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class="vector-toc-numb">2.2</span> <span>Mammals</span> </div> </a> <ul id="toc-Mammals-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Anaerobic_pathway" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Anaerobic_pathway"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.3</span> <span>Anaerobic pathway</span> </div> </a> <ul id="toc-Anaerobic_pathway-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Metabolism" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Metabolism"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Metabolism</span> </div> </a> <ul id="toc-Metabolism-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Potential_health_effects" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Potential_health_effects"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Potential health effects</span> </div> </a> <button aria-controls="toc-Potential_health_effects-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 Potential health effects subsection</span> </button> <ul id="toc-Potential_health_effects-sublist" class="vector-toc-list"> <li id="toc-Cardiovascular" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Cardiovascular"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.1</span> <span>Cardiovascular</span> </div> </a> <ul id="toc-Cardiovascular-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Pregnancy_and_lactation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Pregnancy_and_lactation"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.2</span> <span>Pregnancy and lactation</span> </div> </a> <ul id="toc-Pregnancy_and_lactation-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Brain_and_visual_functions" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Brain_and_visual_functions"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.3</span> <span>Brain and visual functions</span> </div> </a> <ul id="toc-Brain_and_visual_functions-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Asthma" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Asthma"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.4</span> <span>Asthma</span> </div> </a> <ul id="toc-Asthma-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Nutrition" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Nutrition"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Nutrition</span> </div> </a> <button aria-controls="toc-Nutrition-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 Nutrition subsection</span> </button> <ul id="toc-Nutrition-sublist" class="vector-toc-list"> <li id="toc-Discovery_of_algae-based_DHA" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Discovery_of_algae-based_DHA"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1</span> <span>Discovery of algae-based DHA</span> </div> </a> <ul id="toc-Discovery_of_algae-based_DHA-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Use_as_a_food_additive" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Use_as_a_food_additive"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.2</span> <span>Use as a food additive</span> </div> </a> <ul id="toc-Use_as_a_food_additive-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Studies_of_vegetarians_and_vegans" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Studies_of_vegetarians_and_vegans"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.3</span> <span>Studies of vegetarians and vegans</span> </div> </a> <ul id="toc-Studies_of_vegetarians_and_vegans-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-DHA_and_EPA_in_fish_oils" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#DHA_and_EPA_in_fish_oils"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.4</span> <span>DHA and EPA in fish oils</span> </div> </a> <ul id="toc-DHA_and_EPA_in_fish_oils-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Recommended_daily_DHA_intake_for_children" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Recommended_daily_DHA_intake_for_children"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.5</span> <span>Recommended daily DHA intake for children</span> </div> </a> <ul id="toc-Recommended_daily_DHA_intake_for_children-sublist" class="vector-toc-list"> </ul> </li> </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> </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" title="Table of Contents" > <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">Docosahexaenoic 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 32 languages" > <label id="p-lang-btn-label" for="p-lang-btn-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--action-progressive mw-portlet-lang-heading-32" aria-hidden="true" ><span class="vector-icon mw-ui-icon-language-progressive mw-ui-icon-wikimedia-language-progressive"></span> <span class="vector-dropdown-label-text">32 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%AD%D9%85%D8%B6_%D8%A7%D9%84%D8%AF%D9%88%D9%83%D9%88%D8%B3%D8%A7%D9%87%D9%83%D8%B3%D8%A7%D9%8A%D9%86%D9%88%D9%8A%D9%83" title="حمض الدوكوساهكساينويك – Arabic" lang="ar" hreflang="ar" data-title="حمض الدوكوساهكساينويك" 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%AF%D9%88%DA%A9%D9%88%D8%B2%D8%A7%D9%87%D9%82%D8%B2%D8%A7%D9%86%D9%88%D8%A6%DB%8C%DA%A9_%D8%A7%D8%B3%DB%8C%D8%AF" title="دوکوزاهقزانوئیک اسید – South Azerbaijani" lang="azb" hreflang="azb" data-title="دوکوزاهقزانوئیک اسید" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%94%D0%BE%D0%BA%D0%BE%D0%B7%D0%B0%D1%85%D0%B5%D0%BA%D1%81%D0%B0%D0%B5%D0%BD%D0%BE%D0%B2%D0%B0_%D0%BA%D0%B8%D1%81%D0%B5%D0%BB%D0%B8%D0%BD%D0%B0" title="Докозахексаенова киселина – Bulgarian" lang="bg" hreflang="bg" data-title="Докозахексаенова киселина" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target"><span>Български</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/%C3%80cid_docosahexaenoic" title="Àcid docosahexaenoic – Catalan" lang="ca" hreflang="ca" data-title="Àcid docosahexaenoic" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Docosahexaensyre" title="Docosahexaensyre – Danish" lang="da" hreflang="da" data-title="Docosahexaensyre" 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/Docosahexaens%C3%A4ure" title="Docosahexaensäure – German" lang="de" hreflang="de" data-title="Docosahexaensäure" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/%C3%81cido_docosahexaenoico" title="Ácido docosahexaenoico – Spanish" lang="es" hreflang="es" data-title="Ácido docosahexaenoico" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%AF%D9%88%DA%A9%D9%88%D8%B2%D8%A7%D9%87%DA%AF%D8%B2%D8%A7%D9%86%D9%88%D8%A6%DB%8C%DA%A9_%D8%A7%D8%B3%DB%8C%D8%AF" title="دوکوزاهگزانوئیک اسید – Persian" lang="fa" hreflang="fa" data-title="دوکوزاهگزانوئیک اسید" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Acide_docosahexa%C3%A9no%C3%AFque" title="Acide docosahexaénoïque – French" lang="fr" hreflang="fr" data-title="Acide docosahexaénoïque" 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_docosahexaenoico" title="Ácido