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</ul> </li> <li id="toc-Unsaturated_fatty_acids" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Unsaturated_fatty_acids"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.3</span> <span>Unsaturated fatty acids</span> </div> </a> <ul id="toc-Unsaturated_fatty_acids-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Even-_vs_odd-chained_fatty_acids" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Even-_vs_odd-chained_fatty_acids"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.4</span> <span>Even- vs odd-chained fatty acids</span> </div> </a> <ul id="toc-Even-_vs_odd-chained_fatty_acids-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Branching" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Branching"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.5</span> <span>Branching</span> </div> </a> <ul id="toc-Branching-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Nomenclature" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Nomenclature"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Nomenclature</span> </div> </a> <button aria-controls="toc-Nomenclature-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 Nomenclature subsection</span> </button> <ul id="toc-Nomenclature-sublist" class="vector-toc-list"> <li id="toc-Carbon_atom_numbering" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Carbon_atom_numbering"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.1</span> <span>Carbon atom numbering</span> </div> </a> <ul id="toc-Carbon_atom_numbering-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Naming_of_fatty_acids" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Naming_of_fatty_acids"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.2</span> <span>Naming of fatty acids</span> </div> </a> <ul id="toc-Naming_of_fatty_acids-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Free_fatty_acids" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Free_fatty_acids"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.3</span> <span>Free fatty acids</span> </div> </a> <ul id="toc-Free_fatty_acids-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Production" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Production"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Production</span> </div> </a> <button aria-controls="toc-Production-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 Production subsection</span> </button> <ul id="toc-Production-sublist" class="vector-toc-list"> <li id="toc-Industrial" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Industrial"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.1</span> <span>Industrial</span> </div> </a> <ul id="toc-Industrial-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-By_animals" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#By_animals"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.2</span> <span>By animals</span> </div> </a> <ul id="toc-By_animals-sublist" class="vector-toc-list"> <li id="toc-Variation_between_animal_species" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Variation_between_animal_species"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.2.1</span> <span>Variation between animal species</span> </div> </a> <ul id="toc-Variation_between_animal_species-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> </ul> </li> <li id="toc-Fatty_acids_in_dietary_fats" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Fatty_acids_in_dietary_fats"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Fatty acids in dietary fats</span> </div> </a> <ul id="toc-Fatty_acids_in_dietary_fats-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Reactions_of_fatty_acids" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Reactions_of_fatty_acids"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Reactions of fatty acids</span> </div> </a> <button aria-controls="toc-Reactions_of_fatty_acids-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 Reactions of fatty acids subsection</span> </button> <ul id="toc-Reactions_of_fatty_acids-sublist" class="vector-toc-list"> <li id="toc-Acidity" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Acidity"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.1</span> <span>Acidity</span> </div> </a> <ul id="toc-Acidity-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Hydrogenation_and_hardening" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Hydrogenation_and_hardening"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.2</span> <span>Hydrogenation and hardening</span> </div> </a> <ul id="toc-Hydrogenation_and_hardening-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Auto-oxidation_and_rancidity" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Auto-oxidation_and_rancidity"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.3</span> <span>Auto-oxidation and rancidity</span> </div> </a> <ul id="toc-Auto-oxidation_and_rancidity-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Ozonolysis" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Ozonolysis"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.4</span> <span>Ozonolysis</span> </div> </a> <ul id="toc-Ozonolysis-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Circulation" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Circulation"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Circulation</span> </div> </a> <button aria-controls="toc-Circulation-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 Circulation subsection</span> </button> <ul id="toc-Circulation-sublist" class="vector-toc-list"> <li id="toc-Digestion_and_intake" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Digestion_and_intake"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.1</span> <span>Digestion and intake</span> </div> </a> <ul id="toc-Digestion_and_intake-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Metabolism" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Metabolism"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.2</span> <span>Metabolism</span> </div> </a> <ul id="toc-Metabolism-sublist" class="vector-toc-list"> <li id="toc-Essential_fatty_acids" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Essential_fatty_acids"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.2.1</span> <span>Essential fatty acids</span> </div> </a> <ul id="toc-Essential_fatty_acids-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Distribution" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Distribution"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.3</span> <span>Distribution</span> </div> </a> <ul id="toc-Distribution-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Skin" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Skin"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>Skin</span> </div> </a> <ul id="toc-Skin-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Analysis" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Analysis"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>Analysis</span> </div> </a> <ul id="toc-Analysis-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Industrial_uses" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Industrial_uses"> <div class="vector-toc-text"> <span class="vector-toc-numb">10</span> <span>Industrial uses</span> </div> </a> <ul id="toc-Industrial_uses-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">11</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"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">12</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">13</span> <span>External links</span> </div> </a> <ul id="toc-External_links-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span 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Available in 71 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-71" 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">71 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%AF%D9%87%D9%86%D9%8A" title="حمض دهني – Arabic" lang="ar" hreflang="ar" data-title="حمض دهني" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-ast mw-list-item"><a href="https://ast.wikipedia.org/wiki/%C3%81cidu_graso" title="Ácidu graso – Asturian" lang="ast" hreflang="ast" data-title="Ácidu graso" data-language-autonym="Asturianu" data-language-local-name="Asturian" class="interlanguage-link-target"><span>Asturianu</span></a></li><li class="interlanguage-link interwiki-bn mw-list-item"><a href="https://bn.wikipedia.org/wiki/%E0%A6%B8%E0%A7%8D%E0%A6%A8%E0%A7%87%E0%A6%B9%E0%A6%9C_%E0%A6%85%E0%A7%8D%E0%A6%AF%E0%A6%BE%E0%A6%B8%E0%A6%BF%E0%A6%A1" title="স্নেহজ অ্যাসিড – Bangla" lang="bn" hreflang="bn" data-title="স্নেহজ অ্যাসিড" data-language-autonym="বাংলা" data-language-local-name="Bangla" class="interlanguage-link-target"><span>বাংলা</span></a></li><li class="interlanguage-link interwiki-be mw-list-item"><a href="https://be.wikipedia.org/wiki/%D0%A2%D0%BB%D1%83%D1%81%D1%82%D1%8B%D1%8F_%D0%BA%D1%96%D1%81%D0%BB%D0%BE%D1%82%D1%8B" title="Тлустыя кіслоты – Belarusian" lang="be" hreflang="be" data-title="Тлустыя кіслоты" data-language-autonym="Беларуская" data-language-local-name="Belarusian" class="interlanguage-link-target"><span>Беларуская</span></a></li><li class="interlanguage-link interwiki-be-x-old mw-list-item"><a href="https://be-tarask.wikipedia.org/wiki/%D0%A2%D0%BB%D1%83%D1%81%D1%82%D1%8B%D1%8F_%D0%BA%D1%96%D1%81%D1%8C%D0%BB%D1%96" title="Тлустыя кісьлі – Belarusian (Taraškievica orthography)" lang="be-tarask" hreflang="be-tarask" data-title="Тлустыя кісьлі" data-language-autonym="Беларуская (тарашкевіца)" data-language-local-name="Belarusian (Taraškievica orthography)" class="interlanguage-link-target"><span>Беларуская (тарашкевіца)</span></a></li><li class="interlanguage-link interwiki-bcl mw-list-item"><a href="https://bcl.wikipedia.org/wiki/Asidong_mataba" title="Asidong mataba – Central Bikol" lang="bcl" hreflang="bcl" data-title="Asidong mataba" data-language-autonym="Bikol Central" data-language-local-name="Central Bikol" class="interlanguage-link-target"><span>Bikol Central</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%9C%D0%B0%D1%81%D1%82%D0%BD%D0%B0_%D0%BA%D0%B8%D1%81%D0%B5%D0%BB%D0%B8%D0%BD%D0%B0" title="Мастна киселина – Bulgarian" lang="bg" hreflang="bg" data-title="Мастна киселина" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target"><span>Български</span></a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Masne_kiseline" title="Masne kiseline – Bosnian" lang="bs" hreflang="bs" data-title="Masne kiseline" data-language-autonym="Bosanski" data-language-local-name="Bosnian" class="interlanguage-link-target"><span>Bosanski</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/%C3%80cid_gras" title="Àcid gras – Catalan" lang="ca" hreflang="ca" data-title="Àcid gras" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Mastn%C3%A1_kyselina" title="Mastná kyselina – Czech" lang="cs" hreflang="cs" data-title="Mastná kyselina" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Fedtsyre" title="Fedtsyre – Danish" lang="da" hreflang="da" data-title="Fedtsyre" 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/Fetts%C3%A4uren" title="Fettsäuren – German" lang="de" hreflang="de" data-title="Fettsäuren" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/Rasvhapped" title="Rasvhapped – Estonian" lang="et" hreflang="et" data-title="Rasvhapped" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%9B%CE%B9%CF%80%CE%B1%CF%81%CF%8C_%CE%BF%CE%BE%CF%8D" title="Λιπαρό οξύ – Greek" lang="el" hreflang="el" data-title="Λιπαρό οξύ" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target"><span>Ελληνικά</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/%C3%81cido_graso" title="Ácido graso – Spanish" lang="es" hreflang="es" data-title="Ácido graso" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eo mw-list-item"><a href="https://eo.wikipedia.org/wiki/Grasacido" title="Grasacido – Esperanto" lang="eo" hreflang="eo" data-title="Grasacido" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Gantz-azido" title="Gantz-azido – Basque" lang="eu" hreflang="eu" data-title="Gantz-azido" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%A7%D8%B3%DB%8C%D8%AF_%DA%86%D8%B1%D8%A8" title="اسید چرب – Persian" lang="fa" hreflang="fa" data-title="اسید چرب" 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_gras" title="Acide gras – French" lang="fr" hreflang="fr" data-title="Acide gras" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ga mw-list-item"><a href="https://ga.wikipedia.org/wiki/Aig%C3%A9ad_sailleach" title="Aigéad sailleach – Irish" lang="ga" hreflang="ga" data-title="Aigéad sailleach" data-language-autonym="Gaeilge" data-language-local-name="Irish" class="interlanguage-link-target"><span>Gaeilge</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/%C3%81cido_graxo" title="Ácido graxo – Galician" lang="gl" hreflang="gl" data-title="Ácido graxo" 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/%EC%A7%80%EB%B0%A9%EC%82%B0" title="지방산 – Korean" lang="ko" hreflang="ko" data-title="지방산" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D5%83%D5%A1%D6%80%D5%BA%D5%A1%D5%A9%D5%A9%D5%B8%D6%82%D5%B6%D5%A5%D6%80" title="Ճարպաթթուներ – Armenian" lang="hy" hreflang="hy" data-title="Ճարպաթթուներ" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-hi mw-list-item"><a href="https://hi.wikipedia.org/wiki/%E0%A4%B5%E0%A4%B8%E0%A4%BE_%E0%A4%85%E0%A4%AE%E0%A5%8D%E0%A4%B2" title="वसा अम्ल – Hindi" lang="hi" hreflang="hi" data-title="वसा अम्ल" data-language-autonym="हिन्दी" data-language-local-name="Hindi" class="interlanguage-link-target"><span>हिन्दी</span></a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Masne_kiseline" title="Masne kiseline – Croatian" lang="hr" hreflang="hr" data-title="Masne kiseline" 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_lemak" title="Asam lemak – Indonesian" lang="id" hreflang="id" data-title="Asam lemak" 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-is mw-list-item"><a href="https://is.wikipedia.org/wiki/Fitus%C3%BDra" title="Fitusýra – Icelandic" lang="is" hreflang="is" data-title="Fitusýra" data-language-autonym="Íslenska" data-language-local-name="Icelandic" class="interlanguage-link-target"><span>Íslenska</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Acidi_grassi" title="Acidi grassi – Italian" lang="it" hreflang="it" data-title="Acidi grassi" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%97%D7%95%D7%9E%D7%A6%D7%AA_%D7%A9%D7%95%D7%9E%D7%9F" title="חומצת שומן – Hebrew" lang="he" hreflang="he" data-title="חומצת שומן" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-jv mw-list-item"><a href="https://jv.wikipedia.org/wiki/Asem_lemak" title="Asem lemak – Javanese" lang="jv" hreflang="jv" data-title="Asem lemak" data-language-autonym="Jawa" data-language-local-name="Javanese" class="interlanguage-link-target"><span>Jawa</span></a></li><li class="interlanguage-link interwiki-kn mw-list-item"><a href="https://kn.wikipedia.org/wiki/%E0%B2%95%E0%B3%8A%E0%B2%AC%E0%B3%8D%E0%B2%AC%E0%B2%BF%E0%B2%A8_%E0%B2%86%E0%B2%AE%E0%B3%8D%E0%B2%B2" title="ಕೊಬ್ಬಿನ ಆಮ್ಲ – Kannada" lang="kn" hreflang="kn" data-title="ಕೊಬ್ಬಿನ ಆಮ್ಲ" data-language-autonym="ಕನ್ನಡ" data-language-local-name="Kannada" class="interlanguage-link-target"><span>ಕನ್ನಡ</span></a></li><li class="interlanguage-link interwiki-kk mw-list-item"><a href="https://kk.wikipedia.org/wiki/%D0%9C%D0%B0%D0%B9%D0%BB%D1%8B_%D2%9B%D1%8B%D1%88%D2%9B%D1%8B%D0%BB%D0%B4%D0%B0%D1%80" title="Майлы қышқылдар – Kazakh" lang="kk" hreflang="kk" data-title="Майлы қышқылдар" data-language-autonym="Қазақша" data-language-local-name="Kazakh" class="interlanguage-link-target"><span>Қазақша</span></a></li><li class="interlanguage-link interwiki-ht mw-list-item"><a href="https://ht.wikipedia.org/wiki/Asid_gra" title="Asid gra – Haitian Creole" lang="ht" hreflang="ht" data-title="Asid gra" data-language-autonym="Kreyòl ayisyen" data-language-local-name="Haitian Creole" class="interlanguage-link-target"><span>Kreyòl