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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">Limonene</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 40 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-40" 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">40 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/%D9%84%D9%8A%D9%85%D9%88%D9%86%D9%8A%D9%86" title="ليمونين – Arabic" lang="ar" hreflang="ar" data-title="ليمونين" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D9%84%DB%8C%D9%88%D9%85%D9%88%D9%86%D9%86" title="لیومونن – South Azerbaijani" lang="azb" hreflang="azb" data-title="لیومونن" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-bn mw-list-item"><a href="https://bn.wikipedia.org/wiki/%E0%A6%B2%E0%A6%BF%E0%A6%AE%E0%A7%8B%E0%A6%A8%E0%A6%BF%E0%A6%A8" title="লিমোনিন – Bangla" lang="bn" hreflang="bn" data-title="লিমোনিন" data-language-autonym="বাংলা" data-language-local-name="Bangla" class="interlanguage-link-target"><span>বাংলা</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%9B%D0%B8%D0%BC%D0%BE%D0%BD%D0%B5%D0%BD" title="Лимонен – Bulgarian" lang="bg" hreflang="bg" data-title="Лимонен" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target"><span>Български</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Limon%C3%A8" title="Limonè – Catalan" lang="ca" hreflang="ca" data-title="Limonè" 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/Limonen" title="Limonen – Czech" lang="cs" hreflang="cs" data-title="Limonen" 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/Limonen" title="Limonen – Danish" lang="da" hreflang="da" data-title="Limonen" data-language-autonym="Dansk" data-language-local-name="Danish" class="interlanguage-link-target"><span>Dansk</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Limonen" title="Limonen – German" lang="de" hreflang="de" data-title="Limonen" 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/Limoneen" title="Limoneen – Estonian" lang="et" hreflang="et" data-title="Limoneen" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%9B%CE%B5%CE%BC%CE%BF%CE%BD%CE%AD%CE%BD%CE%B9%CE%BF" title="Λεμονένιο – Greek" lang="el" hreflang="el" data-title="Λεμονένιο" 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/Limoneno" title="Limoneno – Spanish" lang="es" hreflang="es" data-title="Limoneno" 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/Limoneno" title="Limoneno – Esperanto" lang="eo" hreflang="eo" data-title="Limoneno" 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/Limoneno" title="Limoneno – Basque" lang="eu" hreflang="eu" data-title="Limoneno" 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/%D9%84%DB%8C%D9%85%D9%88%D9%86%D9%86" title="لیمونن – Persian" lang="fa" hreflang="fa" data-title="لیمونن" 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/Limon%C3%A8ne" title="Limonène – French" lang="fr" hreflang="fr" data-title="Limonène" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EB%A6%AC%EB%AA%A8%EB%84%A8" title="리모넨 – Korean" lang="ko" hreflang="ko" data-title="리모넨" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Limonena" title="Limonena – Indonesian" lang="id" hreflang="id" data-title="Limonena" 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/Limonene" title="Limonene – Italian" lang="it" hreflang="it" data-title="Limonene" 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%9C%D7%99%D7%9E%D7%95%D7%A0%D7%9F" title="לימונן – Hebrew" lang="he" hreflang="he" data-title="לימונן" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Limon%C3%A9n" title="Limonén – Hungarian" lang="hu" hreflang="hu" data-title="Limonén" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%9B%D0%B8%D0%BC%D0%BE%D0%BD%D0%B5%D0%BD" title="Лимонен – Macedonian" lang="mk" hreflang="mk" data-title="Лимонен" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Limonena" title="Limonena – Malay" lang="ms" hreflang="ms" data-title="Limonena" 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/Limoneen" title="Limoneen – Dutch" lang="nl" hreflang="nl" data-title="Limoneen" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%AA%E3%83%A2%E3%83%8D%E3%83%B3" title="リモネン – Japanese" lang="ja" hreflang="ja" data-title="リモネン" 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/Limonen" title="Limonen – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Limonen" 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-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Limonen" title="Limonen – Polish" lang="pl" hreflang="pl" data-title="Limonen" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Limoneno" title="Limoneno – Portuguese" lang="pt" hreflang="pt" data-title="Limoneno" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Limonen" title="Limonen – Romanian" lang="ro" hreflang="ro" data-title="Limonen" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%9B%D0%B8%D0%BC%D0%BE%D0%BD%D0%B5%D0%BD" title="Лимонен – Russian" lang="ru" hreflang="ru" data-title="Лимонен" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Limonene" title="Limonene – Simple English" lang="en-simple" hreflang="en-simple" data-title="Limonene" data-language-autonym="Simple English" data-language-local-name="Simple English" class="interlanguage-link-target"><span>Simple English</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Limonen" title="Limonen – Slovenian" lang="sl" hreflang="sl" data-title="Limonen" 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/Limonen" title="Limonen – Serbian" lang="sr" hreflang="sr" data-title="Limonen" 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/Limonen" title="Limonen – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Limonen" 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 badge-Q17559452 badge-recommendedarticle mw-list-item" title="recommended article"><a href="https://fi.wikipedia.org/wiki/Limoneeni" title="Limoneeni – Finnish" lang="fi" hreflang="fi" data-title="Limoneeni" 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/Limonen" title="Limonen – Swedish" lang="sv" hreflang="sv" data-title="Limonen" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%B2%E0%AE%BF%E0%AE%AE%E0%AF%8B%E0%AE%A9%E0%AF%80%E0%AE%A9%E0%AF%8D" title="லிமோனீன் – Tamil" lang="ta" hreflang="ta" data-title="லிமோனீன்" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Limonen" title="Limonen – Turkish" lang="tr" hreflang="tr" data-title="Limonen" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%9B%D1%96%D0%BC%D0%BE%D0%BD%D0%B5%D0%BD" title="Лімонен – Ukrainian" lang="uk" hreflang="uk" data-title="Лімонен" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Limonen" title="Limonen – Vietnamese" lang="vi" hreflang="vi" data-title="Limonen" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target"><span>Tiếng Việt</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E6%9F%A0%E7%83%AF" title="柠烯 – Chinese" lang="zh" hreflang="zh" data-title="柠烯" 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 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data-unpinned-container-id="vector-appearance-unpinned-container" > <div class="vector-pinnable-header-label">Appearance</div> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-appearance.pin">move to sidebar</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-appearance.unpin">hide</button> </div> </div> </div> </nav> </div> </div> <div id="bodyContent" class="vector-body" aria-labelledby="firstHeading" data-mw-ve-target-container> <div class="vector-body-before-content"> <div class="mw-indicators"> </div> <div id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Liquid terpene hydrocarbon fragrance and flavor, extract of citrus peel</div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">Not to be confused with <a href="/wiki/Limonin" title="Limonin">Limonin</a>.</div> <p> <style data-mw-deduplicate="TemplateStyles:r1268415487">.mw-parser-output .ib-chembox{border-collapse:collapse;text-align:left}.mw-parser-output .ib-chembox td,.mw-parser-output .ib-chembox th{border:1px solid #a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}</style> </p> <table class="infobox ib-chembox"> <caption>Limonene </caption> <tbody><tr> <td colspan="2" class="borderless" style="text-align:center"> <table border="0" style="width:100%;display:inline-table;"> <tbody><tr> <td style="border-right:1px solid #aaa; width:50%;"><figure class="mw-halign-center skin-invert-image" typeof="mw:File"><a href="/wiki/File:(R)-Limonene.svg" class="mw-file-description" title="Skeletal structure of the (R)-isomer"><img alt="Skeletal structure of the (R)-isomer" src="//upload.wikimedia.org/wikipedia/commons/thumb/7/74/%28R%29-Limonene.svg/70px-%28R%29-Limonene.svg.png" decoding="async" width="70" height="170" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/74/%28R%29-Limonene.svg/105px-%28R%29-Limonene.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/74/%28R%29-Limonene.svg/140px-%28R%29-Limonene.svg.png 2x" data-file-width="78" data-file-height="189" /></a><figcaption>Skeletal structure of the (<i>R</i>)-isomer</figcaption></figure> </td> <td style="width:50%;"><figure class="mw-halign-center bg-transparent" typeof="mw:File"><a href="/wiki/File:Limonene-from-xtal-3D-bs.png" class="mw-file-description" title="Ball-and-stick model of the (R)-isomer"><img alt="Ball-and-stick model of the (R)-isomer" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/63/Limonene-from-xtal-3D-bs.png/100px-Limonene-from-xtal-3D-bs.png" decoding="async" width="100" height="191" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/63/Limonene-from-xtal-3D-bs.png/150px-Limonene-from-xtal-3D-bs.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/63/Limonene-from-xtal-3D-bs.png/200px-Limonene-from-xtal-3D-bs.png 2x" data-file-width="1045" data-file-height="2000" /></a><figcaption>Ball-and-stick model of the (<i>R</i>)-isomer</figcaption></figure> </td></tr></tbody></table> <div style="width:100%; text-align:center">Limonene (<i>R</i>)-isomer</div> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Limonene.jpg" class="mw-file-description" title="Limonene extracted from orange peels."