docosahexaenoico – Galician" lang="gl" hreflang="gl" data-title="Ácido docosahexaenoico" 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%8F%84%EC%BD%94%EC%82%AC%ED%97%A5%EC%82%AC%EC%97%94%EC%82%B0" title="도코사헥사엔산 – Korean" lang="ko" hreflang="ko" data-title="도코사헥사엔산" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Dokosaheksaenoi%C4%8Dna_kiselina" title="Dokosaheksaenoična kiselina – Croatian" lang="hr" hreflang="hr" data-title="Dokosaheksaenoična kiselina" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Asam_dokosaheksaenoat" title="Asam dokosaheksaenoat – Indonesian" lang="id" hreflang="id" data-title="Asam dokosaheksaenoat" 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_docosaesaenoico" title="Acido docosaesaenoico – Italian" lang="it" hreflang="it" data-title="Acido docosaesaenoico" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Cervonsk%C4%81be" title="Cervonskābe – Latvian" lang="lv" hreflang="lv" data-title="Cervonskābe" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target"><span>Latviešu</span></a></li><li class="interlanguage-link interwiki-lt mw-list-item"><a href="https://lt.wikipedia.org/wiki/Dokozaheksaeno_r%C5%ABg%C5%A1tis" title="Dokozaheksaeno rūgštis – Lithuanian" lang="lt" hreflang="lt" data-title="Dokozaheksaeno rūgštis" data-language-autonym="Lietuvių" data-language-local-name="Lithuanian" class="interlanguage-link-target"><span>Lietuvių</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%94%D0%BE%D0%BA%D0%BE%D0%B7%D0%B0%D1%85%D0%B5%D0%BA%D1%81%D0%B0%D0%B5%D0%BD%D0%BE%D0%B8%D0%BD%D1%81%D0%BA%D0%B0_%D0%BA%D0%B8%D1%81%D0%B5%D0%BB%D0%B8%D0%BD%D0%B0" title="Докозахексаеноинска киселина – Macedonian" lang="mk" hreflang="mk" data-title="Докозахексаеноинска киселина" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Docosahexaeenzuur" title="Docosahexaeenzuur – Dutch" lang="nl" hreflang="nl" data-title="Docosahexaeenzuur" 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%89%E3%82%B3%E3%82%B5%E3%83%98%E3%82%AD%E3%82%B5%E3%82%A8%E3%83%B3%E9%85%B8" title="ドコサヘキサエン酸 – Japanese" lang="ja" hreflang="ja" data-title="ドコサヘキサエン酸" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Kwas_dokozaheksaenowy" title="Kwas dokozaheksaenowy – Polish" lang="pl" hreflang="pl" data-title="Kwas dokozaheksaenowy" 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_docosa-hexaenoico" title="Ácido docosa-hexaenoico – Portuguese" lang="pt" hreflang="pt" data-title="Ácido docosa-hexaenoico" 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_docosahexaenoic" title="Acid docosahexaenoic – Romanian" lang="ro" hreflang="ro" data-title="Acid docosahexaenoic" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%94%D0%BE%D0%BA%D0%BE%D0%B7%D0%B0%D0%B3%D0%B5%D0%BA%D1%81%D0%B0%D0%B5%D0%BD%D0%BE%D0%B2%D0%B0%D1%8F_%D0%BA%D0%B8%D1%81%D0%BB%D0%BE%D1%82%D0%B0" title="Докозагексаеновая кислота – Russian" lang="ru" hreflang="ru" data-title="Докозагексаеновая кислота" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Dokozaheksaenoinska_kiselina" title="Dokozaheksaenoinska kiselina – Serbian" lang="sr" hreflang="sr" data-title="Dokozaheksaenoinska 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/Dokozaheksaenoinska_kiselina" title="Dokozaheksaenoinska kiselina – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Dokozaheksaenoinska 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-su mw-list-item"><a href="https://su.wikipedia.org/wiki/Asam_dokosah%C3%A9ksa%C3%A9noat" title="Asam dokosahéksaénoat – Sundanese" lang="su" hreflang="su" data-title="Asam dokosahéksaénoat" data-language-autonym="Sunda" data-language-local-name="Sundanese" class="interlanguage-link-target"><span>Sunda</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Dokosaheksaeenihappo" title="Dokosaheksaeenihappo – Finnish" lang="fi" hreflang="fi" data-title="Dokosaheksaeenihappo" 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/Dokosahexaensyra" title="Dokosahexaensyra – Swedish" lang="sv" hreflang="sv" data-title="Dokosahexaensyra" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%94%D0%BE%D0%BA%D0%BE%D0%B7%D0%B0%D0%B3%D0%B5%D0%BA%D1%81%D0%B0%D1%94%D0%BD%D0%BE%D0%B2%D0%B0_%D0%BA%D0%B8%D1%81%D0%BB%D0%BE%D1%82%D0%B0" title="Докозагексаєнова кислота – Ukrainian" lang="uk" hreflang="uk" data-title="Докозагексаєнова 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_docosahexaenoic" title="Acid docosahexaenoic – Vietnamese" lang="vi" hreflang="vi" data-title="Acid docosahexaenoic" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target"><span>Tiếng Việt</span></a></li><li class="interlanguage-link interwiki-wuu mw-list-item"><a href="https://wuu.wikipedia.org/wiki/%E4%BA%8C%E5%8D%81%E4%BA%8C%E7%A2%B3%E5%85%AD%E7%83%AF%E9%85%B8" title="二十二碳六烯酸 – Wu" lang="wuu" hreflang="wuu" data-title="二十二碳六烯酸" data-language-autonym="吴语" data-language-local-name="Wu" class="interlanguage-link-target"><span>吴语</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a 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omega−3 fatty acid. For the vitamin C metabolite also abbreviated as DHA, see <a href="/wiki/Dehydroascorbic_acid" title="Dehydroascorbic acid">Dehydroascorbic acid</a>.</div> <style data-mw-deduplicate="TemplateStyles:r1268415487">.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%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}</style> <table class="infobox ib-chembox"> <caption>Docosahexaenoic acid </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:DHA_numbers.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/ed/DHA_numbers.svg/300px-DHA_numbers.svg.png" decoding="async" width="300" height="99" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/ed/DHA_numbers.svg/450px-DHA_numbers.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/ed/DHA_numbers.svg/600px-DHA_numbers.svg.png 2x" data-file-width="356" data-file-height="117" /></a><figcaption></figcaption></figure> </td></tr> <tr> <td colspan="2" class="borderless" style="text-align:center"> <table border="0" style="width:100%;display:inline-table;"> <tbody><tr> <td style="border-right:1px solid #aaa; width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Docosahexaenoic-acid-3D-balls.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/73/Docosahexaenoic-acid-3D-balls.png/170px-Docosahexaenoic-acid-3D-balls.png" decoding="async" width="170" height="172" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/73/Docosahexaenoic-acid-3D-balls.png/255px-Docosahexaenoic-acid-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/73/Docosahexaenoic-acid-3D-balls.png/340px-Docosahexaenoic-acid-3D-balls.png 2x" data-file-width="1977" data-file-height="2000" /></a><figcaption></figcaption></figure> </td> <td style="width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Docosahexaenoic-acid-3D-sf.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/bf/Docosahexaenoic-acid-3D-sf.png/170px-Docosahexaenoic-acid-3D-sf.png" decoding="async" width="170" height="179" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/bf/Docosahexaenoic-acid-3D-sf.png/255px-Docosahexaenoic-acid-3D-sf.