ayisyen</span></a></li><li class="interlanguage-link interwiki-ky mw-list-item"><a href="https://ky.wikipedia.org/wiki/%D0%9C%D0%B0%D0%B9_%D0%BA%D0%B8%D1%81%D0%BB%D0%BE%D1%82%D0%B0%D0%BB%D0%B0%D1%80%D1%8B" title="Май кислоталары – Kyrgyz" lang="ky" hreflang="ky" data-title="Май кислоталары" data-language-autonym="Кыргызча" data-language-local-name="Kyrgyz" class="interlanguage-link-target"><span>Кыргызча</span></a></li><li class="interlanguage-link interwiki-la mw-list-item"><a href="https://la.wikipedia.org/wiki/Acidum_adipatum" title="Acidum adipatum – Latin" lang="la" hreflang="la" data-title="Acidum adipatum" data-language-autonym="Latina" data-language-local-name="Latin" class="interlanguage-link-target"><span>Latina</span></a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Tauksk%C4%81bes" title="Taukskābes – Latvian" lang="lv" hreflang="lv" data-title="Taukskābes" 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/Riebal%C5%B3_r%C5%ABg%C5%A1tys" title="Riebalų rūgštys – Lithuanian" lang="lt" hreflang="lt" data-title="Riebalų rūgštys" data-language-autonym="Lietuvių" data-language-local-name="Lithuanian" class="interlanguage-link-target"><span>Lietuvių</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Zs%C3%ADrsavak" title="Zsírsavak – Hungarian" lang="hu" hreflang="hu" data-title="Zsírsavak" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%9C%D0%B0%D1%81%D0%BD%D0%B0_%D0%BA%D0%B8%D1%81%D0%B5%D0%BB%D0%B8%D0%BD%D0%B0" title="Масна киселина – Macedonian" lang="mk" hreflang="mk" data-title="Масна киселина" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-ml mw-list-item"><a href="https://ml.wikipedia.org/wiki/%E0%B4%AB%E0%B4%BE%E0%B4%B1%E0%B5%8D%E0%B4%B1%E0%B4%BF_%E0%B4%86%E0%B4%B8%E0%B4%BF%E0%B4%A1%E0%B5%8D" title="ഫാറ്റി ആസിഡ് – Malayalam" lang="ml" hreflang="ml" data-title="ഫാറ്റി ആസിഡ്" data-language-autonym="മലയാളം" data-language-local-name="Malayalam" class="interlanguage-link-target"><span>മലയാളം</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Asid_lemak" title="Asid lemak – Malay" lang="ms" hreflang="ms" data-title="Asid lemak" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" class="interlanguage-link-target"><span>Bahasa Melayu</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Vetzuur" title="Vetzuur – Dutch" lang="nl" hreflang="nl" data-title="Vetzuur" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E8%84%82%E8%82%AA%E9%85%B8" title="脂肪酸 – Japanese" lang="ja" hreflang="ja" data-title="脂肪酸" 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-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Fettsyre" title="Fettsyre – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Fettsyre" data-language-autonym="Norsk bokmål" data-language-local-name="Norwegian Bokmål" class="interlanguage-link-target"><span>Norsk bokmål</span></a></li><li class="interlanguage-link interwiki-nn mw-list-item"><a href="https://nn.wikipedia.org/wiki/Feittsyre" title="Feittsyre – Norwegian Nynorsk" lang="nn" hreflang="nn" data-title="Feittsyre" data-language-autonym="Norsk nynorsk" data-language-local-name="Norwegian Nynorsk" class="interlanguage-link-target"><span>Norsk nynorsk</span></a></li><li class="interlanguage-link interwiki-oc mw-list-item"><a href="https://oc.wikipedia.org/wiki/Acid_gras" title="Acid gras – Occitan" lang="oc" hreflang="oc" data-title="Acid gras" data-language-autonym="Occitan" data-language-local-name="Occitan" class="interlanguage-link-target"><span>Occitan</span></a></li><li class="interlanguage-link interwiki-om mw-list-item"><a href="https://om.wikipedia.org/wiki/Dhangaggee_coomaa" title="Dhangaggee coomaa – Oromo" lang="om" hreflang="om" data-title="Dhangaggee coomaa" data-language-autonym="Oromoo" data-language-local-name="Oromo" class="interlanguage-link-target"><span>Oromoo</span></a></li><li class="interlanguage-link interwiki-pa mw-list-item"><a href="https://pa.wikipedia.org/wiki/%E0%A8%9A%E0%A8%B0%E0%A8%AC%E0%A9%80%E0%A8%B2%E0%A8%BE_%E0%A8%A4%E0%A8%BF%E0%A8%9C%E0%A8%BC%E0%A8%BE%E0%A8%AC" title="ਚਰਬੀਲਾ ਤਿਜ਼ਾਬ – Punjabi" lang="pa" hreflang="pa" data-title="ਚਰਬੀਲਾ ਤਿਜ਼ਾਬ" data-language-autonym="ਪੰਜਾਬੀ" data-language-local-name="Punjabi" class="interlanguage-link-target"><span>ਪੰਜਾਬੀ</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Kwasy_t%C5%82uszczowe" title="Kwasy tłuszczowe – Polish" lang="pl" hreflang="pl" data-title="Kwasy tłuszczowe" 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_graxo" title="Ácido graxo – Portuguese" lang="pt" hreflang="pt" data-title="Ácido graxo" 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_gras" title="Acid gras – Romanian" lang="ro" hreflang="ro" data-title="Acid gras" 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%96%D0%B8%D1%80%D0%BD%D1%8B%D0%B5_%D0%BA%D0%B8%D1%81%D0%BB%D0%BE%D1%82%D1%8B" title="Жирные кислоты – Russian" lang="ru" hreflang="ru" data-title="Жирные кислоты" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sq mw-list-item"><a href="https://sq.wikipedia.org/wiki/Acidi_yndyror" title="Acidi yndyror – Albanian" lang="sq" hreflang="sq" data-title="Acidi yndyror" data-language-autonym="Shqip" data-language-local-name="Albanian" class="interlanguage-link-target"><span>Shqip</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Fatty_acid" title="Fatty acid – Simple English" lang="en-simple" hreflang="en-simple" data-title="Fatty acid" data-language-autonym="Simple English" data-language-local-name="Simple English" class="interlanguage-link-target"><span>Simple English</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Mastn%C3%A1_kyselina" title="Mastná kyselina – Slovak" lang="sk" hreflang="sk" data-title="Mastná kyselina" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Ma%C5%A1%C4%8Dobna_kislina" title="Maščobna kislina – Slovenian" lang="sl" hreflang="sl" data-title="Maščobna kislina" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-ckb mw-list-item"><a href="https://ckb.wikipedia.org/wiki/%D8%AA%D8%B1%D8%B4%DB%8C_%DA%86%DB%95%D9%88%D8%B1%DB%8C" title="ترشی چەوری – Central Kurdish" lang="ckb" hreflang="ckb" data-title="ترشی چەوری" data-language-autonym="کوردی" data-language-local-name="Central Kurdish" class="interlanguage-link-target"><span>کوردی</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Masna_kiselina" title="Masna kiselina – Serbian" lang="sr" hreflang="sr" data-title="Masna 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/Masne_kiseline" title="Masne kiseline – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Masne kiseline" 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_lemak" title="Asam lemak – Sundanese" lang="su" hreflang="su" data-title="Asam lemak" 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/Rasvahapot" title="Rasvahapot – Finnish" lang="fi" hreflang="fi" data-title="Rasvahapot" 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/Fettsyra" title="Fettsyra – Swedish" lang="sv" hreflang="sv" data-title="Fettsyra" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%95%E0%AF%8A%E0%AE%B4%E0%AF%81%E0%AE%AA%E0%AF%8D%E0%AE%AA%E0%AF%81_%E0%AE%85%E0%AE%AE%E0%AE%BF%E0%AE%B2%E0%AE%AE%E0%AF%8D" title="கொழுப்பு அமிலம் – Tamil" lang="ta" hreflang="ta" data-title="கொழுப்பு அமிலம்" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-te mw-list-item"><a href="https://te.wikipedia.org/wiki/%E0%B0%95%E0%B1%8A%E0%B0%B5%E0%B1%8D%E0%B0%B5%E0%B1%81_%E0%B0%86%E0%B0%AE%E0%B1%8D%E0%B0%B2%E0%B0%82" title="కొవ్వు ఆమ్లం – Telugu" lang="te" hreflang="te" data-title="కొవ్వు ఆమ్లం" data-language-autonym="తెలుగు" data-language-local-name="Telugu" class="interlanguage-link-target"><span>తెలుగు</span></a></li><li class="interlanguage-link interwiki-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B8%81%E0%B8%A3%E0%B8%94%E0%B9%84%E0%B8%82%E0%B8%A1%E0%B8%B1%E0%B8%99" title="กรดไขมัน – Thai" lang="th" hreflang="th" data-title="กรดไขมัน" data-language-autonym="ไทย" data-language-local-name="Thai" class="interlanguage-link-target"><span>ไทย</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Ya%C4%9F_asidi" title="Yağ asidi – Turkish" lang="tr" hreflang="tr" data-title="Yağ asidi" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%96%D0%B8%D1%80%D0%BD%D1%96_%D0%BA%D0%B8%D1%81%D0%BB%D0%BE%D1%82%D0%B8" title="Жирні кислоти – Ukrainian" lang="uk" hreflang="uk" data-title="Жирні кислоти" 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_b%C3%A9o" title="Acid béo – Vietnamese" lang="vi" hreflang="vi" data-title="Acid béo" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target"><span>Tiếng Việt</span></a></li><li class="interlanguage-link interwiki-wuu mw-list-item"><a href="https://wuu.wikipedia.org/wiki/%E8%84%82%E8%82%AA%E9%85%B8" title="脂肪酸 – Wu" lang="wuu" hreflang="wuu" data-title="脂肪酸" 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-yue mw-list-item"><a href="https://zh-yue.wikipedia.org/wiki/%E8%84%82%E8%82%AA%E9%85%B8" title="脂肪酸 – Cantonese" lang="yue" hreflang="yue" data-title="脂肪酸" data-language-autonym="粵語" data-language-local-name="Cantonese" class="interlanguage-link-target"><span>粵語</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E8%84%82%E8%82%AA%E9%85%B8" title="脂肪酸 – Chinese" lang="zh" hreflang="zh" data-title="脂肪酸" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target"><span>中文</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span class="wb-langlinks-edit wb-langlinks-link"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q61476#sitelinks-wikipedia" title="Edit interlanguage links" class="wbc-editpage">Edit links</a></span></div> </div> 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.sidebar-title-with-pretitle{background:transparent!important}html.skin-theme-clientpref-night .mw-parser-output .sidebar:not(.notheme) .sidebar-title-with-pretitle a{color:var(--color-progressive)!important}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .sidebar:not(.notheme) .sidebar-list-title,html.skin-theme-clientpref-os .mw-parser-output .sidebar:not(.notheme) .sidebar-title-with-pretitle{background:transparent!important}html.skin-theme-clientpref-os .mw-parser-output .sidebar:not(.notheme) .sidebar-title-with-pretitle a{color:var(--color-progressive)!important}}@media print{body.ns-0 .mw-parser-output .sidebar{display:none!important}}</style><table class="sidebar nomobile nowraplinks" style="width:16em"><tbody><tr><th class="sidebar-title" style="background:#eee">Types of <a href="/wiki/Fat" title="Fat">fats</a> in <a href="/wiki/Food" title="Food">food</a></th></tr><tr><td class="sidebar-content" style="text-align:left"> <ul><li><a href="/wiki/Saturated_fat" title="Saturated fat">Saturated fat</a></li> <li><a href="/wiki/Unsaturated_fat" title="Unsaturated fat">Unsaturated fat</a> <ul><li><a href="/wiki/Monounsaturated_fat" title="Monounsaturated fat">Monounsaturated fat</a></li> <li><a href="/wiki/Polyunsaturated_fat" title="Polyunsaturated fat">Polyunsaturated fat</a></li></ul></li></ul></td> </tr><tr><th class="sidebar-heading" style="background:#eee"> Components</th></tr><tr><td class="sidebar-content" style="text-align:left"> <ul><li><a class="mw-selflink selflink">Fatty acid</a> (<a href="/wiki/Essential_fatty_acid" title="Essential fatty acid">Essential fatty acid</a>) <ul><li><a href="/wiki/Omega-3_fatty_acid" title="Omega-3 fatty acid">Omega−3</a></li> <li><a href="/wiki/Omega-6_fatty_acid" title="Omega-6 fatty acid">Omega−6</a></li> <li><a href="/wiki/Omega-7_fatty_acid" title="Omega-7 fatty acid">Omega−7</a></li> <li><a href="/wiki/Omega-9_fatty_acid" title="Omega-9 fatty acid">Omega−9</a></li></ul></li> <li><a href="/wiki/Triglyceride" title="Triglyceride">Triglyceride</a></li> <li><a href="/wiki/Cholesterol" title="Cholesterol">Cholesterol</a></li></ul></td> </tr><tr><th class="sidebar-heading" style="background:#eee"> Manufactured fats</th></tr><tr><td class="sidebar-content" style="text-align:left"> <ul><li><a href="/wiki/Fat_hydrogenation" title="Fat hydrogenation">Fat hydrogenation</a> <ul><li><a href="/wiki/Trans_fat" title="Trans fat">Trans fat</a></li></ul></li> <li><a href="/wiki/Fat_interesterification" title="Fat interesterification">Fat interesterification</a></li></ul></td> </tr><tr><td class="sidebar-navbar"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><style data-mw-deduplicate="TemplateStyles:r1239400231">.mw-parser-output .navbar{display:inline;font-size:88%;font-weight:normal}.mw-parser-output .navbar-collapse{float:left;text-align:left}.mw-parser-output .navbar-boxtext{word-spacing:0}.mw-parser-output .navbar ul{display:inline-block;white-space:nowrap;line-height:inherit}.mw-parser-output .navbar-brackets::before{margin-right:-0.125em;content:"[ "}.mw-parser-output .navbar-brackets::after{margin-left:-0.125em;content:" ]"}.mw-parser-output .navbar li{word-spacing:-0.125em}.mw-parser-output .navbar a>span,.mw-parser-output .navbar a>abbr{text-decoration:inherit}.mw-parser-output .navbar-mini abbr{font-variant:small-caps;border-bottom:none;text-decoration:none;cursor:inherit}.mw-parser-output .navbar-ct-full{font-size:114%;margin:0 7em}.mw-parser-output .navbar-ct-mini{font-size:114%;margin:0 4em}html.skin-theme-clientpref-night .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}@media(prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}}@media print{.mw-parser-output .navbar{display:none!important}}</style><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Fats" title="Template:Fats"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Fats" title="Template talk:Fats"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Fats" title="Special:EditPage/Template:Fats"><abbr title="Edit this template">e</abbr></a></li></ul></div></td></tr></tbody></table> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Rasyslami.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/19/Rasyslami.jpg/300px-Rasyslami.jpg" decoding="async" width="300" height="225" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/1/19/Rasyslami.jpg 1.5x" data-file-width="432" data-file-height="324" /></a><figcaption>Three-dimensional representations of several fatty acids. <a href="/wiki/Saturated_and_unsaturated_compounds" title="Saturated and unsaturated compounds">Saturated</a> fatty acids have perfectly straight chain structure. <a href="/wiki/Unsaturated_compound" class="mw-redirect" title="Unsaturated compound">Unsaturated</a> ones are typically bent, unless they have a <a href="#Unsaturated_fatty_acids">trans</a> configuration.</figcaption></figure> <p>In <a href="/wiki/Chemistry" title="Chemistry">chemistry</a>, particularly in <a href="/wiki/Biochemistry" title="Biochemistry">biochemistry</a>, a <b>fatty acid</b> is a <a href="/wiki/Carboxylic_acid" title="Carboxylic acid">carboxylic acid</a> with an <a href="/wiki/Aliphatic" class="mw-redirect" title="Aliphatic">aliphatic</a> chain, which is either <a href="/wiki/Saturated_and_unsaturated_compounds#Organic_chemistry" title="Saturated and unsaturated compounds">saturated or unsaturated</a>. Most naturally occurring fatty acids have an <a href="/wiki/Branched_chain_fatty_acids" class="mw-redirect" title="Branched chain fatty acids">unbranched chain</a> of an even number of carbon atoms, from 4 to 28.<sup id="cite_ref-iupac_1-0" class="reference"><a href="#cite_note-iupac-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Fatty acids are a major component of the lipids (up to 70% by weight) in some species such as microalgae<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> but in some other organisms are not found in their standalone form, but instead exist as three main classes of <a href="/wiki/Ester" title="Ester">esters</a>: <a href="/wiki/Triglyceride" title="Triglyceride">triglycerides</a>, <a href="/wiki/Phospholipid" title="Phospholipid">phospholipids</a>, and <a href="/wiki/Cholesteryl_ester" title="Cholesteryl ester">cholesteryl esters</a>. In any of these forms, fatty acids are both important <a href="/wiki/Diet_(nutrition)" title="Diet (nutrition)">dietary</a> sources of fuel for animals and important structural components for <a href="/wiki/Cell_(biology)" title="Cell (biology)">cells</a>. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="History">History</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fatty_acid&action=edit&section=1" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The concept of fatty acid (<i>acide gras</i>) was introduced in 1813 by <a href="/wiki/Michel_Eug%C3%A8ne_Chevreul" title="Michel Eugène Chevreul">Michel Eugène Chevreul</a>,<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><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><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> though he initially used some variant terms: <i>graisse acide</i> and <i>acide huileux</i> ("acid fat" and "oily acid").<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> </p> <div class="mw-heading mw-heading2"><h2 id="Types_of_fatty_acids">Types of fatty acids</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fatty_acid&action=edit&section=2" title="Edit section: Types of fatty acids"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Isomers_of_oleic_acid.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/88/Isomers_of_oleic_acid.svg/300px-Isomers_of_oleic_acid.svg.png" decoding="async" width="300" height="133" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/88/Isomers_of_oleic_acid.svg/450px-Isomers_of_oleic_acid.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/88/Isomers_of_oleic_acid.svg/600px-Isomers_of_oleic_acid.svg.png 2x" data-file-width="1175" data-file-height="520" /></a><figcaption>Comparison of the <a href="/wiki/Cis%E2%80%93trans_isomerism" title="Cis–trans isomerism"><i>trans</i> isomer</a> <a href="/wiki/Elaidic_acid" title="Elaidic acid">elaidic acid</a> (top) and the <i>cis</i> isomer <a href="/wiki/Oleic_acid" title="Oleic acid">oleic acid</a> (bottom)</figcaption></figure> <p>Fatty acids are classified in many ways: by length, by saturation vs unsaturation, by even vs odd carbon content, and by linear vs branched. </p> <div class="mw-heading mw-heading3"><h3 id="Length_of_fatty_acids">Length of fatty acids</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fatty_acid&action=edit&section=3" title="Edit section: Length of fatty acids"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Short-chain_fatty_acids" class="mw-redirect" title="Short-chain fatty acids">Short-chain fatty acids</a> (SCFAs) are fatty acids with <a href="/wiki/Aliphatic" class="mw-redirect" title="Aliphatic">aliphatic</a> tails of five or fewer <a href="/wiki/Carbon" title="Carbon">carbons</a> (e.g. <a href="/wiki/Butyric_acid" title="Butyric acid">butyric acid</a>).<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></li> <li>Medium-chain fatty acids (MCFAs) are fatty acids with aliphatic tails of 6 to 12<sup id="cite_ref-e-medicine_8-0" class="reference"><a href="#cite_note-e-medicine-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> carbons, which can form <a href="/wiki/Medium-chain_triglyceride" title="Medium-chain triglyceride">medium-chain triglycerides</a>.</li> <li>Long-chain fatty acids (LCFAs) are fatty acids with aliphatic tails of 13 to 21 carbons.<sup id="cite_ref-lipidworld_9-0" class="reference"><a href="#cite_note-lipidworld-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup></li> <li><a href="/wiki/Very_long_chain_fatty_acids" class="mw-redirect" title="Very long chain fatty acids">Very long chain fatty acids</a> (VLCFAs) are fatty acids with aliphatic tails of 22 or more carbons.</li></ul> <div class="mw-heading mw-heading3"><h3 id="Saturated_fatty_acids">Saturated fatty acids</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fatty_acid&action=edit&section=4" title="Edit section: Saturated fatty acids"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Saturated_fat" title="Saturated fat">Saturated fat</a></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">For a more comprehensive list, see <a href="/wiki/List_of_saturated_fatty_acids" title="List of saturated fatty acids">List of saturated fatty acids</a>.</div> <p>Saturated fatty acids have no C=C double bonds. They have the formula CH<sub>3</sub>(CH<sub>2</sub>)<sub>n</sub>COOH, for different <i>n</i>. An important saturated fatty acid is <a href="/wiki/Stearic_acid" title="Stearic acid">stearic acid</a> (<i>n</i> = 16), which when neutralized with <a href="/wiki/Sodium_hydroxide" title="Sodium hydroxide">sodium hydroxide</a> is the most common form of <a href="/wiki/Soap" title="Soap">soap</a>. </p> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Arachidic_formula_representation.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/05/Arachidic_formula_representation.svg/300px-Arachidic_formula_representation.svg.png" decoding="async" width="300" height="261" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/05/Arachidic_formula_representation.svg/450px-Arachidic_formula_representation.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/05/Arachidic_formula_representation.svg/600px-Arachidic_formula_representation.svg.png 2x" data-file-width="433" data-file-height="377" /></a><figcaption><a href="/wiki/Arachidic_acid" title="Arachidic acid">Arachidic acid</a>, a saturated fatty acid</figcaption></figure> <table class="wikitable"> <caption>Examples of saturated fatty acids </caption> <tbody><tr> <th>Common name</th> <th>Chemical structure</th> <th><i>C</i>:<i>D</i><sup id="cite_ref-c:d_10-0" class="reference"><a href="#cite_note-c:d-10"><span class="cite-bracket">[</span>a<span class="cite-bracket">]</span></a></sup> </th></tr> <tr> <td><a href="/wiki/Caprylic_acid" title="Caprylic acid">Caprylic acid</a></td> <td>CH<sub>3</sub>(CH<sub>2</sub>)<sub>6</sub>COOH</td> <td>8:0 </td></tr> <tr> <td><a href="/wiki/Capric_acid" title="Capric acid">Capric acid</a></td> <td>CH<sub>3</sub>(CH<sub>2</sub>)<sub>8</sub>COOH</td> <td>10:0 </td></tr> <tr> <td><a href="/wiki/Lauric_acid" title="Lauric acid">Lauric acid</a></td> <td>CH<sub>3</sub>(CH<sub>2</sub>)<sub>10</sub>COOH</td> <td>12:0 </td></tr> <tr> <td><a href="/wiki/Myristic_acid" title="Myristic acid">Myristic acid</a></td> <td>CH<sub>3</sub>(CH<sub>2</sub>)<sub>12</sub>COOH</td> <td>14:0 </td></tr> <tr> <td><a href="/wiki/Palmitic_acid" title="Palmitic acid">Palmitic acid</a></td> <td>CH<sub>3</sub>(CH<sub>2</sub>)<sub>14</sub>COOH</td> <td>16:0 </td></tr> <tr> <td><a href="/wiki/Stearic_acid" title="Stearic acid">Stearic acid</a></td> <td>CH<sub>3</sub>(CH<sub>2</sub>)<sub>16</sub>COOH</td> <td>18:0 </td></tr> <tr> <td><a href="/wiki/Arachidic_acid" title="Arachidic acid">Arachidic acid</a></td> <td>CH<sub>3</sub>(CH<sub>2</sub>)<sub>18</sub>COOH</td> <td>20:0 </td></tr> <tr> <td><a href="/wiki/Behenic_acid" title="Behenic acid">Behenic acid</a></td> <td>CH<sub>3</sub>(CH<sub>2</sub>)<sub>20</sub>COOH</td> <td>22:0 </td></tr> <tr> <td><a href="/wiki/Lignoceric_acid" title="Lignoceric acid">Lignoceric acid</a></td> <td>CH<sub>3</sub>(CH<sub>2</sub>)<sub>22</sub>COOH</td> <td>24:0 </td></tr> <tr> <td><a href="/wiki/Cerotic_acid" title="Cerotic acid">Cerotic acid</a></td> <td>CH<sub>3</sub>(CH<sub>2</sub>)<sub>24</sub>COOH</td> <td>26:0 </td></tr></tbody></table> <div class="mw-heading mw-heading3"><h3 id="Unsaturated_fatty_acids">Unsaturated fatty acids</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fatty_acid&action=edit&section=5" title="Edit section: Unsaturated fatty acids"><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/Unsaturated_fat" title="Unsaturated fat">Unsaturated fat</a></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">For a more comprehensive list, see <a href="/wiki/List_of_unsaturated_fatty_acids" title="List of unsaturated fatty acids">List of unsaturated fatty acids</a>.</div> <p>Unsaturated fatty acids have one or more C=C <a href="/wiki/Double_bond" title="Double bond">double bonds</a>. The C=C double bonds can give either <a href="/wiki/Cis-trans_isomerism" class="mw-redirect" title="Cis-trans isomerism"><i>cis</i> or <i>trans</i></a> isomers. </p> <dl><dt><i>cis</i></dt> <dd>A <i>cis</i> configuration means that the two hydrogen atoms adjacent to the double bond stick out on the same side of the chain. The rigidity of the double bond freezes its conformation and, in the case of the <i>cis</i> isomer, causes the chain to bend and restricts the conformational freedom of the fatty acid. The more double bonds the chain has in the <i>cis</i> configuration, the less flexibility it has. When a chain has many <i>cis</i> bonds, it becomes quite curved in its most accessible conformations. For example, <a href="/wiki/Oleic_acid" title="Oleic acid">oleic acid</a>, with one double bond, has a "kink" in it, whereas <a href="/wiki/Linoleic_acid" title="Linoleic acid">linoleic acid</a>, with two double bonds, has a more pronounced bend. <a href="/wiki/%CE%91-Linolenic_acid" title="Α-Linolenic acid">α-Linolenic acid</a>, with three double bonds, favors a hooked shape. The effect of this is that, in restricted environments, such as when fatty acids are part of a phospholipid in a lipid bilayer or triglycerides in lipid droplets, cis bonds limit the ability of fatty acids to be closely packed, and therefore can affect the melting temperature of the membrane or of the fat. Cis unsaturated fatty acids, however, increase cellular membrane fluidity, whereas trans unsaturated fatty acids do not.</dd> <dt><i>trans</i></dt> <dd>A <i>trans</i> configuration, by contrast, means that the adjacent two hydrogen atoms lie on <i>opposite</i> sides of the chain. As a result, they do not cause the chain to bend much, and their shape is similar to straight saturated fatty acids.</dd></dl> <p>In most naturally occurring unsaturated fatty acids, each double bond has three (<a href="/wiki/Omega-3_fatty_acid" title="Omega-3 fatty acid">n−3</a>), six (<a href="/wiki/Omega-6_fatty_acid" title="Omega-6 fatty acid">n−6</a>), or nine (<a href="/wiki/Omega-9_fatty_acid" title="Omega-9 fatty acid">n−9</a>) carbon atoms after it, and all double bonds have a cis configuration. Most fatty acids in the <i>trans</i> configuration (<a href="/wiki/Trans_fat" title="Trans fat">trans fats</a>) are not found in nature and are the result of human processing (e.g., <a href="/wiki/Hydrogenation" title="Hydrogenation">hydrogenation</a>). Some trans fatty acids also occur naturally in the milk and meat of <a href="/wiki/Ruminant" title="Ruminant">ruminants</a> (such as cattle and sheep). They are produced, by fermentation, in the rumen of these animals. They are also found in <a href="/wiki/Dairy_product" title="Dairy product">dairy products</a> from milk of ruminants, and may be also found in <a href="/wiki/Breast_milk" title="Breast milk">breast milk</a> of women who obtained them from their diet. </p><p>The geometric differences between the various types of unsaturated fatty acids, as well as between saturated and unsaturated fatty acids, play an important role in biological processes, and in the construction of biological structures (such as cell membranes). </p> <table class="wikitable"> <caption>Examples of Unsaturated Fatty Acids </caption> <tbody><tr> <th>Common name</th> <th>Chemical structure</th> <th>Δ<sup><i>x</i></sup><sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>b<span class="cite-bracket">]</span></a></sup></th> <th><i>C</i>:<i>D</i><sup id="cite_ref-c:d_10-1" class="reference"><a href="#cite_note-c:d-10"><span class="cite-bracket">[</span>a<span class="cite-bracket">]</span></a></sup></th> <th>IUPAC<sup id="cite_ref-IUPAClipid_12-0" class="reference"><a href="#cite_note-IUPAClipid-12"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup></th> <th><i>n</i>−<i>x</i><sup id="cite_ref-omega-x_13-0" class="reference"><a href="#cite_note-omega-x-13"><span class="cite-bracket">[</span>c<span class="cite-bracket">]</span></a></sup> </th></tr> <tr> <td colspan="6"><b>Omega−3:</b> </td></tr> <tr> <td><a href="/wiki/Eicosapentaenoic_acid" title="Eicosapentaenoic acid">Eicosapentaenoic acid</a> </td> <td>CH<sub>3</sub>CH<sub>2</sub><b>CH=CH</b>CH<sub>2</sub><b>CH=CH</b>CH<sub>2</sub><b>CH=CH</b>CH<sub>2</sub><b>CH=CH</b>CH<sub>2</sub><b>CH=CH</b>(CH<sub>2</sub>)<sub>3</sub>COOH </td> <td><i>cis</i>,<i>cis</i>,<i>cis</i>,<i>cis</i>,<i>cis</i>-Δ<sup>5</sup>,Δ<sup>8</sup>,Δ<sup>11</sup>,Δ<sup>14</sup>,Δ<sup>17</sup> </td> <td>20:5 </td> <td>20:5(5,8,11,14,17) </td> <td><a href="/wiki/Omega-3_fatty_acid" title="Omega-3 fatty acid"><i>n</i>−3</a> </td></tr> <tr> <td><a href="/wiki/%CE%91-Linolenic_acid" title="Α-Linolenic acid">α-Linolenic acid</a> </td> <td>CH<sub>3</sub>CH<sub>2</sub><b>CH=CH</b>CH<sub>2</sub><b>CH=CH</b>CH<sub>2</sub><b>CH=CH</b>(CH<sub>2</sub>)<sub>7</sub>COOH </td> <td><i>cis</i>,<i>cis</i>,<i>cis</i>-Δ<sup>9</sup>,Δ<sup>12</sup>,Δ<sup>15</sup> </td> <td>18:3 </td> <td>18:3(9,12,15) </td> <td><a href="/wiki/Omega-3_fatty_acid" title="Omega-3 fatty acid"><i>n</i>−3</a> </td></tr> <tr> <td><a href="/wiki/Docosahexaenoic_acid" title="Docosahexaenoic acid">Docosahexaenoic acid</a> </td> <td>CH<sub>3</sub>CH<sub>2</sub><b>CH=CH</b>CH<sub>2</sub><b>CH=CH</b>CH<sub>2</sub><b>CH=CH</b>CH<sub>2</sub><b>CH=CH</b>CH<sub>2</sub><b>CH=CH</b>CH<sub>2</sub><b>CH=CH</b>(CH<sub>2</sub>)<sub>2</sub>COOH </td> <td><i>cis</i>,<i>cis</i>,<i>cis</i>,<i>cis</i>,<i>cis</i>,<i>cis</i>-Δ<sup>4</sup>,Δ<sup>7</sup>,Δ<sup>10</sup>,Δ<sup>13</sup>,Δ<sup>16</sup>,Δ<sup>19</sup> </td> <td>22:6 </td> <td>22:6(4,7,10,13,16,19) </td> <td><a href="/wiki/Omega-3_fatty_acid" title="Omega-3 fatty acid"><i>n</i>−3</a> </td></tr> <tr> <td colspan="6"><b>Omega−6:</b> </td></tr> <tr> <td><a href="/wiki/Arachidonic_acid" title="Arachidonic acid">Arachidonic acid</a> </td> <td>CH<sub>3</sub>(CH<sub>2</sub>)<sub>4</sub><b>CH=CH</b>CH<sub>2</sub><b>CH=CH</b>CH<sub>2</sub><b>CH=CH</b>CH<sub>2</sub><b>CH=CH</b>(CH<sub>2</sub>)<sub>3</sub>COOH<sup><a rel="nofollow" class="external text" href="http://webbook.nist.gov/cgi/cbook.cgi?Name=Arachidonic+Acid&Units=SI">NIST</a></sup> </td> <td><i>cis</i>,<i>cis</i>,<i>cis</i>,<i>cis</i>-Δ<sup>5</sup>Δ<sup>8</sup>,Δ<sup>11</sup>,Δ<sup>14</sup> </td> <td>20:4 </td> <td>20:4(5,8,11,14) </td> <td><a href="/wiki/Omega-6_fatty_acid" title="Omega-6 fatty acid"><i>n</i>−6</a> </td></tr> <tr> <td><a href="/wiki/Linoleic_acid" title="Linoleic acid">Linoleic acid</a> </td> <td>CH<sub>3</sub>(CH<sub>2</sub>)<sub>4</sub><b>CH=CH</b>CH<sub>2</sub><b>CH=CH</b>(CH<sub>2</sub>)<sub>7</sub>COOH </td> <td><i>cis</i>,<i>cis</i>-Δ<sup>9</sup>,Δ<sup>12</sup> </td> <td>18:2 </td> <td>18:2(9,12) </td> <td><a href="/wiki/Omega-6_fatty_acid" title="Omega-6 fatty acid"><i>n</i>−6</a> </td></tr> <tr> <td><a href="/wiki/Linoelaidic_acid" class="mw-redirect" title="Linoelaidic acid">Linoelaidic acid</a> </td> <td>CH<sub>3</sub>(CH<sub>2</sub>)<sub>4</sub><b>CH=CH</b>CH<sub>2</sub><b>CH=CH</b>(CH<sub>2</sub>)<sub>7</sub>COOH </td> <td><i>trans</i>,<i>trans</i>-Δ<sup>9</sup>,Δ<sup>12</sup> </td> <td>18:2 </td> <td>18:2(9t,12t) </td> <td><a href="/wiki/Omega-6_fatty_acid" title="Omega-6 fatty acid"><i>n</i>−6</a> </td></tr> <tr> <td colspan="6"><b>Omega−9:</b> </td></tr> <tr> <td><a href="/wiki/Oleic_acid" title="Oleic acid">Oleic acid</a></td> <td>CH<sub>3</sub>(CH<sub>2</sub>)<sub>7</sub><b>CH=CH</b>(CH<sub>2</sub>)<sub>7</sub>COOH</td> <td><i>cis</i>-Δ<sup>9</sup></td> <td>18:1</td> <td>18:1(9)</td> <td><a href="/wiki/Omega-9_fatty_acid" title="Omega-9 fatty acid"><i>n</i>−9</a> </td></tr> <tr> <td><a href="/wiki/Elaidic_acid" title="Elaidic acid">Elaidic acid</a></td> <td>CH<sub>3</sub>(CH<sub>2</sub>)<sub>7</sub><b>CH=CH</b>(CH<sub>2</sub>)<sub>7</sub>COOH</td> <td><i>trans</i>-Δ<sup>9</sup></td> <td>18:1</td> <td>18:1(9t)</td> <td><a href="/wiki/Omega-9_fatty_acid" title="Omega-9 fatty acid"><i>n</i>−9</a> </td></tr> <tr> <td><a href="/wiki/Erucic_acid" title="Erucic acid">Erucic acid</a></td> <td>CH<sub>3</sub>(CH<sub>2</sub>)<sub>7</sub><b>CH=CH</b>(CH<sub>2</sub>)<sub>11</sub>COOH</td> <td><i>cis</i>-Δ<sup>13</sup></td> <td>22:1</td> <td>22:1(13)</td> <td><a href="/wiki/Omega-9_fatty_acid" title="Omega-9 fatty acid"><i>n</i>−9</a> </td></tr> <tr> <td colspan="6"><b>Omega−5, 7, and 10:</b> </td></tr> <tr> <td><a href="/wiki/Myristoleic_acid" title="Myristoleic acid">Myristoleic acid</a></td> <td>CH<sub>3</sub>(CH<sub>2</sub>)<sub>3</sub><b>CH=CH</b>(CH<sub>2</sub>)<sub>7</sub>COOH</td> <td><i>cis</i>-Δ<sup>9</sup></td> <td>14:1</td> <td>14:1(9)</td> <td><i>n</i>−5 </td></tr> <tr> <td><a href="/wiki/Palmitoleic_acid" title="Palmitoleic acid">Palmitoleic acid</a></td> <td>CH<sub>3</sub>(CH<sub>2</sub>)<sub>5</sub><b>CH=CH</b>(CH<sub>2</sub>)<sub>7</sub>COOH</td> <td><i>cis</i>-Δ<sup>9</sup></td> <td>16:1</td> <td>16:1(9)</td> <td><i>n</i>−7 </td></tr> <tr> <td><a href="/wiki/Vaccenic_acid" title="Vaccenic acid">Vaccenic acid</a> </td> <td>CH<sub>3</sub>(CH<sub>2</sub>)<sub>5</sub><b>CH=CH</b>(CH<sub>2</sub>)<sub>9</sub>COOH </td> <td><i>trans</i>-Δ<sup>11</sup> </td> <td>18:1 </td> <td>18:1(11t) </td> <td><i>n</i>−7 </td></tr> <tr> <td><a href="/wiki/Sapienic_acid" title="Sapienic acid">Sapienic acid</a></td> <td>CH<sub>3</sub>(CH<sub>2</sub>)<sub>8</sub><b>CH=CH</b>(CH<sub>2</sub>)<sub>4</sub>COOH</td> <td><i>cis</i>-Δ<sup>6</sup></td> <td>16:1</td> <td>16:1(6)</td> <td><i>n</i>−10 </td></tr></tbody></table> <div class="mw-heading mw-heading3"><h3 id="Even-_vs_odd-chained_fatty_acids">Even- vs odd-chained fatty acids</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fatty_acid&action=edit&section=6" title="Edit section: Even- vs odd-chained fatty acids"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Most fatty acids are even-chained, e.g. stearic (C18) and oleic (C18), meaning they are composed of an even number of carbon atoms. Some fatty acids have odd numbers of carbon atoms; they are referred to as odd-chained fatty acids (OCFA). The most common OCFA are the saturated C15 and C17 derivatives, <a href="/wiki/Pentadecanoic_acid" class="mw-redirect" title="Pentadecanoic acid">pentadecanoic acid</a> and <a href="/wiki/Heptadecanoic_acid" class="mw-redirect" title="Heptadecanoic acid">heptadecanoic acid</a> respectively, which are found in dairy products.