page does not exist)">Taprenepag</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:5em;;text-align:center;"><a href="/wiki/Prostaglandin_F_receptor" title="Prostaglandin F receptor"><abbr title="Prostaglandin F receptor">FP (F<sub>2α</sub>)</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 Prostaglandin F receptor</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Agonists:</b> <a href="/wiki/Alfaprostol" title="Alfaprostol">Alfaprostol</a></li> <li><a href="/wiki/Bimatoprost" title="Bimatoprost">Bimatoprost</a></li> <li><a href="/wiki/Carboprost" title="Carboprost">Carboprost</a></li> <li><a href="/wiki/Cloprostenol" title="Cloprostenol">Cloprostenol</a></li> <li><a href="/wiki/Enprostil" title="Enprostil">Enprostil</a></li> <li><a href="/w/index.php?title=Fluprostenol&action=edit&redlink=1" class="new" title="Fluprostenol (page does not exist)">Fluprostenol</a></li> <li><a href="/wiki/Latanoprost" title="Latanoprost">Latanoprost</a></li> <li><a href="/wiki/Prostaglandin_D2" title="Prostaglandin D2">Prostaglandin D<sub>2</sub></a></li> <li><a href="/wiki/Prostaglandin_F2%CE%B1" class="mw-redirect" title="Prostaglandin F2α">Prostaglandin F<sub>2α</sub> (dinoprost)</a></li> <li><a href="/w/index.php?title=Sulotroban&action=edit&redlink=1" class="new" title="Sulotroban (page does not exist)">Sulotroban</a></li> <li><a href="/wiki/Tafluprost" title="Tafluprost">Tafluprost</a></li> <li><a href="/wiki/Travoprost" title="Travoprost">Travoprost</a></li> <li><a href="/wiki/Unoprostone" title="Unoprostone">Unoprostone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:5em;;text-align:center;"><a href="/wiki/Prostacyclin_receptor" title="Prostacyclin receptor"><abbr title="Prostacyclin receptor">IP (I<sub>2</sub>)</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 Prostacyclin receptor</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Agonists:</b> <a href="/w/index.php?title=ACT-333679&action=edit&redlink=1" class="new" title="ACT-333679 (page does not exist)">ACT-333679</a></li> <li><a href="/w/index.php?title=AFP-07&action=edit&redlink=1" class="new" title="AFP-07 (page does not exist)">AFP-07</a></li> <li><a href="/wiki/Beraprost" title="Beraprost">Beraprost</a></li> <li><a href="/w/index.php?title=BMY-45778&action=edit&redlink=1" class="new" title="BMY-45778 (page does not exist)">BMY-45778</a></li> <li><a href="/w/index.php?title=Carbacyclin&action=edit&redlink=1" class="new" title="Carbacyclin (page does not exist)">Carbacyclin</a></li> <li><a href="/w/index.php?title=Cicaprost&action=edit&redlink=1" class="new" title="Cicaprost (page does not exist)">Cicaprost</a></li> <li><a href="/wiki/Iloprost" title="Iloprost">Iloprost (ciloprost)</a></li> <li><a href="/w/index.php?title=Isocarbacyclin&action=edit&redlink=1" class="new" title="Isocarbacyclin (page does not exist)">Isocarbacyclin</a></li> <li><a href="/w/index.php?title=MRE-269&action=edit&redlink=1" class="new" title="MRE-269 (page does not exist)">MRE-269</a></li> <li><a href="/w/index.php?title=NS-304&action=edit&redlink=1" class="new" title="NS-304 (page does not exist)">NS-304</a></li> <li><a href="/wiki/Prostacyclin" title="Prostacyclin">Prostacyclin (prostaglandin I<sub>2</sub>, epoprostenol)</a></li> <li><a href="/wiki/Prostaglandin_E1" title="Prostaglandin E1">Prostaglandin E<sub>1</sub> (alprostadil)</a></li> <li><a href="/w/index.php?title=Ralinepag&action=edit&redlink=1" class="new" title="Ralinepag (page does not exist)">Ralinepag</a></li> <li><a href="/wiki/Selexipag" title="Selexipag">Selexipag</a></li> <li><a href="/w/index.php?title=Taprostene&action=edit&redlink=1" class="new" title="Taprostene (page does not exist)">Taprostene</a></li> <li><a href="/w/index.php?title=TRA-418&action=edit&redlink=1" class="new" title="TRA-418 (page does not exist)">TRA-418</a></li> <li><a href="/wiki/Treprostinil" title="Treprostinil">Treprostinil</a></li></ul> <ul><li><b>Antagonists:</b> <a href="/w/index.php?title=RO1138452&action=edit&redlink=1" class="new" title="RO1138452 (page does not exist)">RO1138452</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:5em;;text-align:center;"><a href="/wiki/Thromboxane_receptor" title="Thromboxane receptor"><abbr title="Thromboxane receptor">TP (TX<sub>A2</sub>)</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 Thromboxane receptor</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Agonists:</b> <a href="/w/index.php?title=Carbocyclic_thromboxane_A2&action=edit&redlink=1" class="new" title="Carbocyclic thromboxane A2 (page does not exist)">Carbocyclic thromboxane A<sub>2</sub></a></li> <li><a href="/w/index.php?title=I-BOP&action=edit&redlink=1" class="new" title="I-BOP (page does not exist)">I-BOP</a></li> <li><a href="/wiki/Thromboxane_A2" title="Thromboxane A2">Thromboxane A<sub>2</sub></a></li> <li><a href="/wiki/U-46619" class="mw-redirect" title="U-46619">U-46619</a></li> <li><a href="/w/index.php?title=Vapiprost&action=edit&redlink=1" class="new" title="Vapiprost (page does not exist)">Vapiprost</a></li></ul> <ul><li><b>Antagonists:</b> <a href="/wiki/12-Hydroxyeicosatetraenoic_acid" title="12-Hydroxyeicosatetraenoic acid">12-HETE</a></li> <li><a href="/w/index.php?title=13-APA&action=edit&redlink=1" class="new" title="13-APA (page does not exist)">13-APA</a></li> <li><a href="/w/index.php?title=AA-2414&action=edit&redlink=1" class="new" title="AA-2414 (page does not exist)">AA-2414</a></li> <li><a href="/wiki/Argatroban" title="Argatroban">Argatroban</a></li> <li><a href="/w/index.php?title=Bay_U3405&action=edit&redlink=1" class="new" title="Bay U3405 (page does not exist)">Bay U3405</a></li> <li><a href="/w/index.php?title=BMS-180,291&action=edit&redlink=1" class="new" title="BMS-180,291 (page does not exist)">BMS-180,291</a></li> <li><a href="/w/index.php?title=Daltroban&action=edit&redlink=1" class="new" title="Daltroban (page does not exist)">Daltroban</a></li> <li><a href="/w/index.php?title=Domitroban&action=edit&redlink=1" class="new" title="Domitroban (page does not exist)">Domitroban</a></li> <li><a href="/w/index.php?title=EP-045&action=edit&redlink=1" class="new" title="EP-045 (page does not exist)">EP-045</a></li> <li><a href="/w/index.php?title=GR-32191&action=edit&redlink=1" class="new" title="GR-32191 (page does not exist)">GR-32191</a></li> <li><a href="/w/index.php?title=ICI-185282&action=edit&redlink=1" class="new" title="ICI-185282 (page does not exist)">ICI-185282</a></li> <li><a href="/w/index.php?title=ICI-192605&action=edit&redlink=1" class="new" title="ICI-192605 (page does not exist)">ICI-192605</a></li> <li><a href="/wiki/Ifetroban" title="Ifetroban">Ifetroban</a></li> <li><a href="/w/index.php?title=Imitrodast&action=edit&redlink=1" class="new" title="Imitrodast (page does not exist)">Imitrodast</a></li> <li><a href="/w/index.php?title=L-655240&action=edit&redlink=1" class="new" title="L-655240 (page does not exist)">L-655240</a></li> <li><a href="/w/index.php?title=L-670596&action=edit&redlink=1" class="new" title="L-670596 (page does not