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/bf/Docosahexaenoic-acid-3D-sf.png/340px-Docosahexaenoic-acid-3D-sf.png 2x" data-file-width="1901" data-file-height="2000" /></a><figcaption></figcaption></figure> </td></tr></tbody></table> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; 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;">(4<i>Z</i>,7<i>Z</i>,10<i>Z</i>,13<i>Z</i>,16<i>Z</i>,19<i>Z</i>)-Docosa-4,7,10,13,16,19-hexaenoic 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;">cervonic acid<br />DHA<br />doconexent (<a href="/wiki/International_nonproprietary_name" title="International nonproprietary name">INN</a>)</div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; 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=6217-54-5">6217-54-5</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=O%3DC%28O%29CC%5CC%3DC%2FC%2FC%3DC%5CC%5CC%3DC%2FC%5CC%3DC%2FC%5CC%3DC%2FC%5CC%3DC%2FCC">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td>Abbreviations </td> <td>DHA </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>1715505 </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=28125">CHEBI:28125</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" 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//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.393183.html">393183</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/DB03756">DB03756</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/100.118.398">100.118.398</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q423345#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>612-950-9</li></ul></div> </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=1051">1051</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/C06429">C06429</a></span></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/445580">445580</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/ZAD9OKH9JC">ZAD9OKH9JC</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/DTXSID5040465">DTXSID5040465</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q423345#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;"><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/C22H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h3-4,6-7,9-10,12-13,15-16,18-19H,2,5,8,11,14,17,20-21H2,1H3,(H,23,24)/b4-3-,7-6-,10-9-,13-12-,16-15-,19-18-<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: MBMBGCFOFBJSGT-KUBAVDMBSA-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/C22H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h3-4,6-7,9-10,12-13,15-16,18-19H,2,5,8,11,14,17,20-21H2,1H3,(H,23,24)/b4-3-,7-6-,10-9-,13-12-,16-15-,19-18-</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: MBMBGCFOFBJSGT-KUBAVDMBBZ</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;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">O=C(O)CC\C=C/C/C=C\C\C=C/C\C=C/C\C=C/C\C=C/CC</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; 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>C<sub>22</sub>H<sub>32</sub>O<sub>2</sub>  </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td>328.488 g/mol    </td></tr> <tr> <td><a href="/wiki/Density" title="Density">Density</a> </td> <td>0.943 g/cm<sup>3</sup> </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>−44 °C (−47 °F; 229 K) </td></tr> <tr> <td><a href="/wiki/Boiling_point" title="Boiling point">Boiling point</a> </td> <td>446.7 °C (836.1 °F; 719.8 K) </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; color:inherit; 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=477163061&page2=Docosahexaenoic+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>Docosahexaenoic acid</b> (<b>DHA</b>) is an <a href="/wiki/Omega-3_fatty_acid" title="Omega-3 fatty acid">omega−3 fatty acid</a> that is an important component of the human <a href="/wiki/Brain" title="Brain">brain</a>, <a href="/wiki/Cerebral_cortex" title="Cerebral cortex">cerebral cortex</a>, <a href="/wiki/Skin" title="Skin">skin</a>, and <a href="/wiki/Retina" title="Retina">retina</a>. It is given the <a href="/wiki/Nomenclature_of_fatty_acids" class="mw-redirect" title="Nomenclature of fatty acids">fatty acid notation</a> <b>22:6(<i>n</i>−3)</b>.<sup id="cite_ref-ods_1-0" class="reference"><a href="#cite_note-ods-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> It can be synthesized from <a href="/wiki/%CE%91-Linolenic_acid" title="Α-Linolenic acid">alpha-linolenic acid</a> or obtained directly from maternal milk (breast milk), fatty fish, fish oil, or algae oil.<sup id="cite_ref-ods_1-1" class="reference"><a href="#cite_note-ods-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> The consumption of DHA (e.g., from fatty fish such as salmon, herring, mackerel and sardines) contributes to numerous physiological benefits, including cognition.<sup id="cite_ref-calder_3-0" class="reference"><a href="#cite_note-calder-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> As a component of <a href="/wiki/Neuronal_membrane" class="mw-redirect" title="Neuronal membrane">neuronal membranes</a>, the function of DHA is to support neuronal conduction and to allow the optimal functioning of neuronal membrane proteins (such as receptors and enzymes).<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>Structurally, DHA is a <a href="/wiki/Carboxylic_acid" title="Carboxylic acid">carboxylic acid</a> (-<i>oic acid</i>) with a 22-<a href="/wiki/Carbon_chain" class="mw-redirect" title="Carbon chain">carbon chain</a> (<i>docosa-</i> derives from the <a href="/wiki/Ancient_Greek" title="Ancient Greek">Ancient Greek</a> for 22) and six (<i>hexa-</i>) <i><a href="/wiki/Cis-trans_isomerism" class="mw-redirect" title="Cis-trans isomerism">cis</a></i> <a href="/wiki/Double_bond" title="Double bond">double bonds</a> (<i>-en-</i>);<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> with the first double bond located at the third carbon from the omega end.<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> Its <a href="/wiki/Trivial_name" title="Trivial name">trivial name</a> is <i>cervonic acid</i> (from the <a href="/wiki/Latin" title="Latin">Latin</a> word <i>cerebrum</i> for "brain"), its <a href="/wiki/Systematic_name" title="Systematic name">systematic name</a> is <i>all-cis-docosa-4,7,10,13,16,19-hexa-enoic acid</i>. </p><p>In organisms that do not eat <a href="/wiki/Algae" title="Algae">algae</a> containing DHA nor animal products containing DHA, DHA is instead produced internally from <a href="/wiki/%CE%91-Linolenic_acid" title="Α-Linolenic acid">α-linolenic acid</a>, a shorter omega−3 fatty acid manufactured by plants (and also occurring in animal products as obtained from plants).