><img alt="Limonene extracted from orange peels." src="//upload.wikimedia.org/wikipedia/commons/thumb/c/cb/Limonene.jpg/150px-Limonene.jpg" decoding="async" width="150" height="167" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/cb/Limonene.jpg/225px-Limonene.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/cb/Limonene.jpg/300px-Limonene.jpg 2x" data-file-width="2912" data-file-height="3248" /></a><figcaption>Limonene extracted from orange peels.</figcaption></figure><div style="text-align:center;">Limonene extracted from orange peel</div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Preferred_IUPAC_name" title="Preferred IUPAC name">Preferred IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;">1-Methyl-4-(prop-1-en-2-yl)cyclohex-1-ene</div></div> </td></tr> <tr> <td colspan="2" style="text-align:left;">Other names <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">1-Methyl-4-(1-methylethenyl)cyclohexene<br />4-Isopropenyl-1-methylcyclohexene<br /><i>p</i>-Menth-1,8-diene<br /><b>Racemic:</b> <span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">DL</span></span>-Limonene; Dipentene</div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=138-86-3">138-86-3</a></span> (<i>R</i>/<i>S</i>)<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=5989-27-5">5989-27-5</a></span> (<i>R</i>)<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=5989-54-8">5989-54-8</a></span> (<i>S</i>)<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=CC1%3DCCC%28CC1%29C%28%3DC%29C">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=15384">CHEBI:15384</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembl/explore/compound/ChEMBL449062">ChEMBL449062</a></span> (<i>R</i>)<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.20939.html">20939</a></span> (<i>R</i>/<i>S</i>)<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.388386.html">388386</a></span> (<i>S</i>)<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.389747.html">389747</a></span> (<i>R</i>)<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a> </td> <td><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.004.856">100.004.856</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q278809#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span> </td></tr> <tr> <td><a href="/wiki/KEGG" title="KEGG">KEGG</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.kegg.jp"><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/D00194">D00194</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/22311">22311</a></span> (<i>R</i>/<i>S</i>)</li><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/439250">439250</a></span> (<i>S</i>)</li></ul></div> </td></tr> <tr> <td><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/9MC3I34447">9MC3I34447</a></span> (<i>R</i>/<i>S</i>)<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/GFD7C86Q1W">GFD7C86Q1W</a></span> (<i>R</i>)<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/47MAJ1Y2NE">47MAJ1Y2NE</a></span> (<i>S</i>)<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID2029612">DTXSID2029612</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q278809#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></span></li></ul></div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,10H,1,5-7H2,2-3H3<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: XMGQYMWWDOXHJM-UHFFFAOYSA-N<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div></div></li></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">CC1=CCC(CC1)C(=C)C</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td><span title="Carbon">C</span><sub>10</sub><span title="Hydrogen">H</span><sub>16</sub> </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td><span class="nowrap"><span data-sort-value="7002136238000000000♠"></span>136.238</span> g·mol<sup>−1</sup>   </td></tr> <tr> <td>Appearance </td> <td>colorless liquid </td></tr> <tr> <td><a href="/wiki/Odor" title="Odor">Odor</a> </td> <td><a href="/wiki/Orange_(fruit)" title="Orange (fruit)">Orange</a> </td></tr> <tr> <td><a href="/wiki/Density" title="Density">Density</a> </td> <td>0.8411 g/cm<sup>3</sup> </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>−74.35 °C (−101.83 °F; 198.80 K) </td></tr> <tr> <td><a href="/wiki/Boiling_point" title="Boiling point">Boiling point</a> </td> <td>176 °C (349 °F; 449 K) </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Aqueous_solution" title="Aqueous solution">Solubility in water</a></div> </td> <td>Insoluble </td></tr> <tr> <td><a href="/wiki/Solubility" title="Solubility">Solubility</a> </td> <td><a href="/wiki/Miscible" class="mw-redirect" title="Miscible">Miscible</a> with <a href="/wiki/Benzene" title="Benzene">benzene</a>, <a href="/wiki/Chloroform" title="Chloroform">chloroform</a>, <a href="/wiki/Diethyl_ether" title="Diethyl ether">ether</a>, <a href="/wiki/Carbon_disulfide" title="Carbon disulfide">CS<sub>2</sub></a>, and oils <br /> soluble in <a href="/wiki/Carbon_tetrachloride" title="Carbon tetrachloride">CCl<sub>4</sub></a> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Specific_rotation" title="Specific rotation">Chiral rotation</a> ([α]<sub>D</sub>)</div> </td> <td>87–102° </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Refractive_index" title="Refractive index">Refractive index</a> (<i>n</i><sub>D</sub>)</div> </td> <td>1.4727 </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Thermochemistry </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Standard_enthalpy_change_of_combustion" class="mw-redirect" title="Standard enthalpy change of combustion">Std enthalpy of<br />combustion</a> <span style="font-size:112%;">(Δ<sub>c</sub><i>H</i><sup>⦵</sup><sub>298</sub>)</span></div> </td> <td>−6.128 MJ mol<sup>−1</sup> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Hazards </th></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;color:inherit;"><b><a href="/wiki/Occupational_safety_and_health" title="Occupational safety and health">Occupational safety and health</a></b> (OHS/OSH): </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Main hazards</div> </td> <td><a href="/wiki/Skin_sensitizer" class="mw-redirect" title="Skin sensitizer">Skin sensitizer</a> / <a href="/wiki/Contact_dermatitis" title="Contact dermatitis">Contact dermatitis</a> – After aspiration, <a href="/wiki/Pulmonary_oedema" class="mw-redirect" title="Pulmonary oedema">pulmonary oedema</a>, <a href="/wiki/Pneumonitis" title="Pneumonitis">pneumonitis</a>, and <a href="/wiki/Death" title="Death">death</a><sup id="cite_ref-pubchem_1-0" class="reference"><a href="#cite_note-pubchem-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;color:inherit;"><a href="/wiki/Globally_Harmonized_System_of_Classification_and_Labelling_of_Chemicals" title="Globally Harmonized System of Classification and Labelling of Chemicals"><b>GHS</b> labelling</a>: </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_hazard_pictograms" title="GHS hazard pictograms">Pictograms</a></div> </td> <td><span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-flamme.svg" class="mw-file-description" title="GHS02: Flammable"><img alt="GHS02: Flammable" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6d/GHS-pictogram-flamme.svg/50px-GHS-pictogram-flamme.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6d/GHS-pictogram-flamme.svg/75px-GHS-pictogram-flamme.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6d/GHS-pictogram-flamme.svg/100px-GHS-pictogram-flamme.svg.png 2x" data-file-width="512" data-file-height="512" /></a></span><span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-exclam.svg" class="mw-file-description" title="GHS07: Exclamation mark"><img alt="GHS07: Exclamation mark" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/50px-GHS-pictogram-exclam.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/75px-GHS-pictogram-exclam.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/100px-GHS-pictogram-exclam.svg.png 2x" data-file-width="512" data-file-height="512" /></a></span><span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-silhouette.svg" class="mw-file-description" title="GHS08: Health hazard"><img alt="GHS08: Health hazard" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/GHS-pictogram-silhouette.svg/50px-GHS-pictogram-silhouette.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/GHS-pictogram-silhouette.svg/75px-GHS-pictogram-silhouette.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/21/GHS-pictogram-silhouette.svg/100px-GHS-pictogram-silhouette.svg.png 2x" data-file-width="724" data-file-height="724" /></a></span><span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-pollu.svg" class="mw-file-description" title="GHS09: Environmental hazard"><img alt="GHS09: Environmental hazard" src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b9/GHS-pictogram-pollu.svg/50px-GHS-pictogram-pollu.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b9/GHS-pictogram-pollu.svg/75px-GHS-pictogram-pollu.