exist)">L-670596</a></li> <li><a href="/w/index.php?title=Linotroban&action=edit&redlink=1" class="new" title="Linotroban (page does not exist)">Linotroban</a></li> <li><a href="/w/index.php?title=Mipitroban&action=edit&redlink=1" class="new" title="Mipitroban (page does not exist)">Mipitroban</a></li> <li><a href="/w/index.php?title=ONO-3708&action=edit&redlink=1" class="new" title="ONO-3708 (page does not exist)">ONO-3708</a></li> <li><a href="/w/index.php?title=ONO-11120&action=edit&redlink=1" class="new" title="ONO-11120 (page does not exist)">ONO-11120</a></li> <li><a href="/wiki/Picotamide" title="Picotamide">Picotamide</a></li> <li><a href="/w/index.php?title=Pinane_thromboxane_A2&action=edit&redlink=1" class="new" title="Pinane thromboxane A2 (page does not exist)">Pinane thromboxane A<sub>2</sub></a></li> <li><a href="/wiki/Ramatroban" title="Ramatroban">Ramatroban</a></li> <li><a href="/w/index.php?title=Ridogrel&action=edit&redlink=1" class="new" title="Ridogrel (page does not exist)">Ridogrel</a></li> <li><a href="/w/index.php?title=S-145&action=edit&redlink=1" class="new" title="S-145 (page does not exist)">S-145</a></li> <li><a href="/w/index.php?title=Samixogrel&action=edit&redlink=1" class="new" title="Samixogrel (page does not exist)">Samixogrel</a></li> <li><a href="/wiki/Seratrodast" title="Seratrodast">Seratrodast</a></li> <li><a href="/w/index.php?title=SQ-28,668&action=edit&redlink=1" class="new" title="SQ-28,668 (page does not exist)">SQ-28,668</a></li> <li><a href="/w/index.php?title=SQ-29,548&action=edit&redlink=1" class="new" title="SQ-29,548 (page does not exist)">SQ-29,548</a></li> <li><a href="/w/index.php?title=Sulotroban&action=edit&redlink=1" class="new" title="Sulotroban (page does not exist)">Sulotroban</a></li> <li><a href="/wiki/Terbogrel" title="Terbogrel">Terbogrel</a></li> <li><a href="/wiki/Terutroban" title="Terutroban">Terutroban</a></li> <li><a href="/w/index.php?title=TRA-418&action=edit&redlink=1" class="new" title="TRA-418 (page does not exist)">TRA-418</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:5em;;text-align:center;">Unsorted</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=Arbaprostil&action=edit&redlink=1" class="new" title="Arbaprostil (page does not exist)">Arbaprostil</a></li> <li><a href="/w/index.php?title=Ataprost&action=edit&redlink=1" class="new" title="Ataprost (page does not exist)">Ataprost</a></li> <li><a href="/w/index.php?title=Ciprostene&action=edit&redlink=1" class="new" title="Ciprostene (page does not exist)">Ciprostene</a></li> <li><a href="/w/index.php?title=Clinprost&action=edit&redlink=1" class="new" title="Clinprost (page does not exist)">Clinprost</a></li> <li><a href="/w/index.php?title=Cobiprostone&action=edit&redlink=1" class="new" title="Cobiprostone (page does not exist)">Cobiprostone</a></li> <li><a href="/w/index.php?title=Delprostenate&action=edit&redlink=1" class="new" title="Delprostenate (page does not exist)">Delprostenate</a></li> <li><a href="/w/index.php?title=Deprostil&action=edit&redlink=1" class="new" title="Deprostil (page does not exist)">Deprostil</a></li> <li><a href="/w/index.php?title=Dimoxaprost&action=edit&redlink=1" class="new" title="Dimoxaprost (page does not exist)">Dimoxaprost</a></li> <li><a href="/w/index.php?title=Doxaprost&action=edit&redlink=1" class="new" title="Doxaprost (page does not exist)">Doxaprost</a></li> <li><a href="/w/index.php?title=Ecraprost&action=edit&redlink=1" class="new" title="Ecraprost (page does not exist)">Ecraprost</a></li> <li><a href="/w/index.php?title=Eganoprost&action=edit&redlink=1" class="new" title="Eganoprost (page does not exist)">Eganoprost</a></li> <li><a href="/w/index.php?title=Enisoprost&action=edit&redlink=1" class="new" title="Enisoprost (page does not exist)">Enisoprost</a></li> <li><a href="/w/index.php?title=Eptaloprost&action=edit&redlink=1" class="new" title="Eptaloprost (page does not exist)">Eptaloprost</a></li> <li><a href="/w/index.php?title=Esuberaprost&action=edit&redlink=1" class="new" title="Esuberaprost (page does not exist)">Esuberaprost</a></li> <li><a href="/w/index.php?title=Etiproston&action=edit&redlink=1" class="new" title="Etiproston (page does not exist)">Etiproston</a></li> <li><a href="/w/index.php?title=Fenprostalene&action=edit&redlink=1" class="new" title="Fenprostalene (page does not exist)">Fenprostalene</a></li> <li><a href="/w/index.php?title=Flunoprost&action=edit&redlink=1" class="new" title="Flunoprost (page does not exist)">Flunoprost</a></li> <li><a href="/w/index.php?title=Froxiprost&action=edit&redlink=1" class="new" title="Froxiprost (page does not exist)">Froxiprost</a></li> <li><a href="/w/index.php?title=Lanproston&action=edit&redlink=1" class="new" title="Lanproston (page does not exist)">Lanproston</a></li> <li><a href="/w/index.php?title=Limaprost&action=edit&redlink=1" class="new" title="Limaprost (page does not exist)">Limaprost</a></li> <li><a href="/w/index.php?title=Luprostiol&action=edit&redlink=1" class="new" title="Luprostiol (page does not exist)">Luprostiol</a></li> <li><a href="/w/index.php?title=Meteneprost&action=edit&redlink=1" class="new" title="Meteneprost (page does not exist)">Meteneprost</a></li> <li><a href="/w/index.php?title=Mexiprostil&action=edit&redlink=1" class="new" title="Mexiprostil (page does not exist)">Mexiprostil</a></li> <li><a href="/w/index.php?title=Naxaprostene&action=edit&redlink=1" class="new" title="Naxaprostene (page does not exist)">Naxaprostene</a></li> <li><a href="/w/index.php?title=Nileprost&action=edit&redlink=1" class="new" title="Nileprost (page does not exist)">Nileprost</a></li> <li><a href="/w/index.php?title=Nocloprost&action=edit&redlink=1" class="new" title="Nocloprost (page does not exist)">Nocloprost</a></li> <li><a href="/w/index.php?title=Ornoprostil&action=edit&redlink=1" class="new" title="Ornoprostil (page does not exist)">Ornoprostil</a></li> <li><a href="/w/index.php?title=Oxoprostol&action=edit&redlink=1" class="new" title="Oxoprostol (page does not exist)">Oxoprostol</a></li> <li><a href="/w/index.php?title=Penprostene&action=edit&redlink=1" class="new" title="Penprostene (page does not exist)">Penprostene</a></li> <li><a href="/w/index.php?title=Pimilprost&action=edit&redlink=1" class="new" title="Pimilprost (page does not exist)">Pimilprost</a></li> <li><a href="/w/index.php?title=Piriprost&action=edit&redlink=1" class="new" title="Piriprost (page does not exist)">Piriprost</a></li> <li><a href="/w/index.php?title=Posaraprost&action=edit&redlink=1" class="new" title="Posaraprost (page does not exist)">Posaraprost</a></li> <li><a href="/w/index.php?title=Prostalene&action=edit&redlink=1" class="new" title="Prostalene (page does not exist)">Prostalene</a></li> <li><a href="/w/index.php?title=Rioprostil&action=edit&redlink=1" class="new" title="Rioprostil (page does not exist)">Rioprostil</a></li> <li><a href="/w/index.php?title=Rivenprost&action=edit&redlink=1" class="new" title="Rivenprost (page does not exist)">Rivenprost</a></li> <li><a