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vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Occurrence_and_uses"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Occurrence and uses</span> </div> </a> <button aria-controls="toc-Occurrence_and_uses-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Occurrence and uses subsection</span> </button> <ul id="toc-Occurrence_and_uses-sublist" class="vector-toc-list"> <li id="toc-Production_of_hydrogen_peroxide" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Production_of_hydrogen_peroxide"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.1</span> <span>Production of hydrogen peroxide</span> </div> </a> <ul id="toc-Production_of_hydrogen_peroxide-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Biochemistry" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Biochemistry"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.2</span> <span>Biochemistry</span> </div> </a> <ul id="toc-Biochemistry-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Medical" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Medical"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.3</span> <span>Medical</span> </div> </a> <ul id="toc-Medical-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Dyes" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Dyes"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.4</span> <span>Dyes</span> </div> </a> <ul id="toc-Dyes-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Photography" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Photography"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.5</span> <span>Photography</span> </div> </a> <ul id="toc-Photography-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Nomenclature" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Nomenclature"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Nomenclature</span> </div> </a> <ul id="toc-Nomenclature-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Structural_analogues_of_quinones" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Structural_analogues_of_quinones"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Structural analogues of quinones</span> </div> </a> <ul id="toc-Structural_analogues_of_quinones-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>External links</span> </div> </a> <ul id="toc-External_links-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" title="Table of Contents" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" 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Available in 36 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-36" 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">36 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%83%D9%8A%D9%86%D9%88%D9%86" title="كينون – Arabic" lang="ar" hreflang="ar" data-title="كينون" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-be mw-list-item"><a href="https://be.wikipedia.org/wiki/%D0%A5%D1%96%D0%BD%D0%BE%D0%BD%D1%8B" title="Хіноны – Belarusian" lang="be" hreflang="be" data-title="Хіноны" data-language-autonym="Беларуская" data-language-local-name="Belarusian" class="interlanguage-link-target"><span>Беларуская</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Quinona" title="Quinona – Catalan" lang="ca" hreflang="ca" data-title="Quinona" 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/Chinony" title="Chinony – Czech" lang="cs" hreflang="cs" data-title="Chinony" 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/Quinon" title="Quinon – Danish" lang="da" hreflang="da" data-title="Quinon" 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/Chinone" title="Chinone – German" lang="de" hreflang="de" data-title="Chinone" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Quinona" title="Quinona – Spanish" lang="es" hreflang="es" data-title="Quinona" 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/Kinono" title="Kinono – Esperanto" lang="eo" hreflang="eo" data-title="Kinono" 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/Kinona" title="Kinona – Basque" lang="eu" hreflang="eu" data-title="Kinona" 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/%DA%A9%DB%8C%D9%86%D9%88%D9%86" title="کینون – Persian" lang="fa" hreflang="fa" data-title="کینون" 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/Quinone" title="Quinone – French" lang="fr" hreflang="fr" data-title="Quinone" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ga mw-list-item"><a href="https://ga.wikipedia.org/wiki/Cuineon" title="Cuineon – Irish" lang="ga" hreflang="ga" data-title="Cuineon" data-language-autonym="Gaeilge" data-language-local-name="Irish" class="interlanguage-link-target"><span>Gaeilge</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Quinona" title="Quinona – Galician" lang="gl" hreflang="gl" data-title="Quinona" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%ED%80%B4%EB%85%BC" title="퀴논 – Korean" lang="ko" hreflang="ko" data-title="퀴논" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hi mw-list-item"><a href="https://hi.wikipedia.org/wiki/%E0%A4%95%E0%A5%8D%E0%A4%B5%E0%A4%BF%E0%A4%A8%E0%A5%8B%E0%A4%A8" title="क्विनोन – Hindi" lang="hi" hreflang="hi" data-title="क्विनोन" data-language-autonym="हिन्दी" data-language-local-name="Hindi" class="interlanguage-link-target"><span>हिन्दी</span></a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Kinoni" title="Kinoni – Croatian" lang="hr" hreflang="hr" data-title="Kinoni" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Kuinona" title="Kuinona – Indonesian" lang="id" hreflang="id" data-title="Kuinona" 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/Chinoni" title="Chinoni – Italian" lang="it" hreflang="it" data-title="Chinoni" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-kk mw-list-item"><a href="https://kk.wikipedia.org/wiki/%D0%A5%D0%B8%D0%BD%D0%BE%D0%BD%D0%B4%D0%B0%D1%80" title="Хинондар – Kazakh" lang="kk" hreflang="kk" data-title="Хинондар" data-language-autonym="Қазақша" data-language-local-name="Kazakh" class="interlanguage-link-target"><span>Қазақша</span></a></li><li class="interlanguage-link interwiki-kv mw-list-item"><a href="https://kv.wikipedia.org/wiki/%D0%A5%D0%B8%D0%BD%D0%BE%D0%BB%D0%BE%D0%BD%D1%8A%D1%8F%D1%81" title="Хинолонъяс – Komi" lang="kv" hreflang="kv" data-title="Хинолонъяс" data-language-autonym="Коми" data-language-local-name="Komi" class="interlanguage-link-target"><span>Коми</span></a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Hinoni" title="Hinoni – Latvian" lang="lv" hreflang="lv" data-title="Hinoni" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target"><span>Latviešu</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Kinonok" title="Kinonok – Hungarian" lang="hu" hreflang="hu" data-title="Kinonok" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Chinon_(scheikunde)" title="Chinon (scheikunde) – Dutch" lang="nl" hreflang="nl" data-title="Chinon (scheikunde)" 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%82%AD%E3%83%8E%E3%83%B3" title="キノン – Japanese" lang="ja" hreflang="ja" data-title="キノン" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Chinony" title="Chinony – Polish" lang="pl" hreflang="pl" data-title="Chinony" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Chinon%C4%83" title="Chinonă – Romanian" lang="ro" hreflang="ro" data-title="Chinonă" 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%A5%D0%B8%D0%BD%D0%BE%D0%BD%D1%8B" title="Хиноны – Russian" lang="ru" hreflang="ru" data-title="Хиноны" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Hinon" title="Hinon – Serbian" lang="sr" hreflang="sr" data-title="Hinon" 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/Hinon" title="Hinon – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Hinon" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Kinonit" title="Kinonit – Finnish" lang="fi" hreflang="fi" data-title="Kinonit" 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/Kinon" title="Kinon – Swedish" lang="sv" hreflang="sv" data-title="Kinon" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%95%E0%AF%81%E0%AE%AF%E0%AE%BF%E0%AE%A9%E0%AF%8B%E0%AE%A9%E0%AF%8D" title="குயினோன் – Tamil" lang="ta" hreflang="ta" data-title="குயினோன்" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%A5%D1%96%D0%BD%D0%BE%D0%BD%D0%B8" title="Хінони – Ukrainian" lang="uk" hreflang="uk" data-title="Хінони" 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/Quinon" title="Quinon – Vietnamese" lang="vi" hreflang="vi" data-title="Quinon" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target"><span>Tiếng Việt</span></a></li><li class="interlanguage-link interwiki-wuu mw-list-item"><a href="https://wuu.wikipedia.org/wiki/%E9%86%8C" title="醌 – Wu" lang="wuu" hreflang="wuu" data-title="醌" data-language-autonym="吴语" data-language-local-name="Wu" class="interlanguage-link-target"><span>吴语</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E9%86%8C" title="醌 – 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class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Compounds having a fully conjugated cyclic dione structure</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">"Quinones" redirects here; not to be confused with <a href="/wiki/Qui%C3%B1%C3%B3nez" title="Quiñónez">Quiñones</a>, <a href="/wiki/Quinine" title="Quinine">Quinine</a>, or <a href="/wiki/Hydroquinone" title="Hydroquinone">Hydroquinone</a>.