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class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Biosynthesis"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Biosynthesis</span> </div> </a> <button aria-controls="toc-Biosynthesis-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 Biosynthesis subsection</span> </button> <ul id="toc-Biosynthesis-sublist" class="vector-toc-list"> <li id="toc-Isoprene_as_the_building_block" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Isoprene_as_the_building_block"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1</span> <span>Isoprene as the building block</span> </div> </a> <ul id="toc-Isoprene_as_the_building_block-sublist" class="vector-toc-list"> <li id="toc-Mevalonate_pathway" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Mevalonate_pathway"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1.1</span> <span>Mevalonate pathway</span> </div> </a> <ul id="toc-Mevalonate_pathway-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Non-mevalonate_pathway" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Non-mevalonate_pathway"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1.2</span> <span>Non-mevalonate pathway</span> </div> </a> <ul id="toc-Non-mevalonate_pathway-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Geranyl_pyrophosphate_phase_and_beyond" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Geranyl_pyrophosphate_phase_and_beyond"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.2</span> <span>Geranyl pyrophosphate phase and beyond</span> </div> </a> <ul id="toc-Geranyl_pyrophosphate_phase_and_beyond-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Terpenes_to_terpenoids" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Terpenes_to_terpenoids"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.3</span> <span>Terpenes to terpenoids</span> </div> </a> <ul id="toc-Terpenes_to_terpenoids-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Structure" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Structure"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Structure</span> </div> </a> <button aria-controls="toc-Structure-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 Structure subsection</span> </button> <ul id="toc-Structure-sublist" class="vector-toc-list"> <li id="toc-Formula" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Formula"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.1</span> <span>Formula</span> </div> </a> <ul id="toc-Formula-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Chirality" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Chirality"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.2</span> <span>Chirality</span> </div> </a> <ul id="toc-Chirality-sublist" class="vector-toc-list"> <li id="toc-Unsaturation" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Unsaturation"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.2.1</span> <span>Unsaturation</span> </div> </a> <ul id="toc-Unsaturation-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Classification" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Classification"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.3</span> <span>Classification</span> </div> </a> <ul id="toc-Classification-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Industrial_syntheses" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Industrial_syntheses"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Industrial syntheses</span> </div> </a> <ul id="toc-Industrial_syntheses-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">8</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>External links</span> </div> </a> <ul id="toc-External_links-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" title="Table of Contents" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span class="vector-dropdown-label-text">Toggle the table of contents</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Terpene</span></h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="Go to an article in another language. Available in 46 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-46" 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">46 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%AA%D8%B1%D8%A8%D9%8A%D9%86" title="تربين – Arabic" lang="ar" hreflang="ar" data-title="تربين" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-az mw-list-item"><a href="https://az.wikipedia.org/wiki/Terpenl%C9%99r" title="Terpenlər – Azerbaijani" lang="az" hreflang="az" data-title="Terpenlər" data-language-autonym="Azərbaycanca" data-language-local-name="Azerbaijani" class="interlanguage-link-target"><span>Azərbaycanca</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%A2%D0%B5%D1%80%D0%BF%D0%B5%D0%BD" title="Терпен – Bulgarian" lang="bg" hreflang="bg" data-title="Терпен" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target"><span>Български</span></a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Terpen" title="Terpen – Bosnian" lang="bs" hreflang="bs" data-title="Terpen" data-language-autonym="Bosanski" data-language-local-name="Bosnian" class="interlanguage-link-target"><span>Bosanski</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Terp%C3%A8" title="Terpè – Catalan" lang="ca" hreflang="ca" data-title="Terpè" 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/Terpeny" title="Terpeny – Czech" lang="cs" hreflang="cs" data-title="Terpeny" 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/Terpen" title="Terpen – Danish" lang="da" hreflang="da" data-title="Terpen" 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-Q17437798 badge-goodarticle mw-list-item" title="good article badge"><a href="https://de.wikipedia.org/wiki/Terpene" title="Terpene – German" lang="de" hreflang="de" data-title="Terpene" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/Terpeenid" title="Terpeenid – Estonian" lang="et" hreflang="et" data-title="Terpeenid" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%A4%CE%B5%CF%81%CF%80%CE%AD%CE%BD%CE%B9%CE%B1" title="Τερπένια – Greek" lang="el" hreflang="el" data-title="Τερπένια" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target"><span>Ελληνικά</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Terpeno" title="Terpeno – Spanish" lang="es" hreflang="es" data-title="Terpeno" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eo mw-list-item"><a href="https://eo.wikipedia.org/wiki/Terpeno" title="Terpeno – Esperanto" lang="eo" hreflang="eo" data-title="Terpeno" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Terpeno" title="Terpeno – Basque" lang="eu" hreflang="eu" data-title="Terpeno" 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%AA%D8%B1%D9%BE%D9%86" title="ترپن – Persian" lang="fa" hreflang="fa" data-title="ترپن" 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/Terp%C3%A8ne" title="Terpène – French" lang="fr" hreflang="fr" data-title="Terpène" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ga mw-list-item"><a href="https://ga.wikipedia.org/wiki/Teirp%C3%A9in" title="Teirpéin – Irish" lang="ga" hreflang="ga" data-title="Teirpéin" data-language-autonym="Gaeilge" data-language-local-name="Irish" class="interlanguage-link-target"><span>Gaeilge</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Terpeno" title="Terpeno – Galician" lang="gl" hreflang="gl" data-title="Terpeno" 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/%ED%85%8C%EB%A5%B4%ED%8E%9C" title="테르펜 – Korean" lang="ko" hreflang="ko" data-title="테르펜" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D5%8F%D5%A5%D6%80%D5%BA%D5%A5%D5%B6%D5%B6%D5%A5%D6%80" title="Տերպեններ – Armenian" lang="hy" hreflang="hy" data-title="Տերպեններ" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-hi mw-list-item"><a href="https://hi.wikipedia.org/wiki/%E0%A4%9F%E0%A4%B0%E0%A4%AA%E0%A5%80%E0%A4%A8" title="टरपीन – Hindi" lang="hi" hreflang="hi" data-title="टरपीन" data-language-autonym="हिन्दी" data-language-local-name="Hindi" class="interlanguage-link-target"><span>हिन्दी</span></a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Terpeni" title="Terpeni – Croatian" lang="hr" hreflang="hr" data-title="Terpeni" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Terpena" title="Terpena – Indonesian" lang="id" hreflang="id" data-title="Terpena" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target"><span>Bahasa Indonesia</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Terpeni" title="Terpeni – Italian" lang="it" hreflang="it" data-title="Terpeni" 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%98%D7%A8%D7%A4%D7%9F_(%D7%9B%D7%99%D7%9E%D7%99%D7%94)" title="טרפן (כימיה) – Hebrew" lang="he" hreflang="he" data-title="טרפן (כימיה)" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-kk mw-list-item"><a href="https://kk.wikipedia.org/wiki/%D0%A2%D0%B5%D1%80%D0%BF%D0%B5%D0%BD%D0%B4%D0%B5%D1%80" title="Терпендер – Kazakh" lang="kk" hreflang="kk" data-title="Терпендер" data-language-autonym="Қазақша" data-language-local-name="Kazakh" class="interlanguage-link-target"><span>Қазақша</span></a></li><li class="interlanguage-link interwiki-ky mw-list-item"><a href="https://ky.wikipedia.org/wiki/%D0%A2%D0%B5%D1%80%D0%BF%D0%B5%D0%BD%D0%B4%D0%B5%D1%80" title="Терпендер – Kyrgyz" lang="ky" hreflang="ky" data-title="Терпендер" data-language-autonym="Кыргызча" data-language-local-name="Kyrgyz" class="interlanguage-link-target"><span>Кыргызча</span></a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Terp%C4%93ni" title="Terpēni – Latvian" lang="lv" hreflang="lv" data-title="Terpēni" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target"><span>Latviešu</span></a></li><li class="interlanguage-link interwiki-ml mw-list-item"><a href="https://ml.wikipedia.org/wiki/%E0%B4%9F%E0%B5%BC%E0%B4%AA%E0%B5%8D%E0%B4%AA%E0%B5%80%E0%B4%A8%E0%B5%81%E0%B4%95%E0%B5%BE" title="ടർപ്പീനുകൾ – Malayalam" lang="ml" hreflang="ml" data-title="ടർപ്പീനുകൾ" data-language-autonym="മലയാളം" data-language-local-name="Malayalam" class="interlanguage-link-target"><span>മലയാളം</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Terpena" title="Terpena – Malay" lang="ms" hreflang="ms" data-title="Terpena" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" class="interlanguage-link-target"><span>Bahasa Melayu</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Terpeen" title="Terpeen – Dutch" lang="nl" hreflang="nl" data-title="Terpeen" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%86%E3%83%AB%E3%83%9A%E3%83%B3" title="テルペン – Japanese" lang="ja" hreflang="ja" data-title="テルペン" 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-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Terpen" title="Terpen – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Terpen" data-language-autonym="Norsk bokmål" data-language-local-name="Norwegian Bokmål" class="interlanguage-link-target"><span>Norsk bokmål</span></a></li><li class="interlanguage-link interwiki-uz mw-list-item"><a href="https://uz.wikipedia.org/wiki/Terpenlar" title="Terpenlar – Uzbek" lang="uz" hreflang="uz" data-title="Terpenlar" data-language-autonym="Oʻzbekcha / ўзбекча" data-language-local-name="Uzbek" class="interlanguage-link-target"><span>Oʻzbekcha / ўзбекча</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Terpeny" title="Terpeny – Polish" lang="pl" hreflang="pl" data-title="Terpeny" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Terpen" title="Terpen – Romanian" lang="ro" hreflang="ro" data-title="Terpen" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%A2%D0%B5%D1%80%D0%BF%D0%B5%D0%BD%D1%8B" title="Терпены – Russian" lang="ru" hreflang="ru" data-title="Терпены" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Terp%C3%A9n" title="Terpén – Slovak" lang="sk" hreflang="sk" data-title="Terpén" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Terpen" title="Terpen – Slovenian" lang="sl" hreflang="sl" data-title="Terpen" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Terpen" title="Terpen – Serbian" lang="sr" hreflang="sr" data-title="Terpen" 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/Terpen" title="Terpen – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Terpen" 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/Terpeenit" title="Terpeenit – Finnish" lang="fi" hreflang="fi" data-title="Terpeenit" 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/Terpen" title="Terpen – Swedish" lang="sv" hreflang="sv" data-title="Terpen" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B9%80%E0%B8%97%E0%B8%AD%E0%B8%A3%E0%B9%8C%E0%B8%9E%E0%B8%B5%E0%B8%99" title="เทอร์พีน – Thai" lang="th" hreflang="th" data-title="เทอร์พีน" data-language-autonym="ไทย" data-language-local-name="Thai" class="interlanguage-link-target"><span>ไทย</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Terpen" title="Terpen – Turkish" lang="tr" hreflang="tr" data-title="Terpen" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%A2%D0%B5%D1%80%D0%BF%D0%B5%D0%BD%D0%B8" title="Терпени – Ukrainian" lang="uk" hreflang="uk" data-title="Терпени" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E8%90%9C%E7%83%AF" title="萜烯 – Chinese" lang="zh" hreflang="zh" data-title="萜烯" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target"><span>中文</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span class="wb-langlinks-edit wb-langlinks-link"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q212364#sitelinks-wikipedia" title="Edit interlanguage links" class="wbc-editpage">Edit links</a></span></div> </div> </div> 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href="/wiki/Terpin" title="Terpin">Terpin</a>.</div> <div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Class of oily organic compounds found in plants</div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:R%C3%A9sine.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6a/R%C3%A9sine.jpg/170px-R%C3%A9sine.jpg" decoding="async" width="170" height="263" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6a/R%C3%A9sine.jpg/255px-R%C3%A9sine.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6a/R%C3%A9sine.jpg/340px-R%C3%A9sine.jpg 2x" data-file-width="530" data-file-height="820" /></a><figcaption>Many terpenes are derived commercially from conifer resins, such as those made by this <a href="/wiki/Pine" title="Pine">pine</a>.</figcaption></figure> <p><b>Terpenes</b> (<span class="rt-commentedText nowrap"><span class="IPA nopopups noexcerpt" lang="en-fonipa"><a href="/wiki/Help:IPA/English" title="Help:IPA/English">/<span style="border-bottom:1px dotted"><span title="/ˈ/: primary stress follows">ˈ</span><span title="'t' in 'tie'">t</span><span title="/ɜːr/: 'ur' in 'fur'">ɜːr</span><span title="'p' in 'pie'">p</span><span title="/iː/: 'ee' in 'fleece'">iː</span><span title="'n' in 'nigh'">n</span></span>/</a></span></span>) are a class of <a href="/wiki/Natural_product" title="Natural product">natural products</a> consisting of compounds with the formula (C<sub>5</sub>H<sub>8</sub>)<sub>n</sub> for n ≥ 2. Terpenes are major biosynthetic building blocks. Comprising more than 30,000 compounds, these unsaturated <a href="/wiki/Hydrocarbons" class="mw-redirect" title="Hydrocarbons">hydrocarbons</a> are produced predominantly by <a href="/wiki/Plant" title="Plant">plants</a>, particularly <a href="/wiki/Pinophyta" class="mw-redirect" title="Pinophyta">conifers</a>.<sup id="cite_ref-book_1-0" class="reference"><a href="#cite_note-book-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Crot_2-0" class="reference"><a href="#cite_note-Crot-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> In plants, terpenes and terpenoids are important mediators of ecological <a href="/wiki/Biological_interaction" title="Biological interaction">interactions</a>, while some insects use some terpenes as a form of defense. Other functions of terpenoids include cell growth modulation and plant elongation, light harvesting and photoprotection, and membrane permeability and fluidity control. </p><p>Terpenes are classified by the number of carbons: <a href="/wiki/Monoterpenes" class="mw-redirect" title="Monoterpenes">monoterpenes</a> (C<sub>10</sub>), <a href="/wiki/Sesquiterpenes" class="mw-redirect" title="Sesquiterpenes">sesquiterpenes</a> (C<sub>15</sub>), <a href="/wiki/Diterpenes" class="mw-redirect" title="Diterpenes">diterpenes</a> (C<sub>20</sub>), as examples. The terpene <a href="/wiki/Alpha-pinene" class="mw-redirect" title="Alpha-pinene">alpha-pinene</a> is a major component of the common <a href="/wiki/Solvent" title="Solvent">solvent</a>, <a href="/wiki/Turpentine" title="Turpentine">turpentine</a>. </p><p>The one terpene that has major applications is <a href="/wiki/Natural_rubber" title="Natural rubber">natural rubber</a> (i.e., <a href="/wiki/Polyisoprene" title="Polyisoprene">polyisoprene</a>). The possibility that other terpenes could be used as precursors to produce synthetic <a href="/wiki/Polymer" title="Polymer">polymers</a> has been investigated. Many terpenes have been shown to have pharmacological effects. Terpenes are also components of some traditional medicines, such as <a href="/wiki/Aromatherapy" title="Aromatherapy">aromatherapy</a>, and as active ingredients of <a href="/wiki/Pesticide" title="Pesticide">pesticides</a> in agriculture.<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="History_and_terminology">History and terminology</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Terpene&action=edit&section=1" title="Edit section: History and terminology"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The term <i>terpene</i> was coined in 1866 by the German chemist <a href="/wiki/August_Kekul%C3%A9" title="August Kekulé">August Kekulé</a> to denote all hydrocarbons having the empirical formula C<sub>10</sub>H<sub>16</sub>, of which <a href="/wiki/Camphene" title="Camphene">camphene</a> was one. Previously, many hydrocarbons having the empirical formula C<sub>10</sub>H<sub>16</sub> had been called "camphene", but many other hydrocarbons of the same composition had different names. Kekulé coined the term "terpene" in order to reduce the confusion.<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> The name "terpene" is a shortened form of "terpentine", an obsolete spelling of "<a href="/wiki/Turpentine" title="Turpentine">turpentine</a>".<sup id="cite_ref-Ull_7-0" class="reference"><a href="#cite_note-Ull-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p><p>Although sometimes used interchangeably with "terpenes", <a href="/wiki/Terpenoid" title="Terpenoid">terpenoids</a> (or <a href="/wiki/Isoprenoid" class="mw-redirect" title="Isoprenoid">isoprenoids</a>) are modified terpenes that contain additional <a href="/wiki/Functional_group" title="Functional group">functional groups</a>, usually oxygen-containing.<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> The terms terpenes and terpenoids are often used interchangeably, however. Furthermore, terpenes are produced from terpenoids and many terpenoids are produced from terpenes. Both have strong and often pleasant odors, which may protect their hosts or attract pollinators. The number of terpenes and terpenoids is estimated at 55,000 chemical entities.<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p><p>The 1939 <a href="/wiki/Nobel_Prize_in_Chemistry" title="Nobel Prize in Chemistry">Nobel Prize in Chemistry</a> was awarded to <a href="/wiki/Leopold_Ru%C5%BEi%C4%8Dka" title="Leopold Ružička">Leopold Ružička</a> "for his work on <a href="/wiki/Polymethylenes" class="mw-redirect" title="Polymethylenes">polymethylenes</a> and higher terpenes",<sup id="cite_ref-Nobel_10-0" class="reference"><a href="#cite_note-Nobel-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup><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> "including the first <a href="/wiki/Chemical_synthesis" title="Chemical synthesis">chemical synthesis</a> of <a href="/wiki/Male_sex_hormones" class="mw-redirect" title="Male sex hormones">male sex hormones</a>."