href="/w/index.php?title=Rosaprostol&action=edit&redlink=1" class="new" title="Rosaprostol (page does not exist)">Rosaprostol</a></li> <li><a href="/w/index.php?title=Spiriprostil&action=edit&redlink=1" class="new" title="Spiriprostil (page does not exist)">Spiriprostil</a></li> <li><a href="/w/index.php?title=Tiaprost&action=edit&redlink=1" class="new" title="Tiaprost (page does not exist)">Tiaprost</a></li> <li><a href="/w/index.php?title=Tilsuprost&action=edit&redlink=1" class="new" title="Tilsuprost (page does not exist)">Tilsuprost</a></li> <li><a href="/w/index.php?title=Tiprostanide&action=edit&redlink=1" class="new" title="Tiprostanide (page does not exist)">Tiprostanide</a></li> <li><a href="/w/index.php?title=Trimoprostil&action=edit&redlink=1" class="new" title="Trimoprostil (page does not exist)">Trimoprostil</a></li> <li><a href="/w/index.php?title=Viprostol&action=edit&redlink=1" class="new" title="Viprostol (page does not exist)">Viprostol</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/Enzyme" title="Enzyme">Enzyme</a><br /><small>(<a href="/wiki/Enzyme_inhibitor" title="Enzyme inhibitor">inhibitors</a>)</small></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:5em;;text-align:center;"><a href="/wiki/Cyclooxygenase" title="Cyclooxygenase"><abbr title="Cyclooxygenase">COX</abbr><br />(<abbr title="prostaglandin G/H synthase">PTGS</abbr>)</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><i>Salicylic acids:</i> <a href="/wiki/Aloxiprin" title="Aloxiprin">Aloxiprin</a></li> <li><a href="/wiki/Aspirin" title="Aspirin">Aspirin (acetylsalicylic acid)</a></li> <li><a href="/wiki/Benorilate" title="Benorilate">Benorilate (benorylate)</a></li> <li><a href="/wiki/Carbasalate_calcium" title="Carbasalate calcium">Carbasalate calcium</a></li> <li><a href="/wiki/Diflunisal" title="Diflunisal">Diflunisal</a></li> <li><a href="/wiki/Dipyrocetyl" title="Dipyrocetyl">Dipyrocetyl</a></li> <li><a href="/wiki/Ethenzamide" title="Ethenzamide">Ethenzamide</a></li> <li><a href="/wiki/Guacetisal" title="Guacetisal">Guacetisal</a></li> <li><a href="/wiki/Magnesium_salicylate" title="Magnesium salicylate">Magnesium salicylate</a></li> <li><a href="/wiki/Mesalazine" title="Mesalazine">Mesalazine (5-aminosalicylic acid)</a></li> <li><a href="/wiki/Methyl_salicylate" title="Methyl salicylate">Methyl salicylate</a></li> <li><a href="/w/index.php?title=Salacetamide&action=edit&redlink=1" class="new" title="Salacetamide (page does not exist)">Salacetamide</a></li> <li><a href="/wiki/Salicin" title="Salicin">Salicin</a></li> <li><a href="/wiki/Salicylamide" title="Salicylamide">Salicylamide</a></li> <li><a href="/wiki/Salicylate" class="mw-redirect" title="Salicylate">Salicylate (salicylic acid)</a></li> <li><a href="/wiki/Salsalate" title="Salsalate">Salsalate</a></li> <li><a href="/wiki/Sodium_salicylate" title="Sodium salicylate">Sodium salicylate</a></li> <li><a href="/wiki/Triflusal" title="Triflusal">Triflusal</a>; <i>Acetic acids:</i> <a href="/wiki/Aceclofenac" title="Aceclofenac">Aceclofenac</a></li> <li><a href="/wiki/Acemetacin" title="Acemetacin">Acemetacin</a></li> <li><a href="/w/index.php?title=Aclofenac&action=edit&redlink=1" class="new" title="Aclofenac (page does not exist)">Aclofenac</a></li> <li><a href="/wiki/Amfenac" title="Amfenac">Amfenac</a></li> <li><a href="/wiki/Alclofenac" title="Alclofenac">Alclofenac</a></li> <li><a href="/wiki/Bendazac" title="Bendazac">Bendazac</a></li> <li><a href="/wiki/Bromfenac" title="Bromfenac">Bromfenac</a></li> <li><a href="/wiki/Bufexamac" title="Bufexamac">Bufexamac</a></li> <li><a href="/wiki/Bumadizone" title="Bumadizone">Bumadizone</a></li> <li><a href="/w/index.php?title=Cinmetacin&action=edit&redlink=1" class="new" title="Cinmetacin (page does not exist)">Cinmetacin</a></li> <li><a href="/w/index.php?title=Clometacin&action=edit&redlink=1" class="new" title="Clometacin (page does not exist)">Clometacin</a></li> <li><a href="/wiki/Diclofenac" title="Diclofenac">Diclofenac</a></li> <li><a href="/wiki/Difenpiramide" title="Difenpiramide">Difenpiramide</a></li> <li><a href="/wiki/Etodolac" title="Etodolac">Etodolac</a></li> <li><a href="/wiki/Felbinac" title="Felbinac">Felbinac</a></li> <li><a href="/wiki/Fenclofenac" title="Fenclofenac">Fenclofenac</a></li> <li><a href="/wiki/Fentiazac" title="Fentiazac">Fentiazac</a></li> <li><a href="/wiki/Glucametacin" title="Glucametacin">Glucametacin</a></li> <li><a href="/wiki/Indometacin" title="Indometacin">Indometacin (indomethacin)</a></li> <li><a href="/wiki/Indometacin_farnesil" title="Indometacin farnesil">Indometacin farnesil</a></li> <li><a href="/wiki/Ketorolac" title="Ketorolac">Ketorolac</a></li> <li><a href="/wiki/Lonazolac" title="Lonazolac">Lonazolac</a></li> <li><a href="/wiki/Mofezolac" title="Mofezolac">Mofezolac</a></li> <li><a href="/wiki/Nabumetone" title="Nabumetone">Nabumetone</a></li> <li><a href="/wiki/Oxametacin" title="Oxametacin">Oxametacin</a></li> <li><a href="/w/index.php?title=Oxindanac&action=edit&redlink=1" class="new" title="Oxindanac (page does not exist)">Oxindanac</a></li> <li><a href="/wiki/Proglumetacin" title="Proglumetacin">Proglumetacin</a></li> <li><a href="/wiki/Sulindac" title="Sulindac">Sulindac</a></li> <li><a href="/w/index.php?title=Sulindac_sulfide&action=edit&redlink=1" class="new" title="Sulindac sulfide (page does not exist)">Sulindac sulfide</a></li> <li><a href="/wiki/Tolmetin" title="Tolmetin">Tolmetin</a></li> <li><a href="/w/index.php?title=Zidometacin&action=edit&redlink=1" class="new" title="Zidometacin (page does not exist)">Zidometacin</a></li> <li><a href="/wiki/Zomepirac" title="Zomepirac">Zomepirac</a>; <i>Propionic acids:</i> <a href="/wiki/Alminoprofen" title="Alminoprofen">Alminoprofen</a></li> <li><a href="/wiki/Benoxaprofen" title="Benoxaprofen">Benoxaprofen</a></li> <li><a href="/w/index.php?title=Bucloxic_acid&action=edit&redlink=1" class="new" title="Bucloxic acid (page does not exist)">Bucloxic acid (blucloxate)</a></li> <li><a href="/w/index.php?title=Butibufen&action=edit&redlink=1" class="new" title="Butibufen (page does not exist)">Butibufen</a></li> <li><a href="/wiki/Carprofen" title="Carprofen">Carprofen</a></li> <li><a href="/wiki/Dexibuprofen" title="Dexibuprofen">Dexibuprofen</a></li> <li><a href="/w/index.php?title=Dexindoprofen&action=edit&redlink=1" class="new" title="Dexindoprofen (page does not exist)">Dexindoprofen</a></li> <li><a href="/wiki/Dexketoprofen" title="Dexketoprofen">Dexketoprofen</a></li> <li><a href="/wiki/Fenbufen" title="Fenbufen">Fenbufen</a></li> <li><a href="/wiki/Fenoprofen" title="Fenoprofen">Fenoprofen</a></li> <li><a href="/wiki/Flunoxaprofen" title="Flunoxaprofen">Flunoxaprofen</a></li> <li><a href="/wiki/Flurbiprofen" title="Flurbiprofen">Flurbiprofen</a></li> <li><a href="/wiki/Ibuprofen" title="Ibuprofen">Ibuprofen</a></li> <li><a href="/wiki/Ibuproxam" title="Ibuproxam">Ibuproxam</a></li> <li><a href="/wiki/Indoprofen" title="Indoprofen">Indoprofen</a></li> <li><a href="/wiki/Ketoprofen" title="Ketoprofen">Ketoprofen</a></li> <li><a