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href="#Absorption,_metabolism_and_excretion"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>Absorption, metabolism and excretion</span> </div> </a> <ul id="toc-Absorption,_metabolism_and_excretion-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Conversion_factors" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Conversion_factors"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Conversion factors</span> </div> </a> <button aria-controls="toc-Conversion_factors-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 Conversion factors subsection</span> </button> <ul id="toc-Conversion_factors-sublist" class="vector-toc-list"> <li id="toc-Retinol_activity_equivalents_(RAEs)" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Retinol_activity_equivalents_(RAEs)"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.1</span> <span>Retinol activity equivalents (RAEs)</span> </div> </a> <ul id="toc-Retinol_activity_equivalents_(RAEs)-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-International_Units" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#International_Units"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.2</span> <span>International Units</span> </div> </a> <ul id="toc-International_Units-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Dietary_sources" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Dietary_sources"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Dietary sources</span> </div> </a> <button aria-controls="toc-Dietary_sources-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Dietary sources subsection</span> </button> <ul id="toc-Dietary_sources-sublist" class="vector-toc-list"> <li id="toc-No_dietary_requirement" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#No_dietary_requirement"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.1</span> <span>No dietary requirement</span> </div> </a> <ul id="toc-No_dietary_requirement-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Side_effects" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Side_effects"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Side effects</span> </div> </a> <button aria-controls="toc-Side_effects-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Side effects subsection</span> </button> <ul id="toc-Side_effects-sublist" class="vector-toc-list"> <li id="toc-Carotenosis" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Carotenosis"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1</span> <span>Carotenosis</span> </div> </a> <ul id="toc-Carotenosis-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-No_risk_for_hypervitaminosis_A" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#No_risk_for_hypervitaminosis_A"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.2</span> <span>No risk for hypervitaminosis A</span> </div> </a> <ul id="toc-No_risk_for_hypervitaminosis_A-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Drug_interactions" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Drug_interactions"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.3</span> <span>Drug interactions</span> </div> </a> <ul id="toc-Drug_interactions-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-β-Carotene_and_lung_cancer_in_smokers" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#β-Carotene_and_lung_cancer_in_smokers"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.4</span> <span>β-Carotene and lung cancer in smokers</span> </div> </a> <ul id="toc-β-Carotene_and_lung_cancer_in_smokers-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Industrial_sources" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Industrial_sources"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Industrial sources</span> </div> </a> <ul id="toc-Industrial_sources-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Research" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Research"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Research</span> </div> </a> <button aria-controls="toc-Research-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 Research subsection</span> </button> <ul id="toc-Research-sublist" class="vector-toc-list"> <li id="toc-Macular_degeneration" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Macular_degeneration"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.1</span> <span>Macular degeneration</span> </div> </a> <ul id="toc-Macular_degeneration-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Cancer" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Cancer"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.2</span> <span>Cancer</span> </div> </a> <ul id="toc-Cancer-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Cataract" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Cataract"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.3</span> <span>Cataract</span> </div> </a> <ul id="toc-Cataract-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Erythropoietic_protoporphyria" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Erythropoietic_protoporphyria"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.4</span> <span>Erythropoietic protoporphyria</span> </div> </a> <ul id="toc-Erythropoietic_protoporphyria-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Food_drying" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Food_drying"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.5</span> <span>Food drying</span> </div> </a> <ul id="toc-Food_drying-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>See also</span> </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span class="vector-dropdown-label-text">Toggle the table of contents</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading">β-Carotene</h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="Go to an article in another language. Available in 39 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-39" 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">39 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%A8%D9%8A%D8%AA%D8%A7_%D9%83%D8%A7%D8%B1%D9%88%D8%AA%D9%8A%D9%86" title="بيتا كاروتين – Arabic" lang="ar" hreflang="ar" data-title="بيتا كاروتين" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D8%A8%D8%AA%D8%A7%DA%A9%D8%A7%D8%B1%D9%88%D8%AA%D9%86" title="بتاکاروتن – South Azerbaijani" lang="azb" hreflang="azb" data-title="بتاکاروتن" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-bn mw-list-item"><a href="https://bn.wikipedia.org/wiki/%E0%A6%AC%E0%A6%BF%E0%A6%9F%E0%A6%BE-%E0%A6%95%E0%A7%8D%E0%A6%AF%E0%A6%BE%E0%A6%B0%E0%A7%8B%E0%A6%9F%E0%A6%BF%E0%A6%A8" title="বিটা-ক্যারোটিন – Bangla" lang="bn" hreflang="bn" data-title="বিটা-ক্যারোটিন" data-language-autonym="বাংলা" data-language-local-name="Bangla" class="interlanguage-link-target"><span>বাংলা</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%91%D0%B5%D1%82%D0%B0_%D0%BA%D0%B0%D1%80%D0%BE%D1%82%D0%B8%D0%BD" title="Бета каротин – Bulgarian" lang="bg" hreflang="bg" data-title="Бета каротин" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target"><span>Български</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Betacarot%C3%A8" title="Betacarotè – Catalan" lang="ca" hreflang="ca" data-title="Betacarotè" 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/Betakaroten" title="Betakaroten – Czech" lang="cs" hreflang="cs" data-title="Betakaroten" 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/Betakaroten" title="Betakaroten – Danish" lang="da" hreflang="da" data-title="Betakaroten" data-language-autonym="Dansk" data-language-local-name="Danish" class="interlanguage-link-target"><span>Dansk</span></a></li><li class="interlanguage-link interwiki-de badge-Q70894304 mw-list-item" title=""><a href="https://de.wikipedia.org/wiki/%CE%92-Carotin" title="Β-Carotin – German" lang="de" hreflang="de" data-title="Β-Carotin" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/%CE%92-caroteno" title="Β-caroteno – Spanish" lang="es" hreflang="es" data-title="Β-caroteno" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Beta-karoteno" title="Beta-karoteno – Basque" lang="eu" hreflang="eu" data-title="Beta-karoteno" 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%A8%D8%AA%D8%A7-%DA%A9%D8%A7%D8%B1%D9%88%D8%AA%D9%86" title="بتا-کاروتن – Persian" lang="fa" hreflang="fa" data-title="بتا-کاروتن" 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/B%C3%AAta-Carot%C3%A8ne" title="Bêta-Carotène – French" lang="fr" hreflang="fr" data-title="Bêta-Carotène" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Beta-caroteno" title="Beta-caroteno – Galician" lang="gl" hreflang="gl" data-title="Beta-caroteno" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EB%B2%A0%ED%83%80-%EC%B9%B4%EB%A1%9C%ED%8B%B4" title="베타-카로틴 – Korean" lang="ko" hreflang="ko" data-title="베타-카로틴" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hi mw-list-item"><a href="https://hi.wikipedia.org/wiki/%E0%A4%AC%E0%A5%80%E0%A4%9F%E0%A4%BE_%E0%A4%95%E0%A5%88%E0%A4%B0%E0%A5%8B%E0%A4%9F%E0%A5%80%E0%A4%A8" title="बीटा कैरोटीन – Hindi" lang="hi" hreflang="hi" data-title="बीटा कैरोटीन" data-language-autonym="हिन्दी" data-language-local-name="Hindi" class="interlanguage-link-target"><span>हिन्दी</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Beta-karoten" title="Beta-karoten – Indonesian" lang="id" hreflang="id" data-title="Beta-karoten" 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/Beta-kar%C3%B3t%C3%ADn" title="Beta-karótín – Icelandic" lang="is" hreflang="is" data-title="Beta-karótín" 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/Beta-carotene" title="Beta-carotene – Italian" lang="it" hreflang="it" data-title="Beta-carotene" 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%91%D7%98%D7%90-%D7%A7%D7%A8%D7%95%D7%98%D7%9F" title="בטא-קרוטן – Hebrew" lang="he" hreflang="he" data-title="בטא-קרוטן" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/B%C3%A9ta-karotin" title="Béta-karotin – Hungarian" lang="hu" hreflang="hu" data-title="Béta-karotin" 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%91%D0%B5%D1%82%D0%B0-%D0%BA%D0%B0%D1%80%D0%BE%D1%82%D0%B8%D0%BD" title="Бета-каротин – Macedonian" lang="mk" hreflang="mk" data-title="Бета-каротин" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Beta-Karotena" title="Beta-Karotena – Malay" lang="ms" hreflang="ms" data-title="Beta-Karotena" 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-mn mw-list-item"><a href="https://mn.wikipedia.org/wiki/%D0%91%D0%B5%D1%82%D0%B0_%D0%BA%D0%B0%D1%80%D0%BE%D1%82%D0%B8%D0%BD" title="Бета каротин – Mongolian" lang="mn" hreflang="mn" data-title="Бета каротин" data-language-autonym="Монгол" data-language-local-name="Mongolian" class="interlanguage-link-target"><span>Монгол</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/B%C3%A8tacaroteen" title="Bètacaroteen – Dutch" lang="nl" hreflang="nl" data-title="Bètacaroteen" 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/%CE%92-%E3%82%AB%E3%83%AD%E3%83%86%E3%83%B3" title="Β-カロテン – Japanese" lang="ja" hreflang="ja" data-title="Β-カロテン" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/%CE%92-Karoten" title="Β-Karoten – Polish" lang="pl" hreflang="pl" data-title="Β-Karoten" 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/Betacaroteno" title="Betacaroteno – Portuguese" lang="pt" hreflang="pt" data-title="Betacaroteno" 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/Beta-caroten" title="Beta-caroten – Romanian" lang="ro" hreflang="ro" data-title="Beta-caroten" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Betakarot%C3%A9n" title="Betakarotén – Slovak" lang="sk" hreflang="sk" data-title="Betakarotén" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Beta-karoten" title="Beta-karoten – Serbian" lang="sr" hreflang="sr" data-title="Beta-karoten" 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/Beta-karoten" title="Beta-karoten – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Beta-karoten" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Beetakaroteeni" title="Beetakaroteeni – Finnish" lang="fi" hreflang="fi" data-title="Beetakaroteeni" 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/Betakaroten" title="Betakaroten – Swedish" lang="sv" 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data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">Not to be confused with <a href="/wiki/Beta-keratin" title="Beta-keratin">beta-keratin</a>.