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b9/GHS-pictogram-pollu.svg/100px-GHS-pictogram-pollu.svg.png 2x" data-file-width="724" data-file-height="724" /></a></span> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Globally_Harmonized_System_of_Classification_and_Labelling_of_Chemicals#Signal_word" title="Globally Harmonized System of Classification and Labelling of Chemicals">Signal word</a></div> </td> <td><b>Danger</b> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_hazard_statements" title="GHS hazard statements">Hazard statements</a></div> </td> <td><abbr class="abbr" title="H226: Flammable liquid and vapour">H226</abbr>, <abbr class="abbr" title="H304: May be fatal if swallowed and enters airways">H304</abbr>, <abbr class="abbr" title="H315: Causes skin irritation">H315</abbr>, <abbr class="abbr" title="H317: May cause an allergic skin reaction">H317</abbr>, <abbr class="abbr" title="H410: Very toxic to aquatic life with long lasting effects">H410</abbr> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_precautionary_statements" title="GHS precautionary statements">Precautionary statements</a></div> </td> <td><abbr class="abbr" title="P210: Keep away from heat, hot surfaces, sparks, open flames and other ignition sources. No smoking.">P210</abbr>, <abbr class="abbr" title="P233: Keep container tightly closed.">P233</abbr>, <abbr class="abbr" title="P235: Keep cool.">P235</abbr>, <abbr class="abbr" title="P240: Ground and bond container and receiving equipment.">P240</abbr>, <abbr class="abbr" title="P241: Use explosion-proof electrical/ventilating/light/.../equipment.">P241</abbr>, <abbr class="abbr" title="P242: Use only non-sparking tools.">P242</abbr>, <abbr class="abbr" title="P243: Take precautionary measures to prevent static discharges.">P243</abbr>, <abbr class="abbr" title="P261: Avoid breathing dust/fume/gas/mist/vapours/spray.">P261</abbr>, <abbr class="abbr" title="P264: Wash ... thoroughly after handling.">P264</abbr>, <abbr class="abbr" title="P272: Contaminated work clothing should not be allowed out of the workplace.">P272</abbr>, <abbr class="abbr" title="P273: Avoid release to the environment.">P273</abbr>, <abbr class="abbr" title="P280: Wear protective gloves/protective clothing/eye protection/face protection.">P280</abbr>, <abbr class="abbr" title="P301+P330+P331: IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.">P301+P330+P331</abbr>, <abbr class="abbr" title="P302+P352: IF ON SKIN: Wash with soap and water.">P302+P352</abbr>, <abbr class="abbr" title="P303+P361+P353: IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water [or shower].">P303+P361+P353</abbr>, <abbr class="abbr" title="P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing.">P304+P340</abbr>, <abbr class="abbr" title="P312: Call a POISON CENTER or doctor/physician if you feel unwell.">P312</abbr>, <abbr class="abbr" title="P333+P313: If skin irritation or a rash occurs: Get medical advice/attention.">P333+P313</abbr>, <abbr class="abbr" title="P362: Take off contaminated clothing.">P362</abbr>, <abbr class="abbr" title="P370+P378: In case of fire: Use ... to extinguish.">P370+P378</abbr>, <abbr class="abbr" title="P391: Collect spillage.">P391</abbr>, <abbr class="abbr" title="P403+P233: Store in a well ventilated place. Keep container tightly closed.">P403+P233</abbr>, <abbr class="abbr" title="P405: Store locked up.">P405</abbr>, <abbr class="abbr" title="P501: Dispose of contents/container to ...">P501</abbr> </td></tr> <tr> <td><a href="/wiki/NFPA_704" title="NFPA 704"><b>NFPA 704</b></a> (fire diamond) </td> <td><style data-mw-deduplicate="TemplateStyles:r1170367383">.mw-parser-output .nfpa-704-diamond-ref{float:right;padding:1px;text-align:right}.mw-parser-output .nfpa-704-diamond-container{width:82px;font-family:sans-serif;margin:0 auto}.mw-parser-output .nfpa-704-diamond-container-ref{float:left;margin-left:1em}.mw-parser-output .nfpa-704-diamond-images{float:left;font-size:20px;text-align:center;position:relative;height:80px;width:80px;padding:1px}.mw-parser-output .nfpa-704-diamond-map{position:absolute;height:80px;width:80px}.mw-parser-output .nfpa-704-diamond .noresize{margin:0 auto}.mw-parser-output .nfpa-704-diamond-code{line-height:1em;text-align:center;position:absolute}.mw-parser-output .nfpa-704-diamond-code>a{color:black}.mw-parser-output .nfpa-704-diamond-blue{width:13px;top:31px;left:15px}.mw-parser-output .nfpa-704-diamond-red{width:12px;top:12px;left:35px}.mw-parser-output .nfpa-704-diamond-yellow{width:13px;top:31px;left:54px}.mw-parser-output .nfpa-704-diamond-white-image{position:relative;top:51px;left:0}.mw-parser-output .nfpa-704-diamond-white-text{vertical-align:middle;text-align:center;line-height:80%;position:absolute;top:52px}.mw-parser-output .nfpa-704-diamond-white-text a>span{position:absolute;color:black}.mw-parser-output .nfpa-704-diamond-white-wors{font-size:15px;width:23px;left:29px}.mw-parser-output .nfpa-704-diamond-white-wox{font-size:15px;font-stretch:condensed;width:21px;line-height:80%;top:-4px;left:29px}.mw-parser-output .nfpa-704-diamond-white-abcp{font-size:13.5px;font-stretch:condensed;width:28px;left:26px}.mw-parser-output .nfpa-704-diamond-white-ac{font-size:10px;width:30px;left:25px}.mw-parser-output .nfpa-704-diamond-white-strike{text-decoration:line-through}</style><div class="nfpa-704-diamond notheme"><div class="nfpa-704-diamond-container"><div class="nfpa-704-diamond-images nounderlines"> <div class="nfpa-704-diamond-map"><figure class="noresize" typeof="mw:File"><span><img alt="NFPA 704 four-colored diamond" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/80px-NFPA_704.svg.png" decoding="async" width="80" height="80" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/120px-NFPA_704.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/160px-NFPA_704.svg.png 2x" data-file-width="512" data-file-height="512" usemap="#ImageMap_f39ae6e266e5d33a" /></span><map name="ImageMap_f39ae6e266e5d33a"><area href="/wiki/NFPA_704#Blue" shape="poly" coords="23,23,47,47,23,70,0,47" alt="Health 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroform" title="Health 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroform" /><area href="/wiki/NFPA_704#Red" shape="poly" coords="47,0,70,23,47,47,23,23" alt="Flammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuel" title="Flammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuel" /><area href="/wiki/NFPA_704#Yellow" shape="poly" coords="70,23,94,47,70,70,47,47" alt="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" title="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" /><area href="/wiki/NFPA_704#White" shape="poly" coords="47,47,70,70,47,94,23,70" alt="Special hazards (white): no code" title="Special hazards (white): no code" /></map><figcaption></figcaption></figure></div><div class="nfpa-704-diamond-code nfpa-704-diamond-blue"> <a href="/wiki/NFPA_704#Blue" title="NFPA 704"><span title="Health 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroform" class="notheme mw-no-invert">2</span></a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-red"> <a href="/wiki/NFPA_704#Red" title="NFPA 704"><span title="Flammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuel" class="notheme mw-no-invert">2</span></a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-yellow"> <a href="/wiki/NFPA_704#Yellow" title="NFPA 704"><span title="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" class="notheme mw-no-invert">0</span></a></div></div></div></div> </td></tr> <tr> <td><a href="/wiki/Flash_point" title="Flash point">Flash point</a> </td> <td>50 °C (122 °F; 323 K) </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Autoignition_temperature" title="Autoignition temperature">Autoignition<br />temperature</a></div> </td> <td>237 °C (459 °F; 510 K) </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; color:inherit; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"></div> <div style="margin-top: 0.3em; text-align: center;"><a href="/wiki/Wikipedia:Chemical_infobox#References" title="Wikipedia:Chemical infobox">Infobox references</a></div> </td></tr> </tbody></table><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound</div> <p><b>Limonene</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="'l' in 'lie'">l</span><span title="/ɪ/: 'i' in 'kit'">ɪ</span><span title="'m' in 'my'">m</span><span title="/ə/: 'a' in 'about'">ə</span><span title="'n' in 'nigh'">n</span><span title="/ˌ/: secondary stress follows">ˌ</span><span title="/iː/: 'ee' in 'fleece'">iː</span><span title="'n' in 'nigh'">n</span></span>/</a></span></span>) is a colorless liquid <a href="/wiki/Aliphatic" class="mw-redirect" title="Aliphatic">aliphatic</a> <a href="/wiki/Hydrocarbon" title="Hydrocarbon">hydrocarbon</a> classified as a cyclic <a href="/wiki/Monoterpene" title="Monoterpene">monoterpene</a>, and is the major component in the <a href="/wiki/Essential_oil" title="Essential oil">essential oil</a> of <a href="/wiki/Citrus_fruit" class="mw-redirect" title="Citrus fruit">citrus fruit</a> <a href="/wiki/Peel_(fruit)" title="Peel (fruit)">peels</a>.<sup id="cite_ref-pubchem_1-1" class="reference"><a href="#cite_note-pubchem-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> The (+)-<a href="/wiki/Isomer" title="Isomer">isomer</a>, occurring more commonly in nature as the fragrance of oranges, is a flavoring agent in food manufacturing.<sup id="cite_ref-pubchem_1-2" class="reference"><a href="#cite_note-pubchem-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Ullmann_2-0" class="reference"><a href="#cite_note-Ullmann-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> It is also used in chemical synthesis as a <a href="/wiki/Precursor_(chemistry)" title="Precursor (chemistry)">precursor</a> to <a href="/wiki/Carvone" title="Carvone">carvone</a> and as a renewables-based <a href="/wiki/Solvent" title="Solvent">solvent</a> in <a href="/wiki/Cleaning_product" class="mw-redirect" title="Cleaning product">cleaning products</a>.<sup id="cite_ref-pubchem_1-3" class="reference"><a href="#cite_note-pubchem-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> The less common (-)-<a href="/wiki/Isomer" title="Isomer">isomer</a> has a <a href="/wiki/Pine" title="Pine">piny</a>, <a href="/wiki/Turpentine" title="Turpentine">turpentine</a>-like odor, and is found in the edible parts of such plants as <a href="/wiki/Caraway" title="Caraway">caraway</a>, <a href="/wiki/Dill" title="Dill">dill</a>, and <a href="/wiki/Bergamot_orange" title="Bergamot orange">bergamot orange</a> plants.