</div> <p>The <b>quinones</b> are a class of <a href="/wiki/Organic_compound" title="Organic compound">organic compounds</a> that are formally "derived from <a href="/wiki/Aromatic" class="mw-redirect" title="Aromatic">aromatic</a> compounds [such as <a href="/wiki/Benzene" title="Benzene">benzene</a> or <a href="/wiki/Naphthalene" title="Naphthalene">naphthalene</a>] by conversion of an even number of –CH= groups into –C(=O)– groups with any necessary rearrangement of <a href="/wiki/Double_bond" title="Double bond">double bonds</a>", resulting in "a fully <a href="/wiki/Conjugated_system" title="Conjugated system">conjugated</a> cyclic <a href="/wiki/Diketone" class="mw-redirect" title="Diketone">dione</a> structure".<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><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> The archetypical member of the class is <a href="/wiki/1,4-benzoquinone" class="mw-redirect" title="1,4-benzoquinone">1,4-benzoquinone</a> or cyclohexadienedione, often called simply "quinone" (thus the name of the class). Other important examples are <a href="/wiki/1,2-benzoquinone" class="mw-redirect" title="1,2-benzoquinone">1,2-benzoquinone</a> (<b><i>ortho</i>-quinone</b>), <a href="/wiki/1,4-naphthoquinone" class="mw-redirect" title="1,4-naphthoquinone">1,4-naphthoquinone</a> and <a href="/wiki/Anthraquinone" title="Anthraquinone">9,10-anthraquinone</a>. </p><p>The name is derived from that of <a href="/wiki/Quinic_acid" title="Quinic acid">quinic acid</a> (with the suffix "-one" indicating a ketone), since it is one of the compounds obtained upon oxidation of quinic acid.<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> Quinic acid, like <a href="/wiki/Quinine" title="Quinine">quinine</a> is obtained from <a href="/wiki/Cinchona_bark" class="mw-redirect" title="Cinchona bark">cinchona bark</a>, called <a href="https://en.wiktionary.org/wiki/quinaquina" class="extiw" title="wikt:quinaquina">quinaquina</a> in the indigenous languages of Peruvian tribes. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Properties">Properties</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Quinone&action=edit&section=1" title="Edit section: Properties"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Quinones are oxidized derivatives of aromatic compounds and are often readily made from reactive aromatic compounds with <a href="/wiki/Electron-donating_group" class="mw-redirect" title="Electron-donating group">electron-donating substituents</a> such as <a href="/wiki/Phenols" title="Phenols">phenols</a> and <a href="/wiki/Catechol" title="Catechol">catechols</a>, which increase the nucleophilicity of the ring and contributes to the large <a href="/wiki/Redox_potential" class="mw-redirect" title="Redox potential">redox potential</a> needed to break aromaticity. (Quinones are conjugated but not aromatic). Quinones are electrophilic <a href="/wiki/Michael_acceptor" class="mw-redirect" title="Michael acceptor">Michael acceptors</a> stabilised by conjugation. Depending on the quinone and the site of reduction, reduction can either rearomatise the compound or break the conjugation. <a href="/wiki/Conjugate_addition" class="mw-redirect" title="Conjugate addition">Conjugate addition</a> nearly always breaks the conjugation. </p> <ul class="gallery mw-gallery-traditional skin-invert-image"> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Orthobenzoquinone.svg" class="mw-file-description" title="1,2-Benzoquinone"><img alt="1,2-Benzoquinone" src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0b/Orthobenzoquinone.svg/104px-Orthobenzoquinone.svg.png" decoding="async" width="104" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0b/Orthobenzoquinone.svg/156px-Orthobenzoquinone.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/0b/Orthobenzoquinone.svg/207px-Orthobenzoquinone.svg.png 2x" data-file-width="83" data-file-height="96" /></a></span></div> <div class="gallerytext"><a href="/wiki/1,2-Benzoquinone" title="1,2-Benzoquinone">1,2-Benzoquinone</a></div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:P-Benzochinon.svg" class="mw-file-description" title="1,4-Benzoquinone"><img alt="1,4-Benzoquinone" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e4/P-Benzochinon.svg/60px-P-Benzochinon.svg.png" decoding="async" width="48" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e4/P-Benzochinon.svg/120px-P-Benzochinon.svg.png 1.5x" data-file-width="801" data-file-height="1992" /></a></span></div> <div class="gallerytext"><a href="/wiki/1,4-Benzoquinone" title="1,4-Benzoquinone">1,4-Benzoquinone</a></div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:1,4-Naphthoquinone.svg" class="mw-file-description" title="1,4-Naphthoquinone"><img alt="1,4-Naphthoquinone" src="//upload.wikimedia.org/wikipedia/commons/thumb/1/19/1%2C4-Naphthoquinone.svg/120px-1%2C4-Naphthoquinone.svg.png" decoding="async" width="96" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/19/1%2C4-Naphthoquinone.svg/250px-1%2C4-Naphthoquinone.svg.png 1.5x" data-file-width="423" data-file-height="528" /></a></span></div> <div class="gallerytext"><a href="/wiki/1,4-Naphthoquinone" title="1,4-Naphthoquinone">1,4-Naphthoquinone</a></div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Anthrachinon.svg" class="mw-file-description" title="9,10-Anthraquinone"><img alt="9,10-Anthraquinone" src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d7/Anthrachinon.svg/120px-Anthrachinon.svg.png" decoding="async" width="120" height="102" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d7/Anthrachinon.svg/180px-Anthrachinon.