<sup id="cite_ref-Burdge_8-0" class="reference"><a href="#cite_note-Burdge-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> Limited amounts of <a href="/wiki/Eicosapentaenoic_acid" title="Eicosapentaenoic acid">eicosapentaenoic</a> and <a href="/wiki/Docosapentaenoic_acid" title="Docosapentaenoic acid">docosapentaenoic acids</a> are possible products of α-linolenic acid metabolism in young women<sup id="cite_ref-Burdge1_9-0" class="reference"><a href="#cite_note-Burdge1-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> and men.<sup id="cite_ref-Burdge_8-1" class="reference"><a href="#cite_note-Burdge-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> DHA in <a href="/wiki/Breast_milk" title="Breast milk">breast milk</a> is important for the developing infant.<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> Rates of DHA production in women are 15% higher than in men.<sup id="cite_ref-ajcn.org_11-0" class="reference"><a href="#cite_note-ajcn.org-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p><p>DHA is a major fatty acid in brain <a href="/wiki/Phospholipid" title="Phospholipid">phospholipids</a> and the <a href="/wiki/Retina" title="Retina">retina</a>. Preliminary research has investigated its potential benefit in <a href="/wiki/Alzheimer%27s_disease" title="Alzheimer's disease">Alzheimer's disease</a>,<sup id="cite_ref-ods_1-2" class="reference"><a href="#cite_note-ods-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-canhada_12-0" class="reference"><a href="#cite_note-canhada-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> and <a href="/wiki/Cardiovascular_disease" title="Cardiovascular disease">cardiovascular disease</a>,<sup id="cite_ref-Innes20_13-0" class="reference"><a href="#cite_note-Innes20-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> and other disorders.<sup id="cite_ref-ods_1-3" class="reference"><a href="#cite_note-ods-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Central_nervous_system_constituent">Central nervous system constituent</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Docosahexaenoic_acid&action=edit&section=1" title="Edit section: Central nervous system constituent"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>DHA is the most abundant omega−3 fatty acid in the brain and retina.<sup id="cite_ref-Kim_14-0" class="reference"><a href="#cite_note-Kim-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> DHA comprises 40% of the <a href="/wiki/Polyunsaturated_fatty_acid" class="mw-redirect" title="Polyunsaturated fatty acid">polyunsaturated fatty acids</a> (PUFAs) in the brain and 60% of the PUFAs in the retina. Fifty percent of a <a href="/wiki/Neuron" title="Neuron">neuronal</a> <a href="/wiki/Plasma_membrane" class="mw-redirect" title="Plasma membrane">plasma membrane</a> is composed of DHA.<sup id="cite_ref-Singh_15-0" class="reference"><a href="#cite_note-Singh-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> DHA modulates the carrier-mediated transport of choline, glycine, and taurine, the function of delayed rectifier <a href="/wiki/Potassium_channel" title="Potassium channel">potassium channels</a>, and the response of <a href="/wiki/Rhodopsin" title="Rhodopsin">rhodopsin</a> contained in the <a href="/wiki/Synaptic_vesicle" title="Synaptic vesicle">synaptic vesicles</a>.<sup id="cite_ref-Spector15_16-0" class="reference"><a href="#cite_note-Spector15-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Spector_17-0" class="reference"><a href="#cite_note-Spector-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </p><p><a href="/wiki/Phosphatidylserine" title="Phosphatidylserine">Phosphatidylserine</a> (PS) – which contains high DHA content – has roles in <a href="/wiki/Axon#Extracellular_signaling" title="Axon">neuronal signaling</a> and <a href="/wiki/Neurotransmitter" title="Neurotransmitter">neurotransmitter</a> synthesis,<sup id="cite_ref-Kim_14-1" class="reference"><a href="#cite_note-Kim-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> and DHA deficiency is associated with cognitive decline.<sup id="cite_ref-Kim_14-2" class="reference"><a href="#cite_note-Kim-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Lukiw_18-0" class="reference"><a href="#cite_note-Lukiw-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> DHA levels are reduced in the brain tissue of severely depressed people.<sup id="cite_ref-pmid17188654_19-0" class="reference"><a href="#cite_note-pmid17188654-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup><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> </p> <div class="mw-heading mw-heading2"><h2 id="Biosynthesis">Biosynthesis</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Docosahexaenoic_acid&action=edit&section=2" title="Edit section: Biosynthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Aerobic_eukaryote_pathway">Aerobic eukaryote pathway</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Docosahexaenoic_acid&action=edit&section=3" title="Edit section: Aerobic eukaryote pathway"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Aerobic eukaryotes, specifically microalgae, <a href="/wiki/Moss" title="Moss">mosses</a>, <a href="/wiki/Fungus" title="Fungus">fungi</a>, and some animals, perform biosynthesis of DHA as a series of desaturation and elongation reactions, catalyzed by the sequential action of desaturase and elongase <a href="/wiki/Enzyme" title="Enzyme">enzymes</a>. This pathway, originally identified in <i>Thraustochytrium</i>, applies to these groups:<sup id="cite_ref-Qiu_21-0" class="reference"><a href="#cite_note-Qiu-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> </p> <ol><li>a desaturation at the sixth carbon of <a href="/wiki/%CE%91-Linolenic_acid" title="Α-Linolenic acid">alpha-linolenic acid</a> by a delta 6 desaturase to produce <a href="/wiki/Stearidonic_acid" title="Stearidonic acid">stearidonic acid</a> (SDA, 18:4 ω-3),</li> <li>elongation of the <a href="/wiki/Stearidonic_acid" title="Stearidonic acid">stearidonic acid</a> by a delta 6 elongase to produce <a href="/wiki/Eicosatetraenoic_acid" title="Eicosatetraenoic acid">eicosatetraenoic acid</a> (ETA, 20:4 ω-3),</li> <li>desaturation at the fifth carbon of <a href="/wiki/Eicosatetraenoic_acid" title="Eicosatetraenoic acid">eicosatetraenoic acid</a> by a delta 5 desaturase to produce <a href="/wiki/Eicosapentaenoic_acid" title="Eicosapentaenoic acid">eicosapentaenoic acid</a> (EPA, 20:5 ω-3),</li> <li>elongation of <a href="/wiki/Eicosapentaenoic_acid" title="Eicosapentaenoic acid">eicosapentaenoic acid</a> by a delta 5 elongase to produce <a href="/wiki/Docosapentaenoic_acid" title="Docosapentaenoic acid">docosapentaenoic acid</a> (DPA, 22:5 ω-3), and</li> <li>desaturation at the fourth carbon of <a href="/wiki/Docosapentaenoic_acid" title="Docosapentaenoic acid">docosapentaenoic acid</a> by a delta 4 desaturase to produce DHA.