<sup id="cite_ref-hillier19_12-0" class="reference"><a href="#cite_note-hillier19-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Biological_function">Biological function</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Terpene&action=edit&section=2" title="Edit section: Biological function"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Terpenes are major biosynthetic building blocks. <a href="/wiki/Steroids" class="mw-redirect" title="Steroids">Steroids</a>, for example, are derivatives of the triterpene <a href="/wiki/Squalene" title="Squalene">squalene</a>. Terpenes and terpenoids are also the primary constituents of the <a href="/wiki/Essential_oil" title="Essential oil">essential oils</a> of many types of plants and flowers.<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> In plants, terpenes and terpenoids are important mediators of ecological <a href="/wiki/Biological_interaction" title="Biological interaction">interactions</a>. For example, they play a role in <a href="/wiki/Plant_defense_against_herbivory" title="Plant defense against herbivory">plant defense against herbivory</a>, <a href="/wiki/Plant_disease_resistance" title="Plant disease resistance">disease resistance</a>, attraction of <a href="/wiki/Mutualism_(biology)" title="Mutualism (biology)">mutualists</a> such as <a href="/wiki/Pollinator" title="Pollinator">pollinators</a>, as well as potentially plant-<a href="/wiki/Plant_communication" title="Plant communication">plant communication</a>.<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup><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> They appear to play roles as <a href="/wiki/Antifeedant" title="Antifeedant">antifeedants</a>.<sup id="cite_ref-Crot_2-1" class="reference"><a href="#cite_note-Crot-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> Other functions of terpenoids include cell growth modulation and plant elongation, light harvesting and photoprotection, and membrane permeability and fluidity control.<sup id="cite_ref-Roberts2007_16-0" class="reference"><a href="#cite_note-Roberts2007-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p><p>Higher amounts of terpenes are released by trees in warmer weather,<sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> where they may function as a natural mechanism of <a href="/wiki/Cloud_seeding" title="Cloud seeding">cloud seeding</a>. The clouds reflect sunlight, allowing the forest temperature to regulate.<sup id="cite_ref-18" class="reference"><a href="#cite_note-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> </p><p>Some insects use some terpenes as a form of defense. For example, <a href="/wiki/Termite" title="Termite">termites</a> of the subfamily <a href="/wiki/Nasutitermitinae" title="Nasutitermitinae">Nasutitermitinae</a> <a href="/wiki/Anti-predator_adaptation" title="Anti-predator adaptation">ward off predatory insects</a> through the use of a specialized mechanism called a <a href="/wiki/Fontanellar_gun" title="Fontanellar gun">fontanellar gun</a>, which ejects a resinous mixture of terpenes.<sup id="cite_ref-Psyche_19-0" class="reference"><a href="#cite_note-Psyche-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Applications">Applications</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Terpene&action=edit&section=3" title="Edit section: Applications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Naturkautschuk.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/63/Naturkautschuk.svg/110px-Naturkautschuk.svg.png" decoding="async" width="110" height="78" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/63/Naturkautschuk.svg/165px-Naturkautschuk.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/63/Naturkautschuk.svg/220px-Naturkautschuk.svg.png 2x" data-file-width="180" data-file-height="128" /></a><figcaption>Structure of natural rubber, exhibiting the characteristic methyl group on the alkene group</figcaption></figure> <p>The one terpene that has major applications is <a href="/wiki/Natural_rubber" title="Natural rubber">natural rubber</a> (i.e., <a href="/wiki/Polyisoprene" title="Polyisoprene">polyisoprene</a>). The possibility that other terpenes could be used as precursors to produce synthetic <a href="/wiki/Polymer" title="Polymer">polymers</a> has been investigated as an alternative to the use of petroleum-based feedstocks. However, few of these applications have been commercialized.<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> Many other terpenes, however, have smaller scale commercial and industrial applications. For example, <a href="/wiki/Turpentine" title="Turpentine">turpentine</a>, a mixture of terpenes (e.g., <a href="/wiki/Pinene" title="Pinene">pinene</a>), obtained from the distillation of pine tree <a href="/wiki/Resin" title="Resin">resin</a>, is used as an organic <a href="/wiki/Solvent" title="Solvent">solvent</a> and as a chemical feedstock (mainly for the production of other terpenoids).<sup id="cite_ref-Ull_7-1" class="reference"><a href="#cite_note-Ull-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Rosin" title="Rosin">Rosin</a>, another by-product of conifer tree resin, is widely used as an ingredient in a variety of industrial products, such as <a href="/wiki/Ink" title="Ink">inks</a>, <a href="/wiki/Varnish" title="Varnish">varnishes</a> and <a href="/wiki/Adhesive" title="Adhesive">adhesives</a>. Rosin is also used by violinists (and players of similar <a href="/wiki/Bow_(music)" title="Bow (music)">bowed</a> instruments) to increase friction on the <a href="/wiki/Bow_(music)" title="Bow (music)">bow</a> hair, by <a href="/wiki/Ballet_dancer" title="Ballet dancer">ballet dancers</a> on the soles of their shoes to maintain traction on the floor, by <a href="/wiki/Gymnastics" title="Gymnastics">gymnasts</a> to keep their grips while performing, and by <a href="/wiki/Baseball_pitcher" class="mw-redirect" title="Baseball pitcher">baseball pitchers</a> to improve their control of the baseball.<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> Terpenes are widely used as fragrances and flavors in consumer products such as <a href="/wiki/Perfume" title="Perfume">perfumes</a>, <a href="/wiki/Cosmetics" title="Cosmetics">cosmetics</a> and <a href="/wiki/Cleaning_agent" title="Cleaning agent">cleaning products</a>, as well as food and drink products. For example, the aroma and flavor of <a href="/wiki/Hops" title="Hops">hops</a> comes, in part, from <a href="/wiki/Sesquiterpene" title="Sesquiterpene">sesquiterpenes</a> (mainly <a href="/wiki/Alpha-humulene" class="mw-redirect" title="Alpha-humulene">α-humulene</a> and <a href="/wiki/Beta-caryophyllene" class="mw-redirect" title="Beta-caryophyllene">β-caryophyllene</a>), which affect <a href="/wiki/Beer" title="Beer">beer</a> quality.<sup id="cite_ref-beer_22-0" class="reference"><a href="#cite_note-beer-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> Some form hydroperoxides that are valued as catalysts in the production of polymers. </p><p>Many terpenes have been shown to have pharmacological effects, although most studies are from laboratory research, and <a href="/wiki/Clinical_research" title="Clinical research">clinical research</a> in humans is preliminary.<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> Terpenes are also components of some traditional medicines, such as <a href="/wiki/Aromatherapy" title="Aromatherapy">aromatherapy</a>.<sup id="cite_ref-24" class="reference"><a href="#cite_note-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> </p><p>Reflecting their defensive role in plants, terpenes are used as active ingredients of <a href="/wiki/Pesticide" title="Pesticide">pesticides</a> in agriculture.<sup id="cite_ref-25" class="reference"><a href="#cite_note-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> </p> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Tetrahydrocannabinol.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/4c/Tetrahydrocannabinol.svg/220px-Tetrahydrocannabinol.svg.png" decoding="async" width="220" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/4c/Tetrahydrocannabinol.svg/330px-Tetrahydrocannabinol.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/4c/Tetrahydrocannabinol.svg/440px-Tetrahydrocannabinol.svg.png 2x" data-file-width="620" data-file-height="337" /></a><figcaption><a href="/wiki/Tetrahydrocannabinol" title="Tetrahydrocannabinol">Tetrahydrocannabinol</a>, a terpenoid, not a terpene, is the active ingredient in marijuana.</figcaption></figure> <div class="mw-heading mw-heading2"><h2 id="Physical_and_chemical_properties">Physical and chemical properties</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Terpene&action=edit&section=4" title="Edit section: Physical and chemical properties"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Terpenes are colorless, although impure samples are often yellow. Boiling points scale with molecular size: terpenes, sesquiterpenes, and diterpenes respectively at 110, 160, and 220 °C. Being highly non-polar, they are insoluble in water. Being hydrocarbons, they are highly flammable and have low specific gravity (float on water). They are tactilely light oils considerably less <a href="/wiki/Viscosity" title="Viscosity">viscous</a> than familiar vegetable oils like corn oil (28 <a href="/wiki/Poise_(unit)" title="Poise (unit)">cP</a>), with viscosity ranging from 1 cP (à la water) to 6 cP. Terpenes are local irritants and can cause gastrointestinal disturbances if ingested. </p><p><i>Terpenoids</i> (mono-, sesqui-, di-, etc.) have similar physical properties but tend to be more polar and hence slightly more soluble in water and somewhat less volatile than their terpene analogues. Highly polar derivatives of terpenoids are the <a href="/wiki/Glycosides" class="mw-redirect" title="Glycosides">glycosides</a>, which are linked to sugars. These are water-soluble solids. </p> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951" /><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/Triterpene_glycoside" class="mw-redirect" title="Triterpene glycoside">Triterpene glycoside</a></div> <div class="mw-heading mw-heading2"><h2 id="Biosynthesis">Biosynthesis<span class="anchor" id="Biogenetic_isoprene_rule"></span></h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Terpene&action=edit&section=5" title="Edit section: Biosynthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:TerpeneVterpenoid.