href="/wiki/Loxoprofen" title="Loxoprofen">Loxoprofen</a></li> <li><a href="/wiki/Miroprofen" title="Miroprofen">Miroprofen</a></li> <li><a href="/wiki/Naproxen" title="Naproxen">Naproxen</a></li> <li><a href="/wiki/Naproxcinod" title="Naproxcinod">Naproxcinod</a></li> <li><a href="/wiki/Oxaprozin" title="Oxaprozin">Oxaprozin</a></li> <li><a href="/wiki/Pirprofen" title="Pirprofen">Pirprofen</a></li> <li><a href="/wiki/Pranoprofen" title="Pranoprofen">Pranoprofen</a></li> <li><a href="/wiki/Suprofen" title="Suprofen">Suprofen</a></li> <li><a href="/wiki/Tarenflurbil" title="Tarenflurbil">Tarenflurbil</a></li> <li><a href="/wiki/Tepoxalin" title="Tepoxalin">Tepoxalin</a></li> <li><a href="/wiki/Tiaprofenic_acid" title="Tiaprofenic acid">Tiaprofenic acid (tiaprofenate)</a></li> <li><a href="/wiki/Vedaprofen" title="Vedaprofen">Vedaprofen</a>; <i>Anthranilic acids (fenamic acids):</i> <a href="/wiki/Etofenamate" title="Etofenamate">Etofenamic acid (etofenamate)</a></li> <li><a href="/w/index.php?title=Floctafenic_acid&action=edit&redlink=1" class="new" title="Floctafenic acid (page does not exist)">Floctafenic acid (floctafenate)</a></li> <li><a href="/wiki/Flufenamic_acid" title="Flufenamic acid">Flufenamic acid (flufenamate)</a></li> <li><a href="/wiki/Meclofenamic_acid" title="Meclofenamic acid">Meclofenamic acid (meclofenamate)</a></li> <li><a href="/wiki/Mefenamic_acid" title="Mefenamic acid">Mefenamic acid (mefenamate)</a></li> <li><a href="/wiki/Morniflumate" title="Morniflumate">Morniflumic acid (morniflumate)</a></li> <li><a href="/wiki/Niflumic_acid" title="Niflumic acid">Niflumic acid (niflumate)</a></li> <li><a href="/w/index.php?title=Talinflumic_acid&action=edit&redlink=1" class="new" title="Talinflumic acid (page does not exist)">Talinflumic acid (talinflumate)</a></li> <li><a href="/wiki/Tolfenamic_acid" title="Tolfenamic acid">Tolfenamic acid (tolfenamate)</a>; <i>Pyrazolones:</i> <a href="/wiki/Azapropazone" title="Azapropazone">Azapropazone</a></li> <li><a href="/wiki/Dipyrone" class="mw-redirect" title="Dipyrone">Dipyrone</a></li> <li><a href="/wiki/Isopyrin" class="mw-redirect" title="Isopyrin">Isopyrin</a></li> <li><a href="/wiki/Oxyphenbutazone" title="Oxyphenbutazone">Oxyphenbutazone</a></li> <li><a href="/wiki/Phenylbutazone" title="Phenylbutazone">Phenylbutazone</a>; <i>Enolic acids (oxicams):</i> <a href="/wiki/Ampiroxicam" title="Ampiroxicam">Ampiroxicam</a></li> <li><a href="/wiki/Droxicam" title="Droxicam">Droxicam</a></li> <li><a href="/w/index.php?title=Enolicam&action=edit&redlink=1" class="new" title="Enolicam (page does not exist)">Enolicam</a></li> <li><a href="/wiki/Isoxicam" title="Isoxicam">Isoxicam</a></li> <li><a href="/wiki/Lornoxicam" title="Lornoxicam">Lornoxicam</a></li> <li><a href="/wiki/Meloxicam" title="Meloxicam">Meloxicam</a></li> <li><a href="/wiki/Piroxicam" title="Piroxicam">Piroxicam</a></li> <li><a href="/wiki/Tenoxicam" title="Tenoxicam">Tenoxicam</a>; <i>4-Aminoquinolines:</i> <a href="/wiki/Antrafenine" title="Antrafenine">Antrafenine</a></li> <li><a href="/wiki/Floctafenine" title="Floctafenine">Floctafenine</a></li> <li><a href="/wiki/Glafenine" title="Glafenine">Glafenine</a>; <i>Quinazolines:</i> <a href="/wiki/Fluproquazone" title="Fluproquazone">Fluproquazone</a></li> <li><a href="/wiki/Proquazone" title="Proquazone">Proquazone</a>; <i>Aminonicotinic acids:</i> <a href="/w/index.php?title=Clonixeril&action=edit&redlink=1" class="new" title="Clonixeril (page does not exist)">Clonixeril</a></li> <li><a href="/wiki/Clonixin" title="Clonixin">Clonixin</a></li> <li><a href="/wiki/Flunixin" title="Flunixin">Flunixin</a>; <i>Sulfonanilides:</i> <a href="/w/index.php?title=Flosulide&action=edit&redlink=1" class="new" title="Flosulide (page does not exist)">Flosulide</a></li> <li><a href="/wiki/Nimesulide" title="Nimesulide">Nimesulide</a>; <i>Aminophenols (anilines):</i> <a href="/wiki/Acetanilide" title="Acetanilide">Acetanilide</a></li> <li><a href="/wiki/AM404" title="AM404">AM-404 (N-arachidonoylaminophenol)</a></li> <li><a href="/wiki/Bucetin" title="Bucetin">Bucetin</a></li> <li><a href="/wiki/Paracetamol" title="Paracetamol">Paracetamol (acetaminophen)</a></li> <li><a href="/w/index.php?title=Parapropamol&action=edit&redlink=1" class="new" title="Parapropamol (page does not exist)">Parapropamol</a></li> <li><a href="/wiki/Phenacetin" title="Phenacetin">Phenacetin</a></li> <li><a href="/wiki/Propacetamol" title="Propacetamol">Propacetamol</a>; <i>Selective COX-2 inhibitors (coxibs):</i> <a href="/wiki/Apricoxib" title="Apricoxib">Apricoxib</a></li> <li><a href="/wiki/Celecoxib" title="Celecoxib">Celecoxib</a></li> <li><a href="/wiki/Cimicoxib" title="Cimicoxib">Cimicoxib</a></li> <li><a href="/wiki/Deracoxib" title="Deracoxib">Deracoxib</a></li> <li><a href="/wiki/Etoricoxib" title="Etoricoxib">Etoricoxib</a></li> <li><a href="/wiki/Firocoxib" title="Firocoxib">Firocoxib</a></li> <li><a href="/wiki/Lumiracoxib" title="Lumiracoxib">Lumiracoxib</a></li> <li><a href="/wiki/Mavacoxib" title="Mavacoxib">Mavacoxib</a></li> <li><a href="/wiki/Parecoxib" title="Parecoxib">Parecoxib</a></li> <li><a href="/wiki/Polmacoxib" title="Polmacoxib">Polmacoxib</a></li> <li><a href="/wiki/Robenacoxib" title="Robenacoxib">Robenacoxib</a></li> <li><a href="/wiki/Rofecoxib" title="Rofecoxib">Rofecoxib</a></li> <li><a href="/wiki/Tilmacoxib" title="Tilmacoxib">Tilmacoxib</a></li> <li><a href="/wiki/Valdecoxib" title="Valdecoxib">Valdecoxib</a>; <i>Others/unsorted:</i> <a href="/wiki/Anitrazafen" title="Anitrazafen">Anitrazafen</a></li> <li><a href="/w/index.php?title=Clobuzarit&action=edit&redlink=1" class="new" title="Clobuzarit (page does not exist)">Clobuzarit</a></li> <li><a href="/wiki/Curcumin" title="Curcumin">Curcumin</a></li> <li><a href="/w/index.php?title=DuP-697&action=edit&redlink=1" class="new" title="DuP-697 (page does not exist)">DuP-697</a></li> <li><a href="/w/index.php?title=FK-3311&action=edit&redlink=1" class="new" title="FK-3311 (page does not exist)">FK-3311</a></li> <li><a href="/wiki/Flumizole" title="Flumizole">Flumizole</a></li> <li><a href="/w/index.php?title=FR-122047&action=edit&redlink=1" class="new" title="FR-122047 (page does not exist)">FR-122047</a></li> <li><a href="/wiki/Glimepiride" title="Glimepiride">Glimepiride</a></li> <li><a href="/wiki/Hyperforin" title="Hyperforin">Hyperforin</a></li> <li><a href="/w/index.php?title=Itazigrel&action=edit&redlink=1" class="new" title="Itazigrel (page does not exist)">Itazigrel</a></li> <li><a href="/w/index.php?title=L-655240&action=edit&redlink=1" class="new" title="L-655240 (page does not exist)">L-655240</a></li> <li><a href="/w/index.php?title=L-670596&action=edit&redlink=1" class="new" title="L-670596 (page does not exist)">L-670596</a></li> <li><a href="/wiki/Licofelone" title="Licofelone">Licofelone</a></li> <li><a href="/wiki/Menatetrenone" title="Menatetrenone">Menatetrenone (vitamin K<sub>2</sub>)</a></li> <li><a href="/w/index.php?title=NCX-466&action=edit&redlink=1" class="new" title="NCX-466 (page does not exist)">NCX-466</a></li> <li><a href="/w/index.php?title=NCX-4040&action=edit&redlink=1" class="new" title="NCX-4040 (page does not exist)">NCX-4040</a></li> <li><a href="/wiki/NS-398" title="NS-398">NS-398</a></li> <li><a href="/wiki/Pamicogrel" title="Pamicogrel">Pamicogrel</a></li> <li><a href="/wiki/Resveratrol" title="Resveratrol">Resveratrol</a></li> <li><a href="/w/index.php?title=Romazarit&action=edit&redlink=1" class="new" title="Romazarit (page does not exist)">Romazarit</a></li> <li><a href="/wiki/Rosmarinic_acid" title="Rosmarinic acid">Rosmarinic acid</a></li> <li><a href="/wiki/Rutecarpine" title="Rutecarpine">Rutecarpine</a></li> <li><a href="/w/index.php?title=Satigrel&action=edit&redlink=1" class="new" title="Satigrel (page does not exist)">Satigrel</a></li> <li><a href="/w/index.php?title=SC-236&action=edit&redlink=1" class="new" title="SC-236 (page does not exist)">SC-236</a></li> <li><a href="/w/index.php?title=SC-560&action=edit&redlink=1" class="new" title="SC-560 (page does not exist)">SC-560</a></li> <li><a href="/w/index.php?title=SC-58125&action=edit&redlink=1" class="new" title="SC-58125 (page does not exist)">SC-58125</a></li> <li><a href="/wiki/Tenidap" title="Tenidap">Tenidap</a></li> <li><a href="/w/index.php?title=Tiflamizole&action=edit&redlink=1" class="new" title="Tiflamizole (page does not exist)">Tiflamizole</a></li> <li><a href="/w/index.php?title=Timegadine&action=edit&redlink=1" class="new" title="Timegadine (page does not exist)">Timegadine</a></li> <li><a href="/w/index.php?title=Trifenagrel&action=edit&redlink=1" class="new" title="Trifenagrel (page does not exist)">Trifenagrel</a></li> <li><a href="/w/index.php?title=Tropesin&action=edit&redlink=1" class="new" title="Tropesin (page does not exist)">Tropesin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:5em;;text-align:center;"><a href="/wiki/Prostaglandin_D_synthase" class="mw-redirect" title="Prostaglandin D synthase"><abbr title="Prostaglandin D synthase">PGD<sub>2</sub>S</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 Prostaglandin D synthase</span></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/Retinoid" title="Retinoid">Retinoids</a></li> <li><a href="/wiki/Selenium" title="Selenium">Selenium</a> (<a href="/wiki/Selenium_tetrachloride" title="Selenium tetrachloride">selenium tetrachloride</a>, <a href="/wiki/Sodium_selenite" title="Sodium selenite">sodium selenite</a>, <a href="/wiki/Selenium_disulfide" title="Selenium disulfide">selenium disulfide</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:5em;;text-align:center;"><a href="/wiki/Prostaglandin_E_synthase" title="Prostaglandin E synthase"><abbr title="Prostaglandin E synthase">PGES</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 Prostaglandin E synthase</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"><a href="/w/index.php?title=HQL-79&action=edit&redlink=1" class="new" title="HQL-79 (page does not exist)">HQL-79</a></div></td></tr><tr><th scope="row" class="navbox-group" style="width:5em;;text-align:center;"><a href="/wiki/Prostaglandin_F_synthase" title="Prostaglandin F synthase"><abbr title="Prostaglandin F synthase">PGFS</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 Prostaglandin F synthase</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"><a href="/wiki/Bimatoprost" title="Bimatoprost">Bimatoprost</a></div></td></tr><tr><th scope="row" class="navbox-group" style="width:5em;;text-align:center;"><a href="/wiki/Prostacyclin_synthase" title="Prostacyclin synthase"><abbr title="Prostacyclin synthase">PGI<sub>2</sub>S</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 Prostacyclin synthase</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"><a href="/wiki/Tranylcypromine" title="Tranylcypromine">Tranylcypromine</a></div></td></tr><tr><th scope="row" class="navbox-group" style="width:5em;;text-align:center;"><a href="/wiki/Thromboxane_A_synthase" class="mw-redirect" title="Thromboxane A synthase"><abbr title="Thromboxane A synthase">TXAS</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 Thromboxane A synthase</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=Camonagrel&action=edit&redlink=1" class="new" title="Camonagrel (page does not exist)">Camonagrel</a></li> <li><a href="/w/index.php?title=Dazmegrel&action=edit&redlink=1" class="new" title="Dazmegrel (page does not exist)">Dazmegrel</a></li> <li><a href="/wiki/Dazoxiben" title="Dazoxiben">Dazoxiben</a></li> <li><a href="/wiki/Furegrelate" title="Furegrelate">Furegrelate</a></li> <li><a href="/w/index.php?title=Isbogrel&action=edit&redlink=1" class="new" title="Isbogrel (page does not exist)">Isbogrel</a></li> <li><a href="/w/index.php?title=Midazogrel&action=edit&redlink=1" class="new" title="Midazogrel (page does not exist)">Midazogrel</a></li> <li><a href="/w/index.php?title=Nafagrel&action=edit&redlink=1" class="new" title="Nafagrel (page does not exist)">Nafagrel</a></li> <li><a href="/w/index.php?title=Nicogrelate&action=edit&redlink=1" class="new" title="Nicogrelate (page does not exist)">Nicogrelate</a></li> <li><a href="/wiki/Ozagrel" title="Ozagrel">Ozagrel</a></li> <li><a href="/wiki/Picotamide" title="Picotamide">Picotamide</a></li> <li><a href="/w/index.php?title=Pirmagrel&action=edit&redlink=1" class="new" title="Pirmagrel (page does not exist)">Pirmagrel</a></li> <li><a href="/w/index.php?title=Ridogrel&action=edit&redlink=1" class="new" title="Ridogrel (page does not exist)">Ridogrel</a></li> <li><a href="/w/index.php?title=Rolafagrel&action=edit&redlink=1" class="new" title="Rolafagrel (page does not exist)">Rolafagrel</a></li> <li><a href="/w/index.php?title=Samixogrel&action=edit&redlink=1" class="new" title="Samixogrel (page does not exist)">Samixogrel</a></li> <li><a href="/wiki/Terbogrel" title="Terbogrel">Terbogrel</a></li> <li><a href="/w/index.php?title=U63557A&action=edit&redlink=1" class="new" title="U63557A (page does not exist)">U63557A</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;">Others</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><b>Precursors:</b> <a class="mw-selflink selflink">Linoleic acid</a></li> <li><a href="/wiki/Gamma-Linolenic_acid" class="mw-redirect" title="Gamma-Linolenic acid">γ-Linolenic acid (gamolenic acid)</a></li> <li><a href="/wiki/Dihomo-%CE%B3-linolenic_acid" title="Dihomo-γ-linolenic acid">Dihomo-γ-linolenic acid</a></li> <li><a href="/wiki/Diglyceride" title="Diglyceride">Diacylglycerol</a></li> <li><a href="/wiki/Arachidonic_acid" title="Arachidonic acid">Arachidonic acid</a></li> <li><a href="/wiki/Prostaglandin_G2" title="Prostaglandin G2">Prostaglandin G<sub>2</sub></a></li> <li><a href="/wiki/Prostaglandin_H2" title="Prostaglandin H2">Prostaglandin H<sub>2</sub></a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt>See also</dt> <dd><i><a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></i></dd> <dd><i><a href="/wiki/Template:Leukotriene_signaling_modulators" title="Template:Leukotriene signaling modulators">Leukotriene