<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> </p><p>Limonene takes its name from <a href="/wiki/Italian_language" title="Italian language">Italian</a> <i>limone</i> ("<a href="/wiki/Lemon" title="Lemon">lemon</a>").<sup id="cite_ref-merweb_4-0" class="reference"><a href="#cite_note-merweb-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> Limonene is a <a href="/wiki/Chirality_(chemistry)" title="Chirality (chemistry)">chiral</a> molecule, and biological sources produce one <a href="/wiki/Enantiomer" title="Enantiomer">enantiomer</a>: the principal industrial source, <a href="/wiki/Citrus_fruit" class="mw-redirect" title="Citrus fruit">citrus fruit</a>, contains (+)-limonene (<i>d</i>-limonene), which is the <a href="/wiki/Cahn%E2%80%93Ingold%E2%80%93Prelog_priority_rules" title="Cahn–Ingold–Prelog priority rules">(<i>R</i>)</a>-enantiomer.<sup id="cite_ref-pubchem_1-4" class="reference"><a href="#cite_note-pubchem-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> (+)-Limonene is obtained commercially from citrus fruits through two primary methods: <a href="/wiki/Centrifugal_separation" class="mw-redirect" title="Centrifugal separation">centrifugal separation</a> or <a href="/wiki/Steam_distillation" title="Steam distillation">steam distillation</a>. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="In_plants">In plants</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Limonene&action=edit&section=1" title="Edit section: In plants"><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:NIH_citrus.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/9d/NIH_citrus.jpg/220px-NIH_citrus.jpg" decoding="async" width="220" height="180" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/9d/NIH_citrus.jpg/330px-NIH_citrus.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/9/9d/NIH_citrus.jpg 2x" data-file-width="332" data-file-height="271" /></a><figcaption>Limonene contributes to the characteristic odor of <a href="/wiki/Orange_oil" title="Orange oil">orange peel</a>, <a href="/wiki/Orange_juice" title="Orange juice">orange juice</a> and other <a href="/wiki/Citrus" title="Citrus">citrus</a> fruits.</figcaption></figure> <p>(+)-Limonene is a major component of the aromatic scents and <a href="/wiki/Resins" class="mw-redirect" title="Resins">resins</a> characteristic of numerous coniferous and broadleaved trees: red and silver maple (<i><a href="/wiki/Acer_rubrum" title="Acer rubrum">Acer rubrum</a></i>, <i><a href="/wiki/Acer_saccharinum" title="Acer saccharinum">Acer saccharinum</a></i>), cottonwoods (<i><a href="/wiki/Populus_angustifolia" title="Populus angustifolia">Populus angustifolia</a></i>), aspens (<i><a href="/wiki/Populus_grandidentata" title="Populus grandidentata">Populus grandidentata</a></i>, <i><a href="/wiki/Populus_tremuloides" title="Populus tremuloides">Populus tremuloides</a></i>) sumac (<i><a href="/wiki/Rhus_glabra" title="Rhus glabra">Rhus glabra</a></i>), spruce (<i><a href="/wiki/Picea" class="mw-redirect" title="Picea">Picea</a></i> spp.), various pines (e.g., <i><a href="/wiki/Pinus_echinata" title="Pinus echinata">Pinus echinata</a></i>, <i><a href="/wiki/Pinus_ponderosa" title="Pinus ponderosa">Pinus ponderosa</a></i>), <i><a href="/wiki/Pinus_leucodermis" class="mw-redirect" title="Pinus leucodermis">Pinus leucodermis</a></i>,<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> Douglas fir (<i><a href="/wiki/Pseudotsuga_menziesii" class="mw-redirect" title="Pseudotsuga menziesii">Pseudotsuga menziesii</a></i>), larches (<i><a href="/wiki/Larix" class="mw-redirect" title="Larix">Larix</a></i> spp.), true firs (<i><a href="/wiki/Abies" class="mw-redirect" title="Abies">Abies</a></i> spp.), hemlocks (<i><a href="/wiki/Tsuga" title="Tsuga">Tsuga</a></i> spp.), cannabis (<i><a href="/wiki/Cannabis_sativa" title="Cannabis sativa">Cannabis sativa</a></i> spp.),<sup id="cite_ref-Booth_6-0" class="reference"><a href="#cite_note-Booth-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> cedars (<i><a href="/wiki/Cedrus" title="Cedrus">Cedrus</a></i> spp.), various <a href="/wiki/Cupressaceae" title="Cupressaceae">Cupressaceae</a>, and juniper bush (<i><a href="/wiki/Juniperus" class="mw-redirect" title="Juniperus">Juniperus</a></i> spp.).<sup id="cite_ref-pubchem_1-5" class="reference"><a href="#cite_note-pubchem-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup class="noprint Inline-Template" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Verifiability" title="Wikipedia:Verifiability"><span title="The reference lists hundreds of species (under Taxonomy) but it doesn't make it clear that it's talking about D-limonene specifically. (June 2023)">failed verification</span></a></i>]</sup> It contributes to the characteristic odor of <a href="/wiki/Orange_oil" title="Orange oil">orange peel</a>, <a href="/wiki/Orange_juice" title="Orange juice">orange juice</a> and other <a href="/wiki/Citrus" title="Citrus">citrus</a> fruits.<sup id="cite_ref-pubchem_1-6" class="reference"><a href="#cite_note-pubchem-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Perez_7-0" class="reference"><a href="#cite_note-Perez-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> To optimize recovery of valued components from citrus peel waste, (+)-limonene is typically removed.<sup id="cite_ref-Sharma_8-0" class="reference"><a href="#cite_note-Sharma-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Chemical_reactions">Chemical reactions</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Limonene&action=edit&section=2" title="Edit section: Chemical reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Limonene is a relatively stable <a href="/wiki/Monoterpene" title="Monoterpene">monoterpene</a> and can be distilled without decomposition, although at elevated temperatures it <a href="/wiki/Cracking_(chemistry)" title="Cracking (chemistry)">cracks</a> to form <a href="/wiki/Isoprene" title="Isoprene">isoprene</a>.<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> It oxidizes easily in moist air to produce <a href="/wiki/Carveol" title="Carveol">carveol</a>, <a href="/wiki/Carvone" title="Carvone">carvone</a>, and limonene oxide.<sup id="cite_ref-pubchem_1-7" class="reference"><a href="#cite_note-pubchem-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> With sulfur, it undergoes dehydrogenation to <a href="/wiki/P-Cymene" title="P-Cymene"><i>p</i>-cymene</a>.<sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p><p>Limonene occurs commonly as the (<i>R</i>)-enantiomer, but <a href="/wiki/Racemization" title="Racemization">racemizes</a> at 300 °C. When warmed with <a href="/wiki/Mineral_acid" title="Mineral acid">mineral acid</a>, limonene isomerizes to the <a href="/wiki/Conjugated_system" title="Conjugated system">conjugated diene</a> α-<a href="/wiki/Terpinene" title="Terpinene">terpinene</a> (which can also easily be converted to <a href="/wiki/P-Cymene" title="P-Cymene"><i>p</i>-cymene</a>). Evidence for this isomerization includes the formation of <a href="/wiki/Diels%E2%80%93Alder_reaction" title="Diels–Alder reaction">Diels–Alder</a> <a href="/wiki/Adduct" title="Adduct">adducts</a> between α-terpinene adducts and <a href="/wiki/Maleic_anhydride" title="Maleic anhydride">maleic anhydride</a>. </p><p>It is possible to effect reaction at one of the double bonds selectively. Anhydrous <a href="/wiki/Hydrogen_chloride" title="Hydrogen chloride">hydrogen chloride</a> reacts preferentially at the disubstituted alkene, whereas <a href="/wiki/Epoxidation" class="mw-redirect" title="Epoxidation">epoxidation</a> with <a href="/wiki/Meta-Chloroperoxybenzoic_acid" title="Meta-Chloroperoxybenzoic acid"><i>m</i>CPBA</a> occurs at the trisubstituted alkene. </p><p>In another synthetic method <a href="/wiki/Markovnikov%27s_rule" title="Markovnikov's rule">Markovnikov addition</a> of <a href="/wiki/Trifluoroacetic_acid" title="Trifluoroacetic acid">trifluoroacetic acid</a> followed by <a href="/wiki/Hydrolysis" title="Hydrolysis">hydrolysis</a> of the acetate gives <a href="/wiki/Terpineol" title="Terpineol">terpineol</a>. </p><p>The most widely practiced conversion of limonene is to <a href="/wiki/Carvone" title="Carvone">carvone</a>. The three-step reaction begins with the <a href="/wiki/Regioselective" class="mw-redirect" title="Regioselective">regioselective</a> addition of <a href="/wiki/Nitrosyl_chloride" title="Nitrosyl chloride">nitrosyl chloride</a> across the trisubstituted double bond. This species is then converted to the <a href="/wiki/Oxime" title="Oxime">oxime</a> with a <a href="/wiki/Base_(chemistry)" title="Base (chemistry)">base</a>, and the <a href="/wiki/Hydroxylamine" title="Hydroxylamine">hydroxylamine</a> is removed to give the <a href="/wiki/Ketone" title="Ketone">ketone</a>-containing carvone.<sup id="cite_ref-Ullmann_2-1" class="reference"><a href="#cite_note-Ullmann-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Biosynthesis">Biosynthesis</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Limonene&action=edit&section=3" title="Edit section: Biosynthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In nature, limonene is formed from <a href="/wiki/Geranyl_pyrophosphate" title="Geranyl pyrophosphate">geranyl pyrophosphate</a>, via cyclization of a <a href="/wiki/Nerol" title="Nerol">neryl</a> <a href="/wiki/Carbocation" title="Carbocation">carbocation</a> or its equivalent as shown.