</div> <p class="mw-empty-elt"> </p> <style data-mw-deduplicate="TemplateStyles:r1084375498">.mw-parser-output .ib-chembox{border-collapse:collapse;text-align:left}.mw-parser-output .ib-chembox td,.mw-parser-output .ib-chembox th{border:1px solid #a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}</style> <table class="infobox ib-chembox"> <caption>β-Carotene </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Beta-Carotin.svg" class="mw-file-description"><img alt="Skeletal formula" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/27/Beta-Carotin.svg/250px-Beta-Carotin.svg.png" decoding="async" width="250" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/27/Beta-Carotin.svg/375px-Beta-Carotin.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/27/Beta-Carotin.svg/500px-Beta-Carotin.svg.png 2x" data-file-width="1000" data-file-height="200" /></a></span><br /><div style="text-align:center;"><a href="/wiki/Skeletal_formula" title="Skeletal formula">Skeletal formula</a></div> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Beta-carotene-from-xtal-3D-bs-17.png" class="mw-file-description"><img alt="Ball-and-stick model" src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f3/Beta-carotene-from-xtal-3D-bs-17.png/250px-Beta-carotene-from-xtal-3D-bs-17.png" decoding="async" width="250" height="80" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f3/Beta-carotene-from-xtal-3D-bs-17.png/375px-Beta-carotene-from-xtal-3D-bs-17.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f3/Beta-carotene-from-xtal-3D-bs-17.png/500px-Beta-carotene-from-xtal-3D-bs-17.png 2x" data-file-width="3000" data-file-height="956" /></a></span><br /><div style="text-align:center;"><a href="/wiki/Ball-and-stick_model" title="Ball-and-stick model">Ball-and-stick model</a><sup id="cite_ref-Hursthouse_1-0" class="reference"><a href="#cite_note-Hursthouse-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Senge_2-0" class="reference"><a href="#cite_note-Senge-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup></div> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Beta-carotene-from-xtal-3D-sf.png" class="mw-file-description"><img alt="Space-filling model" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/69/Beta-carotene-from-xtal-3D-sf.png/250px-Beta-carotene-from-xtal-3D-sf.png" decoding="async" width="250" height="90" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/69/Beta-carotene-from-xtal-3D-sf.png/375px-Beta-carotene-from-xtal-3D-sf.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/69/Beta-carotene-from-xtal-3D-sf.png/500px-Beta-carotene-from-xtal-3D-sf.png 2x" data-file-width="3000" data-file-height="1080" /></a></span><br /><div style="text-align:center;"><a href="/wiki/Space-filling_model" title="Space-filling model">Space-filling model</a><sup id="cite_ref-Hursthouse_1-1" class="reference"><a href="#cite_note-Hursthouse-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Senge_2-1" class="reference"><a href="#cite_note-Senge-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup></div> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:%CE%92-Carotene_powder.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/bd/%CE%92-Carotene_powder.jpg/250px-%CE%92-Carotene_powder.jpg" decoding="async" width="250" height="188" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/bd/%CE%92-Carotene_powder.jpg/375px-%CE%92-Carotene_powder.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/bd/%CE%92-Carotene_powder.jpg/500px-%CE%92-Carotene_powder.jpg 2x" data-file-width="4032" data-file-height="3024" /></a></span> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Chemical_nomenclature" title="Chemical nomenclature">IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">β,β-Carotene</div> </td></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Chemical_nomenclature#Systematic_name" title="Chemical nomenclature">Systematic IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;">1,1′-[(1<i>E</i>,3<i>E</i>,5<i>E</i>,7<i>E</i>,9<i>E</i>,11<i>E</i>,13<i>E</i>,15<i>E</i>,17<i>E</i>)-3,7,12,16-Tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaene-1,18-diyl]bis(2,6,6-trimethylcyclohex-1-ene)</div></div> </td></tr> <tr> <td colspan="2" style="text-align:left;">Other names <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">Betacarotene <small>(<a href="/wiki/International_nonproprietary_name" title="International nonproprietary name">INN</a>)</small>, β-Carotene,<sup id="cite_ref-Scifinder_3-0" class="reference"><a href="#cite_note-Scifinder-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> Food Orange 5, Provitamin A</div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=7235-40-7">7235-40-7</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=CC2%28C%29CCCC%28%5CC%29%3DC2%5CC%3DC%5CC%28%5CC%29%3DC%5CC%3DC%5CC%28%5CC%29%3DC%5CC%3DC%5CC%3DC%28%2FC%29%5CC%3DC%5CC%3DC%28%2FC%29%5CC%3DC%5CC1%3DC%28%2FC%29CCCC1%28C%29C">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td>3DMet </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.3dmet.dna.affrc.go.jp"><a rel="nofollow" class="external text" href="http://www.3dmet.dna.affrc.go.jp/cgi/show_data.php?acc=B00389">B00389</a></span></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Beilstein_database" title="Beilstein database">Beilstein Reference</a></div> </td> <td>1917416 </td></tr> <tr> <td><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=17579">CHEBI:17579</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembldb/index.php/compound/inspect/ChEMBL1293">ChEMBL1293</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.4444129.html">4444129</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a> </td> <td><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.027.851">100.027.851</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q306135#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span> </td></tr> <tr> <td><a href="/wiki/European_Community_number" title="European Community number"><span title="European Community number (chemical identifier)">EC Number</span></a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>230-636-6</li></ul></div> </td></tr> <tr> <td><a href="/wiki/E_number" title="E number"><span title="E number (food additive code)">E number</span></a> </td> <td>E160a <a href="/wiki/E_number#E100–E199" title="E number">(colours)</a> </td></tr> <tr> <td><a href="/wiki/KEGG" title="KEGG">KEGG</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.kegg.jp"><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/C02094">C02094</a></span></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/5280489">5280489</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/01YAE03M7J">01YAE03M7J</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID3020253">DTXSID3020253</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q306135#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></span></li></ul></div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/C40H56/c1-31(19-13-21-33(3)25-27-37-35(5)23-15-29-39(37,7)8) 17-11-12-18-32(2)20-14-22-34(4)26-28-38-36(6)24-16-30-40(38,9) 10/h11-14,17-22,25-28H,15-16,23-24,29-30H2,1-10H3<sup> <span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup></div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: OENHQHLEOONYIE-UHFFFAOYSA-N<sup> <span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup></div></div></li></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">CC2(C)CCCC(\C)=C2\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(/C)CCCC1(C)C</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td><span title="Carbon">C</span><sub>40</sub><span title="Hydrogen">H</span><sub>56</sub> </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td><span class="nowrap"><span data-sort-value="7002536888000000000♠"></span>536.888</span> g·mol<sup>−1</sup>   </td></tr> <tr> <td>Appearance </td> <td>Dark orange crystals </td></tr> <tr> <td><a href="/wiki/Density" title="Density">Density</a> </td> <td>1.00 g/cm<sup>3</sup><sup id="cite_ref-r1_4-0" class="reference"><a href="#cite_note-r1-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>183 °C (361 °F; 456 K)<sup id="cite_ref-r1_4-1" class="reference"><a href="#cite_note-r1-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> <br /> decomposes<sup id="cite_ref-sigma_6-0" class="reference"><a href="#cite_note-sigma-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Boiling_point" title="Boiling point">Boiling point</a> </td> <td>654.7 °C (1,210.5 °F; 927.9 K) <br /> at 760 mmHg (101324 Pa) </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Aqueous_solution" title="Aqueous solution">Solubility in water</a></div> </td> <td>Insoluble </td></tr> <tr> <td><a href="/wiki/Solubility" title="Solubility">Solubility</a> </td> <td>Soluble in <a href="/wiki/Carbon_disulfide" title="Carbon disulfide">CS<sub>2</sub></a>, <a href="/wiki/Benzene" title="Benzene">benzene</a>, <a href="/wiki/Chloroform" title="Chloroform">CHCl<sub>3</sub></a>, <a href="/wiki/Ethanol" title="Ethanol">ethanol</a><br /> Insoluble in <a href="/wiki/Glycerin" class="mw-redirect" title="Glycerin">glycerin</a> </td></tr> <tr> <td><a href="/wiki/Solubility" title="Solubility">Solubility</a> in <a href="/wiki/Dichloromethane" title="Dichloromethane">dichloromethane</a> </td> <td>4.51 g/kg (20 °C)<sup id="cite_ref-pubchem_5-0" class="reference"><a href="#cite_note-pubchem-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> = 5.98 g/L (given BCM density of 1.3266 g/cm<sup>3</sup> at 20°C) </td></tr> <tr> <td><a href="/wiki/Solubility" title="Solubility">Solubility</a> in <a href="/wiki/Hexane" title="Hexane">hexane</a> </td> <td>0.1 g/L </td></tr> <tr> <td><a href="/wiki/Partition_coefficient" title="Partition coefficient">log <i>P</i></a> </td> <td>14.764 </td></tr> <tr> <td><a href="/wiki/Vapor_pressure" title="Vapor pressure">Vapor pressure</a> </td> <td>2.71·10<sup>−16</sup> mmHg </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Refractive_index" title="Refractive index">Refractive index</a> (<i>n</i><sub>D</sub>)</div> </td> <td>1.565 </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Pharmacology </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Anatomical_Therapeutic_Chemical_Classification_System" title="Anatomical Therapeutic Chemical Classification System">ATC code</a></div> </td> <td><a href="/wiki/ATC_code_A11" title="ATC code A11">A11CA02</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=A11CA02">WHO</a></span>) <a href="/wiki/ATC_code_D02" title="ATC code D02">D02BB01</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=D02BB01">WHO</a></span>) </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Hazards </th></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;"><a href="/wiki/Globally_Harmonized_System_of_Classification_and_Labelling_of_Chemicals" title="Globally Harmonized System of Classification and Labelling of Chemicals"><b>GHS</b> labelling</a>: </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_hazard_pictograms" title="GHS hazard pictograms">Pictograms</a></div> </td> <td><span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-exclam.svg" class="mw-file-description" title="GHS07: Exclamation mark"><img alt="GHS07: Exclamation mark" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/50px-GHS-pictogram-exclam.