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d7/Anthrachinon.svg/240px-Anthrachinon.svg.png 2x" data-file-width="208" data-file-height="176" /></a></span></div> <div class="gallerytext"><a href="/wiki/Anthraquinone" title="Anthraquinone">9,10-Anthraquinone</a></div> </li> </ul> <p>The term <b>quinone</b> is also used more generally for a large class of compounds formally derived from aromatic quinones through replacement of some <a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a> atoms by other atoms or radicals. </p> <ul class="gallery mw-gallery-traditional skin-invert-image"> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:2,3,5,6-tetrachloro-parabenzoquinone.svg" class="mw-file-description" title="Chloranil, a reagent in organic chemistry"><img alt="Chloranil, a reagent in organic chemistry" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/62/2%2C3%2C5%2C6-tetrachloro-parabenzoquinone.svg/120px-2%2C3%2C5%2C6-tetrachloro-parabenzoquinone.svg.png" decoding="async" width="118" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/62/2%2C3%2C5%2C6-tetrachloro-parabenzoquinone.svg/177px-2%2C3%2C5%2C6-tetrachloro-parabenzoquinone.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/62/2%2C3%2C5%2C6-tetrachloro-parabenzoquinone.svg/236px-2%2C3%2C5%2C6-tetrachloro-parabenzoquinone.svg.png 2x" data-file-width="220" data-file-height="224" /></a></span></div> <div class="gallerytext"><a href="/wiki/Chloranil" title="Chloranil">Chloranil</a>, a reagent in organic chemistry</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:HNQ.svg" class="mw-file-description" title="Lawsone, a dye present in the leaves of the henna plant"><img alt="Lawsone, a dye present in the leaves of the henna plant" src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d4/HNQ.svg/120px-HNQ.svg.png" decoding="async" width="120" height="108" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d4/HNQ.svg/250px-HNQ.svg.png 1.5x" data-file-width="620" data-file-height="557" /></a></span></div> <div class="gallerytext"><a href="/wiki/Lawsone" title="Lawsone">Lawsone</a>, a dye present in the leaves of the henna plant</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Alizaryna.svg" class="mw-file-description" title="Alizarin, a common red dye"><img alt="Alizarin, a common red dye" src="//upload.wikimedia.org/wikipedia/commons/thumb/9/9b/Alizaryna.svg/120px-Alizaryna.svg.png" decoding="async" width="120" height="80" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/9b/Alizaryna.svg/250px-Alizaryna.svg.png 1.5x" data-file-width="338" data-file-height="226" /></a></span></div> <div class="gallerytext"><a href="/wiki/Alizarin" title="Alizarin">Alizarin</a>, a common red dye</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Dichlorodicyanobenzoquinone.svg" class="mw-file-description" title="DDQ, a reagent in organic chemistry"><img alt="DDQ, a reagent in organic chemistry" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/66/Dichlorodicyanobenzoquinone.svg/120px-Dichlorodicyanobenzoquinone.svg.png" decoding="async" width="120" height="108" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/66/Dichlorodicyanobenzoquinone.svg/250px-Dichlorodicyanobenzoquinone.svg.png 1.5x" data-file-width="620" data-file-height="556" /></a></span></div> <div class="gallerytext"><a href="/wiki/2,3-Dichloro-5,6-dicyano-1,4-benzoquinone" title="2,3-Dichloro-5,6-dicyano-1,4-benzoquinone">DDQ</a>, a reagent in organic chemistry</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Daunorubicin2DACS.svg" class="mw-file-description" title="Daunorubicin, an anticancer drug"><img alt="Daunorubicin, an anticancer drug" src="//upload.wikimedia.org/wikipedia/commons/thumb/7/73/Daunorubicin2DACS.svg/120px-Daunorubicin2DACS.svg.png" decoding="async" width="120" height="85" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/73/Daunorubicin2DACS.svg/250px-Daunorubicin2DACS.svg.png 1.5x" data-file-width="711" data-file-height="505" /></a></span></div> <div class="gallerytext"><a href="/wiki/Daunorubicin" title="Daunorubicin">Daunorubicin</a>, an anticancer drug</div> </li> </ul> <div class="mw-heading mw-heading2"><h2 id="Reactions">Reactions</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Quinone&action=edit&section=2" title="Edit section: Reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Quinones form polymers by formation of hydrogen bonds with ρ-hydroquinone.