signaling modulators</a></i></dd></dl> </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="Leukotriene_signaling_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:Leukotriene_signaling_modulators" title="Template:Leukotriene signaling modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Leukotriene_signaling_modulators" title="Template talk:Leukotriene signaling modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Leukotriene_signaling_modulators" title="Special:EditPage/Template:Leukotriene signaling modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Leukotriene_signaling_modulators" style="font-size:114%;margin:0 4em"><a href="/wiki/Leukotriene" title="Leukotriene">Leukotriene</a> <a href="/wiki/Cell_signaling" title="Cell signaling">signaling</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/Receptor_(biochemistry)" title="Receptor (biochemistry)">Receptor</a><br /><small>(<a href="/wiki/Ligand_(biochemistry)" title="Ligand (biochemistry)">ligands</a>)</small></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:4em;;text-align:center;"><a href="/wiki/Leukotriene_B4_receptor" title="Leukotriene B4 receptor"><abbr title="Leukotriene B4 receptor">BLT</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 Leukotriene B4 receptor</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="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:4em;;text-align:center;"><a href="/wiki/Leukotriene_B4_receptor_1" title="Leukotriene B4 receptor 1"><abbr title="Leukotriene B4 receptor 1">BLT<sub>1</sub></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 Leukotriene B4 receptor 1</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Agonists:</b> <a href="/wiki/12-Hydroxyeicosatetraenoic_acid" title="12-Hydroxyeicosatetraenoic acid">12-HETE</a></li> <li><a href="/w/index.php?title=20-Hydroxy-LTB4&action=edit&redlink=1" class="new" title="20-Hydroxy-LTB4 (page does not exist)">20-Hydroxy-LTB<sub>4</sub></a></li> <li><a href="/wiki/Leukotriene_B4" title="Leukotriene B4">Leukotriene B<sub>4</sub></a></li> <li><a href="/w/index.php?title=LY-255283&action=edit&redlink=1" class="new" title="LY-255283 (page does not exist)">LY-255283</a></li></ul> <ul><li><b>Antagonists:</b> <a href="/w/index.php?title=20-Carboxy-LTB4&action=edit&redlink=1" class="new" title="20-Carboxy-LTB4 (page does not exist)">20-Carboxy-LTB<sub>4</sub></a></li> <li><a href="/w/index.php?title=Amelubant&action=edit&redlink=1" class="new" title="Amelubant (page does not exist)">Amelubant</a></li> <li><a href="/w/index.php?title=CGS-23131&action=edit&redlink=1" class="new" title="CGS-23131 (page does not exist)">CGS-23131 (LY-223982)</a></li> <li><a href="/w/index.php?title=CGS-25019C&action=edit&redlink=1" class="new" title="CGS-25019C (page does not exist)">CGS-25019C</a></li> <li><a href="/w/index.php?title=CP-105696&action=edit&redlink=1" class="new" title="CP-105696 (page does not exist)">CP-105696</a></li> <li><a href="/w/index.php?title=CP-195543&action=edit&redlink=1" class="new" title="CP-195543 (page does not exist)">CP-195543</a></li> <li><a href="/wiki/Etalocib" title="Etalocib">Etalocib</a></li> <li><a href="/w/index.php?title=LY-293111&action=edit&redlink=1" class="new" title="LY-293111 (page does not exist)">LY-293111</a></li> <li><a href="/w/index.php?title=Moxilubant&action=edit&redlink=1" class="new" title="Moxilubant (page does not exist)">Moxilubant</a></li> <li><a href="/w/index.php?title=ONO-4057&action=edit&redlink=1" class="new" title="ONO-4057 (page does not exist)">ONO-4057</a></li> <li><a href="/w/index.php?title=RG-14893&action=edit&redlink=1" class="new" title="RG-14893 (page does not exist)">RG-14893</a></li> <li><a href="/w/index.php?title=RP-69698&action=edit&redlink=1" class="new" title="RP-69698 (page does not exist)">RP-69698</a></li> <li><a href="/w/index.php?title=SB-209247&action=edit&redlink=1" class="new" title="SB-209247 (page does not exist)">SB-209247</a></li> <li><a href="/w/index.php?title=SC-53228&action=edit&redlink=1" class="new" title="SC-53228 (page does not exist)">SC-53228</a></li> <li><a href="/w/index.php?title=Ticolubant&action=edit&redlink=1" class="new" title="Ticolubant (page does not exist)">Ticolubant</a></li> <li><a href="/w/index.php?title=U-75302&action=edit&redlink=1" class="new" title="U-75302 (page does not exist)">U-75302</a></li> <li><a href="/w/index.php?title=ZK-158252&action=edit&redlink=1" class="new" title="ZK-158252 (page does not exist)">ZK-158252</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Leukotriene_B4_receptor_2" title="Leukotriene B4 receptor 2"><abbr title="Leukotriene B4 receptor 2">BLT<sub>2</sub></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 Leukotriene B4 receptor 2</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Agonists:</b> <a href="/wiki/12-Hydroxyeicosatetraenoic_acid" title="12-Hydroxyeicosatetraenoic acid">12-HETE</a></li> <li><a href="/wiki/12-Hydroxyheptadecatrienoic_acid" title="12-Hydroxyheptadecatrienoic acid">12-HHT</a></li> <li><a href="/w/index.php?title=12-Hydroperoxy-5Z,8Z,10E,14Z-eicosatetraenoic_acid&action=edit&redlink=1" class="new" title="12-Hydroperoxy-5Z,8Z,10E,14Z-eicosatetraenoic acid (page does not exist)">12-HpETE</a></li> <li><a href="/wiki/15-Hydroxyicosatetraenoic_acid" class="mw-redirect" title="15-Hydroxyicosatetraenoic acid">15-HETE</a></li> <li><a href="/w/index.php?title=15-Hydroperoxy-5Z,8Z,11Z,13E-eicosatetraenoic_acid&action=edit&redlink=1" class="new" title="15-Hydroperoxy-5Z,8Z,11Z,13E-eicosatetraenoic acid (page does not exist)">15-HpETE</a></li> <li><a href="/w/index.php?title=20-Hydroxy-LTB4&action=edit&redlink=1" class="new" title="20-Hydroxy-LTB4 (page does not exist)">20-Hydroxy-LTB<sub>4</sub></a></li> <li><a href="/wiki/Leukotriene_B4" title="Leukotriene B4">Leukotriene B<sub>4</sub></a></li></ul> <ul><li><b>Antagonists:</b> <a href="/w/index.php?title=CP-195543&action=edit&redlink=1" class="new" title="CP-195543 (page does not exist)">CP-195543</a></li> <li><a href="/w/index.php?title=LY-255283&action=edit&redlink=1" class="new" title="LY-255283 (page does not exist)">LY-255283</a></li> <li><a href="/w/index.php?title=ZK-158252&action=edit&redlink=1" class="new" title="ZK-158252 (page does not exist)">ZK-158252</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Cysteinyl_leukotriene_receptor" title="Cysteinyl leukotriene receptor"><abbr title="Cysteinyl leukotriene receptor">CysLT</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 Cysteinyl leukotriene receptor</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="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:4em;;text-align:center;"><a href="/wiki/Cysteinyl_leukotriene_receptor_1" title="Cysteinyl leukotriene receptor 1"><abbr title="Cysteinyl leukotriene receptor 1">CysLT<sub>1</sub></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 Cysteinyl leukotriene receptor 1</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Agonists:</b> <a href="/wiki/Leukotriene_C4" title="Leukotriene C4">Leukotriene