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/75px-GHS-pictogram-exclam.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/100px-GHS-pictogram-exclam.svg.png 2x" data-file-width="512" data-file-height="512" /></a></span> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Globally_Harmonized_System_of_Classification_and_Labelling_of_Chemicals#Signal_word" title="Globally Harmonized System of Classification and Labelling of Chemicals">Signal word</a></div> </td> <td><b>Warning</b> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_hazard_statements" title="GHS hazard statements">Hazard statements</a></div> </td> <td><abbr class="abbr" title="H315: Causes skin irritation">H315</abbr>, <abbr class="abbr" title="H319: Causes serious eye irritation">H319</abbr>, <abbr class="abbr" title="H412: Harmful to aquatic life with long lasting effects">H412</abbr> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_precautionary_statements" title="GHS precautionary statements">Precautionary statements</a></div> </td> <td><abbr class="abbr" title="P264: Wash ... thoroughly after handling.">P264</abbr>, <abbr class="abbr" title="P273: Avoid release to the environment.">P273</abbr>, <abbr class="abbr" title="P280: Wear protective gloves/protective clothing/eye protection/face protection.">P280</abbr>, <abbr class="abbr" title="P302+P352: IF ON SKIN: Wash with soap and water.">P302+P352</abbr>, <abbr class="abbr" title="P305+P351+P338: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do. Continue rinsing.">P305+P351+P338</abbr>, <abbr class="abbr" title="P321: Specific treatment (see ... on this label).">P321</abbr>, <abbr class="abbr" title="P332+P313: If skin irritation occurs: Get medical advice/attention.">P332+P313</abbr>, <abbr class="abbr" title="P337+P313: If eye irritation persists: Get medical advice/attention.">P337+P313</abbr>, <abbr class="abbr" title="P362: Take off contaminated clothing.">P362</abbr>, <abbr class="abbr" title="P501: Dispose of contents/container to ...">P501</abbr> </td></tr> <tr> <td><a href="/wiki/NFPA_704" title="NFPA 704"><b>NFPA 704</b></a> (fire diamond) </td> <td><style data-mw-deduplicate="TemplateStyles:r1170367383">.mw-parser-output .nfpa-704-diamond-ref{float:right;padding:1px;text-align:right}.mw-parser-output .nfpa-704-diamond-container{width:82px;font-family:sans-serif;margin:0 auto}.mw-parser-output .nfpa-704-diamond-container-ref{float:left;margin-left:1em}.mw-parser-output .nfpa-704-diamond-images{float:left;font-size:20px;text-align:center;position:relative;height:80px;width:80px;padding:1px}.mw-parser-output .nfpa-704-diamond-map{position:absolute;height:80px;width:80px}.mw-parser-output .nfpa-704-diamond .noresize{margin:0 auto}.mw-parser-output .nfpa-704-diamond-code{line-height:1em;text-align:center;position:absolute}.mw-parser-output .nfpa-704-diamond-code>a{color:black}.mw-parser-output .nfpa-704-diamond-blue{width:13px;top:31px;left:15px}.mw-parser-output .nfpa-704-diamond-red{width:12px;top:12px;left:35px}.mw-parser-output .nfpa-704-diamond-yellow{width:13px;top:31px;left:54px}.mw-parser-output .nfpa-704-diamond-white-image{position:relative;top:51px;left:0}.mw-parser-output .nfpa-704-diamond-white-text{vertical-align:middle;text-align:center;line-height:80%;position:absolute;top:52px}.mw-parser-output .nfpa-704-diamond-white-text a>span{position:absolute;color:black}.mw-parser-output .nfpa-704-diamond-white-wors{font-size:15px;width:23px;left:29px}.mw-parser-output .nfpa-704-diamond-white-wox{font-size:15px;font-stretch:condensed;width:21px;line-height:80%;top:-4px;left:29px}.mw-parser-output .nfpa-704-diamond-white-abcp{font-size:13.5px;font-stretch:condensed;width:28px;left:26px}.mw-parser-output .nfpa-704-diamond-white-ac{font-size:10px;width:30px;left:25px}.mw-parser-output .nfpa-704-diamond-white-strike{text-decoration:line-through}</style><div class="nfpa-704-diamond notheme"><div class="nfpa-704-diamond-container"><div class="nfpa-704-diamond-images nounderlines"> <div class="nfpa-704-diamond-map"><figure class="noresize" typeof="mw:File"><span><img alt="NFPA 704 four-colored diamond" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/80px-NFPA_704.svg.png" decoding="async" width="80" height="80" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/120px-NFPA_704.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/160px-NFPA_704.svg.png 2x" data-file-width="512" data-file-height="512" usemap="#ImageMap_3d8171e88c0df7b6" /></span><map name="ImageMap_3d8171e88c0df7b6"><area href="/wiki/NFPA_704#Blue" shape="poly" coords="23,23,47,47,23,70,0,47" alt="Health 0: Exposure under fire conditions would offer no hazard beyond that of ordinary combustible material. E.g. sodium chloride" title="Health 0: Exposure under fire conditions would offer no hazard beyond that of ordinary combustible material. E.g. sodium chloride" /><area href="/wiki/NFPA_704#Red" shape="poly" coords="47,0,70,23,47,47,23,23" alt="Flammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oil" title="Flammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oil" /><area href="/wiki/NFPA_704#Yellow" shape="poly" coords="70,23,94,47,70,70,47,47" alt="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" title="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" /><area href="/wiki/NFPA_704#White" shape="poly" coords="47,47,70,70,47,94,23,70" alt="Special hazards (white): no code" title="Special hazards (white): no code" /></map><figcaption></figcaption></figure></div><div class="nfpa-704-diamond-code nfpa-704-diamond-blue"> <a href="/wiki/NFPA_704#Blue" title="NFPA 704"><span title="Health 0: Exposure under fire conditions would offer no hazard beyond that of ordinary combustible material. E.g. sodium chloride" class="notheme mw-no-invert">0</span></a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-red"> <a href="/wiki/NFPA_704#Red" title="NFPA 704"><span title="Flammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oil" class="notheme mw-no-invert">1</span></a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-yellow"> <a href="/wiki/NFPA_704#Yellow" title="NFPA 704"><span title="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" class="notheme mw-no-invert">0</span></a></div></div></div></div> </td></tr> <tr> <td><a href="/wiki/Flash_point" title="Flash point">Flash point</a> </td> <td>103 °C (217 °F; 376 K)<sup id="cite_ref-sigma_6-1" class="reference"><a href="#cite_note-sigma-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"><div style="text-align:center;"><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/12px-X_mark.svg.png" decoding="async" width="12" height="14" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/18px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/24px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span> <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=458441983&page2=%CE%92-Carotene">verify</a></span> (<a href="/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validation" title="Wikipedia:WikiProject Chemicals/Chembox validation">what is</a> <sup><span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup> ?) </div></div> <div style="margin-top: 0.3em; text-align: center;"><a href="/wiki/Wikipedia:Chemical_infobox#References" title="Wikipedia:Chemical infobox">Infobox references</a></div> </td></tr> </tbody></table><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound</div> <p><b>β-Carotene</b> (<i>beta</i>-carotene) is an <a href="/wiki/Organic_compound" title="Organic compound">organic</a>, strongly colored red-orange <a href="/wiki/Pigment" title="Pigment">pigment</a> abundant in fungi,<sup id="cite_ref-:0_7-0" class="reference"><a href="#cite_note-:0-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> plants, and fruits. It is a member of the <a href="/wiki/Carotene" title="Carotene">carotenes</a>, which are <a href="/wiki/Terpenoid" title="Terpenoid">terpenoids</a> (isoprenoids), synthesized biochemically from eight <a href="/wiki/Isoprene" title="Isoprene">isoprene</a> units and thus having 40 <a href="/wiki/Carbon" title="Carbon">carbons</a>. </p><p>Dietary β-carotene is a pro<a href="/wiki/Vitamin_A" title="Vitamin A">vitamin A</a> compound, converting in the body to <a href="/wiki/Retinol" title="Retinol">retinol</a> (vitamin A).<sup id="cite_ref-lpi_8-0" class="reference"><a href="#cite_note-lpi-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> In foods, it has rich content in <a href="/wiki/Carrot" title="Carrot">carrots</a>, <a href="/wiki/Pumpkin" title="Pumpkin">pumpkin</a>, <a href="/wiki/Spinach" title="Spinach">spinach</a>, and <a href="/wiki/Sweet_potato" title="Sweet potato">sweet potato</a>.<sup id="cite_ref-lpi_8-1" class="reference"><a href="#cite_note-lpi-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> It is used as a <a href="/wiki/Dietary_supplement" title="Dietary supplement">dietary supplement</a> and may be prescribed to treat <a href="/wiki/Erythropoietic_protoporphyria" title="Erythropoietic protoporphyria">erythropoietic protoporphyria</a>, an inherited condition of sunlight sensitivity.<sup id="cite_ref-mlp_9-0" class="reference"><a href="#cite_note-mlp-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p><p>β-carotene is the most common carotenoid in plants.<sup id="cite_ref-lpi_8-2" class="reference"><a href="#cite_note-lpi-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> When used as a <a href="/wiki/Food_coloring" title="Food coloring">food coloring</a>, it has the <a href="/wiki/E_number" title="E number">E number</a> E160a.<sup id="cite_ref-isbn0-471-73518-3_10-0" class="reference"><a href="#cite_note-isbn0-471-73518-3-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup><sup class="reference nowrap"><span title="Page / location: 119">: 119 </span></sup> The structure was deduced in 1930.<sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p><p>Isolation of β-carotene from fruits abundant in carotenoids is commonly done using column <a href="/wiki/Chromatography" title="Chromatography">chromatography</a>. It is industrially extracted from richer sources such as the algae <i><a href="/wiki/Dunaliella_salina" title="Dunaliella salina">Dunaliella salina</a></i>.<sup id="cite_ref-us4439629_12-0" class="reference"><a href="#cite_note-us4439629-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> The separation of β-carotene from the mixture of other carotenoids is based on the polarity of a compound. β-Carotene is a non-polar compound, so it is separated with a non-polar solvent such as <a href="/wiki/Hexane" title="Hexane">hexane</a>.<sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> Being highly <a href="/wiki/Conjugated_system" title="Conjugated system">conjugated</a>, it is deeply colored, and as a <a href="/wiki/Hydrocarbon" title="Hydrocarbon">hydrocarbon</a> lacking functional groups, it is <a href="/wiki/Lipophilic" class="mw-redirect" title="Lipophilic">lipophilic</a>. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Provitamin_A_activity">Provitamin A activity</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%CE%92-Carotene&action=edit&section=1" title="Edit section: Provitamin A activity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Plant carotenoids are the primary dietary source of <a href="/wiki/Provitamin" title="Provitamin">provitamin</a> A worldwide, with β-carotene as the best-known provitamin A carotenoid.<sup id="cite_ref-lpi_8-3" class="reference"><a href="#cite_note-lpi-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> Others include <a href="/wiki/Alpha-Carotene" class="mw-redirect" title="Alpha-Carotene">α-carotene</a> and <a href="/wiki/Cryptoxanthin" class="mw-redirect" title="Cryptoxanthin">β-cryptoxanthin</a>.