<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> On a molecular level, OCFAs are biosynthesized and metabolized slightly differently from the even-chained relatives. </p> <div class="mw-heading mw-heading3"><h3 id="Branching">Branching</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fatty_acid&action=edit&section=7" title="Edit section: Branching"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Most common fatty acids are <a href="/wiki/Straight-chain_compound" class="mw-redirect" title="Straight-chain compound">straight-chain compounds</a>, with no additional carbon atoms bonded as <a href="/wiki/Side_group" class="mw-redirect" title="Side group">side groups</a> to the main hydrocarbon chain. <a href="/wiki/Branched-chain_fatty_acid" title="Branched-chain fatty acid">Branched-chain fatty acids</a> contain one or more <a href="/wiki/Methyl_groups" class="mw-redirect" title="Methyl groups">methyl groups</a> bonded to the hydrocarbon chain. </p> <div class="mw-heading mw-heading2"><h2 id="Nomenclature">Nomenclature</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fatty_acid&action=edit&section=8" title="Edit section: Nomenclature"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Carbon_atom_numbering">Carbon atom numbering</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fatty_acid&action=edit&section=9" title="Edit section: Carbon atom numbering"><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/Essential_fatty_acid#Nomenclature_and_terminology" title="Essential fatty acid">Essential fatty acid § Nomenclature and terminology</a></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Fatty_acid_carbon_numbering.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b7/Fatty_acid_carbon_numbering.svg/440px-Fatty_acid_carbon_numbering.svg.png" decoding="async" width="440" height="93" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b7/Fatty_acid_carbon_numbering.svg/660px-Fatty_acid_carbon_numbering.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b7/Fatty_acid_carbon_numbering.svg/880px-Fatty_acid_carbon_numbering.svg.png 2x" data-file-width="1276" data-file-height="270" /></a><figcaption>Numbering of carbon atoms. The systematic (IUPAC) C-<i>x</i> numbers are in blue. The omega-minus "ω−<i>x</i>" labels are in red. The Greek letter labels are in green.<sup id="cite_ref-note.omega_16-0" class="reference"><a href="#cite_note-note.omega-16"><span class="cite-bracket">[</span>d<span class="cite-bracket">]</span></a></sup> Note that <a href="#Unsaturated_fatty_acids">unsaturated fatty acids</a> with a <i>cis</i> configuration are actually "kinked" rather than straight as shown here.</figcaption></figure> <p>Most naturally occurring fatty acids have an <a href="/wiki/Branched_chain_fatty_acids" class="mw-redirect" title="Branched chain fatty acids">unbranched chain</a> of carbon atoms, with a <a href="/wiki/Carboxyl_group" class="mw-redirect" title="Carboxyl group">carboxyl group</a> (–COOH) at one end, and a <a href="/wiki/Methyl_group" title="Methyl group">methyl group</a> (–CH3) at the other end. </p><p>The position of each carbon atom in the backbone of a fatty acid is usually indicated by counting from 1 at the −COOH end. Carbon number <i>x</i> is often abbreviated C-<i>x</i> (or sometimes C<i>x</i>), with <i>x</i> = 1, 2, 3, etc. This is the numbering scheme recommended by the <a href="/wiki/IUPAC" class="mw-redirect" title="IUPAC">IUPAC</a>. </p><p>Another convention uses letters of the <a href="/wiki/Greek_alphabet" title="Greek alphabet">Greek alphabet</a> in sequence, starting with the first carbon <i>after</i> the carboxyl group. Thus carbon α (<a href="/wiki/Alpha" title="Alpha">alpha</a>) is C-2, carbon β (<a href="/wiki/Beta" title="Beta">beta</a>) is C-3, and so forth. </p><p>Although fatty acids can be of diverse lengths, in this second convention the last carbon in the chain is always labelled as ω (<a href="/wiki/Omega" title="Omega">omega</a>), which is the last letter in the Greek alphabet. A third numbering convention counts the carbons from that end, using the labels "ω", "ω−1", "ω−2". Alternatively, the label "ω−<i>x</i>" is written "n−<i>x</i>", where the "n" is meant to represent the number of carbons in the chain.<sup id="cite_ref-note.omega_16-1" class="reference"><a href="#cite_note-note.omega-16"><span class="cite-bracket">[</span>d<span class="cite-bracket">]</span></a></sup> </p><p>In either numbering scheme, the position of a <a href="/wiki/Double_bond" title="Double bond">double bond</a> in a fatty acid chain is always specified by giving the label of the carbon closest to the <b>carboxyl</b> end.<sup id="cite_ref-note.omega_16-2" class="reference"><a href="#cite_note-note.omega-16"><span class="cite-bracket">[</span>d<span class="cite-bracket">]</span></a></sup> Thus, in an 18 carbon fatty acid, a double bond between C-12 (or ω−6) and C-13 (or ω−5) is said to be "at" position C-12 or ω−6. The IUPAC naming of the acid, such as "octadec-12-enoic acid" (or the more pronounceable variant "12-octadecanoic acid") is always based on the "C" numbering. </p><p>The notation Δ<sup><i>x</i>,<i>y</i>,...</sup> is traditionally used to specify a fatty acid with double bonds at positions <i>x</i>,<i>y</i>,.... (The capital Greek letter "Δ" (<a href="/wiki/Delta_(letter)" title="Delta (letter)">delta</a>) corresponds to <a href="/wiki/Latin_alphabet" title="Latin alphabet">Roman</a> "D", for <b>D</b>ouble bond). Thus, for example, the 20-carbon <a href="/wiki/Arachidonic_acid" title="Arachidonic acid">arachidonic acid</a> is Δ<sup>5,8,11,14</sup>, meaning that it has double bonds between carbons 5 and 6, 8 and 9, 11 and 12, and 14 and 15. </p><p>In the context of human diet and fat metabolism, unsaturated fatty acids are often classified by the position of the double bond closest between to the ω carbon (only), even in the case of <a href="/wiki/Polyunsaturated_fatty_acid" class="mw-redirect" title="Polyunsaturated fatty acid">multiple double bonds</a> such as the <a href="/wiki/Essential_fatty_acid" title="Essential fatty acid">essential fatty acids</a>. Thus <a href="/wiki/Linoleic_acid" title="Linoleic acid">linoleic acid</a> (18 carbons, Δ<sup>9,12</sup>), <a href="/wiki/Gamma-Linolenic_acid" class="mw-redirect" title="Gamma-Linolenic acid">γ-linole<b>n</b>ic acid</a> (18-carbon, Δ<sup>6,9,12</sup>), and arachidonic acid (20-carbon, Δ<sup>5,8,11,14</sup>) are all classified as "ω−6" fatty acids; meaning that their <a href="/wiki/Condensed_structural_formula" class="mw-redirect" title="Condensed structural formula">formula</a> ends with –CH=CH–<span class="chemf nowrap">CH<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2</sub></span></span></span>–<span class="chemf nowrap">CH<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2</sub></span></span></span>–<span class="chemf nowrap">CH<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2</sub></span></span></span>–<span class="chemf nowrap">CH<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2</sub></span></span></span>–<span class="chemf nowrap">CH<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">3</sub></span></span></span>. </p><p>Fatty acids with an <a href="/wiki/Odd_number" class="mw-redirect" title="Odd number">odd number</a> of carbon atoms are called <a href="/wiki/Odd-chain_fatty_acid" title="Odd-chain fatty acid">odd-chain fatty acids</a>, whereas the rest are even-chain fatty acids. The difference is <a href="/wiki/Gluconeogenesis#Precursors" title="Gluconeogenesis">relevant to gluconeogenesis</a>. </p> <div class="mw-heading mw-heading3"><h3 id="Naming_of_fatty_acids">Naming of fatty acids</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fatty_acid&action=edit&section=10" title="Edit section: Naming of fatty acids"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The following table describes the most common systems of naming fatty acids. </p> <div style="clear:both;" class=""></div> <table class="wikitable"> <tbody><tr> <th>Nomenclature </th> <th>Examples </th> <th>Explanation </th></tr> <tr> <th>Trivial </th> <td><a href="/wiki/Palmitoleic_acid" title="Palmitoleic acid">Palmitoleic acid</a> </td> <td><b><a href="/wiki/Trivial_name" title="Trivial name">Trivial names</a></b> (or <b>common names</b>) are non-systematic historical names, which are the most frequent naming system used in literature. Most common fatty acids have trivial names in addition to their <i>systematic names</i> (see below). These names frequently do not follow any pattern, but they are concise and often unambiguous. </td></tr> <tr> <th>Systematic </th> <td><a href="/wiki/Oleic_acid" title="Oleic acid">cis-9-octadec-9-enoic acid</a><br /><a href="/wiki/Oleic_acid" title="Oleic acid">(9<i>Z</i>)-octadec-9-enoic acid</a> </td> <td><b><a href="/wiki/Systematic_name" title="Systematic name">Systematic names</a></b> (or <b><a href="/wiki/International_Union_of_Pure_and_Applied_Chemistry" title="International Union of Pure and Applied Chemistry">IUPAC</a> names</b>) derive from the standard <i><a href="/wiki/IUPAC_nomenclature_of_organic_chemistry" title="IUPAC nomenclature of organic chemistry">IUPAC Rules for the Nomenclature of Organic Chemistry</a></i>, published in 1979,<sup id="cite_ref-nomenclature-1979_17-0" class="reference"><a href="#cite_note-nomenclature-1979-17"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> along with a recommendation published specifically for lipids in 1977.<sup id="cite_ref-nomenclature-1977_18-0" class="reference"><a href="#cite_note-nomenclature-1977-18"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> <a href="#Numbering_of_the_carbon_atoms_in_a_fatty_acid">Carbon atom numbering</a> begins from the <a href="/wiki/Carboxylic_group" class="mw-redirect" title="Carboxylic group">carboxylic</a> end of the molecule backbone. <a href="/wiki/Double_bond" title="Double bond">Double bonds</a> are labelled with <a href="/wiki/Cis-trans_isomerism" class="mw-redirect" title="Cis-trans isomerism"><i>cis</i>-/<i>trans</i>-</a> notation or <i><a href="/wiki/E-Z_notation" class="mw-redirect" title="E-Z notation">E</a></i>-/<i><a href="/wiki/E-Z_notation" class="mw-redirect" title="E-Z notation">Z</a></i>- notation, where appropriate. This notation is generally more verbose than common nomenclature, but has the advantage of being more technically clear and descriptive. </td></tr> <tr> <th>Δ<sup><i>x</i></sup> </th> <td><a href="/wiki/Linoleic_acid" title="Linoleic acid"><i>cis</i>-Δ<sup>9</sup>, <i>cis</i>-Δ<sup>12</sup> octadecadienoic acid</a> </td> <td>In <b>Δ<sup><i>x</i></sup></b> (or <b>delta-<i>x</i></b>) <b>nomenclature</b>, each double bond is indicated by Δ<sup><i>x</i></sup>, where the double bond begins at the <i>x</i>th carbon–carbon bond, <a href="#Numbering_of_the_carbon_atoms_in_a_fatty_acid">counting</a> from <a href="/wiki/Carboxylic_group" class="mw-redirect" title="Carboxylic group">carboxylic</a> end of the molecule backbone. Each double bond is preceded by a <i><a href="/wiki/Cis-trans_isomerism" class="mw-redirect" title="Cis-trans isomerism">cis</a></i>- or <i><a href="/wiki/Cis-trans_isomerism" class="mw-redirect" title="Cis-trans isomerism">trans</a></i>- prefix, indicating the configuration of the molecule around the bond. For example, <a href="/wiki/Linoleic_acid" title="Linoleic acid">linoleic acid</a> is designated "<i>cis</i>-Δ<sup>9</sup>, <i>cis</i>-Δ<sup>12</sup> octadecadienoic acid". This nomenclature has the advantage of being less verbose than systematic nomenclature, but is no more technically clear or descriptive.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="citation needed for this verbose delta notation, sometimes in chemical it's seen simpler notation with single delta, locants in superscript comma-separated, for various types of unsaturated natural organic compounds (September 2018)">citation needed</span></a></i>]</sup> </td></tr> <tr> <th><i>n</i>−<i>x</i> <br />(or ω−<i>x</i>) </th> <td><a href="/wiki/Omega-3_fatty_acid" title="Omega-3 fatty acid"><i>n</i>−3</a><br />(or <a href="/wiki/Omega-3_fatty_acid" title="Omega-3 fatty acid">ω−3</a>) </td> <td><b><i>n</i>−<i>x</i></b> (<b><i>n</i> minus <i>x</i></b>; also <b>ω−<i>x</i></b> or <b>omega−<i>x</i></b>) <b>nomenclature</b> both provides names for individual compounds and classifies them by their likely biosynthetic properties in animals. A double bond is located on the <i>x</i><sup>th</sup> carbon–carbon bond, <a href="#Numbering_of_the_carbon_atoms_in_a_fatty_acid">counting</a> from the <a href="/wiki/Methyl_group" title="Methyl group">methyl</a> end of the molecule backbone. For example, <a href="/wiki/%CE%91-Linolenic_acid" title="Α-Linolenic acid">α-linolenic acid</a> is classified as a <a href="/wiki/Omega-3_fatty_acid" title="Omega-3 fatty acid"><i>n</i>−3</a> or <a href="/wiki/Omega-3" class="mw-redirect" title="Omega-3">omega−3</a> fatty acid, and so it is likely to share a biosynthetic pathway with other compounds of this type. The ω−<i>x</i>, omega−<i>x</i>, or "omega" notation is common in popular nutritional literature, but <a href="/wiki/IUPAC_nomenclature" class="mw-redirect" title="IUPAC nomenclature">IUPAC</a> has deprecated it in favor of <i>n</i>−<i>x</i> notation in technical documents.