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/8d/TerpeneVterpenoid.svg/330px-TerpeneVterpenoid.svg.png" decoding="async" width="260" height="167" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/8d/TerpeneVterpenoid.svg/390px-TerpeneVterpenoid.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/8d/TerpeneVterpenoid.svg/520px-TerpeneVterpenoid.svg.png 2x" data-file-width="443" data-file-height="285" /></a><figcaption>Biosynthetic conversion of <a href="/wiki/Geranylpyrophosphate" class="mw-redirect" title="Geranylpyrophosphate">geranylpyrophosphate</a> to the terpenes <a href="/wiki/Alpha-pinene" class="mw-redirect" title="Alpha-pinene">α-pinene</a> and <a href="/wiki/Beta-pinene" class="mw-redirect" title="Beta-pinene">β-pinene</a> and to the terpinoid <a href="/wiki/Alpha-terpineol" class="mw-redirect" title="Alpha-terpineol">α-terpineol</a>.<sup id="cite_ref-Crot_2-2" class="reference"><a href="#cite_note-Crot-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="Isoprene_as_the_building_block">Isoprene as the building block</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Terpene&action=edit&section=6" title="Edit section: Isoprene as the building block"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Conceptually derived from <a href="/wiki/Isoprene" title="Isoprene">isoprenes</a>, the structures and formulas of terpenes follow the <b>biogenetic isoprene rule</b> or the <b>C<sub>5</sub> rule</b>, as described in 1953 by <a href="/wiki/Leopold_Ru%C5%BEi%C4%8Dka" title="Leopold Ružička">Leopold Ružička</a><sup id="cite_ref-ruzicka53_26-0" class="reference"><a href="#cite_note-ruzicka53-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> and colleagues.<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> The C<sub>5</sub> isoprene units are provided in the form of <a href="/wiki/Dimethylallyl_pyrophosphate" title="Dimethylallyl pyrophosphate">dimethylallyl pyrophosphate</a> (DMAPP) and <a href="/wiki/Isopentenyl_pyrophosphate" title="Isopentenyl pyrophosphate">isopentenyl pyrophosphate</a> (IPP). DMAPP and IPP are <a href="/wiki/Structural_isomer" title="Structural isomer">structural isomers</a> to each other. This pair of building blocks are produced by two distinct <a href="/wiki/Metabolic_pathway" title="Metabolic pathway">metabolic pathways</a>: the <a href="/wiki/Mevalonate_pathway" title="Mevalonate pathway">mevalonate (MVA) pathway</a> and the <a href="/wiki/Non-mevalonate_pathway" title="Non-mevalonate pathway">non-mevalonate (MEP) pathway</a>. These two pathways are mutually exclusive in most organisms, except for some bacteria and land plants.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (March 2021)">citation needed</span></a></i>]</sup> In general, most archaea and eukaryotes use the MVA pathway, while bacteria mostly have the MEP pathway. IPP and DMAPP are final products of both MVA and MEP pathways and the relative abundance of these two isoprene units is enzymatically regulated in host organisms. </p> <table class="wikitable"> <tbody><tr> <th>Organism </th> <th>Pathways </th></tr> <tr> <td><a href="/wiki/Bacteria" title="Bacteria">Bacteria</a></td> <td>MVA or MEP </td></tr> <tr> <td><a href="/wiki/Archaea" title="Archaea">Archaea</a></td> <td>MVA </td></tr> <tr> <td>Green <a href="/wiki/Algae" title="Algae">Algae</a></td> <td>MEP </td></tr> <tr> <td><a href="/wiki/Plant" title="Plant">Plants</a></td> <td>MVA and MEP </td></tr> <tr> <td><a href="/wiki/Animal" title="Animal">Animals</a></td> <td>MVA </td></tr> <tr> <td><a href="/wiki/Fungi" class="mw-redirect" title="Fungi">Fungi</a></td> <td>MVA </td></tr></tbody></table> <div class="mw-heading mw-heading4"><h4 id="Mevalonate_pathway">Mevalonate pathway</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Terpene&action=edit&section=7" title="Edit section: Mevalonate pathway"><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/Mevalonate_pathway" title="Mevalonate pathway">Mevalonate pathway</a></div> <p>This pathway conjugates three molecules of <a href="/wiki/Acetyl_CoA" class="mw-redirect" title="Acetyl CoA">acetyl CoA</a>. </p><p>The mevalonate (MVA) pathway is distributed in all three domains of life; archaea, bacteria and eukaryotes. The MVA pathway is universally distributed in archaea and non-photosynthetic eukaryotes, while the pathway is sparse in bacteria. In photosynthetic eukaryotes, some species possess the MVA pathway, while others have the MEP pathway or both MVA and MEP pathways. This is due to the acquisition of the MEP pathway by a common ancestor of <a href="/wiki/Archaeplastida" title="Archaeplastida">Archaeplastida</a> (algae + land plants) through the <a href="/wiki/Endosymbiont" title="Endosymbiont">endosymbiosis</a> of ancestral <a href="/wiki/Cyanobacteria" title="Cyanobacteria">cyanobacteria</a> that possessed the MEP pathway. The MVA and MEP pathways were selectively lost in individual photosynthetic lineages. </p><p>Also, the archaeal MVA pathway is not completely homologous to the eukaryotic MVA pathway.<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> Instead, the eukaryotic MVA pathway is closer to the bacterial MVA pathway. </p> <div class="mw-heading mw-heading4"><h4 id="Non-mevalonate_pathway">Non-mevalonate pathway</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Terpene&action=edit&section=8" title="Edit section: Non-mevalonate pathway"><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/Non-mevalonate_pathway" title="Non-mevalonate pathway">Non-mevalonate pathway</a></div> <p>The non-mevalonate pathway or the 2-<i>C</i>-methyl-D-erythritol 4-phosphate (MEP) pathway starts with <a href="/wiki/Pyruvate" class="mw-redirect" title="Pyruvate">pyruvate</a> and <a href="/wiki/Glyceraldehyde_3-phosphate" title="Glyceraldehyde 3-phosphate">glyceraldehyde 3-phosphate</a> (G3P) as the carbon source. </p><p>C<sub>5</sub> IPP and C<sub>5</sub> DMAPP are the end-products in either pathway and are the precursors of terpenoids with various carbon numbers (typically C<sub>5</sub> to C<sub>40</sub>), side chains of (bacterio)<a href="/wiki/Chlorophyll" title="Chlorophyll">chlorophylls</a>, <a href="/wiki/Heme" title="Heme">hemes</a> and <a href="/wiki/Quinone" title="Quinone">quinones</a>. Synthesis of all higher terpenoids proceeds via formation of <a href="/wiki/Geranyl_pyrophosphate" title="Geranyl pyrophosphate">geranyl pyrophosphate</a> (GPP), <a href="/wiki/Farnesyl_pyrophosphate" title="Farnesyl pyrophosphate">farnesyl pyrophosphate</a> (FPP), and <a href="/wiki/Geranylgeranyl_pyrophosphate" title="Geranylgeranyl pyrophosphate">geranylgeranyl pyrophosphate</a> (GGPP). </p> <div class="mw-heading mw-heading3"><h3 id="Geranyl_pyrophosphate_phase_and_beyond">Geranyl pyrophosphate phase and beyond</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Terpene&action=edit&section=9" title="Edit section: Geranyl pyrophosphate phase and beyond"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Synthesis_of_geranyl_pyrophosphate.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b2/Synthesis_of_geranyl_pyrophosphate.png/260px-Synthesis_of_geranyl_pyrophosphate.png" decoding="async" width="260" height="176" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b2/Synthesis_of_geranyl_pyrophosphate.png/390px-Synthesis_of_geranyl_pyrophosphate.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b2/Synthesis_of_geranyl_pyrophosphate.png/520px-Synthesis_of_geranyl_pyrophosphate.png 2x" data-file-width="2281" data-file-height="1545" /></a><figcaption><a href="/wiki/Isopentenyl_pyrophosphate" title="Isopentenyl pyrophosphate">Isopentenyl pyrophosphate</a> (IPP) and <a href="/wiki/Dimethylallyl_pyrophosphate" title="Dimethylallyl pyrophosphate">dimethylallyl pyrophosphate</a> (DMAPP) condense to produce <a href="/wiki/Geranyl_pyrophosphate" title="Geranyl pyrophosphate">geranyl pyrophosphate</a>, precursor to all terpenes and terpenoids.</figcaption></figure> <p>In both MVA and MEP pathways, IPP is isomerized to DMAPP by the enzyme isopentenyl pyrophosphate isomerase. IPP and DMAPP condense to give <a href="/wiki/Geranyl_pyrophosphate" title="Geranyl pyrophosphate">geranyl pyrophosphate</a>, the precursor to monoterpenes and monoterpenoids. </p><p>Geranyl pyrophosphate is also converted to <a href="/wiki/Farnesyl_pyrophosphate" title="Farnesyl pyrophosphate">farnesyl pyrophosphate</a> and <a href="/wiki/Geranylgeranyl_pyrophosphate" title="Geranylgeranyl pyrophosphate">geranylgeranyl pyrophosphate</a>, respectively C<sub>15</sub> and C<sub>20</sub> precursors to <a href="/wiki/Sesquiterpene" title="Sesquiterpene">sesquiterpenes</a> and <a href="/wiki/Diterpene" title="Diterpene">diterpenes</a> (as well as sesequiterpenoids and diterpenoids).<sup id="cite_ref-Crot_2-3" class="reference"><a href="#cite_note-Crot-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> Biosynthesis is mediated by <a href="/wiki/Terpene_synthase_N_terminal_domain" title="Terpene synthase N terminal domain">terpene synthase</a>.<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><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> <div class="mw-heading mw-heading3"><h3 id="Terpenes_to_terpenoids">Terpenes to terpenoids</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Terpene&action=edit&section=10" title="Edit section: Terpenes to terpenoids"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The genomes of many plant species contain genes that encode terpenoid synthase enzymes imparting terpenes with their basic structure, and <a href="/wiki/Cytochrome_P450" title="Cytochrome P450">cytochrome P450s</a> that modify this basic structure.