<sup id="cite_ref-lpi_8-4" class="reference"><a href="#cite_note-lpi-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> Carotenoid absorption is restricted to the <a href="/wiki/Duodenum" title="Duodenum">duodenum</a> of the <a href="/wiki/Small_intestine" title="Small intestine">small intestine</a>. One molecule of β-carotene can be cleaved by the intestinal enzyme <i>β,β-carotene 15,15'-monooxygenase</i> into two molecules of vitamin A.<sup id="cite_ref-lpi_8-5" class="reference"><a href="#cite_note-lpi-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Absorption,_metabolism_and_excretion"><span id="Absorption.2C_metabolism_and_excretion"></span>Absorption, metabolism and excretion</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%CE%92-Carotene&action=edit&section=2" title="Edit section: Absorption, metabolism and excretion"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>As part of the digestive process, food-sourced carotenoids must be separated from plant cells and incorporated into lipid-containing micelles to be bioaccessible to intestinal <a href="/wiki/Enterocytes" class="mw-redirect" title="Enterocytes">enterocytes</a>.<sup id="cite_ref-lpi_8-6" class="reference"><a href="#cite_note-lpi-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> If already extracted (or synthetic) and then presented in an oil-filled dietary supplement capsule, there is greater bioavailability compared to that from foods.<sup id="cite_ref-PKIN2020Carotenoids_16-0" class="reference"><a href="#cite_note-PKIN2020Carotenoids-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p><p>At the enterocyte cell wall, β-carotene is taken up by the membrane transporter protein scavenger receptor class B, type 1 (SCARB1). Absorbed β-carotene is then either incorporated as such into <a href="/wiki/Chylomicron" title="Chylomicron">chylomicrons</a> or first converted to retinal and then retinol, bound to <a href="/wiki/RBP2" title="RBP2">retinol binding protein 2</a>, before being incorporated into chylomicrons.<sup id="cite_ref-lpi_8-7" class="reference"><a href="#cite_note-lpi-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> The conversion process consists of one molecule of β-carotene cleaved by the enzyme <a href="/wiki/Beta-carotene_15,15%27-dioxygenase" title="Beta-carotene 15,15'-dioxygenase">beta-carotene 15,15'-dioxygenase</a>, which is encoded by the BCO1 gene, into two molecules of retinal.<sup id="cite_ref-lpi_8-8" class="reference"><a href="#cite_note-lpi-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> When plasma retinol is in the normal range the gene expression for SCARB1 and BCO1 are suppressed, creating a feedback loop that suppresses β-carotene absorption and conversion.<sup id="cite_ref-PKIN2020Carotenoids_16-1" class="reference"><a href="#cite_note-PKIN2020Carotenoids-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p><p>The majority of chylomicrons are taken up by the liver, then secreted into the blood repackaged into <a href="/wiki/Low_density_lipoprotein" class="mw-redirect" title="Low density lipoprotein">low density lipoproteins</a> (LDLs).<sup id="cite_ref-lpi_8-9" class="reference"><a href="#cite_note-lpi-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> From these circulating lipoproteins and the chylomicrons that bypassed the liver, β-carotene is taken into cells via receptor SCARB1. Human tissues differ in expression of SCARB1, and hence β-carotene content. Examples expressed as ng/g, wet weight: liver=479, lung=226, prostate=163 and skin=26.<sup id="cite_ref-PKIN2020Carotenoids_16-2" class="reference"><a href="#cite_note-PKIN2020Carotenoids-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p><p>Once taken up by peripheral tissue cells, the major usage of absorbed β-carotene is as a precursor to retinal via symmetric cleavage by the enzyme beta-carotene 15,15'-dioxygenase, which is encoded by the BCO1 gene.<sup id="cite_ref-lpi_8-10" class="reference"><a href="#cite_note-lpi-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> A lesser amount is metabolized by the mitochondrial enzyme beta-carotene 9',10'-dioxygenase, which is encoded by the BCO2 gene. The products of this asymmetric cleavage are two <a href="/wiki/Beta-ionone" class="mw-redirect" title="Beta-ionone">beta-ionone</a> molecules and rosafluene. BCO2 appears to be involved in preventing excessive accumulation of carotenoids; a BCO2 defect in chickens results in yellow skin color due to accumulation in subcutaneous fat.<sup id="cite_ref-Babino2015_17-0" class="reference"><a href="#cite_note-Babino2015-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Wu2016_18-0" class="reference"><a href="#cite_note-Wu2016-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Conversion_factors">Conversion factors</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%CE%92-Carotene&action=edit&section=3" title="Edit section: Conversion factors"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>For counting dietary vitamin A intake, β-carotene may be converted either using the newer retinol activity equivalents (RAE) or the older international unit (IU).<sup id="cite_ref-lpi_8-11" class="reference"><a href="#cite_note-lpi-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Retinol_activity_equivalents_(RAEs)"><span id="Retinol_activity_equivalents_.28RAEs.29"></span>Retinol activity equivalents (RAEs)</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%CE%92-Carotene&action=edit&section=4" title="Edit section: Retinol activity equivalents (RAEs)"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Since 2001, the US Institute of Medicine uses retinol activity equivalents (RAE) for their Dietary Reference Intakes, defined as follows:<sup id="cite_ref-lpi_8-12" class="reference"><a href="#cite_note-lpi-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-DRI_A_19-0" class="reference"><a href="#cite_note-DRI_A-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> </p> <ul><li>1 μg RAE = 1 μg retinol from food or supplements</li> <li>1 μg RAE = 2 μg all-<i>trans</i>-β-carotene from supplements</li> <li>1 μg RAE = 12 μg of all-<i>trans</i>-β-carotene from food</li> <li>1 μg RAE = 24 μg α-carotene or β-cryptoxanthin from food</li></ul> <p>RAE takes into account carotenoids' variable absorption and conversion to vitamin A by humans better than and replaces the older retinol equivalent (RE) (1 μg RE = 1 μg retinol, 6 μg β-carotene, or 12 μg α-carotene or β-cryptoxanthin).<sup id="cite_ref-DRI_A_19-1" class="reference"><a href="#cite_note-DRI_A-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> RE was developed 1967 by the United Nations/<a href="/wiki/World_Health_Organization" title="World Health Organization">World Health Organization</a> Food and Agriculture Organization (FAO/WHO).<sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="International_Units">International Units</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%CE%92-Carotene&action=edit&section=5" title="Edit section: International Units"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Another older unit of vitamin A activity is the international unit (IU).<sup id="cite_ref-lpi_8-13" class="reference"><a href="#cite_note-lpi-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> Like retinol equivalent, the international unit does not take into account carotenoid variable absorption and conversion to vitamin A by humans, as well as the more modern retinol activity equivalent. Unfortunately, food and supplement labels still generally use IU, but IU can be converted to the more useful retinol activity equivalent as follows:<sup id="cite_ref-DRI_A_19-2" class="reference"><a href="#cite_note-DRI_A-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> </p> <ul><li>1 μg RAE = 3.33 IU retinol</li> <li>1 IU retinol = 0.3 μg RAE</li> <li>1 IU β-carotene from supplements = 0.3 μg RAE</li> <li>1 IU β-carotene from food = 0.05 μg RAE</li> <li>1 IU α-carotene or β-cryptoxanthin from food = 0.025 μg RAE1</li></ul> <div class="mw-heading mw-heading2"><h2 id="Dietary_sources">Dietary sources</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%CE%92-Carotene&action=edit&section=6" title="Edit section: Dietary sources"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The average daily intake of β-carotene is in the range 2–7 mg, as estimated from a pooled analysis of 500,000 women living in the US, Canada, and some European countries.<sup id="cite_ref-21" class="reference"><a href="#cite_note-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> Beta-carotene is found in many foods and is sold as a <a href="/wiki/Dietary_supplement" title="Dietary supplement">dietary supplement</a>.<sup id="cite_ref-lpi_8-14" class="reference"><a href="#cite_note-lpi-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> β-Carotene contributes to the orange color of many different fruits and vegetables. <a href="/wiki/Vietnam" title="Vietnam">Vietnamese</a> <a href="/wiki/Gac" title="Gac">gac</a> (<i>Momordica cochinchinensis</i> Spreng.) and crude <a href="/wiki/Palm_oil" title="Palm oil">palm oil</a> are particularly rich sources, as are yellow and orange fruits, such as <a href="/wiki/Cantaloupe" title="Cantaloupe">cantaloupe</a>, <a href="/wiki/Mangoes" class="mw-redirect" title="Mangoes">mangoes</a>, <a href="/wiki/Pumpkin" title="Pumpkin">pumpkin</a>, and <a href="/wiki/Papayas" class="mw-redirect" title="Papayas">papayas</a>, and orange <a href="/wiki/Root_vegetables" class="mw-redirect" title="Root vegetables">root vegetables</a> such as <a href="/wiki/Carrots" class="mw-redirect" title="Carrots">carrots</a> and <a href="/wiki/Sweet_potato" title="Sweet potato">sweet potatoes</a>.<sup id="cite_ref-lpi_8-15" class="reference"><a href="#cite_note-lpi-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p><p>The color of β-carotene is masked by <a href="/wiki/Chlorophyll" title="Chlorophyll">chlorophyll</a> in green <a href="/wiki/Leaf_vegetable" title="Leaf vegetable">leaf vegetables</a> such as <a href="/wiki/Spinach" title="Spinach">spinach</a>, <a href="/wiki/Kale" title="Kale">kale</a>, sweet potato leaves, and sweet <a href="/wiki/Gourd" title="Gourd">gourd</a> leaves.<sup id="cite_ref-lpi_8-16" class="reference"><a href="#cite_note-lpi-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-22" class="reference"><a href="#cite_note-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> </p><p>The U.S. Department of Agriculture lists foods high in β-carotene content:<sup id="cite_ref-23" class="reference"><a href="#cite_note-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> </p> <table class="wikitable" style="float:right; clear:right; width:18em; text-align:center;"> <tbody><tr> <th>Food </th> <th>Beta-carotene <p>Milligrams per 100 g </p> </th></tr> <tr> <td><a href="/wiki/Sweet_potato" title="Sweet potato">Sweet potato</a>, skinned, boiled </td> <td>9.4 </td></tr> <tr> <td><a href="/wiki/Carrot" title="Carrot">Carrot</a> juice </td> <td>9.3 </td></tr> <tr> <td>Carrots, raw or boiled </td> <td>9.2 </td></tr> <tr> <td><a href="/wiki/Kale" title="Kale">Kale</a>, boiled </td> <td>8.8 </td></tr> <tr> <td><a href="/wiki/Pumpkin" title="Pumpkin">Pumpkin</a>, canned </td> <td>6.9 </td></tr> <tr> <td><a href="/wiki/Spinach" title="Spinach">Spinach</a>, canned </td> <td>5.9 </td></tr> </tbody></table> <div class="mw-heading mw-heading3"><h3 id="No_dietary_requirement">No dietary requirement</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%CE%92-Carotene&action=edit&section=7" title="Edit section: No dietary requirement"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Government and non-government organizations have not set a dietary requirement for β-carotene.