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</button> <ul id="toc-Nomenclature_and_structure-sublist" class="vector-toc-list"> <li id="toc-Geometry" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Geometry"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.1</span> <span>Geometry</span> </div> </a> <ul id="toc-Geometry-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Benzenoid_hydrocarbons" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Benzenoid_hydrocarbons"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.2</span> <span>Benzenoid hydrocarbons</span> </div> </a> <ul id="toc-Benzenoid_hydrocarbons-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Bonding_and_aromaticity" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Bonding_and_aromaticity"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>Bonding and aromaticity</span> </div> </a> <ul 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class="vector-toc-link" href="#Redox"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.2</span> <span>Redox</span> </div> </a> <ul id="toc-Redox-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Sources" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Sources"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Sources</span> </div> </a> <button aria-controls="toc-Sources-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Sources subsection</span> </button> <ul id="toc-Sources-sublist" class="vector-toc-list"> <li id="toc-Artificial" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Artificial"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.1</span> <span>Artificial</span> </div> </a> <ul id="toc-Artificial-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Natural" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Natural"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.2</span> <span>Natural</span> </div> </a> <ul id="toc-Natural-sublist" class="vector-toc-list"> <li id="toc-Natural_fires" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Natural_fires"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.2.1</span> <span>Natural fires</span> </div> </a> <ul id="toc-Natural_fires-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Fossil_carbon" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Fossil_carbon"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.2.2</span> <span>Fossil carbon</span> </div> </a> <ul id="toc-Fossil_carbon-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Extraterrestrial" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Extraterrestrial"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.2.3</span> <span>Extraterrestrial</span> </div> </a> <ul id="toc-Extraterrestrial-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Minor_sources" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Minor_sources"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.2.4</span> <span>Minor sources</span> </div> </a> <ul id="toc-Minor_sources-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> </ul> </li> <li id="toc-Distribution_in_the_environment" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Distribution_in_the_environment"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Distribution in the environment</span> </div> </a> <button aria-controls="toc-Distribution_in_the_environment-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 Distribution in the environment subsection</span> </button> <ul id="toc-Distribution_in_the_environment-sublist" class="vector-toc-list"> <li id="toc-Aquatic_environments" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Aquatic_environments"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1</span> <span>Aquatic environments</span> </div> </a> <ul id="toc-Aquatic_environments-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Human_exposure" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Human_exposure"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.2</span> <span>Human exposure</span> </div> </a> <ul id="toc-Human_exposure-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Environmental_pollution_and_degradation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Environmental_pollution_and_degradation"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.3</span> <span>Environmental pollution and degradation</span> </div> </a> <ul id="toc-Environmental_pollution_and_degradation-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Urban_soils" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Urban_soils"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.4</span> <span>Urban soils</span> </div> </a> <ul id="toc-Urban_soils-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Peatlands" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Peatlands"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.5</span> <span>Peatlands</span> </div> </a> <ul id="toc-Peatlands-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Rivers,_estuarine_and_coastal_sediments" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Rivers,_estuarine_and_coastal_sediments"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.6</span> <span>Rivers, estuarine and coastal sediments</span> </div> </a> <ul id="toc-Rivers,_estuarine_and_coastal_sediments-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Human_health" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Human_health"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Human health</span> </div> </a> <button aria-controls="toc-Human_health-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 Human health subsection</span> </button> <ul id="toc-Human_health-sublist" class="vector-toc-list"> <li id="toc-Cancer" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Cancer"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.1</span> <span>Cancer</span> </div> </a> <ul id="toc-Cancer-sublist" class="vector-toc-list"> <li id="toc-History" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#History"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.1.1</span> <span>History</span> </div> </a> <ul id="toc-History-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Mechanisms_of_carcinogenesis" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Mechanisms_of_carcinogenesis"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.1.2</span> <span>Mechanisms of carcinogenesis</span> </div> </a> <ul id="toc-Mechanisms_of_carcinogenesis-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Cardiovascular_disease" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Cardiovascular_disease"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.2</span> <span>Cardiovascular disease</span> </div> </a> <ul id="toc-Cardiovascular_disease-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Developmental_impacts" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Developmental_impacts"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.3</span> <span>Developmental impacts</span> </div> </a> <ul id="toc-Developmental_impacts-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Regulation_and_oversight" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Regulation_and_oversight"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Regulation and oversight</span> </div> </a> <ul id="toc-Regulation_and_oversight-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Detection_and_optical_properties" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Detection_and_optical_properties"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>Detection and optical properties</span> </div> </a> <button aria-controls="toc-Detection_and_optical_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 Detection and optical properties subsection</span> </button> <ul id="toc-Detection_and_optical_properties-sublist" class="vector-toc-list"> <li id="toc-Origins_of_life" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Origins_of_life"> <div class="vector-toc-text"> <span class="vector-toc-numb">8.1</span> <span>Origins of life</span> </div> </a> <ul id="toc-Origins_of_life-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>See also</span> </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">10</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">11</span> <span>External links</span> </div> </a> <ul id="toc-External_links-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header 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<h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Polycyclic aromatic hydrocarbon</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 39 languages" > <label id="p-lang-btn-label" for="p-lang-btn-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--action-progressive mw-portlet-lang-heading-39" aria-hidden="true" ><span class="vector-icon mw-ui-icon-language-progressive mw-ui-icon-wikimedia-language-progressive"></span> <span class="vector-dropdown-label-text">39 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D9%87%D9%8A%D8%AF%D8%B1%D9%88%D9%83%D8%B1%D8%A8%D9%88%D9%86_%D8%B9%D8%B7%D8%B1%D9%8A_%D9%85%D8%AA%D8%B9%D8%AF%D8%AF_%D8%A7%D9%84%D8%AD%D9%84%D9%82%D8%A7%D8%AA" title="هيدروكربون عطري متعدد الحلقات – Arabic" lang="ar" hreflang="ar" data-title="هيدروكربون عطري متعدد الحلقات" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-az mw-list-item"><a href="https://az.wikipedia.org/wiki/%C3%87ox_d%C3%B6vrl%C3%BCl%C9%99r" title="Çox dövrlülər – Azerbaijani" lang="az" hreflang="az" data-title="Çox dövrlülər" data-language-autonym="Azərbaycanca" data-language-local-name="Azerbaijani" class="interlanguage-link-target"><span>Azərbaycanca</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Hidrocarbur_arom%C3%A0tic_polic%C3%ADclic" title="Hidrocarbur aromàtic policíclic – Catalan" lang="ca" hreflang="ca" data-title="Hidrocarbur aromàtic policíclic" 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/Polyaromatick%C3%A9_uhlovod%C3%ADky" title="Polyaromatické uhlovodíky – Czech" lang="cs" hreflang="cs" data-title="Polyaromatické uhlovodíky" 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/Aromatiske_kulbrinter" title="Aromatiske kulbrinter – Danish" lang="da" hreflang="da" data-title="Aromatiske kulbrinter" 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/Polycyclische_aromatische_Kohlenwasserstoffe" title="Polycyclische aromatische Kohlenwasserstoffe – German" lang="de" hreflang="de" data-title="Polycyclische aromatische Kohlenwasserstoffe" 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/Pol%C3%BCts%C3%BCklilised_aromaatsed_s%C3%BCsivesinikud" title="Polütsüklilised aromaatsed süsivesinikud – Estonian" lang="et" hreflang="et" data-title="Polütsüklilised aromaatsed süsivesinikud" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Hidrocarburo_arom%C3%A1tico_polic%C3%ADclico" title="Hidrocarburo aromático policíclico – Spanish" lang="es" hreflang="es" data-title="Hidrocarburo aromático policíclico" 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/Policikla_aromata_hidrokarbonido" title="Policikla aromata hidrokarbonido – Esperanto" lang="eo" hreflang="eo" data-title="Policikla aromata hidrokarbonido" 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/Hidrokarburo_aromatiko_polizikliko" title="Hidrokarburo aromatiko polizikliko – Basque" lang="eu" hreflang="eu" data-title="Hidrokarburo aromatiko polizikliko" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D9%87%DB%8C%D8%AF%D8%B1%D9%88%DA%A9%D8%B1%D8%A8%D9%86_%D8%A2%D8%B1%D9%88%D9%85%D8%A7%D8%AA%DB%8C%DA%A9_%DA%86%D9%86%D8%AF%D8%AD%D9%84%D9%82%D9%87%E2%80%8C%D8%A7%DB%8C" title="هیدروکربن آروماتیک چندحلقه‌ای – Persian" lang="fa" hreflang="fa" data-title="هیدروکربن آروماتیک چندحلقه‌ای" 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/Hydrocarbure_aromatique_polycyclique" title="Hydrocarbure aromatique polycyclique – French" lang="fr" hreflang="fr" data-title="Hydrocarbure aromatique polycyclique" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Hidrocarburo_arom%C3%A1tico_polic%C3%ADclico" title="Hidrocarburo aromático policíclico – Galician" lang="gl" hreflang="gl" data-title="Hidrocarburo aromático policíclico" 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%97%AC%EB%9F%AC_%EA%B3%A0%EB%A6%AC_%EB%B0%A9%ED%96%A5%EC%A1%B1_%ED%83%84%ED%99%94%EC%88%98%EC%86%8C" title="여러 고리 방향족 탄화수소 – Korean" lang="ko" hreflang="ko" data-title="여러 고리 방향족 탄화수소" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D5%8A%D5%B8%D5%AC%D5%AB%D6%81%D5%AB%D5%AF%D5%AC%D5%AB%D5%AF_%D5%A1%D6%80%D5%B8%D5%B4%D5%A1%D5%BF%D5%AB%D5%AF_%D5%A1%D5%AE%D5%AD%D5%A1%D5%BB%D6%80%D5%A1%D5%AE%D5%AB%D5%B6%D5%B6%D5%A5%D6%80" title="Պոլիցիկլիկ արոմատիկ ածխաջրածիններ – Armenian" lang="hy" hreflang="hy" data-title="Պոլիցիկլիկ արոմատիկ ածխաջրածիններ" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Hidrokarbon_aromatik_polisiklik" title="Hidrokarbon aromatik polisiklik – Indonesian" lang="id" hreflang="id" data-title="Hidrokarbon aromatik polisiklik" 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/Idrocarburi_policiclici_aromatici" title="Idrocarburi policiclici aromatici – Italian" lang="it" hreflang="it" data-title="Idrocarburi policiclici aromatici" 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%A4%D7%97%D7%9E%D7%99%D7%9E%D7%A0%D7%99%D7%9D_%D7%90%D7%A8%D7%95%D7%9E%D7%98%D7%99%D7%99%D7%9D_%D7%A8%D7%91-%D7%98%D7%91%D7%A2%D7%AA%D7%99%D7%99%D7%9D" title="פחמימנים ארומטיים רב-טבעתיים – Hebrew" lang="he" hreflang="he" data-title="פחמימנים ארומטיים רב-טבעתיים" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Policikliskie_arom%C4%81tiskie_og%C4%BC%C5%ABde%C5%86ra%C5%BEi" title="Policikliskie aromātiskie ogļūdeņraži – Latvian" lang="lv" hreflang="lv" data-title="Policikliskie aromātiskie ogļūdeņraži" 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/Policikliniai_aromatiniai_angliavandeniliai" title="Policikliniai aromatiniai angliavandeniliai – Lithuanian" lang="lt" hreflang="lt" data-title="Policikliniai aromatiniai angliavandeniliai" data-language-autonym="Lietuvių" data-language-local-name="Lithuanian" class="interlanguage-link-target"><span>Lietuvių</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Policiklusos_arom%C3%A1s_sz%C3%A9nhidrog%C3%A9nek" title="Policiklusos aromás szénhidrogének – Hungarian" lang="hu" hreflang="hu" data-title="Policiklusos aromás szénhidrogének" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Polycyclische_aromatische_koolwaterstoffen" title="Polycyclische aromatische koolwaterstoffen – Dutch" lang="nl" hreflang="nl" data-title="Polycyclische aromatische koolwaterstoffen" 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/%E5%A4%9A%E7%92%B0%E8%8A%B3%E9%A6%99%E6%97%8F%E7%82%AD%E5%8C%96%E6%B0%B4%E7%B4%A0" title="多環芳香族炭化水素 – Japanese" lang="ja" hreflang="ja" data-title="多環芳香族炭化水素" 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/Polysykliske_aromatiske_hydrokarboner" title="Polysykliske aromatiske hydrokarboner – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Polysykliske aromatiske hydrokarboner" 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/Polysykliske_aromatiske_hydrokarbon" title="Polysykliske aromatiske hydrokarbon – Norwegian Nynorsk" lang="nn" hreflang="nn" data-title="Polysykliske aromatiske hydrokarbon" 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-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Wielopier%C5%9Bcieniowe_w%C4%99glowodory_aromatyczne" title="Wielopierścieniowe węglowodory aromatyczne – Polish" lang="pl" hreflang="pl" data-title="Wielopierścieniowe węglowodory aromatyczne" 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/Hidrocarbonetos_arom%C3%A1ticos_polic%C3%ADclicos" title="Hidrocarbonetos aromáticos policíclicos – Portuguese" lang="pt" hreflang="pt" data-title="Hidrocarbonetos aromáticos policíclicos" 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/Hidrocarbur%C4%83_aromatic%C4%83_policiclic%C4%83" title="Hidrocarbură aromatică policiclică – Romanian" lang="ro" hreflang="ro" data-title="Hidrocarbură aromatică policiclică" 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%9F%D0%BE%D0%BB%D0%B8%D1%86%D0%B8%D0%BA%D0%BB%D0%B8%D1%87%D0%B5%D1%81%D0%BA%D0%B8%D0%B5_%D0%B0%D1%80%D0%BE%D0%BC%D0%B0%D1%82%D0%B8%D1%87%D0%B5%D1%81%D0%BA%D0%B8%D0%B5_%D1%83%D0%B3%D0%BB%D0%B5%D0%B2%D0%BE%D0%B4%D0%BE%D1%80%D0%BE%D0%B4%D1%8B" title="Полициклические ароматические углеводороды – Russian" lang="ru" hreflang="ru" data-title="Полициклические ароматические углеводороды" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Polyaromatick%C3%BD_uh%C4%BEovod%C3%ADk" title="Polyaromatický uhľovodík – Slovak" lang="sk" hreflang="sk" data-title="Polyaromatický uhľovodík" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Policikli%C4%8Dni_aromati%C4%8Dni_ugljovodonik" title="Policiklični aromatični ugljovodonik – Serbian" lang="sr" hreflang="sr" data-title="Policiklični aromatični ugljovodonik" 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-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Polysykliset_aromaattiset_hiilivedyt" title="Polysykliset aromaattiset hiilivedyt – Finnish" lang="fi" hreflang="fi" data-title="Polysykliset aromaattiset hiilivedyt" 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/Polycykliska_aromatiska_kolv%C3%A4ten" title="Polycykliska aromatiska kolväten – Swedish" lang="sv" hreflang="sv" data-title="Polycykliska aromatiska kolväten" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B9%82%E0%B8%9E%E0%B8%A5%E0%B8%B5%E0%B9%84%E0%B8%8B%E0%B8%84%E0%B8%A5%E0%B8%B4%E0%B8%81%E0%B8%AD%E0%B8%B0%E0%B9%82%E0%B8%A3%E0%B8%A1%E0%B8%B2%E0%B8%95%E0%B8%B4%E0%B8%81%E0%B9%84%E0%B8%AE%E0%B9%82%E0%B8%94%E0%B8%A3%E0%B8%84%E0%B8%B2%E0%B8%A3%E0%B9%8C%E0%B8%9A%E0%B8%AD%E0%B8%99" title="โพลีไซคลิกอะโรมาติกไฮโดรคาร์บอน – Thai" lang="th" hreflang="th" data-title="โพลีไซคลิกอะโรมาติกไฮโดรคาร์บอน" data-language-autonym="ไทย" data-language-local-name="Thai" class="interlanguage-link-target"><span>ไทย</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Polisiklik_aromatik_hidrokarbon" title="Polisiklik aromatik hidrokarbon – Turkish" lang="tr" hreflang="tr" data-title="Polisiklik aromatik hidrokarbon" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%9F%D0%BE%D0%BB%D1%96%D1%86%D0%B8%D0%BA%D0%BB%D1%96%D1%87%D0%BD%D1%96_%D0%B0%D1%80%D0%BE%D0%BC%D0%B0%D1%82%D0%B8%D1%87%D0%BD%D1%96_%D0%B2%D1%83%D0%B3%D0%BB%D0%B5%D0%B2%D0%BE%D0%B4%D0%BD%D1%96" title="Поліциклічні ароматичні вуглеводні – Ukrainian" lang="uk" hreflang="uk" data-title="Поліциклічні ароматичні вуглеводні" 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/Hydrocarbon_th%C6%A1m_%C4%91a_v%C3%B2ng" title="Hydrocarbon thơm đa vòng – Vietnamese" lang="vi" hreflang="vi" data-title="Hydrocarbon thơm đa vòng" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target"><span>Tiếng Việt</span></a></li><li class="interlanguage-link interwiki-wuu mw-list-item"><a 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dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Hydrocarbon composed of multiple aromatic rings</div> <style data-mw-deduplicate="TemplateStyles:r1237032888/mw-parser-output/.tmulti">.mw-parser-output .tmulti .multiimageinner{display:flex;flex-direction:column}.mw-parser-output .tmulti .trow{display:flex;flex-direction:row;clear:left;flex-wrap:wrap;width:100%;box-sizing:border-box}.mw-parser-output .tmulti .tsingle{margin:1px;float:left}.mw-parser-output .tmulti .theader{clear:both;font-weight:bold;text-align:center;align-self:center;background-color:transparent;width:100%}.mw-parser-output .tmulti .thumbcaption{background-color:transparent}.mw-parser-output .tmulti .text-align-left{text-align:left}.mw-parser-output .tmulti .text-align-right{text-align:right}.mw-parser-output .tmulti .text-align-center{text-align:center}@media all and (max-width:720px){.mw-parser-output .tmulti .thumbinner{width:100%!important;box-sizing:border-box;max-width:none!important;align-items:center}.mw-parser-output .tmulti .trow{justify-content:center}.mw-parser-output .tmulti .tsingle{float:none!important;max-width:100%!important;box-sizing:border-box;text-align:center}.mw-parser-output .tmulti .tsingle .thumbcaption{text-align:left}.mw-parser-output .tmulti .trow>.thumbcaption{text-align:center}}@media screen{html.skin-theme-clientpref-night .mw-parser-output .tmulti .multiimageinner img{background-color:white}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .tmulti .multiimageinner img{background-color:white}}</style><div class="thumb tmulti tright"><div class="thumbinner multiimageinner" style="width:194px;max-width:194px"><div class="trow"><div class="tsingle" style="width:192px;max-width:192px"><div class="thumbimage"><span typeof="mw:File"><a href="/wiki/File:Hexabenzocoronene.svg" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/ac/Hexabenzocoronene.svg/190px-Hexabenzocoronene.svg.png" decoding="async" width="190" height="220" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/ac/Hexabenzocoronene.svg/285px-Hexabenzocoronene.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/ac/Hexabenzocoronene.svg/380px-Hexabenzocoronene.svg.png 2x" data-file-width="152" data-file-height="176" /></a></span></div></div></div><div class="trow"><div class="tsingle" style="width:192px;max-width:192px"><div class="thumbimage"><span typeof="mw:File"><a href="/wiki/File:Hexabenzocoronene-3D-balls.png" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/65/Hexabenzocoronene-3D-balls.png/190px-Hexabenzocoronene-3D-balls.png" decoding="async" width="190" height="214" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/65/Hexabenzocoronene-3D-balls.png/285px-Hexabenzocoronene-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/65/Hexabenzocoronene-3D-balls.png/380px-Hexabenzocoronene-3D-balls.png 2x" data-file-width="1900" data-file-height="2135" /></a></span></div></div></div><div class="trow"><div class="tsingle" style="width:192px;max-width:192px"><div class="thumbimage"><span typeof="mw:File"><a href="/wiki/File:Hexabenzocoronene_AFM.jpg" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/f/fd/Hexabenzocoronene_AFM.jpg/190px-Hexabenzocoronene_AFM.jpg" decoding="async" width="190" height="192" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/fd/Hexabenzocoronene_AFM.jpg/285px-Hexabenzocoronene_AFM.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/fd/Hexabenzocoronene_AFM.jpg/380px-Hexabenzocoronene_AFM.jpg 2x" data-file-width="710" data-file-height="717" /></a></span></div><div class="thumbcaption">Three representations of <a href="/wiki/Hexabenzocoronene" title="Hexabenzocoronene">hexabenzocoronene</a>, a polycyclic aromatic hydrocarbon. Top: standard line-angle schematic, where carbon atoms are represented by the vertices of the hexagons and hydrogen atoms are inferred. Middle: <a href="/wiki/Ball-and-stick_model" title="Ball-and-stick model">ball-and-stick model</a> showing all carbon and hydrogen atoms. Bottom: <a href="/wiki/Atomic_force_microscopy" title="Atomic force microscopy">atomic force microscopy</a> image.