</li></ol> <div class="mw-heading mw-heading3"><h3 id="Mammals">Mammals</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Docosahexaenoic_acid&action=edit&section=4" title="Edit section: Mammals"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In humans, DHA is either obtained from the diet or may be converted in small amounts from <a href="/wiki/Eicosapentaenoic_acid" title="Eicosapentaenoic acid">eicosapentaenoic acid</a> (EPA, 20:5, ω-3). With the identification of <a href="/wiki/FADS2" title="FADS2">FADS2</a> as a human Δ4-desaturase in 2015, it is now known that humans follow the same synthesis pathway as aerobic eukaryotes, involving Δ5-elongation to DPA and Δ4-desaturation to DHA.<sup id="cite_ref-pmid26065859_22-0" class="reference"><a href="#cite_note-pmid26065859-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> </p><p>A "Sprecher's shunt" hypothesis, proposed in 1991, postulates that EPA is twice elongated to 24:5 ω-3, then desaturated to 24:6 ω-3 (via <a href="/wiki/Delta_6_desaturase" class="mw-redirect" title="Delta 6 desaturase">delta 6 desaturase</a>) in the mitochondria, then shortened to DHA (22:6 ω-3) via <a href="/wiki/Beta_oxidation" title="Beta oxidation">beta oxidation</a> in the <a href="/wiki/Peroxisome" title="Peroxisome">peroxisome</a>. The hypothesis was accepted in the absence of an identified Δ4-desaturase in mammals prior to 2015.<sup id="cite_ref-DeCaterina_23-0" class="reference"><a href="#cite_note-DeCaterina-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Voss_24-0" class="reference"><a href="#cite_note-Voss-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> The shunt model does not match clinical data, specifically that patients with beta oxidation defects do not display issues in DHA synthesis. With the identification of a Δ4-desaturase, it is considered outdated.<sup id="cite_ref-pmid26065859_22-1" class="reference"><a href="#cite_note-pmid26065859-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Anaerobic_pathway">Anaerobic pathway</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Docosahexaenoic_acid&action=edit&section=5" title="Edit section: Anaerobic pathway"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Marine bacteria and the microalgae <i><a href="/wiki/Schizochytrium" title="Schizochytrium">Schizochytrium</a></i> use an anerobic <a href="/wiki/Polyketide_synthase" title="Polyketide synthase">polyketide synthase</a> pathway to synthesize DHA.<sup id="cite_ref-Qiu_21-1" class="reference"><a href="#cite_note-Qiu-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Metabolism">Metabolism</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Docosahexaenoic_acid&action=edit&section=6" title="Edit section: Metabolism"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>DHA can be metabolized into DHA-derived <a href="/wiki/Specialized_pro-resolving_mediators" title="Specialized pro-resolving mediators">specialized pro-resolving mediators</a> (SPMs), DHA epoxides, electrophilic oxo-derivatives (EFOX) of DHA, neuroprostanes, ethanolamines, acylglycerols, docosahexaenoyl amides of amino acids or neurotransmitters, and branched DHA esters of hydroxy fatty acids, among others.<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> </p><p>The enzyme <a href="/wiki/CYP2C9" title="CYP2C9">CYP2C9</a> metabolizes DHA to <a href="/wiki/Epoxydocosapentaenoic_acid" title="Epoxydocosapentaenoic acid">epoxydocosapentaenoic acids</a> (EDPs; primarily 19,20-epoxy-eicosapentaenoic acid isomers [i.e. 10,11-EDPs]).<sup id="cite_ref-Westphal2011_26-0" class="reference"><a href="#cite_note-Westphal2011-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Potential_health_effects">Potential health effects</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Docosahexaenoic_acid&action=edit&section=7" title="Edit section: Potential health effects"><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/Omega-3_fatty_acid#Health_effects" title="Omega-3 fatty acid">Omega-3 fatty acid § Health effects</a></div> <div class="mw-heading mw-heading3"><h3 id="Cardiovascular">Cardiovascular</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Docosahexaenoic_acid&action=edit&section=8" title="Edit section: Cardiovascular"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Though mixed and plagued by methodological inconsistencies, there is now convincing evidence from ecological, RCTs, meta-analyses and animal trials that shows a benefit for omega−3 dietary intake for cardiovascular health.<sup id="cite_ref-ods_1-4" class="reference"><a href="#cite_note-ods-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Innes20_13-1" class="reference"><a href="#cite_note-Innes20-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> Of the <i>n</i>−3 FAs, DHA has been argued to be the most beneficial due to its preferential uptake in the myocardium, its strongly anti-inflammatory activity and its metabolism toward neuroprotectins and resolvins, the latter of which directly contribute to cardiac function.<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> </p><p>DHA is associated with its role in cardiovascular protection and lowering the risk of coronary artery disease. DHA supplementation has been shown to improve high-density lipoprotein (‘good cholesterol’), and lower total cholesterol as well as blood pressure levels.<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> <div class="mw-heading mw-heading3"><h3 id="Pregnancy_and_lactation">Pregnancy and lactation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Docosahexaenoic_acid&action=edit&section=9" title="Edit section: Pregnancy and lactation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Foods high in omega−3 fatty acids may be recommended to women who want to become pregnant or when nursing.<sup id="cite_ref-29" class="reference"><a href="#cite_note-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> A working group from the International Society for the Study of Fatty Acids and Lipids recommended 300 mg/day of DHA for pregnant and lactating women, whereas the average consumption was between 45 mg and 115 mg per day of the women in the study, similar to a Canadian study.<sup id="cite_ref-denomme_30-0" class="reference"><a href="#cite_note-denomme-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Brain_and_visual_functions">Brain and visual functions</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Docosahexaenoic_acid&action=edit&section=10" title="Edit section: Brain and visual functions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>A major structural component of the mammalian central nervous system, DHA is the most abundant omega−3 fatty acid in the brain and retina.<sup id="cite_ref-31" class="reference"><a href="#cite_note-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> Brain and retinal function rely on dietary intake of DHA to support a broad range of <a href="/wiki/Cell_membrane" title="Cell membrane">cell membrane</a> and <a href="/wiki/Cell_signaling" title="Cell signaling">cell signaling</a> properties, particularly in <a href="/wiki/Grey_matter" title="Grey matter">grey matter</a> and retinal <a href="/wiki/Photoreceptor_cell" title="Photoreceptor cell">photoreceptor cell</a> outer segments, which are rich in membranes.