<sup id="cite_ref-PKIN2020Carotenoids_16-3" class="reference"><a href="#cite_note-PKIN2020Carotenoids-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Side_effects">Side effects</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%CE%92-Carotene&action=edit&section=8" title="Edit section: Side effects"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Excess β-carotene is predominantly stored in the fat tissues of the body.<sup id="cite_ref-lpi_8-17" class="reference"><a href="#cite_note-lpi-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> The most common side effect of excessive β-carotene consumption is <a href="/wiki/Carotenodermia" class="mw-redirect" title="Carotenodermia">carotenodermia</a>, a physically harmless condition that presents as a conspicuous <a href="/wiki/Orange_(colour)" title="Orange (colour)">orange</a> <a href="/wiki/Skin" title="Skin">skin</a> tint arising from deposition of the carotenoid in the outermost layer of the <a href="/wiki/Epidermis_(skin)" class="mw-redirect" title="Epidermis (skin)">epidermis</a>.<sup id="cite_ref-lpi_8-18" class="reference"><a href="#cite_note-lpi-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-mlp_9-1" class="reference"><a href="#cite_note-mlp-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-PKIN2020Carotenoids_16-4" class="reference"><a href="#cite_note-PKIN2020Carotenoids-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-PKIN2020VitA_24-0" class="reference"><a href="#cite_note-PKIN2020VitA-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Carotenosis">Carotenosis</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%CE%92-Carotene&action=edit&section=9" title="Edit section: Carotenosis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Carotenosis" title="Carotenosis">Carotenoderma</a>, also referred to as carotenemia, is a benign and reversible medical condition where an excess of dietary carotenoids results in orange discoloration of the outermost skin layer.<sup id="cite_ref-lpi_8-19" class="reference"><a href="#cite_note-lpi-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> It is associated with a high blood β-carotene value. This can occur after a month or two of consumption of beta-carotene rich foods, such as carrots, carrot juice, tangerine juice, mangos, or in Africa, red palm oil. β-carotene dietary supplements can have the same effect. The discoloration extends to palms and soles of feet, but not to the <a href="/wiki/Sclera" title="Sclera">white of the eye</a>, which helps distinguish the condition from <a href="/wiki/Jaundice" title="Jaundice">jaundice</a>. Carotenodermia is reversible upon cessation of excessive intake.<sup id="cite_ref-25" class="reference"><a href="#cite_note-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> Consumption of greater than 30 mg/day for a prolonged period has been confirmed as leading to carotenemia.<sup id="cite_ref-PKIN2020Carotenoids_16-5" class="reference"><a href="#cite_note-PKIN2020Carotenoids-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-26" class="reference"><a href="#cite_note-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="No_risk_for_hypervitaminosis_A">No risk for hypervitaminosis A</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%CE%92-Carotene&action=edit&section=10" title="Edit section: No risk for hypervitaminosis A"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>At the <a href="/wiki/Enterocyte" title="Enterocyte">enterocyte</a> cell wall, β-carotene is taken up by the membrane transporter protein scavenger receptor class B, type 1 (SCARB1). Absorbed β-carotene is then either incorporated as such into chylomicrons or first converted to retinal and then retinol, bound to <a href="/wiki/RBP2" title="RBP2">retinol binding protein 2</a>, before being incorporated into chylomicrons. The conversion process consists of one molecule of β-carotene cleaved by the enzyme <a href="/wiki/Beta-carotene_15,15%27-dioxygenase" title="Beta-carotene 15,15'-dioxygenase">beta-carotene 15,15'-dioxygenase</a>, which is encoded by the BCO1 gene, into two molecules of retinal. When plasma retinol is in the normal range the gene expression for SCARB1 and BCO1 are suppressed, creating a feedback loop that suppresses absorption and conversion. Because of these two mechanisms, high intake will not lead to <a href="/wiki/Hypervitaminosis_A" title="Hypervitaminosis A">hypervitaminosis A</a>.<sup id="cite_ref-PKIN2020Carotenoids_16-6" class="reference"><a href="#cite_note-PKIN2020Carotenoids-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Drug_interactions">Drug interactions</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%CE%92-Carotene&action=edit&section=11" title="Edit section: Drug interactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>β-Carotene can interact with medication used for lowering <a href="/wiki/Cholesterol" title="Cholesterol">cholesterol</a>.<sup id="cite_ref-lpi_8-20" class="reference"><a href="#cite_note-lpi-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> Taking them together can lower the effectiveness of these medications and is considered only a moderate interaction.<sup id="cite_ref-lpi_8-21" class="reference"><a href="#cite_note-lpi-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Bile_acid_sequestrant" title="Bile acid sequestrant">Bile acid sequestrants</a> and <a href="/wiki/Proton-pump_inhibitor" title="Proton-pump inhibitor">proton-pump inhibitors</a> can decrease absorption of β-carotene.<sup id="cite_ref-27" class="reference"><a href="#cite_note-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> Consuming alcohol with β-carotene can decrease its ability to convert to retinol and could possibly result in <a href="/wiki/Hepatotoxicity" title="Hepatotoxicity">hepatotoxicity</a>.<sup id="cite_ref-28" class="reference"><a href="#cite_note-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="β-Carotene_and_lung_cancer_in_smokers"><span id=".CE.B2-Carotene_and_lung_cancer_in_smokers"></span>β-Carotene and lung cancer in smokers</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%CE%92-Carotene&action=edit&section=12" title="Edit section: β-Carotene and lung cancer in smokers"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Chronic high doses of β-carotene supplementation increases the probability of lung cancer in <a href="/wiki/Health_effects_of_tobacco" title="Health effects of tobacco">smokers</a><sup id="cite_ref-lpi_8-22" class="reference"><a href="#cite_note-lpi-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-29" class="reference"><a href="#cite_note-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> while its natural vitamer, retinol, increases lung cancer in smokers and nonsmokers. The effect is specific to supplementation dose as no <a href="/wiki/Lung" title="Lung">lung</a> damage has been detected in those who are exposed to cigarette smoke and who ingest a physiological dose of β-carotene (6 mg), in contrast to high pharmacological dose (30 mg).<sup id="cite_ref-lpi_8-23" class="reference"><a href="#cite_note-lpi-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-30" class="reference"><a href="#cite_note-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup>. </p><p>Increases in lung cancer have been attributed to the tendency of β-carotene to oxidize,<sup id="cite_ref-31" class="reference"><a href="#cite_note-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> yet based on the pharmacokinetics of β-carotene absorption and transport through the intestine and the lack of specific β-carotene transporters, it is unlikely that β-carotene reaches the lung of smokers in sufficient quantities.<sup id="cite_ref-32" class="reference"><a href="#cite_note-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> Additional research is required to understand the link between the increased risk of cancer and all-cause mortality following β-carotene supplementation. </p><p>Additionally, supplemental, high-dose β-carotene may increase the risk of <a href="/wiki/Prostate_cancer" title="Prostate cancer">prostate cancer</a>, <a href="/wiki/Intracerebral_hemorrhage" title="Intracerebral hemorrhage">intracerebral hemorrhage</a>, and cardiovascular and total mortality irrespective of smoking status.<sup id="cite_ref-lpi_8-24" class="reference"><a href="#cite_note-lpi-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-mlp_9-2" class="reference"><a href="#cite_note-mlp-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Industrial_sources">Industrial sources</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%CE%92-Carotene&action=edit&section=13" title="Edit section: Industrial sources"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>β-carotene is industrially made either by total synthesis (see <a href="/wiki/Retinol#Industrial_synthesis" title="Retinol">Retinol § Industrial synthesis</a>) or by extraction from biological sources such as vegetables, microalgae (especially <i>Dunaliella salina</i>), and genetically-engineered microbes. The synthetic path is low-cost and high-yield.<sup id="cite_ref-singh_33-0" class="reference"><a href="#cite_note-singh-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Research">Research</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%CE%92-Carotene&action=edit&section=14" title="Edit section: Research"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Medical authorities generally recommend obtaining beta-carotene from food rather than dietary supplements.<sup id="cite_ref-lpi_8-25" class="reference"><a href="#cite_note-lpi-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> A 2013 meta-analysis of <a href="/wiki/Randomized_controlled_trial" title="Randomized controlled trial">randomized controlled trials</a> concluded that high-dosage (≥9.6 mg/day) beta-carotene supplementation is associated with a 6% increase in the risk of all-cause <a href="/wiki/Mortality_rate" title="Mortality rate">mortality</a>, while low-dosage (<9.6 mg/day) supplementation does not have a significant effect on mortality.<sup id="cite_ref-Bjelakovic2014_34-0" class="reference"><a href="#cite_note-Bjelakovic2014-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> Research is insufficient to determine whether a minimum level of beta-carotene consumption is necessary for human health and to identify what problems might arise from insufficient beta-carotene intake.<sup id="cite_ref-Impli_35-0" class="reference"><a href="#cite_note-Impli-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> However, a 2018 meta-analysis mostly of <a href="/wiki/Prospective_cohort_studies" class="mw-redirect" title="Prospective cohort studies">prospective cohort studies</a> found that both dietary and <a href="/wiki/Blood_test" title="Blood test">circulating</a> beta-carotene are associated with a lower risk of all-cause mortality. The highest circulating beta-carotene category, compared to the lowest, correlated with a 37% reduction in the risk of all-cause mortality, while the highest dietary beta-carotene intake category, compared to the lowest, was linked to an 18% decrease in the risk of all-cause mortality.<sup id="cite_ref-pmid30239557_36-0" class="reference"><a href="#cite_note-pmid30239557-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Macular_degeneration">Macular degeneration</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%CE%92-Carotene&action=edit&section=15" title="Edit section: Macular degeneration"><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/Macular_degeneration" title="Macular degeneration">Macular degeneration</a></div> <p>Age-related macular degeneration (AMD) represents the leading cause of irreversible blindness in elderly people. AMD is an oxidative stress, retinal disease that affects the macula, causing progressive loss of central vision.