</div></div></div></div></div> <p>A <b>polycyclic aromatic hydrocarbon</b> (<b>PAH</b>) is a class of <a href="/wiki/Organic_compound" title="Organic compound">organic compounds</a> that is composed of multiple <a href="/wiki/Aromatic_ring" class="mw-redirect" title="Aromatic ring">aromatic rings</a>. The simplest representative is <a href="/wiki/Naphthalene" title="Naphthalene">naphthalene</a>, having two aromatic rings, and the three-ring compounds <a href="/wiki/Anthracene" title="Anthracene">anthracene</a> and <a href="/wiki/Phenanthrene" title="Phenanthrene">phenanthrene</a>. PAHs are uncharged, non-polar and planar. Many are colorless. Many of them are found in <a href="/wiki/Coal" title="Coal">coal</a> and in <a href="/wiki/Petroleum" title="Petroleum">oil</a> deposits, and are also produced by the incomplete combustion of <a href="/wiki/Organic_matter" title="Organic matter">organic matter</a>—for example, in engines and incinerators or when biomass burns in <a href="/wiki/Forest_fires" class="mw-redirect" title="Forest fires">forest fires</a>. </p><p>Polycyclic aromatic hydrocarbons are discussed as possible <a href="/wiki/PAH_world_hypothesis" title="PAH world hypothesis">starting materials</a> for <a href="/wiki/Abiotic" class="mw-redirect" title="Abiotic">abiotic</a> syntheses of <a href="/wiki/Material" title="Material">materials</a> required by the <a href="/wiki/Abiogenesis#PAH_world_hypothesis" title="Abiogenesis">earliest forms of life</a>.<sup id="cite_ref-NASA-20140221_1-0" class="reference"><a href="#cite_note-NASA-20140221-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-NASA-20110413_2-0" class="reference"><a href="#cite_note-NASA-20110413-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Nomenclature_and_structure">Nomenclature and structure</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Polycyclic_aromatic_hydrocarbon&action=edit&section=1" title="Edit section: Nomenclature and structure"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The terms <b>polyaromatic hydrocarbon</b>,<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> or <b>polynuclear aromatic hydrocarbon</b><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> (abbreviated as PNA) are also used for this concept.<sup id="cite_ref-ATSDR2011a_5-0" class="reference"><a href="#cite_note-ATSDR2011a-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p><p>By definition, polycyclic aromatic hydrocarbons have multiple aromatic rings, precluding <a href="/wiki/Benzene" title="Benzene">benzene</a> from being considered a PAH. Some sources, such as the <a href="/wiki/United_States_Environmental_Protection_Agency" title="United States Environmental Protection Agency">US EPA</a> and <a href="/wiki/Centers_for_Disease_Control_and_Prevention" title="Centers for Disease Control and Prevention">CDC</a>, consider <a href="/wiki/Naphthalene" title="Naphthalene">naphthalene</a> to be the simplest PAH.<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> Other authors consider PAHs to start with the tricyclic species <a href="/wiki/Phenanthrene" title="Phenanthrene">phenanthrene</a> and <a href="/wiki/Anthracene" title="Anthracene">anthracene</a>.<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> Most authors exclude compounds that include <a href="/wiki/Heteroatom" title="Heteroatom">heteroatoms</a> in the rings, or carry <a href="/wiki/Substituent" title="Substituent">substituents</a>.<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p><p>A polyaromatic hydrocarbon may have rings of various sizes, including some that are not aromatic. Those that have only six-membered rings are said to be <b>alternant</b>.<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p><p>The following are examples of PAHs that vary in the number and arrangement of their rings: </p> <ul class="gallery mw-gallery-traditional"> <li class="gallerycaption">Examples of polycyclic aromatic hydrocarbons</li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Naphthalene-2D-Skeletal.svg" class="mw-file-description" title="Naphthalene"><img alt="Naphthalene" src="//upload.wikimedia.org/wikipedia/commons/thumb/4/4f/Naphthalene-2D-Skeletal.svg/120px-Naphthalene-2D-Skeletal.svg.png" decoding="async" width="120" height="70" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/4f/Naphthalene-2D-Skeletal.svg/180px-Naphthalene-2D-Skeletal.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/4f/Naphthalene-2D-Skeletal.svg/240px-Naphthalene-2D-Skeletal.svg.png 2x" data-file-width="597" data-file-height="348" /></a></span></div> <div class="gallerytext"> <a href="/wiki/Naphthalene" title="Naphthalene">Naphthalene</a></div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Biphenyl.svg" class="mw-file-description" title="Biphenyl"><img alt="Biphenyl" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/2b/Biphenyl.svg/120px-Biphenyl.svg.png" decoding="async" width="120" height="52" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/2b/Biphenyl.svg/180px-Biphenyl.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/2b/Biphenyl.svg/240px-Biphenyl.svg.png 2x" data-file-width="828" data-file-height="358" /></a></span></div> <div class="gallerytext"> <a href="/wiki/Biphenyl" title="Biphenyl">Biphenyl</a></div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Fluorene.svg" class="mw-file-description" title="Fluorene"><img alt="Fluorene" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/cf/Fluorene.svg/120px-Fluorene.svg.png" decoding="async" width="120" height="60" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/cf/Fluorene.svg/180px-Fluorene.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/cf/Fluorene.svg/240px-Fluorene.svg.png 2x" data-file-width="260" data-file-height="130" /></a></span></div> <div class="gallerytext"> <a href="/wiki/Fluorene" title="Fluorene">Fluorene</a></div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Anthracene.svg" class="mw-file-description" title="Anthracene"><img alt="Anthracene" src="//upload.wikimedia.org/wikipedia/commons/thumb/1/12/Anthracene.svg/120px-Anthracene.svg.png" decoding="async" width="120" height="48" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/12/Anthracene.svg/180px-Anthracene.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/12/Anthracene.svg/240px-Anthracene.svg.png 2x" data-file-width="166" data-file-height="66" /></a></span></div> <div class="gallerytext"> <a href="/wiki/Anthracene" title="Anthracene">Anthracene</a></div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Phenanthrene.svg" class="mw-file-description" title="Phenanthrene"><img alt="Phenanthrene" src="//upload.wikimedia.org/wikipedia/commons/thumb/0/06/Phenanthrene.svg/120px-Phenanthrene.svg.png" decoding="async" width="120" height="63" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/06/Phenanthrene.svg/180px-Phenanthrene.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/06/Phenanthrene.svg/240px-Phenanthrene.svg.png 2x" data-file-width="160" data-file-height="84" /></a></span></div> <div class="gallerytext"> <a href="/wiki/Phenanthrene" title="Phenanthrene">Phenanthrene</a></div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Phenalene.svg" class="mw-file-description" title="Phenalene"><img alt="Phenalene" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a5/Phenalene.svg/112px-Phenalene.svg.png" decoding="async" width="112" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a5/Phenalene.svg/168px-Phenalene.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a5/Phenalene.svg/224px-Phenalene.svg.png 2x" data-file-width="195" data-file-height="209" /></a></span></div> <div class="gallerytext"> <a href="/wiki/Phenalene" title="Phenalene">Phenalene</a></div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Tetracene.svg" class="mw-file-description" title="Tetracene"><img alt="Tetracene" src="//upload.wikimedia.org/wikipedia/commons/thumb/8/88/Tetracene.svg/120px-Tetracene.svg.png" decoding="async" width="120" height="35" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/88/Tetracene.svg/180px-Tetracene.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/88/Tetracene.svg/240px-Tetracene.svg.png 2x" data-file-width="239" data-file-height="70" /></a></span></div> <div class="gallerytext"> <a href="/wiki/Tetracene" title="Tetracene">Tetracene</a></div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Chrysene.svg" class="mw-file-description" title="Chrysene"><img alt="Chrysene" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/eb/Chrysene.svg/120px-Chrysene.svg.png" decoding="async" width="120" height="69" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/eb/Chrysene.svg/180px-Chrysene.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/eb/Chrysene.svg/240px-Chrysene.svg.png 2x" data-file-width="192" data-file-height="111" /></a></span></div> <div class="gallerytext"> <a href="/wiki/Chrysene" title="Chrysene">Chrysene</a></div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Triphenylene.svg" class="mw-file-description" title="Triphenylene"><img alt="Triphenylene" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a6/Triphenylene.svg/120px-Triphenylene.svg.png" decoding="async" width="120" height="104" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a6/Triphenylene.svg/180px-Triphenylene.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a6/Triphenylene.svg/240px-Triphenylene.svg.png 2x" data-file-width="512" data-file-height="443" /></a></span></div> <div class="gallerytext"> <a href="/wiki/Triphenylene" title="Triphenylene">Triphenylene</a></div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Pyrene.svg" class="mw-file-description" title="Pyrene"><img alt="Pyrene" src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0a/Pyrene.svg/120px-Pyrene.svg.png" decoding="async" width="120" height="119" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0a/Pyrene.svg/180px-Pyrene.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/0a/Pyrene.svg/240px-Pyrene.svg.png 2x" data-file-width="596" data-file-height="592" /></a></span></div> <div class="gallerytext"> <a href="/wiki/Pyrene" title="Pyrene">Pyrene</a></div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Pentacene.svg" class="mw-file-description" title="Pentacene"><img alt="Pentacene" src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f5/Pentacene.svg/120px-Pentacene.svg.png" decoding="async" width="120" height="29" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f5/Pentacene.svg/180px-Pentacene.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f5/Pentacene.svg/240px-Pentacene.svg.png 2x" data-file-width="512" data-file-height="125" /></a></span></div> <div class="gallerytext"> <a href="/wiki/Pentacene" title="Pentacene">Pentacene</a></div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Perylene.svg" class="mw-file-description" title="Perylene"><img alt="Perylene" src="//upload.wikimedia.org/wikipedia/commons/thumb/7/73/Perylene.svg/88px-Perylene.svg.png" decoding="async" width="88" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/73/Perylene.svg/131px-Perylene.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/73/Perylene.svg/175px-Perylene.svg.png 2x" data-file-width="114" data-file-height="156" /></a></span></div> <div class="gallerytext"> <a href="/wiki/Perylene" title="Perylene">Perylene</a></div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Benzo-a-pyrene.svg" class="mw-file-description" title="Benzo[a]pyrene"><img alt="Benzo[a]pyrene" src="//upload.wikimedia.org/wikipedia/commons/thumb/f/fa/Benzo-a-pyrene.svg/120px-Benzo-a-pyrene.svg.png" decoding="async" width="120" height="75" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/fa/Benzo-a-pyrene.svg/180px-Benzo-a-pyrene.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/fa/Benzo-a-pyrene.svg/240px-Benzo-a-pyrene.svg.png 2x" data-file-width="981" data-file-height="613" /></a></span></div> <div class="gallerytext"> <a href="/wiki/Benzo(a)pyrene" title="Benzo(a)pyrene">Benzo[<i>a</i>]pyrene</a></div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Corannulene.svg" class="mw-file-description" title="Corannulene"><img alt="Corannulene" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/23/Corannulene.svg/120px-Corannulene.svg.png" decoding="async" width="120" height="112" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/23/Corannulene.svg/180px-Corannulene.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/23/Corannulene.svg/240px-Corannulene.svg.png 2x" data-file-width="150" data-file-height="140" /></a></span></div> <div class="gallerytext"> <a href="/wiki/Corannulene" title="Corannulene">Corannulene</a></div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Benzo(ghi)perilene.png" class="mw-file-description" title="Benzo[ghi]perylene"><img alt="Benzo[ghi]perylene" src="//upload.wikimedia.org/wikipedia/commons/thumb/f/ff/Benzo%28ghi%29perilene.png/120px-Benzo%28ghi%29perilene.png" decoding="async" width="120" height="116" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/ff/Benzo%28ghi%29perilene.png/180px-Benzo%28ghi%29perilene.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/ff/Benzo%28ghi%29perilene.png/240px-Benzo%28ghi%29perilene.png 2x" data-file-width="614" data-file-height="591" /></a></span></div> <div class="gallerytext"> <a href="/wiki/Benzo(ghi)perylene" title="Benzo(ghi)perylene">Benzo[<i>ghi</i>]perylene</a></div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Coronene.svg" class="mw-file-description" title="Coronene"><img alt="Coronene" src="//upload.wikimedia.org/wikipedia/commons/thumb/0/05/Coronene.svg/120px-Coronene.svg.png" decoding="async" width="120" height="113" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/05/Coronene.svg/180px-Coronene.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/05/Coronene.svg/240px-Coronene.svg.png 2x" data-file-width="166" data-file-height="156" /></a></span></div> <div class="gallerytext"> <a href="/wiki/Coronene" title="Coronene">Coronene</a></div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Ovalene.svg" class="mw-file-description" title="Ovalene"><img alt="Ovalene" src="//upload.wikimedia.org/wikipedia/commons/thumb/9/93/Ovalene.svg/120px-Ovalene.svg.png" decoding="async" width="120" height="88" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/93/Ovalene.svg/180px-Ovalene.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/93/Ovalene.svg/240px-Ovalene.svg.png 2x" data-file-width="170" data-file-height="125" /></a></span></div> <div class="gallerytext"> <a href="/wiki/Ovalene" title="Ovalene">Ovalene</a></div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Benzocfluorene.svg" class="mw-file-description" title="Benzo[c]fluorene"><img alt="Benzo[c]fluorene" src="//upload.wikimedia.org/wikipedia/commons/thumb/4/4f/Benzocfluorene.svg/120px-Benzocfluorene.svg.png" decoding="async" width="120" height="118" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/4f/Benzocfluorene.svg/180px-Benzocfluorene.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/4f/Benzocfluorene.svg/240px-Benzocfluorene.svg.png 2x" data-file-width="247" data-file-height="242" /></a></span></div> <div class="gallerytext"> <a href="/wiki/Benzo(c)fluorene" title="Benzo(c)fluorene">Benzo[<i>c</i>]fluorene</a></div> </li> </ul> <div class="mw-heading mw-heading3"><h3 id="Geometry">Geometry</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Polycyclic_aromatic_hydrocarbon&action=edit&section=2" title="Edit section: Geometry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Most PAHs, like naphthalene, anthracene, and coronene, are planar. This geometry is a consequence of the fact that the <a href="/wiki/%CE%A3-bond" class="mw-redirect" title="Σ-bond">σ-bonds</a> that result from the merger of sp<sup>2</sup> <a href="/wiki/Orbital_hybridisation" title="Orbital hybridisation">hybrid orbitals</a> of adjacent carbons lie on the same plane as the carbon atom. Those compounds are <a href="/wiki/Chirality" title="Chirality">achiral</a>, since the plane of the molecule is a symmetry plane. </p><p>In rare cases, PAHs are not planar. In some cases, the non-planarity may be forced by the <a href="/wiki/Topology" title="Topology">topology</a> of the molecule and the stiffness (in length and angle) of the carbon-carbon bonds. For example, unlike <a href="/wiki/Coronene" title="Coronene">coronene</a>, <a href="/wiki/Corannulene" title="Corannulene">corannulene</a> adopts a bowl shape in order to reduce the bond stress. The two possible configurations, concave and convex, are separated by a relatively low energy barrier (about 11 <a href="/wiki/Kilocalorie" class="mw-redirect" title="Kilocalorie">kcal</a>/<a href="/wiki/Mole_(chemistry)" class="mw-redirect" title="Mole (chemistry)">mol</a>).<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p><p>In theory, there are 51 structural isomers of coronene that have six fused benzene rings in a cyclic sequence, with two edge carbons shared between successive rings. All of them must be non-planar and have considerable higher bonding energy (computed to be at least 130 kcal/mol) than coronene; and, as of 2002, none of them had been synthesized.<sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p><p>Other PAHs that might seem to be planar, considering only the carbon skeleton, may be distorted by repulsion or steric hindrance between the <a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a> atoms in their periphery. Benzo[c]phenanthrene, with four rings fused in a "C" shape, has a slight helical distortion due to repulsion between the closest pair of hydrogen atoms in the two extremal rings.<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> This effect also causes distortion of picene.<sup id="cite_ref-echi2007_13-0" class="reference"><a href="#cite_note-echi2007-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> </p><p>Adding another benzene ring to form dibenzo[c,g]phenanthrene creates <a href="/wiki/Steric_hindrance" class="mw-redirect" title="Steric hindrance">steric hindrance</a> between the two extreme hydrogen atoms.<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> Adding two more rings on the same sense yields <a href="/wiki/Helicene" title="Helicene">heptahelicene</a> in which the two extreme rings overlap.<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> These non-planar forms are chiral, and their <a href="/wiki/Enantiomer" title="Enantiomer">enantiomers</a> can be isolated.<sup id="cite_ref-gutm2012_16-0" class="reference"><a href="#cite_note-gutm2012-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Benzenoid_hydrocarbons">Benzenoid hydrocarbons</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Polycyclic_aromatic_hydrocarbon&action=edit&section=3" title="Edit section: Benzenoid hydrocarbons"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The <b>benzenoid hydrocarbons</b> have been defined as condensed polycyclic unsaturated fully-conjugated hydrocarbons whose molecules are essentially planar with all rings six-membered. Full conjugation means that all carbon atoms and carbon-carbon bonds must have the sp<sup>2</sup> structure of benzene. This class is largely a subset of the alternant PAHs, but is considered to include unstable or hypothetical compounds like <a href="/wiki/Triangulene" title="Triangulene">triangulene</a> or <a href="/wiki/Heptacene" title="Heptacene">heptacene</a>.<sup id="cite_ref-gutm2012_16-1" class="reference"><a href="#cite_note-gutm2012-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p><p>As of 2012, over 300 benzenoid hydrocarbons had been isolated and characterized.<sup id="cite_ref-gutm2012_16-2" class="reference"><a href="#cite_note-gutm2012-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Bonding_and_aromaticity">Bonding and aromaticity</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Polycyclic_aromatic_hydrocarbon&action=edit&section=4" title="Edit section: Bonding and aromaticity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></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">See also: <a href="/wiki/Clar%27s_rule" title="Clar's rule">Clar's rule</a></div> <p>The <a href="/wiki/Aromaticity" title="Aromaticity">aromaticity</a> varies for PAHs. According to <a href="/wiki/Clar%27s_rule" title="Clar's rule">Clar's rule</a>,<sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> the <a href="/wiki/Resonance_structure" class="mw-redirect" title="Resonance structure">resonance structure</a> of a PAH that has the largest number of disjoint aromatic <a href="/wiki/Pi_bond" title="Pi bond">pi sextets</a>—i.e. <a href="/wiki/Benzene" title="Benzene">benzene</a>-like moieties—is the most important for the characterization of the properties of that PAH.<sup id="cite_ref-18" class="reference"><a href="#cite_note-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> </p> <ul class="gallery mw-gallery-traditional center"> <li class="gallerycaption">Benzene-substructure resonance analysis for Clar's rule</li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Phenanthrene_Clar_rule.svg" class="mw-file-description" title="Phenanthrene"><img alt="Phenanthrene" src="//upload.wikimedia.org/wikipedia/commons/thumb/7/75/Phenanthrene_Clar_rule.svg/120px-Phenanthrene_Clar_rule.svg.png" decoding="async" width="120" height="46" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/75/Phenanthrene_Clar_rule.svg/180px-Phenanthrene_Clar_rule.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/75/Phenanthrene_Clar_rule.svg/240px-Phenanthrene_Clar_rule.svg.png 2x" data-file-width="275" data-file-height="105" /></a></span></div> <div class="gallerytext">Phenanthrene</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Anthracene_Clar_rule.svg" class="mw-file-description" title="Anthracene"><img alt="Anthracene" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e0/Anthracene_Clar_rule.svg/120px-Anthracene_Clar_rule.svg.png" decoding="async" width="120" height="72" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e0/Anthracene_Clar_rule.svg/180px-Anthracene_Clar_rule.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e0/Anthracene_Clar_rule.svg/240px-Anthracene_Clar_rule.svg.png 2x" data-file-width="100" data-file-height="60" /></a></span></div> <div class="gallerytext">Anthracene</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Chrysene_Clar_rule.svg" class="mw-file-description" title="Chrysene"><img alt="Chrysene" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a3/Chrysene_Clar_rule.svg/120px-Chrysene_Clar_rule.svg.png" decoding="async" width="120" height="85" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a3/Chrysene_Clar_rule.svg/180px-Chrysene_Clar_rule.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a3/Chrysene_Clar_rule.svg/240px-Chrysene_Clar_rule.svg.png 2x" data-file-width="153" data-file-height="108" /></a></span></div> <div class="gallerytext">Chrysene</div> </li> </ul> <p>For example, <a href="/wiki/Phenanthrene" title="Phenanthrene">phenanthrene</a> has two Clar structures: one with just one aromatic sextet (the middle ring), and the other with two (the first and third rings). The latter case is therefore the more characteristic electronic nature of the two. Therefore, in this molecule the outer rings have greater aromatic character whereas the central ring is less aromatic and therefore more reactive.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (June 2014)">citation needed</span></a></i>]</sup> In contrast, in <a href="/wiki/Anthracene" title="Anthracene">anthracene</a> the resonance structures have one sextet each, which can be at any of the three rings, and the aromaticity spreads out more evenly across the whole molecule.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (June 2014)">citation needed</span></a></i>]</sup> This difference in number of sextets is reflected in the differing <a href="/wiki/Ultraviolet%E2%80%93visible_spectroscopy" title="Ultraviolet–visible spectroscopy">ultraviolet–visible spectra</a> of these two isomers, as higher Clar pi-sextets are associated with larger <a href="/wiki/HOMO-LUMO" class="mw-redirect" title="HOMO-LUMO">HOMO-LUMO</a> gaps;<sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> the highest-wavelength absorbance of phenanthrene is at 293 nm, while anthracene is at 374 nm.<sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> Three Clar structures with two sextets each are present in the four-ring <a href="/wiki/Chrysene" title="Chrysene">chrysene</a> structure: one having sextets in the first and third rings, one in the second and fourth rings, and one in the first and fourth rings.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (June 2014)">citation needed</span></a></i>]</sup> Superposition of these structures reveals that the aromaticity in the outer rings is greater (each has a sextet in two of the three Clar structures) compared to the inner rings (each has a sextet in only one of the three). </p> <div class="mw-heading mw-heading2"><h2 id="Properties">Properties</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Polycyclic_aromatic_hydrocarbon&action=edit&section=5" title="Edit section: Properties"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Physicochemical">Physicochemical</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Polycyclic_aromatic_hydrocarbon&action=edit&section=6" title="Edit section: Physicochemical"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>PAHs are <a href="/wiki/Chemical_polarity#Nonpolar_molecules" title="Chemical polarity">nonpolar</a> and <a href="/wiki/Lipophilicity" title="Lipophilicity">lipophilic</a>. Larger PAHs are generally <a href="/wiki/Solubility" title="Solubility">insoluble</a> in water, although some smaller PAHs are soluble.<sup id="cite_ref-21" class="reference"><a href="#cite_note-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-22" class="reference"><a href="#cite_note-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> The larger members are also poorly soluble in <a href="/wiki/Organic_solvent" class="mw-redirect" title="Organic solvent">organic solvents</a> and in <a href="/wiki/Lipid" title="Lipid">lipids</a>. The larger members, e.g. perylene, are strongly colored.<sup id="cite_ref-gutm2012_16-3" class="reference"><a href="#cite_note-gutm2012-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Redox">Redox</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Polycyclic_aromatic_hydrocarbon&action=edit&section=7" title="Edit section: Redox"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Polycyclic aromatic compounds characteristically yield <a href="/wiki/Free_radical" class="mw-redirect" title="Free radical">radicals</a> and <a href="/wiki/Anion" class="mw-redirect" title="Anion">anions</a> upon treatment with alkali metals. The large PAH form dianions as well.<sup id="cite_ref-23" class="reference"><a href="#cite_note-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> The <a href="/wiki/Redox_potential" class="mw-redirect" title="Redox potential">redox potential</a> correlates with the size of the PAH. </p> <dl><dd><table class="wikitable"> <caption><a href="/wiki/Half-cell" title="Half-cell">Half-cell</a> potential of aromatic compounds against the <a href="/wiki/Saturated_calomel_electrode" title="Saturated calomel electrode">SCE</a> (Fc<sup>+/0</sup>)<sup id="cite_ref-24" class="reference"><a href="#cite_note-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> </caption> <tbody><tr> <th>Compound </th> <th>Potential (V) </th></tr> <tr> <td><a href="/wiki/Benzene" title="Benzene">benzene</a> </td> <td>−3.42 </td></tr> <tr> <td><a href="/wiki/Biphenyl" title="Biphenyl">biphenyl</a><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> </td> <td>−2.60 (-3.18) </td></tr> <tr> <td><a href="/wiki/Naphthalene" title="Naphthalene">naphthalene</a> </td> <td>−2.51 (-3.1) </td></tr> <tr> <td><a href="/wiki/Anthracene" title="Anthracene">anthracene</a> </td> <td>−1.96 (-2.5) </td></tr> <tr> <td><a href="/wiki/Phenanthrene" title="Phenanthrene">phenanthrene</a> </td> <td>−2.46 </td></tr> <tr> <td><a href="/wiki/Perylene" title="Perylene">perylene</a> </td> <td>−1.67 (-2.2) </td></tr> <tr> <td><a href="/wiki/Pentacene" title="Pentacene">pentacene</a> </td> <td>−1.35 </td></tr></tbody></table></dd></dl> <div class="mw-heading mw-heading2"><h2 id="Sources">Sources</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Polycyclic_aromatic_hydrocarbon&action=edit&section=8" title="Edit section: Sources"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Artificial">Artificial</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Polycyclic_aromatic_hydrocarbon&action=edit&section=9" title="Edit section: Artificial"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The dominant sources of PAHs in the environment are from human activity: wood-burning and combustion of other <a href="/wiki/Biofuels" class="mw-redirect" title="Biofuels">biofuels</a> such as dung or crop residues contribute more than half of annual global PAH emissions, particularly due to biofuel use in India and China.<sup id="cite_ref-Ramesh2011_26-0" class="reference"><a href="#cite_note-Ramesh2011-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-abdel2016_27-0" class="reference"><a href="#cite_note-abdel2016-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> As of 2004, industrial processes and the extraction and use of <a href="/wiki/Fossil_fuels" class="mw-redirect" title="Fossil fuels">fossil fuels</a> made up slightly more than one quarter of global PAH emissions, dominating outputs in industrial countries such as the United States.<sup id="cite_ref-Ramesh2011_26-1" class="reference"><a href="#cite_note-Ramesh2011-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> </p><p>A year-long sampling campaign in Athens, Greece found a third (31%) of PAH urban <a href="/wiki/Air_pollution" title="Air pollution">air pollution</a> to be caused by wood-burning, like diesel and oil (33%) and gasoline (29%). It also found that wood-burning is responsible for nearly half (43%) of annual PAH cancer-risk (<a href="/wiki/Carcinogen" title="Carcinogen">carcinogenic</a> potential) compared to the other sources and that wintertime PAH levels were 7 times higher than in other seasons, especially if atmospheric dispersion is low.<sup id="cite_ref-28" class="reference"><a href="#cite_note-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup><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> </p><p>Lower-temperature combustion, such as <a href="/wiki/Tobacco_smoking" title="Tobacco smoking">tobacco smoking</a> or <a href="/wiki/Wood-burning" class="mw-redirect" title="Wood-burning">wood-burning</a>, tends to generate low molecular weight PAHs, whereas high-temperature industrial processes typically generate PAHs with higher molecular weights.<sup id="cite_ref-Tobis_30-0" class="reference"><a href="#cite_note-Tobis-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> Incense is also a source.<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> </p><p>PAHs are typically found as complex mixtures.<sup id="cite_ref-ravi2008_32-0" class="reference"><a href="#cite_note-ravi2008-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Tobis_30-1" class="reference"><a href="#cite_note-Tobis-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Natural">Natural</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Polycyclic_aromatic_hydrocarbon&action=edit&section=10" title="Edit section: Natural"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading4"><h4 id="Natural_fires">Natural fires</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Polycyclic_aromatic_hydrocarbon&action=edit&section=11" title="Edit section: Natural fires"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>PAHs may result from the incomplete <a href="/wiki/Combustion" title="Combustion">combustion</a> of <a href="/wiki/Organic_matter" title="Organic matter">organic matter</a> in natural <a href="/wiki/Wildfire" title="Wildfire">wildfires</a>.<sup id="cite_ref-abdel2016_27-1" class="reference"><a href="#cite_note-abdel2016-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Ramesh2011_26-2" class="reference"><a href="#cite_note-Ramesh2011-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> Substantially higher outdoor air, soil, and water concentrations of PAHs have been measured in Asia, Africa, and Latin America than in Europe, Australia, the U.S., and Canada.<sup id="cite_ref-Ramesh2011_26-3" class="reference"><a href="#cite_note-Ramesh2011-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Fossil_carbon">Fossil carbon</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Polycyclic_aromatic_hydrocarbon&action=edit&section=12" title="Edit section: Fossil carbon"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Polycyclic aromatic hydrocarbons are primarily found in natural sources such as <a href="/wiki/Bitumen" title="Bitumen">bitumen</a>.<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-34" class="reference"><a href="#cite_note-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> </p><p>PAHs can also be produced geologically when organic sediments are chemically transformed into <a href="/wiki/Fossil_fuel" title="Fossil fuel">fossil fuels</a> such as oil and <a href="/wiki/Coal" title="Coal">coal</a>.<sup id="cite_ref-ravi2008_32-1" class="reference"><a href="#cite_note-ravi2008-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> The rare minerals <a href="/wiki/Idrialite" title="Idrialite">idrialite</a>, <a href="/wiki/Curtisite" class="mw-redirect" title="Curtisite">curtisite</a>, and <a href="/wiki/Carpathite" title="Carpathite">carpathite</a> consist almost entirely of PAHs that originated from such sediments, that were extracted, processed, separated, and deposited by very hot fluids.<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><sup id="cite_ref-echi2007_13-1" class="reference"><a href="#cite_note-echi2007-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup><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> High levels of such PAHs have been detected in the <a href="/wiki/Cretaceous-Tertiary_boundary" class="mw-redirect" title="Cretaceous-Tertiary boundary">Cretaceous-Tertiary (K-T) boundary</a>, more than 100 times the level in adjacent layers. The spike was attributed to massive fires that consumed about 20% of the terrestrial above-ground biomass in a very short time.<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> </p> <div class="mw-heading mw-heading4"><h4 id="Extraterrestrial">Extraterrestrial</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Polycyclic_aromatic_hydrocarbon&action=edit&section=13" title="Edit section: Extraterrestrial"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>PAHs are prevalent in the <a href="/wiki/Interstellar_medium" title="Interstellar medium">interstellar medium</a> (ISM) of galaxies in both the nearby and distant Universe and make up a dominant emission mechanism in the mid-infrared wavelength range, containing as much as 10% of the total integrated infrared luminosity of galaxies.<sup id="cite_ref-youtube.com_38-0" class="reference"><a href="#cite_note-youtube.com-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup> PAHs generally trace regions of cold molecular gas, which are optimum environments for the formation of stars.<sup id="cite_ref-youtube.com_38-1" class="reference"><a href="#cite_note-youtube.com-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup> </p><p>NASA's <a href="/wiki/Spitzer_Space_Telescope" title="Spitzer Space Telescope">Spitzer Space Telescope</a> and <a href="/wiki/James_Webb_Space_Telescope" title="James Webb Space Telescope">James Webb Space Telescope</a> include instruments for obtaining both images and spectra of light emitted by PAHs associated with <a href="/wiki/Star_formation" title="Star formation">star formation</a>. These images can trace the surface of star-forming <a href="/wiki/Molecular_cloud" title="Molecular cloud">clouds</a> in our own galaxy or identify star forming galaxies in the distant universe.<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> In June 2013, PAHs were detected in the <a href="/wiki/Upper_atmosphere" title="Upper atmosphere">upper atmosphere</a> of <a href="/wiki/Titan_(moon)" title="Titan (moon)">Titan</a>, the largest <a href="/wiki/Moon" title="Moon">moon</a> of the <a href="/wiki/Planet" title="Planet">planet</a> <a href="/wiki/Saturn" title="Saturn">Saturn</a>.<sup id="cite_ref-40" class="reference"><a href="#cite_note-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Minor_sources">Minor sources</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Polycyclic_aromatic_hydrocarbon&action=edit&section=14" title="Edit section: Minor sources"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Volcanic_eruption" class="mw-redirect" title="Volcanic eruption">Volcanic eruptions</a> may emit PAHs.<sup id="cite_ref-ravi2008_32-2" class="reference"><a href="#cite_note-ravi2008-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> </p><p>Certain PAHs such as <a href="/wiki/Perylene" title="Perylene">perylene</a> can also be generated in <a href="/wiki/Hypoxia_(environmental)" title="Hypoxia (environmental)">anaerobic</a> sediments from existing organic material, although it remains undetermined whether abiotic or microbial processes drive their production.<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><sup id="cite_ref-42" class="reference"><a href="#cite_note-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup><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> </p> <div class="mw-heading mw-heading2"><h2 id="Distribution_in_the_environment">Distribution in the environment</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Polycyclic_aromatic_hydrocarbon&action=edit&section=15" title="Edit section: Distribution in the environment"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Aquatic_environments">Aquatic environments</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Polycyclic_aromatic_hydrocarbon&action=edit&section=16" title="Edit section: Aquatic environments"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Most PAHs are insoluble in water, which limits their mobility in the environment, although PAHs <a href="/wiki/Sorption" title="Sorption">sorb</a> to fine-grained organic-rich <a href="/wiki/Sediment" title="Sediment">sediments</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><sup id="cite_ref-45" class="reference"><a href="#cite_note-45"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-46" class="reference"><a href="#cite_note-46"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Choi-2007_47-0" class="reference"><a href="#cite_note-Choi-2007-47"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup> Aqueous solubility of PAHs decreases approximately <a href="/wiki/Logarithmic_growth" title="Logarithmic growth">logarithmically</a> as <a href="/wiki/Molecular_mass" title="Molecular mass">molecular mass</a> increases.<sup id="cite_ref-Johnsen-2005_48-0" class="reference"><a href="#cite_note-Johnsen-2005-48"><span class="cite-bracket">[</span>48<span class="cite-bracket">]</span></a></sup> </p><p>Two-ringed PAHs, and to a lesser extent three-ringed PAHs, dissolve in water, making them more available for biological uptake and <a href="/wiki/Biodegradation" title="Biodegradation">degradation</a>.<sup id="cite_ref-Choi-2007_47-1" class="reference"><a href="#cite_note-Choi-2007-47"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Johnsen-2005_48-1" class="reference"><a href="#cite_note-Johnsen-2005-48"><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> Further, two- to four-ringed PAHs <a href="/wiki/Volatility_(chemistry)" title="Volatility (chemistry)">volatilize</a> sufficiently to appear in the atmosphere predominantly in gaseous form, although the physical state of four-ring PAHs can depend on temperature.<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><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> In contrast, compounds with five or more rings have low solubility in water and low volatility; they are therefore predominantly in solid <a href="/wiki/State_of_matter" title="State of matter">state</a>, bound to <a href="/wiki/Particulates" title="Particulates">particulate</a> <a href="/wiki/Air_pollution" title="Air pollution">air pollution</a>, <a href="/wiki/Soils" class="mw-redirect" title="Soils">soils</a>, or <a href="/wiki/Sediment" title="Sediment">sediments</a>.<sup id="cite_ref-Choi-2007_47-2" class="reference"><a href="#cite_note-Choi-2007-47"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup> In solid state, these compounds are less accessible for biological uptake or degradation, increasing their persistence in the environment.<sup id="cite_ref-Johnsen-2005_48-2" class="reference"><a href="#cite_note-Johnsen-2005-48"><span class="cite-bracket">[</span>48<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Haritash-2009_52-0" class="reference"><a href="#cite_note-Haritash-2009-52"><span class="cite-bracket">[</span>52<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Human_exposure">Human exposure</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Polycyclic_aromatic_hydrocarbon&action=edit&section=17" title="Edit section: Human exposure"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Human exposure varies across the globe and depends on factors such as smoking rates, fuel types in cooking, and pollution controls on power plants, industrial processes, and vehicles.<sup id="cite_ref-ravi2008_32-3" class="reference"><a href="#cite_note-ravi2008-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Ramesh2011_26-4" class="reference"><a href="#cite_note-Ramesh2011-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Choi2010_53-0" class="reference"><a href="#cite_note-Choi2010-53"><span class="cite-bracket">[</span>53<span class="cite-bracket">]</span></a></sup> Developed countries with stricter air and water pollution controls, cleaner sources of cooking (i.e., gas and electricity vs. coal or biofuels), and prohibitions of public smoking tend to have lower levels of PAH exposure, while developing and undeveloped countries tend to have higher levels.<sup id="cite_ref-ravi2008_32-4" class="reference"><a href="#cite_note-ravi2008-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Ramesh2011_26-5" class="reference"><a href="#cite_note-Ramesh2011-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Choi2010_53-1" class="reference"><a href="#cite_note-Choi2010-53"><span class="cite-bracket">[</span>53<span class="cite-bracket">]</span></a></sup> Surgical smoke plumes have been proven to contain PAHs in several independent research studies.<sup id="cite_ref-54" class="reference"><a href="#cite_note-54"><span class="cite-bracket">[</span>54<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-default-size mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:Kochen_%C3%BCber_offenem_Feuer.JPG" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/7f/Kochen_%C3%BCber_offenem_Feuer.JPG/220px-Kochen_%C3%BCber_offenem_Feuer.JPG" decoding="async" width="220" height="165" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/7f/Kochen_%C3%BCber_offenem_Feuer.JPG/330px-Kochen_%C3%BCber_offenem_Feuer.JPG 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/7f/Kochen_%C3%BCber_offenem_Feuer.JPG/440px-Kochen_%C3%BCber_offenem_Feuer.JPG 2x" data-file-width="4608" data-file-height="3456" /></a><figcaption>A wood-burning open-air cooking <a href="/wiki/Stove" title="Stove">stove</a>. <a href="/wiki/Smoke" title="Smoke">Smoke</a> from solid fuels like <a href="/wiki/Wood" title="Wood">wood</a> is a large source of PAHs globally.</figcaption></figure> <p>Burning solid fuels such as <a href="/wiki/Coal" title="Coal">coal</a> and <a href="/wiki/Biofuel" title="Biofuel">biofuels</a> in the home for cooking and heating is a dominant global source of PAH emissions that in developing countries leads to high levels of exposure to <a href="/wiki/Indoor_air_pollution_in_developing_nations" class="mw-redirect" title="Indoor air pollution in developing nations">indoor particulate air pollution</a> containing PAHs, particularly for women and children who spend more time in the home or cooking.<sup id="cite_ref-Ramesh2011_26-6" class="reference"><a href="#cite_note-Ramesh2011-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-55" class="reference"><a href="#cite_note-55"><span class="cite-bracket">[</span>55<span class="cite-bracket">]</span></a></sup> </p><p>In industrial countries, people who smoke tobacco products, or who are exposed to <a href="/wiki/Passive_smoking" title="Passive smoking">second-hand smoke</a>, are among the most highly exposed groups; <a href="/wiki/Tobacco_smoke" title="Tobacco smoke">tobacco smoke</a> contributes to 90% of indoor PAH levels in the homes of smokers.<sup id="cite_ref-Choi2010_53-2" class="reference"><a href="#cite_note-Choi2010-53"><span class="cite-bracket">[</span>53<span class="cite-bracket">]</span></a></sup> For the general population in developed countries, the diet is otherwise the dominant source of PAH exposure, particularly from smoking or grilling meat or consuming PAHs deposited on plant foods, especially broad-leafed vegetables, during growth.<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> Exposure also occurs through drinking alcohol aged in charred barrels, flavored with peat smoke, or made with roasted grains.<sup id="cite_ref-57" class="reference"><a href="#cite_note-57"><span class="cite-bracket">[</span>57<span class="cite-bracket">]</span></a></sup> PAHs are typically at low concentrations in drinking water.<sup id="cite_ref-Choi2010_53-3" class="reference"><a href="#cite_note-Choi2010-53"><span class="cite-bracket">[</span>53<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Cairo_in_smog.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b7/Cairo_in_smog.jpg/220px-Cairo_in_smog.jpg" decoding="async" width="220" height="165" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b7/Cairo_in_smog.jpg/330px-Cairo_in_smog.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b7/Cairo_in_smog.jpg/440px-Cairo_in_smog.jpg 2x" data-file-width="1183" data-file-height="887" /></a><figcaption><a href="/wiki/Smog" title="Smog">Smog</a> in <a href="/wiki/Cairo" title="Cairo">Cairo</a>. Particulate air pollution, including smog, is a substantial cause of human exposure to PAHs.</figcaption></figure> <p>Emissions from vehicles such as cars and trucks can be a substantial outdoor source of PAHs in particulate air pollution.<sup id="cite_ref-ravi2008_32-5" class="reference"><a href="#cite_note-ravi2008-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Ramesh2011_26-7" class="reference"><a href="#cite_note-Ramesh2011-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> Geographically, major roadways are thus sources of PAHs, which may distribute in the atmosphere or deposit nearby.<sup id="cite_ref-Srogi2007_58-0" class="reference"><a href="#cite_note-Srogi2007-58"><span class="cite-bracket">[</span>58<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Catalytic_converter" title="Catalytic converter">Catalytic converters</a> are estimated to reduce PAH emissions from gasoline-fired vehicles by 25-fold.