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</a> <ul id="toc-History-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Production" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Production"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Production</span> </div> </a> <button aria-controls="toc-Production-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Production subsection</span> </button> <ul id="toc-Production-sublist" class="vector-toc-list"> <li id="toc-Current_method" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Current_method"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.1</span> <span>Current method</span> </div> </a> <ul id="toc-Current_method-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Older_methods" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Older_methods"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.2</span> <span>Older methods</span> </div> </a> <ul id="toc-Older_methods-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Chemical_properties" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Chemical_properties"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Chemical properties</span> </div> </a> <button aria-controls="toc-Chemical_properties-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 Chemical properties subsection</span> </button> <ul id="toc-Chemical_properties-sublist" class="vector-toc-list"> <li id="toc-Polymerisation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Polymerisation"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.1</span> <span>Polymerisation</span> </div> </a> <ul id="toc-Polymerisation-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Natural_occurrence" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Natural_occurrence"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Natural occurrence</span> </div> </a> <button aria-controls="toc-Natural_occurrence-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 Natural occurrence subsection</span> </button> <ul id="toc-Natural_occurrence-sublist" class="vector-toc-list"> <li id="toc-Metabolism" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Metabolism"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1</span> <span>Metabolism</span> </div> </a> <ul id="toc-Metabolism-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Uses" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Uses"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Uses</span> </div> </a> <button aria-controls="toc-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 Uses subsection</span> </button> <ul id="toc-Uses-sublist" class="vector-toc-list"> <li id="toc-Chemical_intermediate" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Chemical_intermediate"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.1</span> <span>Chemical intermediate</span> </div> </a> <ul id="toc-Chemical_intermediate-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Solvent" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Solvent"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.2</span> <span>Solvent</span> </div> </a> <ul id="toc-Solvent-sublist" class="vector-toc-list"> <li id="toc-Lab_and_domestic_solvent" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Lab_and_domestic_solvent"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.2.1</span> <span>Lab and domestic solvent</span> </div> </a> <ul id="toc-Lab_and_domestic_solvent-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Biology" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Biology"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.2.2</span> <span>Biology</span> </div> </a> <ul id="toc-Biology-sublist" class="vector-toc-list"> </ul> </li> </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">6.3</span> <span>Medical</span> </div> </a> <ul id="toc-Medical-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Safety" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Safety"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Safety</span> </div> </a> <button aria-controls="toc-Safety-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 Safety subsection</span> </button> <ul id="toc-Safety-sublist" class="vector-toc-list"> <li id="toc-Toxicity" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Toxicity"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.1</span> <span>Toxicity</span> </div> </a> <ul id="toc-Toxicity-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Environmental_effects" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Environmental_effects"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.2</span> <span>Environmental effects</span> </div> </a> <ul id="toc-Environmental_effects-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-EPA_classification" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#EPA_classification"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.3</span> <span>EPA classification</span> </div> </a> <ul id="toc-EPA_classification-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Extraterrestrial_occurrence" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Extraterrestrial_occurrence"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>Extraterrestrial occurrence</span> </div> </a> <ul id="toc-Extraterrestrial_occurrence-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>References</span> </div> </a> <button aria-controls="toc-References-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 References subsection</span> </button> <ul id="toc-References-sublist" class="vector-toc-list"> <li id="toc-Common_sources" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Common_sources"> <div class="vector-toc-text"> <span class="vector-toc-numb">9.1</span> <span>Common sources</span> </div> </a> <ul id="toc-Common_sources-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Further_reading" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Further_reading"> <div class="vector-toc-text"> <span class="vector-toc-numb">9.2</span> <span>Further reading</span> </div> </a> <ul id="toc-Further_reading-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span class="vector-dropdown-label-text">Toggle the table of contents</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Acetone</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 73 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-73" 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">73 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-af mw-list-item"><a href="https://af.wikipedia.org/wiki/Asetoon" title="Asetoon – Afrikaans" lang="af" hreflang="af" data-title="Asetoon" data-language-autonym="Afrikaans" data-language-local-name="Afrikaans" class="interlanguage-link-target"><span>Afrikaans</span></a></li><li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%A3%D8%B3%D9%8A%D8%AA%D9%88%D9%86" title="أسيتون – Arabic" lang="ar" hreflang="ar" data-title="أسيتون" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-ast mw-list-item"><a href="https://ast.wikipedia.org/wiki/Acetona" title="Acetona – Asturian" lang="ast" hreflang="ast" data-title="Acetona" data-language-autonym="Asturianu" data-language-local-name="Asturian" class="interlanguage-link-target"><span>Asturianu</span></a></li><li class="interlanguage-link interwiki-az mw-list-item"><a href="https://az.wikipedia.org/wiki/Aseton" title="Aseton – Azerbaijani" lang="az" hreflang="az" data-title="Aseton" data-language-autonym="Azərbaycanca" data-language-local-name="Azerbaijani" class="interlanguage-link-target"><span>Azərbaycanca</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D8%A7%D8%B3%D8%AA%D9%88%D9%86" title="استون – South Azerbaijani" lang="azb" hreflang="azb" data-title="استون" 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%85%E0%A7%8D%E0%A6%AF%E0%A6%BE%E0%A6%B8%E0%A6%BF%E0%A6%9F%E0%A7%8B%E0%A6%A8" title="অ্যাসিটোন – Bangla" lang="bn" hreflang="bn" data-title="অ্যাসিটোন" data-language-autonym="বাংলা" data-language-local-name="Bangla" class="interlanguage-link-target"><span>বাংলা</span></a></li><li class="interlanguage-link interwiki-be mw-list-item"><a href="https://be.wikipedia.org/wiki/%D0%90%D1%86%D1%8D%D1%82%D0%BE%D0%BD" title="Ацэтон – Belarusian" lang="be" hreflang="be" data-title="Ацэтон" data-language-autonym="Беларуская" data-language-local-name="Belarusian" class="interlanguage-link-target"><span>Беларуская</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%90%D1%86%D0%B5%D1%82%D0%BE%D0%BD" title="Ацетон – Bulgarian" lang="bg" hreflang="bg" data-title="Ацетон" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target"><span>Български</span></a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Aceton" title="Aceton – Bosnian" lang="bs" hreflang="bs" data-title="Aceton" data-language-autonym="Bosanski" data-language-local-name="Bosnian" class="interlanguage-link-target"><span>Bosanski</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Acetona" title="Acetona – Catalan" lang="ca" hreflang="ca" data-title="Acetona" 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/Aceton" title="Aceton – Czech" lang="cs" hreflang="cs" data-title="Aceton" 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/Acetone" title="Acetone – Danish" lang="da" hreflang="da" data-title="Acetone" 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/Aceton" title="Aceton – German" lang="de" hreflang="de" data-title="Aceton" 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/Atsetoon" title="Atsetoon – Estonian" lang="et" hreflang="et" data-title="Atsetoon" 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%91%CE%BA%CE%B5%CF%84%CF%8C%CE%BD%CE%B7" title="Ακετόνη – Greek" lang="el" hreflang="el" data-title="Ακετόνη" 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/Acetona" title="Acetona – Spanish" lang="es" hreflang="es" data-title="Acetona" 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/Acetono" title="Acetono – Esperanto" lang="eo" hreflang="eo" data-title="Acetono" 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/Azetona" title="Azetona – Basque" lang="eu" hreflang="eu" data-title="Azetona" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%A7%D8%B3%D8%AA%D9%88%D9%86" title="استون – Persian" lang="fa" hreflang="fa" data-title="استون" 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/Ac%C3%A9tone" title="Acétone – French" lang="fr" hreflang="fr" data-title="Acétone" 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/Aic%C3%A9at%C3%B3n" title="Aicéatón – Irish" lang="ga" hreflang="ga" data-title="Aicéatón" 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/Acetona" title="Acetona – Galician" lang="gl" hreflang="gl" data-title="Acetona" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EC%95%84%EC%84%B8%ED%86%A4" title="아세톤 – Korean" lang="ko" hreflang="ko" data-title="아세톤" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D4%B1%D6%81%D5%A5%D5%BF%D5%B8%D5%B6" title="Ացետոն – Armenian" lang="hy" hreflang="hy" data-title="Ացետոն" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-hi mw-list-item"><a href="https://hi.wikipedia.org/wiki/%E0%A4%8F%E0%A4%B8%E0%A5%80%E0%A4%9F%E0%A5%8B%E0%A4%A8" title="एसीटोन – Hindi" lang="hi" hreflang="hi" data-title="एसीटोन" 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/Aceton" title="Aceton – Croatian" lang="hr" hreflang="hr" data-title="Aceton" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-io mw-list-item"><a href="https://io.wikipedia.org/wiki/Acetono" title="Acetono – Ido" lang="io" hreflang="io" data-title="Acetono" data-language-autonym="Ido" data-language-local-name="Ido" class="interlanguage-link-target"><span>Ido</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Aseton" title="Aseton – Indonesian" lang="id" hreflang="id" data-title="Aseton" 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/Acetone" title="Acetone – Italian" lang="it" hreflang="it" data-title="Acetone" 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%90%D7%A6%D7%98%D7%95%D7%9F" title="אצטון – Hebrew" lang="he" hreflang="he" data-title="אצטון" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-kn mw-list-item"><a href="https://kn.wikipedia.org/wiki/%E0%B2%85%E0%B2%B8%E0%B2%BF%E0%B2%9F%E0%B3%8B%E0%B2%A8%E0%B3%8D" title="ಅಸಿಟೋನ್ – Kannada" lang="kn" hreflang="kn" data-title="ಅಸಿಟೋನ್" data-language-autonym="ಕನ್ನಡ" data-language-local-name="Kannada" class="interlanguage-link-target"><span>ಕನ್ನಡ</span></a></li><li class="interlanguage-link interwiki-ka mw-list-item"><a href="https://ka.wikipedia.org/wiki/%E1%83%90%E1%83%AA%E1%83%94%E1%83%A2%E1%83%9D%E1%83%9C%E1%83%98" title="აცეტონი – Georgian" lang="ka" hreflang="ka" data-title="აცეტონი" data-language-autonym="ქართული" data-language-local-name="Georgian" class="interlanguage-link-target"><span>ქართული</span></a></li><li class="interlanguage-link interwiki-kk mw-list-item"><a href="https://kk.wikipedia.org/wiki/%D0%90%D1%86%D0%B5%D1%82%D0%BE%D0%BD" title="Ацетон – Kazakh" lang="kk" hreflang="kk" data-title="Ацетон" data-language-autonym="Қазақша" data-language-local-name="Kazakh" class="interlanguage-link-target"><span>Қазақша</span></a></li><li class="interlanguage-link interwiki-sw mw-list-item"><a href="https://sw.wikipedia.org/wiki/Asetoni" title="Asetoni – Swahili" lang="sw" hreflang="sw" data-title="Asetoni" data-language-autonym="Kiswahili" data-language-local-name="Swahili" class="interlanguage-link-target"><span>Kiswahili</span></a></li><li class="interlanguage-link interwiki-ku mw-list-item"><a href="https://ku.wikipedia.org/wiki/Aseton" title="Aseton – Kurdish" lang="ku" hreflang="ku" data-title="Aseton" data-language-autonym="Kurdî" data-language-local-name="Kurdish" class="interlanguage-link-target"><span>Kurdî</span></a></li><li class="interlanguage-link interwiki-ky mw-list-item"><a href="https://ky.wikipedia.org/wiki/%D0%90%D1%86%D0%B5%D1%82%D0%BE%D0%BD" title="Ацетон – Kyrgyz" lang="ky" hreflang="ky" data-title="Ацетон" data-language-autonym="Кыргызча" data-language-local-name="Kyrgyz" class="interlanguage-link-target"><span>Кыргызча</span></a></li><li class="interlanguage-link interwiki-la mw-list-item"><a href="https://la.wikipedia.org/wiki/Acetone" title="Acetone – Latin" lang="la" hreflang="la" data-title="Acetone" data-language-autonym="Latina" data-language-local-name="Latin" class="interlanguage-link-target"><span>Latina</span></a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Acetons" title="Acetons – Latvian" lang="lv" hreflang="lv" data-title="Acetons" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target"><span>Latviešu</span></a></li><li class="interlanguage-link interwiki-lt mw-list-item"><a href="https://lt.wikipedia.org/wiki/Acetonas" title="Acetonas – Lithuanian" lang="lt" hreflang="lt" data-title="Acetonas" data-language-autonym="Lietuvių" data-language-local-name="Lithuanian" class="interlanguage-link-target"><span>Lietuvių</span></a></li><li class="interlanguage-link interwiki-li mw-list-item"><a href="https://li.wikipedia.org/wiki/Aceton" title="Aceton – Limburgish" lang="li" hreflang="li" data-title="Aceton" data-language-autonym="Limburgs" data-language-local-name="Limburgish" class="interlanguage-link-target"><span>Limburgs</span></a></li><li class="interlanguage-link interwiki-lmo mw-list-item"><a href="https://lmo.wikipedia.org/wiki/Acetun" title="Acetun – Lombard" lang="lmo" hreflang="lmo" data-title="Acetun" data-language-autonym="Lombard" data-language-local-name="Lombard" class="interlanguage-link-target"><span>Lombard</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Aceton" title="Aceton – Hungarian" lang="hu" hreflang="hu" data-title="Aceton" 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%90%D1%86%D0%B5%D1%82%D0%BE%D0%BD" title="Ацетон – Macedonian" lang="mk" hreflang="mk" data-title="Ацетон" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-ml mw-list-item"><a href="https://ml.wikipedia.org/wiki/%E0%B4%85%E0%B4%B8%E0%B5%86%E0%B4%B1%E0%B5%8D%E0%B4%B1%E0%B5%8B%E0%B5%BA" title="അസെറ്റോൺ – Malayalam" lang="ml" hreflang="ml" data-title="അസെറ്റോൺ" data-language-autonym="മലയാളം" data-language-local-name="Malayalam" class="interlanguage-link-target"><span>മലയാളം</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Aseton" title="Aseton – Malay" lang="ms" hreflang="ms" data-title="Aseton" 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/Aceton" title="Aceton – Dutch" lang="nl" hreflang="nl" data-title="Aceton" 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%A2%E3%82%BB%E3%83%88%E3%83%B3" title="アセトン – Japanese" lang="ja" hreflang="ja" data-title="アセトン" 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/Aceton" title="Aceton – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Aceton" data-language-autonym="Norsk bokmål" data-language-local-name="Norwegian Bokmål" class="interlanguage-link-target"><span>Norsk bokmål</span></a></li><li class="interlanguage-link interwiki-nn mw-list-item"><a href="https://nn.wikipedia.org/wiki/Aceton" title="Aceton – Norwegian Nynorsk" lang="nn" hreflang="nn" data-title="Aceton" data-language-autonym="Norsk nynorsk" data-language-local-name="Norwegian Nynorsk" class="interlanguage-link-target"><span>Norsk nynorsk</span></a></li><li class="interlanguage-link interwiki-uz mw-list-item"><a href="https://uz.wikipedia.org/wiki/Atseton" title="Atseton – Uzbek" lang="uz" hreflang="uz" data-title="Atseton" data-language-autonym="Oʻzbekcha / ўзбекча" data-language-local-name="Uzbek" class="interlanguage-link-target"><span>Oʻzbekcha / ўзбекча</span></a></li><li class="interlanguage-link interwiki-pnb mw-list-item"><a href="https://pnb.wikipedia.org/wiki/%D8%A7%DB%8C%D8%B3%D9%B9%D9%88%D9%86" title="ایسٹون – Western Punjabi" lang="pnb" hreflang="pnb" data-title="ایسٹون" data-language-autonym="پنجابی" data-language-local-name="Western Punjabi" class="interlanguage-link-target"><span>پنجابی</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Aceton" title="Aceton – Polish" lang="pl" hreflang="pl" data-title="Aceton" 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/Acetona" title="Acetona – Portuguese" lang="pt" hreflang="pt" data-title="Acetona" 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/Aceton%C4%83" title="Acetonă – Romanian" lang="ro" hreflang="ro" data-title="Acetonă" 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%90%D1%86%D0%B5%D1%82%D0%BE%D0%BD" title="Ацетон – Russian" lang="ru" hreflang="ru" data-title="Ацетон" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sq mw-list-item"><a href="https://sq.wikipedia.org/wiki/Acetoni" title="Acetoni – Albanian" lang="sq" hreflang="sq" data-title="Acetoni" data-language-autonym="Shqip" data-language-local-name="Albanian" class="interlanguage-link-target"><span>Shqip</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Acetone" title="Acetone – Simple English" lang="en-simple" hreflang="en-simple" data-title="Acetone" data-language-autonym="Simple English" data-language-local-name="Simple English" class="interlanguage-link-target"><span>Simple English</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Acet%C3%B3n" title="Acetón – Slovak" lang="sk" hreflang="sk" data-title="Acetón" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Aceton" title="Aceton – Slovenian" lang="sl" hreflang="sl" data-title="Aceton" 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/Aceton" title="Aceton – Serbian" lang="sr" hreflang="sr" data-title="Aceton" 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/Aceton" title="Aceton – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Aceton" 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/Asetoni" title="Asetoni – Finnish" lang="fi" hreflang="fi" data-title="Asetoni" 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/Aceton" title="Aceton – Swedish" lang="sv" hreflang="sv" data-title="Aceton" 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%85%E0%AE%9A%E0%AE%BF%E0%AE%9F%E0%AF%8D%E0%AE%9F%E0%AF%8B%E0%AE%A9%E0%AF%8D" title="அசிட்டோன் – Tamil" lang="ta" hreflang="ta" data-title="அசிட்டோன்" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B9%81%E0%B8%AD%E0%B8%8B%E0%B8%B5%E0%B9%82%E0%B8%97%E0%B8%99" title="แอซีโทน – Thai" lang="th" hreflang="th" data-title="แอซีโทน" data-language-autonym="ไทย" data-language-local-name="Thai" class="interlanguage-link-target"><span>ไทย</span></a></li><li class="interlanguage-link interwiki-tg mw-list-item"><a href="https://tg.wikipedia.org/wiki/%D0%90%D1%82%D1%81%D0%B5%D1%82%D0%BE%D0%BD" title="Атсетон – Tajik" lang="tg" hreflang="tg" data-title="Атсетон" data-language-autonym="Тоҷикӣ" data-language-local-name="Tajik" class="interlanguage-link-target"><span>Тоҷикӣ</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Aseton" title="Aseton – Turkish" lang="tr" hreflang="tr" data-title="Aseton" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-uk badge-Q17437798 badge-goodarticle mw-list-item" title="good article badge"><a href="https://uk.wikipedia.org/wiki/%D0%90%D1%86%D0%B5%D1%82%D0%BE%D0%BD" title="Ацетон – Ukrainian" lang="uk" hreflang="uk" data-title="Ацетон" 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/Aceton" title="Aceton – Vietnamese" lang="vi" hreflang="vi" data-title="Aceton" 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-war mw-list-item"><a href="https://war.wikipedia.org/wiki/Aseton" title="Aseton – Waray" lang="war" hreflang="war" data-title="Aseton" data-language-autonym="Winaray" data-language-local-name="Waray" class="interlanguage-link-target"><span>Winaray</span></a></li><li class="interlanguage-link interwiki-wuu mw-list-item"><a href="https://wuu.wikipedia.org/wiki/%E4%B8%99%E9%85%AE" title="丙酮 – Wu" lang="wuu" hreflang="wuu" data-title="丙酮" data-language-autonym="吴语" data-language-local-name="Wu" class="interlanguage-link-target"><span>吴语</span></a></li><li class="interlanguage-link interwiki-zh-yue mw-list-item"><a href="https://zh-yue.wikipedia.org/wiki/%E4%B8%99%E9%85%AE" title="丙酮 – Cantonese" lang="yue" hreflang="yue" data-title="丙酮" data-language-autonym="粵語" data-language-local-name="Cantonese" class="interlanguage-link-target"><span>粵語</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E4%B8%99%E9%85%AE" title="丙酮 – Chinese" lang="zh" hreflang="zh" data-title="丙酮" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target"><span>中文</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span class="wb-langlinks-edit wb-langlinks-link"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q49546#sitelinks-wikipedia" title="Edit interlanguage links" class="wbc-editpage">Edit links</a></span></div> </div> </div> </div> </header> <div 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class="vector-column-end"> <div class="vector-sticky-pinned-container"> <nav class="vector-page-tools-landmark" aria-label="Page tools"> <div id="vector-page-tools-pinned-container" class="vector-pinned-container"> </div> </nav> <nav class="vector-appearance-landmark" aria-label="Appearance"> <div id="vector-appearance-pinned-container" class="vector-pinned-container"> <div id="vector-appearance" class="vector-appearance vector-pinnable-element"> <div class="vector-pinnable-header vector-appearance-pinnable-header vector-pinnable-header-pinned" data-feature-name="appearance-pinned" data-pinnable-element-id="vector-appearance" data-pinned-container-id="vector-appearance-pinned-container" 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">Organic compound ((CH3)2CO); simplest ketone</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/Acetoin" title="Acetoin">Acetoin</a>.</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">For the musical instrument company, see <a href="/wiki/Ace_Tone" title="Ace Tone">Ace Tone</a>.</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">For other uses, see <a href="/wiki/Acetone_(disambiguation)" class="mw-disambig" title="Acetone (disambiguation)">Acetone (disambiguation)</a>.</div> <style data-mw-deduplicate="TemplateStyles:r1084375498">.mw-parser-output .ib-chembox{border-collapse:collapse;text-align:left}.mw-parser-output .ib-chembox td,.mw-parser-output .ib-chembox th{border:1px solid #a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}</style> <table class="infobox ib-chembox"> <caption>Acetone<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> </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" typeof="mw:File"><a href="/wiki/File:Acetone-CRC-MW-ED-dimensions-2D-Vector.svg" class="mw-file-description" title="Full structural formula of acetone with dimensions"><img alt="Full structural formula of acetone with dimensions" src="//upload.wikimedia.org/wikipedia/commons/thumb/9/97/Acetone-CRC-MW-ED-dimensions-2D-Vector.svg/136px-Acetone-CRC-MW-ED-dimensions-2D-Vector.svg.png" decoding="async" width="136" height="84" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/97/Acetone-CRC-MW-ED-dimensions-2D-Vector.svg/204px-Acetone-CRC-MW-ED-dimensions-2D-Vector.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/97/Acetone-CRC-MW-ED-dimensions-2D-Vector.svg/272px-Acetone-CRC-MW-ED-dimensions-2D-Vector.svg.png 2x" data-file-width="500" data-file-height="310" /></a><figcaption>Full structural formula of acetone with dimensions</figcaption></figure> </td> <td style="width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Acetone-2D-skeletal.svg" class="mw-file-description" title="Skeletal formula of acetone"><img alt="Skeletal formula of acetone" src="//upload.wikimedia.org/wikipedia/commons/thumb/f/fb/Acetone-2D-skeletal.svg/130px-Acetone-2D-skeletal.svg.png" decoding="async" width="130" height="127" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/fb/Acetone-2D-skeletal.svg/195px-Acetone-2D-skeletal.