<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Reduction">Reduction</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Quinone&action=edit&section=3" title="Edit section: Reduction"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Quinones are <a href="/wiki/Oxidizing_agent" title="Oxidizing agent">oxidizing agents</a>, sometimes reversibly so. Relative to <a href="/wiki/Benzoquinone" title="Benzoquinone">benzoquinone</a>, more strongly oxidizing quinones include <a href="/wiki/Chloranil" title="Chloranil">chloranil</a> and <a href="/wiki/2,3-Dichloro-5,6-dicyano-1,4-benzoquinone" title="2,3-Dichloro-5,6-dicyano-1,4-benzoquinone">2,3-dichloro-5,6-dicyano-1,4-benzoquinone</a> (also known as DDQ).<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p><p>The oxidizing power of quinones is enhanced by the presence of acids.<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> In acidic conditions, quinone undergoes two-electron and two-proton reduction to <a href="/wiki/Hydroquinone" title="Hydroquinone">hydroquinone</a>. </p> <figure class="mw-halign-center skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:QuinoneAcidicReduction.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/3f/QuinoneAcidicReduction.png/247px-QuinoneAcidicReduction.png" decoding="async" width="247" height="152" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/3f/QuinoneAcidicReduction.png/371px-QuinoneAcidicReduction.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/3f/QuinoneAcidicReduction.png/494px-QuinoneAcidicReduction.png 2x" data-file-width="868" data-file-height="533" /></a><figcaption>Reduction of quinone in an acidic, buffered media into hydroquinone</figcaption></figure> <p>In alkaline conditions, quinones undergo a reversible single-step, two-electron reduction. In neutral conditions, quinones may undergo either a one-proton, two-electron reduction or a two-electron reduction.  In <a href="/wiki/Aprotic" class="mw-redirect" title="Aprotic">aprotic</a> media, quinones undergo two-step reduction without protons.<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> In the first step, a short-lived <a href="/wiki/Semiquinone" title="Semiquinone">semiquinone</a> intermediate is formed. In the second step, the semiquinone is reduced into a quinone dianion. </p><p>9,10-Anthraquinone-2,7-disulphonic acid (AQDS) a quinone similar to one found naturally in <a href="/wiki/Rhubarb" title="Rhubarb">rhubarb</a> has been used as a charge carrier in metal-free <a href="/wiki/Flow_battery" title="Flow battery">flow batteries</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> </p> <div class="mw-heading mw-heading3"><h3 id="Addition">Addition</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Quinone&action=edit&section=4" title="Edit section: Addition"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Quinones undergo addition reaction to form 1,4-addition products.<sup id="cite_ref-:0_10-0" class="reference"><a href="#cite_note-:0-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> An example of 1,4-addition reaction is the addition of <a href="/wiki/Hydrogen_chloride" title="Hydrogen chloride">hydrogen chloride</a> to form chlorohydroquinone:   </p> <figure class="mw-halign-center skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:QuinoneAdditionReaction.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/44/QuinoneAdditionReaction.png/250px-QuinoneAdditionReaction.png" decoding="async" width="240" height="119" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/44/QuinoneAdditionReaction.png/500px-QuinoneAdditionReaction.png 1.5x" data-file-width="1115" data-file-height="552" /></a><figcaption>1,4-addition reaction of quinone with hydrogen chloride to produce chlorohydroquinone</figcaption></figure> <p>Quinones can undergo <a href="/wiki/Diels%E2%80%93Alder_reaction" title="Diels–Alder reaction">Diels–Alder reactions</a>.<sup id="cite_ref-:0_10-1" class="reference"><a href="#cite_note-:0-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> The quinone acts as the dienophile and reacts with a diene at a carbon-carbon double bond. </p><p>In <a href="/wiki/Diels%E2%80%93Alder_reaction" title="Diels–Alder reaction">Diels–Alder reactions</a> quinones are used as dienophiles. Historically important <a href="/wiki/Total_synthesis" title="Total synthesis">syntheses</a> include <a href="/wiki/Cholesterol_total_synthesis" title="Cholesterol total synthesis">cholesterol</a>, <a href="/wiki/Cortisone" title="Cortisone">cortisone</a>, <a href="/wiki/Total_synthesis_of_morphine_and_related_alkaloids" title="Total synthesis of morphine and related alkaloids">morphine</a>, and <a href="/wiki/Reserpine" title="Reserpine">reserpine</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> <div class="mw-heading mw-heading2"><h2 id="Occurrence_and_uses">Occurrence and uses</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Quinone&action=edit&section=5" title="Edit section: Occurrence and uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Production_of_hydrogen_peroxide">Production of hydrogen peroxide</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Quinone&action=edit&section=6" title="Edit section: Production of hydrogen peroxide"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951" /><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Anthraquinone_process" title="Anthraquinone process">Anthraquinone process</a></div> <p>A large scale industrial application of quinones is for the production of <a href="/wiki/Hydrogen_peroxide" title="Hydrogen peroxide">hydrogen peroxide</a>. 