<sup id="cite_ref-32" class="reference"><a href="#cite_note-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup><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> </p><p>A <a href="/wiki/Systematic_review" title="Systematic review">systematic review</a> found that DHA had no significant benefits in improving visual field in individuals with <a href="/wiki/Retinitis_pigmentosa" title="Retinitis pigmentosa">retinitis pigmentosa</a>.<sup id="cite_ref-34" class="reference"><a href="#cite_note-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> Animal research shows effect of oral intake of <a href="/wiki/Reinforced_lipids" title="Reinforced lipids">deuterium-reinforced</a> DHA (D-DHA) for prevention of <a href="/wiki/Macular_degeneration" title="Macular degeneration">macular degeneration</a>.<sup id="cite_ref-35" class="reference"><a href="#cite_note-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Asthma">Asthma</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Docosahexaenoic_acid&action=edit&section=11" title="Edit section: Asthma"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Omega−3 PUFAs such as DHA and eicosapentaenoic acid (EPA) are effective in the prevention and treatment of asthma and allergic diseases.<sup id="cite_ref-36" class="reference"><a href="#cite_note-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Nutrition">Nutrition</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Docosahexaenoic_acid&action=edit&section=12" title="Edit section: Nutrition"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:DHA_pills.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/61/DHA_pills.jpg/220px-DHA_pills.jpg" decoding="async" width="220" height="165" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/61/DHA_pills.jpg/330px-DHA_pills.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/61/DHA_pills.jpg/440px-DHA_pills.jpg 2x" data-file-width="2592" data-file-height="1944" /></a><figcaption>Algae-based DHA supplements</figcaption></figure> <p>Ordinary types of cooked <a href="/wiki/Salmon" title="Salmon">salmon</a> contain 500–1500 mg DHA and 300–1000 mg EPA per 100 grams.<sup id="cite_ref-usda2005_37-0" class="reference"><a href="#cite_note-usda2005-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup> Additional rich seafood sources of DHA include <a href="/wiki/Caviar" title="Caviar">caviar</a> (3400 mg per 100 grams), <a href="/wiki/Anchovy" title="Anchovy">anchovies</a> (1292 mg per 100 grams), <a href="/wiki/Mackerel" title="Mackerel">mackerel</a> (1195 mg per 100 grams), and cooked <a href="/wiki/Herring" title="Herring">herring</a> (1105 mg per 100 grams).<sup id="cite_ref-usda2005_37-1" class="reference"><a href="#cite_note-usda2005-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup> </p><p><a href="/wiki/Brain_as_food" title="Brain as food">Brains from mammals taken as food</a> are also a good direct source. Beef brain, for example, contains approximately 855 mg of DHA per 100 grams in a serving.<sup id="cite_ref-38" class="reference"><a href="#cite_note-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup> While DHA may be the primary fatty acid found in certain specialized tissues, these tissues, aside from the brain, are typically small in size, such as the seminiferous tubules and the retina. As a result, animal-based foods, excluding the brain, generally offer minimal amounts of preformed DHA.<sup id="cite_ref-doi.org_39-0" class="reference"><a href="#cite_note-doi.org-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Discovery_of_algae-based_DHA">Discovery of algae-based DHA</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Docosahexaenoic_acid&action=edit&section=13" title="Edit section: Discovery of algae-based DHA"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In the early 1980s, <a href="/wiki/NASA" title="NASA">NASA</a> sponsored scientific research on a plant-based food source that could generate oxygen and nutrition on long-duration <a href="/wiki/Space_flight" class="mw-redirect" title="Space flight">space flights</a>. Certain species of marine <a href="/wiki/Algae" title="Algae">algae</a> produced rich nutrients, leading to the development of an algae-based, vegetable-like oil that contains two polyunsaturated fatty acids, DHA and <a href="/wiki/Arachidonic_acid" title="Arachidonic acid">arachidonic acid</a>.<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> </p> <div class="mw-heading mw-heading3"><h3 id="Use_as_a_food_additive">Use as a food additive</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Docosahexaenoic_acid&action=edit&section=14" title="Edit section: Use as a food additive"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>DHA is widely used as a <a href="/wiki/Food_supplement" class="mw-redirect" title="Food supplement">food supplement</a>. It was first used primarily in infant formulas.<sup id="cite_ref-41" class="reference"><a href="#cite_note-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> In 2019, the US Food and Drug Administration published qualified <a href="/wiki/Health_claim" title="Health claim">health claims</a> for DHA.<sup id="cite_ref-42" class="reference"><a href="#cite_note-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup> </p><p>Some manufactured DHA is a <a href="/wiki/Vegetarian" class="mw-redirect" title="Vegetarian">vegetarian</a> product extracted from algae, and it competes on the market with fish oil that contains DHA and other omega−3s such as <a href="/wiki/Eicosapentaenoic_acid" title="Eicosapentaenoic acid">EPA</a>. Both fish oil and DHA are odorless and tasteless after processing as a food additive.<sup id="cite_ref-Rivlin_43-0" class="reference"><a href="#cite_note-Rivlin-43"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Studies_of_vegetarians_and_vegans">Studies of vegetarians and vegans</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Docosahexaenoic_acid&action=edit&section=15" title="Edit section: Studies of vegetarians and vegans"><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 article: <a href="/wiki/Vegetarian_nutrition#Omega-3_fatty_acids" title="Vegetarian nutrition">Vegetarian nutrition § Omega-3 fatty acids</a></div> <p><a href="/wiki/Vegetarian" class="mw-redirect" title="Vegetarian">Vegetarian</a> diets typically contain limited amounts of DHA, and <a href="/wiki/Vegan" class="mw-redirect" title="Vegan">vegan</a> diets typically contain no DHA.<sup id="cite_ref-vegetarians_44-0" class="reference"><a href="#cite_note-vegetarians-44"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup> In preliminary research, algae-based <a href="/wiki/Dietary_supplement" title="Dietary supplement">supplements</a> increased DHA levels.<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> While there is little evidence of adverse health or cognitive effects due to DHA deficiency in adult vegetarians or vegans, <a href="/wiki/Breast_milk" title="Breast milk">breast milk</a> levels remain a concern for supplying adequate DHA to the infant.