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/fb/Acetone-2D-skeletal.svg/260px-Acetone-2D-skeletal.svg.png 2x" data-file-width="167" data-file-height="163" /></a><figcaption>Skeletal formula of acetone</figcaption></figure> </td></tr></tbody></table> </td></tr> <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" typeof="mw:File"><a href="/wiki/File:Acetone-3D-balls.png" class="mw-file-description" title="Ball-and-stick model of acetone"><img alt="Ball-and-stick model of acetone" src="//upload.wikimedia.org/wikipedia/commons/thumb/8/8d/Acetone-3D-balls.png/131px-Acetone-3D-balls.png" decoding="async" width="131" height="102" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/8d/Acetone-3D-balls.png/197px-Acetone-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/8d/Acetone-3D-balls.png/262px-Acetone-3D-balls.png 2x" data-file-width="1100" data-file-height="860" /></a><figcaption>Ball-and-stick model of acetone</figcaption></figure> </td> <td style="width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Acetone-3D-vdW.png" class="mw-file-description" title="Space-filling model of acetone"><img alt="Space-filling model of acetone" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/ec/Acetone-3D-vdW.png/106px-Acetone-3D-vdW.png" decoding="async" width="106" height="92" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/ec/Acetone-3D-vdW.png/159px-Acetone-3D-vdW.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/ec/Acetone-3D-vdW.png/212px-Acetone-3D-vdW.png 2x" data-file-width="1100" data-file-height="958" /></a><figcaption>Space-filling model of acetone</figcaption></figure> </td></tr></tbody></table> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Sample_of_Acetone.jpg" class="mw-file-description" title="Sample of acetone"><img alt="Sample of acetone" src="//upload.wikimedia.org/wikipedia/commons/thumb/4/41/Sample_of_Acetone.jpg/220px-Sample_of_Acetone.jpg" decoding="async" width="220" height="314" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/41/Sample_of_Acetone.jpg/330px-Sample_of_Acetone.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/41/Sample_of_Acetone.jpg/440px-Sample_of_Acetone.jpg 2x" data-file-width="2110" data-file-height="3010" /></a></span> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Chemical_nomenclature" title="Chemical nomenclature">IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">Acetone<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></div> </td></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;">Propan-2-one<sup id="cite_ref-iupac2013_8-0" class="reference"><a href="#cite_note-iupac2013-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup></div></div> </td></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Chemical_nomenclature#Systematic_name" title="Chemical nomenclature">Systematic IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;">2-Propanone</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;"><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>Acetonum (<style data-mw-deduplicate="TemplateStyles:r1177148991">.mw-parser-output .IPA-label-small{font-size:85%}.mw-parser-output .references .IPA-label-small,.mw-parser-output .infobox .IPA-label-small,.mw-parser-output .navbox .IPA-label-small{font-size:100%}</style><span class="IPA-label IPA-label-small">Latin pronunciation:</span> <span class="IPA nowrap" lang="la-Latn-fonipa"><a href="/wiki/Help:IPA/Latin" title="Help:IPA/Latin">[aˈkeːtonum]</a></span>)</li> <li>Dimethyl ketone<sup id="cite_ref-nist_2-0" class="reference"><a href="#cite_note-nist-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup></li> <li>Dimethyl <a href="/wiki/Carbonyl" class="mw-redirect" title="Carbonyl">carbonyl</a></li> <li>Ketone propane<sup id="cite_ref-NIOSH_3-0" class="reference"><a href="#cite_note-NIOSH-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup></li> <li>β-Ketopropane<sup id="cite_ref-nist_2-1" class="reference"><a href="#cite_note-nist-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup></li> <li>Propanone<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></li> <li>2-Propanone<sup id="cite_ref-nist_2-2" class="reference"><a href="#cite_note-nist-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup></li> <li>Pyroacetic spirit (archaic)<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></li> <li>Spirit of Saturn (archaic)<sup id="cite_ref-gorman1962_6-0" class="reference"><a href="#cite_note-gorman1962-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup></li></ul> </div></div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=67-64-1">67-64-1</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=CC%28%3DO%29C">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td>3DMet </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.3dmet.dna.affrc.go.jp"><a rel="nofollow" class="external text" href="http://www.3dmet.dna.affrc.go.jp/cgi/show_data.php?acc=B00058">B00058</a></span></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Beilstein_database" title="Beilstein database">Beilstein Reference</a></div> </td> <td>635680 </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=15347">CHEBI:15347</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/ChEMBL14253">ChEMBL14253</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.175.html">175</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a> </td> <td><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.000.602">100.000.602</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q49546#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span> </td></tr> <tr> <td><a href="/wiki/European_Community_number" title="European Community number"><span title="European Community number (chemical identifier)">EC Number</span></a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>200-662-2</li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Gmelin_database" title="Gmelin database">Gmelin Reference</a></div> </td> <td>1466 </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/D02311">D02311</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/Medical_Subject_Headings" title="Medical Subject Headings">MeSH</a> </td> <td><span title="www.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://www.nlm.nih.gov/cgi/mesh/2014/MB_cgi?mode=&term=Acetone">Acetone</a></span> </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/180">180</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/RTECS" class="mw-redirect" title="RTECS">RTECS number</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>AL3150000</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/1364PS73AF">1364PS73AF</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/UN_number" title="UN number">UN number</a> </td> <td>1090 </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/DTXSID8021482">DTXSID8021482</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q49546#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></span></li></ul></div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/C3H6O/c1-3(2)4/h1-2H3<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: CSCPPACGZOOCGX-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><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=1/C3H6O/c1-3(2)4/h1-2H3</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: CSCPPACGZOOCGX-UHFFFAOYAF</div></div></li></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">CC(=O)C</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td><span title="Carbon">C</span><sub>3</sub><span title="Hydrogen">H</span><sub>6</sub><span title="Oxygen">O</span> </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td><span class="nowrap"><span data-sort-value="7001580800000000000♠"></span>58.080</span> g·mol<sup>−1</sup>   </td></tr> <tr> <td>Appearance </td> <td>Colourless liquid </td></tr> <tr> <td><a href="/wiki/Odor" title="Odor">Odor</a> </td> <td>Pungent, fruity<sup id="cite_ref-smell_9-0" class="reference"><a href="#cite_note-smell-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Density" title="Density">Density</a> </td> <td>0.7845 g/cm<sup>3</sup> (25 °C)<sup id="cite_ref-h1_10-0" class="reference"><a href="#cite_note-h1-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>−94.9 °C (−138.8 °F; 178.2 K)<sup id="cite_ref-h1_10-4" class="reference"><a href="#cite_note-h1-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Boiling_point" title="Boiling point">Boiling point</a> </td> <td>56.08 °C (132.94 °F; 329.23 K)<sup id="cite_ref-h1_10-5" class="reference"><a href="#cite_note-h1-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </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>Miscible<sup id="cite_ref-h1_10-1" class="reference"><a href="#cite_note-h1-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Solubility" title="Solubility">Solubility</a> </td> <td>Miscible in <a href="/wiki/Benzene" title="Benzene">benzene</a>, <a href="/wiki/Diethyl_ether" title="Diethyl ether">diethyl ether</a>, <a href="/wiki/Methanol" title="Methanol">methanol</a>, <a href="/wiki/Chloroform" title="Chloroform">chloroform</a>, <a href="/wiki/Ethanol" title="Ethanol">ethanol</a><sup id="cite_ref-h1_10-2" class="reference"><a href="#cite_note-h1-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Partition_coefficient" title="Partition coefficient">log <i>P</i></a> </td> <td>−0.24<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> </td></tr> <tr> <td><a href="/wiki/Vapor_pressure" title="Vapor pressure">Vapor pressure</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>9.39<span class="nowrap"> </span>kPa (0 °C)</li><li>30.6<span class="nowrap"> </span>kPa (25 °C)</li><li>374<span class="nowrap"> </span>kPa (100 °C)</li><li>2.8<span class="nowrap"> </span>MPa (200 °C)<sup id="cite_ref-nist_2-3" class="reference"><a href="#cite_note-nist-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/Acid_dissociation_constant" title="Acid dissociation constant">Acidity</a> (p<i>K</i><sub>a</sub>) </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>19.16 (H<sub>2</sub>O)<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></li><li>26.5 (DMSO)<sup id="cite_ref-Bordwell_13-0" class="reference"><a href="#cite_note-Bordwell-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Magnetic_susceptibility" title="Magnetic susceptibility">Magnetic susceptibility</a> (χ)</div> </td> <td>−33.8·10<sup>−6</sup> cm<sup>3</sup>/mol<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> </td></tr> <tr> <td><a href="/wiki/Thermal_conductivity" class="mw-redirect" title="Thermal conductivity">Thermal conductivity</a> </td> <td>0.161<span class="nowrap"> </span>W/(m·K) (25 °C)<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> </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>1.3588 (20 °C)<sup id="cite_ref-h1_10-3" class="reference"><a href="#cite_note-h1-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Viscosity" title="Viscosity">Viscosity</a> </td> <td>0.306<span class="nowrap"> </span>mPa·s (25 °C)<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> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Structure </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Coordination_geometry" title="Coordination geometry">Coordination geometry</a></div> </td> <td><a href="/wiki/Trigonal_planar" class="mw-redirect" title="Trigonal planar">Trigonal planar</a> at C2 </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Molecular_geometry" title="Molecular geometry">Molecular shape</a></div> </td> <td>Dihedral at C2 </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Dipole#Molecular_dipoles" title="Dipole">Dipole moment</a></div> </td> <td>2.88 D<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> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Thermochemistry<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> </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Heat_capacity" title="Heat capacity">Heat capacity</a> <span style="font-size:112%;">(<i>C</i>)</span></div> </td> <td>126.3<span class="nowrap"> </span>J/(mol·K) </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Standard_molar_entropy" title="Standard molar entropy">Std molar<br />entropy</a> <span style="font-size:112%;">(<i>S</i><sup>⦵</sup><sub>298</sub>)</span></div> </td> <td>199.8<span class="nowrap"> </span>J/(mol·K) </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Standard_enthalpy_change_of_formation" class="mw-redirect" title="Standard enthalpy change of formation">Std enthalpy of<br />formation</a> <span style="font-size:112%;">(Δ<sub>f</sub><i>H</i><sup>⦵</sup><sub>298</sub>)</span></div> </td> <td>−248.4<span class="nowrap"> </span>kJ/mol </td></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>−1.79<span class="nowrap"> </span>MJ/mol </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Hazards </th></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;"><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>Highly flammable </td></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;"><a href="/wiki/Globally_Harmonized_System_of_Classification_and_Labelling_of_Chemicals" title="Globally Harmonized System of Classification and Labelling of Chemicals"><b>GHS</b> labelling</a>: </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_hazard_pictograms" title="GHS hazard pictograms">Pictograms</a></div> </td> <td><span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-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> </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="H225: Highly flammable liquid and vapour">H225</abbr>, <abbr class="abbr" title="H302: Harmful if swallowed">H302</abbr>, <abbr class="abbr" title="H319: Causes serious eye irritation">H319</abbr>, <abbr class="abbr" title="H336: May cause drowsiness or dizziness">H336</abbr>, <abbr class="abbr" title="H373: May cause damage to organs through prolonged or repeated exposure">H373</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="P235: Keep cool.">P235</abbr>, <abbr class="abbr" title="P260: Do not breathe dust/fume/gas/mist/vapours/spray.">P260</abbr>, <abbr class="abbr" title="P305+P351+P338: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do. Continue rinsing.">P305+P351+P338</abbr> </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_dc8789d9d8c839e4" /></span><map name="ImageMap_dc8789d9d8c839e4"><area href="/wiki/NFPA_704#Blue" shape="poly" coords="23,23,47,47,23,70,0,47" alt="Health 1: Exposure would cause irritation but only minor residual injury. E.g. turpentine" title="Health 1: Exposure would cause irritation but only minor residual injury. E.g. turpentine" /><area href="/wiki/NFPA_704#Red" shape="poly" coords="47,0,70,23,47,47,23,23" alt="Flammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasoline" title="Flammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasoline" /><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 1: Exposure would cause irritation but only minor residual injury. E.g. turpentine" class="notheme mw-no-invert">1</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 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasoline" class="notheme mw-no-invert">3</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>−20 °C (−4 °F; 253 K)<sup id="cite_ref-ig_19-2" class="reference"><a href="#cite_note-ig-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> </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>465<sup id="cite_ref-ig_19-0" class="reference"><a href="#cite_note-ig-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> °C (869 °F; 738 K) </td></tr> <tr> <td><a href="/wiki/Explosive_limit" class="mw-redirect" title="Explosive limit">Explosive limits</a> </td> <td>2.5–12.8%<sup id="cite_ref-ig_19-1" class="reference"><a href="#cite_note-ig-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Threshold_limit_value" title="Threshold limit value">Threshold limit value</a> (TLV)</div> </td> <td>250 ppm<sup id="cite_ref-da_20-0" class="reference"><a href="#cite_note-da-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> (STEL), 500 ppm<sup id="cite_ref-da_20-1" class="reference"><a href="#cite_note-da-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> (C) </td></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;"><b>Lethal dose</b> or concentration (LD, LC): </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">LD<sub>50</sub> (<a href="/wiki/Lethal_dose#LD50" title="Lethal dose">median dose</a>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>5800<span class="nowrap"> </span>mg/kg (rat, oral)</li><li>3000<span class="nowrap"> </span>mg/kg (mouse, oral)</li><li>5340<span class="nowrap"> </span>mg/kg (rabbit, oral)<sup id="cite_ref-IDLH_21-0" class="reference"><a href="#cite_note-IDLH-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup></li></ul></div> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">LC<sub>50</sub> (<a href="/wiki/Lethal_dose#LC50" title="Lethal dose">median concentration</a>)</div> </td> <td>20,702<span class="nowrap"> </span>ppm (rat, 8 h)<sup id="cite_ref-IDLH_21-1" class="reference"><a href="#cite_note-IDLH-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">LC<sub>Lo</sub> (<a href="/wiki/Lethal_dose#LCLo" title="Lethal dose">lowest published</a>)</div> </td> <td>45,455<span class="nowrap"> </span>ppm (mouse, 1 h)<sup id="cite_ref-IDLH_21-2" class="reference"><a href="#cite_note-IDLH-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;"><a href="/wiki/National_Institute_for_Occupational_Safety_and_Health" title="National Institute for Occupational Safety and Health"><b>NIOSH</b></a> (US health exposure limits): </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Permissible_exposure_limit" title="Permissible exposure limit">PEL</a> (Permissible)</div> </td> <td>1000<span class="nowrap"> </span>ppm (2400<span class="nowrap"> </span>mg/m<sup>3</sup>)<sup id="cite_ref-NIOSH_3-1" class="reference"><a href="#cite_note-NIOSH-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Recommended_exposure_limit" title="Recommended exposure limit">REL</a> (Recommended)</div> </td> <td>TWA 250<span class="nowrap"> </span>ppm (590<span class="nowrap"> </span>mg/m<sup>3</sup>)<sup id="cite_ref-NIOSH_3-2" class="reference"><a href="#cite_note-NIOSH-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/IDLH" class="mw-redirect" title="IDLH">IDLH</a> (Immediate danger)</div> </td> <td>2500<span class="nowrap"> </span>ppm<sup id="cite_ref-NIOSH_3-3" class="reference"><a href="#cite_note-NIOSH-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Related compounds </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Related compounds</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a href="/wiki/Butanone" title="Butanone">Butanone</a></li><li><a href="/wiki/Isopropyl_alcohol" title="Isopropyl alcohol">Isopropyl alcohol</a></li><li><a href="/wiki/Formaldehyde" title="Formaldehyde">Formaldehyde</a></li><li><a href="/wiki/Urea" title="Urea">Urea</a></li><li><a href="/wiki/Carbonic_acid" title="Carbonic acid">Carbonic acid</a></li></ul></div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Supplementary data page </th></tr> <tr> <td colspan="2" style="text-align:center"><a href="/wiki/Acetone_(data_page)" title="Acetone (data page)">Acetone (data page)</a> </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"><div style="text-align:center;"><span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/12px-Yes_check.svg.png" decoding="async" width="12" height="12" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/18px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/24px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span> <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=477239274&page2=Acetone">verify</a></span> (<a href="/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validation" title="Wikipedia:WikiProject Chemicals/Chembox validation">what is</a> <sup><span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup> ?) </div></div> <div style="margin-top: 0.3em; text-align: center;"><a href="/wiki/Wikipedia:Chemical_infobox#References" title="Wikipedia:Chemical infobox">Infobox references</a></div> </td></tr> </tbody></table><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound</div> <p><b>Acetone</b> (<b>2-propanone</b> or <b>dimethyl ketone</b>) is an <a href="/wiki/Organic_compound" title="Organic compound">organic compound</a> with the <a href="/wiki/Chemical_formula" title="Chemical formula">formula</a> <style data-mw-deduplicate="TemplateStyles:r1123817410">.mw-parser-output .template-chem2-su{display:inline-block;font-size:80%;line-height:1;vertical-align:-0.35em}.mw-parser-output .template-chem2-su>span{display:block;text-align:left}.mw-parser-output sub.template-chem2-sub{font-size:80%;vertical-align:-0.35em}.mw-parser-output sup.template-chem2-sup{font-size:80%;vertical-align:0.65em}</style><span class="chemf nowrap">(CH<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">2</sub>CO</span>.<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> It is the simplest and smallest <a href="/wiki/Ketone" title="Ketone">ketone</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">>C=O</span>). It is a colorless, highly <a href="/wiki/Volatile_organic_compound" title="Volatile organic compound">volatile</a>, and <a href="/wiki/Flammable" class="mw-redirect" title="Flammable">flammable</a> liquid with a characteristic pungent odour, very reminiscent of the smell of <a href="/wiki/Pear_drop" title="Pear drop">pear drops</a>. </p><p>Acetone is <a href="/wiki/Miscibility" title="Miscibility">miscible</a> with <a href="/wiki/Properties_of_water" title="Properties of water">water</a> and serves as an important <a href="/wiki/Organic_solvent" class="mw-redirect" title="Organic solvent">organic solvent</a> in industry, home, and laboratory. About 6.7 million <a href="/wiki/Tonne" title="Tonne">tonnes</a> were produced worldwide in 2010, mainly for use as a solvent and for production of <a href="/wiki/Methyl_methacrylate" title="Methyl methacrylate">methyl methacrylate</a> and <a href="/wiki/Bisphenol_A" title="Bisphenol A">bisphenol A</a>, which are precursors to widely used <a href="/wiki/Plastic" title="Plastic">plastics</a>.<sup id="cite_ref-r1_23-0" class="reference"><a href="#cite_note-r1-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Ullmann_24-0" class="reference"><a href="#cite_note-Ullmann-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> It is a common building block in <a href="/wiki/Organic_chemistry" title="Organic chemistry">organic chemistry</a>. It serves as a solvent in household products such as <a href="/wiki/Nail_polish#Nail_polish_remover" title="Nail polish">nail polish remover</a> and <a href="/wiki/Paint_thinner" title="Paint thinner">paint thinner</a>. It has <a href="/wiki/Volatile_organic_compound" title="Volatile organic compound">volatile organic compound</a> (VOC)-exempt status in the United States.<sup id="cite_ref-25" class="reference"><a href="#cite_note-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> </p><p>Acetone is produced and disposed of in the human body through normal metabolic processes. It is normally present in blood and urine. People with <a href="/wiki/Diabetic_ketoacidosis" title="Diabetic ketoacidosis">diabetic ketoacidosis</a> produce it in larger amounts. <a href="/wiki/Ketogenic_diet" title="Ketogenic diet">Ketogenic diets</a> that increase <a href="/wiki/Ketone_bodies" title="Ketone bodies">ketone bodies</a> (acetone, <a href="/wiki/%CE%92-hydroxybutyric_acid" class="mw-redirect" title="Β-hydroxybutyric acid">β-hydroxybutyric acid</a> and <a href="/wiki/Acetoacetic_acid" title="Acetoacetic acid">acetoacetic acid</a>) in the blood are used to counter <a href="/wiki/Epilepsy" title="Epilepsy">epileptic attacks</a> in children who suffer from <a href="/wiki/Refractory_disease" class="mw-redirect" title="Refractory disease">refractory</a> epilepsy.<sup id="cite_ref-Freeman2007_26-0" class="reference"><a href="#cite_note-Freeman2007-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Name">Name</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetone&action=edit&section=1" title="Edit section: Name"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>From the 17th century, and before modern developments in <a href="/wiki/Organic_chemistry_nomenclature" class="mw-redirect" title="Organic chemistry nomenclature">organic chemistry nomenclature</a>, acetone was given many different names. They included "spirit of Saturn", which was given when it was thought to be a compound of <a href="/wiki/Lead" title="Lead">lead</a> and, later, "pyro-acetic spirit" and "pyro-acetic ester".<sup id="cite_ref-gorman1962_6-1" class="reference"><a href="#cite_note-gorman1962-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p><p>Prior to the name "acetone" being coined by <a href="/wiki/France" title="France">French</a> chemists (see <a class="mw-selflink-fragment" href="#History">below</a>), it was named "mesit" (from the Greek μεσίτης, meaning mediator) by <a href="/wiki/Carl_Reichenbach" title="Carl Reichenbach">Carl Reichenbach</a>, who also claimed that <a href="/wiki/Methyl_alcohol" class="mw-redirect" title="Methyl alcohol">methyl alcohol</a> consisted of mesit and <a href="/wiki/Ethyl_alcohol" class="mw-redirect" title="Ethyl alcohol">ethyl alcohol</a>.<sup id="cite_ref-27" class="reference"><a href="#cite_note-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-gorman1962_6-2" class="reference"><a href="#cite_note-gorman1962-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> Names derived from mesit include <a href="/wiki/Mesitylene" title="Mesitylene">mesitylene</a> and <a href="/wiki/Mesityl_oxide" title="Mesityl oxide">mesityl oxide</a> which were first synthesised from acetone. </p><p>Unlike many compounds with the <i>acet-</i> prefix which have a 2-carbon chain, acetone has a 3-carbon chain. That has caused confusion because there cannot be a <a href="/wiki/Ketone" title="Ketone">ketone</a> with 2 carbons. The prefix refers to acetone's relation to <a href="/wiki/Vinegar" title="Vinegar">vinegar</a> (<i>acetum</i> in <a href="/wiki/Latin" title="Latin">Latin</a>, also the source of the words "acid" and "acetic"), rather than its chemical structure.