2-Alkylanthraquinones are hydrogenated to the corresponding hydroquinones (quinizarins), which then transfer <span class="chemf nowrap">H<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2</sub></span></span></span> to oxygen: </p> <dl><dd>dihydroanthraquinone + <span class="chemf nowrap">O<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2</sub></span></span></span> → <a href="/wiki/Anthraquinone" title="Anthraquinone">anthraquinone</a> + <span class="chemf nowrap">H<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2</sub></span></span>O<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2</sub></span></span></span></dd></dl> <p>in this way, several million metric tons of <span class="chemf nowrap">H<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2</sub></span></span>O<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2</sub></span></span></span> are produced annually.<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> </p><p>1,4-<a href="/wiki/Naphthoquinone" title="Naphthoquinone">Naphthoquinone</a>, derived by oxidation of naphthalene with <a href="/wiki/Chromium_trioxide" title="Chromium trioxide">chromium trioxide</a>.<sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> It is the precursor to anthraquinone. </p> <div class="mw-heading mw-heading3"><h3 id="Biochemistry">Biochemistry</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Quinone&action=edit&section=7" title="Edit section: Biochemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Numerous quinones are significant roles in biology. Vitamin K, which is involved in coagulation of blood, is a quinone. <a href="/wiki/Ubiquinone" class="mw-redirect" title="Ubiquinone">Ubiquinone</a>-10 is a naturally occurring 1,4-benzoquinone involved in <a href="/wiki/Cellular_respiration" title="Cellular respiration">respiration</a> apparatus. <a href="/wiki/Plastoquinone" title="Plastoquinone">Plastoquinone</a> is a redox relay involved in photosynthesis. <a href="/wiki/Pyrroloquinoline_quinone" title="Pyrroloquinoline quinone">Pyrroloquinoline quinone</a> is another biological redox cofactor. </p> <figure class="mw-default-size mw-halign-right skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:Ubiquinone.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/04/Ubiquinone.svg/250px-Ubiquinone.svg.png" decoding="async" width="220" height="103" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/04/Ubiquinone.svg/330px-Ubiquinone.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/04/Ubiquinone.svg/440px-Ubiquinone.svg.png 2x" data-file-width="281" data-file-height="132" /></a><figcaption>Ubiquinones, as their name implies, are ubiquitous in living creatures, being components of respiratory apparatus.</figcaption></figure> <figure class="mw-default-size mw-halign-right skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:Gentisyl_quinone_isovalerate.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/50/Gentisyl_quinone_isovalerate.png/250px-Gentisyl_quinone_isovalerate.png" decoding="async" width="220" height="152" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/50/Gentisyl_quinone_isovalerate.png/330px-Gentisyl_quinone_isovalerate.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/50/Gentisyl_quinone_isovalerate.png/500px-Gentisyl_quinone_isovalerate.png 2x" data-file-width="1834" data-file-height="1268" /></a><figcaption>Blattellaquinone, a sex pheromone in cockroaches</figcaption></figure> <p>Quinones are conjectured to occur in all respiring organisms.<sup id="cite_ref-Obrien_14-0" class="reference"><a href="#cite_note-Obrien-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> Some serve as electron acceptors in electron transport chains such as those in <a href="/wiki/Photosynthesis" title="Photosynthesis">photosynthesis</a> (<a href="/wiki/Plastoquinone" title="Plastoquinone">plastoquinone</a>, <a href="/wiki/Phylloquinone" class="mw-redirect" title="Phylloquinone">phylloquinone</a>), and <a href="/wiki/Aerobic_respiration" class="mw-redirect" title="Aerobic respiration">aerobic respiration</a> (<a href="/wiki/Ubiquinone" class="mw-redirect" title="Ubiquinone">ubiquinone</a>). Phylloquinone is also known as <a href="/wiki/Vitamin_K" title="Vitamin K">vitamin K<sub>1</sub></a> as