<sup id="cite_ref-Crot_2-4" class="reference"><a href="#cite_note-Crot-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-boutanaev15_31-0" class="reference"><a href="#cite_note-boutanaev15-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Structure">Structure</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Terpene&action=edit&section=11" title="Edit section: Structure"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Terpenes can be visualized as the result of linking <a href="/wiki/Isoprene" title="Isoprene">isoprene</a> (C<sub>5</sub>H<sub>8</sub>) units "head to tail" to form chains and rings.<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> A few terpenes are linked “tail to tail”, and larger branched terpenes may be linked “tail to mid”. </p> <div class="mw-heading mw-heading3"><h3 id="Formula">Formula</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Terpene&action=edit&section=12" title="Edit section: Formula"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Strictly speaking all monoterpenes have the same chemical formula C<sub>10</sub>H<sub>16</sub>. Similarly all sesquiterpenes and diterpenes have formulas of C<sub>15</sub>H<sub>24</sub> and C<sub>20</sub>H<sub>32</sub> respectively. The structural diversity of mono-, sesqui-, and diterpenes is a consequence of isomerism. </p> <div class="mw-heading mw-heading3"><h3 id="Chirality">Chirality</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Terpene&action=edit&section=13" title="Edit section: Chirality"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Terpenes and terpenoids are usually <a href="/wiki/Chiral" class="mw-redirect" title="Chiral">chiral</a>. Chiral compounds can exist as non-superposable mirror images, which exhibit distinct <a href="/wiki/Physical_properties" class="mw-redirect" title="Physical properties">physical properties</a> such as odor or toxicity. </p> <div class="mw-heading mw-heading4"><h4 id="Unsaturation">Unsaturation</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Terpene&action=edit&section=14" title="Edit section: Unsaturation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Most terpenes and terpenoids feature C=C groups, i.e. they exhibit unsaturation. Since they carry no functional groups aside from their unsaturation, terpenes are structurally distinctive. The unsaturation is associated with di- and trisubstituted <a href="/wiki/Alkenes" class="mw-redirect" title="Alkenes">alkenes</a>. Di- and trisubstituted alkenes resist polymerization (low <a href="/wiki/Ceiling_temperature" title="Ceiling temperature">ceiling temperatures</a>) but are susceptible to acid-induced <a href="/wiki/Carbocation" title="Carbocation">carbocation</a> formation. </p> <div class="mw-heading mw-heading3"><h3 id="Classification">Classification</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Terpene&action=edit&section=15" title="Edit section: Classification"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul class="gallery mw-gallery-traditional"> <li class="gallerycaption">Selected terpenes</li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Limonene-2D-skeletal.svg" class="mw-file-description" title="Limonene, a monoterpene."><img alt="Limonene, a monoterpene." src="//upload.wikimedia.org/wikipedia/commons/thumb/7/76/Limonene-2D-skeletal.svg/49px-Limonene-2D-skeletal.svg.png" decoding="async" width="49" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/76/Limonene-2D-skeletal.svg/73px-Limonene-2D-skeletal.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/76/Limonene-2D-skeletal.svg/98px-Limonene-2D-skeletal.svg.png 2x" data-file-width="769" data-file-height="1881" /></a></span></div> <div class="gallerytext"><a href="/wiki/Limonene" title="Limonene">Limonene</a>, a <a href="/wiki/Monoterpene" title="Monoterpene">monoterpene</a>.</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Carvone.svg" class="mw-file-description" title="Carvone is a monoterpenoid, a modified monoterpene."><img alt="Carvone is a monoterpenoid, a modified monoterpene." src="//upload.wikimedia.org/wikipedia/commons/thumb/b/bf/Carvone.svg/120px-Carvone.svg.png" decoding="async" width="120" height="93" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/bf/Carvone.svg/180px-Carvone.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/bf/Carvone.svg/240px-Carvone.svg.png 2x" data-file-width="433" data-file-height="335" /></a></span></div> <div class="gallerytext"><a href="/wiki/Carvone" title="Carvone">Carvone</a> is a monoterpenoid, a modified monoterpene.</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Alpha-pinen.svg" class="mw-file-description" title="Pinene, a monoterpene which exists as two isomers, is a major consistituent of turpentine."><img alt="Pinene, a monoterpene which exists as two isomers, is a major consistituent of turpentine." src="//upload.wikimedia.org/wikipedia/commons/thumb/6/69/Alpha-pinen.svg/103px-Alpha-pinen.svg.png" decoding="async" width="103" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/69/Alpha-pinen.svg/154px-Alpha-pinen.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/69/Alpha-pinen.svg/205px-Alpha-pinen.svg.png 2x" data-file-width="662" data-file-height="773" /></a></span></div> <div class="gallerytext"><a href="/wiki/Pinene" title="Pinene">Pinene</a>, a monoterpene which exists as two isomers, is a major consistituent of <a href="/wiki/Turpentine" title="Turpentine">turpentine</a>.</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Beta-thujaplicin.png" class="mw-file-description" title="Hinokitiol is a monoterpenoid, a tropolone derivative."><img alt="Hinokitiol is a monoterpenoid, a tropolone derivative." src="//upload.wikimedia.org/wikipedia/commons/thumb/5/5f/Beta-thujaplicin.png/120px-Beta-thujaplicin.png" decoding="async" width="120" height="89" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/5f/Beta-thujaplicin.png/180px-Beta-thujaplicin.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/5f/Beta-thujaplicin.png/240px-Beta-thujaplicin.png 2x" data-file-width="607" data-file-height="451" /></a></span></div> <div class="gallerytext"><a href="/wiki/Hinokitiol" title="Hinokitiol">Hinokitiol</a> is a monoterpenoid, a <a href="/wiki/Tropolone" title="Tropolone">tropolone</a> derivative.</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Humulene.png" class="mw-file-description" title="Humulene, a sesquiterpene."><img alt="Humulene, a sesquiterpene." src="//upload.wikimedia.org/wikipedia/commons/thumb/1/13/Humulene.png/120px-Humulene.png" decoding="async" width="120" height="106" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/13/Humulene.png/180px-Humulene.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/13/Humulene.png/240px-Humulene.png 2x" data-file-width="1208" data-file-height="1063" /></a></span></div> <div class="gallerytext"><a href="/wiki/Humulene" title="Humulene">Humulene</a>, a <a href="/wiki/Sesquiterpene" title="Sesquiterpene">sesquiterpene</a>.</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Taxadiene.svg" class="mw-file-description" title="Taxadiene, a diterpene, precursor to the diterpenoid taxol, an anticancer agent."><img alt="Taxadiene, a diterpene, precursor to the diterpenoid taxol, an anticancer agent." src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d7/Taxadiene.svg/120px-Taxadiene.svg.png" decoding="async" width="120" height="77" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d7/Taxadiene.svg/180px-Taxadiene.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d7/Taxadiene.svg/240px-Taxadiene.svg.png 2x" data-file-width="512" data-file-height="327" /></a></span></div> <div class="gallerytext"><a href="/wiki/Taxadiene" title="Taxadiene">Taxadiene</a>, a <a href="/wiki/Diterpene" title="Diterpene">diterpene</a>, precursor to the diterpenoid <a href="/wiki/Taxol" class="mw-redirect" title="Taxol">taxol</a>, an anticancer agent.</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Squalene.svg" class="mw-file-description" title="Squalene, a triterpene and universal precursor to natural steroids."><img alt="Squalene, a triterpene and universal precursor to natural steroids." src="//upload.wikimedia.org/wikipedia/commons/thumb/2/24/Squalene.svg/120px-Squalene.svg.png" decoding="async" width="120" height="20" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/24/Squalene.svg/180px-Squalene.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/24/Squalene.svg/240px-Squalene.svg.png 2x" data-file-width="420" data-file-height="70" /></a></span></div> <div class="gallerytext"><a href="/wiki/Squalene" title="Squalene">Squalene</a>, a <a href="/wiki/Triterpene" title="Triterpene">triterpene</a> and universal precursor to natural <a href="/wiki/Steroid" title="Steroid">steroids</a>.</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Geosmin_Structural_Formulae.svg" class="mw-file-description" title="Geosmin is a sesquiterpenoid."><img alt="Geosmin is a sesquiterpenoid." src="//upload.wikimedia.org/wikipedia/commons/thumb/2/2a/Geosmin_Structural_Formulae.svg/100px-Geosmin_Structural_Formulae.svg.png" decoding="async" width="100" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/2a/Geosmin_Structural_Formulae.svg/149px-Geosmin_Structural_Formulae.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/2a/Geosmin_Structural_Formulae.svg/199px-Geosmin_Structural_Formulae.svg.png 2x" data-file-width="235" data-file-height="283" /></a></span></div> <div class="gallerytext"><a href="/wiki/Geosmin" title="Geosmin">Geosmin</a> is a sesquiterpenoid.</div> </li> </ul> <p>Terpenes may be classified by the number of isoprene units in the molecule; a prefix in the name indicates the number of isoprene pairs needed to assemble the molecule. Commonly, terpenes contain 2, 3, 4 or 6 isoprene units; the tetraterpenes (8 isoprene units) form a separate class of compounds called carotenoids; the others are rare. </p> <ul><li>The basic unit isoprene itself is a hemiterpene. It may form oxygen-containing derivatives such as <a href="/wiki/Prenol" title="Prenol">prenol</a> and <a href="/wiki/Isovaleric_acid" title="Isovaleric acid">isovaleric acid</a> analogous to terpenoids.