<sup id="cite_ref-chemtymology_28-0" class="reference"><a href="#cite_note-chemtymology-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="History">History</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetone&action=edit&section=2" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Acetone was first produced by <a href="/wiki/Andreas_Libavius" title="Andreas Libavius">Andreas Libavius</a> in 1606 by distillation of <a href="/wiki/Lead(II)_acetate" title="Lead(II) acetate">lead(II) acetate</a>.<sup id="cite_ref-29" class="reference"><a href="#cite_note-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-30" class="reference"><a href="#cite_note-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> </p><p>In 1832, French chemist <a href="/wiki/Jean-Baptiste_Dumas" title="Jean-Baptiste Dumas">Jean-Baptiste Dumas</a> and German chemist <a href="/wiki/Justus_von_Liebig" title="Justus von Liebig">Justus von Liebig</a> determined the <a href="/wiki/Empirical_formula" title="Empirical formula">empirical formula</a> for acetone.<sup id="cite_ref-31" class="reference"><a href="#cite_note-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-32" class="reference"><a href="#cite_note-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> In 1833, French chemists <a href="/wiki/Antoine_Bussy" title="Antoine Bussy">Antoine Bussy</a> and <a href="/wiki/Michel_Chevreul" class="mw-redirect" title="Michel Chevreul">Michel Chevreul</a> decided to name acetone by adding the suffix <i>-one</i> to the stem of the corresponding acid (viz, <a href="/wiki/Acetic_acid" title="Acetic acid">acetic acid</a>) just as a similarly prepared product of what was then confused with <a href="/wiki/Margaric_acid" title="Margaric acid">margaric acid</a> was named margarone.<sup id="cite_ref-33" class="reference"><a href="#cite_note-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-chemtymology_28-1" class="reference"><a href="#cite_note-chemtymology-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> By 1852, English chemist <a href="/wiki/Alexander_William_Williamson" title="Alexander William Williamson">Alexander William Williamson</a> realized that acetone was methyl <a href="/wiki/Acetyl" class="mw-redirect" title="Acetyl">acetyl</a>;<sup id="cite_ref-34" class="reference"><a href="#cite_note-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> the following year, the French chemist <a href="/wiki/Charles_Fr%C3%A9d%C3%A9ric_Gerhardt" title="Charles Frédéric Gerhardt">Charles Frédéric Gerhardt</a> concurred.<sup id="cite_ref-35" class="reference"><a href="#cite_note-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> In 1865, the German chemist <a href="/wiki/August_Kekul%C3%A9" title="August Kekulé">August Kekulé</a> published the modern structural formula for acetone.<sup id="cite_ref-36" class="reference"><a href="#cite_note-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-37" class="reference"><a href="#cite_note-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup> Johann Josef Loschmidt had presented the structure of acetone in 1861,<sup id="cite_ref-38" class="reference"><a href="#cite_note-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup> but his privately published booklet received little attention. During <a href="/wiki/World_War_I" title="World War I">World War I</a>, <a href="/wiki/Chaim_Weizmann" title="Chaim Weizmann">Chaim Weizmann</a> developed the process for industrial production of acetone (Weizmann Process).<sup id="cite_ref-39" class="reference"><a href="#cite_note-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Production">Production</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetone&action=edit&section=3" title="Edit section: Production"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In 2010, the worldwide production capacity for acetone was estimated at 6.7 million tonnes per year.<sup id="cite_ref-CEH_40-0" class="reference"><a href="#cite_note-CEH-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup> With 1.56 million tonnes per year, the <a href="/wiki/United_States" title="United States">United States</a> had the highest production capacity,<sup id="cite_ref-41" class="reference"><a href="#cite_note-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> followed by <a href="/wiki/Taiwan" title="Taiwan">Taiwan</a> and <a href="/wiki/PRC" class="mw-redirect" title="PRC">China</a>. The largest producer of acetone is <a href="/wiki/INEOS_Phenol" class="mw-redirect" title="INEOS Phenol">INEOS Phenol</a>, owning 17% of the world's capacity, with also significant capacity (7–8%) by <a href="/wiki/Mitsui" title="Mitsui">Mitsui</a>, <a href="/wiki/Sunoco" title="Sunoco">Sunoco</a> and <a href="/wiki/Royal_Dutch_Shell" class="mw-redirect" title="Royal Dutch Shell">Shell</a> in 2010.<sup id="cite_ref-CEH_40-1" class="reference"><a href="#cite_note-CEH-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup> INEOS Phenol also owns the world's largest production site (420,000 tonnes/annum) in <a href="/wiki/Beveren" title="Beveren">Beveren</a> (Belgium). <a href="/wiki/Spot_price" class="mw-redirect" title="Spot price">Spot price</a> of acetone in summer 2011 was 1100–1250 USD/tonne in the United States.<sup id="cite_ref-icispricing_132_42-0" class="reference"><a href="#cite_note-icispricing_132-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Current_method">Current method</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetone&action=edit&section=4" title="Edit section: Current method"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Acetone is produced directly or indirectly from <a href="/wiki/Propene" class="mw-redirect" title="Propene">propene</a>. Approximately 83% of acetone is produced via the <a href="/wiki/Cumene_process" title="Cumene process">cumene process</a>;<sup id="cite_ref-Ullmann_24-1" class="reference"><a href="#cite_note-Ullmann-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> as a result, acetone production is tied to phenol production. In the cumene process, <a href="/wiki/Benzene" title="Benzene">benzene</a> is <a href="/wiki/Alkylated" class="mw-redirect" title="Alkylated">alkylated</a> with propylene to produce <a href="/wiki/Cumene" title="Cumene">cumene</a>, which is <a href="/wiki/Oxidation" class="mw-redirect" title="Oxidation">oxidized</a> by air to produce <a href="/wiki/Phenol" title="Phenol">phenol</a> and acetone: </p> <dl><dd><span typeof="mw:File"><a href="/wiki/File:Cumene-process-overview-2D-skeletal.png" class="mw-file-description" title="Overview of the cumene process"><img alt="Overview of the cumene process" src="//upload.wikimedia.org/wikipedia/commons/thumb/3/3e/Cumene-process-overview-2D-skeletal.png/320px-Cumene-process-overview-2D-skeletal.png" decoding="async" width="320" height="86" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/3e/Cumene-process-overview-2D-skeletal.png/480px-Cumene-process-overview-2D-skeletal.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/3e/Cumene-process-overview-2D-skeletal.png/640px-Cumene-process-overview-2D-skeletal.png 2x" data-file-width="1100" data-file-height="296" /></a></span></dd></dl> <p>Other processes involve the direct oxidation of propylene (<a href="/wiki/Wacker-Hoechst_process" class="mw-redirect" title="Wacker-Hoechst process">Wacker-Hoechst process</a>), or the <a href="/wiki/Hydration_reaction" title="Hydration reaction">hydration</a> of propylene to give <a href="/wiki/2-propanol" class="mw-redirect" title="2-propanol">2-propanol</a>, which is oxidized (dehydrogenated) to acetone.<sup id="cite_ref-Ullmann_24-2" class="reference"><a href="#cite_note-Ullmann-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Older_methods">Older methods</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetone&action=edit&section=5" title="Edit section: Older methods"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Previously, acetone was produced by the <a href="/wiki/Dry_distillation" title="Dry distillation">dry distillation</a> of <a href="/wiki/Acetate" title="Acetate">acetates</a>, for example <a href="/wiki/Calcium_acetate" title="Calcium acetate">calcium acetate</a> in <a href="/wiki/Ketonic_decarboxylation" title="Ketonic decarboxylation">ketonic decarboxylation</a>. </p> <dl><dd><span class="mwe-math-element"><span class="mwe-math-mathml-inline mwe-math-mathml-a11y" style="display: none;"><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {Ca(CH3COO)2 -> CaO_{(s)}{}+ CO2_{(g)}{}+ (CH3)2CO v}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mtext>Ca</mtext> <msubsup> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mtext>COO</mtext> <mo stretchy="false">)</mo> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mo stretchy="false">⟶</mo> <msubsup> <mtext>CaO</mtext> <mrow class="MJX-TeXAtom-ORD"> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <mtext>s</mtext> <mo stretchy="false">)</mo> </mrow> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mrow class="MJX-TeXAtom-ORD"> </mrow> <mo>+</mo> <msubsup> <mtext>CO</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <mtext>g</mtext> <mo stretchy="false">)</mo> </mrow> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mrow class="MJX-TeXAtom-ORD"> </mrow> <mo>+</mo> <msubsup> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mo stretchy="false">)</mo> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mtext>CO</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">↓</mo> </mrow> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {Ca(CH3COO)2 -> CaO_{(s)}{}+ CO2_{(g)}{}+ (CH3)2CO v}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/cc50351d0c034b46898b32d08ae9cb3c10172fef" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.505ex; width:51.688ex; height:3.509ex;" alt="{\displaystyle {\ce {Ca(CH3COO)2 -> CaO_{(s)}{}+ CO2_{(g)}{}+ (CH3)2CO v}}}"></span></dd></dl> <p>After that time, during <a href="/wiki/World_War_I" title="World War I">World War I</a>, acetone was produced using <a href="/wiki/Acetone-butanol-ethanol_fermentation" class="mw-redirect" title="Acetone-butanol-ethanol fermentation">acetone-butanol-ethanol fermentation</a> with <i><a href="/wiki/Clostridium_acetobutylicum" title="Clostridium acetobutylicum">Clostridium acetobutylicum</a></i> <a href="/wiki/Bacteria" title="Bacteria">bacteria</a>, which was developed by <a href="/wiki/Chaim_Weizmann" title="Chaim Weizmann">Chaim Weizmann</a> (later the first president of <a href="/wiki/Israel" title="Israel">Israel</a>) in order to help the British war effort,<sup id="cite_ref-Ullmann_24-3" class="reference"><a href="#cite_note-Ullmann-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-43" class="reference"><a href="#cite_note-43"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup> in the preparation of <a href="/wiki/Cordite" title="Cordite">Cordite</a>.<sup id="cite_ref-44" class="reference"><a href="#cite_note-44"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup> This acetone-butanol-ethanol fermentation was eventually abandoned when newer methods with better yields were found.<sup id="cite_ref-Ullmann_24-4" class="reference"><a href="#cite_note-Ullmann-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Chemical_properties">Chemical properties</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetone&action=edit&section=6" title="Edit section: Chemical properties"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Acetone is reluctant to form a hydrate:<sup id="cite_ref-Lemal2004_45-0" class="reference"><a href="#cite_note-Lemal2004-45"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">(CH<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">2</sub>C=O + H<sub class="template-chem2-sub">2</sub>O ⇌ (CH<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">2</sub>C(OH)<sub class="template-chem2-sub">2</sub></span> K = 10<sup>−3</sup> M<sup>−1</sup></dd></dl> <p>Like most ketones, acetone exhibits the <a href="/wiki/Keto%E2%80%93enol_tautomerism" class="mw-redirect" title="Keto–enol tautomerism">keto–enol tautomerism</a> in which the nominal <a href="/wiki/Ketone" title="Ketone">keto</a> structure <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">(CH<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">2</sub>C=O</span> of acetone itself is in equilibrium with the <a href="/wiki/Enol" title="Enol">enol</a> isomer <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">(CH<sub class="template-chem2-sub">3</sub>)C(OH)=(CH<sub class="template-chem2-sub">2</sub>)</span> (<b>prop-1-en-2-ol</b>). In acetone vapor at ambient temperature, only 2.4<span style="margin:0 .15em 0 .25em">×</span>10<sup><span class="nowrap"><span data-sort-value="2999300000000000000♠"></span>−7</span></sup>% of the molecules are in the enol form.<sup id="cite_ref-hine1976_46-0" class="reference"><a href="#cite_note-hine1976-46"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><span typeof="mw:File"><a href="/wiki/File:Acetone_KetoEnol.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/de/Acetone_KetoEnol.svg/300px-Acetone_KetoEnol.svg.png" decoding="async" width="300" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/de/Acetone_KetoEnol.svg/450px-Acetone_KetoEnol.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/de/Acetone_KetoEnol.svg/600px-Acetone_KetoEnol.svg.png 2x" data-file-width="173" data-file-height="69" /></a></span></dd></dl> <p>In the presence of suitable <a href="/wiki/Catalyst" class="mw-redirect" title="Catalyst">catalysts</a>, two acetone molecules also combine to form the compound <a href="/wiki/Diacetone_alcohol" title="Diacetone alcohol">diacetone alcohol</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">(CH<sub class="template-chem2-sub">3</sub>)C=O(CH<sub class="template-chem2-sub">2</sub>)C(OH)(CH<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">2</sub></span>, which on <a href="/wiki/Dehydration_reaction" title="Dehydration reaction">dehydration</a> gives <a href="/wiki/Mesityl_oxide" title="Mesityl oxide">mesityl oxide</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">(CH<sub class="template-chem2-sub">3</sub>)C=O(CH)=C(CH<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">2</sub></span>. This product can further combine with another acetone molecule, with loss of another molecule of water, yielding <a href="/wiki/Phorone" title="Phorone">phorone</a> and other compounds.<sup id="cite_ref-47" class="reference"><a href="#cite_note-47"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup> </p><p>Acetone is a weak Lewis base that forms adducts with soft acids like <a href="/wiki/Iodine" title="Iodine">I<sub>2</sub></a> and hard acids like <a href="/wiki/Phenol" title="Phenol">phenol</a>. Acetone also forms complexes with divalent metals.<sup id="cite_ref-48" class="reference"><a href="#cite_note-48"><span class="cite-bracket">[</span>48<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-49" class="reference"><a href="#cite_note-49"><span class="cite-bracket">[</span>49<span class="cite-bracket">]</span></a></sup> </p><p>Under ultraviolet light, acetone fluoresces..<sup id="cite_ref-50" class="reference"><a href="#cite_note-50"><span class="cite-bracket">[</span>50<span class="cite-bracket">]</span></a></sup> </p><p>The <a href="/wiki/Flame_temperature" class="mw-redirect" title="Flame temperature">flame temperature</a> of pure acetone is 1980 °C.<sup id="cite_ref-51" class="reference"><a href="#cite_note-51"><span class="cite-bracket">[</span>51<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Polymerisation">Polymerisation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetone&action=edit&section=7" title="Edit section: Polymerisation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>At its melting point (−96 °C) is claimed to polymers to give a white elastic solid, soluble in acetone, stable for several hours at room temperature. To do so, a vapor of acetone is co-condensed with <a href="/wiki/Magnesium" title="Magnesium">magnesium</a> as a catalyst onto a very cold surface.<sup id="cite_ref-karg1960_52-0" class="reference"><a href="#cite_note-karg1960-52"><span class="cite-bracket">[</span>52<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-kawa1962_53-0" class="reference"><a href="#cite_note-kawa1962-53"><span class="cite-bracket">[</span>53<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-cata1996_54-0" class="reference"><a href="#cite_note-cata1996-54"><span class="cite-bracket">[</span>54<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Natural_occurrence">Natural occurrence</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetone&action=edit&section=8" title="Edit section: Natural occurrence"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Humans exhale several milligrams of acetone per day. It arises from decarboxylation of <a href="/wiki/Acetoacetate" class="mw-redirect" title="Acetoacetate">acetoacetate</a>.<sup id="cite_ref-drug_55-0" class="reference"><a href="#cite_note-drug-55"><span class="cite-bracket">[</span>55<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-56" class="reference"><a href="#cite_note-56"><span class="cite-bracket">[</span>56<span class="cite-bracket">]</span></a></sup> Small amounts of acetone are produced in the body by the <a href="/wiki/Decarboxylation" title="Decarboxylation">decarboxylation</a> of <a href="/wiki/Ketone_bodies" title="Ketone bodies">ketone bodies</a>. Certain dietary patterns, including prolonged fasting and high-fat low-carbohydrate dieting, can produce <a href="/wiki/Ketosis" title="Ketosis">ketosis</a>, in which acetone is formed in body tissue. Certain health conditions, such as alcoholism and diabetes, can produce <a href="/wiki/Ketoacidosis" title="Ketoacidosis">ketoacidosis</a>, uncontrollable ketosis that leads to a sharp, and potentially fatal, increase in the acidity of the blood. Since it is a byproduct of fermentation, acetone is a byproduct of the distillery industry.<sup id="cite_ref-drug_55-1" class="reference"><a href="#cite_note-drug-55"><span class="cite-bracket">[</span>55<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Metabolism">Metabolism</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetone&action=edit&section=9" title="Edit section: Metabolism"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Acetone can then be metabolized either by <a href="/wiki/CYP2E1" title="CYP2E1">CYP2E1</a> via <a href="/wiki/Methylglyoxal" title="Methylglyoxal">methylglyoxal</a> to <a href="/wiki/Lactic_acid" title="Lactic acid"><small>D</small>-lactate</a> and <a href="/wiki/Pyruvic_acid" title="Pyruvic acid">pyruvate</a>, and ultimately <a href="/wiki/Glucose" title="Glucose">glucose</a>/energy, or by a different pathway via <a href="/wiki/Propylene_glycol" title="Propylene glycol">propylene glycol</a> to <a href="/wiki/Pyruvate" class="mw-redirect" title="Pyruvate">pyruvate</a>, <a href="/wiki/Lactic_acid" title="Lactic acid">lactate</a>, <a href="/wiki/Acetate" title="Acetate">acetate</a> (usable for energy) and <a href="/wiki/Propionaldehyde" title="Propionaldehyde">propionaldehyde</a>.<sup id="cite_ref-Glew2010_57-0" class="reference"><a href="#cite_note-Glew2010-57"><span class="cite-bracket">[</span>57<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-58" class="reference"><a href="#cite_note-58"><span class="cite-bracket">[</span>58<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-59" class="reference"><a href="#cite_note-59"><span class="cite-bracket">[</span>59<span class="cite-bracket">]</span></a></sup> </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=Acetone&action=edit&section=10" title="Edit section: Uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>About a third of the world's acetone is used as a solvent, and a quarter is consumed as <a href="/wiki/Acetone_cyanohydrin" title="Acetone cyanohydrin">acetone cyanohydrin</a>, a precursor to <a href="/wiki/Methyl_methacrylate" title="Methyl methacrylate">methyl methacrylate</a>.<sup id="cite_ref-r1_23-1" class="reference"><a href="#cite_note-r1-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Chemical_intermediate">Chemical intermediate</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetone&action=edit&section=11" title="Edit section: Chemical intermediate"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Acetone is used to <a href="/wiki/Organic_synthesis" title="Organic synthesis">synthesize</a> <a href="/wiki/Methyl_methacrylate" title="Methyl methacrylate">methyl methacrylate</a>. It begins with the initial conversion of acetone to <a href="/wiki/Acetone_cyanohydrin" title="Acetone cyanohydrin">acetone cyanohydrin</a> via reaction with <a href="/wiki/Hydrogen_cyanide" title="Hydrogen cyanide">hydrogen cyanide</a> (HCN): </p> <dl><dd><span class="mwe-math-element"><span class="mwe-math-mathml-inline mwe-math-mathml-a11y" style="display: none;"><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {(CH3)2CO + HCN -> (CH3)2C(OH)CN}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <msubsup> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mo stretchy="false">)</mo> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mtext>CO</mtext> <mo>+</mo> <mtext>HCN</mtext> <mo stretchy="false">⟶</mo> <msubsup> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mo stretchy="false">)</mo> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mtext>C</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <mtext>OH</mtext> <mo stretchy="false">)</mo> </mrow> <mtext>CN</mtext> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {(CH3)2CO + HCN -> (CH3)2C(OH)CN}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/5ef9727c8e81b649a5abd401ecb801ed8b81c012" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:41.724ex; height:3.009ex;" alt="{\displaystyle {\ce {(CH3)2CO + HCN -> (CH3)2C(OH)CN}}}"></span></dd></dl> <p>In a subsequent step, the <a href="/wiki/Nitrile" title="Nitrile">nitrile</a> is <a href="/wiki/Hydrolysis" title="Hydrolysis">hydrolyzed</a> to the unsaturated <a href="/wiki/Amide" title="Amide">amide</a>, which is <a href="/wiki/Ester" title="Ester">esterified</a>: </p> <dl><dd><span class="mwe-math-element"><span class="mwe-math-mathml-inline mwe-math-mathml-a11y" style="display: none;"><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {(CH3)2C(OH)CN + CH3OH -> CH2=C(CH3)CO2CH3 + NH3}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <msubsup> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mo stretchy="false">)</mo> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mtext>C</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <mtext>OH</mtext> <mo stretchy="false">)</mo> </mrow> <mtext>CN</mtext> <mo>+</mo> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mtext>OH</mtext> <mo stretchy="false">⟶</mo> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mrow class="MJX-TeXAtom-ORD"> <mo>=</mo> </mrow> <mtext>C</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mo stretchy="false">)</mo> </mrow> <msubsup> <mtext>CO</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mo>+</mo> <msubsup> <mtext>NH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {(CH3)2C(OH)CN + CH3OH -> CH2=C(CH3)CO2CH3 + NH3}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/eb6ff4e533a13930df9b9186ca9325963f20fb1e" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:64.405ex; height:3.009ex;" alt="{\displaystyle {\ce {(CH3)2C(OH)CN + CH3OH -> CH2=C(CH3)CO2CH3 + NH3}}}"></span></dd></dl> <p>The third major use of acetone (about 20%)<sup id="cite_ref-r1_23-2" class="reference"><a href="#cite_note-r1-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> is synthesizing <a href="/wiki/Bisphenol_A" title="Bisphenol A">bisphenol A</a>. Bisphenol A is a component of many polymers such as <a href="/wiki/Polycarbonate" title="Polycarbonate">polycarbonates</a>, <a href="/wiki/Polyurethane" title="Polyurethane">polyurethanes</a>, and <a href="/wiki/Epoxy_resin" class="mw-redirect" title="Epoxy resin">epoxy resins</a>. The synthesis involves the <a href="/wiki/Condensation_reaction" title="Condensation reaction">condensation</a> of acetone with <a href="/wiki/Phenol" title="Phenol">phenol</a>: </p> <dl><dd><span class="mwe-math-element"><span class="mwe-math-mathml-inline mwe-math-mathml-a11y" style="display: none;"><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {(CH3)2CO + 2 C6H5OH -> (CH3)2C(C6H4OH)2 + H2O}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <msubsup> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mo stretchy="false">)</mo> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mtext>CO</mtext> <mo>+</mo> <mn>2</mn> <mspace width="thinmathspace" /> <msubsup> <mtext>C</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>6</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>5</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mtext>OH</mtext> <mo stretchy="false">⟶</mo> <msubsup> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mo stretchy="false">)</mo> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mtext>C</mtext> <msubsup> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <msubsup> <mtext>C</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>6</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>4</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mtext>OH</mtext> <mo stretchy="false">)</mo> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mo>+</mo> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mtext>O</mtext> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {(CH3)2CO + 2 C6H5OH -> (CH3)2C(C6H4OH)2 + H2O}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/49ead0126ae08e53630996f22c683e102895fd8e" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:57.799ex; height:3.009ex;" alt="{\displaystyle {\ce {(CH3)2CO + 2 C6H5OH -> (CH3)2C(C6H4OH)2 + H2O}}}"></span></dd></dl> <p>Many millions of kilograms of acetone are consumed in the production of the solvents <a href="/w/index.php?title=Methyl_isobutyl_alcohol&action=edit&redlink=1" class="new" title="Methyl isobutyl alcohol (page does not exist)">methyl isobutyl alcohol</a> and <a href="/wiki/Methyl_isobutyl_ketone" title="Methyl isobutyl ketone">methyl isobutyl ketone</a>. These products arise via an initial <a href="/wiki/Aldol_condensation" title="Aldol condensation">aldol condensation</a> to give <a href="/wiki/Diacetone_alcohol" title="Diacetone alcohol">diacetone alcohol</a>.