it is used by animals to carboxylate certain proteins, which are involved in <a href="/wiki/Blood_coagulation" class="mw-redirect" title="Blood coagulation">blood coagulation</a>, <a href="/wiki/Bone" title="Bone">bone</a> formation, and other processes. Conversely, the toxicity of <a href="/wiki/Paracetamol" title="Paracetamol">paracetamol</a> is due to its metabolism to a <a href="/wiki/NAPQI" title="NAPQI">quinone imine</a>, which then reacts with liver proteins to cause liver failure. </p><p>The auto-oxidation of the neurotransmitter <a href="/wiki/Dopamine" title="Dopamine">dopamine</a> and its precursor L-Dopa generates the comparatively stable dopamine quinone which inhibits the functioning of dopamine transporter (DAT) and the <a href="/wiki/Tyrosine_hydroxylase" title="Tyrosine hydroxylase">TH</a> enzyme and leads to low mitochondrial <a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate">ATP</a> production.<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>The benzoquinone <a href="/wiki/Blattellaquinone" title="Blattellaquinone">blattellaquinone</a> is a sex <a href="/wiki/Pheromone" title="Pheromone">pheromone</a> in <a href="/wiki/Cockroach" title="Cockroach">cockroaches</a>. In the spray of <a href="/wiki/Bombardier_beetle" title="Bombardier beetle">bombardier beetles</a>, hydroquinone reacts with hydrogen peroxide to produce a fiery blast of steam, a deterrent in the animal world. </p> <div class="mw-heading mw-heading3"><h3 id="Medical">Medical</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Quinone&action=edit&section=8" title="Edit section: Medical"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Several quinones are of pharmacological interest. They form a major class of anticancer cytotoxins. One example is <a href="/wiki/Daunorubicin" title="Daunorubicin">daunorubicin</a>, which is antileukemic.<sup id="cite_ref-Obrien_14-1" class="reference"><a href="#cite_note-Obrien-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> Some of them show anti-<a href="/wiki/Tumor" class="mw-redirect" title="Tumor">tumoral</a> activity. They embody some claims in <a href="/wiki/Herbal_medicine" title="Herbal medicine">herbal medicine</a>. These applications include purgative (<a href="/wiki/Sennosides" class="mw-redirect" title="Sennosides">sennosides</a>), antimicrobial and antiparasitic (<a href="/wiki/Rhein_(molecule)" title="Rhein (molecule)">rhein</a> and <a href="/w/index.php?title=Saprorthoquinone&action=edit&redlink=1" class="new" title="Saprorthoquinone (page does not exist)">saprorthoquinone</a>, <a href="/wiki/Atovaquone" title="Atovaquone">atovaquone</a>), anti-tumor (<a href="/wiki/Emodin" title="Emodin">emodin</a> and <a href="/wiki/Juglone" title="Juglone">juglone</a>), inhibition of <a href="/wiki/PGE2" class="mw-redirect" title="PGE2">PGE2</a> biosynthesis (<a href="/w/index.php?title=Arnebinone&action=edit&redlink=1" class="new" title="Arnebinone (page does not exist)">arnebinone</a> and <a href="/w/index.php?title=Arnebifuranone&action=edit&redlink=1" class="new" title="Arnebifuranone (page does not exist)">arnebifuranone</a>) and anti-<a href="/wiki/Cardiovascular_disease" title="Cardiovascular disease">cardiovascular disease</a> (<a href="/wiki/Salvia_miltiorrhiza" title="Salvia miltiorrhiza">tanshinone</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> <a href="/wiki/Malbranchea_cinnamomea" title="Malbranchea cinnamomea">Malbranchea cinnamomea</a> is a thermophilic fungus, which produces a quinone antibiotic. </p><p>Another quinone-containing drug is <a href="/w/index.php?title=Mecarbinate&action=edit&redlink=1" class="new" title="Mecarbinate (page does not exist)">Mecarbinate</a> (<a href="/w/index.php?title=Dimecarbine&action=edit&redlink=1" class="new" title="Dimecarbine (page does not exist)">dimecarbine</a>), made by the reaction of ethyl <a href="/w/index.php?title=N-methyl-%CE%B2-aminocrotonate&action=edit&redlink=1" class="new" title="N-methyl-β-aminocrotonate (page does not exist)">N-methyl-β-aminocrotonate</a> with para-benzoquinone. Others include <a href="/w/index.php?title=Amendol&action=edit&redlink=1" class="new" title="Amendol (page does not exist)">Amendol</a>, <a href="/w/index.php?title=Oxyphemedol&action=edit&redlink=1" class="new" title="Oxyphemedol (page does not exist)">Oxyphemedol</a>, <a href="/w/index.php?title=Phemedol&action=edit&redlink=1" class="new" title="Phemedol (page does not exist)">Phemedol</a> all in FR5142 (M) ― 1967-06-05.