<sup id="cite_ref-ravi2008_32-6" class="reference"><a href="#cite_note-ravi2008-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> </p><p>People can also be occupationally exposed during work that involves fossil fuels or their derivatives, wood-burning, <a href="/wiki/Carbon_electrode" class="mw-redirect" title="Carbon electrode">carbon electrodes</a>, or exposure to <a href="/wiki/Diesel_exhaust" title="Diesel exhaust">diesel exhaust</a>.<sup id="cite_ref-Boffetta1997_59-0" class="reference"><a href="#cite_note-Boffetta1997-59"><span class="cite-bracket">[</span>59<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Wagner2015_60-0" class="reference"><a href="#cite_note-Wagner2015-60"><span class="cite-bracket">[</span>60<span class="cite-bracket">]</span></a></sup> Industrial activity that can produce and distribute PAHs includes <a href="/wiki/Aluminum" class="mw-redirect" title="Aluminum">aluminum</a>, <a href="/wiki/Iron" title="Iron">iron</a>, and <a href="/wiki/Steel" title="Steel">steel</a> manufacturing; <a href="/wiki/Coal_gasification" title="Coal gasification">coal gasification</a>, <a href="/wiki/Tar" title="Tar">tar</a> distillation, <a href="/wiki/Shale_oil_extraction" title="Shale oil extraction">shale oil extraction</a>; production of <a href="/wiki/Coke_(fuel)" title="Coke (fuel)">coke</a>, <a href="/wiki/Creosote" title="Creosote">creosote</a>, <a href="/wiki/Carbon_black" title="Carbon black">carbon black</a>, and <a href="/wiki/Calcium_carbide" title="Calcium carbide">calcium carbide</a>; road paving and <a href="/wiki/Asphalt_concrete" title="Asphalt concrete">asphalt</a> manufacturing; <a href="/wiki/Rubber" class="mw-redirect" title="Rubber">rubber</a> <a href="/wiki/Tire" title="Tire">tire</a> production; manufacturing or use of <a href="/wiki/Metalworking" title="Metalworking">metal working</a> fluids; and activity of coal or <a href="/wiki/Natural_gas" title="Natural gas">natural gas</a> <a href="/wiki/Power_station" title="Power station">power stations</a>.<sup id="cite_ref-ravi2008_32-7" class="reference"><a href="#cite_note-ravi2008-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Boffetta1997_59-1" class="reference"><a href="#cite_note-Boffetta1997-59"><span class="cite-bracket">[</span>59<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Wagner2015_60-1" class="reference"><a href="#cite_note-Wagner2015-60"><span class="cite-bracket">[</span>60<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Environmental_pollution_and_degradation">Environmental pollution and degradation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Polycyclic_aromatic_hydrocarbon&action=edit&section=18" title="Edit section: Environmental pollution and degradation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:Manripo071210_3.jpg" class="mw-file-description"><img alt="A worker's glove touches a dense patch of black oil on a sandy beach." src="//upload.wikimedia.org/wikipedia/commons/thumb/5/5f/Manripo071210_3.jpg/220px-Manripo071210_3.jpg" decoding="async" width="220" height="165" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/5f/Manripo071210_3.jpg/330px-Manripo071210_3.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/5f/Manripo071210_3.jpg/440px-Manripo071210_3.jpg 2x" data-file-width="1280" data-file-height="960" /></a><figcaption><a href="/wiki/Crude_oil" class="mw-redirect" title="Crude oil">Crude oil</a> on a beach after a 2007 <a href="/wiki/Oil_spill" title="Oil spill">oil spill</a> in Korea.</figcaption></figure> <p>PAHs typically disperse from <a href="/wiki/Urban_area" title="Urban area">urban</a> and <a href="/wiki/Suburban" class="mw-redirect" title="Suburban">suburban</a> <a href="/wiki/Nonpoint_source_pollution" title="Nonpoint source pollution">non-point sources</a> through road <a href="/wiki/Surface_runoff" title="Surface runoff">runoff</a>, <a href="/wiki/Sewage" title="Sewage">sewage</a>, and <a href="/wiki/Atmospheric_circulation" title="Atmospheric circulation">atmospheric circulation</a> and subsequent deposition of particulate air pollution.<sup id="cite_ref-Davis_61-0" class="reference"><a href="#cite_note-Davis-61"><span class="cite-bracket">[</span>61<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Hylland2006_62-0" class="reference"><a href="#cite_note-Hylland2006-62"><span class="cite-bracket">[</span>62<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Soil" title="Soil">Soil</a> and river <a href="/wiki/Sediment" title="Sediment">sediment</a> near industrial sites such as creosote manufacturing facilities can be highly contaminated with PAHs.<sup id="cite_ref-ravi2008_32-8" class="reference"><a href="#cite_note-ravi2008-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Oil_spill" title="Oil spill">Oil spills</a>, creosote, <a href="/wiki/Coal_mining" title="Coal mining">coal mining</a> dust, and other fossil fuel sources can also distribute PAHs in the environment.<sup id="cite_ref-ravi2008_32-9" class="reference"><a href="#cite_note-ravi2008-32"><span class="cite-bracket">[</span>32<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>Two- and three-ringed PAHs can disperse widely while dissolved in water or as gases in the atmosphere, while PAHs with higher molecular weights can disperse locally or regionally adhered to particulate matter that is suspended in air or water until the particles land or settle out of the <a href="/wiki/Water_column" title="Water column">water column</a>.<sup id="cite_ref-ravi2008_32-10" class="reference"><a href="#cite_note-ravi2008-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> PAHs have a strong affinity for <a href="/wiki/Organic_carbon" class="mw-redirect" title="Organic carbon">organic carbon</a>, and thus highly organic sediments in <a href="/wiki/River" title="River">rivers</a>, <a href="/wiki/Lake" title="Lake">lakes</a>, and the <a href="/wiki/Ocean" title="Ocean">ocean</a> can be a substantial sink for PAHs.<sup id="cite_ref-Srogi2007_58-1" class="reference"><a href="#cite_note-Srogi2007-58"><span class="cite-bracket">[</span>58<span class="cite-bracket">]</span></a></sup> </p><p><a href="/wiki/Algae" title="Algae">Algae</a> and some <a href="/wiki/Invertebrate" title="Invertebrate">invertebrates</a> such as <a href="/wiki/Protozoans" class="mw-redirect" title="Protozoans">protozoans</a>, <a href="/wiki/Mollusks" class="mw-redirect" title="Mollusks">mollusks</a>, and many <a href="/wiki/Polychaete" title="Polychaete">polychaetes</a> have limited ability to <a href="/wiki/Metabolism" title="Metabolism">metabolize</a> PAHs and <a href="/wiki/Bioaccumulate" class="mw-redirect" title="Bioaccumulate">bioaccumulate</a> disproportionate concentrations of PAHs in their tissues; however, PAH metabolism can vary substantially across invertebrate species.<sup id="cite_ref-Hylland2006_62-1" class="reference"><a href="#cite_note-Hylland2006-62"><span class="cite-bracket">[</span>62<span class="cite-bracket">]</span></a></sup><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> Most <a href="/wiki/Vertebrate" title="Vertebrate">vertebrates</a> metabolize and excrete PAHs relatively rapidly.<sup id="cite_ref-Hylland2006_62-2" class="reference"><a href="#cite_note-Hylland2006-62"><span class="cite-bracket">[</span>62<span class="cite-bracket">]</span></a></sup> Tissue concentrations of PAHs do not increase (<a href="/wiki/Biomagnify" class="mw-redirect" title="Biomagnify">biomagnify</a>) from the lowest to highest levels of food chains.<sup id="cite_ref-Hylland2006_62-3" class="reference"><a href="#cite_note-Hylland2006-62"><span class="cite-bracket">[</span>62<span class="cite-bracket">]</span></a></sup> </p><p>PAHs transform slowly to a wide range of degradation products. Biological degradation by <a href="/wiki/Microorganism" title="Microorganism">microbes</a> is a dominant form of PAH transformation in the environment.<sup id="cite_ref-Haritash-2009_52-1" class="reference"><a href="#cite_note-Haritash-2009-52"><span class="cite-bracket">[</span>52<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Johnsen2005_65-0" class="reference"><a href="#cite_note-Johnsen2005-65"><span class="cite-bracket">[</span>65<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Detritivore" title="Detritivore">Soil-consuming invertebrates</a> such as <a href="/wiki/Earthworm" title="Earthworm">earthworms</a> speed PAH degradation, either through direct metabolism or by improving the conditions for microbial transformations.<sup id="cite_ref-Johnsen2005_65-1" class="reference"><a href="#cite_note-Johnsen2005-65"><span class="cite-bracket">[</span>65<span class="cite-bracket">]</span></a></sup> Abiotic degradation in the atmosphere and the top layers of surface waters can produce nitrogenated, halogenated, hydroxylated, and oxygenated PAHs; some of these compounds can be more toxic, water-soluble, and mobile than their parent PAHs.<sup id="cite_ref-Hylland2006_62-4" class="reference"><a href="#cite_note-Hylland2006-62"><span class="cite-bracket">[</span>62<span class="cite-bracket">]</span></a></sup><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><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> </p> <div class="mw-heading mw-heading3"><h3 id="Urban_soils">Urban soils</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Polycyclic_aromatic_hydrocarbon&action=edit&section=19" title="Edit section: Urban soils"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The <a href="/wiki/British_Geological_Survey" title="British Geological Survey">British Geological Survey</a> reported the amount and distribution of PAH compounds including parent and alkylated forms in urban soils at 76 locations in <a href="/wiki/Greater_London" title="Greater London">Greater London</a>.<sup id="cite_ref-VaneKim2014_68-0" class="reference"><a href="#cite_note-VaneKim2014-68"><span class="cite-bracket">[</span>68<span class="cite-bracket">]</span></a></sup> The study showed that parent (16 PAH) content ranged from 4 to 67 mg/kg (dry soil weight) and an average PAH concentration of 18 mg/kg (dry soil weight) whereas the total PAH content (33 PAH) ranged from 6 to 88 mg/kg and <a href="/wiki/Fluoranthene" title="Fluoranthene">fluoranthene</a> and <a href="/wiki/Pyrene" title="Pyrene">pyrene</a> were generally the most abundant PAHs.<sup id="cite_ref-VaneKim2014_68-1" class="reference"><a href="#cite_note-VaneKim2014-68"><span class="cite-bracket">[</span>68<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Benzo(a)pyrene" title="Benzo(a)pyrene">Benzo[<i>a</i>]pyrene</a> (B<i>a</i>P), the most toxic of the parent PAHs, is widely considered a key marker PAH for environmental assessments;<sup id="cite_ref-69" class="reference"><a href="#cite_note-69"><span class="cite-bracket">[</span>69<span class="cite-bracket">]</span></a></sup> the normal background concentration of B<i>a</i>P in the London urban sites was 6.9 mg/kg (dry soil weight).<sup id="cite_ref-VaneKim2014_68-2" class="reference"><a href="#cite_note-VaneKim2014-68"><span class="cite-bracket">[</span>68<span class="cite-bracket">]</span></a></sup> <a href="/wiki/London" title="London">London</a> soils contained more stable four- to six-ringed PAHs which were indicative of combustion and pyrolytic sources, such as coal and oil burning and traffic-sourced particulates. However, the overall distribution also suggested that the PAHs in London soils had undergone weathering and been modified by a variety of pre-and post-depositional processes such as volatilization and microbial <a href="/wiki/Biodegradation" title="Biodegradation">biodegradation</a>. </p> <div class="mw-heading mw-heading3"><h3 id="Peatlands">Peatlands</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Polycyclic_aromatic_hydrocarbon&action=edit&section=20" title="Edit section: Peatlands"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Managed <a href="/wiki/Burning" class="mw-redirect" title="Burning">burning</a> of <a href="/wiki/Moorland" title="Moorland">moorland</a> vegetation in the UK has been shown to generate PAHs which become incorporated into the <a href="/wiki/Peat" title="Peat">peat</a> surface.<sup id="cite_ref-VaneRawlins2013_70-0" class="reference"><a href="#cite_note-VaneRawlins2013-70"><span class="cite-bracket">[</span>70<span class="cite-bracket">]</span></a></sup> Burning of moorland vegetation such as <a href="/wiki/Calluna" title="Calluna">heather</a> initially generates high amounts of two- and three-ringed PAHs relative to four- to six-ringed PAHs in surface sediments, however, this pattern is reversed as the lower <a href="/wiki/Molecular_weight" class="mw-redirect" title="Molecular weight">molecular weight</a> PAHs are attenuated by biotic decay and <a href="/wiki/Photodegradation" title="Photodegradation">photodegradation</a>.<sup id="cite_ref-VaneRawlins2013_70-1" class="reference"><a href="#cite_note-VaneRawlins2013-70"><span class="cite-bracket">[</span>70<span class="cite-bracket">]</span></a></sup> Evaluation of the PAH distributions using statistical methods such as principal component analyses (PCA) enabled the study to link the source (burnt moorland) to pathway (suspended stream sediment) to the depositional sink (reservoir bed).<sup id="cite_ref-VaneRawlins2013_70-2" class="reference"><a href="#cite_note-VaneRawlins2013-70"><span class="cite-bracket">[</span>70<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Rivers,_estuarine_and_coastal_sediments"><span id="Rivers.2C_estuarine_and_coastal_sediments"></span>Rivers, estuarine and coastal sediments</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Polycyclic_aromatic_hydrocarbon&action=edit&section=21" title="Edit section: Rivers, estuarine and coastal sediments"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Concentrations of PAHs in river and estuarine <a href="/wiki/Sediment" title="Sediment">sediments</a> vary according to a variety of factors including proximity to municipal and industrial discharge points, wind direction and distance from major urban roadways, as well as tidal regime which controls the diluting effect of generally cleaner marine sediments relative to freshwater discharge.<sup id="cite_ref-Davis_61-1" class="reference"><a href="#cite_note-Davis-61"><span class="cite-bracket">[</span>61<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-VaneHarrison2008_71-0" class="reference"><a href="#cite_note-VaneHarrison2008-71"><span class="cite-bracket">[</span>71<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-VaneChenery2011_72-0" class="reference"><a href="#cite_note-VaneChenery2011-72"><span class="cite-bracket">[</span>72<span class="cite-bracket">]</span></a></sup> Consequently, the concentrations of <a href="/wiki/Pollutants" class="mw-redirect" title="Pollutants">pollutants</a> in estuaries tends to decrease at the river mouth.<sup id="cite_ref-73" class="reference"><a href="#cite_note-73"><span class="cite-bracket">[</span>73<span class="cite-bracket">]</span></a></sup> Understanding of sediment hosted PAHs in estuaries is important for the protection of commercial <a href="/wiki/Fisheries" class="mw-redirect" title="Fisheries">fisheries</a> (such as <a href="/wiki/Mussel" title="Mussel">mussels</a>) and general environmental habitat conservation because PAHs can impact the health of suspension and sediment feeding organism.<sup id="cite_ref-74" class="reference"><a href="#cite_note-74"><span class="cite-bracket">[</span>74<span class="cite-bracket">]</span></a></sup> River-estuary surface sediments in the UK tend to have a lower PAH content than sediments buried 10–60 cm from the surface reflecting lower present day industrial activity combined with improvement in environmental legislation of PAH.<sup id="cite_ref-VaneChenery2011_72-1" class="reference"><a href="#cite_note-VaneChenery2011-72"><span class="cite-bracket">[</span>72<span class="cite-bracket">]</span></a></sup> Typical PAH concentrations in UK estuaries range from about 19 to 16,163 µg/kg (dry sediment weight) in the <a href="/wiki/River_Clyde" title="River Clyde">River Clyde</a> and 626 to 3,766 µg/kg in the <a href="/wiki/River_Mersey" title="River Mersey">River Mersey</a>.<sup id="cite_ref-VaneChenery2011_72-2" class="reference"><a href="#cite_note-VaneChenery2011-72"><span class="cite-bracket">[</span>72<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-VaneHarrison2007_75-0" class="reference"><a href="#cite_note-VaneHarrison2007-75"><span class="cite-bracket">[</span>75<span class="cite-bracket">]</span></a></sup> In general estuarine sediments with a higher natural <a href="/wiki/Total_organic_carbon" title="Total organic carbon">total organic carbon</a> content (TOC) tend to accumulate PAHs due to high <a href="/wiki/Sorption" title="Sorption">sorption</a> capacity of organic matter.<sup id="cite_ref-VaneHarrison2007_75-1" class="reference"><a href="#cite_note-VaneHarrison2007-75"><span class="cite-bracket">[</span>75<span class="cite-bracket">]</span></a></sup> A similar correspondence between PAHs and TOC has also been observed in the sediments of tropical <a href="/wiki/Mangrove" title="Mangrove">mangroves</a> located on the coast of southern China.<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> <div class="mw-heading mw-heading2"><h2 id="Human_health">Human health</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Polycyclic_aromatic_hydrocarbon&action=edit&section=22" title="Edit section: Human health"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Cancer" title="Cancer">Cancer</a> is a primary human health risk of exposure to PAHs.<sup id="cite_ref-Bostrom2002_77-0" class="reference"><a href="#cite_note-Bostrom2002-77"><span class="cite-bracket">[</span>77<span class="cite-bracket">]</span></a></sup> Exposure to PAHs has also been linked with cardiovascular disease and poor fetal development. </p> <div class="mw-heading mw-heading3"><h3 id="Cancer">Cancer</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Polycyclic_aromatic_hydrocarbon&action=edit&section=23" title="Edit section: Cancer"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>PAHs have been linked to <a href="/wiki/Skin_cancer" title="Skin cancer">skin</a>, <a href="/wiki/Lung_cancer" title="Lung cancer">lung</a>, <a href="/wiki/Bladder_cancer" title="Bladder cancer">bladder</a>, <a href="/wiki/Liver_cancer" title="Liver cancer">liver</a>, and <a href="/wiki/Stomach_cancer" title="Stomach cancer">stomach</a> cancers in well-established animal model studies.<sup id="cite_ref-Bostrom2002_77-1" class="reference"><a href="#cite_note-Bostrom2002-77"><span class="cite-bracket">[</span>77<span class="cite-bracket">]</span></a></sup> Specific compounds classified by various agencies as possible or probable human carcinogens are identified in the section "<a class="mw-selflink-fragment" href="#Regulation_and_oversight">Regulation and Oversight</a>" below. </p> <div class="mw-heading mw-heading4"><h4 id="History">History</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Polycyclic_aromatic_hydrocarbon&action=edit&section=24" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Chimney_sweeps.jpg" class="mw-file-description"><img alt="A line drawing of an 18th-century man and boy, the man carrying long tools such as a broom" src="//upload.wikimedia.org/wikipedia/commons/thumb/7/75/Chimney_sweeps.jpg/150px-Chimney_sweeps.jpg" decoding="async" width="150" height="225" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/75/Chimney_sweeps.jpg/225px-Chimney_sweeps.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/75/Chimney_sweeps.jpg/300px-Chimney_sweeps.jpg 2x" data-file-width="1800" data-file-height="2700" /></a><figcaption>An 18th-century drawing of <a href="/wiki/Chimney_sweep" title="Chimney sweep">chimney sweeps</a>.</figcaption></figure> <p>Historically, PAHs contributed substantially to our understanding of adverse health effects from exposures to <a href="/wiki/Pollution" title="Pollution">environmental contaminants</a>, including chemical <a href="/wiki/Carcinogenesis" title="Carcinogenesis">carcinogenesis</a>.<sup id="cite_ref-78" class="reference"><a href="#cite_note-78"><span class="cite-bracket">[</span>78<span class="cite-bracket">]</span></a></sup> In 1775, <a href="/wiki/Percivall_Pott" title="Percivall Pott">Percivall Pott</a>, a surgeon at <a href="/wiki/St_Bartholomew%27s_Hospital" title="St Bartholomew's Hospital">St. Bartholomew's Hospital</a> in London, observed that <a href="/wiki/Chimney_sweeps%27_carcinoma" title="Chimney sweeps' carcinoma">scrotal cancer</a> was unusually common in chimney sweepers and proposed the cause as occupational exposure to <a href="/wiki/Soot" title="Soot">soot</a>.<sup id="cite_ref-Dipple1985_79-0" class="reference"><a href="#cite_note-Dipple1985-79"><span class="cite-bracket">[</span>79<span class="cite-bracket">]</span></a></sup> A century later, <a href="/wiki/Richard_von_Volkmann" title="Richard von Volkmann">Richard von Volkmann</a> reported increased skin cancers in workers of the <a href="/wiki/Coal_tar" title="Coal tar">coal tar</a> industry of Germany, and by the early 1900s increased rates of cancer from exposure to soot and coal tar was widely accepted. In 1915, <a href="/wiki/Yamagiwa_Katsusabur%C5%8D" title="Yamagiwa Katsusaburō">Yamigawa</a> and <a href="/w/index.php?title=K%C5%8Dichi_Ichikawa&action=edit&redlink=1" class="new" title="Kōichi Ichikawa (page does not exist)">Ichicawa</a> were the first to experimentally produce cancers, specifically of the skin, by topically applying coal tar to rabbit ears.<sup id="cite_ref-Dipple1985_79-1" class="reference"><a href="#cite_note-Dipple1985-79"><span class="cite-bracket">[</span>79<span class="cite-bracket">]</span></a></sup> </p><p>In 1922, <a href="/wiki/Ernest_Kennaway" title="Ernest Kennaway">Ernest Kennaway</a> determined that the carcinogenic component of coal tar mixtures was an organic compound consisting of only carbon and hydrogen. This component was later linked to a characteristic <a href="/wiki/Fluorescence" title="Fluorescence">fluorescent</a> pattern that was similar but not identical to <a href="/wiki/Benz(a)anthracene" title="Benz(a)anthracene">benz[<i>a</i>]anthracene</a>, a PAH that was subsequently demonstrated to cause <a href="/wiki/Tumor" class="mw-redirect" title="Tumor">tumors</a>.<sup id="cite_ref-Dipple1985_79-2" class="reference"><a href="#cite_note-Dipple1985-79"><span class="cite-bracket">[</span>79<span class="cite-bracket">]</span></a></sup> Cook, Hewett and <a href="/wiki/Izrael_Hieger" title="Izrael Hieger">Hieger</a> then linked the specific spectroscopic fluorescent profile of <a href="/wiki/Benzo(a)pyrene" title="Benzo(a)pyrene">benzo[<i>a</i>]pyrene</a> to that of the carcinogenic component of coal tar,<sup id="cite_ref-Dipple1985_79-3" class="reference"><a href="#cite_note-Dipple1985-79"><span class="cite-bracket">[</span>79<span class="cite-bracket">]</span></a></sup> the first time that a specific compound from an environmental mixture (coal tar) was demonstrated to be carcinogenic. </p><p>In the 1930s and later, epidemiologists from Japan, the UK, and the US, including <a href="/wiki/Richard_Doll" title="Richard Doll">Richard Doll</a> and various others, reported greater rates of death from <a href="/wiki/Lung_cancer" title="Lung cancer">lung cancer</a> following occupational exposure to PAH-rich environments among workers in <a href="/wiki/Coke_oven" class="mw-redirect" title="Coke oven">coke ovens</a> and <a href="/wiki/Coal_carbonization" class="mw-redirect" title="Coal carbonization">coal carbonization</a> and <a href="/wiki/Gasification" title="Gasification">gasification</a> processes.