<sup id="cite_ref-DiCarlo2021_37-0" class="reference"><a href="#cite_note-DiCarlo2021-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup> β-carotene content is confirmed in human retinal pigment epithelium.<sup id="cite_ref-PKIN2020Carotenoids_16-7" class="reference"><a href="#cite_note-PKIN2020Carotenoids-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> Reviews reported mixed results for observational studies, with some reporting that diets higher in β-carotene correlated with a decreased risk of AMD whereas other studies reporting no benefits.<sup id="cite_ref-Gorus2017_38-0" class="reference"><a href="#cite_note-Gorus2017-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup> Reviews reported that for intervention trials using only β-carotene, there was no change to risk of developing AMD.<sup id="cite_ref-lpi_8-26" class="reference"><a href="#cite_note-lpi-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Gorus2017_38-1" class="reference"><a href="#cite_note-Gorus2017-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-39" class="reference"><a href="#cite_note-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Cancer">Cancer</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%CE%92-Carotene&action=edit&section=16" title="Edit section: Cancer"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>A meta-analysis concluded that supplementation with β-carotene does not appear to decrease the risk of cancer overall, nor specific cancers including: pancreatic, colorectal, prostate, breast, melanoma, or skin cancer generally.<sup id="cite_ref-lpi_8-27" class="reference"><a href="#cite_note-lpi-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Druesne2010_40-0" class="reference"><a href="#cite_note-Druesne2010-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup> High levels of β-carotene may increase the risk of lung cancer in current and former smokers.<sup id="cite_ref-lpi_8-28" class="reference"><a href="#cite_note-lpi-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-41" class="reference"><a href="#cite_note-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> Results are not clear for thyroid cancer.<sup id="cite_ref-42" class="reference"><a href="#cite_note-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Cataract">Cataract</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%CE%92-Carotene&action=edit&section=17" title="Edit section: Cataract"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>A <a href="/wiki/Cochrane_Collaboration" class="mw-redirect" title="Cochrane Collaboration">Cochrane review</a> looked at supplementation of β-carotene, vitamin C, and vitamin E, independently and combined, on people to examine differences in risk of <a href="/wiki/Cataract" title="Cataract">cataract</a>, cataract extraction, progression of cataract, and slowing the loss of visual acuity. These studies found no evidence of any protective effects afforded by β-carotene supplementation on preventing and slowing age-related cataract.<sup id="cite_ref-Cochrane2012_43-0" class="reference"><a href="#cite_note-Cochrane2012-43"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup> A second meta-analysis compiled data from studies that measured diet-derived serum beta-carotene and reported a not statistically significant 10% decrease in cataract risk.<sup id="cite_ref-44" class="reference"><a href="#cite_note-44"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Erythropoietic_protoporphyria">Erythropoietic protoporphyria</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%CE%92-Carotene&action=edit&section=18" title="Edit section: Erythropoietic protoporphyria"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>High doses of β-carotene (up to 180 mg per day) may be used as a treatment for <a href="/wiki/Erythropoietic_protoporphyria" title="Erythropoietic protoporphyria">erythropoietic protoporphyria</a>, a rare inherited disorder of sunlight sensitivity, without toxic effects.<sup id="cite_ref-lpi_8-29" class="reference"><a href="#cite_note-lpi-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-mlp_9-3" class="reference"><a href="#cite_note-mlp-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Food_drying">Food drying</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%CE%92-Carotene&action=edit&section=19" title="Edit section: Food drying"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Foods rich in carotenoid dyes show discoloration upon drying. This is due to <a href="/wiki/Thermal_decomposition" title="Thermal decomposition">thermal degradation</a> of carotenoids, possibly via <a href="/wiki/Isomerization" title="Isomerization">isomerization</a> and oxidation reactions.<sup id="cite_ref-45" class="reference"><a href="#cite_note-45"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup> </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=%CE%92-Carotene&action=edit&section=20" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Sunless_tanning#Beta-carotene" title="Sunless tanning">Sunless tanning with beta-carotene</a></li> <li><a href="/wiki/Vitamin_A" title="Vitamin A">Vitamin A</a></li> <li><a href="/wiki/Retinol" title="Retinol">Retinol</a></li> <li><a href="/wiki/Carotenoids" class="mw-redirect" title="Carotenoids">Carotenoids</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%CE%92-Carotene&action=edit&section=21" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-Hursthouse-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-Hursthouse_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Hursthouse_1-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free 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.id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFHursthouseNathaniMoss2004" class="citation journal cs1">Hursthouse MB, Nathani SC, Moss GP (2004). <a rel="nofollow" class="external text" href="https://dx.doi.org/10.5517/cc8j3mh">"CSD Entry: CARTEN02"</a>. <i><a href="/wiki/Cambridge_Structural_Database" title="Cambridge Structural Database">Cambridge Structural Database</a>: Access Structures</i>. <a href="/wiki/Cambridge_Crystallographic_Data_Centre" title="Cambridge Crystallographic Data Centre">Cambridge Crystallographic Data Centre</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.5517%2Fcc8j3mh">10.5517/cc8j3mh</a><span class="reference-accessdate">. Retrieved <span class="nowrap">9 July</span> 2022</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Cambridge+Structural+Database%3A+Access+Structures&rft.atitle=CSD+Entry%3A+CARTEN02&rft.date=2004&rft_id=info%3Adoi%2F10.5517%2Fcc8j3mh&rft.aulast=Hursthouse&rft.aufirst=M.+B.&rft.au=Nathani%2C+S.+C.&rft.au=Moss%2C+G.+P.&rft_id=https%3A%2F%2Fdx.doi.org%2F10.5517%2Fcc8j3mh&rfr_id=info%3Asid%2Fen.wikipedia.org%3A%CE%92-Carotene" class="Z3988"></span></span> </li> <li id="cite_note-Senge-2"><span class="mw-cite-backlink">^ <a href="#cite_ref-Senge_2-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Senge_2-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSengeHopeSmith1992" class="citation journal cs1">Senge MO, Hope H, Smith KM (1992). <a rel="nofollow" class="external text" href="https://doi.org/10.1515%2Fznc-1992-0623">"Structure and Conformation of Photosynthetic Pigments and Related Compounds 3. 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C</a></i>. <b>47</b> (5–6): 474–476. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1515%2Fznc-1992-0623">10.1515/znc-1992-0623</a></span>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:100905826">100905826</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Z.+Naturforsch.+C&rft.atitle=Structure+and+Conformation+of+Photosynthetic+Pigments+and+Related+Compounds+3.+Crystal+Structure+of+%CE%B2-Carotene&rft.volume=47&rft.issue=5%E2%80%936&rft.pages=474-476&rft.date=1992&rft_id=info%3Adoi%2F10.1515%2Fznc-1992-0623&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A100905826%23id-name%3DS2CID&rft.aulast=Senge&rft.aufirst=Mathias+O.&rft.au=Hope%2C+H%C3%A4kon&rft.au=Smith%2C+Kevin+M.&rft_id=https%3A%2F%2Fdoi.org%2F10.1515%252Fznc-1992-0623&rfr_id=info%3Asid%2Fen.wikipedia.org%3A%CE%92-Carotene" class="Z3988"></span></span> </li> <li id="cite_note-Scifinder-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-Scifinder_3-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://scifinder.cas.org">"SciFinder – CAS Registry Number 7235-40-7"</a><span class="reference-accessdate">. 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title="Beta-Carotene">β-Carotene</a></li> <li><a href="/wiki/Gamma-Carotene" class="mw-redirect" title="Gamma-Carotene">γ-Carotene</a></li> <li><a href="/wiki/Delta-Carotene" class="mw-redirect" title="Delta-Carotene">δ-Carotene</a></li> <li><a href="/wiki/Epsilon-Carotene" class="mw-redirect" title="Epsilon-Carotene">ε-Carotene</a></li> <li><a href="/wiki/Zeta-Carotene" class="mw-redirect" title="Zeta-Carotene">ζ-Carotene</a></li> <li><a href="/wiki/Lycopene" title="Lycopene">Lycopene</a></li> <li><a href="/wiki/Neurosporene" title="Neurosporene">Neurosporene</a></li> <li><a href="/wiki/Phytoene" title="Phytoene">Phytoene</a></li> <li><a href="/wiki/Phytofluene" title="Phytofluene">Phytofluene</a></li> <li><a href="/wiki/Torulene" title="Torulene">Torulene</a></li> <li><a href="/wiki/Lycopersene" title="Lycopersene">Lycopersene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Xanthophyll" title="Xanthophyll">Xanthophylls</a> (C<sub>40</sub>)</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/Antheraxanthin" title="Antheraxanthin">Antheraxanthin</a></li> <li><a href="/wiki/Astaxanthin" title="Astaxanthin">Astaxanthin</a></li> <li><a href="/wiki/Canthaxanthin" title="Canthaxanthin">Canthaxanthin</a></li> <li><a href="/wiki/Citranaxanthin" title="Citranaxanthin">Citranaxanthin</a></li> <li><a href="/wiki/Cryptoxanthin" class="mw-redirect" title="Cryptoxanthin">Cryptoxanthin</a></li> <li><a href="/wiki/Diadinoxanthin" title="Diadinoxanthin">Diadinoxanthin</a></li> <li><a href="/wiki/Diatoxanthin" title="Diatoxanthin">Diatoxanthin</a></li> <li><a href="/wiki/Dinoxanthin" title="Dinoxanthin">Dinoxanthin</a></li> <li><a href="/wiki/Echinenone" title="Echinenone">Echinenone</a></li> <li><a href="/wiki/Flavoxanthin" title="Flavoxanthin">Flavoxanthin</a></li> <li><a href="/wiki/Fucoxanthin" title="Fucoxanthin">Fucoxanthin</a></li> <li><a href="/wiki/Lutein" title="Lutein">Lutein</a></li> <li><a href="/wiki/Neoxanthin" title="Neoxanthin">Neoxanthin</a></li> <li><a href="/wiki/Rhodoxanthin" title="Rhodoxanthin">Rhodoxanthin</a></li> <li><a href="/wiki/Rubixanthin" title="Rubixanthin">Rubixanthin</a></li> <li><a href="/wiki/Violaxanthin" title="Violaxanthin">Violaxanthin</a></li> <li><a href="/wiki/Zeaxanthin" title="Zeaxanthin">Zeaxanthin</a></li> <li><a href="/w/index.php?title=Zeinoxanthin&action=edit&redlink=1" class="new" title="Zeinoxanthin (page does not exist)">Zeinoxanthin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Apocarotenoid" title="Apocarotenoid">Apocarotenoids</a> (C<sub><40</sub>)</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/Abscisic_acid" title="Abscisic acid">Abscisic acid</a></li> <li><a href="/wiki/Apocarotenal" title="Apocarotenal">Apocarotenal</a></li> <li><a href="/wiki/Bixin" title="Bixin">Bixin</a></li> <li><a href="/wiki/Crocetin" title="Crocetin">Crocetin</a></li> <li><a href="/wiki/Food_orange_7" title="Food orange 7">Food orange 7</a></li> <li><a href="/wiki/Ionone" title="Ionone">Ionones</a></li> <li><a href="/wiki/Peridinin" title="Peridinin">Peridinin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Vitamin A retinoids (C<sub>20</sub>)</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/Retinal" title="Retinal">Retinal</a></li> <li><a href="/wiki/Retinoic_acid" title="Retinoic acid">Retinoic acid</a></li> <li><a href="/wiki/Retinol" title="Retinol">Retinol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Retinoid" title="Retinoid">Retinoid