<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> The final step involves loss of a proton from the cation to form the <a href="/wiki/Alkene" title="Alkene">alkene</a>. </p><p><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:Limonene_Biosynthesis_(coloured).svg" class="mw-file-description" title="Biosynthesis of limonene from geranyl pyrophosphate"><img alt="Biosynthesis of limonene from geranyl pyrophosphate" src="//upload.wikimedia.org/wikipedia/commons/thumb/7/7e/Limonene_Biosynthesis_%28coloured%29.svg/500px-Limonene_Biosynthesis_%28coloured%29.svg.png" decoding="async" width="500" height="106" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/7e/Limonene_Biosynthesis_%28coloured%29.svg/750px-Limonene_Biosynthesis_%28coloured%29.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/7e/Limonene_Biosynthesis_%28coloured%29.svg/1000px-Limonene_Biosynthesis_%28coloured%29.svg.png 2x" data-file-width="1153" data-file-height="245" /></a></span> </p> <div class="mw-heading mw-heading2"><h2 id="Uses">Uses</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Limonene&action=edit&section=4" title="Edit section: Uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>As the main fragrance of citrus peels, <span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">D</span></span>-limonene is used in food manufacturing and some medicines, such as a <a href="/wiki/Flavoring_agent" class="mw-redirect" title="Flavoring agent">flavoring agent</a> to mask the bitter taste of <a href="/wiki/Alkaloids" class="mw-redirect" title="Alkaloids">alkaloids</a>, and as a fragrance in <a href="/wiki/Perfumery" class="mw-redirect" title="Perfumery">perfumery</a>, aftershave lotions, bath products, and other <a href="/wiki/Personal_care" class="mw-redirect" title="Personal care">personal care</a> products.<sup id="cite_ref-pubchem_1-8" class="reference"><a href="#cite_note-pubchem-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> (+)-Limonene is also used as a <a href="/wiki/Botanical" class="mw-redirect" title="Botanical">botanical</a> <a href="/wiki/Insecticide" title="Insecticide">insecticide</a>.<sup id="cite_ref-pubchem_1-9" class="reference"><a href="#cite_note-pubchem-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><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> (+)-Limonene is used in the organic herbicides.<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> It is added to cleaning products, such as hand cleansers, to give a lemon or orange fragrance (see <a href="/wiki/Orange_oil" title="Orange oil">orange oil</a>) and for its ability to dissolve oils.<sup id="cite_ref-pubchem_1-10" class="reference"><a href="#cite_note-pubchem-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> In contrast, (-)-limonene has a <a href="/wiki/Pine" title="Pine">piny</a>, <a href="/wiki/Turpentine" title="Turpentine">turpentine</a>-like odor. </p><p>Limonene is used as a <a href="/wiki/Solvent" title="Solvent">solvent</a> for cleaning purposes, such as <a href="/wiki/Adhesive_remover" title="Adhesive remover">adhesive remover</a>, or the removal of oil from machine parts, as it is produced from a renewable source (citrus essential oil, as a byproduct of <a href="/wiki/Orange_juice" title="Orange juice">orange juice</a> manufacture).<sup id="cite_ref-Sharma_8-1" class="reference"><a href="#cite_note-Sharma-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> It is used as a <a href="/wiki/Paint_stripper" title="Paint stripper">paint stripper</a> and is also useful as a fragrant alternative to turpentine. Limonene is also used as a solvent in some <a href="/wiki/Model_airplane" class="mw-redirect" title="Model airplane">model airplane</a> glues and as a constituent in some paints. Commercial air fresheners, with air propellants, containing limonene are used by <a href="/wiki/Philately" title="Philately">stamp collectors</a> to remove self-adhesive postage stamps from envelope paper.<sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> </p><p>Limonene is also used as a solvent for fused filament fabrication based <a href="/wiki/3D_printing" title="3D printing">3D printing</a>.<sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> Printers can print the plastic of choice for the model, but erect supports and binders from <a href="/wiki/High_impact_polystyrene" class="mw-redirect" title="High impact polystyrene">high impact polystyrene</a> (HIPS), a <a href="/wiki/Polystyrene" title="Polystyrene">polystyrene</a> plastic that is easily soluble in limonene. </p><p>In preparing <a href="/wiki/Tissue_(biology)" title="Tissue (biology)">tissues</a> for <a href="/wiki/Histology" title="Histology">histology</a> or histopathology, <span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">D</span></span>-limonene is often used as a less toxic substitute for <a href="/wiki/Xylene" title="Xylene">xylene</a> when clearing dehydrated specimens. Clearing agents are liquids miscible with alcohols (such as <a href="/wiki/Ethanol" title="Ethanol">ethanol</a> or <a href="/wiki/Isopropanol" class="mw-redirect" title="Isopropanol">isopropanol</a>) and with melted <a href="/wiki/Paraffin_wax" title="Paraffin wax">paraffin wax</a>, in which specimens are embedded to facilitate cutting of thin sections for <a href="/wiki/Microscopy" title="Microscopy">microscopy</a>.<sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup><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><sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> </p><p>Limonene, from orange peel oil, is also combustible and has been considered as a <a href="/wiki/Biofuel" title="Biofuel">biofuel</a>.<sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Safety_and_research">Safety and research</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Limonene&action=edit&section=5" title="Edit section: Safety and research"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Applied to skin, limonene may cause irritation from <a href="/wiki/Contact_dermatitis" title="Contact dermatitis">contact dermatitis</a>, but otherwise appears to be safe for human use.<sup id="cite_ref-21" class="reference"><a href="#cite_note-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-22" class="reference"><a href="#cite_note-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> Limonene is <a href="/wiki/Flammable" class="mw-redirect" title="Flammable">flammable</a> as a liquid or vapor and it is toxic to <a href="/wiki/Aquatic_life" class="mw-redirect" title="Aquatic life">aquatic life</a>.<sup id="cite_ref-pubchem_1-11" class="reference"><a href="#cite_note-pubchem-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Cancer">Cancer</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Limonene&action=edit&section=6" title="Edit section: Cancer"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>There is no evidence that the limonene in peel oils of citrus fruits affects the onset or progress of cancer, with one national agency stating, "There is no consistent evidence that people with cancer who consume limonene—either in supplement form or by eating citrus fruits—get better or are more likely to be cured".<sup id="cite_ref-NASEM_23-0" class="reference"><a href="#cite_note-NASEM-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Limonene&action=edit&section=7" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Essential_oil" title="Essential oil">Essential oil</a></li> <li><a href="/wiki/Monoterpenes" class="mw-redirect" title="Monoterpenes">Monoterpenes</a></li> <li><a href="/wiki/Resin" title="Resin">Resin</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Limonene&action=edit&section=8" 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-pubchem-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-pubchem_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-pubchem_1-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-pubchem_1-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-pubchem_1-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-pubchem_1-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-pubchem_1-5"><sup><i><b>f</b></i></sup></a> <a href="#cite_ref-pubchem_1-6"><sup><i><b>g</b></i></sup></a> <a href="#cite_ref-pubchem_1-7"><sup><i><b>h</b></i></sup></a> <a href="#cite_ref-pubchem_1-8"><sup><i><b>i</b></i></sup></a> <a href="#cite_ref-pubchem_1-9"><sup><i><b>j</b></i></sup></a> <a href="#cite_ref-pubchem_1-10"><sup><i><b>k</b></i></sup></a> <a href="#cite_ref-pubchem_1-11"><sup><i><b>l</b></i></sup></a></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/22311">"<span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">D</span></span>-Limonene"</a>. PubChem, US National Library of Medicine. 11 May 2024<span class="reference-accessdate">. Retrieved <span class="nowrap">18 May</span> 2024</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=%3Cspan+class%3D%22smallcaps%22%3E%3Cspan+style%3D%22font-variant%3A+small-caps%3B+text-transform%3A+lowercase%3B%22%3ED%3C%2Fspan%3E%3C%2Fspan%3E-Limonene&rft.pub=PubChem%2C+US+National+Library+of+Medicine&rft.date=2024-05-11&rft_id=https%3A%2F%2Fpubchem.ncbi.nlm.nih.gov%2Fcompound%2F22311&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALimonene" class="Z3988"></span></span> </li> <li id="cite_note-Ullmann-2"><span class="mw-cite-backlink">^ <a href="#cite_ref-Ullmann_2-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Ullmann_2-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFahlbuschHammerschmidtPantenPickenhagen2003" class="citation book cs1">Fahlbusch, Karl-Georg; Hammerschmidt, Franz-Josef; Panten, Johannes; et al. 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"Flavors and Fragrances". <i>Ullmann's Encyclopedia of Industrial Chemistry</i>. <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.a11_141">10.1002/14356007.a11_141</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=Flavors+and+Fragrances&rft.btitle=Ullmann%27s+Encyclopedia+of+Industrial+Chemistry&rft.date=2003&rft_id=info%3Adoi%2F10.1002%2F14356007.a11_141&rft.isbn=978-3-527-30673-2&rft.aulast=Fahlbusch&rft.aufirst=Karl-Georg&rft.au=Hammerschmidt%2C+Franz-Josef&rft.au=Panten%2C+Johannes&rft.au=Pickenhagen%2C+Wilhelm&rft.au=Schatkowski%2C+Dietmar&rft.au=Bauer%2C+Kurt&rft.au=Garbe%2C+Dorothea&rft.au=Surburg%2C+Horst&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALimonene" class="Z3988"></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://www.acs.org/content/acs/en/molecule-of-the-week/archive/l/limonene.html">"Molecule of the Week Archive: Limonene"</a>. <a href="/wiki/American_Chemical_Society" title="American Chemical Society">American Chemical Society</a>. 