<sup id="cite_ref-nomenclature-1979_17-1" class="reference"><a href="#cite_note-nomenclature-1979-17"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> The most commonly researched fatty acid biosynthetic pathways are <a href="/wiki/Omega-3_fatty_acid" title="Omega-3 fatty acid"><i>n</i>−3</a> and <a href="/wiki/Omega-6_fatty_acid" title="Omega-6 fatty acid"><i>n</i>−6</a>. </td></tr> <tr> <th>Lipid numbers </th> <td>18:3<br /><a href="/wiki/%CE%91-Linolenic_acid" title="Α-Linolenic acid">18:3n3</a><br /><a href="/wiki/%CE%91-Linolenic_acid" title="Α-Linolenic acid">18:3, <i>cis</i>,<i>cis</i>,<i>cis</i>-Δ<sup>9</sup>,Δ<sup>12</sup>,Δ<sup>15</sup></a><br /><a href="/wiki/%CE%91-Linolenic_acid" title="Α-Linolenic acid">18:3(9,12,15)</a> </td> <td><b>Lipid numbers</b> take the form <i>C</i>:<i>D</i>,<sup id="cite_ref-c:d_10-2" class="reference"><a href="#cite_note-c:d-10"><span class="cite-bracket">[</span>a<span class="cite-bracket">]</span></a></sup> where <i>C</i> is the number of carbon atoms in the fatty acid and <i>D</i> is the number of double bonds in the fatty acid. If D is more than one, the double bonds are assumed to be interrupted by <a href="/wiki/Methylene_bridge" title="Methylene bridge"><span class="chemf nowrap">CH<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2</sub></span></span></span> units</a>, <i>i.e.</i>, at intervals of 3 carbon atoms along the chain. For instance, <a href="/wiki/%CE%91-Linolenic_acid" title="Α-Linolenic acid">α-linolenic acid</a> is an 18:3 fatty acid and its three double bonds are located at positions Δ<sup>9</sup>, Δ<sup>12</sup>, and Δ<sup>15</sup>. This notation can be ambiguous, as some different fatty acids can have the same <i>C</i>:<i>D</i> numbers. Consequently, when ambiguity exists this notation is usually paired with either a Δ<sup><i>x</i></sup> or <i>n</i>−<i>x</i> term.<sup id="cite_ref-nomenclature-1979_17-2" class="reference"><a href="#cite_note-nomenclature-1979-17"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> For instance, although <a href="/wiki/%CE%91-Linolenic_acid" title="Α-Linolenic acid">α-linolenic acid</a> and <a href="/wiki/Gamma-Linolenic_acid" class="mw-redirect" title="Gamma-Linolenic acid">γ-linolenic acid</a> are both 18:3, they may be unambiguously described as 18:3n3 and 18:3n6 fatty acids, respectively. For the same purpose, IUPAC recommends using a list of double bond positions in parentheses, appended to the C:D notation.<sup id="cite_ref-IUPAClipid_12-1" class="reference"><a href="#cite_note-IUPAClipid-12"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> For instance, IUPAC recommended notations for α- and γ-linolenic acid are 18:3(9,12,15) and 18:3(6,9,12), respectively. </td></tr></tbody></table> <div class="mw-heading mw-heading3"><h3 id="Free_fatty_acids">Free fatty acids</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fatty_acid&action=edit&section=11" title="Edit section: Free fatty acids"><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/Deep_frying#Oil_deterioration_and_chemical_changes" title="Deep frying">Deep frying § Oil deterioration and chemical changes</a></div> <p>When <a href="/wiki/Circulatory_system" title="Circulatory system">circulating</a> in the <a href="/wiki/Blood_plasma" title="Blood plasma">plasma</a> (plasma fatty acids), not in their <a href="/wiki/Ester" title="Ester">ester</a>, fatty acids are known as non-esterified fatty acids (NEFAs) or free fatty acids (FFAs). FFAs are always bound to a <a href="/wiki/Transport_protein" title="Transport protein">transport protein</a>, such as <a href="/wiki/Albumin" title="Albumin">albumin</a>.<sup id="cite_ref-Dorlands_19-0" class="reference"><a href="#cite_note-Dorlands-19"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> </p><p>FFAs also form from <a href="/wiki/Triglyceride" title="Triglyceride">triglyceride</a> food oils and fats by hydrolysis, contributing to the characteristic <a href="/wiki/Rancidification" title="Rancidification">rancid</a> odor.<sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> An analogous process happens in <a href="/wiki/Biodiesel" title="Biodiesel">biodiesel</a> with risk of part corrosion. </p> <div class="mw-heading mw-heading2"><h2 id="Production">Production</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fatty_acid&action=edit&section=12" title="Edit section: Production"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Industrial">Industrial</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fatty_acid&action=edit&section=13" title="Edit section: Industrial"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Fatty acids are usually produced industrially by the <a href="/wiki/Hydrolysis" title="Hydrolysis">hydrolysis</a> of <a href="/wiki/Triglyceride" title="Triglyceride">triglycerides</a>, with the removal of <a href="/wiki/Glycerol" title="Glycerol">glycerol</a> (see <a href="/wiki/Oleochemical" class="mw-redirect" title="Oleochemical">oleochemicals</a>). <a href="/wiki/Phospholipid" title="Phospholipid">Phospholipids</a> represent another source. Some fatty acids are produced synthetically by <a href="/wiki/Carbonylation" title="Carbonylation">hydrocarboxylation</a> of alkenes.<sup id="cite_ref-Ullmann_Fatty_Acids_21-0" class="reference"><a href="#cite_note-Ullmann_Fatty_Acids-21"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="By_animals">By animals</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fatty_acid&action=edit&section=14" title="Edit section: By animals"><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/Fatty_acid_synthesis" title="Fatty acid synthesis">Fatty acid synthesis</a></div> <p>In animals, fatty acids are formed from carbohydrates predominantly in the <a href="/wiki/Liver" title="Liver">liver</a>, <a href="/wiki/Adipose_tissue" title="Adipose tissue">adipose tissue</a>, and the <a href="/wiki/Mammary_gland" title="Mammary gland">mammary glands</a> during lactation.<sup id="cite_ref-stryer_22-0" class="reference"><a href="#cite_note-stryer-22"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> </p><p>Carbohydrates are converted into <a href="/wiki/Pyruvic_acid" title="Pyruvic acid">pyruvate</a> by <a href="/wiki/Glycolysis" title="Glycolysis">glycolysis</a> as the first important step in the conversion of carbohydrates into fatty acids.<sup id="cite_ref-stryer_22-1" class="reference"><a href="#cite_note-stryer-22"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> Pyruvate is then decarboxylated to form <a href="/wiki/Acetyl-CoA" title="Acetyl-CoA">acetyl-CoA</a> in the <a href="/wiki/Mitochondrion" title="Mitochondrion">mitochondrion</a>. However, this acetyl CoA needs to be transported into <a href="/wiki/Cytosol" title="Cytosol">cytosol</a> where the synthesis of fatty acids occurs. This cannot occur directly. To obtain cytosolic acetyl-CoA, <a href="/wiki/Citric_acid" title="Citric acid">citrate</a> (produced by the condensation of acetyl-CoA with <a href="/wiki/Oxaloacetic_acid" title="Oxaloacetic acid">oxaloacetate</a>) is removed from the <a href="/wiki/Citric_acid_cycle" title="Citric acid cycle">citric acid cycle</a> and carried across the inner mitochondrial membrane into the cytosol.<sup id="cite_ref-stryer_22-2" class="reference"><a href="#cite_note-stryer-22"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> There it is cleaved by <a href="/wiki/ATP_citrate_lyase" class="mw-redirect" title="ATP citrate lyase">ATP citrate lyase</a> into acetyl-CoA and oxaloacetate. The oxaloacetate is returned to the mitochondrion as <a href="/wiki/Malate" class="mw-redirect" title="Malate">malate</a>.<sup id="cite_ref-ferre_23-0" class="reference"><a href="#cite_note-ferre-23"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> The cytosolic acetyl-CoA is carboxylated by <a href="/wiki/Acetyl-CoA_carboxylase" title="Acetyl-CoA carboxylase">acetyl-CoA carboxylase</a> into <a href="/wiki/Malonyl-CoA" title="Malonyl-CoA">malonyl-CoA</a>, the first committed step in the synthesis of fatty acids.<sup id="cite_ref-ferre_23-1" class="reference"><a href="#cite_note-ferre-23"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Voet_24-0" class="reference"><a href="#cite_note-Voet-24"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> </p><p>Malonyl-CoA is then involved in a repeating series of reactions that lengthens the growing fatty acid chain by two carbons at a time. Almost all natural fatty acids, therefore, have even numbers of carbon atoms. When synthesis is complete the free fatty acids are nearly always combined with glycerol (three fatty acids to one glycerol molecule) to form <a href="/wiki/Triglyceride" title="Triglyceride">triglycerides</a>, the main storage form of fatty acids, and thus of energy in animals. However, fatty acids are also important components of the <a href="/wiki/Phospholipid" title="Phospholipid">phospholipids</a> that form the <a href="/wiki/Phospholipid_bilayers" class="mw-redirect" title="Phospholipid bilayers">phospholipid bilayers</a> out of which all the membranes of the cell are constructed (the <a href="/wiki/Cell_wall" title="Cell wall">cell wall</a>, and the membranes that enclose all the <a href="/wiki/Organelle" title="Organelle">organelles</a> within the cells, such as the <a href="/wiki/Cell_nucleus" title="Cell nucleus">nucleus</a>, the <a href="/wiki/Mitochondrion" title="Mitochondrion">mitochondria</a>, <a href="/wiki/Endoplasmic_reticulum" title="Endoplasmic reticulum">endoplasmic reticulum</a>, and the <a href="/wiki/Golgi_apparatus" title="Golgi apparatus">Golgi apparatus</a>).<sup id="cite_ref-stryer_22-3" class="reference"><a href="#cite_note-stryer-22"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> </p><p>The "uncombined fatty acids" or "free fatty acids" found in the circulation of animals come from the breakdown (or <a href="/wiki/Lipolysis" title="Lipolysis">lipolysis</a>) of stored triglycerides.<sup id="cite_ref-stryer_22-4" class="reference"><a href="#cite_note-stryer-22"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-25" class="reference"><a href="#cite_note-25"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> Because they are insoluble in water, these fatty acids are transported bound to plasma <a href="/wiki/Albumin" title="Albumin">albumin</a>. The levels of "free fatty acids" in the blood are limited by the availability of albumin binding sites. They can be taken up from the blood by all cells that have mitochondria (with the exception of the cells of the <a href="/wiki/Central_nervous_system" title="Central nervous system">central nervous system</a>). Fatty acids can only be broken down in mitochondria, by means of <a href="/wiki/Beta-oxidation" class="mw-redirect" title="Beta-oxidation">beta-oxidation</a> followed by further combustion in the <a href="/wiki/Citric_acid_cycle" title="Citric acid cycle">citric acid cycle</a> to CO<sub>2</sub> and water. Cells in the central nervous system, although they possess mitochondria, cannot take free fatty acids up from the blood, as the <a href="/wiki/Blood%E2%80%93brain_barrier" title="Blood–brain barrier">blood–brain barrier</a> is impervious to most free fatty acids,<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (June 2016)">citation needed</span></a></i>]</sup> excluding <a href="/wiki/Short-chain_fatty_acid" title="Short-chain fatty acid">short-chain fatty acids</a> and <a href="/wiki/Medium-chain_fatty_acid" class="mw-redirect" title="Medium-chain fatty acid">medium-chain fatty acids</a>.<sup id="cite_ref-SCFA_MCT-mediated_BBB_passage_-_2005_review_26-0" class="reference"><a href="#cite_note-SCFA_MCT-mediated_BBB_passage_-_2005_review-26"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-SCFA_MCT-mediated_BBB_passage_-_2014_review_27-0" class="reference"><a href="#cite_note-SCFA_MCT-mediated_BBB_passage_-_2014_review-27"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> These cells have to manufacture their own fatty acids from carbohydrates, as described above, in order to produce and maintain the phospholipids of their cell membranes, and those of their organelles.<sup id="cite_ref-stryer_22-5" class="reference"><a href="#cite_note-stryer-22"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Variation_between_animal_species">Variation between animal species</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fatty_acid&action=edit&section=15" title="Edit section: Variation between animal species"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Studies on the <a href="/wiki/Cell_membrane" title="Cell membrane">cell membranes</a> of <a href="/wiki/Mammal" title="Mammal">mammals</a> and <a href="/wiki/Reptile" title="Reptile">reptiles</a> discovered that mammalian cell membranes are composed of a higher proportion of polyunsaturated fatty acids (<a href="/wiki/Docosahexaenoic_acid" title="Docosahexaenoic acid">DHA</a>, <a href="/wiki/Omega-3_fatty_acid" title="Omega-3 fatty acid">omega−3 fatty acid</a>) than <a href="/wiki/Reptile" title="Reptile">reptiles</a>.<sup id="cite_ref-hulb1999_28-0" class="reference"><a href="#cite_note-hulb1999-28"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> Studies on bird fatty acid composition have noted similar proportions to mammals but with 1/3rd less omega−3 fatty acids as compared to <a href="/wiki/Omega-6_fatty_acid" title="Omega-6 fatty acid">omega−6</a> for a given body size.<sup id="cite_ref-hulb2002_29-0" class="reference"><a href="#cite_note-hulb2002-29"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> This fatty acid composition results in a more fluid cell membrane but also one that is permeable to various ions (<style data-mw-deduplicate="TemplateStyles:r1123817410">.mw-parser-output .template-chem2-su{display:inline-block;font-size:80%;line-height:1;vertical-align:-0.35em}.mw-parser-output .template-chem2-su>span{display:block;text-align:left}.mw-parser-output sub.template-chem2-sub{font-size:80%;vertical-align:-0.35em}.mw-parser-output sup.template-chem2-sup{font-size:80%;vertical-align:0.65em}</style><span class="chemf nowrap">H<sup class="template-chem2-sup">+</sup></span> & <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Na<sup class="template-chem2-sup">+</sup></span>), resulting in cell membranes that are more costly to maintain. This maintenance cost has been argued to be one of the key causes for the high metabolic rates and concomitant <a href="/wiki/Warm-blooded" title="Warm-blooded">warm-bloodedness</a> of mammals and birds.<sup id="cite_ref-hulb1999_28-1" class="reference"><a href="#cite_note-hulb1999-28"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> However polyunsaturation of cell membranes may also occur in response to chronic cold temperatures as well. In <a href="/wiki/Fish" title="Fish">fish</a> increasingly cold environments lead to increasingly high cell membrane content of both monounsaturated and polyunsaturated fatty acids, to maintain greater membrane fluidity (and functionality) at the lower <a href="/wiki/Temperature" title="Temperature">temperatures</a>.<sup id="cite_ref-hulb2003xa_30-0" class="reference"><a href="#cite_note-hulb2003xa-30"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-rayn1991_31-0" class="reference"><a href="#cite_note-rayn1991-31"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Fatty_acids_in_dietary_fats">Fatty acids in dietary fats</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fatty_acid&action=edit&section=16" title="Edit section: Fatty acids in dietary fats"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The following table gives the fatty acid, <a href="/wiki/Vitamin_E" title="Vitamin E">vitamin E</a> and <a href="/wiki/Cholesterol" title="Cholesterol">cholesterol</a> composition of some common dietary fats.