<sup id="cite_ref-Ullmann_24-5" class="reference"><a href="#cite_note-Ullmann-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><span class="mwe-math-element"><span class="mwe-math-mathml-inline mwe-math-mathml-a11y" style="display: none;"><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {2 (CH3)2CO -> (CH3)2C(OH)CH2C(O)CH3}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> <mspace width="thinmathspace" /> <msubsup> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mo stretchy="false">)</mo> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mtext>CO</mtext> <mo stretchy="false">⟶</mo> <msubsup> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mo stretchy="false">)</mo> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mtext>C</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <mtext>OH</mtext> <mo stretchy="false">)</mo> </mrow> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mtext>C</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <mtext>O</mtext> <mo stretchy="false">)</mo> </mrow> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {2 (CH3)2CO -> (CH3)2C(OH)CH2C(O)CH3}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/f46e0dfa632a498c71336184737673e486196bcf" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:46.094ex; height:3.009ex;" alt="{\displaystyle {\ce {2 (CH3)2CO -> (CH3)2C(OH)CH2C(O)CH3}}}"></span></dd></dl> <p>Condensation with acetylene gives <a href="/w/index.php?title=2-methylbut-3-yn-2-ol&action=edit&redlink=1" class="new" title="2-methylbut-3-yn-2-ol (page does not exist)">2-methylbut-3-yn-2-ol</a>, precursor to synthetic <a href="/wiki/Terpene" title="Terpene">terpenes</a> and <a href="/wiki/Terpenoid" title="Terpenoid">terpenoids</a>.<sup id="cite_ref-60" class="reference"><a href="#cite_note-60"><span class="cite-bracket">[</span>60<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Solvent">Solvent</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetone&action=edit&section=12" title="Edit section: Solvent"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Acetone is a good solvent for many plastics and some synthetic fibers. It is used for thinning <a href="/wiki/Polyester_resin" title="Polyester resin">polyester resin</a>, cleaning tools used with it, and dissolving two-part <a href="/wiki/Epoxy" title="Epoxy">epoxies</a> and <a href="/wiki/Superglue" class="mw-redirect" title="Superglue">superglue</a> before they harden. It is used as one of the volatile components of some <a href="/wiki/Paint" title="Paint">paints</a> and <a href="/wiki/Varnish" title="Varnish">varnishes</a>. As a heavy-duty degreaser, it is useful in the preparation of metal prior to painting or <a href="/wiki/Soldering" title="Soldering">soldering</a>, and to remove <a href="/wiki/Flux_(metallurgy)#Rosin_fluxes" title="Flux (metallurgy)">rosin</a> flux after soldering (to prevent adhesion of dirt and electrical leakage and perhaps corrosion or for cosmetic reasons), although it may attack some electronic components, such as polystyrene capacitors.<sup id="cite_ref-attack_61-0" class="reference"><a href="#cite_note-attack-61"><span class="cite-bracket">[</span>61<span class="cite-bracket">]</span></a></sup> </p><p>Although itself <a href="/wiki/Flammable" class="mw-redirect" title="Flammable">flammable</a>, acetone is used extensively as a solvent for the safe transportation and storage of <a href="/wiki/Acetylene" title="Acetylene">acetylene</a>, which cannot be safely <a href="/wiki/Pressurization" title="Pressurization">pressurized</a> as a pure compound. Vessels containing a porous material are first filled with acetone followed by acetylene, which dissolves into the acetone. One litre of acetone can dissolve around 250 <a href="/wiki/Litre" title="Litre">litres</a> of acetylene at a pressure of 10 bars (1.0 MPa).<sup id="cite_ref-62" class="reference"><a href="#cite_note-62"><span class="cite-bracket">[</span>62<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-63" class="reference"><a href="#cite_note-63"><span class="cite-bracket">[</span>63<span class="cite-bracket">]</span></a></sup> </p><p>Acetone is used as a solvent by the <a href="/wiki/Pharmaceutical_industry" title="Pharmaceutical industry">pharmaceutical industry</a> and as a <a href="/wiki/Denaturation_(food)" title="Denaturation (food)">denaturant</a> in <a href="/wiki/Denatured_alcohol" title="Denatured alcohol">denatured alcohol</a>.<sup id="cite_ref-64" class="reference"><a href="#cite_note-64"><span class="cite-bracket">[</span>64<span class="cite-bracket">]</span></a></sup> Acetone is also present as an <a href="/wiki/Excipient" title="Excipient">excipient</a> in some <a href="/wiki/Pharmaceutical_drug" class="mw-redirect" title="Pharmaceutical drug">pharmaceutical drugs</a>.<sup id="cite_ref-65" class="reference"><a href="#cite_note-65"><span class="cite-bracket">[</span>65<span class="cite-bracket">]</span></a></sup><sup class="noprint Inline-Template" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Manual_of_Style/Dates_and_numbers#Chronological_items" title="Wikipedia:Manual of Style/Dates and numbers"><span title="The date of the event predicted near this tag has passed. (March 2024)">needs update</span></a></i>]</sup> </p> <div class="mw-heading mw-heading4"><h4 id="Lab_and_domestic_solvent">Lab and domestic solvent</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetone&action=edit&section=13" title="Edit section: Lab and domestic solvent"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>A variety of <a href="/wiki/Organic_reaction" title="Organic reaction">organic reactions</a> employ acetone as a <a href="/wiki/Chemical_polarity" title="Chemical polarity">polar</a>, <a href="/wiki/Aprotic_solvent" class="mw-redirect" title="Aprotic solvent">aprotic solvent</a>, e.g. the <a href="/wiki/Jones_oxidation" title="Jones oxidation">Jones oxidation</a>. </p><p>Because acetone is cheap, volatile, and dissolves or decomposes with most laboratory chemicals, an acetone rinse is the standard technique to remove solid residues from <a href="/wiki/Laboratory_glassware" title="Laboratory glassware">laboratory glassware</a> before a final wash.<sup id="cite_ref-66" class="reference"><a href="#cite_note-66"><span class="cite-bracket">[</span>66<span class="cite-bracket">]</span></a></sup> Despite common <a href="/wiki/Desiccant" title="Desiccant">desiccatory</a> use, acetone dries only via bulk displacement and dilution. It forms no <a href="/wiki/Azeotrope" title="Azeotrope">azeotropes</a> with water (see <a href="/wiki/Azeotrope_tables" title="Azeotrope tables">azeotrope tables</a>).<sup id="cite_ref-67" class="reference"><a href="#cite_note-67"><span class="cite-bracket">[</span>67<span class="cite-bracket">]</span></a></sup> Acetone also removes certain <a href="/wiki/Staining" title="Staining">stains</a> from <a href="/wiki/Microscope_slide" title="Microscope slide">microscope slides</a>.<sup id="cite_ref-68" class="reference"><a href="#cite_note-68"><span class="cite-bracket">[</span>68<span class="cite-bracket">]</span></a></sup> </p><p>Acetone freezes well below −78 °C. An acetone/dry ice mixture <a href="/wiki/Cooling_bath" title="Cooling bath">cools</a> many low-temperature reactions.<sup id="cite_ref-AA_69-0" class="reference"><a href="#cite_note-AA-69"><span class="cite-bracket">[</span>69<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Make-up_artist" title="Make-up artist">Make-up artists</a> use acetone to remove skin adhesive from the netting of wigs and mustaches by immersing the item in an acetone bath, then removing the softened glue residue with a stiff brush.<sup id="cite_ref-70" class="reference"><a href="#cite_note-70"><span class="cite-bracket">[</span>70<span class="cite-bracket">]</span></a></sup> Acetone is a main ingredient in many nail polish removers because it breaks down nail polish.<sup id="cite_ref-71" class="reference"><a href="#cite_note-71"><span class="cite-bracket">[</span>71<span class="cite-bracket">]</span></a></sup> It is used for all types of nail polish removal, like gel nail polish, dip powder and acrylic nails.<sup id="cite_ref-72" class="reference"><a href="#cite_note-72"><span class="cite-bracket">[</span>72<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Biology">Biology</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetone&action=edit&section=14" title="Edit section: Biology"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Proteins" class="mw-redirect" title="Proteins">Proteins</a> precipitate in acetone.<sup id="cite_ref-Simpson2009_73-0" class="reference"><a href="#cite_note-Simpson2009-73"><span class="cite-bracket">[</span>73<span class="cite-bracket">]</span></a></sup> The chemical modifies peptides, both at α- or ε-amino groups, and in a poorly understood but rapid modification of certain glycine residues.<sup id="cite_ref-Simpson2009_73-1" class="reference"><a href="#cite_note-Simpson2009-73"><span class="cite-bracket">[</span>73<span class="cite-bracket">]</span></a></sup> </p><p>In <a href="/wiki/Pathology" title="Pathology">pathology</a>, acetone helps find <a href="/wiki/Lymph_nodes" class="mw-redirect" title="Lymph nodes">lymph nodes</a> in fatty tissues (such as the <a href="/wiki/Mesentery" title="Mesentery">mesentery</a>) for <a href="/wiki/Tumor_staging" class="mw-redirect" title="Tumor staging">tumor staging</a>.<sup id="cite_ref-acetone-patho-springer_74-0" class="reference"><a href="#cite_note-acetone-patho-springer-74"><span class="cite-bracket">[</span>74<span class="cite-bracket">]</span></a></sup> The liquid dissolves the fat and hardens the nodes, making them easier to find.<sup id="cite_ref-acetone-patho-wiley_75-0" class="reference"><a href="#cite_note-acetone-patho-wiley-75"><span class="cite-bracket">[</span>75<span class="cite-bracket">]</span></a></sup> </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=Acetone&action=edit&section=15" title="Edit section: Medical"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Dermatologists use acetone with alcohol for <a href="/wiki/Acne_treatment" class="mw-redirect" title="Acne treatment">acne treatments</a> to <a href="/wiki/Chemical_peel" title="Chemical peel">chemically peel</a> dry skin. Common agents used today for chemical peeling are <a href="/wiki/Salicylic_acid" title="Salicylic acid">salicylic acid</a>, <a href="/wiki/Glycolic_acid" title="Glycolic acid">glycolic acid</a>, <a href="/wiki/Azelaic_acid" title="Azelaic acid">azelaic acid</a>, 30% <a href="/wiki/Salicylic_acid" title="Salicylic acid">salicylic acid</a> in <a href="/wiki/Ethanol" title="Ethanol">ethanol</a>, and <a href="/wiki/Trichloroacetic_acid" title="Trichloroacetic acid">trichloroacetic acid</a> (TCA). Prior to chemexfoliation, the skin is cleaned and excess fat removed in a process called defatting. Acetone, <a href="/wiki/Hexachlorophene" title="Hexachlorophene">hexachlorophene</a>, or a combination of these agents was used in this process.<sup id="cite_ref-76" class="reference"><a href="#cite_note-76"><span class="cite-bracket">[</span>76<span class="cite-bracket">]</span></a></sup> </p><p>Acetone has been shown to have <a href="/wiki/Anticonvulsant" title="Anticonvulsant">anticonvulsant</a> effects in animal models of <a href="/wiki/Epilepsy" title="Epilepsy">epilepsy</a>, in the absence of toxicity, when administered in millimolar concentrations.<sup id="cite_ref-Likhodii_77-0" class="reference"><a href="#cite_note-Likhodii-77"><span class="cite-bracket">[</span>77<span class="cite-bracket">]</span></a></sup> It has been hypothesized that the high-fat low-carbohydrate <a href="/wiki/Ketogenic_diet" title="Ketogenic diet">ketogenic diet</a> used clinically to control drug-resistant epilepsy in children works by elevating acetone in the brain.<sup id="cite_ref-Likhodii_77-1" class="reference"><a href="#cite_note-Likhodii-77"><span class="cite-bracket">[</span>77<span class="cite-bracket">]</span></a></sup> Because of their higher energy requirements, children have higher acetone production than most adults – and the younger the child, the higher the expected production. This indicates that children are not uniquely susceptible to acetone exposure. External exposures are small compared to the exposures associated with the ketogenic diet.<sup id="cite_ref-acc_78-0" class="reference"><a href="#cite_note-acc-78"><span class="cite-bracket">[</span>78<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Safety">Safety</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetone&action=edit&section=16" title="Edit section: Safety"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Acetone's most hazardous property is its extreme flammability. In small amounts, acetone burns with a <a href="/wiki/Oxidizing_flame" class="mw-redirect" title="Oxidizing flame">dull blue flame</a>; in larger amounts, fuel evaporation causes incomplete combustion and a <a href="/wiki/Reducing_flame" class="mw-redirect" title="Reducing flame">bright yellow flame</a>. When hotter than acetone's <a href="/wiki/Flash_point" title="Flash point">flash point</a> of −20 °C (−4 °F), air mixtures of 2.5‑12.8% acetone (by volume) may explode or cause a <a href="/wiki/Flashover" title="Flashover">flash fire</a>. Vapors can flow along surfaces to distant ignition sources and flash back. </p><p><a href="/wiki/Static_electricity" title="Static electricity">Static</a> discharge may also ignite acetone vapors, though acetone has a very high ignition initiation energy and accidental ignition is rare.<sup id="cite_ref-msds_79-0" class="reference"><a href="#cite_note-msds-79"><span class="cite-bracket">[</span>79<span class="cite-bracket">]</span></a></sup> Acetone's <a href="/wiki/Auto-ignition_temperature" class="mw-redirect" title="Auto-ignition temperature">auto-ignition temperature</a> is the relatively high 465 °C (869 °F);<sup id="cite_ref-ig_19-3" class="reference"><a href="#cite_note-ig-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> moreover, auto-ignition temperature depends upon experimental conditions, such as exposure time, and has been quoted as high as 535 °C.<sup id="cite_ref-80" class="reference"><a href="#cite_note-80"><span class="cite-bracket">[</span>80<span class="cite-bracket">]</span></a></sup> Even pouring or spraying acetone over red-glowing coal will not ignite it, due to the high vapour concentration and the cooling effect of evaporation.<sup id="cite_ref-msds_79-1" class="reference"><a href="#cite_note-msds-79"><span class="cite-bracket">[</span>79<span class="cite-bracket">]</span></a></sup> </p><p>Acetone should be stored away from strong oxidizers, such as concentrated <a href="/wiki/Nitric_acid" title="Nitric acid">nitric</a> and <a href="/wiki/Sulfuric_acid" title="Sulfuric acid">sulfuric acid</a> mixtures.<sup id="cite_ref-81" class="reference"><a href="#cite_note-81"><span class="cite-bracket">[</span>81<span class="cite-bracket">]</span></a></sup> It may also explode when mixed with <a href="/wiki/Chloroform" title="Chloroform">chloroform</a> in the presence of a base.<sup id="cite_ref-82" class="reference"><a href="#cite_note-82"><span class="cite-bracket">[</span>82<span class="cite-bracket">]</span></a></sup><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. (October 2023)">clarification needed</span></a></i>]</sup> When oxidized without combustion, for example with <a href="/wiki/Hydrogen_peroxide" title="Hydrogen peroxide">hydrogen peroxide</a>, acetone may form <a href="/wiki/Acetone_peroxide" title="Acetone peroxide">acetone peroxide</a>, a highly <a href="/wiki/Chemical_stability" title="Chemical stability">unstable</a> <a href="/wiki/Primary_explosive" class="mw-redirect" title="Primary explosive">primary explosive</a>. Acetone peroxide may be formed accidentally, e.g. when waste <a href="/wiki/Hydrogen_peroxide" title="Hydrogen peroxide">peroxide</a> is poured into waste solvents.<sup id="cite_ref-83" class="reference"><a href="#cite_note-83"><span class="cite-bracket">[</span>83<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Toxicity">Toxicity</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetone&action=edit&section=17" title="Edit section: Toxicity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Acetone occurs naturally as part of certain metabolic processes in the human body, and has been studied extensively and is believed to exhibit only slight toxicity in normal use. There is no strong evidence of chronic health effects if basic precautions are followed.<sup id="cite_ref-84" class="reference"><a href="#cite_note-84"><span class="cite-bracket">[</span>84<span class="cite-bracket">]</span></a></sup> It is generally recognized to have low acute and chronic toxicity if ingested and/or inhaled.<sup id="cite_ref-sids_85-0" class="reference"><a href="#cite_note-sids-85"><span class="cite-bracket">[</span>85<span class="cite-bracket">]</span></a></sup> Acetone is not currently regarded as a <a href="/wiki/Carcinogen" title="Carcinogen">carcinogen</a>, a <a href="/wiki/Mutagen" title="Mutagen">mutagen</a>, or a concern for chronic <a href="/wiki/Neurotoxicity" title="Neurotoxicity">neurotoxicity</a> effects.<sup id="cite_ref-msds_79-2" class="reference"><a href="#cite_note-msds-79"><span class="cite-bracket">[</span>79<span class="cite-bracket">]</span></a></sup> </p><p>Acetone can be found as an ingredient in a variety of consumer products ranging from cosmetics to processed and unprocessed foods. Acetone has been rated as a <a href="/wiki/Generally_recognized_as_safe" title="Generally recognized as safe">generally recognized as safe</a> (GRAS) substance when present in drinks, baked foods, desserts, and preserves at concentrations ranging from 5 to 8 mg/L.<sup id="cite_ref-sids_85-1" class="reference"><a href="#cite_note-sids-85"><span class="cite-bracket">[</span>85<span class="cite-bracket">]</span></a></sup> </p><p>Acetone is however an irritant, causing mild skin and moderate-to-severe eye irritation. At high vapor concentrations, it may depress the <a href="/wiki/Central_nervous_system" title="Central nervous system">central nervous system</a> like many other solvents.<sup id="cite_ref-86" class="reference"><a href="#cite_note-86"><span class="cite-bracket">[</span>86<span class="cite-bracket">]</span></a></sup> Acute toxicity for mice by ingestion (LD<sub>50</sub>) is 3 g/kg, and by inhalation (LC<sub>50</sub>) is 44 g/m<sup>3</sup> over 4 hours.<sup id="cite_ref-87" class="reference"><a href="#cite_note-87"><span class="cite-bracket">[</span>87<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Environmental_effects">Environmental effects</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetone&action=edit&section=18" title="Edit section: Environmental effects"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Although acetone occurs naturally in the environment in plants, trees, volcanic gases, forest fires, and as a product of the breakdown of body fat,<sup id="cite_ref-atsdr_88-0" class="reference"><a href="#cite_note-atsdr-88"><span class="cite-bracket">[</span>88<span class="cite-bracket">]</span></a></sup> the majority of the acetone released into the environment is of industrial origin.<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. (October 2023)">clarification needed</span></a></i>]</sup> Acetone evaporates rapidly, even from water and soil. Once in the atmosphere, it has a 22-day half-life and is degraded by UV light via <a href="/wiki/Photolysis" class="mw-redirect" title="Photolysis">photolysis</a> (primarily into <a href="/wiki/Methane" title="Methane">methane</a> and <a href="/wiki/Ethane" title="Ethane">ethane</a>.<sup id="cite_ref-89" class="reference"><a href="#cite_note-89"><span class="cite-bracket">[</span>89<span class="cite-bracket">]</span></a></sup>) Consumption by microorganisms contributes to the dissipation of acetone in soil, animals, or waterways.<sup id="cite_ref-atsdr_88-1" class="reference"><a href="#cite_note-atsdr-88"><span class="cite-bracket">[</span>88<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="EPA_classification">EPA classification</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetone&action=edit&section=19" title="Edit section: EPA classification"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In 1995, the <a href="/wiki/United_States_Environmental_Protection_Agency" title="United States Environmental Protection Agency">United States Environmental Protection Agency</a> (EPA) removed acetone from the list of <a href="/wiki/Volatile_organic_compound" title="Volatile organic compound">volatile organic compounds</a>. The companies requesting the removal argued that it would "contribute to the achievement of several important environmental goals and would support EPA's pollution prevention efforts", and that acetone could be used as a substitute for several compounds that are listed as hazardous air pollutants (HAP) under section 112 of the <a href="/wiki/Clean_Air_Act_(United_States)" title="Clean Air Act (United States)">Clean Air Act</a>.<sup id="cite_ref-90" class="reference"><a href="#cite_note-90"><span class="cite-bracket">[</span>90<span class="cite-bracket">]</span></a></sup> In making its decision EPA conducted an extensive review of the available toxicity data on acetone, which was continued through the 2000s. It found that the evaluable "data are inadequate for an assessment of the human carcinogenic potential of acetone".<sup id="cite_ref-smell_9-1" class="reference"><a href="#cite_note-smell-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Extraterrestrial_occurrence">Extraterrestrial occurrence</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetone&action=edit&section=20" title="Edit section: Extraterrestrial occurrence"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>On 30 July 2015, scientists reported that upon the first touchdown of the <i><a href="/wiki/Philae_(spacecraft)" title="Philae (spacecraft)">Philae</a></i> lander on <a href="/wiki/Comet" title="Comet">comet</a> <a href="/wiki/67P/Churyumov%E2%80%93Gerasimenko" title="67P/Churyumov–Gerasimenko">67P</a><span class="nowrap" style="padding-left:0.1em;">'s</span> surface, measurements by the COSAC and Ptolemy instruments revealed sixteen <a href="/wiki/Organic_compound" title="Organic compound">organic compounds</a>, four of which were seen for the first time on a comet, including <a href="/wiki/Acetamide" title="Acetamide">acetamide</a>, acetone, <a href="/wiki/Methyl_isocyanate" title="Methyl isocyanate">methyl isocyanate</a>, and <a href="/wiki/Propionaldehyde" title="Propionaldehyde">propionaldehyde</a>.<sup id="cite_ref-wapo20150730_91-0" class="reference"><a href="#cite_note-wapo20150730-91"><span class="cite-bracket">[</span>91<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-esa20150730_92-0" class="reference"><a href="#cite_note-esa20150730-92"><span class="cite-bracket">[</span>92<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-SCI-20150731_93-0" class="reference"><a href="#cite_note-SCI-20150731-93"><span class="cite-bracket">[</span>93<span class="cite-bracket">]</span></a></sup> </p> <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=Acetone&action=edit&section=21" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist reflist-columns references-column-width" style="column-width: 30em;"> <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"><i><a href="/wiki/The_Merck_Index" class="mw-redirect" title="The Merck Index">The Merck Index</a></i>, <b>15th Ed.</b> (2013), p. 13, <a rel="nofollow" class="external text" href="http://www.rsc.org/Merck-Index/monograph/mono1500000065">Acetone Monograph</a> <b>65</b>, O'Neil: <a href="/wiki/The_Royal_Society_of_Chemistry" class="mw-redirect" title="The Royal Society of Chemistry">The Royal Society of Chemistry</a>.