</li> <li><a href="/wiki/Monoterpenes" class="mw-redirect" title="Monoterpenes">Monoterpenes</a> consist of <i>two isoprene</i> units and have the molecular formula C<sub>10</sub>H<sub>16</sub>. Examples of monoterpenes and monoterpenoids include <a href="/wiki/Geraniol" title="Geraniol">geraniol</a>, <a href="/wiki/Terpineol" title="Terpineol">terpineol</a> (present in <a href="/wiki/Lilac" class="mw-redirect" title="Lilac">lilacs</a>), <a href="/wiki/Limonene" title="Limonene">limonene</a> (present in citrus fruits), <a href="/wiki/Myrcene" title="Myrcene">myrcene</a> (present in <a href="/wiki/Hops" title="Hops">hops</a>), <a href="/wiki/Linalool" title="Linalool">linalool</a> (present in <a href="/wiki/Lavandula" title="Lavandula">lavender</a>), <a href="/wiki/Hinokitiol" title="Hinokitiol">hinokitiol</a> (present in <a href="/wiki/Cypress" title="Cypress">cypress</a> trees) or <a href="/wiki/Pinene" title="Pinene">pinene</a> (present in <a href="/wiki/Pine" title="Pine">pine</a> trees).<sup id="cite_ref-33" class="reference"><a href="#cite_note-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Terpenes_34-0" class="reference"><a href="#cite_note-Terpenes-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Iridoids" class="mw-redirect" title="Iridoids">Iridoids</a> derive from monoterpenes. Examples of iridoids include <a href="/wiki/Aucubin" title="Aucubin">aucubin</a> and <a href="/wiki/Catalpol" title="Catalpol">catalpol</a>.</li> <li><a href="/wiki/Sesquiterpenes" class="mw-redirect" title="Sesquiterpenes">Sesquiterpenes</a> consist of <i>three isoprene</i> units and have the molecular formula C<sub>15</sub>H<sub>24</sub>. Examples of sesquiterpenes and sesquiterpenoids include <a href="/wiki/Humulene" title="Humulene">humulene</a>, <a href="/wiki/Farnesene" title="Farnesene">farnesenes</a>, <a href="/wiki/Farnesol" title="Farnesol">farnesol</a>, <a href="/wiki/Geosmin" title="Geosmin">geosmin</a>.<sup id="cite_ref-Terpenes_34-1" class="reference"><a href="#cite_note-Terpenes-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> (The <i>sesqui-</i> prefix means one and a half.)</li> <li><a href="/wiki/Diterpenes" class="mw-redirect" title="Diterpenes">Diterpenes</a> are composed of <i>four isoprene</i> units and have the molecular formula C<sub>20</sub>H<sub>32</sub>. They derive from <a href="/wiki/Geranylgeranyl_pyrophosphate" title="Geranylgeranyl pyrophosphate">geranylgeranyl pyrophosphate</a>. Examples of diterpenes and diterpenoids are <a href="/wiki/Cafestol" title="Cafestol">cafestol</a>, <a href="/wiki/Kahweol" title="Kahweol">kahweol</a>, <a href="/wiki/Cembrene" class="mw-redirect" title="Cembrene">cembrene</a> and <a href="/wiki/Taxadiene" title="Taxadiene">taxadiene</a> (precursor of <a href="/wiki/Taxol" class="mw-redirect" title="Taxol">taxol</a>). Diterpenes also form the basis for biologically important compounds such as <a href="/wiki/Retinol" title="Retinol">retinol</a>, <a href="/wiki/Retinal" title="Retinal">retinal</a>, and <a href="/wiki/Phytol" title="Phytol">phytol</a>.</li> <li>Sesterterpenes, terpenes having 25 carbons and <i>five isoprene</i> units, are rare relative to the other sizes. (The <i>sester-</i> prefix means two and a half.) An example of a sesterterpenoid is <a href="/w/index.php?title=Geranylfarnesol&action=edit&redlink=1" class="new" title="Geranylfarnesol (page does not exist)">geranylfarnesol</a>.</li> <li><a href="/wiki/Triterpene" title="Triterpene">Triterpenes</a> consist of <i>six isoprene</i> units and have the molecular formula C<sub>30</sub>H<sub>48</sub>. The linear triterpene <a href="/wiki/Squalene" title="Squalene">squalene</a>, the major constituent of <a href="/wiki/Shark_liver_oil" title="Shark liver oil">shark liver oil</a>, is derived from the reductive coupling of two molecules of <a href="/wiki/Farnesyl_pyrophosphate" title="Farnesyl pyrophosphate">farnesyl pyrophosphate</a>. Squalene is then processed biosynthetically to generate either <a href="/wiki/Lanosterol" title="Lanosterol">lanosterol</a> or <a href="/wiki/Cycloartenol" title="Cycloartenol">cycloartenol</a>, the structural precursors to all the <a href="/wiki/Steroid" title="Steroid">steroids</a>.</li> <li>Sesquarterpenes are composed of <i>seven isoprene</i> units and have the molecular formula C<sub>35</sub>H<sub>56</sub>. Sesquarterpenes are typically microbial in their origin. Examples of sesquarterpenoids are ferrugicadiol and tetraprenylcurcumene.</li> <li><a href="/wiki/Tetraterpene" title="Tetraterpene">Tetraterpenes</a> contain <i>eight isoprene</i> units and have the molecular formula C<sub>40</sub>H<sub>64</sub>. Biologically important tetraterpenoids include the acyclic <a href="/wiki/Lycopene" title="Lycopene">lycopene</a>, the monocyclic <a href="/wiki/Gamma-carotene" class="mw-redirect" title="Gamma-carotene">gamma-carotene</a>, and the bicyclic <a href="/wiki/Alpha-carotene" class="mw-redirect" title="Alpha-carotene">alpha-</a> and <a href="/wiki/Beta-carotene" class="mw-redirect" title="Beta-carotene">beta-carotenes</a>.</li> <li>Polyterpenes consist of long chains of <i>many isoprene</i> units. Natural <a href="/wiki/Rubber" class="mw-redirect" title="Rubber">rubber</a> consists of polyisoprene in which the double bonds are <a href="/wiki/Cis%E2%80%93trans_isomerism" title="Cis–trans isomerism"><i>cis</i></a>. Some plants produce a polyisoprene with <i>trans</i> double bonds, known as <a href="/wiki/Gutta-percha" title="Gutta-percha">gutta-percha</a>.</li> <li>Norisoprenoids, characterized by the shortening of a chain or ring by the removal of a methylene group or substitution of one or more methyl side chains by hydrogen atoms. These include the C<sub>13</sub>-norisoprenoid 3-oxo-α-ionol present in <a href="/wiki/Muscat_of_Alexandria" title="Muscat of Alexandria">Muscat of Alexandria</a> leaves and 7,8-dihydroionone derivatives, such as megastigmane-3,9-diol and 3-oxo-7,8-dihydro-α-ionol found in <a href="/wiki/Shiraz_(grape)" class="mw-redirect" title="Shiraz (grape)">Shiraz</a> leaves (both grapes in the species <i><a href="/wiki/Vitis_vinifera" title="Vitis vinifera">Vitis vinifera</a></i>)<sup id="cite_ref-35" class="reference"><a href="#cite_note-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> or <a href="/wiki/Wine" title="Wine">wine</a><sup id="cite_ref-36" class="reference"><a href="#cite_note-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-37" class="reference"><a href="#cite_note-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup> (responsible for some of the <a href="/wiki/Aroma_of_wine" title="Aroma of wine">spice notes</a> in <a href="/wiki/Chardonnay" title="Chardonnay">Chardonnay</a>), can be produced by fungal <a href="/wiki/Peroxidase" title="Peroxidase">peroxidases</a><sup id="cite_ref-38" class="reference"><a href="#cite_note-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup> or <a href="/wiki/Glycosidase" class="mw-redirect" title="Glycosidase">glycosidases</a>.<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></li></ul> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Osmeterium.JPG" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f5/Osmeterium.JPG/220px-Osmeterium.JPG" decoding="async" width="220" height="165" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f5/Osmeterium.JPG/330px-Osmeterium.JPG 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f5/Osmeterium.JPG/440px-Osmeterium.JPG 2x" data-file-width="894" data-file-height="669" /></a><figcaption>Second- or third-<a href="/wiki/Instar" title="Instar">instar</a> caterpillars of Genus <i><a href="/wiki/Papilio" title="Papilio">Papilio</a></i> butterflies, like this <i><a href="/wiki/Papilio_glaucus" title="Papilio glaucus">Papilio glaucus</a></i>, emit terpenes from their <a href="/wiki/Osmeterium" title="Osmeterium">osmeterium</a>.</figcaption></figure> <div class="mw-heading mw-heading2"><h2 id="Industrial_syntheses">Industrial syntheses</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Terpene&action=edit&section=16" title="Edit section: Industrial syntheses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>While terpenes and terpenoids occur widely, their extraction from natural sources is often problematic. Consequently, they are produced by chemical synthesis, usually from <a href="/wiki/Petrochemical" title="Petrochemical">petrochemicals</a>. In one route, <a href="/wiki/Acetone" title="Acetone">acetone</a> and <a href="/wiki/Acetylene" title="Acetylene">acetylene</a> are condensed to give <a href="/wiki/2-Methylbut-3-yn-2-ol" title="2-Methylbut-3-yn-2-ol">2-Methylbut-3-yn-2-ol</a>, which is extended with <a href="/wiki/Acetoacetic_ester" class="mw-redirect" title="Acetoacetic ester">acetoacetic ester</a> to give <a href="/wiki/Geraniol" title="Geraniol">geranyl alcohol</a>. Others are prepared from those terpenes and terpenoids that are readily isolated in quantity, say from the paper and <a href="/wiki/Tall_oil" title="Tall oil">tall oil</a> industries. For example, <a href="/wiki/Alpha-Pinene" class="mw-redirect" title="Alpha-Pinene">α-pinene</a>, which is readily obtainable from natural sources, is converted to <a href="/wiki/Citronellal" title="Citronellal">citronellal</a> and <a href="/wiki/Camphor" title="Camphor">camphor</a>. Citronellal is also converted to <a href="/wiki/Rose_oxide" title="Rose oxide">rose oxide</a> and <a href="/wiki/Menthol" title="Menthol">menthol</a>.<sup id="cite_ref-book_1-1" class="reference"><a href="#cite_note-book-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:IndustrialRouteGeranylAlc.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/cb/IndustrialRouteGeranylAlc.png/424px-IndustrialRouteGeranylAlc.png" decoding="async" width="424" height="77" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/cb/IndustrialRouteGeranylAlc.png/636px-IndustrialRouteGeranylAlc.