1 November 2021<span class="reference-accessdate">. Retrieved <span class="nowrap">5 November</span> 2021</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Molecule+of+the+Week+Archive%3A+Limonene&rft.pub=American+Chemical+Society&rft.date=2021-11-01&rft_id=https%3A%2F%2Fwww.acs.org%2Fcontent%2Facs%2Fen%2Fmolecule-of-the-week%2Farchive%2Fl%2Flimonene.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALimonene" class="Z3988"></span></span> </li> <li id="cite_note-merweb-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-merweb_4-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation encyclopaedia cs1"><a rel="nofollow" class="external text" href="https://www.merriam-webster.com/dictionary/limonene">"limonene"</a>. <i>merriam-webster.com</i>. Merriam-Webster. 22 September 2023<span class="reference-accessdate">. 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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"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"> <div class="side-box-flex"> <div class="side-box-image"><span class="noviewer" typeof="mw:File"><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/30px-Commons-logo.svg.png" decoding="async" width="30" height="40" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/45px-Commons-logo.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/59px-Commons-logo.svg.png 2x" data-file-width="1024" data-file-height="1376" /></a></span></div> <div class="side-box-text plainlist">Wikimedia Commons has media related to <span style="font-weight: bold; font-style: italic;"><a href="https://commons.wikimedia.org/wiki/Category:Limonene" class="extiw" title="commons:Category:Limonene">Limonene</a></span>.</div></div> </div> <ul><li><a rel="nofollow" class="external text" href="http://gmd.mpimp-golm.mpg.de/Spectrums/69d65d67-cef8-4af7-8d38-43a63ba43249.aspx">Mass spectrum of limonene</a></li> <li><a rel="nofollow" class="external text" href="https://www.cdc.gov/niosh/ipcsneng/neng0918.html">Description of <span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">D</span></span>-limonene on the International Chemical Safety Cards</a></li> <li><a rel="nofollow" class="external text" href="https://www3.epa.gov/pesticides/chem_search/reg_actions/reregistration/fs_PC-079701_1-Sep-94.pdf"><span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">D</span></span>-Limonene information</a> from the United States <a href="/wiki/Environmental_Protection_Agency" class="mw-redirect" title="Environmental Protection Agency">Environmental Protection Agency</a></li></ul> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output .hlist.inline,.mw-parser-output .hlist.inline dl,.mw-parser-output .hlist.inline ol,.mw-parser-output .hlist.inline ul,.mw-parser-output .hlist dl dl,.mw-parser-output .hlist dl ol,.mw-parser-output .hlist dl ul,.mw-parser-output .hlist ol dl,.mw-parser-output .hlist ol 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.navbox{display:none!important}}</style></div><div role="navigation" class="navbox" aria-labelledby="Citrus803" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><style data-mw-deduplicate="TemplateStyles:r1239400231">.mw-parser-output .navbar{display:inline;font-size:88%;font-weight:normal}.mw-parser-output .navbar-collapse{float:left;text-align:left}.mw-parser-output .navbar-boxtext{word-spacing:0}.mw-parser-output .navbar ul{display:inline-block;white-space:nowrap;line-height:inherit}.mw-parser-output .navbar-brackets::before{margin-right:-0.125em;content:"[ "}.mw-parser-output .navbar-brackets::after{margin-left:-0.125em;content:" ]"}.mw-parser-output .navbar li{word-spacing:-0.125em}.mw-parser-output .navbar a>span,.mw-parser-output .navbar a>abbr{text-decoration:inherit}.mw-parser-output .navbar-mini abbr{font-variant:small-caps;border-bottom:none;text-decoration:none;cursor:inherit}.mw-parser-output .navbar-ct-full{font-size:114%;margin:0 7em}.mw-parser-output .navbar-ct-mini{font-size:114%;margin:0 4em}html.skin-theme-clientpref-night .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}@media(prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}}@media print{.mw-parser-output .navbar{display:none!important}}</style><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Citrus" title="Template:Citrus"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Citrus" title="Template talk:Citrus"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Citrus" title="Special:EditPage/Template:Citrus"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Citrus803" style="font-size:114%;margin:0 4em"><a href="/wiki/Citrus" title="Citrus">Citrus</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">True <a href="/wiki/Species" title="Species">species</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/Australian_lime" title="Australian lime">Australian and Papuan wild limes group</a></li> <li><a href="/wiki/Citron" title="Citron">Citron</a></li> <li><a href="/wiki/Citrus_cavaleriei" title="Citrus cavaleriei">Ichang papeda</a></li> <li><a href="/wiki/Kaffir_lime" title="Kaffir lime">Kaffir lime</a></li> <li><a href="/wiki/Kumquat" title="Kumquat">Kumquats group</a></li> <li><a href="/wiki/Mandarin_orange" title="Mandarin orange">Mandarin orange</a></li> <li><a href="/wiki/Citrus_mangshanensis" title="Citrus mangshanensis">Mangshanyegan</a></li> <li><a href="/wiki/Citrus_halimii" title="Citrus halimii">Mountain citron</a></li> <li><a href="/wiki/Pomelo" title="Pomelo">Pomelo</a></li> <li><a href="/wiki/Citrus_ryukyuensis" title="Citrus ryukyuensis">Ryukyu mandarin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Major <a href="/wiki/Citrus_hybrid" class="mw-redirect" title="Citrus hybrid">hybrids</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/Grapefruit" title="Grapefruit">Grapefruit</a></li> <li><a href="/wiki/Lemon" title="Lemon">Lemon</a></li> <li><a href="/wiki/Lime_(fruit)" title="Lime (fruit)">Lime</a></li> <li><a href="/wiki/Orange_(fruit)" title="Orange (fruit)">Orange</a> <small>(<a href="/wiki/Citrus_%C3%97_sinensis" title="Citrus × sinensis">sweet orange</a>)</small></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">True and hybrid<br /><a href="/wiki/Cultivar" title="Cultivar">cultivars</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/Citrus_macrophylla" title="Citrus macrophylla">Alemow</a></li> <li><a href="/wiki/Amanatsu" title="Amanatsu">Amanatsu</a></li> <li><a href="/wiki/Assam_lemon" title="Assam lemon">Assam lemon</a></li> <li><a href="/wiki/Bergamot_orange" title="Bergamot orange">Bergamot orange</a></li> <li><a href="/wiki/Bizzarria" title="Bizzarria">Bizzarria</a></li> <li><a href="/wiki/Bitter_orange" title="Bitter orange">Bitter orange</a></li> <li><a href="/wiki/Blood_lime" title="Blood lime">Blood lime</a></li> <li><a href="/wiki/Blood_orange" title="Blood orange">Blood orange</a></li> <li><a href="/wiki/Byeonggyul" title="Byeonggyul">Byeonggyul</a></li> <li><a href="/wiki/Biasong" class="mw-redirect" title="Biasong">Biasong</a></li> <li><a href="/wiki/Cam_s%C3%A0nh" title="Cam sành">Cam sành</a></li> <li><a href="/wiki/Cara_Cara_navel_orange" title="Cara Cara navel orange">Cara Cara navel orange</a></li> <li><a href="/wiki/Citrange" title="Citrange">Citrange</a></li> <li><a href="/wiki/Citrumelo" title="Citrumelo">Citrumelo</a></li> <li><a href="/wiki/Clementine" title="Clementine">Clementine</a></li> <li><a href="/wiki/Coorg_orange" title="Coorg orange">Coorg orange</a></li> <li><a href="/wiki/Daidai" title="Daidai">Daidai</a></li> <li><a href="/wiki/Dekopon" title="Dekopon">Dekopon</a></li> <li><a href="/wiki/%27Encore%27_mandarin" title="'Encore' mandarin">Encore</a></li> <li><a href="/wiki/Fairchild_tangerine" title="Fairchild tangerine">Fairchild tangerine</a></li> <li><a href="/wiki/Florentine_citron" title="Florentine citron">Florentine citron</a></li> <li><a href="/wiki/Forbidden_fruit_(citrus)" title="Forbidden fruit (citrus)">Forbidden fruit</a></li> <li><a href="/wiki/Citrus_assamensis" title="Citrus assamensis">Ginger lime</a></li> <li><a href="/wiki/Haruka_(citrus)" title="Haruka (citrus)">Haruka</a></li> <li><a href="/wiki/Hassaku" title="Hassaku">Hassaku</a></li> <li><a href="/wiki/Hebesu" title="Hebesu">Hebesu</a></li> <li><a href="/wiki/Heen_naran" title="Heen naran">Heen naran</a></li> <li><a href="/wiki/Hyuganatsu" title="Hyuganatsu">Hyuganatsu</a></li> <li><a href="/wiki/Imperial_lemon" title="Imperial lemon">Imperial lemon</a></li> <li><a href="/wiki/Citrus_indica" title="Citrus indica">Indian wild orange</a></li> <li><a href="/wiki/Iyokan" title="Iyokan">Iyokan</a></li> <li><a href="/wiki/Jabara_(citrus)" title="Jabara (citrus)">Jabara</a></li> <li><a href="/wiki/Jaffa_orange" title="Jaffa orange">Jaffa orange</a></li> <li><a href="/wiki/Jamaican_tangelo" title="Jamaican tangelo">Jamaican tangelo</a></li> <li><a href="/wiki/Kabbad" title="Kabbad">Kabbad</a></li> <li><a href="/wiki/Kabosu" title="Kabosu">Kabosu</a></li> <li><a href="/wiki/Kaji_Nemu" title="Kaji Nemu">Kaji Nemu</a></li> <li><a href="/wiki/Citrus_gracilis" title="Citrus gracilis">Kakadu lime</a></li> <li><a href="/wiki/Kalpi_(fruit)" title="Kalpi (fruit)">Kalpi</a></li> <li><a href="/wiki/Kanpei" title="Kanpei">Kanpei</a></li> <li><a href="/wiki/Kawachi_bankan" title="Kawachi bankan">Kawachi bankan</a></li> <li><a href="/wiki/Key_lime" title="Key lime">Key lime</a></li> <li><a href="/wiki/Citrus_latipes" title="Citrus