<span style="font-size:0.95em; font-size:95%; color: var( --color-subtle, #555 )">(subscription required)</span></span> </li> <li id="cite_note-nist-2"><span class="mw-cite-backlink">^ <a href="#cite_ref-nist_2-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-nist_2-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-nist_2-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-nist_2-3"><sup><i><b>d</b></i></sup></a></span> <span class="reference-text"><a rel="nofollow" class="external text" href="http://webbook.nist.gov/cgi/cbook.cgi?ID=C67641&Mask=FFFF&Units=SI">Acetone</a> in Linstrom, Peter J.; Mallard, William G. (eds.); <i><a rel="nofollow" class="external text" href="http://webbook.nist.gov">NIST Chemistry WebBook</a>, NIST Standard Reference Database Number 69</i>, National Institute of Standards and Technology, Gaithersburg (MD) </span> </li> <li id="cite_note-NIOSH-3"><span class="mw-cite-backlink">^ <a href="#cite_ref-NIOSH_3-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-NIOSH_3-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-NIOSH_3-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-NIOSH_3-3"><sup><i><b>d</b></i></sup></a></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFNIOSH_Pocket_Guide_to_Chemical_Hazards" class="citation web cs1">NIOSH Pocket Guide to Chemical Hazards. <a rel="nofollow" class="external text" href="https://www.cdc.gov/niosh/npg/npgd0004.html">"#0004"</a>. <a href="/wiki/National_Institute_for_Occupational_Safety_and_Health" title="National Institute for Occupational Safety and Health">National Institute for Occupational Safety and Health</a> (NIOSH).</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=%230004&rft.pub=National+Institute+for+Occupational+Safety+and+Health+%28NIOSH%29&rft.au=NIOSH+Pocket+Guide+to+Chemical+Hazards&rft_id=https%3A%2F%2Fwww.cdc.gov%2Fniosh%2Fnpg%2Fnpgd0004.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcetone" class="Z3988"></span></span> </li> <li id="cite_note-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-4">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKlamt2005" class="citation book cs1">Klamt, Andreas (2005). <i>COSMO-RS: From Quantum Chemistry to Fluid Phase Thermodynamics and Drug Design</i>. Elsevier. pp. 92–94. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-444-51994-8" title="Special:BookSources/978-0-444-51994-8"><bdi>978-0-444-51994-8</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=COSMO-RS%3A+From+Quantum+Chemistry+to+Fluid+Phase+Thermodynamics+and+Drug+Design&rft.pages=92-94&rft.pub=Elsevier&rft.date=2005&rft.isbn=978-0-444-51994-8&rft.aulast=Klamt&rft.aufirst=Andreas&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcetone" class="Z3988"></span></span> </li> <li id="cite_note-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-5">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMyers2007" class="citation book cs1">Myers, Richard L. (2007). <a rel="nofollow" class="external text" href="https://archive.org/details/100mostimportant0000myer/page/4"><i>The 100 Most Important Chemical Compounds: A Reference Guide</i></a>. Greenwood. pp. <a rel="nofollow" class="external text" href="https://archive.org/details/100mostimportant0000myer/page/4">4–6</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-313-08057-9" title="Special:BookSources/978-0-313-08057-9"><bdi>978-0-313-08057-9</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+100+Most+Important+Chemical+Compounds%3A+A+Reference+Guide&rft.pages=4-6&rft.pub=Greenwood&rft.date=2007&rft.isbn=978-0-313-08057-9&rft.aulast=Myers&rft.aufirst=Richard+L.&rft_id=https%3A%2F%2Farchive.org%2Fdetails%2F100mostimportant0000myer%2Fpage%2F4&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcetone" class="Z3988"></span></span> </li> <li id="cite_note-gorman1962-6"><span class="mw-cite-backlink">^ <a href="#cite_ref-gorman1962_6-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-gorman1962_6-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-gorman1962_6-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text">Mel Gorman, History of acetone (1600–1850), 1962</span> </li> <li id="cite_note-7"><span class="mw-cite-backlink"><b><a href="#cite_ref-7">^</a></b></span> <span class="reference-text"><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a> lists 'acetone' as a valid, expert-verified name for what would systematically be called 'propan-2-one'.</span> </li> <li id="cite_note-iupac2013-8"><span class="mw-cite-backlink"><b><a href="#cite_ref-iupac2013_8-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation book cs1"><i>Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book)</i>. Cambridge: <a href="/wiki/Royal_Society_of_Chemistry" title="Royal Society of Chemistry">The Royal Society of Chemistry</a>. 2014. p. 723. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1039%2F9781849733069-FP001">10.1039/9781849733069-FP001</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-85404-182-4" title="Special:BookSources/978-0-85404-182-4"><bdi>978-0-85404-182-4</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Nomenclature+of+Organic+Chemistry+%3A+IUPAC+Recommendations+and+Preferred+Names+2013+%28Blue+Book%29&rft.place=Cambridge&rft.pages=723&rft.pub=The+Royal+Society+of+Chemistry&rft.date=2014&rft_id=info%3Adoi%2F10.1039%2F9781849733069-FP001&rft.isbn=978-0-85404-182-4&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcetone" class="Z3988"></span></span> </li> <li id="cite_note-smell-9"><span class="mw-cite-backlink">^ <a href="#cite_ref-smell_9-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-smell_9-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><a rel="nofollow" class="external text" href="https://www.atsdr.cdc.gov/toxprofiles/tp21.pdf">Toxicological Profile for Acetone</a>. U.S. Environmental Protection Agency June 2022 p. 7</span> </li> <li id="cite_note-h1-10"><span class="mw-cite-backlink">^ <a href="#cite_ref-h1_10-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-h1_10-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-h1_10-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-h1_10-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-h1_10-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-h1_10-5"><sup><i><b>f</b></i></sup></a></span> <span class="reference-text"><a href="#Haynes">Haynes</a>, p. 3.4</span> </li> <li id="cite_note-11"><span class="mw-cite-backlink"><b><a href="#cite_ref-11">^</a></b></span> <span class="reference-text"><a href="#Haynes">Haynes</a>, p. 5.173</span> </li> <li id="cite_note-12"><span class="mw-cite-backlink"><b><a href="#cite_ref-12">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFChiangKresgeTangWirz1984" class="citation journal cs1">Chiang, Yvonne; Kresge, A. Jerry; Tang, Yui S.; Wirz, Jakob (1984). "The pKa and keto-enol equilibrium constant of acetone in aqueous solution". <i>Journal of the American Chemical Society</i>. <b>106</b> (2): 460–462. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fja00314a055">10.1021/ja00314a055</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+the+American+Chemical+Society&rft.atitle=The+pKa+and+keto-enol+equilibrium+constant+of+acetone+in+aqueous+solution&rft.volume=106&rft.issue=2&rft.pages=460-462&rft.date=1984&rft_id=info%3Adoi%2F10.1021%2Fja00314a055&rft.aulast=Chiang&rft.aufirst=Yvonne&rft.au=Kresge%2C+A.+Jerry&rft.au=Tang%2C+Yui+S.&rft.au=Wirz%2C+Jakob&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcetone" class="Z3988"></span></span> </li> <li id="cite_note-Bordwell-13"><span class="mw-cite-backlink"><b><a href="#cite_ref-Bordwell_13-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBordwell1988" class="citation journal cs1">Bordwell, Frederick G. (1988). "Equilibrium acidities in dimethyl sulfoxide solution". <i>Accounts of Chemical Research</i>. <b>21</b> (12): 456–463. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Far00156a004">10.1021/ar00156a004</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:26624076">26624076</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Accounts+of+Chemical+Research&rft.atitle=Equilibrium+acidities+in+dimethyl+sulfoxide+solution&rft.volume=21&rft.issue=12&rft.pages=456-463&rft.date=1988&rft_id=info%3Adoi%2F10.1021%2Far00156a004&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A26624076%23id-name%3DS2CID&rft.aulast=Bordwell&rft.aufirst=Frederick+G.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcetone" class="Z3988"></span></span> </li> <li id="cite_note-14"><span class="mw-cite-backlink"><b><a href="#cite_ref-14">^</a></b></span> <span class="reference-text"><a href="#Haynes">Haynes</a>, p. 3.576</span> </li> <li id="cite_note-15"><span class="mw-cite-backlink"><b><a href="#cite_ref-15">^</a></b></span> <span class="reference-text"><a href="#Haynes">Haynes</a>, p. 6.254</span> </li> <li id="cite_note-16"><span class="mw-cite-backlink"><b><a href="#cite_ref-16">^</a></b></span> <span class="reference-text"><a href="#Haynes">Haynes</a>, p. 6.243</span> </li> <li id="cite_note-17"><span class="mw-cite-backlink"><b><a href="#cite_ref-17">^</a></b></span> <span class="reference-text"><a href="#Haynes">Haynes</a>, p. 9.60</span> </li> <li id="cite_note-18"><span class="mw-cite-backlink"><b><a href="#cite_ref-18">^</a></b></span> <span class="reference-text"><a href="#Haynes">Haynes</a>, pp. 5.3, 5.67</span> </li> <li id="cite_note-ig-19"><span class="mw-cite-backlink">^ <a href="#cite_ref-ig_19-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-ig_19-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-ig_19-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-ig_19-3"><sup><i><b>d</b></i></sup></a></span> <span class="reference-text"><a href="#Haynes">Haynes</a>, p. 15.13</span> </li> <li id="cite_note-da-20"><span class="mw-cite-backlink">^ <a href="#cite_ref-da_20-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-da_20-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><a href="#Haynes">Haynes</a>, p. 16.34</span> </li> <li id="cite_note-IDLH-21"><span class="mw-cite-backlink">^ <a href="#cite_ref-IDLH_21-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-IDLH_21-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-IDLH_21-2"><sup><i><b>c</b></i></sup></a></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.cdc.gov/niosh/idlh/67641.html">"Acetone"</a>. <i>Immediately Dangerous to Life or Health Concentrations (IDLH)</i>. <a href="/wiki/National_Institute_for_Occupational_Safety_and_Health" title="National Institute for Occupational Safety and Health">National Institute for Occupational Safety and Health</a> (NIOSH).</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Immediately+Dangerous+to+Life+or+Health+Concentrations+%28IDLH%29&rft.atitle=Acetone&rft_id=https%3A%2F%2Fwww.cdc.gov%2Fniosh%2Fidlh%2F67641.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcetone" class="Z3988"></span></span> </li> <li id="cite_note-22"><span class="mw-cite-backlink"><b><a href="#cite_ref-22">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFAllenBowenSuttonBastiansen1952" class="citation journal cs1">Allen, P .W.; Bowen, H. J. M.; Sutton, L. E.; Bastiansen, O. (1952). 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Greenwood Press. p. 5. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780313337581" title="Special:BookSources/9780313337581"><bdi>9780313337581</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+100+Most+Important+Chemical+Compounds%3A+A+Reference+Guide&rft.pages=5&rft.pub=Greenwood+Press&rft.date=2007&rft.isbn=9780313337581&rft.aulast=Myers&rft.aufirst=Richard+Leroy&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcetone" class="Z3988"></span></span> </li> <li id="cite_note-44"><span class="mw-cite-backlink"><b><a href="#cite_ref-44">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWittcoffGreen2003" class="citation book cs1">Wittcoff, M.M.; Green, H.A. 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Berlin. p. 20. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-642-40954-7" title="Special:BookSources/978-3-642-40954-7"><bdi>978-3-642-40954-7</bdi></a>. <a href="/wiki/OCLC_(identifier)" class="mw-redirect" title="OCLC (identifier)">OCLC</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/oclc/888160502">888160502</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Process+and+plant+safety&rft.place=Berlin&rft.pages=20&rft.date=2014&rft_id=info%3Aoclcnum%2F888160502&rft.isbn=978-3-642-40954-7&rft.aulast=Hauptmanns&rft.aufirst=Ulrich&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcetone" class="Z3988"></span><span class="cs1-maint citation-comment"><code class="cs1-code">{{<a href="/wiki/Template:Cite_book" title="Template:Cite book">cite book</a>}}</code>: CS1 maint: location missing publisher (<a href="/wiki/Category:CS1_maint:_location_missing_publisher" title="Category:CS1 maint: location missing publisher">link</a>)</span></span> </li> <li id="cite_note-81"><span class="mw-cite-backlink"><b><a href="#cite_ref-81">^</a></b></span> <span class="reference-text"><a href="#Haynes">Haynes</a>, p. 16.3</span> </li> <li id="cite_note-82"><span class="mw-cite-backlink"><b><a href="#cite_ref-82">^</a></b></span> <span class="reference-text"><a href="#Haynes">Haynes</a>, p. 16.5</span> </li> <li id="cite_note-83"><span class="mw-cite-backlink"><b><a href="#cite_ref-83">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBinghamCohrssenPatty2012" class="citation book cs1">Bingham, Eula; Cohrssen, Barbara; Patty, F. A. (2012). <i>Patty's toxicology</i>. Hoboken, New Jersey. p. 736. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-62198-026-1" title="Special:BookSources/978-1-62198-026-1"><bdi>978-1-62198-026-1</bdi></a>. <a href="/wiki/OCLC_(identifier)" class="mw-redirect" title="OCLC (identifier)">OCLC</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/oclc/810064538">810064538</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Patty%27s+toxicology&rft.place=Hoboken%2C+New+Jersey&rft.pages=736&rft.date=2012&rft_id=info%3Aoclcnum%2F810064538&rft.isbn=978-1-62198-026-1&rft.aulast=Bingham&rft.aufirst=Eula&rft.au=Cohrssen%2C+Barbara&rft.au=Patty%2C+F.+A.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcetone" class="Z3988"></span><span class="cs1-maint citation-comment"><code class="cs1-code">{{<a href="/wiki/Template:Cite_book" title="Template:Cite book">cite book</a>}}</code>: CS1 maint: location missing publisher (<a href="/wiki/Category:CS1_maint:_location_missing_publisher" title="Category:CS1 maint: location missing publisher">link</a>)</span></span> </li> <li id="cite_note-84"><span class="mw-cite-backlink"><b><a href="#cite_ref-84">^</a></b></span> <span class="reference-text"><a rel="nofollow" class="external text" href="http://ccohs.ca/oshanswers/chemicals/chem_profiles/acetone/basic_ace.html">Basic Information on Acetone</a>. Ccohs.ca (1999-02-19). Retrieved on 2012-11-26.</span> </li> <li id="cite_note-sids-85"><span class="mw-cite-backlink">^ <a href="#cite_ref-sids_85-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-sids_85-1"><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 class="citation web cs1"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20140309040008/http://www.inchem.org/documents/sids/sids/67641.pdf">"SIDS Initial Assessment Report: Acetone"</a> <span class="cs1-format">(PDF)</span>. Environmental Protection Agency. Archived from <a rel="nofollow" class="external text" href="http://www.inchem.org/documents/sids/sids/67641.pdf">the original</a> <span class="cs1-format">(PDF)</span> on 2014-03-09<span class="reference-accessdate">. Retrieved <span class="nowrap">2014-09-11</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=SIDS+Initial+Assessment+Report%3A+Acetone&rft.pub=Environmental+Protection+Agency&rft_id=http%3A%2F%2Fwww.inchem.org%2Fdocuments%2Fsids%2Fsids%2F67641.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcetone" class="Z3988"></span></span> </li> <li id="cite_note-86"><span class="mw-cite-backlink"><b><a href="#cite_ref-86">^</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="http://ccohs.ca/oshanswers/chemicals/chem_profiles/acetone/health_ace.html">"What are the potential health effects of acetone?"</a>. Canadian Centre for Occupational Health and Safety. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20081017104151/http://www.ccohs.ca/oshanswers/chemicals/chem_profiles/acetone/health_ace.html">Archived</a> from the original on 2008-10-17<span class="reference-accessdate">. Retrieved <span class="nowrap">2008-10-21</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=What+are+the+potential+health+effects+of+acetone%3F&rft.pub=Canadian+Centre+for+Occupational+Health+and+Safety&rft_id=http%3A%2F%2Fccohs.ca%2Foshanswers%2Fchemicals%2Fchem_profiles%2Facetone%2Fhealth_ace.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcetone" class="Z3988"></span></span> </li> <li id="cite_note-87"><span class="mw-cite-backlink"><b><a href="#cite_ref-87">^</a></b></span> <span class="reference-text"><a rel="nofollow" class="external text" href="http://www.sciencelab.com/msds.php?msdsId=9927062">Safety (MSDS) data for propanone</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20180316170132/http://www.sciencelab.com/msds.php?msdsId=9927062">Archived</a> 2018-03-16 at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a> sciencelab.com/msds Retrieved on 2018-03-19</span> </li> <li id="cite_note-atsdr-88"><span class="mw-cite-backlink">^ <a href="#cite_ref-atsdr_88-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-atsdr_88-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><a rel="nofollow" class="external text" href="https://www.atsdr.cdc.gov/toxfaqs/tfacts21.pdf">Acetone</a>, Agency for Toxic Substances and Disease Registry ToxFAQs, 1995</span> </li> <li id="cite_note-89"><span class="mw-cite-backlink"><b><a href="#cite_ref-89">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFDarwentAllardHartmanLange1960" class="citation journal cs1">Darwent, B. deB.; Allard, M. J.; Hartman, M. F.; Lange, L. J. (1960). "The Photolysis of Acetone". <i>Journal of Physical Chemistry</i>. <b>64</b> (12): 1847–1850. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fj100841a010">10.1021/j100841a010</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Physical+Chemistry&rft.atitle=The+Photolysis+of+Acetone&rft.volume=64&rft.issue=12&rft.pages=1847-1850&rft.date=1960&rft_id=info%3Adoi%2F10.1021%2Fj100841a010&rft.aulast=Darwent&rft.aufirst=B.+deB.&rft.au=Allard%2C+M.+J.&rft.au=Hartman%2C+M.+F.&rft.au=Lange%2C+L.+J.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcetone" class="Z3988"></span></span> </li> <li id="cite_note-90"><span class="mw-cite-backlink"><b><a href="#cite_ref-90">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFU.S._Environmental_Protection_Agency1995" class="citation journal cs1">U.S. Environmental Protection Agency (June 16, 1995). <a rel="nofollow" class="external text" href="https://www.govinfo.gov/content/pkg/FR-1995-06-16/pdf/95-14804.pdf">"Air Quality: Revision to Definition of Volatile Organic Compounds—Exclusion of Acetone"</a> <span class="cs1-format">(PDF)</span>. <i>Federal Register</i>. <b>60</b> (116): 31634–31637.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Federal+Register&rft.atitle=Air+Quality%3A+Revision+to+Definition+of+Volatile+Organic+Compounds%E2%80%94Exclusion+of+Acetone&rft.volume=60&rft.issue=116&rft.pages=31634-31637&rft.date=1995-06-16&rft.au=U.S.+Environmental+Protection+Agency&rft_id=https%3A%2F%2Fwww.govinfo.gov%2Fcontent%2Fpkg%2FFR-1995-06-16%2Fpdf%2F95-14804.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcetone" class="Z3988"></span></span> </li> <li id="cite_note-wapo20150730-91"><span class="mw-cite-backlink"><b><a href="#cite_ref-wapo20150730_91-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFJordans2015" class="citation news cs1">Jordans, Frank (30 July 2015). <a rel="nofollow" class="external text" href="https://web.archive.org/web/20181223235109/https://www.washingtonpost.com/world/philae-probe-finds-evidence-that-comets-can-be-cosmic-labs/2015/07/30/63a2fc0e-36e5-11e5-ab7b-6416d97c73c2_story.html">"Philae probe finds evidence that comets can be cosmic labs"</a>. <i>The Washington Post</i>. Associated Press. Archived from <a rel="nofollow" class="external text" href="https://www.washingtonpost.com/world/philae-probe-finds-evidence-that-comets-can-be-cosmic-labs/2015/07/30/63a2fc0e-36e5-11e5-ab7b-6416d97c73c2_story.html">the original</a> on 23 December 2018<span class="reference-accessdate">. Retrieved <span class="nowrap">30 July</span> 2015</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Washington+Post&rft.atitle=Philae+probe+finds+evidence+that+comets+can+be+cosmic+labs&rft.date=2015-07-30&rft.aulast=Jordans&rft.aufirst=Frank&rft_id=https%3A%2F%2Fwww.washingtonpost.com%2Fworld%2Fphilae-probe-finds-evidence-that-comets-can-be-cosmic-labs%2F2015%2F07%2F30%2F63a2fc0e-36e5-11e5-ab7b-6416d97c73c2_story.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcetone" class="Z3988"></span></span> </li> <li id="cite_note-esa20150730-92"><span class="mw-cite-backlink"><b><a href="#cite_ref-esa20150730_92-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.esa.int/Science_Exploration/Space_Science/Rosetta/Science_on_the_surface_of_a_comet">"Science on the Surface of a Comet"</a>. European Space Agency. 30 July 2015<span class="reference-accessdate">. Retrieved <span class="nowrap">30 July</span> 2015</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Science+on+the+Surface+of+a+Comet&rft.pub=European+Space+Agency&rft.date=2015-07-30&rft_id=https%3A%2F%2Fwww.esa.int%2FScience_Exploration%2FSpace_Science%2FRosetta%2FScience_on_the_surface_of_a_comet&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcetone" class="Z3988"></span></span> </li> <li id="cite_note-SCI-20150731-93"><span class="mw-cite-backlink"><b><a href="#cite_ref-SCI-20150731_93-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBibringTaylorAlexanderAuster2015" class="citation journal cs1">Bibring, J.-P.; Taylor, M.G.G.T.; Alexander, C.; Auster, U.; Biele, J.; Finzi, A. Ercoli; Goesmann, F.; Klingehoefer, G.; Kofman, W.; Mottola, S.; Seidenstiker, K.J.; Spohn, T.; Wright, I. (31 July 2015). <a rel="nofollow" class="external text" href="https://doi.org/10.1126%2Fscience.aac5116">"Philae's First Days on the Comet – Introduction to Special Issue"</a>. <i><a href="/wiki/Science_(journal)" title="Science (journal)">Science</a></i>. <b>349</b> (6247): 493. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2015Sci...349..493B">2015Sci...349..493B</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1126%2Fscience.aac5116">10.1126/science.aac5116</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/26228139">26228139</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Science&rft.atitle=Philae%27s+First+Days+on+the+Comet+%E2%80%93+Introduction+to+Special+Issue&rft.volume=349&rft.issue=6247&rft.pages=493&rft.date=2015-07-31&rft_id=info%3Apmid%2F26228139&rft_id=info%3Adoi%2F10.1126%2Fscience.aac5116&rft_id=info%3Abibcode%2F2015Sci...349..493B&rft.aulast=Bibring&rft.aufirst=J.-P.&rft.au=Taylor%2C+M.G.G.T.&rft.au=Alexander%2C+C.&rft.au=Auster%2C+U.&rft.au=Biele%2C+J.&rft.au=Finzi%2C+A.+Ercoli&rft.au=Goesmann%2C+F.&rft.au=Klingehoefer%2C+G.&rft.au=Kofman%2C+W.&rft.au=Mottola%2C+S.&rft.au=Seidenstiker%2C+K.J.&rft.au=Spohn%2C+T.&rft.au=Wright%2C+I.&rft_id=https%3A%2F%2Fdoi.org%2F10.1126%252Fscience.aac5116&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcetone" class="Z3988"></span></span> </li> </ol></div> <div class="mw-heading mw-heading3"><h3 id="Common_sources">Common sources</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetone&action=edit&section=22" title="Edit section: Common sources"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="Haynes" class="citation book cs1">Haynes, William M., ed. (2016). <i><a href="/wiki/CRC_Handbook_of_Chemistry_and_Physics" title="CRC Handbook of Chemistry and Physics">CRC Handbook of Chemistry and Physics</a></i> (97th ed.). <a href="/wiki/CRC_Press" title="CRC Press">CRC Press</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4987-5429-3" title="Special:BookSources/978-1-4987-5429-3"><bdi>978-1-4987-5429-3</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=CRC+Handbook+of+Chemistry+and+Physics&rft.edition=97th&rft.pub=CRC+Press&rft.date=2016&rft.isbn=978-1-4987-5429-3&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcetone" class="Z3988"></span></li></ul> <div class="mw-heading mw-heading3"><h3 id="Further_reading">Further reading</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetone&action=edit&section=23" title="Edit section: Further reading"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1235681985">.mw-parser-output .side-box{margin:4px 0;box-sizing:border-box;border:1px solid #aaa;font-size:88%;line-height:1.25em;background-color:var(--background-color-interactive-subtle,#f8f9fa);display:flow-root}.mw-parser-output .side-box-abovebelow,.mw-parser-output .side-box-text{padding:0.25em 0.9em}.mw-parser-output .side-box-image{padding:2px 0 2px 0.9em;text-align:center}.mw-parser-output .side-box-imageright{padding:2px 0.9em 2px 0;text-align:center}@media(min-width:500px){.mw-parser-output .side-box-flex{display:flex;align-items:center}.mw-parser-output .side-box-text{flex:1;min-width:0}}@media(min-width:720px){.mw-parser-output .side-box{width:238px}.mw-parser-output .side-box-right{clear:right;float:right;margin-left:1em}.mw-parser-output .side-box-left{margin-right:1em}}</style><style data-mw-deduplicate="TemplateStyles:r1237033735">@media print{body.ns-0 .mw-parser-output .sistersitebox{display:none!important}}@media screen{html.skin-theme-clientpref-night .mw-parser-output .sistersitebox img[src*="Wiktionary-logo-en-v2.svg"]{background-color:white}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .sistersitebox img[src*="Wiktionary-logo-en-v2.svg"]{background-color:white}}</style><div class="side-box side-box-right plainlinks sistersitebox"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"> <div class="side-box-flex"> <div class="side-box-image"><span class="noviewer" typeof="mw:File"><span><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/30px-Commons-logo.svg.png" decoding="async" width="30" height="40" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/45px-Commons-logo.