<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> </p> <div class="mw-heading mw-heading4"><h4 id="Mechanisms_of_carcinogenesis">Mechanisms of carcinogenesis</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Polycyclic_aromatic_hydrocarbon&action=edit&section=25" title="Edit section: Mechanisms of carcinogenesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Benzopyrene_DNA_adduct_1JDG.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d8/Benzopyrene_DNA_adduct_1JDG.png/150px-Benzopyrene_DNA_adduct_1JDG.png" decoding="async" width="150" height="208" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d8/Benzopyrene_DNA_adduct_1JDG.png/225px-Benzopyrene_DNA_adduct_1JDG.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d8/Benzopyrene_DNA_adduct_1JDG.png/300px-Benzopyrene_DNA_adduct_1JDG.png 2x" data-file-width="1131" data-file-height="1566" /></a><figcaption>An <a href="/wiki/Adduct" title="Adduct">adduct</a> formed between a <a href="/wiki/DNA" title="DNA">DNA</a> strand and an <a href="/wiki/(%2B)-Benzo(a)pyrene-7,8-dihydrodiol-9,10-epoxide" title="(+)-Benzo(a)pyrene-7,8-dihydrodiol-9,10-epoxide">epoxide derived from a benzo[<i>a</i>]pyrene</a> molecule (center); such adducts may interfere with normal DNA replication.</figcaption></figure> <p>The structure of a PAH influences whether and how the individual compound is carcinogenic.<sup id="cite_ref-Bostrom2002_77-2" class="reference"><a href="#cite_note-Bostrom2002-77"><span class="cite-bracket">[</span>77<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Baird2005_81-0" class="reference"><a href="#cite_note-Baird2005-81"><span class="cite-bracket">[</span>81<span class="cite-bracket">]</span></a></sup> Some carcinogenic PAHs are <a href="/wiki/Genotoxicity" title="Genotoxicity">genotoxic</a> and induce <a href="/wiki/Mutation" title="Mutation">mutations</a> that initiate cancer; others are not genotoxic and instead affect cancer promotion or progression.<sup id="cite_ref-Baird2005_81-1" class="reference"><a href="#cite_note-Baird2005-81"><span class="cite-bracket">[</span>81<span class="cite-bracket">]</span></a></sup><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> </p><p>PAHs that affect <a href="/wiki/Cancer#Pathophysiology" title="Cancer">cancer initiation</a> are typically first chemically modified by <a href="/wiki/Enzyme" title="Enzyme">enzymes</a> into metabolites that react with DNA, leading to mutations. When the DNA sequence is altered in genes that regulate <a href="/wiki/Mitosis" title="Mitosis">cell replication</a>, cancer can result. Mutagenic PAHs, such as benzo[<i>a</i>]pyrene, usually have four or more aromatic rings as well as a "bay region", a structural pocket that increases reactivity of the molecule to the metabolizing enzymes.<sup id="cite_ref-Xue2005_83-0" class="reference"><a href="#cite_note-Xue2005-83"><span class="cite-bracket">[</span>83<span class="cite-bracket">]</span></a></sup> Mutagenic metabolites of PAHs include <a href="/wiki/Diol" title="Diol">diol</a> epoxides, <a href="/wiki/Quinones" class="mw-redirect" title="Quinones">quinones</a>, and <a href="/wiki/Radical_(chemistry)" title="Radical (chemistry)">radical</a> PAH <a href="/wiki/Cation" class="mw-redirect" title="Cation">cations</a>.<sup id="cite_ref-Xue2005_83-1" class="reference"><a href="#cite_note-Xue2005-83"><span class="cite-bracket">[</span>83<span class="cite-bracket">]</span></a></sup><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><sup id="cite_ref-85" class="reference"><a href="#cite_note-85"><span class="cite-bracket">[</span>85<span class="cite-bracket">]</span></a></sup> These metabolites can bind to DNA at specific sites, forming bulky complexes called <a href="/wiki/DNA_adduct" title="DNA adduct">DNA adducts</a> that can be stable or unstable.<sup id="cite_ref-Dipple1985_79-4" class="reference"><a href="#cite_note-Dipple1985-79"><span class="cite-bracket">[</span>79<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Henkler2012_86-0" class="reference"><a href="#cite_note-Henkler2012-86"><span class="cite-bracket">[</span>86<span class="cite-bracket">]</span></a></sup> Stable adducts may lead to <a href="/wiki/DNA_replication" title="DNA replication">DNA replication</a> errors, while unstable adducts react with the DNA strand, removing a <a href="/wiki/Purine" title="Purine">purine</a> base (either <a href="/wiki/Adenine" title="Adenine">adenine</a> or <a href="/wiki/Guanine" title="Guanine">guanine</a>).<sup id="cite_ref-Henkler2012_86-1" class="reference"><a href="#cite_note-Henkler2012-86"><span class="cite-bracket">[</span>86<span class="cite-bracket">]</span></a></sup> Such mutations, if they are not repaired, can transform genes encoding for normal <a href="/wiki/Cell_signaling" title="Cell signaling">cell signaling</a> proteins into cancer-causing <a href="/wiki/Oncogene" title="Oncogene">oncogenes</a>.<sup id="cite_ref-Baird2005_81-2" class="reference"><a href="#cite_note-Baird2005-81"><span class="cite-bracket">[</span>81<span class="cite-bracket">]</span></a></sup> Quinones can also repeatedly generate <a href="/wiki/Reactive_oxygen_species" title="Reactive oxygen species">reactive oxygen species</a> that may independently damage DNA.<sup id="cite_ref-Xue2005_83-2" class="reference"><a href="#cite_note-Xue2005-83"><span class="cite-bracket">[</span>83<span class="cite-bracket">]</span></a></sup> </p><p>Enzymes in the <a href="/wiki/Cytochrome" title="Cytochrome">cytochrome</a> family (<a href="/wiki/CYP1A1" title="CYP1A1">CYP1A1</a>, <a href="/wiki/CYP1A2" title="CYP1A2">CYP1A2</a>, <a href="/wiki/CYP1B1" title="CYP1B1">CYP1B1</a>) metabolize PAHs to diol epoxides.<sup id="cite_ref-Nebert2004_87-0" class="reference"><a href="#cite_note-Nebert2004-87"><span class="cite-bracket">[</span>87<span class="cite-bracket">]</span></a></sup> PAH exposure can increase production of the cytochrome enzymes, allowing the enzymes to convert PAHs into mutagenic diol epoxides at greater rates.<sup id="cite_ref-Nebert2004_87-1" class="reference"><a href="#cite_note-Nebert2004-87"><span class="cite-bracket">[</span>87<span class="cite-bracket">]</span></a></sup> In this pathway, PAH molecules bind to the <a href="/wiki/Aryl_hydrocarbon_receptor" title="Aryl hydrocarbon receptor">aryl hydrocarbon receptor</a> (AhR) and activate it as a <a href="/wiki/Transcription_factor" title="Transcription factor">transcription factor</a> that increases production of the cytochrome enzymes. The activity of these enzymes may at times conversely protect against PAH toxicity, which is not yet well understood.<sup id="cite_ref-Nebert2004_87-2" class="reference"><a href="#cite_note-Nebert2004-87"><span class="cite-bracket">[</span>87<span class="cite-bracket">]</span></a></sup> </p><p>Low molecular weight PAHs, with two to four aromatic hydrocarbon rings, are more potent as <a href="/wiki/Co-carcinogen" title="Co-carcinogen">co-carcinogens</a> during the promotional stage of cancer. In this stage, an initiated cell (a cell that has retained a carcinogenic mutation in a key gene related to cell replication) is removed from growth-suppressing signals from its neighboring cells and begins to clonally replicate.<sup id="cite_ref-Ramesh2004_88-0" class="reference"><a href="#cite_note-Ramesh2004-88"><span class="cite-bracket">[</span>88<span class="cite-bracket">]</span></a></sup> Low-molecular-weight PAHs that have bay or bay-like regions can dysregulate <a href="/wiki/Gap_junction" title="Gap junction">gap junction</a> channels, interfering with intercellular communication, and also affect <a href="/wiki/Mitogen-activated_protein_kinase" title="Mitogen-activated protein kinase">mitogen-activated protein kinases</a> that activate transcription factors involved in cell proliferation.<sup id="cite_ref-Ramesh2004_88-1" class="reference"><a href="#cite_note-Ramesh2004-88"><span class="cite-bracket">[</span>88<span class="cite-bracket">]</span></a></sup> Closure of gap junction protein channels is a normal precursor to cell division. Excessive closure of these channels after exposure to PAHs results in removing a cell from the normal growth-regulating signals imposed by its local community of cells, thus allowing initiated cancerous cells to replicate. These PAHs do not need to be enzymatically metabolized first. Low molecular weight PAHs are prevalent in the environment, thus posing a significant risk to human health at the promotional phases of cancer. </p> <div class="mw-heading mw-heading3"><h3 id="Cardiovascular_disease">Cardiovascular disease</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Polycyclic_aromatic_hydrocarbon&action=edit&section=26" title="Edit section: Cardiovascular disease"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Adult exposure to PAHs has been linked to <a href="/wiki/Cardiovascular_disease" title="Cardiovascular disease">cardiovascular disease</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> PAHs are among the complex suite of contaminants in <a href="/wiki/Tobacco_smoke" title="Tobacco smoke">tobacco smoke</a> and <a href="/wiki/Particulates" title="Particulates">particulate air pollution</a> and may contribute to cardiovascular disease resulting from such exposures.<sup id="cite_ref-Lewtas2007_90-0" class="reference"><a href="#cite_note-Lewtas2007-90"><span class="cite-bracket">[</span>90<span class="cite-bracket">]</span></a></sup> </p><p>In laboratory experiments, animals exposed to certain PAHs have shown increased development of plaques (<a href="/wiki/Atherogenesis" class="mw-redirect" title="Atherogenesis">atherogenesis</a>) within arteries.<sup id="cite_ref-Ramos2005_91-0" class="reference"><a href="#cite_note-Ramos2005-91"><span class="cite-bracket">[</span>91<span class="cite-bracket">]</span></a></sup> Potential mechanisms for the <a href="/wiki/Pathogenesis" title="Pathogenesis">pathogenesis</a> and development of atherosclerotic plaques may be similar to the mechanisms involved in the carcinogenic and mutagenic properties of PAHs.<sup id="cite_ref-Ramos2005_91-1" class="reference"><a href="#cite_note-Ramos2005-91"><span class="cite-bracket">[</span>91<span class="cite-bracket">]</span></a></sup> A leading hypothesis is that PAHs may activate the cytochrome enzyme <a href="/wiki/CYP1B1" title="CYP1B1">CYP1B1</a> in <a href="/wiki/Vascular_smooth_muscle" title="Vascular smooth muscle">vascular smooth muscle</a> cells. This enzyme then metabolically processes the PAHs to quinone metabolites that bind to DNA in reactive adducts that remove purine bases. The resulting mutations may contribute to unregulated growth of vascular smooth muscle cells or to their migration to the inside of the artery, which are steps in <a href="/wiki/Atheroma" title="Atheroma">plaque</a> formation.<sup id="cite_ref-Lewtas2007_90-1" class="reference"><a href="#cite_note-Lewtas2007-90"><span class="cite-bracket">[</span>90<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Ramos2005_91-2" class="reference"><a href="#cite_note-Ramos2005-91"><span class="cite-bracket">[</span>91<span class="cite-bracket">]</span></a></sup> These quinone metabolites also generate <a href="/wiki/Reactive_oxygen_species" title="Reactive oxygen species">reactive oxygen species</a> that may alter the activity of genes that affect plaque formation.<sup id="cite_ref-Ramos2005_91-3" class="reference"><a href="#cite_note-Ramos2005-91"><span class="cite-bracket">[</span>91<span class="cite-bracket">]</span></a></sup> </p><p><a href="/wiki/Oxidative_stress" title="Oxidative stress">Oxidative stress</a> following PAH exposure could also result in cardiovascular disease by causing <a href="/wiki/Inflammation" title="Inflammation">inflammation</a>, which has been recognized as an important factor in the development of atherosclerosis and cardiovascular disease.<sup id="cite_ref-92" class="reference"><a href="#cite_note-92"><span class="cite-bracket">[</span>92<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-93" class="reference"><a href="#cite_note-93"><span class="cite-bracket">[</span>93<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Biomarker" title="Biomarker">Biomarkers</a> of exposure to PAHs in humans have been associated with inflammatory biomarkers that are recognized as important predictors of cardiovascular disease, suggesting that oxidative stress resulting from exposure to PAHs may be a mechanism of cardiovascular disease in humans.<sup id="cite_ref-94" class="reference"><a href="#cite_note-94"><span class="cite-bracket">[</span>94<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Developmental_impacts">Developmental impacts</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Polycyclic_aromatic_hydrocarbon&action=edit&section=27" title="Edit section: Developmental impacts"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Multiple <a href="/wiki/Epidemiology" title="Epidemiology">epidemiological</a> studies of people living in Europe, the United States, and China have linked <a href="/wiki/Uterus" title="Uterus">in utero</a> exposure to PAHs, through air pollution or parental occupational exposure, with poor fetal growth, reduced immune function, and poorer <a href="/wiki/Neurological" class="mw-redirect" title="Neurological">neurological</a> development, including lower <a href="/wiki/Intelligence_quotient" title="Intelligence quotient">IQ</a>.<sup id="cite_ref-95" class="reference"><a href="#cite_note-95"><span class="cite-bracket">[</span>95<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-96" class="reference"><a href="#cite_note-96"><span class="cite-bracket">[</span>96<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-97" class="reference"><a href="#cite_note-97"><span class="cite-bracket">[</span>97<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-98" class="reference"><a href="#cite_note-98"><span class="cite-bracket">[</span>98<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Regulation_and_oversight">Regulation and oversight</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Polycyclic_aromatic_hydrocarbon&action=edit&section=28" title="Edit section: Regulation and oversight"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Some governmental bodies, including the <a href="/wiki/European_Union" title="European Union">European Union</a> as well as <a href="/wiki/NIOSH" class="mw-redirect" title="NIOSH">NIOSH</a> and the <a href="/wiki/United_States_Environmental_Protection_Agency" title="United States Environmental Protection Agency">United States Environmental Protection Agency</a> (EPA), regulate concentrations of PAHs in air, water, and soil.<sup id="cite_ref-PAHReview_99-0" class="reference"><a href="#cite_note-PAHReview-99"><span class="cite-bracket">[</span>99<span class="cite-bracket">]</span></a></sup> The <a href="/wiki/European_Commission" title="European Commission">European Commission</a> has restricted concentrations of 8 carcinogenic PAHs in consumer products that contact the skin or mouth.<sup id="cite_ref-100" class="reference"><a href="#cite_note-100"><span class="cite-bracket">[</span>100<span class="cite-bracket">]</span></a></sup> </p><p>Priority polycyclic aromatic hydrocarbons identified by the US EPA, the US <a href="/wiki/Agency_for_Toxic_Substances_and_Disease_Registry" title="Agency for Toxic Substances and Disease Registry">Agency for Toxic Substances and Disease Registry</a> (ATSDR), and the <a href="/wiki/European_Food_Safety_Authority" title="European Food Safety Authority">European Food Safety Authority</a> (EFSA) due to their carcinogenicity or genotoxicity and/or ability to be monitored are the following:<sup id="cite_ref-101" class="reference"><a href="#cite_note-101"><span class="cite-bracket">[</span>101<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-102" class="reference"><a href="#cite_note-102"><span class="cite-bracket">[</span>102<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-EFSA_103-0" class="reference"><a href="#cite_note-EFSA-103"><span class="cite-bracket">[</span>103<span class="cite-bracket">]</span></a></sup> </p> <table align="center"> <tbody><tr valign="top"> <td> <table class="wikitable"> <tbody><tr> <th>Compound</th> <th>Agency </th> <th><a href="/wiki/United_States_Environmental_Protection_Agency" title="United States Environmental Protection Agency">EPA</a> <a href="/wiki/Maximum_Contaminant_Level" class="mw-redirect" title="Maximum Contaminant Level">MCL</a> in water [<a href="/wiki/Milligram" class="mw-redirect" title="Milligram">mg</a> <a href="/wiki/Litre" title="Litre">L</a><sup>−1</sup>]<sup id="cite_ref-PAHReview_99-1" class="reference"><a href="#cite_note-PAHReview-99"><span class="cite-bracket">[</span>99<span class="cite-bracket">]</span></a></sup> </th></tr> <tr> <td><a href="/wiki/Acenaphthene" title="Acenaphthene">acenaphthene</a></td> <td>EPA, ATSDR </td> <td> </td></tr> <tr> <td><a href="/wiki/Acenaphthylene" title="Acenaphthylene">acenaphthylene</a></td> <td>EPA, ATSDR </td> <td> </td></tr> <tr> <td><a href="/wiki/Anthracene" title="Anthracene">anthracene</a></td> <td>EPA, ATSDR </td> <td> </td></tr> <tr> <td><a href="/wiki/Benz(a)anthracene" title="Benz(a)anthracene">benz[<i>a</i>]anthracene</a><style data-mw-deduplicate="TemplateStyles:r1041539562">.mw-parser-output .citation{word-wrap:break-word}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}</style><sup class="citation nobold" id="ref_cancerA"><a href="#endnote_cancerA">[A]</a></sup></td> <td>EPA, ATSDR, EFSA </td> <td>0.0001 </td></tr> <tr> <td><a href="/wiki/Benzo(b)fluoranthene" class="mw-redirect" title="Benzo(b)fluoranthene">benzo[<i>b</i>]fluoranthene</a><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1041539562"><sup class="citation nobold" id="ref_cancerA"><a href="#endnote_cancerA">[A]</a></sup></td> <td>EPA, ATSDR, EFSA </td> <td>0.0002 </td></tr> <tr> <td><a href="/wiki/Benzo(j)fluoranthene" title="Benzo(j)fluoranthene">benzo[<i>j</i>]fluoranthene</a></td> <td>ATSDR, EFSA </td> <td> </td></tr> <tr> <td><a href="/wiki/Benzo(k)fluoranthene" title="Benzo(k)fluoranthene">benzo[<i>k</i>]fluoranthene</a><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1041539562"><sup class="citation nobold" id="ref_cancerA"><a href="#endnote_cancerA">[A]</a></sup></td> <td>EPA, ATSDR, EFSA </td> <td>0.0002 </td></tr> <tr> <td><a href="/wiki/Benzo(c)fluorene" title="Benzo(c)fluorene">benzo[<i>c</i>]fluorene</a></td> <td>EFSA </td> <td> </td></tr> <tr> <td><a href="/wiki/Benzo(ghi)perylene" title="Benzo(ghi)perylene">benzo[<i>ghi</i>]perylene</a><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1041539562"><sup class="citation nobold" id="ref_cancerA"><a href="#endnote_cancerA">[A]</a></sup></td> <td>EPA, ATSDR, EFSA </td> <td> </td></tr> <tr> <td><a href="/wiki/Benzo(a)pyrene" title="Benzo(a)pyrene">benzo[<i>a</i>]pyrene</a><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1041539562"><sup class="citation nobold" id="ref_cancerA"><a href="#endnote_cancerA">[A]</a></sup></td> <td>EPA, ATSDR, EFSA </td> <td>0.0002 </td></tr> <tr> <td><a href="/wiki/Benzo(e)pyrene" title="Benzo(e)pyrene">benzo[<i>e</i>]pyrene</a></td> <td>ATSDR </td> <td> </td></tr> <tr> <td><a href="/wiki/Chrysene" title="Chrysene">chrysene</a><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1041539562"><sup class="citation nobold" id="ref_cancerA"><a href="#endnote_cancerA">[A]</a></sup></td> <td>EPA, ATSDR, EFSA </td> <td>0.0002 </td></tr> <tr> <td><a href="/wiki/Coronene" title="Coronene">coronene</a></td> <td>ATSDR </td> <td> </td></tr></tbody></table> </td> <td></td> <td> </td> <td> <table class="wikitable"> <tbody><tr> <th>Compound</th> <th>Agency </th> <th><a href="/wiki/United_States_Environmental_Protection_Agency" title="United States Environmental Protection Agency">EPA</a> <a href="/wiki/Maximum_Contaminant_Level" class="mw-redirect" title="Maximum Contaminant Level">MCL</a> in water [<a href="/wiki/Milligram" class="mw-redirect" title="Milligram">mg</a> <a href="/wiki/Litre" title="Litre">L</a><sup>−1</sup>]<sup id="cite_ref-PAHReview_99-2" class="reference"><a href="#cite_note-PAHReview-99"><span class="cite-bracket">[</span>99<span class="cite-bracket">]</span></a></sup> </th></tr> <tr> <td><a href="/w/index.php?title=Cyclopenta(cd)pyrene&action=edit&redlink=1" class="new" title="Cyclopenta(cd)pyrene (page does not exist)">cyclopenta[<i>cd</i>]pyrene</a></td> <td>EFSA </td> <td> </td></tr> <tr> <td><a href="/wiki/Dibenz(a,h)anthracene" title="Dibenz(a,h)anthracene">dibenz[<i>a,h</i>]anthracene</a><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1041539562"><sup class="citation nobold" id="ref_cancerA"><a href="#endnote_cancerA">[A]</a></sup></td> <td>EPA, ATSDR, EFSA </td> <td>0.0003 </td></tr> <tr> <td><a href="/wiki/Dibenzopyrenes" title="Dibenzopyrenes">dibenzo[<i>a,e</i>]pyrene</a></td> <td>EFSA </td> <td> </td></tr> <tr> <td><a href="/wiki/Dibenzopyrenes" title="Dibenzopyrenes">dibenzo[<i>a,h</i>]pyrene</a></td> <td>EFSA </td> <td> </td></tr> <tr> <td><a href="/wiki/Dibenzopyrenes" title="Dibenzopyrenes">dibenzo[<i>a,i</i>]pyrene</a></td> <td>EFSA </td> <td> </td></tr> <tr> <td><a href="/wiki/Dibenzopyrenes" title="Dibenzopyrenes">dibenzo[<i>a,l</i>]pyrene</a></td> <td>EFSA </td> <td> </td></tr> <tr> <td><a href="/wiki/Fluoranthene" title="Fluoranthene">fluoranthene</a></td> <td>EPA, ATSDR </td> <td> </td></tr> <tr> <td><a href="/wiki/Fluorene" title="Fluorene">fluorene</a></td> <td>EPA, ATSDR </td> <td> </td></tr> <tr> <td><a href="/wiki/Indeno(1,2,3-cd)pyrene" title="Indeno(1,2,3-cd)pyrene">indeno[1,2,3-<i>cd</i>]pyrene</a><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1041539562"><sup class="citation nobold" id="ref_cancerA"><a href="#endnote_cancerA">[A]</a></sup></td> <td>EPA, ATSDR, EFSA </td> <td>0.0004 </td></tr> <tr> <td>5-methylchrysene</td> <td>EFSA </td> <td> </td></tr> <tr> <td><a href="/wiki/Naphthalene" title="Naphthalene">naphthalene</a></td> <td>EPA </td> <td> </td></tr> <tr> <td><a href="/wiki/Phenanthrene" title="Phenanthrene">phenanthrene</a></td> <td>EPA, ATSDR </td> <td> </td></tr> <tr> <td><a href="/wiki/Pyrene" title="Pyrene">pyrene</a></td> <td>EPA, ATSDR </td> <td> </td></tr></tbody></table> </td></tr></tbody></table> <dl><dd><dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1041539562"><span class="citation wikicite" id="endnote_cancerA"><a href="#ref_cancerA"><b><sup>A</sup></b></a></span> Considered probable or possible human carcinogens by the US EPA, the European Union, and/or the <a href="/wiki/International_Agency_for_Research_on_Cancer" title="International Agency for Research on Cancer">International Agency for Research on Cancer</a> (IARC).<sup id="cite_ref-EFSA_103-1" class="reference"><a href="#cite_note-EFSA-103"><span class="cite-bracket">[</span>103<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-ATSDR2011a_5-1" class="reference"><a href="#cite_note-ATSDR2011a-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup></dd></dl></dd></dl> <div class="mw-heading mw-heading2"><h2 id="Detection_and_optical_properties">Detection and optical properties</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Polycyclic_aromatic_hydrocarbon&action=edit&section=29" title="Edit section: Detection and optical properties"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>A spectral database exists<sup id="cite_ref-NASA-20140221_1-1" class="reference"><a href="#cite_note-NASA-20140221-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> for tracking polycyclic aromatic hydrocarbons (PAHs) in the <a href="/wiki/Universe" title="Universe">universe</a>.