latipes">Khasi papeda</a></li> <li><a href="/wiki/Kinkoji_unshiu" title="Kinkoji unshiu">Kinkoji unshiu</a></li> <li><a href="/wiki/Kinnow" title="Kinnow">Kinnow</a></li> <li><a href="/wiki/Kishu_mikan" title="Kishu mikan">Kishu mikan</a></li> <li><a href="/wiki/Kiyomi" title="Kiyomi">Kiyomi</a></li> <li><a href="/wiki/Kobayashi_mikan" title="Kobayashi mikan">Kobayashi mikan</a></li> <li><a href="/wiki/Koji_orange" title="Koji orange">Koji</a></li> <li><a href="/wiki/Komikan_(fruit)" title="Komikan (fruit)">Komikan</a></li> <li><a href="/wiki/Laraha" title="Laraha">Laraha</a></li> <li><a href="/wiki/Lemonade_fruit" title="Lemonade fruit">Lemonade fruit</a></li> <li><a href="/wiki/Lim%C3%B3n_de_Pica" title="Limón de Pica">Limón de Pica</a></li> <li><a href="/wiki/Lumia_(citrus)" title="Lumia (citrus)">Lumia</a></li> <li><a href="/wiki/Mandelo" title="Mandelo">Mandelo</a></li> <li><a href="/wiki/Mandora_(fruit)" title="Mandora (fruit)">Mandora</a></li> <li><a href="/wiki/Citrus_macroptera" title="Citrus macroptera">Melanesian papeda</a></li> <li><a href="/wiki/Melogold" title="Melogold">Melogold</a></li> <li><a href="/wiki/Meyer_lemon" title="Meyer lemon">Meyer lemon</a></li> <li><a href="/wiki/Micrantha_(citrus)" title="Micrantha (citrus)">Micrantha</a></li> <li><a href="/wiki/Midknight_Valencia_Orange" title="Midknight Valencia Orange">Midknight Valencia Orange</a></li> <li><a href="/wiki/Murcott_(fruit)" title="Murcott (fruit)">Murcott</a></li> <li><a href="/wiki/Citrus_myrtifolia" title="Citrus myrtifolia">Myrtle-leaved orange tree</a></li> <li><a href="/wiki/Nagpur_orange" title="Nagpur orange">Nagpur orange</a></li> <li><a href="/wiki/Citrus_%C3%97_amblycarpa" title="Citrus × amblycarpa">Nasnaran</a></li> <li><a href="/wiki/New_Zealand_grapefruit" title="New Zealand grapefruit">New Zealand grapefruit</a></li> <li><a href="/wiki/%C5%8Cgonkan" title="Ōgonkan">Ōgonkan</a></li> <li><a href="/wiki/Orangelo" title="Orangelo">Orangelo/Chironja</a></li> <li><a href="/wiki/Oroblanco" title="Oroblanco">Oroblanco</a></li> <li><a href="/wiki/Palestinian_sweet_lime" title="Palestinian sweet lime">Palestinian sweet lime</a></li> <li><a href="/wiki/Persian_lime" title="Persian lime">Persian lime</a></li> <li><a href="/wiki/Pixie_mandarin" title="Pixie mandarin">Pixie mandarin</a></li> <li><a href="/wiki/Pompia" title="Pompia">Pompia</a></li> <li><a href="/wiki/Ponderosa_lemon" title="Ponderosa lemon">Ponderosa lemon</a></li> <li><a href="/wiki/Ponkan" title="Ponkan">Ponkan</a></li> <li><a href="/wiki/Rangpur_(fruit)" title="Rangpur (fruit)">Rangpur</a></li> <li><a href="/wiki/Reikou" title="Reikou">Reikou</a></li> <li><a href="/wiki/Rhobs_el_Arsa" title="Rhobs el Arsa">Rhobs el Arsa</a></li> <li><a href="/wiki/Rough_lemon" title="Rough lemon">Rough lemon</a></li> <li><a href="/wiki/Samuyao" class="mw-redirect" title="Samuyao">Samuyao</a></li> <li><a href="/wiki/Sanbokan" title="Sanbokan">Sanbokan</a></li> <li><a href="/wiki/Citrus_unshiu" title="Citrus unshiu">Satsuma mandarin</a></li> <li><a href="/wiki/Setoka" title="Setoka">Setoka</a></li> <li><a href="/wiki/Shangjuan" title="Shangjuan">Shangjuan</a></li> <li><a href="/wiki/Shonan_Gold" title="Shonan Gold">Shonan Gold</a></li> <li><a href="/wiki/Smith_Red_Valencia" title="Smith Red Valencia">Smith Red Valencia</a></li> <li><a href="/wiki/Sudachi" title="Sudachi">Sudachi</a></li> <li><a href="/wiki/Koji_orange#Varieties" title="Koji orange">Suruga yuko</a></li> <li><a href="/wiki/Sweet_lemon" title="Sweet lemon">Sweet lemon</a></li> <li><a href="/wiki/Citrus_limetta" title="Citrus limetta">Sweet limetta</a></li> <li><a href="/wiki/Tangelo" title="Tangelo">Tangelo</a></li> <li><a href="/wiki/Tangerine" title="Tangerine">Tangerine</a></li> <li><a href="/wiki/Tangor" title="Tangor">Tangor</a></li> <li><a href="/wiki/Tsunonozomi" title="Tsunonozomi">Tsunonozomi</a></li> <li><a href="/wiki/Valencia_orange" title="Valencia orange">Valencia orange</a></li> <li><a href="/wiki/Variegated_pink_lemon" title="Variegated pink lemon">Variegated pink lemon</a></li> <li><a href="/wiki/Volkamer_lemon" title="Volkamer lemon">Volkamer lemon</a></li> <li><a href="/wiki/Citrus_longispina" title="Citrus longispina">Winged lime</a></li> <li><a href="/wiki/X%C3%A3_%C4%90o%C3%A0i_orange" title="Xã Đoài orange">Xã Đoài orange</a></li> <li><a href="/wiki/Y%C5%ABk%C5%8D" title="Yūkō">Yūkō</a></li> <li><a href="/wiki/Yuzu" title="Yuzu">Yuzu</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Citron" title="Citron">Citrons</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/Balady_citron" title="Balady citron">Balady citron</a></li> <li><a href="/wiki/Corsican_citron" title="Corsican citron">Corsican citron</a></li> <li><a href="/wiki/Diamante_citron" title="Diamante citron">Diamante citron</a></li> <li><a href="/wiki/Fingered_citron" class="mw-redirect" title="Fingered citron">Fingered citron/Buddha's hand</a></li> <li><a href="/wiki/Greek_citron" title="Greek citron">Greek citron</a></li> <li><a href="/wiki/Moroccan_citron" title="Moroccan citron">Moroccan citron</a></li> <li><a href="/wiki/Yemenite_citron" title="Yemenite citron">Yemenite citron</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Mandarin_orange_varieties" title="Mandarin orange varieties">Mandarin oranges</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/Citrus_reshni" title="Citrus reshni">Cleopatra mandarin</a></li> <li><a href="/wiki/Citrus_depressa" title="Citrus depressa">Shīkwāsā</a></li> <li><a href="/wiki/Nanfengmiju" title="Nanfengmiju">Nanfengmiju</a></li> <li><a href="/wiki/Tachibana_orange" title="Tachibana orange">Tachibana</a></li> <li><a href="/wiki/Citrus_x_deliciosa" class="mw-redirect" title="Citrus x deliciosa">Willowleaf orange</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Papeda_(citrus)" title="Papeda (citrus)">Papedas</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/Citrus_celebica" class="mw-redirect" title="Citrus celebica">Celebes papeda</a></li> <li><a href="/wiki/Citrus_halimii" title="Citrus halimii">Mountain "citron"</a></li> <li><a href="/wiki/Citrus_ichangensis" class="mw-redirect" title="Citrus ichangensis">Ichang papeda</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Pomelos" class="mw-redirect" title="Pomelos">Pomelos</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/Banpeiyu" title="Banpeiyu">Banpeiyu</a></li> <li><a href="/wiki/Dangyuja" title="Dangyuja">Dangyuja</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Kumquat" title="Kumquat">Kumquats</a> group</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">Kumquat species</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/Citrus_hindsii" title="Citrus hindsii">Hong Kong kumquat</a></li> <li><a href="/wiki/Citrus_crassifolia" title="Citrus crassifolia">Meiwa kumquat</a></li> <li><a href="/wiki/Citrus_margarita" title="Citrus margarita">Oval kumquat</a></li> <li><a href="/wiki/Citrus_japonica" title="Citrus japonica">Round kumquat</a></li> <li><a href="/wiki/Citrus_obovata" title="Citrus obovata">Jiangsu kumquat</a></li> <li><a href="/wiki/Citrus_swinglei" title="Citrus swinglei">Malayan kumquat</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Kumquat hybrids <br />(<a href="/wiki/Hybrid_name" title="Hybrid name">×</a> <a href="/wiki/Citrofortunella" title="Citrofortunella">Citrofortunella</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/Calamansi" title="Calamansi">Calamansi</a></li> <li><a href="/wiki/Citrangequat" title="Citrangequat">Citrangequat</a></li> <li><a href="/wiki/Limequat" title="Limequat">Limequat</a></li> <li><a href="/wiki/Mandarinquat" title="Mandarinquat">Mandarinquat</a></li> <li><a href="/wiki/Procimequat" title="Procimequat">Procimequat</a></li> <li><a href="/wiki/Sunquat" title="Sunquat">Sunquat</a></li> <li><a href="/wiki/Yuzuquat" title="Yuzuquat">Yuzuquat</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/Australian_lime" title="Australian lime">Australian<br />and Papuan<br />wild limes group</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><i>Eromocitrus</i> <br /> <small>(former genera)</small></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/Citrus_glauca" title="Citrus glauca">Desert lime</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><i>Microcitrus</i> <br /> <small>(former genera)</small></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/Citrus_warburgiana" title="Citrus warburgiana">New Guinea wild lime</a></li> <li><a href="/wiki/Citrus_australis" title="Citrus australis">Australian round lime</a></li> <li><a href="/wiki/Citrus_inodora" title="Citrus inodora">Russell River lime</a></li> <li><a href="/wiki/Citrus_maideniana" class="mw-redirect" title="Citrus maideniana">Maiden's wild lime</a></li> <li><a href="/wiki/Citrus_garrawayi" title="Citrus garrawayi">Mount White lime</a></li> <li><a href="/wiki/Citrus_australasica" title="Citrus australasica">Australian finger lime</a></li> <li><a href="/wiki/Citrus_wintersii" title="Citrus wintersii">Brown River finger lime</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><i><a href="/wiki/Clymenia_(plant)" title="Clymenia (plant)">Clymenia</a></i> <br /> <small>(former genera)</small></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="/w/index.php?title=Clymenia_platypoda&action=edit&redlink=1" class="new" title="Clymenia platypoda (page does not exist)">Clymenia platypoda</a></li> <li><a href="/w/index.php?title=Clymenia_polyandra&action=edit&redlink=1" class="new" title="Clymenia polyandra (page does not exist)">Clymenia polyandra</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><i><a href="/wiki/False_orange" title="False orange">Oxanthera</a></i> <br /> <small>(former genera)</small></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/Citrus_oxanthera" title="Citrus oxanthera">Orange-flowered oxanthera</a></li> <li><a href="/wiki/Citrus_neocaledonica" title="Citrus