<sup class="noprint Inline-Template" style="margin-left:0.1em; white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Please_clarify" title="Wikipedia:Please clarify"><span title="The text near this tag may need clarification or removal of jargon. (July 2018)">clarification needed</span></a></i>]</sup> Note: These are all indoles made via the <a href="/wiki/Nenitzescu_indole_synthesis" title="Nenitzescu indole synthesis">Nenitzescu indole synthesis</a>. The antineoplastic <a href="/wiki/Apaziquone" title="Apaziquone">Apaziquone</a>. </p><p>Benzoquinone compounds are a metabolite of <a href="/wiki/Paracetamol" title="Paracetamol">paracetamol</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> </p> <div class="mw-heading mw-heading3"><h3 id="Dyes">Dyes</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Quinone&action=edit&section=9" title="Edit section: Dyes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Many natural and artificial coloring substances (<a href="/wiki/Dye" title="Dye">dyes</a> and <a href="/wiki/Pigment" title="Pigment">pigments</a>) are quinone derivatives, for instance <a href="/wiki/Lawsone" title="Lawsone">lawsone</a> is the active dye compound in <a href="/wiki/Henna" title="Henna">henna</a>. They are second only to <a href="/wiki/Azo_dyes" class="mw-redirect" title="Azo dyes">azo dyes</a> in importance as dyestuffs, with particular emphasis on blue colors. <a href="/wiki/Alizarin" title="Alizarin">Alizarin</a> (1,2-dihydroxy-9,10-anthraquinone), extracted from the <a href="/wiki/Rubia" title="Rubia">madder</a> plant, was the first natural dye to be synthesized from coal tar. </p> <div class="mw-heading mw-heading3"><h3 id="Photography">Photography</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Quinone&action=edit&section=10" title="Edit section: Photography"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>A commercial application of quinones is in <a href="/wiki/Monochrome_photography" title="Monochrome photography">black-and-white photography</a>. Black-and-white film is covered with an emulsion containing silver bromide or silver iodide crystals, which exposure to light activates. Hydroquinone is used to reduce the activated silver ions to metallic silver. During this process, hydroquinone is oxidized to quinone. All silver halide not activated by light or reduced by hydroquinone is removed, leaving a negative by deposited silver where the film had been struck by light.<sup id="cite_ref-18" class="reference"><a href="#cite_note-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Nomenclature">Nomenclature</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Quinone&action=edit&section=11" title="Edit section: Nomenclature"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Quinones are commonly named with a prefix that indicates the parent aromatic hydrocarbon ("benzo-" for benzene, "naphtho-" for naphthalene, "anthra-" for <a href="/wiki/Anthracene" title="Anthracene">anthracene</a>, etc.) and the "-quinone" suffix. Infix multipliers "-di-", "-tri-", "-tetra-" (etc.) are used when there are 4, 6, 8 (etc.) carbonyls. The position of the carbonyl groups can be indicated before the prefix (as in "1,4,5,8-naphthodiquinone") or after it ("anthra-1,4-quinone"). </p> <div class="mw-heading mw-heading2"><h2 id="Structural_analogues_of_quinones">Structural analogues of quinones</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Quinone&action=edit&section=12" title="Edit section: Structural analogues of quinones"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Quinone_methide" title="Quinone methide">Quinone methide</a> –  where one O is replaced by C</li> <li><a href="/wiki/Xylylene" title="Xylylene">Xylylene</a> –  where both O's are replaced by C's</li> <li>Quinone imine –  where one O is replaced by N, illustrated by <a href="/wiki/NAPQI" title="NAPQI">NAPQI</a></li> <li>Quinone diimine –  where both O's are replaced by N's, illustrated by the antiseptic <a href="/wiki/Ambazone" title="Ambazone">ambazone</a></li> <li>Azaxylylene –  where both O's are replaced by one N and one C, illustrated by various fuchsine dyes like <a href="/wiki/Pararosaniline" title="Pararosaniline">pararosaniline</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=Quinone&action=edit&section=13" 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-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text"><a href="/wiki/International_Union_of_Pure_and_Applied_Chemistry" title="International Union of Pure and Applied Chemistry">IUPAC</a>, <i><a href="/wiki/IUPAC_books#Gold_Book" class="mw-redirect" title="IUPAC books">Compendium of Chemical Terminology</a></i>, 2nd ed. (the "Gold Book") (1997). 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<div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Quinone&action=edit&section=14" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a rel="nofollow" class="external text" href="https://meshb.nlm.nih.gov/record/ui?name=Quinones">Quinones</a> at the U.S. National Library of Medicine <a href="/wiki/Medical_Subject_Headings" title="Medical Subject Headings">Medical Subject Headings</a> (MeSH)</li></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 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