<sup id="cite_ref-32" class="reference"><a href="#cite_note-32"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-33" class="reference"><a href="#cite_note-33"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> </p> <table class="wikitable"> <caption> </caption> <tbody><tr> <th></th> <th>Saturated</th> <th>Monounsaturated</th> <th>Polyunsaturated</th> <th>Cholesterol</th> <th>Vitamin E </th></tr> <tr> <td></td> <td align="center">g/100g</td> <td align="center">g/100g</td> <td align="center">g/100g</td> <td align="center">mg/100g</td> <td align="center">mg/100g </td></tr> <tr> <td colspan="6"><i><b>Animal fats</b></i> </td></tr> <tr> <td><a href="/wiki/Duck_fat" class="mw-redirect" title="Duck fat">Duck fat</a><sup id="cite_ref-usda_34-0" class="reference"><a href="#cite_note-usda-34"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup></td> <td align="right">33.2</td> <td align="right">49.3</td> <td align="right">12.9</td> <td align="right">100</td> <td align="right">2.70 </td></tr> <tr> <td><a href="/wiki/Lard" title="Lard">Lard</a><sup id="cite_ref-usda_34-1" class="reference"><a href="#cite_note-usda-34"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup></td> <td align="right">40.8</td> <td align="right">43.8</td> <td align="right">9.6</td> <td align="right">93</td> <td align="right">0.60 </td></tr> <tr> <td><a href="/wiki/Tallow" title="Tallow">Tallow</a><sup id="cite_ref-usda_34-2" class="reference"><a href="#cite_note-usda-34"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup></td> <td align="right">49.8</td> <td align="right">41.8</td> <td align="right">4.0</td> <td align="right">109</td> <td align="right">2.70 </td></tr> <tr> <td><a href="/wiki/Butter" title="Butter">Butter</a></td> <td align="right">54.0</td> <td align="right">19.8</td> <td align="right">2.6</td> <td align="right">230</td> <td align="right">2.00 </td></tr> <tr> <td colspan="6"><i><b>Vegetable fats</b></i> </td></tr> <tr> <td><a href="/wiki/Coconut_oil" title="Coconut oil">Coconut oil</a></td> <td align="right">85.2</td> <td align="right">6.6</td> <td align="right">1.7</td> <td align="right">0</td> <td align="right">.66 </td></tr> <tr> <td><a href="/wiki/Cocoa_butter" title="Cocoa butter">Cocoa butter</a></td> <td align="right">60.0</td> <td align="right">32.9</td> <td align="right">3.0</td> <td align="right">0</td> <td align="right">1.8 </td></tr> <tr> <td><a href="/wiki/Palm_kernel_oil" title="Palm kernel oil">Palm kernel oil</a></td> <td align="right">81.5</td> <td align="right">11.4</td> <td align="right">1.6</td> <td align="right">0</td> <td align="right">3.80 </td></tr> <tr> <td><a href="/wiki/Palm_oil" title="Palm oil">Palm oil</a></td> <td align="right">45.3</td> <td align="right">41.6</td> <td align="right">8.3</td> <td align="right">0</td> <td align="right">33.12 </td></tr> <tr> <td><a href="/wiki/Cottonseed_oil" title="Cottonseed oil">Cottonseed oil</a></td> <td align="right">25.5</td> <td align="right">21.3</td> <td align="right">48.1</td> <td align="right">0</td> <td align="right">42.77 </td></tr> <tr> <td><a href="/wiki/Wheat_germ_oil" title="Wheat germ oil">Wheat germ oil</a></td> <td align="right">18.8</td> <td align="right">15.9</td> <td align="right">60.7</td> <td align="right">0</td> <td align="right">136.65 </td></tr> <tr> <td><a href="/wiki/Soybean_oil" title="Soybean oil">Soybean oil</a></td> <td align="right">14.5</td> <td align="right">23.2</td> <td align="right">56.5</td> <td align="right">0</td> <td align="right">16.29 </td></tr> <tr> <td><a href="/wiki/Olive_oil" title="Olive oil">Olive oil</a></td> <td align="right">14.0</td> <td align="right">69.7</td> <td align="right">11.2</td> <td align="right">0</td> <td align="right">5.10 </td></tr> <tr> <td><a href="/wiki/Corn_oil" title="Corn oil">Corn oil</a></td> <td align="right">12.7</td> <td align="right">24.7</td> <td align="right">57.8</td> <td align="right">0</td> <td align="right">17.24 </td></tr> <tr> <td><a href="/wiki/Sunflower_oil" title="Sunflower oil">Sunflower oil</a></td> <td align="right">11.9</td> <td align="right">20.2</td> <td align="right">63.0</td> <td align="right">0</td> <td align="right">49.00 </td></tr> <tr> <td><a href="/wiki/Safflower_oil" class="mw-redirect" title="Safflower oil">Safflower oil</a></td> <td align="right">10.2</td> <td align="right">12.6</td> <td align="right">72.1</td> <td align="right">0</td> <td align="right">40.68 </td></tr> <tr> <td><a href="/wiki/Hemp_oil" title="Hemp oil">Hemp oil</a></td> <td align="right">10</td> <td align="right">15</td> <td align="right">75</td> <td align="right">0</td> <td align="right">12.34 </td></tr> <tr> <td><a href="/wiki/Canola" class="mw-redirect" title="Canola">Canola/Rapeseed oil</a></td> <td align="right">5.3</td> <td align="right">64.3</td> <td align="right">24.8</td> <td align="right">0</td> <td align="right">22.21 </td></tr></tbody></table> <div class="mw-heading mw-heading2"><h2 id="Reactions_of_fatty_acids">Reactions of fatty acids</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fatty_acid&action=edit&section=17" title="Edit section: Reactions of fatty acids"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Fatty acids exhibit reactions like other carboxylic acids, i.e. they undergo <a href="/wiki/Esterification" class="mw-redirect" title="Esterification">esterification</a> and acid-base reactions. </p> <div class="mw-heading mw-heading3"><h3 id="Acidity">Acidity</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fatty_acid&action=edit&section=18" title="Edit section: Acidity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Fatty acids do not show a great variation in their acidities, as indicated by their respective <a href="/wiki/Acid_dissociation_constant" title="Acid dissociation constant">p<i>K</i><sub>a</sub></a>. <a href="/wiki/Nonanoic_acid" class="mw-redirect" title="Nonanoic acid">Nonanoic acid</a>, for example, has a p<i>K</i><sub>a</sub> of 4.96, being only slightly weaker than acetic acid (4.76). As the chain length increases, the solubility of the fatty acids in water decreases, so that the longer-chain fatty acids have minimal effect on the <a href="/wiki/PH" title="PH">pH</a> of an aqueous solution. Near neutral pH, fatty acids exist at their conjugate bases, i.e. oleate, etc. </p><p>Solutions of fatty acids in <a href="/wiki/Ethanol" title="Ethanol">ethanol</a> can be <a href="/wiki/Titration" title="Titration">titrated</a> with <a href="/wiki/Sodium_hydroxide" title="Sodium hydroxide">sodium hydroxide</a> solution using <a href="/wiki/Phenolphthalein" title="Phenolphthalein">phenolphthalein</a> as an indicator. This analysis is used to determine the free fatty acid content of fats; i.e., the proportion of the triglycerides that have been <a href="/wiki/Hydrolysis" title="Hydrolysis">hydrolyzed</a>. </p><p>Neutralization of fatty acids, one form of <a href="/wiki/Saponification" title="Saponification">saponification</a> (soap-making), is a widely practiced route to <a href="/wiki/Metallic_soap" title="Metallic soap">metallic soaps</a>.<sup id="cite_ref-35" class="reference"><a href="#cite_note-35"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Hydrogenation_and_hardening">Hydrogenation and hardening</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fatty_acid&action=edit&section=19" title="Edit section: Hydrogenation and hardening"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Hydrogenation" title="Hydrogenation">Hydrogenation</a> of unsaturated fatty acids is widely practiced. Typical conditions involve 2.0–3.0 MPa of H<sub>2</sub> pressure, 150 °C, and nickel supported on silica as a catalyst. This treatment affords saturated fatty acids. The extent of hydrogenation is indicated by the <a href="/wiki/Iodine_number" class="mw-redirect" title="Iodine number">iodine number</a>. Hydrogenated fatty acids are less prone toward <a href="/wiki/Rancidification" title="Rancidification">rancidification</a>. Since the saturated fatty acids are <a href="/wiki/Melting_point" title="Melting point">higher melting</a> than the unsaturated precursors, the process is called hardening. Related technology is used to convert vegetable oils into <a href="/wiki/Margarine" title="Margarine">margarine</a>. The hydrogenation of triglycerides (vs fatty acids) is advantageous because the carboxylic acids degrade the nickel catalysts, affording nickel soaps. During partial hydrogenation, unsaturated fatty acids can be isomerized from <i>cis</i> to <i>trans</i> configuration.<sup id="cite_ref-Ullmann_Fatty_Acids_21-1" class="reference"><a href="#cite_note-Ullmann_Fatty_Acids-21"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </p><p>More forcing hydrogenation, i.e. using higher pressures of H<sub>2</sub> and higher temperatures, converts fatty acids into <a href="/wiki/Fatty_alcohol" title="Fatty alcohol">fatty alcohols</a>. Fatty alcohols are, however, more easily produced from fatty acid <a href="/wiki/Ester" title="Ester">esters</a>. </p><p>In the <a href="/wiki/Varrentrapp_reaction" title="Varrentrapp reaction">Varrentrapp reaction</a> certain unsaturated fatty acids are cleaved in molten alkali, a reaction which was, at one point of time, relevant to structure elucidation. </p> <div class="mw-heading mw-heading3"><h3 id="Auto-oxidation_and_rancidity">Auto-oxidation and rancidity</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fatty_acid&action=edit&section=20" title="Edit section: Auto-oxidation and rancidity"><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/Rancidification" title="Rancidification">Rancidification</a></div> <p>Unsaturated fatty acids and their esters undergo <a href="/wiki/Auto-oxidation" class="mw-redirect" title="Auto-oxidation">auto-oxidation</a>, which involves replacement of a C-H bond with C-O bond. The process requires oxygen (air) and is accelerated by the presence of traces of metals, which serve as catalysts. Doubly unsaturated fatty acids are particularly prone to this reaction. Vegetable oils resist this process to a small degree because they contain antioxidants, such as <a href="/wiki/Tocopherol" title="Tocopherol">tocopherol</a>. Fats and oils often are treated with <a href="/wiki/Chelation" title="Chelation">chelating agents</a> such as <a href="/wiki/Citric_acid" title="Citric acid">citric acid</a> to remove the metal catalysts. </p> <div class="mw-heading mw-heading3"><h3 id="Ozonolysis">Ozonolysis</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fatty_acid&action=edit&section=21" title="Edit section: Ozonolysis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Unsaturated fatty acids are susceptible to degradation by ozone. This reaction is practiced in the production of <a href="/wiki/Azelaic_acid" title="Azelaic acid">azelaic acid</a> ((CH<sub>2</sub>)<sub>7</sub>(CO<sub>2</sub>H)<sub>2</sub>) from <a href="/wiki/Oleic_acid" title="Oleic acid">oleic acid</a>.<sup id="cite_ref-Ullmann_Fatty_Acids_21-2" class="reference"><a href="#cite_note-Ullmann_Fatty_Acids-21"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Circulation">Circulation</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fatty_acid&action=edit&section=22" title="Edit section: Circulation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Digestion_and_intake">Digestion and intake</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fatty_acid&action=edit&section=23" title="Edit section: Digestion and intake"><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/Digestion#Fat_digestion" title="Digestion">Digestion § Fat digestion</a></div> <p><a href="/wiki/Short-chain_fatty_acid" title="Short-chain fatty acid">Short-</a> and <a href="/wiki/Medium-chain_fatty_acids" class="mw-redirect" title="Medium-chain fatty acids">medium-chain fatty acids</a> are absorbed directly into the blood via intestine capillaries and travel through the <a href="/wiki/Portal_vein" title="Portal vein">portal vein</a> just as other absorbed nutrients do. However, <a href="/wiki/Long-chain_fatty_acids" class="mw-redirect" title="Long-chain fatty acids">long-chain fatty acids</a> are not directly released into the intestinal capillaries. Instead they are absorbed into the fatty walls of the intestine <a href="/wiki/Intestinal_villus" title="Intestinal villus">villi</a> and reassemble again into <a href="/wiki/Triglyceride" title="Triglyceride">triglycerides</a>. The triglycerides are coated with <a href="/wiki/Cholesterol" title="Cholesterol">cholesterol</a> and protein (protein coat) into a compound called a <a href="/wiki/Chylomicron" title="Chylomicron">chylomicron</a>. </p><p>From within the cell, the chylomicron is released into a <a href="/wiki/Lymphatic" class="mw-redirect" title="Lymphatic">lymphatic</a> capillary called a <a href="/wiki/Lacteal" title="Lacteal">lacteal</a>, which merges into larger lymphatic vessels. It is transported via the lymphatic system and the <a href="/wiki/Thoracic_duct" title="Thoracic duct">thoracic duct</a> up to a location near the heart (where the arteries and veins are larger). The thoracic duct empties the chylomicrons into the bloodstream via the left <a href="/wiki/Subclavian_vein" title="Subclavian vein">subclavian vein</a>. At this point the chylomicrons can transport the triglycerides to tissues where they are stored or metabolized for energy. </p> <div class="mw-heading mw-heading3"><h3 id="Metabolism">Metabolism</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fatty_acid&action=edit&section=24" title="Edit section: Metabolism"><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/Fatty_acid_metabolism" title="Fatty acid metabolism">Fatty acid metabolism</a></div> <p>Fatty acids are broken down to CO<sub>2</sub> and water by the intra-cellular <a href="/wiki/Mitochondria" class="mw-redirect" title="Mitochondria">mitochondria</a> through <a href="/wiki/Beta_oxidation" title="Beta oxidation">beta oxidation</a> and the <a href="/wiki/Citric_acid_cycle" title="Citric acid cycle">citric acid cycle</a>. In the final step (<a href="/wiki/Oxidative_phosphorylation" title="Oxidative phosphorylation">oxidative phosphorylation</a>), reactions with oxygen release a lot of energy, captured in the form of large quantities of <a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate">ATP</a>. Many cell types can use either <a href="/wiki/Glucose" title="Glucose">glucose</a> or fatty acids for this purpose, but fatty acids release more energy per gram. Fatty acids (provided either by ingestion or by drawing on triglycerides stored in fatty tissues) are distributed to cells to serve as a fuel for muscular contraction and general metabolism. </p> <div class="mw-heading mw-heading4"><h4 id="Essential_fatty_acids">Essential fatty acids</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fatty_acid&action=edit&section=25" title="Edit section: Essential fatty acids"><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/Essential_fatty_acid" title="Essential fatty acid">Essential fatty acid</a></div> <p>Fatty acids that are required for good health but cannot be made in sufficient quantity from other substrates, and therefore must be obtained from food, are called essential fatty acids. There are two series of essential fatty acids: one has a double bond <a href="/wiki/Omega-3_fatty_acid" title="Omega-3 fatty acid">three carbon atoms</a> away from the methyl end; the other has a double bond <a href="/wiki/Omega-6_fatty_acid" title="Omega-6 fatty acid">six carbon atoms</a> away from the methyl end. Humans lack the ability to introduce double bonds in fatty acids beyond carbons 9 and 10, as counted from the carboxylic acid side.<sup id="cite_ref-36" class="reference"><a href="#cite_note-36"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> Two essential fatty acids are <a href="/wiki/Linoleic_acid" title="Linoleic acid">linoleic acid</a> (LA) and <a href="/wiki/%CE%91-Linolenic_acid" title="Α-Linolenic acid">alpha-linolenic acid</a> (ALA). These fatty acids are widely distributed in plant oils. The human body has a limited ability to convert ALA into the longer-chain <a href="/wiki/Omega-3_fatty_acid" title="Omega-3 fatty acid">omega-3 fatty acids</a> — <a href="/wiki/Eicosapentaenoic_acid" title="Eicosapentaenoic acid">eicosapentaenoic acid</a> (EPA) and <a href="/wiki/Docosahexaenoic_acid" title="Docosahexaenoic acid">docosahexaenoic acid</a> (DHA), which can also be obtained from fish. Omega−3 and <a href="/wiki/Omega-6_fatty_acid" title="Omega-6 fatty acid">omega−6</a> fatty acids are <a href="/wiki/Biosynthesis" title="Biosynthesis">biosynthetic</a> precursors to <a href="/wiki/Cannabinoid#Endocannabinoids" title="Cannabinoid">endocannabinoids</a> with <a href="/wiki/Nociception" title="Nociception">antinociceptive</a>, <a href="/wiki/Anxiolytic" title="Anxiolytic">anxiolytic</a>, and <a href="/wiki/Nervous_system" title="Nervous system">neurogenic</a> properties.