drugs</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/Acitretin" title="Acitretin">Acitretin</a></li> <li><a href="/wiki/Alitretinoin" title="Alitretinoin">Alitretinoin</a></li> <li><a href="/wiki/Bexarotene" title="Bexarotene">Bexarotene</a></li> <li><a href="/wiki/Etretinate" title="Etretinate">Etretinate</a></li> <li><a href="/wiki/Fenretinide" title="Fenretinide">Fenretinide</a></li> <li><a href="/wiki/Isotretinoin" title="Isotretinoin">Isotretinoin</a></li> <li><a href="/wiki/Tazarotene" title="Tazarotene">Tazarotene</a></li> <li><a href="/w/index.php?title=Temarotene&action=edit&redlink=1" class="new" title="Temarotene (page does not exist)">Temarotene</a></li> <li><a href="/wiki/Tretinoin" title="Tretinoin">Tretinoin</a></li> <li><a href="/w/index.php?title=Zuretinol_acetate&action=edit&redlink=1" class="new" title="Zuretinol acetate (page does not exist)">Zuretinol acetate</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"></div><div role="navigation" class="navbox" aria-labelledby="Vitamins_(A11)" 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:Vitamins" title="Template:Vitamins"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Vitamins" title="Template talk:Vitamins"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Vitamins" title="Special:EditPage/Template:Vitamins"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Vitamins_(A11)" style="font-size:114%;margin:0 4em"><a href="/wiki/Vitamin" title="Vitamin">Vitamins</a> (<a href="/wiki/ATC_code_A11" title="ATC code A11">A11</a>)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">Fat <br />soluble</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Vitamin_A" title="Vitamin A">A</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/%CE%91-Carotene" title="Α-Carotene">α-Carotene</a></li> <li><a class="mw-selflink selflink">β-Carotene</a></li> <li><a href="/wiki/Retinol" title="Retinol">Retinol</a><sup>#</sup></li> <li><a href="/wiki/Tretinoin" title="Tretinoin">Tretinoin</a><sup>#</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Vitamin_D" title="Vitamin D">D</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>D<sub>2</sub> <ul><li><a href="/wiki/Ergosterol" title="Ergosterol">Ergosterol</a></li> <li><a href="/wiki/Ergocalciferol" title="Ergocalciferol">Ergocalciferol</a><sup>#</sup></li></ul></li> <li>D<sub>3</sub> <ul><li><a href="/wiki/7-Dehydrocholesterol" title="7-Dehydrocholesterol">7-Dehydrocholesterol</a></li> <li><a href="/wiki/Previtamin_D3" title="Previtamin D3">Previtamin D<sub>3</sub></a></li> <li><a href="/wiki/Cholecalciferol" title="Cholecalciferol">Cholecalciferol</a><sup>#</sup></li> <li><a href="/wiki/Calcifediol" title="Calcifediol">25-hydroxycholecalciferol</a></li> <li><a href="/wiki/Calcitriol" title="Calcitriol">Calcitriol (1,25-dihydroxycholecalciferol)</a></li> <li><a href="/wiki/Calcitroic_acid" title="Calcitroic acid">Calcitroic acid</a></li></ul></li> <li>D<sub>4</sub> <ul><li><a href="/wiki/22-Dihydroergocalciferol" title="22-Dihydroergocalciferol">Dihydroergocalciferol</a></li></ul></li> <li><a href="/wiki/Vitamin_D5" title="Vitamin D5">D<sub>5</sub></a></li> <li>D analogues <ul><li><a href="/wiki/Alfacalcidol" title="Alfacalcidol">Alfacalcidol</a></li> <li><a href="/wiki/Dihydrotachysterol" title="Dihydrotachysterol">Dihydrotachysterol</a></li> <li><a href="/wiki/Calcipotriol" title="Calcipotriol">Calcipotriol</a></li> <li><a href="/wiki/Tacalcitol" title="Tacalcitol">Tacalcitol</a></li> <li><a href="/wiki/Paricalcitol" title="Paricalcitol">Paricalcitol</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Vitamin_E" title="Vitamin E">E</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/Tocopherol" title="Tocopherol">Tocopherol</a> <ul><li><a href="/wiki/%CE%91-Tocopherol" title="Α-Tocopherol">Alpha</a></li> <li><a href="/wiki/%CE%92-Tocopherol" title="Β-Tocopherol">Beta</a></li> <li><a href="/wiki/%CE%93-Tocopherol" title="Γ-Tocopherol">Gamma</a></li> <li><a href="/wiki/%CE%94-Tocopherol" title="Δ-Tocopherol">Delta</a></li></ul></li> <li><a href="/wiki/Tocotrienol" title="Tocotrienol">Tocotrienol</a> <ul><li><a href="/wiki/%CE%91-Tocotrienol" title="Α-Tocotrienol">Alpha</a></li> <li><a href="/wiki/%CE%92-Tocotrienol" title="Β-Tocotrienol">Beta</a></li> <li><a href="/wiki/%CE%93-Tocotrienol" title="Γ-Tocotrienol">Gamma</a></li> <li>Delta</li></ul></li> <li><a href="/wiki/Tocofersolan" title="Tocofersolan">Tocofersolan</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Vitamin_K" title="Vitamin K">K</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/1,4-Naphthoquinone" title="1,4-Naphthoquinone">Naphthoquinone</a></li> <li><a href="/wiki/Phytomenadione" title="Phytomenadione">Phylloquinone (K<sub>1</sub>)</a><sup>#</sup></li> <li><a href="/wiki/Vitamin_K2" title="Vitamin K2">Menaquinones (K<sub>2</sub>)</a></li> <li><a href="/wiki/Menadione" title="Menadione">Menadione (K<sub>3</sub>)</a><sup>‡</sup></li> <li><a href="/wiki/Vitamin_K4" class="mw-redirect" title="Vitamin K4">Various (K<sub>4</sub>)</a></li> <li><a href="/wiki/4-Amino-2-methyl-1-naphthol" title="4-Amino-2-methyl-1-naphthol">4-Amino-2-methyl-1-naphthol (K<sub>5</sub>)</a><sup>‡</sup></li> <li><a href="/wiki/2-Methylnaphthalene-1,4-diamine" title="2-Methylnaphthalene-1,4-diamine">2-Methylnaphthalene-1,4-diamine (K<sub>6</sub>)</a></li> <li><a href="/wiki/4-Amino-3-methyl-1-naphthol" title="4-Amino-3-methyl-1-naphthol">4-Amino-3-methyl-1-naphthol (K<sub>7</sub>)</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Water <br />soluble</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/B_vitamins" title="B vitamins">B</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>B<sub>1</sub> <ul><li><a href="/wiki/Thiamine" title="Thiamine">Thiamine</a><sup>#</sup></li></ul></li> <li><a href="/wiki/Vitamin_B1_analogues" title="Vitamin B1 analogues">B<sub>1</sub> analogues</a> <ul><li><a href="/wiki/Acefurtiamine" title="Acefurtiamine">Acefurtiamine</a></li> <li><a href="/wiki/Allithiamine" title="Allithiamine">Allithiamine</a></li> <li><a href="/wiki/Benfotiamine" title="Benfotiamine">Benfotiamine</a></li> <li><a href="/wiki/Fursultiamine" title="Fursultiamine">Fursultiamine</a></li> <li><a href="/wiki/Octotiamine" title="Octotiamine">Octotiamine</a></li> <li><a href="/wiki/Prosultiamine" title="Prosultiamine">Prosultiamine</a></li> <li><a href="/wiki/Sulbutiamine" title="Sulbutiamine">Sulbutiamine</a></li></ul></li> <li>B<sub>2</sub> <ul><li><a href="/wiki/Riboflavin" title="Riboflavin">Riboflavin</a><sup>#</sup></li></ul></li> <li><a href="/wiki/Vitamin_B3" title="Vitamin B3">B<sub>3</sub></a> <ul><li><a href="/wiki/Niacin" title="Niacin">Niacin</a></li> <li><a href="/wiki/Nicotinamide" title="Nicotinamide">Niacinamide</a><sup>#</sup></li></ul></li> <li>B<sub>5</sub> <ul><li><a href="/wiki/Pantothenic_acid" title="Pantothenic acid">Pantothenic acid</a></li> <li><a href="/wiki/Panthenol" title="Panthenol">Dexpanthenol</a></li> <li><a href="/wiki/Pantethine" title="Pantethine">Pantethine</a></li></ul></li> <li><a href="/wiki/Vitamin_B6" title="Vitamin B6">B<sub>6</sub></a> <ul><li><a href="/wiki/Pyridoxine" title="Pyridoxine">Pyridoxine</a><sup>#</sup>, <a href="/wiki/Pyridoxal_phosphate" title="Pyridoxal phosphate">Pyridoxal phosphate</a></li> <li><a href="/wiki/Pyridoxamine" title="Pyridoxamine">Pyridoxamine</a></li> <li><a href="/wiki/Pyritinol" title="Pyritinol">Pyritinol</a></li></ul></li> <li>B<sub>7</sub> <ul><li><a href="/wiki/Biotin" title="Biotin">Biotin</a></li></ul></li> <li>B<sub>9</sub> <ul><li><a href="/wiki/Folate" title="Folate">Folic acid</a><sup>#</sup></li> <li><a href="/wiki/Dihydrofolic_acid" title="Dihydrofolic acid">Dihydrofolic acid</a></li> <li><a href="/wiki/Folinic_acid" title="Folinic acid">Folinic acid</a></li> <li><a href="/wiki/Levomefolic_acid" title="Levomefolic acid">Levomefolic acid</a></li></ul></li> <li><a href="/wiki/Vitamin_B12" title="Vitamin B12">B<sub>12</sub></a> <ul><li><a href="/wiki/Adenosylcobalamin" title="Adenosylcobalamin">Adenosylcobalamin</a></li> <li><a href="/wiki/Cyanocobalamin" title="Cyanocobalamin">Cyanocobalamin</a></li> <li><a href="/wiki/Hydroxocobalamin" title="Hydroxocobalamin">Hydroxocobalamin</a><sup>#</sup></li> <li><a href="/wiki/Methylcobalamin" title="Methylcobalamin">Methylcobalamin</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Vitamin_C" title="Vitamin C">C</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Vitamin_C" title="Vitamin C">Ascorbic acid</a><sup>#</sup></li> <li><a href="/wiki/Dehydroascorbic_acid" title="Dehydroascorbic acid">Dehydroascorbic acid</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Combinations</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/Multivitamin" title="Multivitamin">Multivitamins</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"><div class="hlist"> <ul><li><sup>#</sup><a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">WHO-EM</a></li> <li><sup>‡</sup><a href="/wiki/List_of_withdrawn_drugs" title="List of withdrawn drugs">Withdrawn</a> from market</li> <li><a href="/wiki/Clinical_trial" title="Clinical trial">Clinical trials</a>: <ul><li><sup>†</sup><a href="/wiki/Phases_of_clinical_research#Phase_III" title="Phases of clinical research">Phase III</a></li> <li><sup>§</sup>Never to phase III</li></ul></li></ul> </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"></div><div role="navigation" class="navbox" aria-labelledby="Emollients_and_protectives_(D02)" 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:Emollients_and_protectives" title="Template:Emollients and protectives"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Emollients_and_protectives" title="Template talk:Emollients and protectives"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Emollients_and_protectives" title="Special:EditPage/Template:Emollients and protectives"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Emollients_and_protectives_(D02)" style="font-size:114%;margin:0 4em"><a href="/wiki/Emollient" class="mw-redirect" title="Emollient">Emollients</a> and protectives (<a href="/wiki/ATC_code_D02" title="ATC code D02">D02</a>)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">Emollients and protectives</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/Paraffin_wax" title="Paraffin wax">Paraffin</a></li> <li><a href="/wiki/Carbamide" class="mw-redirect" title="Carbamide">Carbamide</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Protectives against <a href="/wiki/UV-radiation" class="mw-redirect" title="UV-radiation">UV-radiation</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/4-Aminobenzoic_acid" title="4-Aminobenzoic acid">Aminobenzoic acid</a></li> <li><a href="/wiki/Octyl_methoxycinnamate" title="Octyl methoxycinnamate">Octinoxate</a></li> <li><a href="/wiki/Beta-Carotene" class="mw-redirect" title="Beta-Carotene">Betacarotene</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Types_of_terpenes_and_terpenoids_(#_of_isoprene_units)" style="padding:3px"><table class="nowraplinks mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Terpenoids" title="Template:Terpenoids"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Terpenoids" title="Template talk:Terpenoids"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Terpenoids" title="Special:EditPage/Template:Terpenoids"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Types_of_terpenes_and_terpenoids_(#_of_isoprene_units)" style="font-size:114%;margin:0 4em">Types of <a href="/wiki/Terpene" title="Terpene">terpenes</a> and <a href="/wiki/Terpenoid" title="Terpenoid">terpenoids</a> (# of <a href="/wiki/Isoprene" title="Isoprene">isoprene</a> units)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">Basic forms:</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>Acyclic (linear, <i>cis</i> and <i>trans</i> forms)</li> <li>Monocyclic (single ring)</li> <li>Bicyclic (2 rings)</li> <li><a href="/wiki/Iridoid" title="Iridoid">Iridoids</a> (cyclopentane ring)</li> <li>Iridoid glycosides (iridoids bound to a sugar)</li> <li><a href="/wiki/Steroid" title="Steroid">Steroids</a> (4 rings)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Hemiterpenoid" class="mw-redirect" title="Hemiterpenoid">Hemiterpenoids</a> (1)</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/Isoprene" title="Isoprene">Isoprene</a> (C<sub>5</sub>H<sub>8</sub>)</li> <li><a href="/wiki/Prenol" title="Prenol">Prenol</a></li> <li><a href="/wiki/Isovaleric_acid" title="Isovaleric acid">Isovaleric acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Monoterpene" title="Monoterpene">Monoterpenes</a> <br />(C<sub>10</sub>H<sub>16</sub>)(2)</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">Acyclic</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/Ocimene" title="Ocimene">Ocimene</a></li> <li><a href="/wiki/Myrcene" title="Myrcene">Myrcenes</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Monocyclic</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/Limonene" title="Limonene">Limonene</a></li> <li><a href="/wiki/Terpinene" title="Terpinene">Terpinene</a></li> <li><a href="/wiki/Phellandrene" title="Phellandrene">Phellandrene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Bicyclic</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/Pinene" title="Pinene">Pinene</a> (<a href="/wiki/Alpha-Pinene" class="mw-redirect" title="Alpha-Pinene">α</a> and <a href="/wiki/Beta-Pinene" class="mw-redirect" title="Beta-Pinene">β</a>)</li> <li><a href="/wiki/Camphene" title="Camphene">Camphene</a></li> <li><a href="/wiki/Thujene" title="Thujene">Thujene</a></li> <li><a href="/wiki/Sabinene" title="Sabinene">Sabinene</a></li> <li><a href="/wiki/Carene" class="mw-redirect" title="Carene">Carene</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Monoterpenoids <br />(2,modified)</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">Acyclic</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/Citronellal" title="Citronellal">Citronellal</a></li> <li><a href="/wiki/Citral" title="Citral">Citral</a></li> <li><a href="/wiki/Citronellol" title="Citronellol">Citronellol</a></li> <li><a href="/wiki/Geraniol" title="Geraniol">Geraniol</a></li> <li><a href="/wiki/Geranyl_pyrophosphate" title="Geranyl pyrophosphate">Geranyl pyrophosphate</a></li> <li><a href="/wiki/Halomon" title="Halomon">Halomon</a></li> <li><a href="/wiki/Linalool" title="Linalool">Linalool</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Monocyclic</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/Grapefruit_mercaptan" title="Grapefruit mercaptan">Grapefruit mercaptan</a></li> <li><a href="/wiki/Menthol" title="Menthol">Menthol</a></li> <li><a href="/wiki/P-Cymene" title="P-Cymene">p-Cymene</a></li> <li><a href="/wiki/Thujaplicin" title="Thujaplicin">Thujaplicins</a> (<a href="/wiki/Hinokitiol" title="Hinokitiol">Hinokitiol</a>)</li> <li><a href="/wiki/Thymol" title="Thymol">Thymol</a></li> <li><a href="/wiki/Perillyl_alcohol" title="Perillyl alcohol">Perillyl alcohol</a></li> <li><a href="/wiki/Carvacrol" title="Carvacrol">Carvacrol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Bicyclic</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/Camphor" title="Camphor">Camphor</a></li> <li><a href="/wiki/Borneol" title="Borneol">Borneol</a></li> <li><a href="/wiki/Bornyl_acetate" title="Bornyl acetate">Bornyl acetate</a></li> <li><a href="/wiki/Eucalyptol" title="Eucalyptol">Eucalyptol</a></li> <li><a href="/wiki/Ascaridole" title="Ascaridole">Ascaridole</a></li> <li><a href="/wiki/Umbellulone" title="Umbellulone">Umbellulone</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Sesquiterpenoids" class="mw-redirect" title="Sesquiterpenoids">Sesquiterpenoids</a> (3)</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/Artemisinin" title="Artemisinin">Artemisinin</a></li> <li><a href="/wiki/Bisabolol" title="Bisabolol">Bisabolol</a></li> <li><a href="/wiki/Cadinene" class="mw-redirect" title="Cadinene">Cadinene</a></li> <li><a href="/wiki/Cadinol" title="Cadinol">Cadinol</a></li> <li><a href="/wiki/Cedrene" title="Cedrene">Cedrene</a></li> <li>Chanootin</li> <li><a href="/wiki/Farnesyl_pyrophosphate" title="Farnesyl pyrophosphate">Farnesyl pyrophosphate</a></li> <li>Juniperol</li> <li><a href="/wiki/Longifolene" title="Longifolene">Longifolene</a></li> <li>Muurolene</li> <li>Nootkatin</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Terpenoid" title="Terpenoid">Diterpenoids</a> (4)</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">Acyclic</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/Phytol" title="Phytol">Phytol</a></li> <li><a href="/wiki/Geranylgeranyl_pyrophosphate" title="Geranylgeranyl pyrophosphate">Geranylgeranyl pyrophosphate</a></li> <li>Geranyl-linalool</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Monocyclic</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/Retinol" title="Retinol">Retinol</a></li> <li><a href="/wiki/Retinal" title="Retinal">Retinal</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Bicyclic</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>cis</i>-Abienol</li> <li>Epimanool</li> <li><a href="/wiki/Salvinorin_A" title="Salvinorin A">Salvinorin A</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Tricyclic</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/Cembrene" class="mw-redirect" title="Cembrene">Cembrene</a></li> <li><a href="/wiki/Forskolin" title="Forskolin">Forskolin</a></li> <li>Manoyl oxide</li> <li>Pimaral</li> <li>Pimarol</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Tetracyclic</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/Aphidicolin" title="Aphidicolin">Aphidicolin</a></li> <li><a href="/wiki/Gibberellin" title="Gibberellin">Gibberellin</a></li> <li><a href="/wiki/Paclitaxel" title="Paclitaxel">Paclitaxel</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Resin_acid" title="Resin acid">Resin acids</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/Abietic_acid" title="Abietic acid">Abietic acid</a></li> <li>Communic acid</li> <li>Dehydroabietic acid</li> <li><a href="/wiki/Isopimaric_acid" title="Isopimaric acid">Isopimaric acid</a></li> <li>Lambertianic acid</li> <li><a href="/wiki/Levopimaric_acid" title="Levopimaric acid">Levopimaric acid</a></li> <li>Mercusic acid</li> <li>Neoabietic acid</li> <li><a href="/wiki/Pimaric_acid" title="Pimaric acid">Pimaric acid</a></li> <li>Sandaracopimaric acid</li> <li>Secodehydroabietic acid</li> <li>Palustric acid</li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Sesterterpenoid" class="mw-redirect" title="Sesterterpenoid">Sesterterpenoids</a> (5)</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>Geranylfarnesol</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Triterpenoid" class="mw-redirect" title="Triterpenoid">Triterpenoids</a> (6)</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Steroid" title="Steroid">Steroids</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/Phytosterol" title="Phytosterol">Phytosterols</a> <ul><li><a href="/wiki/Campesterol" title="Campesterol">Campesterol</a></li> <li>Citrostadienol</li> <li><a href="/wiki/Cycloartenol" title="Cycloartenol">Cycloartenol</a></li> <li><a href="/wiki/Sitostanol" class="mw-redirect" title="Sitostanol">Sitostanol</a></li> <li><a href="/wiki/Sitosterol" class="mw-redirect" title="Sitosterol">Sitosterol</a></li> <li><a href="/wiki/Stigmasterol" title="Stigmasterol">Stigmasterol</a></li></ul></li> <li><a href="/wiki/Tocopherol" title="Tocopherol">Tocopherols</a></li> <li><a href="/wiki/Cholesterol" title="Cholesterol">Cholesterol</a></li> <li><a href="/wiki/Testosterone" title="Testosterone">Testosterone</a></li> <li><a href="/wiki/Cholecalciferol" title="Cholecalciferol">Cholecalciferol</a></li> <li><a href="/wiki/Ecdysone" title="Ecdysone">Ecdysones</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/Betulin" title="Betulin">Betulin</a></li> <li><a href="/wiki/Lanosterol" title="Lanosterol">Lanosterol</a></li> <li><a href="/wiki/Saponin" title="Saponin">Saponins</a></li> <li>Serratenediol</li> <li><a href="/wiki/Squalane" title="Squalane">Squalane</a></li> <li>Acids <ul><li><a href="/wiki/Oleanolic_acid" title="Oleanolic acid">Oleanolic acid</a></li> <li><a href="/wiki/Ursolic_acid" title="Ursolic acid">Ursolic acid</a></li> <li><a href="/wiki/Betulinic_acid" title="Betulinic acid">Betulinic acid</a></li> <li><a href="/wiki/Moronic_acid" title="Moronic acid">Moronic acid</a></li></ul></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Sesquarterpenes/oids (7)</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>Ferrugicadiol</li> <li>Tetraprenylcurcumene</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Tetraterpenoid" class="mw-redirect" title="Tetraterpenoid">Tetraterpenoids</a><br />(<a href="/wiki/Carotenoid" title="Carotenoid">Carotenoids</a>) (8)</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Carotene" title="Carotene">Carotenes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Alpha-Carotene" class="mw-redirect" title="Alpha-Carotene">Alpha-Carotene</a></li> <li><a href="/wiki/Beta-Carotene" class="mw-redirect" title="Beta-Carotene">Beta-Carotene</a></li> <li><a href="/wiki/Gamma-Carotene" class="mw-redirect" title="Gamma-Carotene">Gamma-Carotene</a></li> <li><a href="/wiki/Delta-Carotene" class="mw-redirect" title="Delta-Carotene">Delta-Carotene</a></li> <li><a href="/wiki/Lycopene" title="Lycopene">Lycopene</a></li> <li><a href="/wiki/Neurosporene" title="Neurosporene">Neurosporene</a></li> <li><a href="/wiki/Phytofluene" title="Phytofluene">Phytofluene</a></li> <li><a href="/wiki/Phytoene" title="Phytoene">Phytoene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Xanthophyll" title="Xanthophyll">Xanthophylls</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/Canthaxanthin" title="Canthaxanthin">Canthaxanthin</a></li> <li><a href="/wiki/Cryptoxanthin" class="mw-redirect" title="Cryptoxanthin">Cryptoxanthin</a></li> <li><a href="/wiki/Zeaxanthin" title="Zeaxanthin">Zeaxanthin</a></li> <li><a href="/wiki/Astaxanthin" title="Astaxanthin">Astaxanthin</a></li> <li><a href="/wiki/Lutein" title="Lutein">Lutein</a></li> <li><a href="/wiki/Rubixanthin" title="Rubixanthin">Rubixanthin</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Polyterpenoid" class="mw-redirect" title="Polyterpenoid">Polyterpenoids</a> (many)</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/Natural_rubber" title="Natural rubber">Natural rubber</a></li> <li><a href="/wiki/Gutta_percha" class="mw-redirect" title="Gutta percha">Gutta percha</a></li> <li>Gutta-balatá</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Norisoprenoids (modified)</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>3-oxo-α-ionol</li> <li>7,8-dihydroionone</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Synthesis</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>Terpene synthase enzymes (many), having in common a <a href="/wiki/Terpene_synthase_N_terminal_domain" title="Terpene synthase N terminal domain">terpene synthase N terminal domain</a> (<a href="/wiki/Protein_domain" title="Protein domain">protein domain</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Activated isoprene forms</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/Isopentenyl_pyrophosphate" title="Isopentenyl pyrophosphate">Isopentenyl pyrophosphate</a> (IPP)</li> <li><a href="/wiki/Dimethylallyl_pyrophosphate" title="Dimethylallyl pyrophosphate">Dimethylallyl pyrophosphate</a> (DMAPP)</li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox authority-control" 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