C<sub>4</sub></a></li> <li><a href="/wiki/Leukotriene_D4" title="Leukotriene D4">Leukotriene D<sub>4</sub></a></li> <li><a href="/wiki/Leukotriene_E4" title="Leukotriene E4">Leukotriene E<sub>4</sub></a></li></ul> <ul><li><b>Antagonists:</b> <a href="/wiki/Ablukast" title="Ablukast">Ablukast</a></li> <li><a href="/w/index.php?title=BAYu9773&action=edit&redlink=1" class="new" title="BAYu9773 (page does not exist)">BAYu9773</a></li> <li><a href="/w/index.php?title=BAYu9916&action=edit&redlink=1" class="new" title="BAYu9916 (page does not exist)">BAYu9916</a></li> <li><a href="/w/index.php?title=BAYx7195&action=edit&redlink=1" class="new" title="BAYx7195 (page does not exist)">BAYx7195</a></li> <li><a href="/w/index.php?title=Cinalukast&action=edit&redlink=1" class="new" title="Cinalukast (page does not exist)">Cinalukast</a></li> <li><a href="/w/index.php?title=FPL-55712&action=edit&redlink=1" class="new" title="FPL-55712 (page does not exist)">FPL-55712</a></li> <li><a href="/w/index.php?title=ICI-198615&action=edit&redlink=1" class="new" title="ICI-198615 (page does not exist)">ICI-198615</a></li> <li><a href="/w/index.php?title=Iralukast&action=edit&redlink=1" class="new" title="Iralukast (page does not exist)">Iralukast</a></li> <li><a href="/w/index.php?title=LY-170680&action=edit&redlink=1" class="new" title="LY-170680 (page does not exist)">LY-170680</a></li> <li><a href="/w/index.php?title=Masilukast&action=edit&redlink=1" class="new" title="Masilukast (page does not exist)">Masilukast</a></li> <li><a href="/w/index.php?title=MK-571&action=edit&redlink=1" class="new" title="MK-571 (page does not exist)">MK-571</a></li> <li><a href="/wiki/Montelukast" title="Montelukast">Montelukast</a></li> <li><a href="/w/index.php?title=ONO-1078&action=edit&redlink=1" class="new" title="ONO-1078 (page does not exist)">ONO-1078</a></li> <li><a href="/w/index.php?title=Pobilukast&action=edit&redlink=1" class="new" title="Pobilukast (page does not exist)">Pobilukast</a></li> <li><a href="/wiki/Pranlukast" title="Pranlukast">Pranlukast</a></li> <li><a href="/w/index.php?title=Ritolukast&action=edit&redlink=1" class="new" title="Ritolukast (page does not exist)">Ritolukast</a></li> <li><a href="/w/index.php?title=SKF-104353&action=edit&redlink=1" class="new" title="SKF-104353 (page does not exist)">SKF-104353</a></li> <li><a href="/w/index.php?title=SR-2640&action=edit&redlink=1" class="new" title="SR-2640 (page does not exist)">SR-2640</a></li> <li><a href="/w/index.php?title=Sulukast&action=edit&redlink=1" class="new" title="Sulukast (page does not exist)">Sulukast</a></li> <li><a href="/wiki/Tipelukast" title="Tipelukast">Tipelukast</a></li> <li><a href="/w/index.php?title=Tomelukast&action=edit&redlink=1" class="new" title="Tomelukast (page does not exist)">Tomelukast</a></li> <li><a href="/w/index.php?title=Verlukast&action=edit&redlink=1" class="new" title="Verlukast (page does not exist)">Verlukast</a></li> <li><a href="/wiki/Zafirlukast" title="Zafirlukast">Zafirlukast</a></li> <li><a href="/w/index.php?title=ZD-3523&action=edit&redlink=1" class="new" title="ZD-3523 (page does not exist)">ZD-3523</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Cysteinyl_leukotriene_receptor_2" title="Cysteinyl leukotriene receptor 2"><abbr title="Cysteinyl leukotriene receptor 2">CysLT<sub>2</sub></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 Cysteinyl leukotriene receptor 2</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Agonists:</b> <a href="/wiki/Leukotriene_C4" title="Leukotriene C4">Leukotriene C<sub>4</sub></a></li> <li><a href="/wiki/Leukotriene_D4" title="Leukotriene D4">Leukotriene D<sub>4</sub></a></li> <li><a href="/wiki/Leukotriene_E4" title="Leukotriene E4">Leukotriene E<sub>4</sub></a></li></ul> <ul><li><b>Antagonists:</b> <a href="/w/index.php?title=BAYu9773&action=edit&redlink=1" class="new" title="BAYu9773 (page does not exist)">BAYu9773</a></li> <li><a href="/w/index.php?title=BAYu9916&action=edit&redlink=1" class="new" title="BAYu9916 (page does not exist)">BAYu9916</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Cysteinyl_leukotriene_receptor_E" class="mw-redirect" title="Cysteinyl leukotriene receptor E"><abbr title="Cysteinyl leukotriene receptor E">CysLT<sub>E</sub></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 Cysteinyl leukotriene receptor E</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Agonists:</b> <a href="/wiki/Leukotriene_E4" title="Leukotriene E4">Leukotriene E<sub>4</sub></a></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Enzyme" title="Enzyme">Enzyme</a><br /><small>(<a href="/wiki/Enzyme_inhibitor" title="Enzyme inhibitor">inhibitors</a>)</small></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:4em;;text-align:center;"><a href="/wiki/Arachidonate_5-lipoxygenase" title="Arachidonate 5-lipoxygenase"><abbr title="Arachidonate 5-lipoxygenase">5-LOX</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 Arachidonate 5-lipoxygenase</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="/w/index.php?title=2-TEDC&action=edit&redlink=1" class="new" title="2-TEDC (page does not exist)">2-TEDC</a></li> <li><a href="/wiki/Baicalein" title="Baicalein">Baicalein</a></li> <li><a href="/w/index.php?title=BW-A4C&action=edit&redlink=1" class="new" title="BW-A4C (page does not exist)">BW-A4C</a></li> <li><a href="/w/index.php?title=BW-B70C&action=edit&redlink=1" class="new" title="BW-B70C (page does not exist)">BW-B70C</a></li> <li><a href="/wiki/Caffeic_acid" title="Caffeic acid">Caffeic acid</a></li> <li><a href="/w/index.php?title=Cinnamyl-3,4-dihydroxy-%CE%B1-cyanocinnamate&action=edit&redlink=1" class="new" title="Cinnamyl-3,4-dihydroxy-α-cyanocinnamate (page does not exist)">CDC</a></li> <li><a href="/w/index.php?title=CJ-13610&action=edit&redlink=1" class="new" title="CJ-13610 (page does not exist)">CJ-13610</a></li> <li><a href="/wiki/Curcumin" title="Curcumin">Curcumin</a></li> <li><a href="/wiki/Fenleuton" title="Fenleuton">Fenleuton</a></li> <li><a href="/wiki/Hyperforin" title="Hyperforin">Hyperforin</a></li> <li><a href="/wiki/Hypericum_perforatum" title="Hypericum perforatum"><i>Hypericum perforatum</i> (St. John's Wort)</a></li> <li><a href="/wiki/Meclofenamic_acid" title="Meclofenamic acid">Meclofenamic acid (meclofenamate)</a></li> <li><a href="/wiki/Minocycline" title="Minocycline">Minocycline</a></li> <li><a href="/w/index.php?title=N-Stearoyldopamine&action=edit&redlink=1" class="new" title="N-Stearoyldopamine (page does not exist)">N-Stearoyldopamine</a></li> <li><a href="/w/index.php?title=Timegadine&action=edit&redlink=1" class="new" title="Timegadine (page does not exist)">Timegadine</a></li> <li><a href="/wiki/Zileuton" title="Zileuton">Zileuton</a></li></ul> <ul><li><b><a href="/wiki/Arachidonate_5-lipoxygenase-activating_protein" class="mw-redirect" title="Arachidonate 5-lipoxygenase-activating protein"><abbr title="Arachidonate 5-lipoxygenase-activating protein">FLAP</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 Arachidonate 5-lipoxygenase-activating