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/cb/IndustrialRouteGeranylAlc.png/848px-IndustrialRouteGeranylAlc.png 2x" data-file-width="3002" data-file-height="548" /></a><figcaption>Summary of an industrial route to geranyl alcohol from simple reagents (wrong arrow. this is not a retrosynthesis)</figcaption></figure> <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=Terpene&action=edit&section=17" 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-book-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-book_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-book_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 a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFEberhard_Breitmaier2006" class="citation book cs1">Eberhard Breitmaier (2006). <i>Terpenes: Flavors, Fragrances, Pharmaca, Pheromones</i>. Wiley-VCH. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F9783527609949">10.1002/9783527609949</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9783527609949" title="Special:BookSources/9783527609949"><bdi>9783527609949</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Terpenes%3A+Flavors%2C+Fragrances%2C+Pharmaca%2C+Pheromones&rft.pub=Wiley-VCH&rft.date=2006&rft_id=info%3Adoi%2F10.1002%2F9783527609949&rft.isbn=9783527609949&rft.au=Eberhard+Breitmaier&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATerpene" class="Z3988"></span></span> </li> <li id="cite_note-Crot-2"><span class="mw-cite-backlink">^ <a href="#cite_ref-Crot_2-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Crot_2-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Crot_2-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-Crot_2-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-Crot_2-4"><sup><i><b>e</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFDavis,_Edward_M.Croteau,_Rodney2000" class="citation book cs1">Davis, Edward M.; Croteau, Rodney (2000). "Cyclization enzymes in the biosynthesis of monoterpenes, sesquiterpenes, and diterpenes". <i>Biosynthesis</i>. Vol. 209. pp. <span class="nowrap">53–</span>95. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2F3-540-48146-X_2">10.1007/3-540-48146-X_2</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-540-66573-1" title="Special:BookSources/978-3-540-66573-1"><bdi>978-3-540-66573-1</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Cyclization+enzymes+in+the+biosynthesis+of+monoterpenes%2C+sesquiterpenes%2C+and+diterpenes&rft.btitle=Biosynthesis&rft.pages=%3Cspan+class%3D%22nowrap%22%3E53-%3C%2Fspan%3E95&rft.date=2000&rft_id=info%3Adoi%2F10.1007%2F3-540-48146-X_2&rft.isbn=978-3-540-66573-1&rft.au=Davis%2C+Edward+M.&rft.au=Croteau%2C+Rodney&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATerpene" class="Z3988"></span> <span class="cs1-visible-error citation-comment"><code class="cs1-code">{{<a href="/wiki/Template:Cite_book" title="Template:Cite book">cite book</a>}}</code>: </span><span class="cs1-visible-error citation-comment"><code class="cs1-code">|journal=</code> ignored (<a href="/wiki/Help:CS1_errors#periodical_ignored" title="Help:CS1 errors">help</a>)</span></span> </li> <li id="cite_note-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-3">^</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://rareterpenes.com/what-are-terpenes-an-overview/">"What are Terpenes"</a>. <i>rareterpenes.com</i>. 13 April 2021.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=rareterpenes.com&rft.atitle=What+are+Terpenes&rft.date=2021-04-13&rft_id=https%3A%2F%2Frareterpenes.com%2Fwhat-are-terpenes-an-overview%2F&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATerpene" class="Z3988"></span></span> </li> <li id="cite_note-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-4">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFStoker2007" class="citation book cs1">Stoker, H. Stephen (2007). <i>General, Organic, and Biological Chemistry, 4th edition</i>. Houghton Mifflin Company. p. 337. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-618-73063-6" title="Special:BookSources/978-0-618-73063-6"><bdi>978-0-618-73063-6</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=General%2C+Organic%2C+and+Biological+Chemistry%2C+4th+edition&rft.pages=337&rft.pub=Houghton+Mifflin+Company&rft.date=2007&rft.isbn=978-0-618-73063-6&rft.aulast=Stoker&rft.aufirst=H.+Stephen&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATerpene" class="Z3988"></span></span> </li> <li id="cite_note-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-5">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFKekulé1866" class="citation book cs1 cs1-prop-foreign-lang-source">Kekulé, August (1866). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=IbBmZDznuPsC&pg=PA464"><i>Lehrbuch der organischen Chemie</i></a> [<i>Textbook of Organic Chemistry</i>] (in German). Vol. 2. Erlangen, (Germany): Ferdinand Enke. pp. <span class="nowrap">464–</span>465. <q>From pp. 464–465: <i>"Mit dem Namen Terpene bezeichnen wir … unter verschiedenen Namen aufgeführt werden."</i> (By the name "terpene" we designate in general the hydrocarbons composed according to the [empirical] formula C<sub>10</sub>H<sub>16</sub> (see §. 1540)</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Lehrbuch+der+organischen+Chemie&rft.place=Erlangen%2C+%28Germany%29&rft.pages=%3Cspan+class%3D%22nowrap%22%3E464-%3C%2Fspan%3E465&rft.pub=Ferdinand+Enke&rft.date=1866&rft.aulast=Kekul%C3%A9&rft.aufirst=August&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DIbBmZDznuPsC%26pg%3DPA464&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATerpene" class="Z3988"></span></span> </li> <li id="cite_note-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-6">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFDev1989" class="citation book cs1">Dev, Sukh (1989). "Chapter 8. Isoprenoids: 8.1. Terpenoids.". In Rowe, John W. (ed.). <i>Natural Products of Woody Plants: Chemicals Extraneous to the Lignocellulosic Cell Wall</i>. Berlin and Heidelberg, Germany: Springer-Verlag. pp. <span class="nowrap">691–</span>807.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Chapter+8.+Isoprenoids%3A+8.1.+Terpenoids.&rft.btitle=Natural+Products+of+Woody+Plants%3A+Chemicals+Extraneous+to+the+Lignocellulosic+Cell+Wall&rft.place=Berlin+and+Heidelberg%2C+Germany&rft.pages=%3Cspan+class%3D%22nowrap%22%3E691-%3C%2Fspan%3E807&rft.pub=Springer-Verlag&rft.date=1989&rft.aulast=Dev&rft.aufirst=Sukh&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATerpene" class="Z3988"></span> ; <a rel="nofollow" class="external text" href="https://link.springer.com/chapter/10.1007/978-3-642-74075-6_19">see p. 691.</a></span> </li> <li id="cite_note-Ull-7"><span class="mw-cite-backlink">^ <a href="#cite_ref-Ull_7-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Ull_7-1"><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="CITEREFEggersdorfer2000" class="citation encyclopaedia cs1">Eggersdorfer, Manfred (2000). "Terpenes". <i><a href="/wiki/Ullmann%27s_Encyclopedia_of_Industrial_Chemistry" title="Ullmann's Encyclopedia of Industrial Chemistry">Ullmann's Encyclopedia of Industrial Chemistry</a></i>. Weinheim: Wiley-VCH. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F14356007.a26_205">10.1002/14356007.a26_205</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-527-30673-2" title="Special:BookSources/978-3-527-30673-2"><bdi>978-3-527-30673-2</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Terpenes&rft.btitle=Ullmann%27s+Encyclopedia+of+Industrial+Chemistry&rft.place=Weinheim&rft.pub=Wiley-VCH&rft.date=2000&rft_id=info%3Adoi%2F10.1002%2F14356007.a26_205&rft.isbn=978-3-527-30673-2&rft.aulast=Eggersdorfer&rft.aufirst=Manfred&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATerpene" class="Z3988"></span></span> </li> <li id="cite_note-8"><span class="mw-cite-backlink"><b><a href="#cite_ref-8">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation journal cs1"><a rel="nofollow" class="external text" href="https://goldbook.iupac.org/html/T/T06279.html">"IUPAC Gold Book - terpenoids"</a>. <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/10.1351%2Fgoldbook.T06279">10.1351/goldbook.T06279</a></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=IUPAC+Gold+Book+-+terpenoids&rft_id=info%3Adoi%2F10.1351%2Fgoldbook.T06279&rft_id=https%3A%2F%2Fgoldbook.iupac.org%2Fhtml%2FT%2FT06279.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATerpene" class="Z3988"></span> <span class="cs1-visible-error citation-comment"><code class="cs1-code">{{<a href="/wiki/Template:Cite_journal" title="Template:Cite journal">cite journal</a>}}</code>: </span><span class="cs1-visible-error citation-comment">Cite journal requires <code class="cs1-code">|journal=</code> (<a href="/wiki/Help:CS1_errors#missing_periodical" title="Help:CS1 errors">help</a>)</span></span> </li> <li id="cite_note-9"><span class="mw-cite-backlink"><b><a href="#cite_ref-9">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFChenBaran2009" class="citation journal cs1">Chen, Ke; Baran, Phil S. (June 2009). "Total synthesis of eudesmane terpenes by site-selective C–H oxidations". <i>Nature</i>. <b>459</b> (7248): <span class="nowrap">824–</span>828. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2009Natur.459..824C">2009Natur.459..824C</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1038%2Fnature08043">10.1038/nature08043</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/19440196">19440196</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:4312428">4312428</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Nature&rft.atitle=Total+synthesis+of+eudesmane+terpenes+by+site-selective+C%E2%80%93H+oxidations&rft.volume=459&rft.issue=7248&rft.pages=%3Cspan+class%3D%22nowrap%22%3E824-%3C%2Fspan%3E828&rft.date=2009-06&rft_id=info%3Adoi%2F10.1038%2Fnature08043&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A4312428%23id-name%3DS2CID&rft_id=info%3Apmid%2F19440196&rft_id=info%3Abibcode%2F2009Natur.459..824C&rft.aulast=Chen&rft.aufirst=Ke&rft.au=Baran%2C+Phil+S.