<sup id="cite_ref-104" class="reference"><a href="#cite_note-104"><span class="cite-bracket">[</span>104<span class="cite-bracket">]</span></a></sup> Detection of PAHs in materials is often done using <a href="/wiki/Gas_chromatography-mass_spectrometry" class="mw-redirect" title="Gas chromatography-mass spectrometry">gas chromatography-mass spectrometry</a> or <a href="/wiki/Liquid_chromatography" class="mw-redirect" title="Liquid chromatography">liquid chromatography</a> with <a href="/wiki/Ultraviolet-visible_spectroscopy" class="mw-redirect" title="Ultraviolet-visible spectroscopy">ultraviolet-visible</a> or <a href="/wiki/Fluorescence_spectroscopy" title="Fluorescence spectroscopy">fluorescence</a> spectroscopic methods or by using rapid test PAH indicator strips. Structures of PAHs have been analyzed using infrared spectroscopy.<sup id="cite_ref-105" class="reference"><a href="#cite_note-105"><span class="cite-bracket">[</span>105<span class="cite-bracket">]</span></a></sup> </p><p>PAHs possess very characteristic <a href="/wiki/Ultraviolet-visible_spectroscopy" class="mw-redirect" title="Ultraviolet-visible spectroscopy">UV absorbance spectra</a>. These often possess many absorbance bands and are unique for each ring structure. Thus, for a set of <a href="/wiki/Isomer" title="Isomer">isomers</a>, each isomer has a different UV absorbance spectrum than the others. This is particularly useful in the identification of PAHs. Most PAHs are also <a href="/wiki/Fluorescent" class="mw-redirect" title="Fluorescent">fluorescent</a>, emitting characteristic wavelengths of light when they are excited (when the molecules absorb light). The extended pi-electron electronic structures of PAHs lead to these spectra, as well as to certain large PAHs also exhibiting <a href="/wiki/Semiconductor" title="Semiconductor">semi-conducting</a> and other behaviors. </p> <div class="mw-heading mw-heading3"><h3 id="Origins_of_life">Origins of life</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Polycyclic_aromatic_hydrocarbon&action=edit&section=30" title="Edit section: Origins of life"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/PAH_world_hypothesis" title="PAH world hypothesis">PAH world hypothesis</a></div> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:PIA22568-CatsPawNebula-Spitzer-20181023.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/64/PIA22568-CatsPawNebula-Spitzer-20181023.jpg/300px-PIA22568-CatsPawNebula-Spitzer-20181023.jpg" decoding="async" width="300" height="111" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/64/PIA22568-CatsPawNebula-Spitzer-20181023.jpg/450px-PIA22568-CatsPawNebula-Spitzer-20181023.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/64/PIA22568-CatsPawNebula-Spitzer-20181023.jpg/600px-PIA22568-CatsPawNebula-Spitzer-20181023.jpg 2x" data-file-width="11402" data-file-height="4215" /></a><figcaption><div class="center" style="width:auto; margin-left:auto; margin-right:auto;">The <a href="/wiki/Cat%27s_Paw_Nebula" class="mw-redirect" title="Cat's Paw Nebula">Cat's Paw Nebula</a> lies inside the <a href="/wiki/Milky_Way_Galaxy" class="mw-redirect" title="Milky Way Galaxy">Milky Way Galaxy</a> and is located in the <a href="/wiki/Constellation" title="Constellation">constellation</a> <a href="/wiki/Scorpius" title="Scorpius">Scorpius</a>.<br />Green areas show regions where radiation from hot stars collided with large molecules and small dust grains called "polycyclic aromatic hydrocarbons" (PAHs), causing them to <a href="/wiki/Fluoresce" class="mw-redirect" title="Fluoresce">fluoresce</a>.<br />(<a href="/wiki/Spitzer_Space_Telescope" title="Spitzer Space Telescope">Spitzer Space Telescope</a>, 2018)</div></figcaption></figure> <p>PAHs may be abundant in the universe.<sup id="cite_ref-NASA-20110413_2-1" class="reference"><a href="#cite_note-NASA-20110413-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-106" class="reference"><a href="#cite_note-106"><span class="cite-bracket">[</span>106<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-107" class="reference"><a href="#cite_note-107"><span class="cite-bracket">[</span>107<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-108" class="reference"><a href="#cite_note-108"><span class="cite-bracket">[</span>108<span class="cite-bracket">]</span></a></sup> They seem to have been formed as early as a couple of billion years after the <a href="/wiki/Big_Bang" title="Big Bang">Big Bang</a>, and are associated with <a href="/wiki/Star_formation" title="Star formation">new stars</a> and <a href="/wiki/Exoplanet" title="Exoplanet">exoplanets</a>.<sup id="cite_ref-NASA-20140221_1-2" class="reference"><a href="#cite_note-NASA-20140221-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> More than 20% of the <a href="/wiki/Carbon" title="Carbon">carbon</a> in the universe may be associated with PAHs.<sup id="cite_ref-NASA-20140221_1-3" class="reference"><a href="#cite_note-NASA-20140221-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> PAHs are considered possible <a href="/wiki/PAH_world_hypothesis" title="PAH world hypothesis">starting material</a> for the <a href="/wiki/Abiogenesis#PAH_world_hypothesis" title="Abiogenesis">earliest forms of life</a>.<sup id="cite_ref-NASA-20140221_1-4" class="reference"><a href="#cite_note-NASA-20140221-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-NASA-20110413_2-2" class="reference"><a href="#cite_note-NASA-20110413-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> Light emitted by the <a href="/wiki/Red_Rectangle_nebula" class="mw-redirect" title="Red Rectangle nebula">Red Rectangle nebula</a> possesses spectral signatures that suggest the presence of <a href="/wiki/Anthracene" title="Anthracene">anthracene</a> and <a href="/wiki/Pyrene" title="Pyrene">pyrene</a>.<sup id="cite_ref-Battersby_109-0" class="reference"><a href="#cite_note-Battersby-109"><span class="cite-bracket">[</span>109<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-ReferenceA_110-0" class="reference"><a href="#cite_note-ReferenceA-110"><span class="cite-bracket">[</span>110<span class="cite-bracket">]</span></a></sup> This report was considered a controversial hypothesis that as nebulae of the same type as the Red Rectangle approach the ends of their lives, convection currents cause carbon and hydrogen in the nebulae's cores to get caught in stellar winds, and radiate outward. As they cool, the atoms supposedly bond to each other in various ways and eventually form particles of a million or more atoms. Adolf Witt and his team inferred<sup id="cite_ref-Battersby_109-1" class="reference"><a href="#cite_note-Battersby-109"><span class="cite-bracket">[</span>109<span class="cite-bracket">]</span></a></sup> that PAHs—which may have been vital in the formation of <a href="/wiki/Earliest_known_life_forms" title="Earliest known life forms">early life on Earth</a>—can only originate in nebulae.<sup id="cite_ref-ReferenceA_110-1" class="reference"><a href="#cite_note-ReferenceA-110"><span class="cite-bracket">[</span>110<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:Polycyclic_Aromatic_Hydrocarbons_In_Space.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/Polycyclic_Aromatic_Hydrocarbons_In_Space.jpg/150px-Polycyclic_Aromatic_Hydrocarbons_In_Space.jpg" decoding="async" width="150" height="113" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/Polycyclic_Aromatic_Hydrocarbons_In_Space.jpg/225px-Polycyclic_Aromatic_Hydrocarbons_In_Space.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/Polycyclic_Aromatic_Hydrocarbons_In_Space.jpg/300px-Polycyclic_Aromatic_Hydrocarbons_In_Space.jpg 2x" data-file-width="6000" data-file-height="4500" /></a><figcaption>Two extremely bright stars illuminate a mist of PAHs in this <a href="/wiki/Spitzer_Space_Telescope" title="Spitzer Space Telescope">Spitzer Space Telescope</a> image.<sup id="cite_ref-111" class="reference"><a href="#cite_note-111"><span class="cite-bracket">[</span>111<span class="cite-bracket">]</span></a></sup></figcaption></figure> <p>PAHs, subjected to <a href="/wiki/Interstellar_medium" title="Interstellar medium">interstellar medium (ISM)</a> conditions, are transformed, through <a href="/wiki/Hydrogenation" title="Hydrogenation">hydrogenation</a>, <a href="/wiki/Oxygenate" title="Oxygenate">oxygenation</a>, and <a href="/wiki/Hydroxylation" title="Hydroxylation">hydroxylation</a>, to more complex <a href="/wiki/Organic_compound" title="Organic compound">organic compounds</a>—"a step along the path toward <a href="/wiki/Amino_acid" title="Amino acid">amino acids</a> and <a href="/wiki/Nucleotide" title="Nucleotide">nucleotides</a>, the raw materials of <a href="/wiki/Protein" title="Protein">proteins</a> and <a href="/wiki/DNA" title="DNA">DNA</a>, respectively".<sup id="cite_ref-Space-20120920_112-0" class="reference"><a href="#cite_note-Space-20120920-112"><span class="cite-bracket">[</span>112<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-AJL-20120901_113-0" class="reference"><a href="#cite_note-AJL-20120901-113"><span class="cite-bracket">[</span>113<span class="cite-bracket">]</span></a></sup> Further, as a result of these transformations, the PAHs lose their <a href="/wiki/Spectroscopy" title="Spectroscopy">spectroscopic signature</a> which could be one of the reasons "for the lack of PAH detection in <a href="/wiki/Interstellar_ice" title="Interstellar ice">interstellar ice</a> <a href="/wiki/Cosmic_dust#Dust_grain_formation" title="Cosmic dust">grains</a>, particularly the outer regions of cold, dense clouds or the upper molecular layers of <a href="/wiki/Protoplanetary_disk" title="Protoplanetary disk">protoplanetary disks</a>."<sup id="cite_ref-Space-20120920_112-1" class="reference"><a href="#cite_note-Space-20120920-112"><span class="cite-bracket">[</span>112<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-AJL-20120901_113-1" class="reference"><a href="#cite_note-AJL-20120901-113"><span class="cite-bracket">[</span>113<span class="cite-bracket">]</span></a></sup> </p><p>Low-temperature chemical pathways from simple <a href="/wiki/Organic_compound" title="Organic compound">organic compounds</a> to complex PAHs are of interest. Such chemical pathways may help explain the presence of PAHs in the low-temperature atmosphere of <a href="/wiki/Saturn" title="Saturn">Saturn</a>'s moon <a href="/wiki/Titan_(moon)" title="Titan (moon)">Titan</a>, and may be significant pathways, in terms of the <a href="/wiki/PAH_world_hypothesis" title="PAH world hypothesis">PAH world hypothesis</a>, in producing precursors to biochemicals related to life as we know it.<sup id="cite_ref-114" class="reference"><a href="#cite_note-114"><span class="cite-bracket">[</span>114<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-115" class="reference"><a href="#cite_note-115"><span class="cite-bracket">[</span>115<span class="cite-bracket">]</span></a></sup> </p> <div style="clear:both;" class=""></div> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Polycyclic_aromatic_hydrocarbon&action=edit&section=31" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Chicken_wire_(chemistry)" title="Chicken wire (chemistry)">Chicken wire (chemistry)</a></li> <li><a href="/wiki/F_number_(chemistry)" title="F number (chemistry)">F number</a></li> <li><a href="/wiki/Graphene" title="Graphene">Graphene</a></li> <li><a href="/wiki/Total_petroleum_hydrocarbon" title="Total petroleum hydrocarbon">Total petroleum hydrocarbon</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Polycyclic_aromatic_hydrocarbon&action=edit&section=32" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-NASA-20140221-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-NASA-20140221_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-NASA-20140221_1-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-NASA-20140221_1-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-NASA-20140221_1-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-NASA-20140221_1-4"><sup><i><b>e</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 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font-style: italic;"><a href="https://commons.wikimedia.org/wiki/Category:Polycyclic_aromatic_hydrocarbons" class="extiw" title="commons:Category:Polycyclic aromatic hydrocarbons">Polycyclic aromatic hydrocarbons</a></span>.</div></div> </div> <ul><li><a rel="nofollow" class="external text" href="https://www.atsdr.cdc.gov/csem/pah/index.html">ATSDR - Toxicity of Polycyclic Aromatic Hydrocarbons (PAHs)</a> U.S. Department of Health and Human Services</li> <li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20161012003445/http://www.chem.qmul.ac.uk/iupac/fusedring/">Fused Ring and Bridged Fused Ring Nomenclature</a></li> <li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20050117084624/http://ois.nist.gov/pah/">Database of PAH structures</a></li> <li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20130510152831/http://astrochemistry.ca.astro.it/database/">Cagliari PAH Theoretical Database</a></li> <li><a rel="nofollow" class="external text" href="http://www.astrochem.org/pahdb/">NASA Ames PAH IR Spectroscopic Database</a></li> <li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20060518002254/http://www.npi.gov.au/database/substance-info/profiles/74.html">National Pollutant Inventory: Polycyclic Aromatic Hydrocarbon Fact Sheet</a></li> <li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20060623051810/http://www.spitzer.caltech.edu/features/articles/20050627.shtml">Understanding Polycyclic Aromatic Hydrocarbons</a> NASA Spitzer Space Telescope</li> <li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20110628183505/http://www.astrobio.net/interview/1992/the-aromatic-world">"The Aromatic World: An Interview with Professor Pascale Ehrenfreund"</a> from <i><a href="/wiki/Astrobiology_Magazine" title="Astrobiology Magazine">Astrobiology Magazine</a></i></li> <li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20101206055302/http://oregonstate.edu/superfund/">Oregon State University Superfund Research Center</a> focused on new technologies and emerging health risks of Polycyclic Aromatic Hydrocarbons (PAHs)</li> <li><a rel="nofollow" class="external text" href="http://www.epa.gov/osw/hazard/wastemin/minimize/factshts/pahs.pdf">Polycyclic Aromatic Hydrocarbons (PAHs)--EPA Fact Sheet</a>. 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li a abbr{color:var(--color-base)!important}@media(prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}}@media print{.mw-parser-output .navbar{display:none!important}}</style><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:PAHs" title="Template:PAHs"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:PAHs" title="Template talk:PAHs"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:PAHs" title="Special:EditPage/Template:PAHs"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Polycyclic_aromatic_hydrocarbons" style="font-size:114%;margin:0 4em"><a class="mw-selflink selflink">Polycyclic aromatic hydrocarbons</a></div></th></tr><tr><th scope="row" class="navbox-group" style="text-align: center;;width:1%">2 rings</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/Butalene" title="Butalene">Butalene</a></li> <li><a href="/wiki/Azulene" title="Azulene">Azulene</a></li> <li><a href="/wiki/Naphthalene" title="Naphthalene">Naphthalene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="text-align: center;;width:1%">3 rings</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/Acenaphthene" title="Acenaphthene">Acenaphthene</a></li> <li><a href="/wiki/Acenaphthylene" title="Acenaphthylene">Acenaphthylene</a></li> <li><a href="/wiki/Anthracene" title="Anthracene">Anthracene</a></li> <li><a href="/wiki/Fluorene" title="Fluorene">Fluorene</a></li> <li><a href="/wiki/Phenalene" title="Phenalene">Phenalene</a></li> <li><a href="/wiki/Phenanthrene" title="Phenanthrene">Phenanthrene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="text-align: center;;width:1%">4 rings</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/Benz(a)anthracene" title="Benz(a)anthracene">Benz[<i>a</i>]anthracene</a></li> <li><a href="/wiki/Benzo(a)fluorene" title="Benzo(a)fluorene">Benzo[<i>a</i>]fluorene</a></li> <li><a href="/wiki/Benzo(c)fluorene" title="Benzo(c)fluorene">Benzo[<i>c</i>]fluorene</a></li> <li><a href="/wiki/Benzo(c)phenanthrene" title="Benzo(c)phenanthrene">Benzo[<i>c</i>]phenanthrene</a></li> <li><a href="/wiki/Chrysene" title="Chrysene">Chrysene</a></li> <li><a href="/wiki/Fluoranthene" title="Fluoranthene">Fluoranthene</a></li> <li><a href="/wiki/Pyrene" title="Pyrene">Pyrene</a></li> <li><a href="/wiki/Tetracene" title="Tetracene">Tetracene</a></li> <li><a href="/wiki/Triphenylene" title="Triphenylene">Triphenylene</a></li> <li><a href="/wiki/Tricyclobutabenzene" title="Tricyclobutabenzene">Tricyclobutabenzene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="text-align: center;;width:1%">5 rings</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/Benz(e)acephenanthrylene" title="Benz(e)acephenanthrylene">Benz[<i>e</i>]acephenanthrylene</a></li> <li><a href="/wiki/Benzopyrene" title="Benzopyrene">Benzopyrene</a> <ul><li><a href="/wiki/Benzo(a)pyrene" title="Benzo(a)pyrene">Benzo[<i>a</i>]pyrene</a></li> <li><a href="/wiki/Benzo(e)pyrene" title="Benzo(e)pyrene">Benzo[<i>e</i>]pyrene</a></li> <li><a href="/wiki/Olympicene" title="Olympicene">6<i>H</i>-Benzo[<i>cd</i>]pyrene(Olympicene)</a></li></ul></li> <li><a href="/wiki/Benzo(a)fluoranthene" title="Benzo(a)fluoranthene">Benzo[<i>a</i>]fluoranthene</a></li> <li><a href="/wiki/Benzo(b)fluoranthene" class="mw-redirect" title="Benzo(b)fluoranthene">Benzo[<i>b</i>]fluoranthene</a></li> <li><a href="/wiki/Benzo(j)fluoranthene" title="Benzo(j)fluoranthene">Benzo[<i>j</i>]fluoranthene</a></li> <li><a href="/wiki/Benzo(k)fluoranthene" title="Benzo(k)fluoranthene">Benzo[<i>k</i>]fluoranthene</a></li> <li><a href="/wiki/Bicalicene" title="Bicalicene">trans-Bicalicene</a></li> <li><a href="/wiki/Dibenz(a,h)anthracene" title="Dibenz(a,h)anthracene">Dibenz[<i>a</i>,<i>h</i>]anthracene</a></li> <li><a href="/wiki/Dibenz(a,j)anthracene" title="Dibenz(a,j)anthracene">Dibenz[<i>a</i>,<i>j</i>]anthracene</a></li> <li><a href="/wiki/Pentacene" title="Pentacene">Pentacene</a></li> <li><a href="/w/index.php?title=Pentaphene&action=edit&redlink=1" class="new" title="Pentaphene (page does not exist)">Pentaphene</a></li> <li><a href="/wiki/Perylene" title="Perylene">Perylene</a></li> <li><a href="/wiki/Picene" title="Picene">Picene</a></li> <li><a href="/wiki/Tetraphenylene" title="Tetraphenylene">Tetraphenylene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="text-align: center;;width:1%">6 rings</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/Anthanthrene" title="Anthanthrene">Anthanthrene</a></li> <li><a href="/wiki/Benzo(ghi)perylene" title="Benzo(ghi)perylene">Benzo[<i>ghi</i>]perylene</a></li> <li><a href="/wiki/Corannulene" title="Corannulene">Corannulene</a></li> <li><a href="/wiki/Dibenzopyrenes" title="Dibenzopyrenes">Dibenzopyrenes</a></li> <li><a href="/wiki/Hexacene" title="Hexacene">Hexacene</a></li> <li><a href="/wiki/Triangulene" title="Triangulene">Triangulene</a></li> <li><a href="/wiki/Zethrene" title="Zethrene">Zethrene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="text-align: center;;width:1%">7+ rings</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/Coronene" title="Coronene">Coronene</a></li> <li><a href="/wiki/Dicoronylene" title="Dicoronylene">Dicoronylene</a></li> <li><a href="/wiki/Diindenoperylene" title="Diindenoperylene">Diindenoperylene</a></li> <li><a href="/wiki/Heptacene" title="Heptacene">Heptacene</a></li> <li><a href="/wiki/Hexabenzocoronene" title="Hexabenzocoronene">Hexabenzocoronene</a> (<a href="/wiki/Hexa-cata-hexabenzocoronene" title="Hexa-cata-hexabenzocoronene">Hexa-cata-</a>)</li> <li><a href="/wiki/Kekulene" title="Kekulene">Kekulene</a></li> <li><a href="/wiki/Ovalene" title="Ovalene">Ovalene</a></li> <li><a href="/wiki/Rubicene" title="Rubicene">Rubicene</a></li> <li><a href="/wiki/Rubrene" title="Rubrene">Rubrene</a></li> <li><a href="/wiki/Sumanene" title="Sumanene">Sumanene</a></li> <li><a href="/wiki/Superphenalene" title="Superphenalene">Superphenalene</a></li> <li><a href="/wiki/Trinaphthylene" title="Trinaphthylene">Trinaphthylene</a></li> <li><a href="/wiki/Truxene" title="Truxene">Truxene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="text-align: center;;width:1%">General classes</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/Acene" title="Acene">Acene</a></li> <li><a href="/wiki/Circulene" title="Circulene">Circulene</a></li> <li><a href="/wiki/Cyclacene" title="Cyclacene">Cyclacene</a></li> <li><a href="/wiki/Helicene" title="Helicene">Helicene</a></li> <li><a href="/wiki/Phenacene" title="Phenacene">Phenacene</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Hydrocarbons" 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" style="background:azzurro;"><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:Hydrocarbons" title="Template:Hydrocarbons"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Hydrocarbons" title="Template talk:Hydrocarbons"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Hydrocarbons" title="Special:EditPage/Template:Hydrocarbons"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Hydrocarbons" style="font-size:114%;margin:0 4em"><a href="/wiki/Hydrocarbon" title="Hydrocarbon">Hydrocarbons</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;background:azzurro;">Saturated<br />aliphatic<br />hydrocarbons</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 id="AlkanesCnH2n_+_2" scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Alkane" title="Alkane">Alkanes</a><br />C<sub><i>n</i></sub>H<sub>2<i>n</i> + 2</sub></th><td class="navbox-list-with-group navbox-list navbox-odd" style="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:8.5em">Linear alkanes</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Methane" title="Methane">Methane</a></li> <li><a href="/wiki/Ethane" title="Ethane">Ethane</a></li> <li><a href="/wiki/Propane" title="Propane">Propane</a></li> <li><a href="/wiki/Butane" title="Butane">Butane</a></li> <li><a href="/wiki/Pentane" title="Pentane">Pentane</a></li> <li><a href="/wiki/Hexane" title="Hexane">Hexane</a></li> <li><a href="/wiki/Heptane" title="Heptane">Heptane</a></li> <li><a href="/wiki/Octane" title="Octane">Octane</a></li> <li><a href="/wiki/Nonane" title="Nonane">Nonane</a></li> <li><a href="/wiki/Decane" title="Decane">Decane</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Branched alkanes</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Isobutane" title="Isobutane">Isobutane</a></li> <li><a href="/wiki/Isopentane" title="Isopentane">Isopentane</a></li> <li><a href="/wiki/3-Methylpentane" title="3-Methylpentane">3-Methylpentane</a></li> <li><a href="/wiki/Neopentane" title="Neopentane">Neopentane</a></li> <li><a href="/wiki/2-Methylpentane" title="2-Methylpentane">Isohexane</a></li> <li><a href="/wiki/2-Methylhexane" title="2-Methylhexane">Isoheptane</a></li> <li><a href="/wiki/2,2,4-Trimethylpentane" title="2,2,4-Trimethylpentane">Isooctane</a></li> <li><a