<sup id="cite_ref-37" class="reference"><a href="#cite_note-37"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Distribution">Distribution</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fatty_acid&action=edit&section=26" title="Edit section: Distribution"><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/Blood_fatty_acids" class="mw-redirect" title="Blood fatty acids">Blood fatty acids</a></div> <p>Blood fatty acids adopt distinct forms in different stages in the blood circulation. They are taken in through the intestine in <a href="/wiki/Chylomicron" title="Chylomicron">chylomicrons</a>, but also exist in <a href="/wiki/Very_low_density_lipoprotein" class="mw-redirect" title="Very low density lipoprotein">very low density lipoproteins</a> (VLDL) and <a href="/wiki/Low_density_lipoprotein" class="mw-redirect" title="Low density lipoprotein">low density lipoproteins</a> (LDL) after processing in the liver. In addition, when released from <a href="/wiki/Adipocytes" class="mw-redirect" title="Adipocytes">adipocytes</a>, fatty acids exist in the blood as <a href="/wiki/Free_fatty_acids" class="mw-redirect" title="Free fatty acids">free fatty acids</a>. </p><p>It is proposed that the blend of fatty acids exuded by mammalian skin, together with <a href="/wiki/Lactic_acid" title="Lactic acid">lactic acid</a> and <a href="/wiki/Pyruvic_acid" title="Pyruvic acid">pyruvic acid</a>, is distinctive and enables animals with a keen sense of smell to differentiate individuals.<sup id="cite_ref-38" class="reference"><a href="#cite_note-38"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Skin">Skin</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fatty_acid&action=edit&section=27" title="Edit section: Skin"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The <a href="/wiki/Stratum_corneum" title="Stratum corneum">stratum corneum</a> – the outermost layer of the <a href="/wiki/Epidermis" title="Epidermis">epidermis</a> – is composed of terminally <a href="/wiki/Cellular_differentiation" title="Cellular differentiation">differentiated</a> and <a href="/wiki/Enucleation_(microbiology)" title="Enucleation (microbiology)">enucleated</a> <a href="/wiki/Corneocyte" title="Corneocyte">corneocytes</a> within a lipid matrix.<sup id="cite_ref-:0_39-0" class="reference"><a href="#cite_note-:0-39"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> Together with <a href="/wiki/Cholesterol" title="Cholesterol">cholesterol</a> and <a href="/wiki/Ceramide" title="Ceramide">ceramides</a>, free fatty acids form a water-impermeable barrier that prevents <a href="/wiki/Evaporation" title="Evaporation">evaporative water loss</a>.<sup id="cite_ref-:0_39-1" class="reference"><a href="#cite_note-:0-39"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> Generally, the epidermal lipid matrix is composed of an equimolar mixture of ceramides (about 50% by weight), cholesterol (25%), and free fatty acids (15%).<sup id="cite_ref-:0_39-2" class="reference"><a href="#cite_note-:0-39"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> Saturated fatty acids 16 and 18 carbons in length are the dominant types in the epidermis,<sup id="cite_ref-:0_39-3" class="reference"><a href="#cite_note-:0-39"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-:1_40-0" class="reference"><a href="#cite_note-:1-40"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup> while unsaturated fatty acids and saturated fatty acids of various other lengths are also present.<sup id="cite_ref-:0_39-4" class="reference"><a href="#cite_note-:0-39"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-:1_40-1" class="reference"><a href="#cite_note-:1-40"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup> The relative abundance of the different fatty acids in the epidermis is dependent on the body site the skin is covering.<sup id="cite_ref-:1_40-2" class="reference"><a href="#cite_note-:1-40"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup> There are also characteristic epidermal fatty acid alterations that occur in <a href="/wiki/Psoriasis" title="Psoriasis">psoriasis</a>, <a href="/wiki/Atopic_dermatitis" title="Atopic dermatitis">atopic dermatitis</a>, and other <a href="/wiki/Inflammation" title="Inflammation">inflammatory conditions</a>.<sup id="cite_ref-:0_39-5" class="reference"><a href="#cite_note-:0-39"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-:1_40-3" class="reference"><a href="#cite_note-:1-40"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Analysis">Analysis</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fatty_acid&action=edit&section=28" title="Edit section: Analysis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The chemical analysis of fatty acids in lipids typically begins with an <a href="/wiki/Interesterification" class="mw-redirect" title="Interesterification">interesterification</a> step that breaks down their original esters (triglycerides, waxes, phospholipids etc.) and converts them to <a href="/wiki/Methyl" class="mw-redirect" title="Methyl">methyl</a> esters, which are then separated by gas chromatography<sup id="cite_ref-41" class="reference"><a href="#cite_note-41"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup> or analyzed by <a href="/wiki/Gas_chromatography" title="Gas chromatography">gas chromatography</a> and mid-<a href="/wiki/Infrared_spectroscopy" title="Infrared spectroscopy">infrared spectroscopy</a>. </p><p>Separation of unsaturated isomers is possible by <a href="/wiki/Argentation_chromatography" title="Argentation chromatography">silver ion complemented thin-layer chromatography</a>.<sup id="cite_ref-42" class="reference"><a href="#cite_note-42"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup> Other separation techniques include <a href="/wiki/High-performance_liquid_chromatography" title="High-performance liquid chromatography">high-performance liquid chromatography</a> (with short columns packed with <a href="/wiki/Silica_gel" title="Silica gel">silica gel</a> with bonded phenylsulfonic acid groups whose hydrogen atoms have been exchanged for silver ions). The role of silver lies in its ability to form complexes with unsaturated compounds. </p> <div class="mw-heading mw-heading2"><h2 id="Industrial_uses">Industrial uses</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fatty_acid&action=edit&section=29" title="Edit section: Industrial uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Fatty acids are mainly used in the production of <a href="/wiki/Soap" title="Soap">soap</a>, both for cosmetic purposes and, in the case of <a href="/wiki/Metallic_soap" title="Metallic soap">metallic soaps</a>, as lubricants. Fatty acids are also converted, via their methyl esters, to <a href="/wiki/Fatty_alcohol" title="Fatty alcohol">fatty alcohols</a> and <a href="/wiki/Fatty_amine" title="Fatty amine">fatty amines</a>, which are precursors to surfactants, detergents, and lubricants.<sup id="cite_ref-Ullmann_Fatty_Acids_21-3" class="reference"><a href="#cite_note-Ullmann_Fatty_Acids-21"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> Other applications include their use as <a href="/wiki/Emulsion#Emulsifiers" title="Emulsion">emulsifiers</a>, texturizing agents, wetting agents, <a href="/wiki/Defoamer" title="Defoamer">anti-foam agents</a>, or stabilizing agents.<sup id="cite_ref-buildingblocks_43-0" class="reference"><a href="#cite_note-buildingblocks-43"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup> </p><p>Esters of fatty acids with simpler alcohols (such as methyl-, ethyl-, n-propyl-, isopropyl- and butyl esters) are used as emollients in cosmetics and other personal care products and as synthetic lubricants. Esters of fatty acids with more complex alcohols, such as <a href="/wiki/Sorbitol" title="Sorbitol">sorbitol</a>, <a href="/wiki/Ethylene_glycol" title="Ethylene glycol">ethylene glycol</a>, <a href="/wiki/Diethylene_glycol" title="Diethylene glycol">diethylene glycol</a>, and <a href="/wiki/Polyethylene_glycol" title="Polyethylene glycol">polyethylene glycol</a> are consumed in food, or used for personal care and water treatment, or used as synthetic lubricants or fluids for metal working. </p><p><br /> </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=Fatty_acid&action=edit&section=30" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1235681985">.mw-parser-output .side-box{margin:4px 0;box-sizing:border-box;border:1px solid #aaa;font-size:88%;line-height:1.25em;background-color:var(--background-color-interactive-subtle,#f8f9fa);display:flow-root}.mw-parser-output .side-box-abovebelow,.mw-parser-output .side-box-text{padding:0.25em 0.9em}.mw-parser-output .side-box-image{padding:2px 0 2px 0.9em;text-align:center}.mw-parser-output .side-box-imageright{padding:2px 0.9em 2px 0;text-align:center}@media(min-width:500px){.mw-parser-output .side-box-flex{display:flex;align-items:center}.mw-parser-output .side-box-text{flex:1;min-width:0}}@media(min-width:720px){.mw-parser-output .side-box{width:238px}.mw-parser-output .side-box-right{clear:right;float:right;margin-left:1em}.mw-parser-output .side-box-left{margin-right:1em}}</style><style data-mw-deduplicate="TemplateStyles:r1237033735">@media print{body.ns-0 .mw-parser-output .sistersitebox{display:none!important}}@media screen{html.skin-theme-clientpref-night .mw-parser-output .sistersitebox img[src*="Wiktionary-logo-en-v2.svg"]{background-color:white}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .sistersitebox img[src*="Wiktionary-logo-en-v2.svg"]{background-color:white}}</style><div class="side-box side-box-right plainlinks sistersitebox"><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="side-box-flex"> <div class="side-box-image"><span class="noviewer" typeof="mw:File"><span><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/30px-Commons-logo.svg.png" decoding="async" width="30" height="40" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/45px-Commons-logo.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/59px-Commons-logo.svg.png 2x" data-file-width="1024" data-file-height="1376" /></span></span></div> <div class="side-box-text plainlist">Wikimedia Commons has media related to <a href="https://commons.wikimedia.org/wiki/Fatty_acids" class="extiw" title="commons:Fatty acids"><span style="font-style:italic; font-weight:bold;">Fatty acids</span></a>.</div></div> </div> <style data-mw-deduplicate="TemplateStyles:r1184024115">.mw-parser-output .div-col{margin-top:0.3em;column-width:30em}.mw-parser-output .div-col-small{font-size:90%}.mw-parser-output .div-col-rules{column-rule:1px solid #aaa}.mw-parser-output .div-col dl,.mw-parser-output .div-col ol,.mw-parser-output .div-col ul{margin-top:0}.mw-parser-output .div-col li,.mw-parser-output .div-col dd{page-break-inside:avoid;break-inside:avoid-column}</style><div class="div-col" style="column-width: 30em;"> <ul><li><a href="/wiki/Fatty_acid_synthase" title="Fatty acid synthase">Fatty acid synthase</a></li> <li><a href="/wiki/Fatty_acid_synthesis" title="Fatty acid synthesis">Fatty acid synthesis</a></li> <li><a href="/wiki/Fatty_aldehyde" title="Fatty aldehyde">Fatty aldehyde</a></li> <li><a href="/wiki/List_of_saturated_fatty_acids" title="List of saturated fatty acids">List of saturated fatty acids</a></li> <li><a href="/wiki/List_of_unsaturated_fatty_acids" title="List of unsaturated fatty acids">List of unsaturated fatty acids</a></li> <li><a href="/wiki/List_of_carboxylic_acids" title="List of carboxylic acids">List of carboxylic acids</a></li> <li><a href="/wiki/Vegetable_oil" title="Vegetable oil">Vegetable oil</a></li> <li><a href="/wiki/Lactobacillic_acid" title="Lactobacillic acid">Lactobacillic acid</a></li></ul> </div> <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=Fatty_acid&action=edit&section=31" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist reflist-lower-alpha"> <div class="mw-references-wrap"><ol class="references"> <li id="cite_note-c:d-10"><span class="mw-cite-backlink">^ <a href="#cite_ref-c:d_10-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-c:d_10-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-c:d_10-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text">"C:D" is the numerical symbol: total amount of (C)arbon atoms of the fatty acid, and the number of (D)ouble (<i>unsaturated</i>) bonds in it; if D > 1 it is assumed that the double bonds are separated by one or more <a href="/wiki/Methylene_bridge" title="Methylene bridge">methylene bridge</a>(s).</span> </li> <li id="cite_note-11"><span class="mw-cite-backlink"><b><a href="#cite_ref-11">^</a></b></span> <span class="reference-text">Each double bond in the fatty acid is indicated by Δx, where the double bond is located on the xth carbon–carbon bond, counting from the carboxylic acid end.</span> </li> <li id="cite_note-omega-x-13"><span class="mw-cite-backlink"><b><a href="#cite_ref-omega-x_13-0">^</a></b></span> <span class="reference-text">In <i>n minus x</i> (also ω−x or omega-x) nomenclature a double bond of the fatty acid is located on the xth carbon–carbon bond, counting from the terminal methyl carbon (designated as n or ω) toward the carbonyl carbon.</span> </li> <li id="cite_note-note.omega-16"><span class="mw-cite-backlink">^ <a href="#cite_ref-note.omega_16-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-note.omega_16-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-note.omega_16-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text">A common mistake is to say that the last carbon is "ω−1".<br />Another common mistake is to say that the position of a bond in omega-notation is the number of the carbon closest to the END.<br />For double bonds, these two mistakes happen to compensate each other; so that a "ω−3" fatty acid indeed has the double bond between the 3rd and 4th carbons from the end, counting the methyl as 1.<br />However, for substitutions and other purposes, they don't: a hydroxyl "at ω−3" is on carbon 15 (4th from the end), not 16. See for example this article. <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><a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2F0005-2760%2875%2990089-2">10.1016/0005-2760(75)90089-2</a><br />Note also that the "−" in the omega-notation is a minus sign, and "ω−3" should in principle be read "omega minus three". However, it is very common (especially in non-scientific literature) to write it "ω-3" (with a hyphen/dash) and read it as "omega-three". See for example Karen Dooley (2008), <a rel="nofollow" class="external text" href="https://podcasts.ufhealth.org/omega-three-fatty-acids-and-diabetes/">Omega-three fatty acids and diabetes</a>.</span> </li> </ol></div></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239543626"><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-iupac-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-iupac_1-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMossSmithTavernier1997" class="citation journal cs1">Moss, G. P.; Smith, P. A. S.; Tavernier, D. 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John Wiley and Sons. pp. <a rel="nofollow" class="external text" href="https://archive.org/details/fundamentalsofbi00voet_0/page/547">547, 556</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-471-21495-3" title="Special:BookSources/978-0-471-21495-3"><bdi>978-0-471-21495-3</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Fundamentals+of+Biochemistry&rft.pages=547%2C+556&rft.edition=2nd&rft.pub=John+Wiley+and+Sons&rft.date=2006&rft.isbn=978-0-471-21495-3&rft.aulast=Voet&rft.aufirst=Donald&rft.au=Voet%2C+Judith+G.&rft.au=Pratt%2C+Charlotte+W.&rft_id=https%3A%2F%2Farchive.org%2Fdetails%2Ffundamentalsofbi00voet_0%2Fpage%2F547&rfr_id=info%3Asid%2Fen.wikipedia.org%3AFatty+acid" class="Z3988"></span></span> </li> <li id="cite_note-25"><span class="mw-cite-backlink"><b><a href="#cite_ref-25">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFZechnerStraussHaemmerleLass2005" class="citation journal cs1">Zechner, R.; Strauss, J. 