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATerpene" class="Z3988"></span></span> </li> <li id="cite_note-Nobel-10"><span class="mw-cite-backlink"><b><a href="#cite_ref-Nobel_10-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFGrandin1966" class="citation book cs1">Grandin, Karl, ed. (1966). "Leopold Ružička". <i>Nobel Lectures, Chemistry: 1922-1941</i>. 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"Generation of Norisoprenoid Flavors from Carotenoids by Fungal Peroxidases". <i>Journal of Agricultural and Food Chemistry</i>. <b>57</b> (21): <span class="nowrap">9951–</span>9955. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fjf901438m">10.1021/jf901438m</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/19817422">19817422</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Agricultural+and+Food+Chemistry&rft.atitle=Generation+of+Norisoprenoid+Flavors+from+Carotenoids+by+Fungal+Peroxidases&rft.volume=57&rft.issue=21&rft.pages=%3Cspan+class%3D%22nowrap%22%3E9951-%3C%2Fspan%3E9955&rft.date=2009&rft_id=info%3Adoi%2F10.1021%2Fjf901438m&rft_id=info%3Apmid%2F19817422&rft.aulast=Zelena&rft.aufirst=K.&rft.au=Hardebusch%2C+B.&rft.au=H%C3%BClsdau%2C+B.&rft.au=Berger%2C+R.+G.&rft.au=Zorn%2C+H.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATerpene" class="Z3988"></span></span> </li> <li id="cite_note-39"><span class="mw-cite-backlink"><b><a href="#cite_ref-39">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFCabaroğluSelliCanbaşLepoutre2003" class="citation journal cs1">Cabaroğlu, T.; Selli, S.; Canbaş, A.; Lepoutre, J.-P.; Günata, Z. 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"Wine flavor enhancement through the use of exogenous fungal glycosidases". <i>Enzyme and Microbial Technology</i>. <b>33</b> (5): <span class="nowrap">581–</span>587. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FS0141-0229%2803%2900179-0">10.1016/S0141-0229(03)00179-0</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Enzyme+and+Microbial+Technology&rft.atitle=Wine+flavor+enhancement+through+the+use+of+exogenous+fungal+glycosidases&rft.volume=33&rft.issue=5&rft.pages=%3Cspan+class%3D%22nowrap%22%3E581-%3C%2Fspan%3E587&rft.date=2003&rft_id=info%3Adoi%2F10.1016%2FS0141-0229%2803%2900179-0&rft.aulast=Cabaro%C4%9Flu&rft.aufirst=T.&rft.au=Selli%2C+S.&rft.au=Canba%C5%9F%2C+A.&rft.au=Lepoutre%2C+J.-P.&rft.au=G%C3%BCnata%2C+Z.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATerpene" class="Z3988"></span></span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Terpene&action=edit&section=18" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1235681985">.mw-parser-output .side-box{margin:4px 0;box-sizing:border-box;border:1px solid #aaa;font-size:88%;line-height:1.25em;background-color:var(--background-color-interactive-subtle,#f8f9fa);display:flow-root}.mw-parser-output .side-box-abovebelow,.mw-parser-output .side-box-text{padding:0.25em 0.9em}.mw-parser-output .side-box-image{padding:2px 0 2px 0.9em;text-align:center}.mw-parser-output .side-box-imageright{padding:2px 0.9em 2px 0;text-align:center}@media(min-width:500px){.mw-parser-output .side-box-flex{display:flex;align-items:center}.mw-parser-output .side-box-text{flex:1;min-width:0}}@media(min-width:720px){.mw-parser-output .side-box{width:238px}.mw-parser-output .side-box-right{clear:right;float:right;margin-left:1em}.mw-parser-output .side-box-left{margin-right:1em}}</style><style data-mw-deduplicate="TemplateStyles:r1237033735">@media print{body.ns-0 .mw-parser-output .sistersitebox{display:none!important}}@media screen{html.skin-theme-clientpref-night .mw-parser-output .sistersitebox img[src*="Wiktionary-logo-en-v2.svg"]{background-color:white}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .sistersitebox img[src*="Wiktionary-logo-en-v2.svg"]{background-color:white}}</style><div class="side-box side-box-right plainlinks sistersitebox"><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style> <div class="side-box-flex"> <div class="side-box-image"><span class="noviewer" typeof="mw:File"><a href="/wiki/File:Commons-logo.svg" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/40px-Commons-logo.svg.png" decoding="async" width="30" height="40" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/60px-Commons-logo.svg.png 1.5x" data-file-width="1024" data-file-height="1376" /></a></span></div> <div class="side-box-text plainlist">Wikimedia Commons has media related to <a href="https://commons.wikimedia.org/wiki/Terpenes" class="extiw" title="commons:Terpenes"><span style="font-style:italic; font-weight:bold;">Terpenes</span></a>.</div></div> </div> <ul><li><a rel="nofollow" class="external text" href="https://meshb.nlm.nih.gov/record/ui?name=Terpenes">Terpenes</a> at the U.S. National Library of Medicine <a href="/wiki/Medical_Subject_Headings" title="Medical Subject Headings">Medical Subject Headings</a> (MeSH)</li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFPope1911" class="citation encyclopaedia cs1">Pope, Frank George (1911). <span class="cs1-ws-icon" title="s:1911 Encyclopædia Britannica/Terpenes"><a class="external text" href="https://en.wikisource.org/wiki/1911_Encyclop%C3%A6dia_Britannica/Terpenes">"Terpenes" </a></span>. In <a href="/wiki/Hugh_Chisholm" title="Hugh Chisholm">Chisholm, Hugh</a> (ed.). <i><a href="/wiki/Encyclop%C3%A6dia_Britannica_Eleventh_Edition" title="Encyclopædia Britannica Eleventh Edition">Encyclopædia Britannica</a></i>. Vol. 26 (11th ed.). Cambridge University Press. pp. <span class="nowrap">647–</span>652.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Terpenes&rft.btitle=Encyclop%C3%A6dia+Britannica&rft.pages=%3Cspan+class%3D%22nowrap%22%3E647-%3C%2Fspan%3E652&rft.edition=11th&rft.pub=Cambridge+University+Press&rft.date=1911&rft.aulast=Pope&rft.aufirst=Frank+George&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATerpene" class="Z3988"></span> Survey of terpene chemistry.</li></ul> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output .hlist.inline,.mw-parser-output .hlist.inline dl,.mw-parser-output .hlist.inline ol,.mw-parser-output .hlist.inline ul,.mw-parser-output .hlist dl dl,.mw-parser-output .hlist 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.navbar-brackets::after{margin-left:-0.125em;content:" ]"}.mw-parser-output .navbar li{word-spacing:-0.125em}.mw-parser-output .navbar a>span,.mw-parser-output .navbar a>abbr{text-decoration:inherit}.mw-parser-output .navbar-mini abbr{font-variant:small-caps;border-bottom:none;text-decoration:none;cursor:inherit}.mw-parser-output .navbar-ct-full{font-size:114%;margin:0 7em}.mw-parser-output .navbar-ct-mini{font-size:114%;margin:0 4em}html.skin-theme-clientpref-night .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}@media(prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}}@media print{.mw-parser-output .navbar{display:none!important}}</style><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template: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)435" style="font-size:114%;margin:0 4em">Types of <a class="mw-selflink selflink">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" aria-labelledby="Terpenes20" 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:Terpenes" title="Template:Terpenes"><abbr title="View this 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exist)">α-Ylangene</a></li> <li><a href="/wiki/Copaene" title="Copaene">α-Copaene</a></li> <li><a href="/w/index.php?title=Aromadendrene&action=edit&redlink=1" class="new" title="Aromadendrene (page does not exist)">Aromadendrene</a></li> <li><a href="/w/index.php?title=Eremophilene&action=edit&redlink=1" class="new" title="Eremophilene (page does not exist)">Eremophilene</a></li> <li><a href="/wiki/Longifolene" title="Longifolene">Longifolene</a></li> <li><a href="/wiki/Guaiene" title="Guaiene">β-Guaiene</a></li> <li><a href="/wiki/Valencene" title="Valencene">Valencene</a></li> <li><a href="/wiki/Bisabolene" title="Bisabolene">β-Bisabolene</a></li> <li><a href="/wiki/Cadinene" class="mw-redirect" title="Cadinene">γ-Cadinene</a></li> <li><a href="/wiki/Selinene" title="Selinene">β-Selinene</a></li> <li><a href="/w/index.php?title=Neophytadiene&action=edit&redlink=1" class="new" title="Neophytadiene (page does not exist)">Neophytadiene</a></li> <li><a href="/wiki/Ferruginol" title="Ferruginol">Ferruginol</a></li> <li><a href="/w/index.php?title=Aristolone&action=edit&redlink=1" class="new" title="Aristolone (page does not exist)">Aristolone</a></li> <li><a href="/wiki/Amyrin" title="Amyrin">β-Amyrin</a></li> <li><a href="/w/index.php?title=Oleanene&action=edit&redlink=1" class="new" title="Oleanene (page does not exist)">Oleanene</a></li> <li><a href="/w/index.php?title=Ketoursene&action=edit&redlink=1" class="new" title="Ketoursene (page does not exist)">Ketoursene</a></li> <li><a href="/wiki/Amyrin" title="Amyrin">α-Amyrin</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" /><style data-mw-deduplicate="TemplateStyles:r1038841319">.mw-parser-output .tooltip-dotted{border-bottom:1px dotted;cursor:help}</style><link rel="mw-deduplicated-inline-style" 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tooltip tooltip-dotted" title="Terpènes"><a rel="nofollow" class="external text" href="https://data.bnf.fr/ark:/12148/cb11979079r">BnF data</a></span></span></li><li><span class="uid"><a rel="nofollow" class="external text" href="https://id.ndl.go.jp/auth/ndlna/00572906">Japan</a></span></li><li><span class="uid"><span class="rt-commentedText tooltip tooltip-dotted" title="terpeny"><a rel="nofollow" class="external text" href="https://aleph.nkp.cz/F/?func=find-c&local_base=aut&ccl_term=ica=ph126610&CON_LNG=ENG">Czech Republic</a></span></span></li><li><span class="uid"><a rel="nofollow" class="external text" href="https://www.nli.org.il/en/authorities/987007529779805171">Israel</a></span></li></ul></div></td></tr></tbody></table></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?useformat=desktop&type=1x1&usesul3=0" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" 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