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/59px-Commons-logo.svg.png 2x" data-file-width="1024" data-file-height="1376" /></span></span></div> <div class="side-box-text plainlist">Wikimedia Commons has media related to <span style="font-weight: bold; font-style: italic;"><a href="https://commons.wikimedia.org/wiki/Category:Acetone" class="extiw" title="commons:Category:Acetone">Acetone</a></span>.</div></div> </div> <ul><li><a rel="nofollow" class="external text" href="https://www.ilo.org/dyn/icsc/showcard.display?p_lang=en&p_card_id=0087&p_version=2">International Chemical Safety Card 0087</a></li> <li><a rel="nofollow" class="external text" href="https://www.cdc.gov/niosh/npg/npgd0004.html">NIOSH Pocket Guide to Chemical Hazards</a></li> <li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20200318085127/http://sdsdata.org/244731">Acetone Safety Data Sheet (SDS)</a></li> <li><a rel="nofollow" class="external text" href="http://www.toxnet.nlm.nih.gov/cgi-bin/sis/search/f?./temp/~EQIVt8:1">Hazardous substances databank entry at the national library of medicine</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20181204125919/https://toxnet.nlm.nih.gov/cgi-bin/sis/search/f?.%2Ftemp%2F~EQIVt8%3A1">Archived</a> 2018-12-04 at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a></li> <li><a rel="nofollow" class="external text" href="http://www.inchem.org/documents/sids/sids/67641.pdf">SIDS Initial Assessment Report for Acetone</a> from the <a href="/wiki/Organisation_for_Economic_Co-operation_and_Development" class="mw-redirect" title="Organisation for Economic Co-operation and Development">Organisation for Economic Co-operation and Development</a> (OECD)</li> <li>Calculation of <a rel="nofollow" class="external text" href="http://ddbonline.ddbst.de/AntoineCalculation/AntoineCalculationCGI.exe?component=Acetone">vapor pressure</a>, <a rel="nofollow" class="external text" href="http://ddbonline.ddbst.de/DIPPR105DensityCalculation/DIPPR105CalculationCGI.exe?component=Acetone">liquid density</a>, <a rel="nofollow" class="external text" href="http://ddbonline.ddbst.de/VogelCalculation/VogelCalculationCGI.exe?component=Acetone">dynamic liquid viscosity</a>, <a rel="nofollow" class="external text" href="http://ddbonline.ddbst.de/DIPPR106SFTCalculation/DIPPR106SFTCalculationCGI.exe?component=Acetone">surface tension</a> of acetone</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 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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%">to <a href="/wiki/HMG-CoA" title="HMG-CoA">HMG-CoA</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/Acetyl-CoA" title="Acetyl-CoA">Acetyl-CoA</a></li> <li><a href="/wiki/Acetoacetyl-CoA" title="Acetoacetyl-CoA">Acetoacetyl-CoA</a></li> <li><a href="/wiki/Beta-Hydroxy_beta-methylbutyric_acid" class="mw-redirect" title="Beta-Hydroxy beta-methylbutyric acid">HMB</a></li> <li><a href="/wiki/Beta-Hydroxy_beta-methylbutyryl-CoA" class="mw-redirect" title="Beta-Hydroxy beta-methylbutyryl-CoA">HMB-CoA</a></li> <li><a href="/wiki/HMG-CoA" title="HMG-CoA">HMG-CoA</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Ketone_bodies" title="Ketone bodies">Ketone bodies</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 class="mw-selflink selflink">Acetone</a></li> <li><a href="/wiki/Acetoacetic_acid" title="Acetoacetic acid">Acetoacetic acid</a></li> <li><a href="/wiki/Beta-Hydroxybutyric_acid" class="mw-redirect" title="Beta-Hydroxybutyric acid">β-Hydroxybutyric acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">to <a href="/wiki/Dimethylallyl_pyrophosphate" title="Dimethylallyl pyrophosphate">DMAPP</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/Mevalonic_acid" title="Mevalonic acid">Mevalonic acid</a></li> <li><a href="/wiki/Phosphomevalonic_acid" title="Phosphomevalonic acid">Phosphomevalonic acid</a></li> <li><a href="/wiki/5-Diphosphomevalonic_acid" title="5-Diphosphomevalonic acid">5-Diphosphomevalonic acid</a></li> <li><a href="/wiki/Isopentenyl_pyrophosphate" title="Isopentenyl pyrophosphate">Isopentenyl pyrophosphate</a></li> <li><a href="/wiki/Dimethylallyl_pyrophosphate" title="Dimethylallyl pyrophosphate">Dimethylallyl pyrophosphate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Geranyl-</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/Geranyl_pyrophosphate" title="Geranyl pyrophosphate">Geranyl pyrophosphate</a></li> <li><a href="/wiki/Geranylgeranyl_pyrophosphate" title="Geranylgeranyl pyrophosphate">Geranylgeranyl pyrophosphate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Carotenoid" title="Carotenoid">Carotenoid</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/Prephytoene_diphosphate" title="Prephytoene diphosphate">Prephytoene diphosphate</a></li> <li><a href="/wiki/Phytoene" title="Phytoene">Phytoene</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/Non-mevalonate_pathway" title="Non-mevalonate pathway">Non-mevalonate pathway</a></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><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/1-Deoxy-D-xylulose_5-phosphate" title="1-Deoxy-D-xylulose 5-phosphate">DOXP</a></li> <li><a href="/wiki/2-C-methylerythritol_4-phosphate" class="mw-redirect" title="2-C-methylerythritol 4-phosphate">MEP</a></li> <li><a href="/wiki/4-diphosphocytidyl-2-C-methylerythritol" class="mw-redirect" title="4-diphosphocytidyl-2-C-methylerythritol">CDP-ME</a></li> <li><a href="/wiki/4-diphosphocytidyl-2-C-methyl-D-erythritol_2-phosphate" class="mw-redirect" title="4-diphosphocytidyl-2-C-methyl-D-erythritol 2-phosphate">CDP-MEP</a></li> <li><a href="/wiki/2-C-methyl-D-erythritol_2,4-cyclopyrophosphate" class="mw-redirect" title="2-C-methyl-D-erythritol 2,4-cyclopyrophosphate">MEcPP</a></li> <li><a href="/wiki/(E)-4-Hydroxy-3-methyl-but-2-enyl_pyrophosphate" title="(E)-4-Hydroxy-3-methyl-but-2-enyl pyrophosphate">HMB-PP</a></li> <li><a href="/wiki/Isopentenyl_pyrophosphate" title="Isopentenyl pyrophosphate">IPP</a></li> <li><a href="/wiki/Dimethylallyl_pyrophosphate" title="Dimethylallyl pyrophosphate">DMAPP</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">To <a href="/wiki/Cholesterol" title="Cholesterol">Cholesterol</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Farnesyl_pyrophosphate" title="Farnesyl pyrophosphate">Farnesyl pyrophosphate</a></li> <li><a href="/wiki/Squalene" title="Squalene">Squalene</a></li> <li><a href="/wiki/2,3-Oxidosqualene" title="2,3-Oxidosqualene">2,3-Oxidosqualene</a></li> <li><a href="/wiki/Lanosterol" title="Lanosterol">Lanosterol</a></li></ul> <ul><li><a href="/wiki/Lanosterol" title="Lanosterol">Lanosterol</a></li> <li><a href="/w/index.php?title=14-demethyllanosterol&action=edit&redlink=1" class="new" title="14-demethyllanosterol (page does not exist)">14-demethyllanosterol</a></li> <li><a href="/w/index.php?title=4alpha-Methylzymosterol&action=edit&redlink=1" class="new" title="4alpha-Methylzymosterol (page does not exist)">4alpha-Methylzymosterol</a></li> <li><a href="/w/index.php?title=Zymosterone&action=edit&redlink=1" class="new" title="Zymosterone (page does not exist)">Zymosterone</a></li> <li><a href="/wiki/Zymosterol" title="Zymosterol">Zymosterol</a></li></ul> <ul><li><a href="/wiki/Zymosterol" title="Zymosterol">Zymosterol</a></li> <li><a href="/w/index.php?title=Zymostenol&action=edit&redlink=1" class="new" title="Zymostenol (page does not exist)">Zymostenol</a></li> <li><a href="/wiki/Lathosterol" title="Lathosterol">Lathosterol</a></li> <li><a href="/wiki/7-Dehydrocholesterol" title="7-Dehydrocholesterol">7-Dehydrocholesterol</a></li> <li><a href="/wiki/Cholesterol" title="Cholesterol">Cholesterol</a></li></ul> <ul><li><a href="/wiki/Zymosterol" title="Zymosterol">Zymosterol</a></li> <li><a href="/w/index.php?title=Cholesta-7,24-dien-3-ol&action=edit&redlink=1" class="new" title="Cholesta-7,24-dien-3-ol (page does not exist)">Cholesta-7,24-dien-3-ol</a></li> <li><a href="/wiki/7-Dehydrodesmosterol" title="7-Dehydrodesmosterol">7-Dehydrodesmosterol</a></li> <li><a href="/wiki/Desmosterol" title="Desmosterol">Desmosterol</a></li> <li><a href="/wiki/Cholesterol" title="Cholesterol">Cholesterol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">From <a href="/wiki/Cholesterol" title="Cholesterol">Cholesterol</a> <br />to <a href="/wiki/Steroid" title="Steroid">Steroid hormones</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/22R-Hydroxycholesterol" title="22R-Hydroxycholesterol">22<i>R</i>-Hydroxycholesterol</a></li> <li><a href="/wiki/20%CE%B1,22R-Dihydroxycholesterol" title="20α,22R-Dihydroxycholesterol">20α,22<i>R</i>-Dihydroxycholesterol</a></li> <li>See <a href="/wiki/Template:Steroid_hormones" title="Template:Steroid hormones">here</a> instead.</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Nonhuman</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%">To <a href="/wiki/Sitosterol" class="mw-redirect" title="Sitosterol">Sitosterol</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/Cycloartenol" title="Cycloartenol">Cycloartenol</a></li> <li><a href="/w/index.php?title=Cycloeucalenol&action=edit&redlink=1" class="new" title="Cycloeucalenol (page does not exist)">Cycloeucalenol</a></li> <li><a href="/wiki/Obtusifoliol" title="Obtusifoliol">Obtusifoliol</a></li> <li><a href="/wiki/4%CE%B1-methylfecosterol" class="mw-redirect" title="4α-methylfecosterol">4α-methylfecosterol</a></li> <li><a href="/wiki/Isofucosterol" title="Isofucosterol">Isofucosterol</a></li> <li><a href="/wiki/24-Methylenelophenol" title="24-Methylenelophenol">24-Methylenelophenol</a></li> <li><a href="/wiki/Sitosterol" class="mw-redirect" title="Sitosterol">Sitosterol</a></li> <li>More <a href="/wiki/Phytosterol" title="Phytosterol">Phytosterols</a> see <a href="/wiki/Template:Steroid_hormones" title="Template:Steroid hormones">here</a> instead.</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">To <a href="/wiki/Ergocalciferol" title="Ergocalciferol">Ergocalciferol</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/Fecosterol" title="Fecosterol">Fecosterol</a></li> <li><a href="/wiki/Episterol" title="Episterol">Episterol</a></li> <li><a href="/wiki/Ergostatrienol" class="mw-redirect" title="Ergostatrienol">Ergostatrienol</a></li> <li><a href="/w/index.php?title=Ergostatetraenol&action=edit&redlink=1" class="new" title="Ergostatetraenol (page does not exist)">Ergostatetraenol</a></li> <li><a href="/wiki/Ergosterol" title="Ergosterol">Ergosterol</a></li> <li><a href="/wiki/Ergocalciferol" title="Ergocalciferol">Ergocalciferol</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="GABAA_receptor_positive_modulators" 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:GABAA_receptor_positive_modulators" title="Template:GABAA receptor positive modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:GABAA_receptor_positive_modulators" title="Template talk:GABAA receptor positive modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:GABAA_receptor_positive_modulators" title="Special:EditPage/Template:GABAA receptor positive modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="GABAA_receptor_positive_modulators" style="font-size:114%;margin:0 4em"><a href="/wiki/GABAA_receptor_positive_allosteric_modulator" title="GABAA receptor positive allosteric modulator"><abbr title="γ-Aminobutyric acid">GABA</abbr><sub>A</sub> receptor positive modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">Alcohols</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=Brometone&action=edit&redlink=1" class="new" title="Brometone (page does not exist)">Brometone</a></li> <li><a href="/wiki/1-Butanol" title="1-Butanol">Butanol</a></li> <li><a href="/wiki/Chloralodol" title="Chloralodol">Chloralodol</a></li> <li><a href="/wiki/Chlorobutanol" title="Chlorobutanol">Chlorobutanol (cloretone)</a></li> <li><a href="/wiki/Alcohol_(drug)" title="Alcohol (drug)">Ethanol (alcohol)</a> (<a href="/wiki/Alcoholic_drink" class="mw-redirect" title="Alcoholic drink">alcoholic drink</a>)</li> <li><a href="/wiki/Ethchlorvynol" title="Ethchlorvynol">Ethchlorvynol</a></li> <li><a href="/wiki/Isobutanol" title="Isobutanol">Isobutanol</a></li> <li><a href="/wiki/Isopropanol" class="mw-redirect" title="Isopropanol">Isopropanol</a></li> <li><a href="/wiki/Menthol" title="Menthol">Menthol</a></li> <li><a href="/wiki/Methanol" title="Methanol">Methanol</a></li> <li><a href="/wiki/Methylpentynol" title="Methylpentynol">Methylpentynol</a></li> <li><a href="/wiki/1-Pentanol" title="1-Pentanol">Pentanol</a></li> <li><a href="/wiki/Petrichloral" title="Petrichloral">Petrichloral</a></li> <li><a href="/wiki/1-Propanol" title="1-Propanol">Propanol</a></li> <li><a href="/wiki/Tert-Butanol" class="mw-redirect" title="Tert-Butanol"><i>tert</i>-Butanol (2M2P)</a></li> <li><a href="/wiki/Tert-Pentanol" class="mw-redirect" title="Tert-Pentanol"><i>tert</i>-Pentanol (2M2B)</a></li> <li><a href="/wiki/Tribromoethanol" title="Tribromoethanol">Tribromoethanol</a></li> <li><a href="/wiki/Trichloroethanol" class="mw-redirect" title="Trichloroethanol">Trichloroethanol</a></li> <li><a href="/wiki/Triclofos" title="Triclofos">Triclofos</a></li> <li><a href="/wiki/Trifluoroethanol" class="mw-redirect" title="Trifluoroethanol">Trifluoroethanol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Barbiturate" title="Barbiturate">Barbiturates</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/(-)-5-(1,3-Dimethylbutyl)-5-ethylbarbituric_acid" class="mw-redirect" title="(-)-5-(1,3-Dimethylbutyl)-5-ethylbarbituric acid">(-)-DMBB</a></li> <li><a href="/wiki/Allobarbital" title="Allobarbital">Allobarbital</a></li> <li><a href="/wiki/Alphenal" title="Alphenal">Alphenal</a></li> <li><a href="/wiki/Amobarbital" title="Amobarbital">Amobarbital</a></li> <li><a href="/wiki/Aprobarbital" title="Aprobarbital">Aprobarbital</a></li> <li><a href="/wiki/Barbexaclone" title="Barbexaclone">Barbexaclone</a></li> <li><a href="/wiki/Barbital" title="Barbital">Barbital</a></li> <li><a href="/wiki/Benzobarbital" title="Benzobarbital">Benzobarbital</a></li> <li><a href="/wiki/Benzylbutylbarbiturate" title="Benzylbutylbarbiturate">Benzylbutylbarbiturate</a></li> <li><a href="/wiki/Brallobarbital" title="Brallobarbital">Brallobarbital</a></li> <li><a href="/wiki/Brophebarbital" title="Brophebarbital">Brophebarbital</a></li> <li><a href="/wiki/Butabarbital" title="Butabarbital">Butabarbital/Secbutabarbital</a></li> <li><a href="/wiki/Butalbital" title="Butalbital">Butalbital</a></li> <li><a href="/wiki/Buthalital" title="Buthalital">Buthalital</a></li> <li><a href="/wiki/Butobarbital" title="Butobarbital">Butobarbital</a></li> <li><a href="/wiki/Butallylonal" title="Butallylonal">Butallylonal</a></li> <li><a href="/wiki/Carbubarb" title="Carbubarb">Carbubarb</a></li> <li><a href="/wiki/Crotylbarbital" title="Crotylbarbital">Crotylbarbital</a></li> <li><a href="/wiki/Cyclobarbital" title="Cyclobarbital">Cyclobarbital</a></li> <li><a href="/wiki/Cyclopentobarbital" title="Cyclopentobarbital">Cyclopentobarbital</a></li> <li><a href="/wiki/Difebarbamate" title="Difebarbamate">Difebarbamate</a></li> <li><a href="/wiki/Enallylpropymal" title="Enallylpropymal">Enallylpropymal</a></li> <li><a href="/wiki/Ethallobarbital" title="Ethallobarbital">Ethallobarbital</a></li> <li><a href="/wiki/Eterobarb" title="Eterobarb">Eterobarb</a></li> <li><a href="/wiki/Febarbamate" title="Febarbamate">Febarbamate</a></li> <li><a href="/wiki/Heptabarb" title="Heptabarb">Heptabarb</a></li> <li><a href="/wiki/Heptobarbital" title="Heptobarbital">Heptobarbital</a></li> <li><a href="/wiki/Hexethal" title="Hexethal">Hexethal</a></li> <li><a href="/wiki/Hexobarbital" title="Hexobarbital">Hexobarbital</a></li> <li><a href="/wiki/Metharbital" title="Metharbital">Metharbital</a></li> <li><a href="/wiki/Methitural" title="Methitural">Methitural</a></li> <li><a href="/wiki/Methohexital" title="Methohexital">Methohexital</a></li> <li><a href="/wiki/Methylphenobarbital" title="Methylphenobarbital">Methylphenobarbital</a></li> <li><a href="/wiki/Narcobarbital" title="Narcobarbital">Narcobarbital</a></li> <li><a href="/wiki/Nealbarbital" title="Nealbarbital">Nealbarbital</a></li> <li><a href="/wiki/Pentobarbital" title="Pentobarbital">Pentobarbital</a></li> <li><a href="/wiki/Phenallymal" class="mw-redirect" title="Phenallymal">Phenallymal</a></li> <li><a href="/wiki/Phenobarbital" title="Phenobarbital">Phenobarbital</a></li> <li><a href="/wiki/Phetharbital" title="Phetharbital">Phetharbital</a></li> <li><a href="/wiki/Primidone" title="Primidone">Primidone</a></li> <li><a href="/wiki/Probarbital" title="Probarbital">Probarbital</a></li> <li><a href="/wiki/Propallylonal" title="Propallylonal">Propallylonal</a></li> <li><a href="/wiki/Propylbarbital" title="Propylbarbital">Propylbarbital</a></li> <li><a href="/wiki/Proxibarbital" title="Proxibarbital">Proxibarbital</a></li> <li><a href="/wiki/Reposal" title="Reposal">Reposal</a></li> <li><a href="/wiki/Secobarbital" title="Secobarbital">Secobarbital</a></li> <li><a href="/wiki/Sigmodal" title="Sigmodal">Sigmodal</a></li> <li><a href="/wiki/Spirobarbital" title="Spirobarbital">Spirobarbital</a></li> <li><a href="/wiki/Talbutal" title="Talbutal">Talbutal</a></li> <li><a href="/wiki/Tetrabamate" title="Tetrabamate">Tetrabamate</a></li> <li><a href="/wiki/Tetrabarbital" title="Tetrabarbital">Tetrabarbital</a></li> <li><a href="/wiki/Thialbarbital" title="Thialbarbital">Thialbarbital</a></li> <li><a href="/wiki/Thiamylal" title="Thiamylal">Thiamylal</a></li> <li><a href="/wiki/Thiobarbital" title="Thiobarbital">Thiobarbital</a></li> <li><a href="/wiki/Thiobutabarbital" title="Thiobutabarbital">Thiobutabarbital</a></li> <li><a href="/wiki/Sodium_thiopental" title="Sodium thiopental">Thiopental</a></li> <li><a href="/wiki/Thiotetrabarbital" title="Thiotetrabarbital">Thiotetrabarbital</a></li> <li><a href="/wiki/Valofane" title="Valofane">Valofane</a></li> <li><a href="/wiki/Vinbarbital" title="Vinbarbital">Vinbarbital</a></li> <li><a href="/wiki/Vinylbital" title="Vinylbital">Vinylbital</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Benzodiazepine" title="Benzodiazepine">Benzodiazepines</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2-Oxoquazepam" title="2-Oxoquazepam">2-Oxoquazepam</a></li> <li><a href="/wiki/3-Hydroxyphenazepam" title="3-Hydroxyphenazepam">3-Hydroxyphenazepam</a></li> <li><a href="/wiki/Adinazolam" title="Adinazolam">Adinazolam</a></li> <li><a href="/wiki/Alprazolam" title="Alprazolam">Alprazolam</a></li> <li><a href="/wiki/Arfendazam" title="Arfendazam">Arfendazam</a></li> <li><a href="/wiki/Avizafone" title="Avizafone">Avizafone</a></li> <li><a href="/wiki/Bentazepam" title="Bentazepam">Bentazepam</a></li> <li><a href="/wiki/Bretazenil" title="Bretazenil">Bretazenil</a></li> <li><a href="/wiki/Bromazepam" title="Bromazepam">Bromazepam</a></li> <li><a href="/wiki/Bromazolam" title="Bromazolam">Bromazolam</a></li> <li><a href="/wiki/Brotizolam" title="Brotizolam">Brotizolam</a></li> <li><a href="/wiki/Camazepam" title="Camazepam">Camazepam</a></li> <li><a href="/wiki/Carburazepam" title="Carburazepam">Carburazepam</a></li> <li><a href="/wiki/Chlordiazepoxide" title="Chlordiazepoxide">Chlordiazepoxide</a></li> <li><a href="/wiki/Ciclotizolam" title="Ciclotizolam">Ciclotizolam</a></li> <li><a href="/wiki/Cinazepam" title="Cinazepam">Cinazepam</a></li> <li><a href="/wiki/Cinolazepam" title="Cinolazepam">Cinolazepam</a></li> <li><a href="/wiki/Clazolam" title="Clazolam">Clazolam</a></li> <li><a href="/wiki/Climazolam" title="Climazolam">Climazolam</a></li> <li><a href="/wiki/Clobazam" title="Clobazam">Clobazam</a></li> <li><a href="/wiki/Clonazepam" title="Clonazepam">Clonazepam</a></li> <li><a href="/wiki/Clonazolam" title="Clonazolam">Clonazolam</a></li> <li><a href="/wiki/Cloniprazepam" title="Cloniprazepam">Cloniprazepam</a></li> <li><a href="/wiki/Clorazepate" title="Clorazepate">Clorazepate</a></li> <li><a href="/wiki/Clotiazepam" title="Clotiazepam">Clotiazepam</a></li> <li><a href="/wiki/Cloxazolam" title="Cloxazolam">Cloxazolam</a></li> <li><a href="/wiki/CP-1414S" title="CP-1414S">CP-1414S</a></li> <li><a href="/wiki/Cyprazepam" title="Cyprazepam">Cyprazepam</a></li> <li><a href="/wiki/Delorazepam" title="Delorazepam">Delorazepam</a></li> <li><a href="/wiki/Demoxepam" title="Demoxepam">Demoxepam</a></li> <li><a href="/wiki/Diazepam" title="Diazepam">Diazepam</a></li> <li><a href="/wiki/Diclazepam" title="Diclazepam">Diclazepam</a></li> <li><a href="/wiki/Dimdazenil" title="Dimdazenil">Dimdazenil</a></li> <li><a href="/wiki/Doxefazepam" title="Doxefazepam">Doxefazepam</a></li> <li><a href="/wiki/Elfazepam" title="Elfazepam">Elfazepam</a></li> <li><a href="/wiki/Estazolam" title="Estazolam">Estazolam</a></li> <li><a href="/wiki/Ethyl_carfluzepate" title="Ethyl carfluzepate">Ethyl carfluzepate</a></li> <li><a href="/wiki/Ethyl_dirazepate" title="Ethyl dirazepate">Ethyl dirazepate</a></li> <li><a href="/wiki/Ethyl_loflazepate" title="Ethyl loflazepate">Ethyl loflazepate</a></li> <li><a href="/wiki/Etizolam" title="Etizolam">Etizolam</a></li> <li><a href="/wiki/FG-8205" title="FG-8205">FG-8205</a></li> <li><a href="/wiki/Fletazepam" title="Fletazepam">Fletazepam</a></li> <li><a href="/wiki/Flubromazepam" title="Flubromazepam">Flubromazepam</a></li> <li><a href="/wiki/Flubromazolam" title="Flubromazolam">Flubromazolam</a></li> <li><a href="/wiki/Fludiazepam" title="Fludiazepam">Fludiazepam</a></li> <li><a href="/wiki/Flunitrazepam" title="Flunitrazepam">Flunitrazepam</a></li> <li><a href="/wiki/Flunitrazolam" title="Flunitrazolam">Flunitrazolam</a></li> <li><a href="/wiki/Flurazepam" title="Flurazepam">Flurazepam</a></li> <li><a href="/wiki/Flutazolam" title="Flutazolam">Flutazolam</a></li> <li><a href="/wiki/Flutemazepam" title="Flutemazepam">Flutemazepam</a></li> <li><a href="/wiki/Flutoprazepam" title="Flutoprazepam">Flutoprazepam</a></li> <li><a href="/wiki/Fosazepam" title="Fosazepam">Fosazepam</a></li> <li><a href="/wiki/Gidazepam" title="Gidazepam">Gidazepam</a></li> <li><a href="/wiki/Halazepam" title="Halazepam">Halazepam</a></li> <li><a href="/wiki/Haloxazolam" title="Haloxazolam">Haloxazolam</a></li> <li><a href="/wiki/Iclazepam" title="Iclazepam">Iclazepam</a></li> <li><a href="/wiki/Imidazenil" title="Imidazenil">Imidazenil</a></li> <li><a href="/wiki/Irazepine" title="Irazepine">Irazepine</a></li> <li><a href="/wiki/Ketazolam" title="Ketazolam">Ketazolam</a></li> <li><a href="/wiki/Lofendazam" title="Lofendazam">Lofendazam</a></li> <li><a href="/wiki/Lopirazepam" title="Lopirazepam">Lopirazepam</a></li> <li><a href="/wiki/Loprazolam" title="Loprazolam">Loprazolam</a></li> <li><a href="/wiki/Lorazepam" title="Lorazepam">Lorazepam</a></li> <li><a href="/wiki/Lormetazepam" title="Lormetazepam">Lormetazepam</a></li> <li><a href="/wiki/Meclonazepam" title="Meclonazepam">Meclonazepam</a></li> <li><a href="/wiki/Medazepam" title="Medazepam">Medazepam</a></li> <li><a href="/wiki/Menitrazepam" title="Menitrazepam">Menitrazepam</a></li> <li><a href="/wiki/Metaclazepam" title="Metaclazepam">Metaclazepam</a></li> <li><a href="/wiki/Mexazolam" title="Mexazolam">Mexazolam</a></li> <li><a href="/wiki/Midazolam" title="Midazolam">Midazolam</a></li> <li><a href="/wiki/Motrazepam" title="Motrazepam">Motrazepam</a></li> <li><a href="/wiki/N-Desalkylflurazepam" title="N-Desalkylflurazepam">N-Desalkylflurazepam</a></li> <li><a href="/wiki/Nifoxipam" title="Nifoxipam">Nifoxipam</a></li> <li><a href="/wiki/Nimetazepam" title="Nimetazepam">Nimetazepam</a></li> <li><a href="/wiki/Nitrazepam" title="Nitrazepam">Nitrazepam</a></li> <li><a href="/wiki/Nitrazepate" title="Nitrazepate">Nitrazepate</a></li> <li><a href="/wiki/Nitrazolam" title="Nitrazolam">Nitrazolam</a></li> <li><a href="/wiki/Nordazepam" title="Nordazepam">Nordazepam</a></li> <li><a href="/wiki/Nortetrazepam" title="Nortetrazepam">Nortetrazepam</a></li> <li><a href="/wiki/Oxazepam" title="Oxazepam">Oxazepam</a></li> <li><a href="/wiki/Oxazolam" title="Oxazolam">Oxazolam</a></li> <li><a href="/wiki/Phenazepam" title="Phenazepam">Phenazepam</a></li> <li><a href="/wiki/Pinazepam" title="Pinazepam">Pinazepam</a></li> <li><a href="/wiki/Pivoxazepam" title="Pivoxazepam">Pivoxazepam</a></li> <li><a href="/wiki/Prazepam" title="Prazepam">Prazepam</a></li> <li><a href="/wiki/Premazepam" title="Premazepam">Premazepam</a></li> <li><a href="/wiki/Proflazepam" title="Proflazepam">Proflazepam</a></li> <li><a href="/wiki/Pyrazolam" title="Pyrazolam">Pyrazolam</a></li> <li><a href="/wiki/QH-II-66" title="QH-II-66">QH-II-66</a></li> <li><a href="/wiki/Quazepam" title="Quazepam">Quazepam</a></li> <li><a href="/wiki/Reclazepam" title="Reclazepam">Reclazepam</a></li> <li><a href="/wiki/Remimazolam" title="Remimazolam">Remimazolam</a></li> <li><a href="/wiki/Rilmazafone" title="Rilmazafone">Rilmazafone</a></li> <li><a href="/wiki/Ripazepam" title="Ripazepam">Ripazepam</a></li> <li><a href="/wiki/Ro48-6791" title="Ro48-6791">Ro48-6791</a></li> <li><a href="/wiki/Ro48-8684" title="Ro48-8684">Ro48-8684</a></li> <li><a href="/wiki/SH-053-R-CH3-2%E2%80%B2F" title="SH-053-R-CH3-2′F">SH-053-R-CH3-2′F</a></li> <li><a href="/wiki/Sulazepam" title="Sulazepam">Sulazepam</a></li> <li><a href="/wiki/Temazepam" title="Temazepam">Temazepam</a></li> <li><a href="/wiki/Tetrazepam" title="Tetrazepam">Tetrazepam</a></li> <li><a href="/wiki/Tolufazepam" class="mw-redirect" title="Tolufazepam">Tolufazepam</a></li> <li><a href="/wiki/Triazolam" title="Triazolam">Triazolam</a></li> <li><a href="/wiki/Triflubazam" title="Triflubazam">Triflubazam</a></li> <li><a href="/wiki/Triflunordazepam" title="Triflunordazepam">Triflunordazepam (Ro5-2904)</a></li> <li><a href="/wiki/Tuclazepam" title="Tuclazepam">Tuclazepam</a></li> <li><a href="/wiki/Uldazepam" title="Uldazepam">Uldazepam</a></li> <li><a