protein</span> inhibitors:</b> <a href="/w/index.php?title=AM-103_(drug)&action=edit&redlink=1" class="new" title="AM-103 (drug) (page does not exist)">AM-103</a></li> <li><a href="/wiki/AM-679_(FLAP_inhibitor)" title="AM-679 (FLAP inhibitor)">AM-679</a></li> <li><a href="/w/index.php?title=BAYx1005&action=edit&redlink=1" class="new" title="BAYx1005 (page does not exist)">BAYx1005</a></li> <li><a href="/w/index.php?title=MK-591&action=edit&redlink=1" class="new" title="MK-591 (page does not exist)">MK-591</a></li> <li><a href="/wiki/MK-886" title="MK-886">MK-886</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Arachidonate_12-lipoxygenase" class="mw-redirect" title="Arachidonate 12-lipoxygenase"><abbr title="Arachidonate 12-lipoxygenase">12-LOX</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 Arachidonate 12-lipoxygenase</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=2-TEDC&action=edit&redlink=1" class="new" title="2-TEDC (page does not exist)">2-TEDC</a></li> <li><a href="/w/index.php?title=3-Methoxytropolone&action=edit&redlink=1" class="new" title="3-Methoxytropolone (page does not exist)">3-Methoxytropolone</a></li> <li><a href="/wiki/Baicalein" title="Baicalein">Baicalein</a></li> <li><a href="/w/index.php?title=Cinnamyl-3,4-dihydroxy-%CE%B1-cyanocinnamate&action=edit&redlink=1" class="new" title="Cinnamyl-3,4-dihydroxy-α-cyanocinnamate (page does not exist)">CDC</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Arachidonate_15-lipoxygenase" class="mw-redirect" title="Arachidonate 15-lipoxygenase"><abbr title="Arachidonate 15-lipoxygenase">15-LOX</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 Arachidonate 15-lipoxygenase</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="/w/index.php?title=2-TEDC&action=edit&redlink=1" class="new" title="2-TEDC (page does not exist)">2-TEDC</a></li> <li><a href="/w/index.php?title=Cinnamyl-3,4-dihydroxy-%CE%B1-cyanocinnamate&action=edit&redlink=1" class="new" title="Cinnamyl-3,4-dihydroxy-α-cyanocinnamate (page does not exist)">CDC</a></li> <li><a href="/wiki/Luteolin" title="Luteolin">Luteolin</a></li> <li><a href="/w/index.php?title=PD-146176&action=edit&redlink=1" class="new" title="PD-146176 (page does not exist)">PD-146176</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Leukotriene_A4_hydrolase" class="mw-redirect" title="Leukotriene A4 hydrolase"><abbr title="Leukotriene A4 hydrolase">LTA<sub>4</sub>H</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 Leukotriene A4 hydrolase</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=Acebilustat&action=edit&redlink=1" class="new" title="Acebilustat (page does not exist)">Acebilustat</a></li> <li><a href="/wiki/Captopril" title="Captopril">Captopril</a></li> <li><a href="/w/index.php?title=DG-051&action=edit&redlink=1" class="new" title="DG-051 (page does not exist)">DG-051</a></li> <li><a href="/wiki/Fosinoprilat" class="mw-redirect" title="Fosinoprilat">Fosinoprilat</a></li> <li><a href="/w/index.php?title=JNJ-26993135&action=edit&redlink=1" class="new" title="JNJ-26993135 (page does not exist)">JNJ-26993135</a></li> <li><a href="/w/index.php?title=SA-6541&action=edit&redlink=1" class="new" title="SA-6541 (page does not exist)">SA-6541</a></li> <li><a href="/w/index.php?title=SC-57461A&action=edit&redlink=1" class="new" title="SC-57461A (page does not exist)">SC-57461A</a></li> <li><a href="/wiki/Ubenimex" title="Ubenimex">Ubenimex (bestatin)</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Leukotriene_B4_%CF%89-hydroxylase" class="mw-redirect" title="Leukotriene B4 ω-hydroxylase"><abbr title="Leukotriene B4 ω-hydroxylase">LTB<sub>4</sub>H</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 Leukotriene B4 ω-hydroxylase</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="/w/index.php?title=17-Octadecynoic_acid&action=edit&redlink=1" class="new" title="17-Octadecynoic acid (page does not exist)">17-Octadecynoic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Leukotriene_C4_synthase" title="Leukotriene C4 synthase"><abbr title="Leukotriene C4 synthase">LTC<sub>4</sub>S</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 Leukotriene C4 synthase</span></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/Azelastine" title="Azelastine">Azelastine</a></li> <li><a href="/wiki/MK-886" title="MK-886">MK-886</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Leukotriene_C4_hydrolase" title="Leukotriene C4 hydrolase"><abbr title="Leukotriene C4 hydrolase">LTC<sub>4</sub>H</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 Leukotriene C4 hydrolase</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/Acivicin" title="Acivicin">Acivicin</a></li> <li><a href="/w/index.php?title=Serine-borate_complex&action=edit&redlink=1" class="new" title="Serine-borate complex (page does not exist)">Serine-borate complex</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Leukotriene_D4_hydrolase" class="mw-redirect" title="Leukotriene D4 hydrolase"><abbr title="Leukotriene D4 hydrolase">LTD<sub>4</sub></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 Leukotriene D4 hydrolase</span></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/Cilastatin" title="Cilastatin">Cilastatin</a></li> <li><a href="/wiki/Ubenimex" title="Ubenimex">Ubenimex (bestatin)</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;">Others</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><b>Precursors:</b> <a class="mw-selflink selflink">Linoleic acid</a></li> <li><a href="/wiki/Gamma-Linolenic_acid" class="mw-redirect" title="Gamma-Linolenic acid">γ-Linolenic acid (gamolenic acid)</a></li> <li><a href="/wiki/Dihomo-%CE%B3-linolenic_acid" title="Dihomo-γ-linolenic acid">Dihomo-γ-linolenic acid</a></li> <li><a href="/wiki/Diglyceride" title="Diglyceride">Diacylglycerol</a></li> <li><a href="/wiki/Arachidonic_acid" title="Arachidonic acid">Arachidonic acid</a></li> <li><a href="/wiki/Arachidonic_acid_5-hydroperoxide" title="Arachidonic acid 5-hydroperoxide">5-HPETE (arachidonic acid 5-hydroperoxide)</a></li> <li><a href="/wiki/Leukotriene_A4" title="Leukotriene A4">Leukotriene A<sub>4</sub></a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt>See also</dt> <dd><i><a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></i></dd> <dd><i><a href="/wiki/Template:Prostanoid_signaling_modulators" title="Template:Prostanoid signaling modulators">Prostanoid signaling modulators</a></i></dd></dl> </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"><style data-mw-deduplicate="TemplateStyles:r1038841319">.mw-parser-output .tooltip-dotted{border-bottom:1px dotted;cursor:help}</style><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1038841319"></div><div role="navigation" class="navbox authority-control" aria-label="Navbox" style="padding:3px"><table class="nowraplinks hlist navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Help:Authority_control" title="Help:Authority control">Authority control databases</a>: National <span 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