neocaledonica">Large-leaf oxanthera</a></li> <li><a href="/wiki/Citrus_undulata" title="Citrus undulata">Wavy-leaf oxanthera</a></li> <li><i><a href="/wiki/Oxanthera_brevipes" title="Oxanthera brevipes">Oxanthera brevipes</a></i></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Citrus_taxonomy#Trifoliate_orange" title="Citrus taxonomy">Related genera</a><br />(perhaps<br />properly <i>Citrus</i>)</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><a href="/wiki/Trifoliate_orange" title="Trifoliate orange">Poncirus</a></i>/<a href="/wiki/Trifoliate_orange" title="Trifoliate orange">Trifoliate orange</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Drinks</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/Calamansi_juice" class="mw-redirect" title="Calamansi juice">Calamansi juice</a></li> <li><a href="/wiki/Ch%C5%ABhai" title="Chūhai">Chūhai</a></li> <li><a href="/wiki/Cura%C3%A7ao_(liqueur)" title="Curaçao (liqueur)">Curaçao</a></li> <li><a href="/wiki/Dried_lime_tea" title="Dried lime tea">Dried lime tea (noomi basra)</a></li> <li><a href="/wiki/Grapefruit_juice" title="Grapefruit juice">Grapefruit juice</a></li> <li><a href="/wiki/Lemonade" title="Lemonade">Lemonade</a></li> <li><a href="/wiki/Limeade" title="Limeade">Limeade</a></li> <li><a href="/wiki/Orange_juice" title="Orange juice">Orange juice</a></li> <li><a href="/wiki/Yuja-hwachae" title="Yuja-hwachae">Yuja-hwachae</a></li> <li><a href="/wiki/Yuja_tea" title="Yuja tea">Yuja tea</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Products</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Calcium_citrate" title="Calcium citrate">Calcium citrate</a></li> <li><a href="/wiki/Citric_acid" title="Citric acid">Citric acid</a></li> <li><a href="/wiki/Biphenyl" title="Biphenyl">Lemonene</a></li> <li><a class="mw-selflink selflink">Limonene</a></li> <li><a href="/wiki/Neroli" title="Neroli">Neroli</a></li> <li><a href="/wiki/Orange_flower_water" title="Orange flower water">Orange flower water</a></li> <li><a href="/wiki/Orange_oil" title="Orange oil">Orange oil</a></li> <li><a href="/wiki/Orangeat" class="mw-redirect" title="Orangeat">Orangeat</a></li> <li><a href="/wiki/Succade" title="Succade">Succade</a></li> <li><a href="/wiki/Zest_(ingredient)" title="Zest (ingredient)">Zest</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_citrus_diseases" title="List of citrus diseases">Diseases</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/Citrus_black_spot" title="Citrus black spot">Black spot</a></li> <li><a href="/wiki/Citrus_canker" title="Citrus canker">Canker</a></li> <li><a href="/wiki/Citrus_tristeza_virus" title="Citrus tristeza virus">CTV/Tristeza</a></li> <li><a href="/wiki/Citrus_exocortis" title="Citrus exocortis">Exocortis</a></li> <li><a href="/wiki/Citrus_greening_disease" title="Citrus greening disease">Greening</a></li> <li><a href="/wiki/Phoma_tracheiphila" title="Phoma tracheiphila">Mal secco</a></li> <li><a href="/wiki/Phytophthora" title="Phytophthora">Phytophthora</a> <ul><li><a href="/wiki/Phytophthora_citricola" title="Phytophthora citricola">citricola</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Citrus botanists</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/Clara_H._Hasse" title="Clara H. Hasse">Clara H. Hasse</a></li> <li><a href="/wiki/Robert_Willard_Hodgson" title="Robert Willard Hodgson">Robert Willard Hodgson</a></li> <li><a href="/wiki/Lena_B._Smithers_Hughes" title="Lena B. Smithers Hughes">Lena B. Smithers Hughes</a></li> <li><a href="/wiki/David_Mabberley" title="David Mabberley">David Mabberley</a></li> <li><a href="/wiki/Cl%C3%A9ment_Rodier" title="Clément Rodier">Clément Rodier</a></li> <li><a href="/wiki/Robert_Soost" title="Robert Soost">Robert Soost</a></li> <li><a href="/wiki/Walter_Tennyson_Swingle" title="Walter Tennyson Swingle">Walter Tennyson Swingle</a></li> <li><a href="/wiki/Ch%C5%8Dzabur%C5%8D_Tanaka" title="Chōzaburō Tanaka">Chōzaburō Tanaka</a></li> <li><a href="/wiki/Ikuro_Takahashi_(botanist)" title="Ikuro Takahashi (botanist)">Ikuro Takahashi</a></li> <li><a href="/wiki/Johann_Christoph_Volkamer" title="Johann Christoph Volkamer">Johann Christoph Volkamer</a></li> <li><a href="/wiki/Herbert_John_Webber" title="Herbert John Webber">Herbert John Webber</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Related topics</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i><a href="/wiki/The_Citrus_Industry" title="The Citrus Industry">The Citrus Industry</a></i></li> <li><a href="/wiki/Citrus_production" title="Citrus production">Citrus production</a></li> <li><a href="/wiki/Citrus_rootstock" title="Citrus rootstock">Citrus rootstock</a></li> <li><a href="/wiki/Citrus_taxonomy" title="Citrus taxonomy">Citrus taxonomy</a></li> <li><a href="/wiki/Cold-hardy_citrus" title="Cold-hardy citrus">Cold-hardy citrus</a></li> <li><a href="/wiki/Hesperidium" title="Hesperidium">Hesperidium</a></li> <li><a href="/wiki/Japanese_citrus" title="Japanese citrus">Japanese citrus</a></li> <li><a href="/wiki/List_of_citrus_fruits" title="List of citrus fruits">List of citrus fruits</a></li> <li><a href="/wiki/Mother_Orange_Tree" title="Mother Orange Tree">Mother Orange Tree</a></li> <li><a href="/wiki/Orangery" title="Orangery">Orangery</a></li> <li><a href="/wiki/University_of_California_Citrus_Experiment_Station" title="University of California Citrus Experiment Station">University of California Citrus Experiment Station</a></li> <li><a href="/wiki/University_of_California,_Riverside_Citrus_Variety_Collection" class="mw-redirect" title="University of California, Riverside Citrus Variety Collection">University of California, Riverside Citrus Variety Collection</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <ul><li><span class="noviewer" typeof="mw:File"><span title="Category"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/16px-Symbol_category_class.svg.png" decoding="async" width="16" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/23px-Symbol_category_class.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/31px-Symbol_category_class.svg.png 2x" data-file-width="180" data-file-height="185" /></span></span> <b><a href="/wiki/Category:Citrus" title="Category:Citrus">Category</a></b></li> <li><span class="noviewer" typeof="mw:File"><span title="Category"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/16px-Symbol_category_class.svg.png" decoding="async" width="16" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/23px-Symbol_category_class.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/31px-Symbol_category_class.svg.png 2x" data-file-width="180" data-file-height="185" /></span></span> <b><a href="/wiki/Category:Citrus_production" title="Category:Citrus production">Production</a></b></li> <li><span class="noviewer" typeof="mw:File"><span title="Commons page"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/12px-Commons-logo.svg.png" decoding="async" width="12" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/18px-Commons-logo.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/24px-Commons-logo.svg.png 2x" data-file-width="1024" data-file-height="1376" /></span></span> <b><a href="https://commons.wikimedia.org/wiki/Category:Citrus" class="extiw" title="commons:Category:Citrus">Commons</a></b></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Types_of_terpenes_and_terpenoids_(#_of_isoprene_units)435" style="padding:3px"><table class="nowraplinks mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Terpenoids" title="Template:Terpenoids"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Terpenoids" title="Template talk:Terpenoids"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Terpenoids" title="Special:EditPage/Template:Terpenoids"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Types_of_terpenes_and_terpenoids_(#_of_isoprene_units)435" style="font-size:114%;margin:0 4em">Types of <a href="/wiki/Terpene" title="Terpene">terpenes</a> and <a href="/wiki/Terpenoid" title="Terpenoid">terpenoids</a> (# of <a href="/wiki/Isoprene" title="Isoprene">isoprene</a> units)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">Basic forms:</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Acyclic (linear, <i>cis</i> and <i>trans</i> forms)</li> <li>Monocyclic (single ring)</li> <li>Bicyclic (2 rings)</li> <li><a href="/wiki/Iridoid" title="Iridoid">Iridoids</a> (cyclopentane ring)</li> <li>Iridoid glycosides (iridoids bound to a sugar)</li> <li><a href="/wiki/Steroid" title="Steroid">Steroids</a> (4 rings)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Hemiterpenoid" class="mw-redirect" title="Hemiterpenoid">Hemiterpenoids</a> (1)</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Isoprene" title="Isoprene">Isoprene</a> (C<sub>5</sub>H<sub>8</sub>)</li> <li><a href="/wiki/Prenol" title="Prenol">Prenol</a></li> <li><a href="/wiki/Isovaleric_acid" title="Isovaleric acid">Isovaleric acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Monoterpene" title="Monoterpene">Monoterpenes</a> <br />(C<sub>10</sub>H<sub>16</sub>)(2)</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">Acyclic</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Ocimene" title="Ocimene">Ocimene</a></li> <li><a href="/wiki/Myrcene" title="Myrcene">Myrcenes</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Monocyclic</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a class="mw-selflink selflink">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><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" data-nosnippet="">Retrieved from "<a dir="ltr" href="https://en.wikipedia.org/w/index.php?title=Limonene&oldid=1269440812">https://en.wikipedia.org/w/index.php?title=Limonene&oldid=1269440812</a>"</div></div> <div id="catlinks" class="catlinks" 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