<sup id="cite_ref-vegetarians_44-1" class="reference"><a href="#cite_note-vegetarians-44"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="DHA_and_EPA_in_fish_oils">DHA and EPA in fish oils</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Docosahexaenoic_acid&action=edit&section=16" title="Edit section: DHA and EPA in fish oils"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Fish oil is widely sold in <a href="/wiki/Capsule_(pharmacy)" title="Capsule (pharmacy)">capsules</a> containing a mixture of omega−3 fatty acids, including EPA and DHA. <a href="/wiki/Oxidation" class="mw-redirect" title="Oxidation">Oxidized</a> fish oil in supplement capsules may contain lower levels of EPA and DHA.<sup id="cite_ref-albert1_46-0" class="reference"><a href="#cite_note-albert1-46"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-albert2_47-0" class="reference"><a href="#cite_note-albert2-47"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup> Light, oxygen exposure, and heat can all contribute to oxidation of fish oil supplements.<sup id="cite_ref-albert1_46-1" class="reference"><a href="#cite_note-albert1-46"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-albert2_47-1" class="reference"><a href="#cite_note-albert2-47"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup> Buying a quality product that is kept cold in storage and then keeping it in a refrigerator can help minimize oxidation.<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> </p> <div class="mw-heading mw-heading3"><h3 id="Recommended_daily_DHA_intake_for_children">Recommended daily DHA intake for children</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Docosahexaenoic_acid&action=edit&section=17" title="Edit section: Recommended daily DHA intake for children"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>As optimal DHA level is important for brain development and maturation, there are established daily recommendations for DHA intake in children.<sup id="cite_ref-ods_1-5" class="reference"><a href="#cite_note-ods-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Identifying_reliable_sources_(medicine)" title="Wikipedia:Identifying reliable sources (medicine)"><span title="Material near this tag needs references to reliable medical sources. (March 2024)">medical citation needed</span></a></i>]</sup> </p><p>The table below shows the daily DHA / DHA + EPA intake recommended for children of different ages: </p> <table class="wikitable"> <tbody><tr> <th>PUFAs </th> <th>Age (years) </th> <th>Recommended daily intake </th></tr> <tr> <td>DHA </td> <td>1−2 </td> <td>10 – 12 mg/day </td></tr> <tr> <td rowspan="3">DHA + EPA </td> <td>2−4 </td> <td>100 – 150 mg/day </td></tr> <tr> <td>4−6 </td> <td>150 – 200 mg/day </td></tr> <tr> <td>6−10 </td> <td>200 – 250 mg/day </td></tr></tbody></table> <p>Experts recommend DHA intake of 10–12 mg/day for children 12–24 months, 100–150 mg/day of DHA+EPA for children 2–4 years old and 150–200 mg/day of DHA+EPA for children 4–6 years old.<sup id="cite_ref-ods_1-6" class="reference"><a href="#cite_note-ods-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Identifying_reliable_sources_(medicine)" title="Wikipedia:Identifying reliable sources (medicine)"><span title="Material near this tag needs references to reliable medical sources. (March 2024)">medical citation needed</span></a></i>]</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=Docosahexaenoic_acid&action=edit&section=18" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/DHA-clozapine" title="DHA-clozapine">DHA-clozapine</a></li> <li><a href="/wiki/List_of_omega-3_fatty_acids" title="List of omega-3 fatty acids">List of omega−3 fatty acids</a></li> <li><a href="/wiki/Polyunsaturated_fatty_acid" class="mw-redirect" title="Polyunsaturated fatty acid">Polyunsaturated fatty acids</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=Docosahexaenoic_acid&action=edit&section=19" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-ods-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-ods_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-ods_1-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-ods_1-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-ods_1-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-ods_1-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-ods_1-5"><sup><i><b>f</b></i></sup></a> <a href="#cite_ref-ods_1-6"><sup><i><b>g</b></i></sup></a></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://ods.od.nih.gov/factsheets/Omega3FattyAcids-HealthProfessional/">"Omega-3 fatty acids"</a>. 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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 class="mw-selflink selflink">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 href="/wiki/Linoleic_acid" title="Linoleic acid">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/%CE%93-Linolenic_acid" title="Γ-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="Retinoid_receptor_modulators924" 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:Retinoid_receptor_modulators" title="Template:Retinoid receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Retinoid_receptor_modulators" title="Template talk:Retinoid receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Retinoid_receptor_modulators" title="Special:EditPage/Template:Retinoid receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Retinoid_receptor_modulators924" style="font-size:114%;margin:0 4em"><a href="/wiki/Retinoid_receptor" title="Retinoid receptor">Retinoid receptor</a> <a href="/wiki/Receptor_modulator" title="Receptor modulator">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Retinoic_acid_receptor" title="Retinoic acid receptor"><abbr title="Retinoic acid receptor">RAR</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 Retinoic acid receptor</span></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>Agonists:</i> <a href="/w/index.php?title=9-cis-13,14-Dihydro-retinoic_acid&action=edit&redlink=1" class="new" title="9-cis-13,14-Dihydro-retinoic acid (page does not exist)">9CDHRA</a></li> <li><a href="/wiki/Alitretinoin" title="Alitretinoin">9-<i>cis</i>-Retinoic acid (alitretinoin)</a></li> <li><a href="/w/index.php?title=AC-261066&action=edit&redlink=1" class="new" title="AC-261066 (page does not exist)">AC-261066</a></li> <li><a href="/w/index.php?title=AC-55649&action=edit&redlink=1" class="new" title="AC-55649 (page does not exist)">AC-55649</a></li> <li><a href="/wiki/Acitretin" title="Acitretin">Acitretin</a></li> <li><a href="/wiki/Adapalene" title="Adapalene">Adapalene</a></li> <li><a href="/wiki/Tretinoin" title="Tretinoin">all-<i>trans</i>-Retinoic acid (tretinoin)</a></li> <li><a href="/w/index.php?title=AM-580&action=edit&redlink=1" class="new" title="AM-580 (page does not exist)">AM-580</a></li> <li><a