href="/wiki/Zapizolam" title="Zapizolam">Zapizolam</a></li> <li><a href="/wiki/Zolazepam" title="Zolazepam">Zolazepam</a></li> <li><a href="/wiki/Zomebazam" title="Zomebazam">Zomebazam</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Carbamate" title="Carbamate">Carbamates</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Carisbamate" title="Carisbamate">Carisbamate</a></li> <li><a href="/wiki/Carisoprodol" title="Carisoprodol">Carisoprodol</a></li> <li><a href="/wiki/Clocental" title="Clocental">Clocental</a></li> <li><a href="/wiki/Cyclarbamate" title="Cyclarbamate">Cyclarbamate</a></li> <li><a href="/wiki/Difebarbamate" title="Difebarbamate">Difebarbamate</a></li> <li><a href="/wiki/Emylcamate" title="Emylcamate">Emylcamate</a></li> <li><a href="/wiki/Ethinamate" title="Ethinamate">Ethinamate</a></li> <li><a href="/wiki/Febarbamate" title="Febarbamate">Febarbamate</a></li> <li><a href="/wiki/Felbamate" title="Felbamate">Felbamate</a></li> <li><a href="/wiki/Hexapropymate" title="Hexapropymate">Hexapropymate</a></li> <li><a href="/wiki/Hydroxyphenamate" title="Hydroxyphenamate">Hydroxyphenamate</a></li> <li><a href="/wiki/Lorbamate" title="Lorbamate">Lorbamate</a></li> <li><a href="/wiki/Mebutamate" title="Mebutamate">Mebutamate</a></li> <li><a href="/wiki/Meprobamate" title="Meprobamate">Meprobamate</a></li> <li><a href="/wiki/Nisobamate" title="Nisobamate">Nisobamate</a></li> <li><a href="/wiki/Pentabamate" title="Pentabamate">Pentabamate</a></li> <li><a href="/wiki/Phenprobamate" title="Phenprobamate">Phenprobamate</a></li> <li><a href="/wiki/Procymate" title="Procymate">Procymate</a></li> <li><a href="/wiki/Styramate" title="Styramate">Styramate</a></li> <li><a href="/wiki/Tetrabamate" title="Tetrabamate">Tetrabamate</a></li> <li><a href="/wiki/Tybamate" title="Tybamate">Tybamate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Flavonoid" title="Flavonoid">Flavonoids</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/6-Methylapigenin" title="6-Methylapigenin">6-Methylapigenin</a></li> <li><a href="/wiki/Ampelopsin" title="Ampelopsin">Ampelopsin (dihydromyricetin)</a></li> <li><a href="/wiki/Apigenin" title="Apigenin">Apigenin</a></li> <li><a href="/wiki/Baicalein" title="Baicalein">Baicalein</a></li> <li><a href="/wiki/Baicalin" title="Baicalin">Baicalin</a></li> <li><a href="/wiki/Catechin" title="Catechin">Catechin</a></li> <li><a href="/wiki/Epigallocatechin" class="mw-redirect" title="Epigallocatechin">EGC</a></li> <li><a href="/wiki/Epigallocatechin_gallate" title="Epigallocatechin gallate">EGCG</a></li> <li><a href="/wiki/Hispidulin" title="Hispidulin">Hispidulin</a></li> <li><a href="/w/index.php?title=Linarin&action=edit&redlink=1" class="new" title="Linarin (page does not exist)">Linarin</a></li> <li><a href="/wiki/Luteolin" title="Luteolin">Luteolin</a></li> <li><a href="/w/index.php?title=Trans-6,4%E2%80%B2-dimethoxyretrochalcone&action=edit&redlink=1" class="new" title="Trans-6,4′-dimethoxyretrochalcone (page does not exist)">Rc-OMe</a></li> <li><a href="/wiki/Scutellaria" title="Scutellaria">Skullcap</a> constituents (e.g., <a href="/wiki/Baicalin" title="Baicalin">baicalin</a>)</li> <li><a href="/wiki/Wogonin" title="Wogonin">Wogonin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Imidazole" title="Imidazole">Imidazoles</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Etomidate" title="Etomidate">Etomidate</a></li> <li><a href="/wiki/Metomidate" title="Metomidate">Metomidate</a></li> <li><a href="/wiki/Propoxate" title="Propoxate">Propoxate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Kava" title="Kava">Kava</a> constituents</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=10-Methoxyyangonin&action=edit&redlink=1" class="new" title="10-Methoxyyangonin (page does not exist)">10-Methoxyyangonin</a></li> <li><a href="/w/index.php?title=11-Methoxyyangonin&action=edit&redlink=1" class="new" title="11-Methoxyyangonin (page does not exist)">11-Methoxyyangonin</a></li> <li><a href="/w/index.php?title=11-Hydroxyyangonin&action=edit&redlink=1" class="new" title="11-Hydroxyyangonin (page does not exist)">11-Hydroxyyangonin</a></li> <li><a href="/wiki/Desmethoxyyangonin" title="Desmethoxyyangonin">Desmethoxyyangonin</a></li> <li><a href="/w/index.php?title=11-Methoxy-12-hydroxydehydrokavain&action=edit&redlink=1" class="new" title="11-Methoxy-12-hydroxydehydrokavain (page does not exist)">11-Methoxy-12-hydroxydehydrokavain</a></li> <li><a href="/w/index.php?title=7,8-Dihydroyangonin&action=edit&redlink=1" class="new" title="7,8-Dihydroyangonin (page does not exist)">7,8-Dihydroyangonin</a></li> <li><a href="/wiki/Kavain" title="Kavain">Kavain</a></li> <li><a href="/w/index.php?title=5-Hydroxykavain&action=edit&redlink=1" class="new" title="5-Hydroxykavain (page does not exist)">5-Hydroxykavain</a></li> <li><a href="/w/index.php?title=5,6-Dihydroyangonin&action=edit&redlink=1" class="new" title="5,6-Dihydroyangonin (page does not exist)">5,6-Dihydroyangonin</a></li> <li><a href="/w/index.php?title=7,8-Dihydrokavain&action=edit&redlink=1" class="new" title="7,8-Dihydrokavain (page does not exist)">7,8-Dihydrokavain</a></li> <li><a href="/w/index.php?title=5,6,7,8-Tetrahydroyangonin&action=edit&redlink=1" class="new" title="5,6,7,8-Tetrahydroyangonin (page does not exist)">5,6,7,8-Tetrahydroyangonin</a></li> <li><a href="/w/index.php?title=5,6-Dehydromethysticin&action=edit&redlink=1" class="new" title="5,6-Dehydromethysticin (page does not exist)">5,6-Dehydromethysticin</a></li> <li><a href="/wiki/Methysticin" title="Methysticin">Methysticin</a></li> <li><a href="/w/index.php?title=7,8-Dihydromethysticin&action=edit&redlink=1" class="new" title="7,8-Dihydromethysticin (page does not exist)">7,8-Dihydromethysticin</a></li> <li><a href="/wiki/Yangonin" title="Yangonin">Yangonin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Monoureide" class="mw-redirect" title="Monoureide">Monoureides</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acecarbromal" title="Acecarbromal">Acecarbromal</a></li> <li><a href="/wiki/Apronal" title="Apronal">Apronal (apronalide)</a></li> <li><a href="/wiki/Bromisoval" title="Bromisoval">Bromisoval</a></li> <li><a href="/wiki/Carbromal" title="Carbromal">Carbromal</a></li> <li><a href="/w/index.php?title=Capuride&action=edit&redlink=1" class="new" title="Capuride (page does not exist)">Capuride</a></li> <li><a href="/w/index.php?title=Ectylurea&action=edit&redlink=1" class="new" title="Ectylurea (page does not exist)">Ectylurea</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Neuroactive_steroid" class="mw-redirect" title="Neuroactive steroid">Neuroactive steroids</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acebrochol" title="Acebrochol">Acebrochol</a></li> <li><a href="/wiki/Allopregnanolone" title="Allopregnanolone">Allopregnanolone (brexanolone)</a></li> <li><a href="/wiki/Alfadolone" title="Alfadolone">Alfadolone</a></li> <li><a href="/wiki/Alfaxalone" title="Alfaxalone">Alfaxalone</a></li> <li><a href="/wiki/3%CE%B1-Androstanediol" title="3α-Androstanediol">3α-Androstanediol</a></li> <li><a href="/wiki/Androstenol" title="Androstenol">Androstenol</a></li> <li><a href="/wiki/Androsterone" title="Androsterone">Androsterone</a></li> <li>Certain <a href="/wiki/Anabolic-androgenic_steroid" class="mw-redirect" title="Anabolic-androgenic steroid">anabolic-androgenic steroids</a></li> <li><a href="/wiki/Cholesterol" title="Cholesterol">Cholesterol</a></li> <li><a href="/wiki/Dihydrodeoxycorticosterone" title="Dihydrodeoxycorticosterone">DHDOC</a></li> <li><a href="/wiki/3%CE%B1-Dihydroprogesterone" title="3α-Dihydroprogesterone">3α-DHP</a></li> <li><a href="/wiki/5%CE%B1-Dihydroprogesterone" title="5α-Dihydroprogesterone">5α-DHP</a></li> <li><a href="/wiki/5%CE%B2-Dihydroprogesterone" title="5β-Dihydroprogesterone">5β-DHP</a></li> <li><a href="/wiki/Dihydrotestosterone" title="Dihydrotestosterone">DHT</a></li> <li><a href="/wiki/Etiocholanolone" title="Etiocholanolone">Etiocholanolone</a></li> <li><a href="/wiki/Ganaxolone" title="Ganaxolone">Ganaxolone</a></li> <li><a href="/wiki/Hydroxydione" title="Hydroxydione">Hydroxydione</a></li> <li><a href="/wiki/Minaxolone" title="Minaxolone">Minaxolone</a></li> <li><a href="/wiki/ORG-20599" title="ORG-20599">ORG-20599</a></li> <li><a href="/wiki/ORG-21465" title="ORG-21465">ORG-21465</a></li> <li><a href="/wiki/P1-185" title="P1-185">P1-185</a></li> <li><a href="/wiki/Posovolone" title="Posovolone">Posovolone</a></li> <li><a href="/wiki/Pregnanolone" title="Pregnanolone">Pregnanolone (eltanolone)</a></li> <li><a href="/wiki/Progesterone" title="Progesterone">Progesterone</a></li> <li><a href="/wiki/Renanolone" title="Renanolone">Renanolone</a></li> <li><a href="/w/index.php?title=SAGE-105&action=edit&redlink=1" class="new" title="SAGE-105 (page does not exist)">SAGE-105</a></li> <li><a href="/wiki/SAGE-324" title="SAGE-324">SAGE-324</a></li> <li><a href="/w/index.php?title=SAGE-516&action=edit&redlink=1" class="new" title="SAGE-516 (page does not exist)">SAGE-516</a></li> <li><a href="/w/index.php?title=SAGE-689&action=edit&redlink=1" class="new" title="SAGE-689 (page does not exist)">SAGE-689</a></li> <li><a href="/w/index.php?title=SAGE-872&action=edit&redlink=1" class="new" title="SAGE-872 (page does not exist)">SAGE-872</a></li> <li><a href="/wiki/Testosterone" title="Testosterone">Testosterone</a></li> <li><a href="/wiki/Tetrahydrodeoxycorticosterone" title="Tetrahydrodeoxycorticosterone">THDOC</a></li> <li><a href="/wiki/Zuranolone" title="Zuranolone">Zuranolone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Nonbenzodiazepine" title="Nonbenzodiazepine">Nonbenzodiazepines</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i><a href="/wiki/Cyclopyrrolone" class="mw-redirect" title="Cyclopyrrolone">Cyclopyrrolones</a></i>: <a href="/wiki/Eszopiclone" title="Eszopiclone">Eszopiclone</a></li> <li><a href="/wiki/Pagoclone" title="Pagoclone">Pagoclone</a></li> <li><a href="/wiki/Pazinaclone" title="Pazinaclone">Pazinaclone</a></li> <li><a href="/wiki/Suproclone" title="Suproclone">Suproclone</a></li> <li><a href="/wiki/Suriclone" title="Suriclone">Suriclone</a></li> <li><a href="/wiki/Zopiclone" title="Zopiclone">Zopiclone</a></li></ul> <ul><li><i><a href="/wiki/Imidazopyridine" title="Imidazopyridine">Imidazopyridines</a></i>: <a href="/wiki/Alpidem" title="Alpidem">Alpidem</a></li> <li><a href="/wiki/DS-1_(drug)" title="DS-1 (drug)">DS-1</a></li> <li><a href="/wiki/Necopidem" title="Necopidem">Necopidem</a></li> <li><a href="/wiki/Saripidem" title="Saripidem">Saripidem</a></li> <li><a href="/wiki/Zolpidem" title="Zolpidem">Zolpidem</a></li></ul> <ul><li><i><a href="/wiki/Pyrazolopyrimidine" title="Pyrazolopyrimidine">Pyrazolopyrimidines</a></i>: <a href="/wiki/Divaplon" title="Divaplon">Divaplon</a></li> <li><a href="/wiki/Fasiplon" title="Fasiplon">Fasiplon</a></li> <li><a href="/wiki/Indiplon" title="Indiplon">Indiplon</a></li> <li><a href="/wiki/Lorediplon" title="Lorediplon">Lorediplon</a></li> <li><a href="/wiki/Ocinaplon" title="Ocinaplon">Ocinaplon</a></li> <li><a href="/wiki/Panadiplon" title="Panadiplon">Panadiplon</a></li> <li><a href="/wiki/Taniplon" title="Taniplon">Taniplon</a></li> <li><a href="/wiki/Zaleplon" title="Zaleplon">Zaleplon</a></li></ul> <ul><li><i>Others</i>: <a href="/wiki/Adipiplon" title="Adipiplon">Adipiplon</a></li> <li><a href="/wiki/CGS-8216" title="CGS-8216">CGS-8216</a></li> <li><a href="/wiki/CGS-9896" title="CGS-9896">CGS-9896</a></li> <li><a href="/wiki/CGS-13767" title="CGS-13767">CGS-13767</a></li> <li><a href="/wiki/CGS-20625" title="CGS-20625">CGS-20625</a></li> <li><a href="/wiki/CL-218,872" title="CL-218,872">CL-218,872</a></li> <li><a href="/wiki/CP-615,003" title="CP-615,003">CP-615,003</a></li> <li><a href="/w/index.php?title=CTP-354&action=edit&redlink=1" class="new" title="CTP-354 (page does not exist)">CTP-354</a></li> <li><a href="/wiki/ELB-139" title="ELB-139">ELB-139</a></li> <li><a href="/wiki/GBLD-345" title="GBLD-345">GBLD-345</a></li> <li><a href="/wiki/Imepitoin" title="Imepitoin">Imepitoin</a></li> <li><a href="/wiki/JM-1232" title="JM-1232">JM-1232</a></li> <li><a href="/wiki/L-838,417" title="L-838,417">L-838,417</a></li> <li><a href="/wiki/Lirequinil" title="Lirequinil">Lirequinil (Ro41-3696)</a></li> <li><a href="/wiki/NS-2664" title="NS-2664">NS-2664</a></li> <li><a href="/wiki/NS-2710" title="NS-2710">NS-2710</a></li> <li><a href="/wiki/NS-11394" title="NS-11394">NS-11394</a></li> <li><a href="/wiki/Pipequaline" title="Pipequaline">Pipequaline</a></li> <li><a href="/wiki/ROD-188" title="ROD-188">ROD-188</a></li> <li><a href="/wiki/RWJ-51204" title="RWJ-51204">RWJ-51204</a></li> <li><a href="/wiki/SB-205,384" class="mw-redirect" title="SB-205,384">SB-205,384</a></li> <li><a href="/wiki/SX-3228" title="SX-3228">SX-3228</a></li> <li><a href="/w/index.php?title=TGSC01AA&action=edit&redlink=1" class="new" title="TGSC01AA (page does not exist)">TGSC01AA</a></li> <li><a href="/wiki/TP-003" title="TP-003">TP-003</a></li> <li><a href="/wiki/TPA-023" title="TPA-023">TPA-023</a></li> <li><a href="/wiki/TP-13" title="TP-13">TP-13</a></li> <li><a href="/wiki/U-89843A" title="U-89843A">U-89843A</a></li> <li><a href="/wiki/U-90042" title="U-90042">U-90042</a></li> <li><a href="/wiki/Viqualine" title="Viqualine">Viqualine</a></li> <li><a href="/wiki/Y-23684" title="Y-23684">Y-23684</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Phenol" title="Phenol">Phenols</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Fospropofol" title="Fospropofol">Fospropofol</a></li> <li><a href="/wiki/Propofol" title="Propofol">Propofol</a></li> <li><a href="/wiki/Thymol" title="Thymol">Thymol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Piperidinedione" class="mw-redirect" title="Piperidinedione">Piperidinediones</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Glutethimide" title="Glutethimide">Glutethimide</a></li> <li><a href="/wiki/Methyprylon" title="Methyprylon">Methyprylon</a></li> <li><a href="/wiki/Piperidione" title="Piperidione">Piperidione</a></li> <li><a href="/wiki/Pyrithyldione" title="Pyrithyldione">Pyrithyldione</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Pyrazolopyridine" class="mw-redirect" title="Pyrazolopyridine">Pyrazolopyridines</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cartazolate" title="Cartazolate">Cartazolate</a></li> <li><a href="/wiki/Etazolate" title="Etazolate">Etazolate</a></li> <li><a href="/wiki/ICI-190,622" title="ICI-190,622">ICI-190,622</a></li> <li><a href="/wiki/Tracazolate" title="Tracazolate">Tracazolate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Quinazolinone" title="Quinazolinone">Quinazolinones</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Afloqualone" title="Afloqualone">Afloqualone</a></li> <li><a href="/wiki/Cloroqualone" title="Cloroqualone">Cloroqualone</a></li> <li><a href="/wiki/Diproqualone" title="Diproqualone">Diproqualone</a></li> <li><a href="/wiki/Etaqualone" title="Etaqualone">Etaqualone</a></li> <li><a href="/wiki/Mebroqualone" title="Mebroqualone">Mebroqualone</a></li> <li><a href="/wiki/Mecloqualone" title="Mecloqualone">Mecloqualone</a></li> <li><a href="/wiki/Methaqualone" title="Methaqualone">Methaqualone</a></li> <li><a href="/wiki/Methylmethaqualone" title="Methylmethaqualone">Methylmethaqualone</a></li> <li><a href="/wiki/Nitromethaqualone" title="Nitromethaqualone">Nitromethaqualone</a></li> <li><a href="/wiki/SL-164" title="SL-164">SL-164</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Inhalational_anaesthetic" class="mw-redirect" title="Inhalational anaesthetic">Volatiles</a>/<a href="/wiki/Inhalational_anaesthetic" class="mw-redirect" title="Inhalational anaesthetic">gases</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a class="mw-selflink selflink">Acetone</a></li> <li><a href="/wiki/Acetophenone" title="Acetophenone">Acetophenone</a></li> <li><a href="/wiki/Acetylglycinamide_chloral_hydrate" title="Acetylglycinamide chloral hydrate">Acetylglycinamide chloral hydrate</a></li> <li><a href="/wiki/Aliflurane" title="Aliflurane">Aliflurane</a></li> <li><a href="/wiki/Benzene" title="Benzene">Benzene</a></li> <li><a href="/wiki/Butane" title="Butane">Butane</a></li> <li><a href="/wiki/Butylene" class="mw-redirect" title="Butylene">Butylene</a></li> <li><a href="/wiki/Centalun" title="Centalun">Centalun</a></li> <li><a href="/wiki/Chloral" title="Chloral">Chloral</a></li> <li><a href="/wiki/Chloral_betaine" title="Chloral betaine">Chloral betaine</a></li> <li><a href="/wiki/Chloral_hydrate" title="Chloral hydrate">Chloral hydrate</a></li> <li><a href="/wiki/Chloroform" title="Chloroform">Chloroform</a></li> <li><a href="/wiki/Cryofluorane" class="mw-redirect" title="Cryofluorane">Cryofluorane</a></li> <li><a href="/wiki/Desflurane" title="Desflurane">Desflurane</a></li> <li><a href="/wiki/Dichloralphenazone" title="Dichloralphenazone">Dichloralphenazone</a></li> <li><a href="/wiki/Dichloromethane" title="Dichloromethane">Dichloromethane</a></li> <li><a href="/wiki/Diethyl_ether" title="Diethyl ether">Diethyl ether</a></li> <li><a href="/wiki/Enflurane" title="Enflurane">Enflurane</a></li> <li><a href="/wiki/Chloroethane" title="Chloroethane">Ethyl chloride</a></li> <li><a href="/wiki/Ethylene" title="Ethylene">Ethylene</a></li> <li><a href="/wiki/Fluroxene" title="Fluroxene">Fluroxene</a></li> <li><a href="/wiki/Gasoline" title="Gasoline">Gasoline</a></li> <li><a href="/wiki/Halopropane" title="Halopropane">Halopropane</a></li> <li><a href="/wiki/Halothane" title="Halothane">Halothane</a></li> <li><a href="/wiki/Isoflurane" title="Isoflurane">Isoflurane</a></li> <li><a href="/wiki/Kerosene" title="Kerosene">Kerosine</a></li> <li><a href="/wiki/Methoxyflurane" title="Methoxyflurane">Methoxyflurane</a></li> <li><a href="/wiki/Methoxypropane" title="Methoxypropane">Methoxypropane</a></li> <li><a href="/wiki/Nitric_oxide" title="Nitric oxide">Nitric oxide</a></li> <li><a href="/wiki/Nitrogen" title="Nitrogen">Nitrogen</a></li> <li><a href="/wiki/Nitrous_oxide" title="Nitrous oxide">Nitrous oxide</a></li> <li><a href="/wiki/Norflurane" class="mw-redirect" title="Norflurane">Norflurane</a></li> <li><a href="/wiki/Paraldehyde" title="Paraldehyde">Paraldehyde</a></li> <li><a href="/wiki/Propane" title="Propane">Propane</a></li> <li><a href="/wiki/Propene" class="mw-redirect" title="Propene">Propylene</a></li> <li><a href="/wiki/Roflurane" title="Roflurane">Roflurane</a></li> <li><a href="/wiki/Sevoflurane" title="Sevoflurane">Sevoflurane</a></li> <li><a href="/wiki/Synthane" title="Synthane">Synthane</a></li> <li><a href="/wiki/Teflurane" title="Teflurane">Teflurane</a></li> <li><a href="/wiki/Toluene" title="Toluene">Toluene</a></li> <li><a href="/wiki/1,1,1-Trichloroethane" title="1,1,1-Trichloroethane">Trichloroethane (methyl chloroform)</a></li> <li><a href="/wiki/Trichloroethylene" title="Trichloroethylene">Trichloroethylene</a></li> <li><a href="/wiki/Divinyl_ether" title="Divinyl ether">Vinyl ether</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;">Others/unsorted</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/3-Hydroxybutanal" title="3-Hydroxybutanal">3-Hydroxybutanal</a></li> <li><a href="/w/index.php?title=%CE%91-Ethyl-%CE%B1-methylthiobutyrolactone&action=edit&redlink=1" class="new" title="Α-Ethyl-α-methylthiobutyrolactone (page does not exist)">α-EMTBL</a></li> <li><a href="/w/index.php?title=AA-29504&action=edit&redlink=1" class="new" title="AA-29504 (page does not exist)">AA-29504</a></li> <li><a href="/wiki/Alogabat" title="Alogabat">Alogabat</a></li> <li><a href="/wiki/Avermectin" title="Avermectin">Avermectins</a> (e.g., <a href="/wiki/Ivermectin" title="Ivermectin">ivermectin</a>)</li> <li><a href="/wiki/Bromide" title="Bromide">Bromide</a> compounds (e.g., <a href="/wiki/Lithium_bromide" title="Lithium bromide">lithium bromide</a>, <a href="/wiki/Potassium_bromide" title="Potassium bromide">potassium bromide</a>, <a href="/wiki/Sodium_bromide" title="Sodium bromide">sodium bromide</a>)</li> <li><a href="/wiki/Carbamazepine" title="Carbamazepine">Carbamazepine</a></li> <li><a href="/wiki/Chloralose" title="Chloralose">Chloralose</a></li> <li><a href="/wiki/Chlormezanone" title="Chlormezanone">Chlormezanone</a></li> <li><a href="/wiki/Clomethiazole" title="Clomethiazole">Clomethiazole</a></li> <li><a href="/wiki/Darigabat" title="Darigabat">Darigabat</a></li> <li><a href="/wiki/3,3-Diethyl-2-pyrrolidinone" title="3,3-Diethyl-2-pyrrolidinone">DEABL</a></li> <li><a href="/wiki/Deuterated_etifoxine" title="Deuterated etifoxine">Deuterated etifoxine</a></li> <li><a href="/wiki/Dihydroergoline" class="mw-redirect" title="Dihydroergoline">Dihydroergolines</a> (e.g., <a href="/wiki/Dihydroergocryptine" title="Dihydroergocryptine">dihydroergocryptine</a>, <a href="/w/index.php?title=Dihydroergosine&action=edit&redlink=1" class="new" title="Dihydroergosine (page does not exist)">dihydroergosine</a>, <a href="/wiki/Dihydroergotamine" title="Dihydroergotamine">dihydroergotamine</a>, <a href="/wiki/Ergoloid" title="Ergoloid">ergoloid (dihydroergotoxine)</a>)</li> <li><a href="/w/index.php?title=4-Chloro-N-(2-(2-thienyl)imidazo(1,2-a)pyridin-3-yl)benzamide&action=edit&redlink=1" class="new" title="4-Chloro-N-(2-(2-thienyl)imidazo(1,2-a)pyridin-3-yl)benzamide (page does not exist)">DS2</a></li> <li><a href="/wiki/Efavirenz" title="Efavirenz">Efavirenz</a></li> <li><a href="/wiki/Etazepine" title="Etazepine">Etazepine</a></li> <li><a href="/wiki/Etifoxine" title="Etifoxine">Etifoxine</a></li> <li><a href="/wiki/Fenamate" class="mw-redirect" title="Fenamate">Fenamates</a> (e.g., <a href="/wiki/Flufenamic_acid" title="Flufenamic acid">flufenamic acid</a>, <a href="/wiki/Mefenamic_acid" title="Mefenamic acid">mefenamic acid</a>, <a href="/wiki/Niflumic_acid" title="Niflumic acid">niflumic acid</a>, <a href="/wiki/Tolfenamic_acid" title="Tolfenamic acid">tolfenamic acid</a>)</li> <li><a href="/wiki/Fluoxetine" title="Fluoxetine">Fluoxetine</a></li> <li><a href="/wiki/Flupirtine" title="Flupirtine">Flupirtine</a></li> <li><a href="/wiki/Hopantenic_acid" title="Hopantenic acid">Hopantenic acid</a></li> <li><a href="/wiki/KRM-II-81" title="KRM-II-81">KRM-II-81</a></li> <li><a href="/wiki/Lanthanum" title="Lanthanum">Lanthanum</a></li> <li><a href="/wiki/Lavender_oil" title="Lavender oil">Lavender oil</a></li> <li><a href="/wiki/Lignan" title="Lignan">Lignans</a> (e.g., <a href="/wiki/4-O-methylhonokiol" class="mw-redirect" title="4-O-methylhonokiol">4-O-methylhonokiol</a>, <a href="/wiki/Honokiol" title="Honokiol">honokiol</a>, <a href="/wiki/Magnolol" title="Magnolol">magnolol</a>, <a href="/wiki/Obovatol" title="Obovatol">obovatol</a>)</li> <li><a href="/wiki/Loreclezole" title="Loreclezole">Loreclezole</a></li> <li><a href="/wiki/Menthyl_isovalerate" title="Menthyl isovalerate">Menthyl isovalerate (validolum)</a></li> <li><a href="/wiki/Monastrol" title="Monastrol">Monastrol</a></li> <li><a href="/wiki/Niacin" title="Niacin">Niacin</a></li> <li><a href="/wiki/Niacinamide" class="mw-redirect" title="Niacinamide">Niacinamide</a></li> <li><a href="/wiki/Org_25435" class="mw-redirect" title="Org 25435">Org 25,435</a></li> <li><a href="/wiki/Phenytoin" title="Phenytoin">Phenytoin</a></li> <li><a href="/wiki/Propanidid" title="Propanidid">Propanidid</a></li> <li><a href="/wiki/Retigabine" title="Retigabine">Retigabine (ezogabine)</a></li> <li><a href="/wiki/Safranal" title="Safranal">Safranal</a></li> <li><a href="/wiki/Seproxetine" title="Seproxetine">Seproxetine</a></li> <li><a href="/wiki/Stiripentol" title="Stiripentol">Stiripentol</a></li> <li><a href="/w/index.php?title=Sulfonylalkane&action=edit&redlink=1" class="new" title="Sulfonylalkane (page does not exist)">Sulfonylalkanes</a> (e.g., <a href="/wiki/Sulfonmethane" title="Sulfonmethane">sulfonmethane (sulfonal)</a>, <a href="/wiki/Tetronal" title="Tetronal">tetronal</a>, <a href="/wiki/Trional" title="Trional">trional</a>)</li> <li><a href="/wiki/Terpenoid" title="Terpenoid">Terpenoids</a> (e.g., <a href="/wiki/Borneol" title="Borneol">borneol</a>)</li> <li><a href="/wiki/Topiramate" title="Topiramate">Topiramate</a></li> <li><a href="/wiki/Valerian_(herb)" title="Valerian (herb)">Valerian</a> constituents (e.g., <a href="/wiki/3-methylbutanoic_acid" class="mw-redirect" title="3-methylbutanoic acid">isovaleric acid</a>, <a href="/wiki/Isovaleramide" title="Isovaleramide">isovaleramide</a>, <a href="/wiki/Valerenic_acid" title="Valerenic acid">valerenic acid</a>, <a href="/w/index.php?title=Valerenol&action=edit&redlink=1" class="new" title="Valerenol (page does not exist)">valerenol</a>)</li></ul> <ul><li><i>Unsorted benzodiazepine site positive modulators:</i> <a href="/wiki/%CE%91-Pinene" title="Α-Pinene">α-Pinene</a></li> <li><a href="/wiki/MRK-409_(MK-0343)" class="mw-redirect" title="MRK-409 (MK-0343)">MRK-409 (MK-0343)</a></li> <li><a href="/w/index.php?title=TCS-1105&action=edit&redlink=1" class="new" title="TCS-1105 (page does not exist)">TCS-1105</a></li> <li><a href="/wiki/TCS-1205" title="TCS-1205">TCS-1205</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div><i><b>See also:</b> <a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a> • <a href="/wiki/Template:GABA_receptor_modulators" title="Template:GABA receptor modulators">GABA receptor modulators</a> • <a href="/wiki/Template:GABA_metabolism_and_transport_modulators" title="Template:GABA metabolism and transport modulators">GABA metabolism/transport modulators</a></i></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="Molecules_detected_in_outer_space" 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"><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:Molecules_detected_in_outer_space" title="Template:Molecules