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Based on these reports, valproic acid is thought to be transported bidirectionally between blood and brain across the BBB via two distinct mechanisms, monocarboxylic acid-sensitive and medium-chain fatty acid-sensitive transporters, for efflux and uptake, respectively.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=NeuroRx&rft.atitle=Small+molecular+drug+transfer+across+the+blood%E2%80%93brain+barrier+via+carrier-mediated+transport+systems&rft.volume=2&rft.issue=1&rft.pages=54-62&rft.date=2005&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC539320%23id-name%3DPMC&rft_id=info%3Apmid%2F15717057&rft_id=info%3Adoi%2F10.1602%2Fneurorx.2.1.54&rft.aulast=Tsuji&rft.aufirst=A&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC539320&rfr_id=info%3Asid%2Fen.wikipedia.org%3AFatty+acid" class="Z3988"></span></span> </li> <li id="cite_note-SCFA_MCT-mediated_BBB_passage_-_2014_review-27"><span class="mw-cite-backlink"><b><a href="#cite_ref-SCFA_MCT-mediated_BBB_passage_-_2014_review_27-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFVijayMorris2014" class="citation journal cs1">Vijay N, Morris ME (2014). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4084603">"Role of monocarboxylate transporters in drug delivery to the brain"</a>. <i>Curr. 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Retrieved <span class="nowrap">22 Apr</span> 2018</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=aciscience.org&rft.atitle=Fatty+Acids%3A+Building+Blocks+for+Industry&rft_id=http%3A%2F%2Fwww.aciscience.org%2Fdocs%2FFatty_Acids_Building_Blocks_for_Industry.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3AFatty+acid" class="Z3988"></span></span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Fatty_acid&action=edit&section=32" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1235681985"><div class="side-box metadata side-box-right"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"> <div class="side-box-flex"> <div class="side-box-image"><span class="noviewer" typeof="mw:File"><span><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/3/32/Scholia_logo.svg/40px-Scholia_logo.svg.png" decoding="async" width="40" height="39" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/32/Scholia_logo.svg/60px-Scholia_logo.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/32/Scholia_logo.svg/80px-Scholia_logo.svg.png 2x" data-file-width="107" data-file-height="104" /></span></span></div> <div class="side-box-text plainlist"><a href="https://www.wikidata.org/wiki/Wikidata:Scholia" class="extiw" title="d:Wikidata:Scholia">Scholia</a> has a <i>chemical-class</i> profile for <i><b><a href="https://iw.toolforge.org/scholia/chemical-class/Q61476" class="extiw" title="toolforge:scholia/chemical-class/Q61476">Fatty acid</a></b></i>.</div></div> </div> <ul><li><a rel="nofollow" class="external text" href="http://lipidlibrary.aocs.org/">Lipid Library</a></li> <li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20071012173913/http://intl.elsevierhealth.com/journals/plef/"><i>Prostaglandins, Leukotrienes & Essential Fatty Acids</i> journal</a></li> <li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20110720155135/http://www.dmfpolska.eu/diagnostics.html">Fatty blood acids </a></li></ul> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><style data-mw-deduplicate="TemplateStyles:r1236075235">.mw-parser-output .navbox{box-sizing:border-box;border:1px solid #a2a9b1;width:100%;clear:both;font-size:88%;text-align:center;padding:1px;margin:1em auto 0}.mw-parser-output .navbox .navbox{margin-top:0}.mw-parser-output .navbox+.navbox,.mw-parser-output .navbox+.navbox-styles+.navbox{margin-top:-1px}.mw-parser-output .navbox-inner,.mw-parser-output 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.navbox-abovebelow{background-color:#e6e6ff}.mw-parser-output .navbox-even{background-color:#f7f7f7}.mw-parser-output .navbox-odd{background-color:transparent}.mw-parser-output .navbox .hlist td dl,.mw-parser-output .navbox .hlist td ol,.mw-parser-output .navbox .hlist td ul,.mw-parser-output .navbox td.hlist dl,.mw-parser-output .navbox td.hlist ol,.mw-parser-output .navbox td.hlist ul{padding:0.125em 0}.mw-parser-output .navbox .navbar{display:block;font-size:100%}.mw-parser-output .navbox-title .navbar{float:left;text-align:left;margin-right:0.5em}body.skin--responsive .mw-parser-output .navbox-image img{max-width:none!important}@media print{body.ns-0 .mw-parser-output .navbox{display:none!important}}</style></div><div role="navigation" class="navbox" aria-labelledby="Lipids:_fatty_acids" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Fatty_acids" title="Template:Fatty acids"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Fatty_acids" title="Template talk:Fatty acids"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Fatty_acids" title="Special:EditPage/Template:Fatty acids"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Lipids:_fatty_acids" style="font-size:114%;margin:0 4em"><a href="/wiki/Lipid" title="Lipid">Lipids</a>: <a class="mw-selflink selflink">fatty acids</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Saturated_fat" title="Saturated fat">Saturated</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Propionic_acid" title="Propionic acid">Propionic</a> (C3)</li> <li><a href="/wiki/Butyric_acid" title="Butyric acid">Butyric</a> (C4)</li> <li><a href="/wiki/Valeric_acid" title="Valeric acid">Valeric</a> (C5)</li> <li><a href="/wiki/Caproic_acid" title="Caproic acid">Caproic</a> (C6)</li> <li><a href="/wiki/Enanthic_acid" title="Enanthic acid">Enanthic</a> (C7)</li> <li><a href="/wiki/Caprylic_acid" title="Caprylic acid">Caprylic</a> (C8)</li> <li><a href="/wiki/Pelargonic_acid" title="Pelargonic acid">Pelargonic</a> (C9)</li> <li><a href="/wiki/Capric_acid" title="Capric acid">Capric</a> (C10)</li> <li><a href="/wiki/Undecylic_acid" title="Undecylic acid">Undecylic</a> (C11)</li> <li><a href="/wiki/Lauric_acid" title="Lauric acid">Lauric</a> (C12)</li> <li><a href="/wiki/Tridecylic_acid" title="Tridecylic acid">Tridecylic</a> (C13)</li> <li><a href="/wiki/Myristic_acid" title="Myristic acid">Myristic</a> (C14)</li> <li><a href="/wiki/Pentadecylic_acid" title="Pentadecylic acid">Pentadecylic</a> (C15)</li> <li><a href="/wiki/Palmitic_acid" title="Palmitic acid">Palmitic</a> (C16)</li> <li><a href="/wiki/Margaric_acid" title="Margaric acid">Margaric</a> (C17)</li> <li><a href="/wiki/Stearic_acid" title="Stearic acid">Stearic</a> (C18)</li> <li><a href="/wiki/Nonadecylic_acid" title="Nonadecylic acid">Nonadecylic</a> (C19)</li> <li><a href="/wiki/Arachidic_acid" title="Arachidic acid">Arachidic</a> (C20)</li> <li><a href="/wiki/Heneicosylic_acid" title="Heneicosylic acid">Heneicosylic</a> (C21)</li> <li><a href="/wiki/Behenic_acid" title="Behenic acid">Behenic</a> (C22)</li> <li><a href="/wiki/Tricosylic_acid" title="Tricosylic acid">Tricosylic</a> (C23)</li> <li><a href="/wiki/Lignoceric_acid" title="Lignoceric acid">Lignoceric</a> (C24)</li> <li><a href="/wiki/Pentacosylic_acid" title="Pentacosylic acid">Pentacosylic</a> (C25)</li> <li><a href="/wiki/Cerotic_acid" title="Cerotic acid">Cerotic</a> (C26)</li> <li><a href="/wiki/Carboceric_acid" title="Carboceric acid">Carboceric</a> (C27)</li> <li><a href="/wiki/Montanic_acid" title="Montanic acid">Montanic</a> (C28)</li> <li><a href="/wiki/Nonacosylic_acid" title="Nonacosylic acid">Nonacosylic</a> (C29)</li> <li><a href="/wiki/Melissic_acid" title="Melissic acid">Melissic</a> (C30)</li> <li><a href="/wiki/Hentriacontylic_acid" title="Hentriacontylic acid">Hentriacontylic</a> (C31)</li> <li><a href="/wiki/Lacceroic_acid" title="Lacceroic acid">Lacceroic</a> (C32)</li> <li><a href="/wiki/Psyllic_acid" title="Psyllic acid">Psyllic</a> (C33)</li> <li><a href="/wiki/Geddic_acid" title="Geddic acid">Geddic</a> (C34)</li> <li><a href="/wiki/Ceroplastic_acid" title="Ceroplastic acid">Ceroplastic</a> (C35)</li> <li><a href="/wiki/Hexatriacontylic_acid" title="Hexatriacontylic acid">Hexatriacontylic</a> (C36)</li> <li><a href="/wiki/Heptatriacontanoic_acid" title="Heptatriacontanoic acid">Heptatriacontanoic</a> (C37)</li> <li><a href="/w/index.php?title=Octatriacontanoic_acid&action=edit&redlink=1" class="new" title="Octatriacontanoic acid (page does not exist)">Octatriacontanoic</a> (C38)</li> <li><a href="/w/index.php?title=Nonatriacontanoic_acid&action=edit&redlink=1" class="new" title="Nonatriacontanoic acid (page does not exist)">Nonatriacontanoic</a> (C39)</li> <li><a href="/w/index.php?title=Tetracontanoic_acid&action=edit&redlink=1" class="new" title="Tetracontanoic acid (page does not exist)">Tetracontanoic</a> (C40)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Omega-3_fatty_acid" title="Omega-3 fatty acid">ω−3 Unsaturated</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=5-Octenoic_acid&action=edit&redlink=1" class="new" title="5-Octenoic acid (page does not exist)">Octenoic</a> (8:1)</li> <li><a href="/w/index.php?title=7-Decenoic_acid&action=edit&redlink=1" class="new" title="7-Decenoic acid (page does not exist)">Decenoic</a> (10:1)</li> <li><a href="/w/index.php?title=4,7-Decadienoic_acid&action=edit&redlink=1" class="new" title="4,7-Decadienoic acid (page does not exist)">Decadienoic</a> (10:2)</li> <li><a href="/w/index.php?title=9-Dodecenoic_acid&action=edit&redlink=1" class="new" title="9-Dodecenoic acid (page does not exist)">Lauroleic</a> (12:1)</li> <li><a href="/w/index.php?title=6,9-Dodecadienoic_acid&action=edit&redlink=1" class="new" title="6,9-Dodecadienoic acid (page does not exist)">Laurolinoleic</a> (12:2)</li> <li><a href="/w/index.php?title=11-Tetradecenoic_acid&action=edit&redlink=1" class="new" title="11-Tetradecenoic acid (page does not exist)">Myristovaccenic</a> (14:1)</li> <li><a href="/w/index.php?title=8,11-Tetradecadienoic_acid&action=edit&redlink=1" class="new" title="8,11-Tetradecadienoic acid (page does not exist)">Myristolinoleic</a> (14:2)</li> <li><a href="/w/index.php?title=5,8,11-Tetradecatrienoic_acid&action=edit&redlink=1" class="new" title="5,8,11-Tetradecatrienoic acid (page does not exist)">Myristolinolenic</a> (14:3)</li> <li><a href="/w/index.php?title=7,10,13-Hexadecatrienoic_acid&action=edit&redlink=1" class="new" title="7,10,13-Hexadecatrienoic acid (page does not exist)">Palmitolinolenic</a> (16:3)</li> <li><a href="/w/index.php?title=4,7,10,13-Hexadecatetraenoic_acid&action=edit&redlink=1" class="new" title="4,7,10,13-Hexadecatetraenoic acid (page does not exist)">Palmitidonic</a> (16:4)</li> <li><a href="/wiki/%CE%91-Linolenic_acid" title="Α-Linolenic acid">α-Linolenic</a> (18:3)</li> <li><a href="/wiki/Stearidonic_acid" title="Stearidonic acid">Stearidonic</a> (18:4)</li> <li><a href="/wiki/%CE%91-Parinaric_acid" title="Α-Parinaric acid">α-Parinaric</a> (18:4)</li> <li><a href="/w/index.php?title=11,14,17-Eicosatrienoic_acid&action=edit&redlink=1" class="new" title="11,14,17-Eicosatrienoic acid (page does not exist)">Dihomo-α-linolenic</a> (20:3)</li> <li><a href="/wiki/Eicosatetraenoic_acid" title="Eicosatetraenoic acid">Eicosatetraenoic</a> (20:4)</li> <li><a href="/wiki/Eicosapentaenoic_acid" title="Eicosapentaenoic acid">Eicosapentaenoic</a> (20:5)</li> <li><a href="/wiki/Docosapentaenoic_acid" title="Docosapentaenoic acid">Clupanodonic</a> (22:5)</li> <li><a href="/wiki/Docosahexaenoic_acid" title="Docosahexaenoic acid">Docosahexaenoic</a> (22:6)</li> <li><a href="/w/index.php?title=9,12,15,18,21-Tetracosapentaenoic_acid&action=edit&redlink=1" class="new" title="9,12,15,18,21-Tetracosapentaenoic acid (page does not exist)">9,12,15,18,21-Tetracosapentaenoic</a> (24:5)</li> <li><a href="/w/index.php?title=6,9,12,15,18,21-Tetracosahexaenoic_acid&action=edit&redlink=1" class="new" title="6,9,12,15,18,21-Tetracosahexaenoic acid (page does not exist)">6,9,12,15,18,21-Tetracosahexaenoic</a> (24:6)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/w/index.php?title=Omega-5_fatty_acid&action=edit&redlink=1" class="new" title="Omega-5 fatty acid (page does not exist)">ω−5 Unsaturated</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Myristoleic_acid" title="Myristoleic acid">Myristoleic</a> (14:1)</li> <li><a href="/w/index.php?title=11-Hexadecenoic_acid&action=edit&redlink=1" class="new" title="11-Hexadecenoic acid (page does not exist)">Palmitovaccenic</a> (16:1)</li> <li><a href="/wiki/%CE%91-Eleostearic_acid" title="Α-Eleostearic acid">α-Eleostearic</a> (18:3)</li> <li><a href="/wiki/%CE%92-Eleostearic_acid" title="Β-Eleostearic acid">β-Eleostearic</a> (<i>trans</i>-18:3)</li> <li><a href="/wiki/Punicic_acid" title="Punicic acid">Punicic</a> (18:3)</li> <li><a href="/w/index.php?title=7,10,13-Octadecatrienoic_acid&action=edit&redlink=1" class="new" title="7,10,13-Octadecatrienoic acid (page does not exist)">7,10,13-Octadecatrienoic</a> (18:3)</li> <li><a href="/w/index.php?title=9,12,15-Eicosatrienoic_acid&action=edit&redlink=1" class="new" title="9,12,15-Eicosatrienoic acid (page does not exist)">9,12,15-Eicosatrienoic</a> (20:3)</li> <li><a href="/w/index.php?title=6,9,12,15-Eicosatetraenoic_acid&action=edit&redlink=1" class="new" title="6,9,12,15-Eicosatetraenoic acid (page does not exist)">β-Eicosatetraenoic</a> (20:4)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Omega-6_fatty_acid" title="Omega-6 fatty acid">ω−6 Unsaturated</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=8-Tetradecenoic_acid&action=edit&redlink=1" class="new" title="8-Tetradecenoic acid (page does not exist)">8-Tetradecenoic</a> (14:1)</li> <li><a href="/w/index.php?title=12-Octadecenoic_acid&action=edit&redlink=1" class="new" title="12-Octadecenoic acid (page does not exist)">12-Octadecenoic</a> (18:1)</li> <li><a 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="Fatty_acid_metabolic_intermediates" style="padding:3px"><table class="nowraplinks hlist mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Fatty-acid_metabolism_intermediates" title="Template:Fatty-acid metabolism intermediates"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Fatty-acid_metabolism_intermediates" title="Template talk:Fatty-acid metabolism intermediates"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Fatty-acid_metabolism_intermediates" title="Special:EditPage/Template:Fatty-acid metabolism intermediates"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Fatty_acid_metabolic_intermediates" style="font-size:114%;margin:0 4em"><a class="mw-selflink selflink">Fatty acid</a> <a href="/wiki/Metabolic_intermediate" title="Metabolic intermediate">metabolic intermediates</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">Synthesis</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetyl-CoA" title="Acetyl-CoA">Acetyl-CoA</a></li> <li><a href="/wiki/Malonyl-CoA" title="Malonyl-CoA">Malonyl-CoA</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Degradation</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acyl-CoA" title="Acyl-CoA">Acyl-CoA</a></li> <li><a href="/wiki/Acetyl-CoA" title="Acetyl-CoA">Acetyl-CoA</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Peroxisome" title="Peroxisome">Peroxisomal</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phytol" title="Phytol">Phytol</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Phytanic_acid" title="Phytanic acid">Phytanic acid</a></li> <li><a href="/wiki/Phytanoyl-CoA" title="Phytanoyl-CoA">Phytanoyl-CoA</a></li> <li><a href="/wiki/Pristanic_acid" title="Pristanic acid">Pristanic acid</a></li> <li><a href="/wiki/Propionyl-CoA" title="Propionyl-CoA">Propionyl-CoA</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Mevalonic_acid" title="Mevalonic acid">Mevalonic acid</a></li> <li><a href="/wiki/Very_long_chain_fatty_acid" title="Very long chain fatty acid">Very long chain fatty acid</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"><style data-mw-deduplicate="TemplateStyles:r1038841319">.mw-parser-output .tooltip-dotted{border-bottom:1px dotted;cursor:help}</style><link rel="mw-deduplicated-inline-style" 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