href="/w/index.php?title=BMS-493&action=edit&redlink=1" class="new" title="BMS-493 (page does not exist)">BMS-493</a></li> <li><a href="/w/index.php?title=BMS-753&action=edit&redlink=1" class="new" title="BMS-753 (page does not exist)">BMS-753</a></li> <li><a href="/w/index.php?title=BMS-961&action=edit&redlink=1" class="new" title="BMS-961 (page does not exist)">BMS-961</a></li> <li><a href="/w/index.php?title=CD-1530&action=edit&redlink=1" class="new" title="CD-1530 (page does not exist)">CD-1530</a></li> <li><a href="/w/index.php?title=CD-2314&action=edit&redlink=1" class="new" title="CD-2314 (page does not exist)">CD-2314</a></li> <li><a href="/w/index.php?title=CD-437&action=edit&redlink=1" class="new" title="CD-437 (page does not exist)">CD-437</a></li> <li><a href="/w/index.php?title=Ch-55&action=edit&redlink=1" class="new" title="Ch-55 (page does not exist)">Ch-55</a></li> <li><a href="/w/index.php?title=EC_23&action=edit&redlink=1" class="new" title="EC 23 (page does not exist)">EC 23</a></li> <li><a href="/wiki/Etretinate" title="Etretinate">Etretinate</a></li> <li><a href="/wiki/Fenretinide" title="Fenretinide">Fenretinide</a></li> <li><a href="/wiki/Isotretinoin" title="Isotretinoin">Isotretinoin</a></li> <li><a href="/wiki/Palovarotene" title="Palovarotene">Palovarotene</a></li> <li><a href="/wiki/Retinoic_acid" title="Retinoic acid">Retinoic acid</a></li> <li><a href="/wiki/Retinol" title="Retinol">Retinol</a> (<a href="/wiki/Vitamin_A" title="Vitamin A">vitamin A</a>)</li> <li><a href="/wiki/Tamibarotene" title="Tamibarotene">Tamibarotene</a></li> <li><a href="/wiki/Tazarotene" title="Tazarotene">Tazarotene</a></li> <li><a href="/w/index.php?title=Tazarotenic_acid&action=edit&redlink=1" class="new" title="Tazarotenic acid (page does not exist)">Tazarotenic acid</a></li> <li><a href="/wiki/Trifarotene" title="Trifarotene">Trifarotene</a></li> <li><a href="/w/index.php?title=TTNPB&action=edit&redlink=1" class="new" title="TTNPB (page does not exist)">TTNPB</a></li></ul> <ul><li><i>Antagonists:</i> <a href="/w/index.php?title=BMS-195614&action=edit&redlink=1" class="new" title="BMS-195614 (page does not exist)">BMS-195614</a></li> <li><a href="/w/index.php?title=BMS-493&action=edit&redlink=1" class="new" title="BMS-493 (page does not exist)">BMS-493</a></li> <li><a href="/w/index.php?title=CD-2665&action=edit&redlink=1" class="new" title="CD-2665 (page does not exist)">CD-2665</a></li> <li><a href="/w/index.php?title=ER-50891&action=edit&redlink=1" class="new" title="ER-50891 (page does not exist)">ER-50891</a></li> <li><a href="/w/index.php?title=LE-135&action=edit&redlink=1" class="new" title="LE-135 (page does not exist)">LE-135</a></li> <li><a href="/w/index.php?title=MM-11253&action=edit&redlink=1" class="new" title="MM-11253 (page does not exist)">MM-11253</a></li></ul> <ul><li><i>Retinoic acid metabolism inhibitors:</i> <a href="/wiki/Liarozole" title="Liarozole">Liarozole</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Retinoid_X_receptor" title="Retinoid X receptor"><abbr title="Retinoid X receptor">RXR</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 Retinoid X receptor</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Agonists:</i> <a href="/w/index.php?title=9-cis-13,14-Dihydro-retinoic_acid&action=edit&redlink=1" class="new" title="9-cis-13,14-Dihydro-retinoic acid (page does not exist)">9CDHRA</a></li> <li><a href="/wiki/Alitretinoin" title="Alitretinoin">9-<i>cis</i>-Retinoic acid (alitretinoin)</a></li> <li><a href="/wiki/Tretinoin" title="Tretinoin">all-<i>trans</i>-Retinoic acid (tretinoin)</a></li> <li><a href="/wiki/Bexarotene" title="Bexarotene">Bexarotene</a></li> <li><a href="/w/index.php?title=CD_3254&action=edit&redlink=1" class="new" title="CD 3254 (page does not exist)">CD 3254</a></li> <li><a class="mw-selflink selflink">Docosahexaenoic acid</a></li> <li><a href="/w/index.php?title=Fluorobexarotene&action=edit&redlink=1" class="new" title="Fluorobexarotene (page does not exist)">Fluorobexarotene</a></li> <li><a href="/wiki/Isotretinoin" title="Isotretinoin">Isotretinoin</a></li> <li><a href="/w/index.php?title=LG-100268&action=edit&redlink=1" class="new" title="LG-100268 (page does not exist)">LG-100268</a></li> <li><a href="/w/index.php?title=LG-101506&action=edit&redlink=1" class="new" title="LG-101506 (page does not exist)">LG-101506</a></li> <li><a href="/w/index.php?title=LG-100754&action=edit&redlink=1" class="new" title="LG-100754 (page does not exist)">LG-100754</a></li> <li><a href="/wiki/Retinoic_acid" title="Retinoic acid">Retinoic acid</a></li> <li><a href="/wiki/Retinol" title="Retinol">Retinol</a> (<a href="/wiki/Vitamin_A" title="Vitamin A">vitamin A</a>)</li> <li><a href="/w/index.php?title=SR-11237&action=edit&redlink=1" class="new" title="SR-11237 (page does not exist)">SR-11237</a></li></ul> <ul><li><i>Antagonists:</i> <a href="/w/index.php?title=HX-531&action=edit&redlink=1" class="new" title="HX-531 (page does not exist)">HX-531</a></li> <li><a href="/w/index.php?title=HX-630&action=edit&redlink=1" class="new" title="HX-630 (page does not exist)">HX-630</a></li> <li><a href="/w/index.php?title=LG-100754&action=edit&redlink=1" class="new" title="LG-100754 (page does not exist)">LG-100754</a></li> <li><a href="/w/index.php?title=PA-452&action=edit&redlink=1" class="new" title="PA-452 (page does not exist)">PA-452</a></li> <li><a href="/w/index.php?title=UVI-3003&action=edit&redlink=1" class="new" title="UVI-3003 (page does not exist)">UVI-3003</a></li> <li><a href="/w/index.php?title=HX-603&action=edit&redlink=1" class="new" title="HX-603 (page does not exist)">HX-603</a></li> <li><a href="/w/index.php?title=LE135_(RAR_beta_selective)&action=edit&redlink=1" class="new" title="LE135 (RAR beta selective) (page does not exist)">LE135 (RAR beta selective)</a></li> <li><a href="/w/index.php?title=LE-540&action=edit&redlink=1" class="new" title="LE-540 (page does not exist)">LE-540</a></li> <li><a href="/w/index.php?title=CD3254&action=edit&redlink=1" class="new" title="CD3254 (page does not exist)">CD3254</a></li> <li><a href="/w/index.php?title=PA-451&action=edit&redlink=1" class="new" title="PA-451 (page does not exist)">PA-451</a></li> <li><a href="/w/index.php?title=PA-452&action=edit&redlink=1" class="new" title="PA-452 (page does not exist)">PA-452</a></li> <li><a href="/wiki/Rhein_(molecule)" title="Rhein (molecule)">Rhein</a></li> <li><a href="/w/index.php?title=HX-711&action=edit&redlink=1" class="new" title="HX-711 (page does not exist)">HX-711</a></li> <li><a href="/w/index.php?title=6-(N-ethyl-N-(5-isobutoxy-4-isopropyl-2-(E)-styrylphenyl)amino)nicotinic_acid&action=edit&redlink=1" class="new" title="6-(N-ethyl-N-(5-isobutoxy-4-isopropyl-2-(E)-styrylphenyl)amino)nicotinic acid (page does not exist)">6-(N-ethyl-N-(5-isobutoxy-4-isopropyl-2-(E)-styrylphenyl)amino)nicotinic acid</a></li></ul> </div></td></tr><tr><td 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