href="/wiki/2-Methyloctane" title="2-Methyloctane">Isononane</a></li> <li><a href="/w/index.php?title=Isodecane&action=edit&redlink=1" class="new" title="Isodecane (page does not exist)">Isodecane</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Cycloalkane" title="Cycloalkane">Cycloalkanes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cyclopropane" title="Cyclopropane">Cyclopropane</a></li> <li><a href="/wiki/Cyclobutane" title="Cyclobutane">Cyclobutane</a></li> <li><a href="/wiki/Cyclopentane" title="Cyclopentane">Cyclopentane</a></li> <li><a href="/wiki/Cyclohexane" title="Cyclohexane">Cyclohexane</a></li> <li><a href="/wiki/Cycloheptane" title="Cycloheptane">Cycloheptane</a></li> <li><a href="/wiki/Cyclooctane" title="Cyclooctane">Cyclooctane</a></li> <li><a href="/wiki/Cyclononane" title="Cyclononane">Cyclononane</a></li> <li><a href="/wiki/Cyclodecane" title="Cyclodecane">Cyclodecane</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/w/index.php?title=Alkylcycloalkane&action=edit&redlink=1" class="new" title="Alkylcycloalkane (page does not exist)">Alkylcycloalkanes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Methylcyclopropane" title="Methylcyclopropane">Methylcyclopropane</a></li> <li><a href="/w/index.php?title=Methylcyclobutane&action=edit&redlink=1" class="new" title="Methylcyclobutane (page does not exist)">Methylcyclobutane</a></li> <li><a href="/wiki/Methylcyclopentane" title="Methylcyclopentane">Methylcyclopentane</a></li> <li><a href="/wiki/Methylcyclohexane" title="Methylcyclohexane">Methylcyclohexane</a></li> <li><a href="/w/index.php?title=Isopropylcyclohexane&action=edit&redlink=1" class="new" title="Isopropylcyclohexane (page does not exist)">Isopropylcyclohexane</a></li> <li class="mw-empty-elt"></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/w/index.php?title=Bicycloalkane&action=edit&redlink=1" class="new" title="Bicycloalkane (page does not exist)">Bicycloalkanes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Housane" title="Housane">Housane</a> (bicyclo[2.1.0]pentane)</li> <li><a href="/wiki/Norbornane" title="Norbornane">Norbornane</a> (bicyclo[2.2.1]heptane)</li> <li><a href="/wiki/Decalin" title="Decalin">Decalin</a> (bicyclo[4.4.0]decane)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/w/index.php?title=Polycycloalkane&action=edit&redlink=1" class="new" title="Polycycloalkane (page does not exist)">Polycycloalkanes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Adamantane" title="Adamantane">Adamantane</a></li> <li><a href="/wiki/Diamondoid" title="Diamondoid">Diamondoid</a></li> <li><a href="/w/index.php?title=Perhydrophenanthrene&action=edit&redlink=1" class="new" title="Perhydrophenanthrene (page does not exist)">Perhydrophenanthrene</a></li> <li><a href="/wiki/Sterane" title="Sterane">Sterane</a></li> <li><a href="/wiki/Cubane" title="Cubane">Cubane</a></li> <li><a href="/wiki/Prismane" title="Prismane">Prismane</a></li> <li><a href="/wiki/Dodecahedrane" title="Dodecahedrane">Dodecahedrane</a></li> <li><a href="/wiki/Basketane" title="Basketane">Basketane</a></li> <li><a href="/wiki/Churchane" title="Churchane">Churchane</a></li> <li><a href="/wiki/Pagodane" title="Pagodane">Pagodane</a></li> <li><a href="/wiki/Twistane" title="Twistane">Twistane</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Other</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=Spiroalkane&action=edit&redlink=1" class="new" title="Spiroalkane (page does not exist)">Spiroalkanes</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background:azzurro;"><a href="/wiki/Unsaturated_hydrocarbon" class="mw-redirect" title="Unsaturated hydrocarbon">Unsaturated</a><br />aliphatic<br />hydrocarbons</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:8.5em"><a href="/wiki/Alkene" title="Alkene">Alkenes</a><br />C<sub><i>n</i></sub>H<sub>2<i>n</i></sub></th><td class="navbox-list-with-group navbox-list navbox-odd" style="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:8.5em">Linear alkenes</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Ethylene" title="Ethylene">Ethene</a></li> <li><a href="/wiki/Propene" class="mw-redirect" title="Propene">Propene</a></li> <li><a href="/wiki/Butene" title="Butene">Butene</a></li> <li><a href="/wiki/Pentene" title="Pentene">Pentene</a></li> <li><a href="/wiki/Hexene" title="Hexene">Hexene</a></li> <li><a href="/wiki/Heptene" title="Heptene">Heptene</a></li> <li><a href="/wiki/Octene" title="Octene">Octene</a></li> <li><a href="/wiki/Nonene" title="Nonene">Nonene</a></li> <li><a href="/wiki/Decene" title="Decene">Decene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Branched alkenes</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Isobutylene" title="Isobutylene">Isobutene</a></li> <li><a href="/wiki/Isopentene" class="mw-redirect" title="Isopentene">Isopentene</a></li> <li><a href="/w/index.php?title=Isohexene&action=edit&redlink=1" class="new" title="Isohexene (page does not exist)">Isohexene</a></li> <li><a href="/w/index.php?title=Isoheptene&action=edit&redlink=1" class="new" title="Isoheptene (page does not exist)">Isoheptene</a></li> <li><a href="/w/index.php?title=Isooctene&action=edit&redlink=1" class="new" title="Isooctene (page does not exist)">Isooctene</a></li> <li><a href="/w/index.php?title=Isononene&action=edit&redlink=1" class="new" title="Isononene (page does not exist)">Isononene</a></li> <li><a href="/w/index.php?title=Isodecene&action=edit&redlink=1" class="new" title="Isodecene (page does not exist)">Isodecene</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Alkyne" title="Alkyne">Alkynes</a><br />C<sub><i>n</i></sub>H<sub>2<i>n</i> − 2</sub></th><td class="navbox-list-with-group navbox-list navbox-odd" style="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:8.5em">Linear alkynes</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetylene" title="Acetylene">Ethyne</a></li> <li><a href="/wiki/Propyne" title="Propyne">Propyne</a></li> <li><a href="/wiki/Butyne" title="Butyne">Butyne</a></li> <li><a href="/wiki/Pentyne" title="Pentyne">Pentyne</a></li> <li><a href="/wiki/3-Hexyne" title="3-Hexyne">Hexyne</a></li> <li><a href="/wiki/Heptyne" title="Heptyne">Heptyne</a></li> <li><a href="/wiki/Octyne" title="Octyne">Octyne</a></li> <li><a href="/wiki/Nonyne" title="Nonyne">Nonyne</a></li> <li><a href="/wiki/1-Decyne" title="1-Decyne">Decyne</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Branched alkynes</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=Isopentyne&action=edit&redlink=1" class="new" title="Isopentyne (page does not exist)">Isopentyne</a></li> <li><a href="/w/index.php?title=Isohexyne&action=edit&redlink=1" class="new" title="Isohexyne (page does not exist)">Isohexyne</a></li> <li><a href="/w/index.php?title=Isoheptyne&action=edit&redlink=1" class="new" title="Isoheptyne (page does not exist)">Isoheptyne</a></li> <li><a href="/w/index.php?title=Isooctyne&action=edit&redlink=1" class="new" title="Isooctyne (page does not exist)">Isooctyne</a></li> <li><a href="/w/index.php?title=Isononyne&action=edit&redlink=1" class="new" title="Isononyne (page does not exist)">Isononyne</a></li> <li><a href="/w/index.php?title=Isodecyne&action=edit&redlink=1" class="new" title="Isodecyne (page does not exist)">Isodecyne</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Cycloalkene" title="Cycloalkene">Cycloalkenes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cyclopropene" title="Cyclopropene">Cyclopropene</a></li> <li><a href="/wiki/Cyclobutene" title="Cyclobutene">Cyclobutene</a></li> <li><a href="/wiki/Cyclopentene" title="Cyclopentene">Cyclopentene</a></li> <li><a href="/wiki/Cyclohexene" title="Cyclohexene">Cyclohexene</a></li> <li><a href="/wiki/Cycloheptene" title="Cycloheptene">Cycloheptene</a></li> <li><a href="/wiki/Cyclooctene" title="Cyclooctene">Cyclooctene</a></li> <li><a href="/wiki/Cyclononene" title="Cyclononene">Cyclononene</a></li> <li><a href="/wiki/Cyclodecene" title="Cyclodecene">Cyclodecene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/w/index.php?title=Alkylcycloalkene&action=edit&redlink=1" class="new" title="Alkylcycloalkene (page does not exist)">Alkylcycloalkenes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/1-Methylcyclopropene" title="1-Methylcyclopropene">Methylcyclopropene</a></li> <li><a href="/w/index.php?title=Methylcyclobutene&action=edit&redlink=1" class="new" title="Methylcyclobutene (page does not exist)">Methylcyclobutene</a></li> <li><a href="/w/index.php?title=Methylcyclopentene&action=edit&redlink=1" class="new" title="Methylcyclopentene (page does not exist)">Methylcyclopentene</a></li> <li><a href="/wiki/Methylcyclohexene" title="Methylcyclohexene">Methylcyclohexene</a></li> <li><a href="/w/index.php?title=Isopropylcyclohexene&action=edit&redlink=1" class="new" title="Isopropylcyclohexene (page does not exist)">Isopropylcyclohexene</a></li> <li class="mw-empty-elt"></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/w/index.php?title=Bicycloalkene&action=edit&redlink=1" class="new" title="Bicycloalkene (page does not exist)">Bicycloalkenes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Norbornene" title="Norbornene">Norbornene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Cycloalkyne" title="Cycloalkyne">Cycloalkynes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cyclopropyne" class="mw-redirect" title="Cyclopropyne">Cyclopropyne</a></li> <li><a href="/wiki/Cyclobutyne" title="Cyclobutyne">Cyclobutyne</a></li> <li><a href="/wiki/Cyclopentyne" title="Cyclopentyne">Cyclopentyne</a></li> <li><a href="/w/index.php?title=Cyclohexyne&action=edit&redlink=1" class="new" title="Cyclohexyne (page does not exist)">Cyclohexyne</a></li> <li><a href="/w/index.php?title=Cycloheptyne&action=edit&redlink=1" class="new" title="Cycloheptyne (page does not exist)">Cycloheptyne</a></li> <li><a href="/wiki/Cyclooctyne" title="Cyclooctyne">Cyclooctyne</a></li> <li><a href="/w/index.php?title=Cyclononyne&action=edit&redlink=1" class="new" title="Cyclononyne (page does not exist)">Cyclononyne</a></li> <li><a href="/w/index.php?title=Cyclodecyne&action=edit&redlink=1" class="new" title="Cyclodecyne (page does not exist)">Cyclodecyne</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Diene" title="Diene">Dienes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Propadiene" title="Propadiene">Propadiene</a></li> <li><a href="/wiki/Butadiene" title="Butadiene">Butadiene</a></li> <li><a href="/wiki/Piperylene" title="Piperylene">Pentadiene</a></li> <li><a href="/wiki/1,5-Hexadiene" title="1,5-Hexadiene">Hexadiene</a></li> <li><a href="/w/index.php?title=Heptadiene&action=edit&redlink=1" class="new" title="Heptadiene (page does not exist)">Heptadiene</a></li> <li><a href="/wiki/1,7-Octadiene" title="1,7-Octadiene">Octadiene</a></li> <li><a href="/w/index.php?title=Nonadiene&action=edit&redlink=1" class="new" title="Nonadiene (page does not exist)">Nonadiene</a></li> <li><a href="/w/index.php?title=Decadiene&action=edit&redlink=1" class="new" title="Decadiene (page does not exist)">Decadiene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Other</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=Alkatriene&action=edit&redlink=1" class="new" title="Alkatriene (page does not exist)">Alkatriene</a></li> <li><a href="/w/index.php?title=Alkadiyne&action=edit&redlink=1" class="new" title="Alkadiyne (page does not exist)">Alkadiyne</a></li> <li><a href="/wiki/Cumulene" title="Cumulene">Cumulene</a></li> <li><a href="/wiki/Cyclooctatetraene" title="Cyclooctatetraene">Cyclooctatetraene</a></li> <li><a href="/wiki/Cyclododecatriene" title="Cyclododecatriene">Cyclododecatriene</a></li> <li><a href="/wiki/Enyne" title="Enyne">Enyne</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background:azzurro;"><a href="/wiki/Aromatic_hydrocarbon" class="mw-redirect" title="Aromatic hydrocarbon">Aromatic<br />hydrocarbons</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><th scope="row" class="navbox-group" style="width:8.5em"><a class="mw-selflink selflink">PAHs</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="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:8.5em"><a href="/wiki/Acene" title="Acene">Acenes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Naphthalene" title="Naphthalene">Naphthalene</a></li> <li><a href="/wiki/Anthracene" title="Anthracene">Anthracene</a></li> <li><a href="/wiki/Tetracene" title="Tetracene">Tetracene</a></li> <li><a href="/wiki/Pentacene" title="Pentacene">Pentacene</a></li> <li><a href="/wiki/Hexacene" title="Hexacene">Hexacene</a></li> <li><a href="/wiki/Heptacene" title="Heptacene">Heptacene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Other</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Azulene" title="Azulene">Azulene</a></li> <li><a href="/wiki/Fluorene" title="Fluorene">Fluorene</a></li> <li><a href="/wiki/Helicene" title="Helicene">Helicenes</a></li> <li><a href="/wiki/Circulene" title="Circulene">Circulenes</a></li> <li><a href="/wiki/Butalene" title="Butalene">Butalene</a></li> <li><a href="/wiki/Phenanthrene" title="Phenanthrene">Phenanthrene</a></li> <li><a href="/wiki/Chrysene" title="Chrysene">Chrysene</a></li> <li><a href="/wiki/Pyrene" title="Pyrene">Pyrene</a></li> <li><a href="/wiki/Corannulene" title="Corannulene">Corannulene</a></li> <li><a href="/wiki/Kekulene" title="Kekulene">Kekulene</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Alkylbenzenes" class="mw-redirect" title="Alkylbenzenes">Alkylbenzenes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Toluene" title="Toluene">Toluene</a></li></ul> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/C2-Benzenes" title="C2-Benzenes">C2-Benzenes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="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:8.5em"><a href="/wiki/Xylene" title="Xylene">Xylenes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/O-Xylene" title="O-Xylene"><i>o</i>-Xylene</a></li> <li><a href="/wiki/M-Xylene" title="M-Xylene"><i>m</i>-Xylene</a></li> <li><a href="/wiki/P-Xylene" title="P-Xylene"><i>p</i>-Xylene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Other</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Ethylbenzene" title="Ethylbenzene">Ethylbenzene</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/C3-Benzenes" title="C3-Benzenes">C3-Benzenes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="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:8.5em"><a href="/wiki/Trimethylbenzenes" class="mw-redirect" title="Trimethylbenzenes">Trimethylbenzenes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Mesitylene" title="Mesitylene">Mesitylene</a></li> <li><a href="/wiki/Pseudocumene" class="mw-redirect" title="Pseudocumene">Pseudocumene</a></li> <li><a href="/wiki/Hemellitene" class="mw-redirect" title="Hemellitene">Hemellitene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Other</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cumene" title="Cumene">Cumene</a></li> <li><a href="/wiki/N-Propylbenzene" title="N-Propylbenzene"><i>n</i>-Propylbenzene</a></li> <li><a href="/wiki/4-Ethyltoluene" title="4-Ethyltoluene">4-Ethyltoluene</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/C4-Benzenes" title="C4-Benzenes">C4-Benzenes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="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:8.5em"><a href="/wiki/Cymenes" class="mw-redirect" title="Cymenes">Cymenes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/O-Cymene" title="O-Cymene"><i>o</i>-Cymene</a></li> <li><a href="/wiki/M-Cymene" title="M-Cymene"><i>m</i>-Cymene</a></li> <li><a href="/wiki/P-Cymene" title="P-Cymene"><i>p</i>-Cymene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Tetramethylbenzenes" class="mw-redirect" title="Tetramethylbenzenes">Tetramethylbenzenes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Durene" title="Durene">Durene</a></li> <li><a href="/wiki/Prehnitene" title="Prehnitene">Prehnitene</a></li> <li><a href="/wiki/Isodurene" title="Isodurene">Isodurene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Other</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/N-Butylbenzene" title="N-Butylbenzene"><i>n</i>-Butylbenzene</a></li> <li><a href="/wiki/Sec-Butylbenzene" title="Sec-Butylbenzene"><i>sec</i>-Butylbenzene</a></li> <li><a href="/wiki/Tert-Butylbenzene" title="Tert-Butylbenzene"><i>tert</i>-Butylbenzene</a></li> <li><a href="/wiki/Isobutylbenzene" title="Isobutylbenzene">Isobutylbenzene</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Other</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Hexamethylbenzene" title="Hexamethylbenzene">Hexamethylbenzene</a></li> <li><a href="/wiki/2-Phenylhexane" title="2-Phenylhexane">2-Phenylhexane</a></li> <li><a href="/wiki/1,3,5-Triethylbenzene" title="1,3,5-Triethylbenzene">1,3,5-Triethylbenzene</a></li> <li><a href="/wiki/1,3,5-Triheptylbenzene" title="1,3,5-Triheptylbenzene">1,3,5-Triheptylbenzene</a></li></ul> </div></td></tr></tbody></table><div> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Vinylbenzenes</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Styrene" title="Styrene">Styrene</a></li> <li><a href="/wiki/Divinylbenzene" title="Divinylbenzene">Divinylbenzene</a></li> <li><a href="/wiki/4-Vinyltoluene" title="4-Vinyltoluene">4-Vinyltoluene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Other</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Benzene" title="Benzene">Benzene</a></li> <li><a href="/wiki/Cyclopropenylidene" title="Cyclopropenylidene">Cyclopropenylidene</a></li> <li><a href="/wiki/Phenylacetylene" title="Phenylacetylene">Phenylacetylene</a></li> <li><a href="/wiki/Trans-Propenylbenzene" title="Trans-Propenylbenzene"><i>trans</i>-Propenylbenzene</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background:azzurro;">Other</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/Annulene" title="Annulene">Annulenes</a></li> <li><a href="/wiki/Annulyne" title="Annulyne">Annulynes</a></li> <li><a href="/wiki/Alicyclic_compound" title="Alicyclic compound">Alicyclic compounds</a></li> <li><a href="/wiki/Petroleum_jelly" title="Petroleum jelly">Petroleum jelly</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Consumer_food_safety" style="padding:3px"><table class="nowraplinks hlist mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Consumer_food_safety" title="Template:Consumer food safety"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Consumer_food_safety" title="Template talk:Consumer food safety"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Consumer_food_safety" title="Special:EditPage/Template:Consumer food safety"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Consumer_food_safety" style="font-size:114%;margin:0 4em"><a href="/wiki/Food_safety" title="Food safety">Consumer food safety</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Adulterant" title="Adulterant">Adulterants</a>, <a href="/wiki/Food_contaminant" title="Food contaminant">food contaminants</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/3-MCPD" title="3-MCPD">3-MCPD</a></li> <li><a href="/wiki/Aldicarb" title="Aldicarb">Aldicarb</a></li> <li><a href="/wiki/Antibiotic_use_in_livestock" title="Antibiotic use in livestock">Antibiotic use in livestock</a></li> <li><a href="/wiki/Cyanide" title="Cyanide">Cyanide</a></li> <li><a href="/wiki/Formaldehyde" title="Formaldehyde">Formaldehyde</a></li> <li><a href="/wiki/HGH_controversies" title="HGH controversies">HGH controversies</a></li> <li><a href="/wiki/Lead_poisoning" title="Lead poisoning">Lead poisoning</a></li> <li><a href="/wiki/Melamine" title="Melamine">Melamine</a></li> <li><a href="/wiki/Mercury_in_fish" title="Mercury in fish">Mercury in fish</a></li> <li><a href="/wiki/Sudan_I" title="Sudan I">Sudan I</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Food_additive" title="Food additive">Food additives</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/Flavoring" title="Flavoring">Flavorings</a></li> <li><a href="/wiki/Monosodium_glutamate" title="Monosodium glutamate">Monosodium glutamate (MSG)</a></li> <li><a href="/wiki/Sodium_chloride" title="Sodium chloride">Salt</a></li> <li><a href="/wiki/Sugar" title="Sugar">Sugar</a> <ul><li><a href="/wiki/High-fructose_corn_syrup" title="High-fructose corn syrup">High-fructose corn syrup</a></li></ul></li> <li><a href="/wiki/Vegetable_oil" title="Vegetable oil">Vegetable oil</a> <ul><li><a href="/wiki/Seed_oil_misinformation" title="Seed oil misinformation">controversy</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Intestinal_parasite_infection" title="Intestinal parasite infection">Intestinal parasites</a>, <a href="/wiki/Parasitic_disease" title="Parasitic disease">parasitic disease</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/Amoebiasis" title="Amoebiasis">Amoebiasis</a></li> <li><a href="/wiki/Anisakiasis" class="mw-redirect" title="Anisakiasis">Anisakiasis</a></li> <li><a href="/wiki/Cryptosporidiosis" title="Cryptosporidiosis">Cryptosporidiosis</a></li> <li><a href="/wiki/Cyclosporiasis" title="Cyclosporiasis">Cyclosporiasis</a></li> <li><a href="/wiki/Diphyllobothriasis" title="Diphyllobothriasis">Diphyllobothriasis</a></li> <li><a href="/wiki/Pinworm_infection" title="Pinworm infection">Enterobiasis</a></li> <li><a href="/wiki/Fasciolopsiasis" title="Fasciolopsiasis">Fasciolopsiasis</a></li> <li><a href="/wiki/Fasciolosis" title="Fasciolosis">Fasciolosis</a></li> <li><a href="/wiki/Giardiasis" title="Giardiasis">Giardiasis</a></li> <li><a href="/wiki/Gnathostomiasis" title="Gnathostomiasis">Gnathostomiasis</a></li> <li><a href="/wiki/Paragonimiasis" title="Paragonimiasis">Paragonimiasis</a></li> <li><a href="/wiki/Toxocariasis" title="Toxocariasis">Toxocariasis</a></li> <li><a href="/wiki/Toxoplasmosis" title="Toxoplasmosis">Toxoplasmosis</a></li> <li><a href="/wiki/Trichinosis" title="Trichinosis">Trichinosis</a></li> <li><a href="/wiki/Trichuriasis" title="Trichuriasis">Trichuriasis</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Microorganism" title="Microorganism">Microorganisms</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/Botulism" title="Botulism">Botulism</a></li> <li><i><a href="/wiki/Campylobacter_jejuni" title="Campylobacter jejuni">Campylobacter jejuni</a></i></li> <li><i><a href="/wiki/Clostridium_perfringens" title="Clostridium perfringens">Clostridium perfringens</a></i></li> <li><i><a href="/wiki/Cronobacter" title="Cronobacter">Cronobacter</a></i></li> <li><i><a href="/wiki/Enterovirus" title="Enterovirus">Enterovirus</a></i></li> <li><a href="/wiki/Escherichia_coli_O104:H4" title="Escherichia coli O104:H4"><i>Escherichia coli</i> O104:H4</a></li> <li><a href="/wiki/Escherichia_coli_O157:H7" title="Escherichia coli O157:H7"><i>Escherichia coli</i> O157:H7</a></li> <li><a href="/wiki/Hepatitis_A" title="Hepatitis A">Hepatitis A</a></li> <li><a href="/wiki/Hepatitis_E" title="Hepatitis E">Hepatitis E</a></li> <li><i><a href="/wiki/Listeria" title="Listeria">Listeria</a></i></li> <li><a href="/wiki/Norovirus" title="Norovirus">Norovirus</a></li> <li><a href="/wiki/Rotavirus" title="Rotavirus">Rotavirus</a></li> <li><i><a href="/wiki/Salmonella" title="Salmonella">Salmonella</a></i></li> <li><a href="/wiki/Shigatoxigenic_and_verotoxigenic_Escherichia_coli" title="Shigatoxigenic and verotoxigenic Escherichia coli">Shigatoxigenic and verotoxigenic <i>E. coli</i></a></li> <li><i><a href="/wiki/Vibrio_cholerae" title="Vibrio cholerae">Vibrio cholerae</a></i></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Pesticide" title="Pesticide">Pesticides</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/Chlorpyrifos" title="Chlorpyrifos">Chlorpyrifos</a></li> <li><a href="/wiki/DDT" title="DDT">DDT</a></li> <li><a href="/wiki/Lindane" title="Lindane">Lindane</a></li> <li><a href="/wiki/Malathion" title="Malathion">Malathion</a></li> <li><a href="/wiki/Methamidophos" title="Methamidophos">Methamidophos</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Preservative" title="Preservative">Preservatives</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/Benzoic_acid" title="Benzoic acid">Benzoic acid</a></li> <li><a href="/wiki/Ethylenediaminetetraacetic_acid" title="Ethylenediaminetetraacetic acid">Ethylenediaminetetraacetic acid (EDTA)</a></li> <li><a href="/wiki/Sodium_benzoate" title="Sodium benzoate">Sodium benzoate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Sugar_substitute" title="Sugar substitute">Sugar substitutes</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/Acesulfame_potassium" title="Acesulfame potassium">Acesulfame potassium</a></li> <li><a href="/wiki/Aspartame" title="Aspartame">Aspartame</a> <ul><li><a href="/wiki/Aspartame_controversy" title="Aspartame controversy">controversy</a></li></ul></li> <li><a href="/wiki/Saccharin" title="Saccharin">Saccharin</a></li> <li><a href="/wiki/Sodium_cyclamate" class="mw-redirect" title="Sodium cyclamate">Sodium cyclamate</a></li> <li><a href="/wiki/Sorbitol" title="Sorbitol">Sorbitol</a></li> <li><a href="/wiki/Sucralose" title="Sucralose">Sucralose</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Toxin" title="Toxin">Toxins</a>, <a href="/wiki/Poison" title="Poison">poisons</a>, <a href="/wiki/Pollution" title="Pollution">environment pollution</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/Aflatoxin" title="Aflatoxin">Aflatoxin</a></li> <li><a href="/wiki/Arsenic_contamination_of_groundwater" title="Arsenic contamination of groundwater">Arsenic contamination of groundwater</a></li> <li><a href="/wiki/Benzene_in_soft_drinks" title="Benzene in soft drinks">Benzene in soft drinks</a></li> <li><a href="/wiki/Bisphenol_A" title="Bisphenol A">Bisphenol A</a></li> <li><a href="/wiki/Dieldrin" title="Dieldrin">Dieldrin</a></li> <li><a href="/wiki/Diethylstilbestrol" title="Diethylstilbestrol">Diethylstilbestrol</a></li> <li><a href="/wiki/Dioxin" title="Dioxin">Dioxin</a></li> <li><a href="/wiki/Mycotoxin" title="Mycotoxin">Mycotoxins</a></li> <li><a href="/wiki/Nonylphenol" title="Nonylphenol">Nonylphenol</a></li> <li><a href="/wiki/Shellfish_poisoning" title="Shellfish poisoning">Shellfish poisoning</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Food_fraud" class="mw-redirect" title="Food fraud">Food fraud</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/Bread_fraud" class="mw-redirect" title="Bread fraud">Bread</a></li> <li><a href="/wiki/Breast_milk_fraud" class="mw-redirect" title="Breast milk fraud">Breast milk</a></li> <li><a href="/wiki/Egg_fraud" class="mw-redirect" title="Egg fraud">Egg</a></li> <li><a href="/wiki/Olive_oil_fraud" class="mw-redirect" title="Olive oil fraud">Olive oil</a></li> <li><a href="/wiki/Prawn_fraud" class="mw-redirect" title="Prawn fraud">Prawn</a></li> <li><a href="/wiki/Seafood_fraud" class="mw-redirect" title="Seafood fraud">Seafood</a></li> <li><a href="/wiki/Shrimp_fraud" class="mw-redirect" title="Shrimp fraud">Shrimp</a></li> <li><a href="/wiki/Tea_fraud" class="mw-redirect" title="Tea fraud">Tea</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Food_processing" title="Food processing">Food processing</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/4-Hydroxynonenal" title="4-Hydroxynonenal">4-Hydroxynonenal</a></li> <li><a href="/wiki/Acid-hydrolyzed_vegetable_protein" class="mw-redirect" title="Acid-hydrolyzed vegetable protein">Acid-hydrolyzed vegetable protein</a></li> <li><a href="/wiki/Acrylamide" title="Acrylamide">Acrylamide</a></li> <li><a href="/wiki/List_of_food_additives" title="List of food additives">Food additives</a></li> <li><a href="/wiki/Food_irradiation" title="Food irradiation">Food irradiation</a></li> <li><a href="/wiki/Heterocyclic_amine" title="Heterocyclic amine">Heterocyclic amines</a></li> <li><a href="/wiki/Modified_starch" title="Modified starch">Modified starch</a></li> <li><a href="/wiki/Nitrosamine" title="Nitrosamine">Nitrosamines</a></li> <li><a class="mw-selflink selflink">Polycyclic aromatic hydrocarbon</a></li> <li><a href="/wiki/Shortening" title="Shortening">Shortening</a></li> <li><a href="/wiki/Trans_fat" title="Trans fat">Trans fat</a></li> <li><a href="/wiki/Variant_Creutzfeldt%E2%80%93Jakob_disease" title="Variant Creutzfeldt–Jakob disease">Variant Creutzfeldt–Jakob disease</a></li> <li><a href="/wiki/Water_fluoridation_controversy" title="Water fluoridation controversy">Water fluoridation controversy</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_food_contamination_incidents" title="List of food contamination incidents">Food contamination incidents</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/Devon_colic" title="Devon colic">Devon colic</a></li> <li><a href="/wiki/Swill_milk_scandal" title="Swill milk scandal">Swill milk scandal</a></li> <li><a href="/wiki/Esing_Bakery_incident" title="Esing Bakery incident">Esing Bakery incident</a></li> <li><a href="/wiki/1858_Bradford_sweets_poisoning" title="1858 Bradford sweets poisoning">1858 Bradford sweets poisoning</a></li> <li><a href="/wiki/1900_English_beer_poisoning" title="1900 English beer poisoning">1900 English beer poisoning</a></li> <li><a href="/wiki/Morinaga_Milk_arsenic_poisoning_incident" title="Morinaga Milk arsenic poisoning incident">Morinaga Milk arsenic poisoning incident</a></li> <li><a href="/wiki/Minamata_disease" title="Minamata disease">Minamata disease</a></li> <li><a href="/w/index.php?title=Moroccan_oil_poisoning_disaster_1959&action=edit&redlink=1" class="new" title="Moroccan oil poisoning disaster 1959 (page does not exist)">Moroccan oil poisoning disaster 1959</a><span class="noprint" style="font-size:85%; font-style: normal;"> [<a href="https://ar.wikipedia.org/wiki/%D9%83%D8%A7%D8%B1%D8%AB%D8%A9_%D8%A7%D9%84%D8%B2%D9%8A%D9%88%D8%AA_%D8%A7%D9%84%D9%85%D8%B3%D9%85%D9%88%D9%85%D8%A9_%D9%81%D9%8A_%D8%A7%D9%84%D9%85%D8%BA%D8%B1%D8%A8_1959" class="extiw" title="ar:كارثة الزيوت المسمومة في المغرب 1959">ar</a>]</span></li> <li><a href="/wiki/1971_Iraq_poison_grain_disaster" title="1971 Iraq poison grain disaster">1971 Iraq poison grain disaster</a></li> <li><a href="/wiki/Toxic_oil_syndrome" title="Toxic oil syndrome">Toxic oil syndrome</a></li> <li><a href="/wiki/1985_Austrian_diethylene_glycol_wine_scandal" title="1985 Austrian diethylene glycol wine scandal">1985 Austrian diethylene glycol wine scandal</a></li> <li><a href="/wiki/United_Kingdom_BSE_outbreak" title="United Kingdom BSE outbreak">United Kingdom BSE outbreak</a></li> <li><a href="/wiki/Australian_meat_substitution_scandal" title="Australian meat substitution scandal">Australian meat substitution scandal</a></li> <li><a href="/wiki/1993_Jack_in_the_Box_E._coli_outbreak" class="mw-redirect" title="1993 Jack in the Box E. coli outbreak">Jack in the Box <i>E. coli</i> outbreak</a></li> <li><a href="/wiki/1996_Odwalla_E._coli_outbreak" title="1996 Odwalla E. coli outbreak">1996 Odwalla <i>E. coli</i> outbreak</a></li> <li><a href="/wiki/2006_North_American_E._coli_O157:H7_outbreaks" title="2006 North American E. coli O157:H7 outbreaks">2006 North American <i>E. coli</i> outbreaks</a></li> <li><a href="/wiki/ICA_meat_repackaging_controversy" title="ICA meat repackaging controversy">ICA meat repackaging controversy</a></li> <li><a href="/wiki/2008_Canada_listeriosis_outbreak" title="2008 Canada listeriosis outbreak">2008 Canada listeriosis outbreak</a></li> <li><a href="/wiki/2008_Chinese_milk_scandal" title="2008 Chinese milk scandal">2008 Chinese milk scandal</a></li> <li><a href="/wiki/2008_Irish_pork_crisis" title="2008 Irish pork crisis">2008 Irish pork crisis</a></li> <li><a href="/wiki/2008_United_States_salmonellosis_outbreak" title="2008 United States salmonellosis outbreak">2008 United States salmonellosis outbreak</a></li> <li><a href="/wiki/2011_Germany_E._coli_O104:H4_outbreak" title="2011 Germany E. coli O104:H4 outbreak">2011 Germany <i>E. coli</i> outbreak</a></li> <li><a href="/wiki/2011_United_States_listeriosis_outbreak" title="2011 United States listeriosis outbreak">2011 United States listeriosis outbreak</a></li> <li><a href="/wiki/Bihar_school_meal_poisoning_incident" title="Bihar school meal poisoning incident">Bihar school meal poisoning</a></li> <li><a href="/wiki/2013_horse_meat_scandal" title="2013 horse meat scandal">2013 horse meat scandal</a></li> <li><a href="/wiki/Mozambique_funeral_beer_poisoning" title="Mozambique funeral beer poisoning">2015 Mozambique funeral beer poisoning</a></li> <li><a href="/wiki/Operation_Weak_Meat" title="Operation Weak Meat">2017 Brazil Operation Weak Meat</a></li> <li><a href="/wiki/2017%E2%80%932018_South_African_listeriosis_outbreak" title="2017–2018 South African listeriosis outbreak">2017–2018 South African listeriosis outbreak</a></li> <li><a href="/wiki/2018_Australian_strawberry_contamination" title="2018 Australian strawberry contamination">2018 Australian strawberry contamination</a></li> <li><a href="/wiki/2024_United_Kingdom_Shigatoxigenic_E._coli_outbreak" title="2024 United Kingdom Shigatoxigenic E. coli outbreak">2024 United Kingdom Shigatoxigenic E. coli outbreak</a></li> <li><a href="/wiki/Kobayashi_red_yeast_rice_scandal" title="Kobayashi red yeast rice scandal">Kobayashi red yeast rice scandal</a></li> <li><a href="/wiki/Food_safety_incidents_in_China" title="Food safety incidents in China">Food safety incidents in China</a></li> <li><a href="/wiki/Food_safety_incidents_in_Taiwan" title="Food safety incidents in Taiwan">Food safety incidents in Taiwan</a></li> <li><a href="/wiki/Foodborne_illness" title="Foodborne illness">Foodborne illness</a> <ul><li><a href="/wiki/List_of_foodborne_illness_outbreaks" title="List of foodborne illness outbreaks">outbreaks</a></li> <li><a href="/wiki/List_of_foodborne_illness_outbreaks_by_death_toll" title="List of foodborne illness outbreaks by death toll">death toll</a></li> <li><a href="/wiki/List_of_foodborne_illness_outbreaks_in_the_United_States" title="List of foodborne illness outbreaks in the United States">United States</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Regulation" title="Regulation">Regulation</a>, <a href="/wiki/Standards_organization" title="Standards organization">standards</a>, <a href="/wiki/List_of_food_safety_organisations" title="List of food safety organisations">watchdogs</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/Acceptable_daily_intake" title="Acceptable daily intake">Acceptable daily intake</a></li> <li><a href="/wiki/E_number" title="E number">E number</a></li> <li><a href="/wiki/List_of_food_labeling_regulations" title="List of food labeling regulations">Food labeling regulations</a></li> <li><a href="/wiki/Food_libel_laws" title="Food libel laws">Food libel laws</a></li> <li><a href="/wiki/Food_safety_in_Australia" title="Food safety in Australia">Food safety in Australia</a></li> <li><a href="/wiki/International_Food_Safety_Network" title="International Food Safety Network">International Food Safety Network</a></li> <li><a href="/wiki/ISO_22000" title="ISO 22000">ISO 22000</a></li> <li><a href="/wiki/Nutrition_facts_label" title="Nutrition facts label">Nutrition facts label</a></li> <li><a href="/wiki/Organic_certification" title="Organic certification">Organic certification</a></li> <li><a href="/wiki/Quality_Assurance_International" title="Quality Assurance International">Quality Assurance International</a></li> <li><a href="/wiki/United_Kingdom_food_information_regulations" title="United Kingdom food information regulations">United Kingdom food information regulations</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_food_safety_organisations" title="List of food safety organisations">Institutions</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/Centre_for_Food_Safety" title="Centre for Food Safety">Centre for Food Safety</a> (Hong Kong)</li> <li><a href="/wiki/European_Food_Safety_Authority" title="European Food Safety Authority">European Food Safety Authority</a></li> <li><a href="/wiki/Food_and_Drug_Administration" title="Food and Drug Administration">Food and Drug Administration</a></li> <li><a href="/wiki/Food_Information_and_Control_Agency" title="Food Information and Control Agency">Food Information and Control Agency</a> (Spain)</li> <li><a href="/wiki/Food_Standards_Agency" title="Food Standards Agency">Food Standards Agency</a> (United Kingdom)</li> <li><a href="/wiki/Institute_for_Food_Safety_and_Health" title="Institute for Food Safety and Health">Institute for Food Safety and Health</a></li> <li><a href="/wiki/International_Food_Safety_Network" title="International Food Safety Network">International Food Safety Network</a></li> <li><a href="/wiki/Ministry_of_Food_and_Drug_Safety" title="Ministry of Food and Drug Safety">Ministry of Food and Drug Safety</a> (South Korea)</li> <li><a href="/wiki/Spanish_Agency_for_Food_Safety_and_Nutrition" title="Spanish Agency for Food Safety and Nutrition">Spanish Agency for Food Safety and Nutrition</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Related topics</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Curing_(food_preservation)" title="Curing (food preservation)">Curing (food preservation)</a></li> <li><a href="/wiki/Food_and_drink_prohibitions" title="Food and drink prohibitions">Food and drink prohibitions</a></li> <li><a href="/wiki/Food_marketing" title="Food marketing">Food marketing</a></li> <li><a href="/wiki/Food_politics" title="Food politics">Food politics</a></li> <li><a href="/wiki/Food_preservation" title="Food preservation">Food preservation</a></li> <li><a href="/wiki/Food_quality" title="Food quality">Food quality</a></li> <li><a href="/wiki/Genetically_modified_food" title="Genetically modified food">Genetically modified food</a></li> <li><a href="/wiki/Conspiracy_theories" class="mw-redirect" title="Conspiracy theories">Conspiracy theories</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2" style="font-weight:bold;"><div> <ul><li><span class="nowrap"><span class="noviewer" typeof="mw:File"><a href="/wiki/File:Foodlogo2.svg" class="mw-file-description"><img alt="icon" src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/Foodlogo2.svg/16px-Foodlogo2.svg.png" decoding="async" width="16" height="12" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/Foodlogo2.svg/24px-Foodlogo2.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d6/Foodlogo2.svg/32px-Foodlogo2.svg.png 2x" data-file-width="146" data-file-height="106" /></a></span> </span><a href="/wiki/Portal:Food" title="Portal:Food">Food portal</a> <span class="nowrap"><span class="noviewer" typeof="mw:File"><span><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e2/Goblet_Glass_%28Banquet%29.svg/9px-Goblet_Glass_%28Banquet%29.svg.png" decoding="async" width="9" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e2/Goblet_Glass_%28Banquet%29.svg/14px-Goblet_Glass_%28Banquet%29.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e2/Goblet_Glass_%28Banquet%29.svg/19px-Goblet_Glass_%28Banquet%29.svg.png 2x" data-file-width="239" data-file-height="408" /></span></span> </span><a href="/wiki/Portal:Drink" title="Portal:Drink">Drink portal</a></li> <li><span class="noviewer" typeof="mw:File"><span title="Category"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/16px-Symbol_category_class.svg.png" decoding="async" width="16" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/23px-Symbol_category_class.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/31px-Symbol_category_class.svg.png 2x" data-file-width="180" data-file-height="185" /></span></span> <a href="/wiki/Category:Food_safety" title="Category:Food safety">Category</a></li> <li><span class="noviewer" typeof="mw:File"><span title="Commons page"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/12px-Commons-logo.svg.png" decoding="async" width="12" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/18px-Commons-logo.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/24px-Commons-logo.svg.png 2x" data-file-width="1024" data-file-height="1376" /></span></span> <a href="https://commons.wikimedia.org/wiki/Category:Food_safety" class="extiw" title="commons:Category:Food safety">Commons</a></li> <li><span class="noviewer" typeof="mw:File"><a href="/wiki/File:Wikibooks-logo.svg" class="mw-file-description" title="Wikibooks page"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/f/fa/Wikibooks-logo.svg/16px-Wikibooks-logo.svg.png" decoding="async" width="16" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/fa/Wikibooks-logo.svg/24px-Wikibooks-logo.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/fa/Wikibooks-logo.svg/32px-Wikibooks-logo.svg.png 2x" data-file-width="300" data-file-height="300" /></a></span> <a href="https://en.wikibooks.org/wiki/Cookbook" class="extiw" title="wikibooks:Cookbook">Cookbook</a></li> <li><span class="noviewer" typeof="mw:File"><span title="WikiProject"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/3/37/People_icon.svg/16px-People_icon.svg.png" decoding="async" width="16" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/37/People_icon.svg/24px-People_icon.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/37/People_icon.svg/32px-People_icon.svg.png 2x" data-file-width="100" data-file-height="100" /></span></span> <a href="/wiki/Wikipedia:WikiProject_Food_and_drink" title="Wikipedia:WikiProject Food and drink">WikiProject</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="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 href="/wiki/Acetone" title="Acetone">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 class="mw-selflink selflink">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, //upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/31px-Symbol_category_class.svg.png 2x" data-file-width="180" data-file-height="185" /></span></span> <a href="/wiki/Category:Astrochemistry" title="Category:Astrochemistry">Category:Astrochemistry</a></b></li> <li><span class="nowrap"><span class="noviewer" typeof="mw:File"><span><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/5/5c/Earth-moon.jpg/16px-Earth-moon.jpg" decoding="async" width="16" height="13" 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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:Aryl_hydrocarbon_receptor_modulators" title="Template:Aryl hydrocarbon receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Aryl_hydrocarbon_receptor_modulators" title="Template talk:Aryl hydrocarbon receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Aryl_hydrocarbon_receptor_modulators" title="Special:EditPage/Template:Aryl hydrocarbon receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Aryl_hydrocarbon_receptor_modulators" style="font-size:114%;margin:0 4em"><a href="/wiki/Aryl_hydrocarbon_receptor" title="Aryl hydrocarbon receptor">Aryl hydrocarbon receptor</a> <a href="/wiki/Receptor_modulator" title="Receptor modulator">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Aryl_hydrocarbon_receptor" title="Aryl hydrocarbon receptor"><abbr title="Aryl hydrocarbon receptor">AhR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Aryl hydrocarbon receptor</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Agonists:</i> <a href="/wiki/Arachidonic_acid" title="Arachidonic acid">Arachidonic acid</a> <a href="/wiki/Metabolite" title="Metabolite">metabolites</a> (e.g., <a href="/wiki/Lipoxin_A4" class="mw-redirect" title="Lipoxin A4">lipoxin A4</a>, <a href="/wiki/Prostaglandin_G2" title="Prostaglandin G2">prostaglandin G2</a>)</li> <li><a href="/wiki/Carotenoid" title="Carotenoid">Dietary carotenoids</a></li> <li><a href="/wiki/Flutamide" title="Flutamide">Flutamide</a></li> <li><a href="/wiki/Halogen" title="Halogen">Halogenated</a> <a href="/wiki/Aromatic_hydrocarbon" class="mw-redirect" title="Aromatic hydrocarbon">aromatic hydrocarbons</a> (e.g., <a href="/wiki/Polychlorinated_dibenzodioxin" class="mw-redirect" title="Polychlorinated dibenzodioxin">polychlorinated dibenzodioxins</a> (e.g., <a href="/wiki/2,3,7,8-Tetrachlorodibenzodioxin" title="2,3,7,8-Tetrachlorodibenzodioxin">TCDD</a>), <a href="/wiki/Dibenzofuran" title="Dibenzofuran">dibenzofurans</a>, <a href="/wiki/Biphenyl" title="Biphenyl">biphenyls</a>)</li> <li><a href="/w/index.php?title=2-(1H-Indol-3-ylcarbonyl)-4-thiazolecarboxylic_acid_methyl_ester&action=edit&redlink=1" class="new" title="2-(1H-Indol-3-ylcarbonyl)-4-thiazolecarboxylic acid methyl ester (page does not exist)">ΙΤΕ</a></li> <li><a href="/wiki/Low-density_lipoprotein" title="Low-density lipoprotein">Modified low-density lipoproteins</a></li> <li><a class="mw-selflink selflink">Polycyclic aromatic hydrocarbons</a> (e.g., <a href="/wiki/3-methylcholanthrene" class="mw-redirect" title="3-methylcholanthrene">3-methylcholanthrene</a>, <a href="/wiki/Benzo(a)pyrene" title="Benzo(a)pyrene">benzo[a]pyrene</a>, <a href="/wiki/Benzanthracene" class="mw-redirect" title="Benzanthracene">benzanthracenes</a>, <a href="/wiki/Benzoflavone" class="mw-redirect" title="Benzoflavone">benzoflavones</a> (e.g., <a href="/wiki/%CE%92-naphthoflavone" class="mw-redirect" title="Β-naphthoflavone">β-naphthoflavone</a>))</li> <li><a href="/wiki/Tapinarof" title="Tapinarof">Tapinarof (benvitimod)</a></li> <li><a href="/wiki/Tetrapyrole" class="mw-redirect" title="Tetrapyrole">Tetrapyroles</a> (e.g., <a href="/wiki/Bilirubin" title="Bilirubin">bilirubin</a>)</li> <li><a href="/wiki/Tryptophan" title="Tryptophan">Tryptophan</a> <a href="/wiki/Chemical_derivative" class="mw-redirect" title="Chemical derivative">derivatives</a> (e.g., <a href="/wiki/Indigo_dye" title="Indigo dye">indigo dye</a>, <a href="/wiki/Indirubin" title="Indirubin">indirubin</a>)</li></ul> <ul><li><i>Antagonists:</i> <a href="/w/index.php?title=7-Ketocholesterol&action=edit&redlink=1" class="new" title="7-Ketocholesterol (page does not exist)">7-Ketocholesterol</a></li> <li><a href="/w/index.php?title=CH-223191&action=edit&redlink=1" class="new" title="CH-223191 (page does not exist)">CH-223191</a></li> <li><a href="/wiki/Cyproterone_acetate" title="Cyproterone acetate">Cyproterone acetate</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt>See also</dt> <dd><i><a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></i></dd></dl> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"><style data-mw-deduplicate="TemplateStyles:r1038841319">.mw-parser-output .tooltip-dotted{border-bottom:1px dotted;cursor:help}</style><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1038841319"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1038841319"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1038841319"></div><div role="navigation" class="navbox authority-control" aria-label="Navbox" style="padding:3px"><table class="nowraplinks hlist navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="row" class="navbox-group" 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