detected in outer space"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Molecules_detected_in_outer_space" title="Template talk:Molecules detected in outer space"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Molecules_detected_in_outer_space" title="Special:EditPage/Template:Molecules detected in outer space"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Molecules_detected_in_outer_space" style="font-size:114%;margin:0 4em"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules" title="List of interstellar and circumstellar molecules">Molecules detected in outer space</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Molecule" title="Molecule">Molecules</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Diatomic_molecule" title="Diatomic molecule">Diatomic</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/Aluminium_monochloride" title="Aluminium monochloride">Aluminium monochloride</a></li> <li><a href="/wiki/Aluminium_monofluoride" title="Aluminium monofluoride">Aluminium monofluoride</a></li> <li><a href="/wiki/Aluminium(II)_oxide" title="Aluminium(II) oxide">Aluminium(II) oxide</a></li> <li><a href="/wiki/Argonium" title="Argonium">Argonium</a></li> <li><a href="/wiki/Carbon_cation" class="mw-redirect" title="Carbon cation">Carbon cation</a></li> <li><a href="/wiki/Carbon_monophosphide" title="Carbon monophosphide">Carbon monophosphide</a></li> <li><a href="/wiki/Carbon_monosulfide" title="Carbon monosulfide">Carbon monosulfide</a></li> <li><a href="/wiki/Carbon_monoxide" title="Carbon monoxide">Carbon monoxide</a></li> <li><a href="/wiki/Cyano_radical" title="Cyano radical">Cyano radical</a></li> <li><a href="/wiki/Diatomic_carbon" title="Diatomic carbon">Diatomic carbon</a></li> <li><a href="/w/index.php?title=Fluoromethylidynium&action=edit&redlink=1" class="new" title="Fluoromethylidynium (page does not exist)">Fluoromethylidynium</a></li> <li><a href="/wiki/Helium_hydride_ion" title="Helium hydride ion">Helium hydride ion</a></li> <li><a href="/wiki/Hydrogen_chloride" title="Hydrogen chloride">Hydrogen chloride</a></li> <li><a href="/wiki/Hydrogen_fluoride" title="Hydrogen fluoride">Hydrogen fluoride</a></li> <li><a href="/wiki/Hydrogen" title="Hydrogen">Hydrogen</a> (molecular)</li> <li><a href="/wiki/Hydroxyl_radical" title="Hydroxyl radical">Hydroxyl radical</a></li> <li><a href="/wiki/Iron(II)_oxide" title="Iron(II) oxide">Iron(II) oxide</a></li> <li><a href="/wiki/Magnesium_monohydride" title="Magnesium monohydride">Magnesium monohydride</a></li> <li><a href="/wiki/Methylidyne_radical" title="Methylidyne radical">Methylidyne radical</a></li> <li><a href="/wiki/Nitric_oxide" title="Nitric oxide">Nitric oxide</a></li> <li><a href="/wiki/Nitrogen" title="Nitrogen">Nitrogen</a> (molecular)</li> <li><a href="/wiki/Imidogen" title="Imidogen">Imidogen</a></li> <li><a href="/wiki/Sulfur_mononitride" title="Sulfur mononitride">Sulfur mononitride</a></li> <li><a href="/wiki/Oxygen" title="Oxygen">Oxygen</a> (molecular)</li> <li><a href="/wiki/Phosphorus_monoxide" title="Phosphorus monoxide">Phosphorus monoxide</a></li> <li><a href="/wiki/Phosphorus_mononitride" title="Phosphorus mononitride">Phosphorus mononitride</a></li> <li><a href="/wiki/Potassium_chloride" title="Potassium chloride">Potassium chloride</a></li> <li><a href="/wiki/Silicon_carbide" title="Silicon carbide">Silicon carbide</a></li> <li><a href="/wiki/Silicon_monoxide" title="Silicon monoxide">Silicon monoxide</a></li> <li><a href="/wiki/Silicon_monosulfide" title="Silicon monosulfide">Silicon monosulfide</a></li> <li><a href="/wiki/Sodium_chloride" title="Sodium chloride">Sodium chloride</a></li> <li><a href="/wiki/Sodium_iodide" title="Sodium iodide">Sodium iodide</a></li> <li><a href="/wiki/Sulfanyl" title="Sulfanyl">Sulfanyl</a></li> <li><a href="/wiki/Sulfur_monoxide" title="Sulfur monoxide">Sulfur monoxide</a></li> <li><a href="/wiki/Titanium(II)_oxide" title="Titanium(II) oxide">Titanium(II) oxide</a></li></ul> </div></td><td class="noviewer navbox-image" rowspan="9" style="width:1px;padding:0 0 0 2px"><div><span typeof="mw:File"><a href="/wiki/Nitrous_oxide" title="Nitrous oxide"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/93/Nitrous-oxide-3D-balls.png/60px-Nitrous-oxide-3D-balls.png" decoding="async" width="60" height="24" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/93/Nitrous-oxide-3D-balls.png/90px-Nitrous-oxide-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/93/Nitrous-oxide-3D-balls.png/120px-Nitrous-oxide-3D-balls.png 2x" data-file-width="1100" data-file-height="441" /></a></span> <br /><br /><br /><br /> <span typeof="mw:File"><a href="/wiki/Ethanol" title="Ethanol"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b0/Ethanol-3D-balls.png/60px-Ethanol-3D-balls.png" decoding="async" width="60" height="41" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b0/Ethanol-3D-balls.png/90px-Ethanol-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b0/Ethanol-3D-balls.png/120px-Ethanol-3D-balls.png 2x" data-file-width="1100" data-file-height="754" /></a></span> <br /><br /><br /><br /> <span typeof="mw:File"><a href="/wiki/Buckminsterfullerene" title="Buckminsterfullerene"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0f/Buckminsterfullerene-perspective-3D-balls.png/60px-Buckminsterfullerene-perspective-3D-balls.png" decoding="async" width="60" height="63" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0f/Buckminsterfullerene-perspective-3D-balls.png/90px-Buckminsterfullerene-perspective-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/0f/Buckminsterfullerene-perspective-3D-balls.png/120px-Buckminsterfullerene-perspective-3D-balls.png 2x" data-file-width="1056" data-file-height="1100" /></a></span></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Triatomic_molecule" title="Triatomic molecule">Triatomic</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/Aluminium(I)_hydroxide" class="mw-redirect" title="Aluminium(I) hydroxide">Aluminium(I) hydroxide</a></li> <li><a href="/w/index.php?title=Aluminium_isocyanide&action=edit&redlink=1" class="new" title="Aluminium isocyanide (page does not exist)">Aluminium isocyanide</a></li> <li><a href="/wiki/Amino_radical" title="Amino radical">Amino radical</a></li> <li><a href="/wiki/Carbon_dioxide" title="Carbon dioxide">Carbon dioxide</a></li> <li><a href="/wiki/Carbonyl_sulfide" title="Carbonyl sulfide">Carbonyl sulfide</a></li> <li><a href="/w/index.php?title=CCP_radical&action=edit&redlink=1" class="new" title="CCP radical (page does not exist)">CCP radical</a></li> <li><a href="/wiki/Halonium_ion" title="Halonium ion">Chloronium</a></li> <li><a href="/wiki/Diazenylium" title="Diazenylium">Diazenylium</a></li> <li><a href="/wiki/Dicarbon_monoxide" title="Dicarbon monoxide">Dicarbon monoxide</a></li> <li><a href="/w/index.php?title=Disilicon_carbide&action=edit&redlink=1" class="new" title="Disilicon carbide (page does not exist)">Disilicon carbide</a></li> <li><a href="/wiki/Ethynyl_radical" title="Ethynyl radical">Ethynyl radical</a></li> <li><a href="/w/index.php?title=Formyl_radical&action=edit&redlink=1" class="new" title="Formyl radical (page does not exist)">Formyl radical</a></li> <li><a href="/wiki/Hydrogen_cyanide" title="Hydrogen cyanide">Hydrogen cyanide</a> (HCN)</li> <li><a href="/wiki/Hydrogen_isocyanide" title="Hydrogen isocyanide">Hydrogen isocyanide</a> (HNC)</li> <li><a href="/wiki/Hydrogen_sulfide" title="Hydrogen sulfide">Hydrogen sulfide</a></li> <li><a href="/wiki/Hydroperoxyl" title="Hydroperoxyl">Hydroperoxyl</a></li> <li><a href="/w/index.php?title=Iron_cyanide&action=edit&redlink=1" class="new" title="Iron cyanide (page does not exist)">Iron cyanide</a></li> <li><a href="/w/index.php?title=Isoformyl&action=edit&redlink=1" class="new" title="Isoformyl (page does not exist)">Isoformyl</a></li> <li><a href="/wiki/Magnesium_cyanide" title="Magnesium cyanide">Magnesium cyanide</a></li> <li><a href="/w/index.php?title=Magnesium_isocyanide&action=edit&redlink=1" class="new" title="Magnesium isocyanide (page does not exist)">Magnesium isocyanide</a></li> <li><a href="/wiki/Methylene_(compound)" title="Methylene (compound)">Methylene</a></li> <li><a href="/wiki/Diazenylium" title="Diazenylium">N<sub>2</sub>H<sup>+</sup></a></li> <li><a href="/wiki/Nitrous_oxide" title="Nitrous oxide">Nitrous oxide</a></li> <li><a href="/wiki/Nitroxyl" title="Nitroxyl">Nitroxyl</a></li> <li><a href="/wiki/Ozone" title="Ozone">Ozone</a></li> <li><a href="/wiki/Methylidynephosphane" title="Methylidynephosphane">Methylidynephosphane</a></li> <li><a href="/wiki/Potassium_cyanide" title="Potassium cyanide">Potassium cyanide</a></li> <li><a href="/wiki/Trihydrogen_cation" title="Trihydrogen cation">Trihydrogen cation</a></li> <li><a href="/wiki/Sodium_cyanide" title="Sodium cyanide">Sodium cyanide</a></li> <li><a href="/wiki/Sodium_hydroxide" title="Sodium hydroxide">Sodium hydroxide</a></li> <li><a href="/w/index.php?title=Silicon_carbonitride&action=edit&redlink=1" class="new" title="Silicon carbonitride (page does not exist)">Silicon carbonitride</a></li> <li><a href="/w/index.php?title=C-Silicon_dicarbide&action=edit&redlink=1" class="new" title="C-Silicon dicarbide (page does not exist)">c-Silicon dicarbide</a></li> <li><a href="/w/index.php?title=SiNC&action=edit&redlink=1" class="new" title="SiNC (page does not exist)">SiNC</a></li> <li><a href="/wiki/Sulfur_dioxide" title="Sulfur dioxide">Sulfur dioxide</a></li> <li><a href="/w/index.php?title=Thioformyl&action=edit&redlink=1" class="new" title="Thioformyl (page does not exist)">Thioformyl</a></li> <li><a href="/wiki/Thioxoethenylidene" title="Thioxoethenylidene">Thioxoethenylidene</a></li> <li><a href="/wiki/Titanium_dioxide" title="Titanium dioxide">Titanium dioxide</a></li> <li><a href="/wiki/Tricarbon" title="Tricarbon">Tricarbon</a></li> <li><a href="/wiki/Water" title="Water">Water</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Four<br />atoms</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/Acetylene" title="Acetylene">Acetylene</a></li> <li><a href="/wiki/Ammonia" title="Ammonia">Ammonia</a></li> <li><a href="/wiki/Isocyanic_acid" title="Isocyanic acid">Isocyanic acid</a></li> <li><a href="/wiki/Polyyne" title="Polyyne">Cyanoethynyl</a></li> <li><a href="/wiki/Interstellar_formaldehyde" title="Interstellar formaldehyde">Formaldehyde</a></li> <li><a href="/wiki/Fulminic_acid" title="Fulminic acid">Fulminic acid</a></li> <li><a href="/w/index.php?title=HCCN&action=edit&redlink=1" class="new" title="HCCN (page does not exist)">HCCN</a></li> <li><a href="/wiki/Hydrogen_peroxide" title="Hydrogen peroxide">Hydrogen peroxide</a></li> <li><a href="/w/index.php?title=Hydromagnesium_isocyanide&action=edit&redlink=1" class="new" title="Hydromagnesium isocyanide (page does not exist)">Hydromagnesium isocyanide</a></li> <li><a href="/wiki/Isocyanic_acid" title="Isocyanic acid">Isocyanic acid</a></li> <li><a href="/wiki/Thiocyanic_acid" title="Thiocyanic acid">Isothiocyanic acid</a></li> <li><a href="/w/index.php?title=Ketenyl&action=edit&redlink=1" class="new" title="Ketenyl (page does not exist)">Ketenyl</a></li> <li><a href="/w/index.php?title=Methylene_amidogen&action=edit&redlink=1" class="new" title="Methylene amidogen (page does not exist)">Methylene amidogen</a></li> <li><a href="/wiki/Methyl_cation" class="mw-redirect" title="Methyl cation">Methyl cation</a></li> <li><a href="/wiki/Methyl_radical" title="Methyl radical">Methyl radical</a></li> <li><a href="/wiki/Propynylidyne" title="Propynylidyne">Propynylidyne</a></li> <li><a href="/w/index.php?title=Protonated_carbon_dioxide&action=edit&redlink=1" class="new" title="Protonated carbon dioxide (page does not exist)">Protonated carbon dioxide</a></li> <li><a href="/wiki/Protonated_hydrogen_cyanide" title="Protonated hydrogen cyanide">Protonated hydrogen cyanide</a></li> <li><a href="/w/index.php?title=Silicon_tricarbide&action=edit&redlink=1" class="new" title="Silicon tricarbide (page does not exist)">Silicon tricarbide</a></li> <li><a href="/wiki/Thioformaldehyde" title="Thioformaldehyde">Thioformaldehyde</a></li> <li><a href="/wiki/Tricarbon_monoxide" title="Tricarbon monoxide">Tricarbon monoxide</a></li> <li><a href="/wiki/Tricarbon_monosulfide" title="Tricarbon monosulfide">Tricarbon monosulfide</a></li> <li><a href="/wiki/Thiocyanic_acid" title="Thiocyanic acid">Thiocyanic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Five<br />atoms</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/Ammonium" title="Ammonium">Ammonium</a> ion</li> <li><a href="/wiki/Polyyne" title="Polyyne">Butadiynyl</a></li> <li><a href="/wiki/Carbodiimide" title="Carbodiimide">Carbodiimide</a></li> <li><a href="/wiki/Cyanamide" title="Cyanamide">Cyanamide</a></li> <li><a href="/wiki/Cyanoacetylene" title="Cyanoacetylene">Cyanoacetylene</a></li> <li><a href="/w/index.php?title=Cyanoformaldehyde&action=edit&redlink=1" class="new" title="Cyanoformaldehyde (page does not exist)">Cyanoformaldehyde</a></li> <li><a href="/wiki/Cyanomethyl" title="Cyanomethyl">Cyanomethyl</a></li> <li><a href="/wiki/Cyclopropenylidene" title="Cyclopropenylidene">Cyclopropenylidene</a></li> <li><a href="/wiki/Formic_acid" title="Formic acid">Formic acid</a></li> <li><a href="/w/index.php?title=Isocyanoacetylene&action=edit&redlink=1" class="new" title="Isocyanoacetylene (page does not exist)">Isocyanoacetylene</a></li> <li><a href="/wiki/Ketene" title="Ketene">Ketene</a></li> <li><a href="/wiki/Methane" title="Methane">Methane</a></li> <li><a href="/wiki/Methoxy" class="mw-redirect" title="Methoxy">Methoxy radical</a></li> <li><a href="/w/index.php?title=Methylenimine&action=edit&redlink=1" class="new" title="Methylenimine (page does not exist)">Methylenimine</a></li> <li><a href="/w/index.php?title=Propadienylidene&action=edit&redlink=1" class="new" title="Propadienylidene (page does not exist)">Propadienylidene</a></li> <li><a href="/w/index.php?title=Protonated_formaldehyde&action=edit&redlink=1" class="new" title="Protonated formaldehyde (page does not exist)">Protonated formaldehyde</a></li> <li><a href="/wiki/Silane" title="Silane">Silane</a></li> <li><a href="/w/index.php?title=Silicon-carbide_cluster&action=edit&redlink=1" class="new" title="Silicon-carbide cluster (page does not exist)">Silicon-carbide cluster</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Six<br />atoms</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/Acetonitrile" title="Acetonitrile">Acetonitrile</a></li> <li><a href="/w/index.php?title=Cyanobutadiynyl_radical&action=edit&redlink=1" class="new" title="Cyanobutadiynyl radical (page does not exist)">Cyanobutadiynyl radical</a></li> <li><a href="/w/index.php?title=E-Cyanomethanimine&action=edit&redlink=1" class="new" title="E-Cyanomethanimine (page does not exist)">E-Cyanomethanimine</a></li> <li><a href="/wiki/Cyclopropenone" title="Cyclopropenone">Cyclopropenone</a></li> <li><a href="/wiki/Diacetylene" title="Diacetylene">Diacetylene</a></li> <li><a href="/wiki/Ethylene" title="Ethylene">Ethylene</a></li> <li><a href="/wiki/Formamide" title="Formamide">Formamide</a></li> <li><a href="/w/index.php?title=HC4N&action=edit&redlink=1" class="new" title="HC4N (page does not exist)">HC<sub>4</sub>N</a></li> <li><a href="/wiki/Ketenimine" class="mw-redirect" title="Ketenimine">Ketenimine</a></li> <li><a href="/wiki/Methanethiol" title="Methanethiol">Methanethiol</a></li> <li><a href="/wiki/Methanol" title="Methanol">Methanol</a></li> <li><a href="/wiki/Methyl_isocyanide" title="Methyl isocyanide">Methyl isocyanide</a></li> <li><a href="/wiki/Polyyne" title="Polyyne">Pentynylidyne</a></li> <li><a href="/wiki/Propynal" class="mw-redirect" title="Propynal">Propynal</a></li> <li><a href="/w/index.php?title=Protonated_cyanoacetylene&action=edit&redlink=1" class="new" title="Protonated cyanoacetylene (page does not exist)">Protonated cyanoacetylene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Seven<br />atoms</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/Acetaldehyde" title="Acetaldehyde">Acetaldehyde</a></li> <li><a href="/wiki/Acrylonitrile" title="Acrylonitrile">Acrylonitrile</a> <ul><li><a href="/wiki/Vinyl_cyanide" class="mw-redirect" title="Vinyl cyanide">Vinyl cyanide</a></li></ul></li> <li><a href="/wiki/Cyanopolyyne" title="Cyanopolyyne">Cyanodiacetylene</a></li> <li><a href="/wiki/Ethylene_oxide" title="Ethylene oxide">Ethylene oxide</a></li> <li><a href="/wiki/Glycolonitrile" title="Glycolonitrile">Glycolonitrile</a></li> <li><a href="/wiki/Hexatriynyl_radical" title="Hexatriynyl radical">Hexatriynyl radical</a></li> <li><a href="/wiki/Propyne" title="Propyne">Propyne</a></li> <li><a href="/wiki/Methylamine" title="Methylamine">Methylamine</a></li> <li><a href="/wiki/Methyl_isocyanate" title="Methyl isocyanate">Methyl isocyanate</a></li> <li><a href="/wiki/Vinyl_alcohol" title="Vinyl alcohol">Vinyl alcohol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Eight<br />atoms</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/Acetic_acid" title="Acetic acid">Acetic acid</a></li> <li><a href="/wiki/Aminoacetonitrile" title="Aminoacetonitrile">Aminoacetonitrile</a></li> <li><a href="/w/index.php?title=Cyanoallene&action=edit&redlink=1" class="new" title="Cyanoallene (page does not exist)">Cyanoallene</a></li> <li><a href="/wiki/Ethanimine" title="Ethanimine">Ethanimine</a></li> <li><a href="/wiki/Glycolaldehyde" title="Glycolaldehyde">Glycolaldehyde</a></li> <li><a href="/wiki/Polyyne" title="Polyyne">Hexapentaenylidene</a></li> <li><a href="/wiki/Polyyne" title="Polyyne">Methylcyanoacetylene</a></li> <li><a href="/wiki/Methyl_formate" title="Methyl formate">Methyl formate</a></li> <li><a href="/wiki/Acrolein" title="Acrolein">Acrolein</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Nine<br />atoms</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/Acetamide" title="Acetamide">Acetamide</a></li> <li><a href="/wiki/Cyanopolyyne" title="Cyanopolyyne">Cyanohexatriyne</a></li> <li><a href="/wiki/Dimethyl_ether" title="Dimethyl ether">Dimethyl ether</a></li> <li><a href="/wiki/Ethanol" title="Ethanol">Ethanol</a></li> <li><a href="/wiki/Polyyne" title="Polyyne">Methyldiacetylene</a></li> <li><a href="/wiki/Octatetraynyl_radical" title="Octatetraynyl radical">Octatetraynyl radical</a></li> <li><a href="/wiki/Propene" class="mw-redirect" title="Propene">Propene</a></li> <li><a href="/wiki/Ethanethiol" title="Ethanethiol">Ethanethiol</a></li> <li><a href="/wiki/Propionitrile" title="Propionitrile">Propionitrile</a></li> <li><a href="/wiki/N-Methylformamide" title="N-Methylformamide">N-Methylformamide</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Ten<br />atoms<br />or more</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 class="mw-selflink selflink">Acetone</a></li> <li><a href="/wiki/Benzene" title="Benzene">Benzene</a></li> <li><a href="/wiki/Benzonitrile" title="Benzonitrile">Benzonitrile</a></li> <li><a href="/wiki/Buckminsterfullerene" title="Buckminsterfullerene">Buckminsterfullerene</a> (C<sub>60</sub>, C<sub>60</sub><sup>+</sup>, fullerene, buckyball)</li> <li><a href="/wiki/C70_fullerene" title="C70 fullerene">C<sub>70</sub> fullerene</a></li> <li><a href="/wiki/Cyanopolyyne" title="Cyanopolyyne">Cyanodecapentayne</a></li> <li><a href="/wiki/Ethylene_glycol" title="Ethylene glycol">Ethylene glycol</a></li> <li><a href="/wiki/Ethyl_formate" title="Ethyl formate">Ethyl formate</a></li> <li><a href="/wiki/Methyl_acetate" title="Methyl acetate">Methyl acetate</a></li> <li><a href="/wiki/Cyanopolyyne" title="Cyanopolyyne">Methyl-cyano-diacetylene</a></li> <li><a href="/wiki/Polyyne" title="Polyyne">Methyltriacetylene</a></li> <li><a href="/wiki/Propionaldehyde" title="Propionaldehyde">Propionaldehyde</a></li> <li><a href="/wiki/Butyronitrile" title="Butyronitrile">Butyronitrile</a></li> <li><a href="/wiki/Pyrimidine" title="Pyrimidine">Pyrimidine</a></li> <li><a href="/w/index.php?title=Heptatrienyl_radical&action=edit&redlink=1" class="new" title="Heptatrienyl radical (page does not exist)">Heptatrienyl radical</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/Deuterium" title="Deuterium">Deuterated</a><br />molecules</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/Ammonia" title="Ammonia">Ammonia</a></li> <li><a href="/wiki/Ammonium" title="Ammonium">Ammonium</a> ion</li> <li><a href="/wiki/Formaldehyde" title="Formaldehyde">Formaldehyde</a></li> <li><a href="/wiki/Interstellar_formaldehyde#Interstellar_reactions" title="Interstellar formaldehyde">Formyl radical</a></li> <li><a href="/wiki/Heavy_water" title="Heavy water">Heavy water</a></li> <li><a href="/wiki/Hydrogen_cyanide" title="Hydrogen cyanide">Hydrogen cyanide</a></li> <li><a href="/wiki/Hydrogen_deuteride" title="Hydrogen deuteride">Hydrogen deuteride</a></li> <li><a href="/wiki/Hydrogen_isocyanide" title="Hydrogen isocyanide">Hydrogen isocyanide</a></li> <li><a href="/wiki/Propyne" title="Propyne">Propyne</a></li> <li><a href="/wiki/Diazenylium" title="Diazenylium">N<sub>2</sub>D<sup>+</sup></a></li> <li><a href="/wiki/Trihydrogen_cation" title="Trihydrogen cation">Trihydrogen cation</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Unconfirmed</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/Anthracene" title="Anthracene">Anthracene</a></li> <li><a href="/wiki/Dihydroxyacetone" title="Dihydroxyacetone">Dihydroxyacetone</a></li> <li><a href="/wiki/Methoxyethane" title="Methoxyethane">Methoxyethane</a></li> <li><a href="/wiki/Glycine" title="Glycine">Glycine</a></li> <li><a href="/wiki/Graphene" title="Graphene">Graphene</a></li> <li><a href="/wiki/Hemolithin" title="Hemolithin">Hemolithin</a></li> <li><a href="/w/index.php?title=H2NCO%2B&action=edit&redlink=1" class="new" title="H2NCO+ (page does not exist)">H<sub>2</sub>NCO<sup>+</sup></a></li> <li><a href="/wiki/Carbon" title="Carbon">Linear C<sub>5</sub></a></li> <li><a href="/wiki/Naphthalene" title="Naphthalene">Naphthalene cation</a></li> <li><a href="/wiki/Phosphine" title="Phosphine">Phosphine</a></li> <li><a href="/wiki/Pyrene" title="Pyrene">Pyrene</a></li> <li><a href="/wiki/Silylidyne" title="Silylidyne">Silylidyne</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#See_also" title="List of interstellar and circumstellar molecules">Related</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/Abiogenesis" title="Abiogenesis">Abiogenesis</a></li> <li><a href="/wiki/Astrobiology" title="Astrobiology">Astrobiology</a></li> <li><a href="/wiki/Astrochemistry" title="Astrochemistry">Astrochemistry</a></li> <li><a href="/wiki/Atomic_and_molecular_astrophysics" title="Atomic and molecular astrophysics">Atomic and molecular astrophysics</a></li> <li><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></li> <li><a href="/wiki/Circumstellar_dust" title="Circumstellar dust">Circumstellar dust</a></li> <li><a href="/wiki/Circumstellar_envelope" title="Circumstellar envelope">Circumstellar envelope</a></li> <li><a href="/wiki/Cosmic_dust" title="Cosmic dust">Cosmic dust</a></li> <li><a href="/wiki/Cosmic_ray" title="Cosmic ray">Cosmic ray</a></li> <li><a href="/wiki/Cosmochemistry" title="Cosmochemistry">Cosmochemistry</a></li> <li><a href="/wiki/Diffuse_interstellar_band" class="mw-redirect" title="Diffuse interstellar band">Diffuse interstellar band</a></li> <li><a href="/wiki/Earliest_known_life_forms" title="Earliest known life forms">Earliest known life forms</a></li> <li><a href="/wiki/Extraterrestrial_life" title="Extraterrestrial life">Extraterrestrial life</a></li> <li><a href="/wiki/Extraterrestrial_liquid_water" title="Extraterrestrial liquid water">Extraterrestrial liquid water</a></li> <li><a href="/wiki/Forbidden_mechanism" title="Forbidden mechanism">Forbidden mechanism</a></li> <li><a href="/wiki/Homochirality" title="Homochirality">Homochirality</a></li> <li><a href="/wiki/Intergalactic_dust" title="Intergalactic dust">Intergalactic dust</a></li> <li><a href="/wiki/Interplanetary_medium" title="Interplanetary medium">Interplanetary medium</a></li> <li><a href="/wiki/Interstellar_medium" title="Interstellar medium">Interstellar medium</a></li> <li><a href="/wiki/Photodissociation_region" title="Photodissociation region">Photodissociation region</a></li> <li><a href="/wiki/Iron%E2%80%93sulfur_world_theory" class="mw-redirect" title="Iron–sulfur world theory">Iron–sulfur world theory</a></li> <li><a href="/wiki/Kerogen" title="Kerogen">Kerogen</a></li> <li><a href="/wiki/Molecules_in_stars" title="Molecules in stars">Molecules in stars</a></li> <li><a href="/wiki/Nexus_for_Exoplanet_System_Science" title="Nexus for Exoplanet System Science">Nexus for Exoplanet System Science</a></li> <li><a href="/wiki/Organic_compound" title="Organic compound">Organic compound</a></li> <li><a href="/wiki/Outer_space" title="Outer space">Outer space</a></li> <li><a href="/wiki/PAH_world_hypothesis" title="PAH world hypothesis">PAH world hypothesis</a></li> <li><a href="/wiki/Pseudo-panspermia" title="Pseudo-panspermia">Pseudo-panspermia</a></li> <li><a href="/wiki/Polycyclic_aromatic_hydrocarbon" title="Polycyclic aromatic hydrocarbon">Polycyclic aromatic hydrocarbon</a> (PAH)</li> <li><a href="/wiki/RNA_world_hypothesis" class="mw-redirect" title="RNA world hypothesis">RNA world hypothesis</a></li> <li><a href="/wiki/Spectroscopy" title="Spectroscopy">Spectroscopy</a></li> <li><a href="/wiki/Tholin" title="Tholin">Tholin</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2" style="font-weight: bold;"><div> <ul><li><b><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, 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