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class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Structure_and_bonding"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.1</span> <span>Structure and bonding</span> </div> </a> <ul id="toc-Structure_and_bonding-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Occurrence" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Occurrence"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>Occurrence</span> </div> </a> <button aria-controls="toc-Occurrence-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Occurrence subsection</span> </button> <ul id="toc-Occurrence-sublist" class="vector-toc-list"> <li id="toc-Interstellar_formaldehyde" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Interstellar_formaldehyde"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.1</span> <span>Interstellar formaldehyde</span> </div> </a> <ul id="toc-Interstellar_formaldehyde-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Synthesis_and_industrial_production" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Synthesis_and_industrial_production"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Synthesis and industrial production</span> </div> </a> <button aria-controls="toc-Synthesis_and_industrial_production-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Synthesis and industrial production subsection</span> </button> <ul id="toc-Synthesis_and_industrial_production-sublist" class="vector-toc-list"> <li id="toc-Laboratory_synthesis" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Laboratory_synthesis"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.1</span> <span>Laboratory synthesis</span> </div> </a> <ul id="toc-Laboratory_synthesis-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Industry" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Industry"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.2</span> <span>Industry</span> </div> </a> <ul id="toc-Industry-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Biochemistry" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Biochemistry"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Biochemistry</span> </div> </a> <ul id="toc-Biochemistry-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Organic_chemistry" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Organic_chemistry"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Organic chemistry</span> </div> </a> <button aria-controls="toc-Organic_chemistry-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 Organic chemistry subsection</span> </button> <ul id="toc-Organic_chemistry-sublist" class="vector-toc-list"> <li id="toc-Polymerization_and_hydration" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Polymerization_and_hydration"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1</span> <span>Polymerization and hydration</span> </div> </a> <ul id="toc-Polymerization_and_hydration-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Cross-linking_reactions" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Cross-linking_reactions"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.2</span> <span>Cross-linking reactions</span> </div> </a> <ul id="toc-Cross-linking_reactions-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Oxidation_and_reduction" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Oxidation_and_reduction"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.3</span> <span>Oxidation and reduction</span> </div> </a> <ul id="toc-Oxidation_and_reduction-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Hydroxymethylation_and_chloromethylation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Hydroxymethylation_and_chloromethylation"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.4</span> <span>Hydroxymethylation and chloromethylation</span> </div> </a> <ul id="toc-Hydroxymethylation_and_chloromethylation-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Other_reactions" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Other_reactions"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.5</span> <span>Other reactions</span> </div> </a> <ul id="toc-Other_reactions-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Uses" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Uses"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Uses</span> </div> </a> <button aria-controls="toc-Uses-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Uses subsection</span> </button> <ul id="toc-Uses-sublist" class="vector-toc-list"> <li id="toc-Industrial_applications" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Industrial_applications"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.1</span> <span>Industrial applications</span> </div> </a> <ul id="toc-Industrial_applications-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Niche_uses" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Niche_uses"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.2</span> <span>Niche uses</span> </div> </a> <ul id="toc-Niche_uses-sublist" class="vector-toc-list"> <li id="toc-Disinfectant_and_biocide" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Disinfectant_and_biocide"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.2.1</span> <span>Disinfectant and biocide</span> </div> </a> <ul id="toc-Disinfectant_and_biocide-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Tissue_fixative_and_embalming_agent" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Tissue_fixative_and_embalming_agent"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.2.2</span> <span>Tissue fixative and embalming agent</span> </div> </a> <ul id="toc-Tissue_fixative_and_embalming_agent-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Drug_testing" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Drug_testing"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.2.3</span> <span>Drug testing</span> </div> </a> <ul id="toc-Drug_testing-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Photography" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Photography"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.3</span> <span>Photography</span> </div> </a> <ul id="toc-Photography-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Safety" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Safety"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Safety</span> </div> </a> <button aria-controls="toc-Safety-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Safety subsection</span> </button> <ul id="toc-Safety-sublist" class="vector-toc-list"> <li id="toc-Chronic_inhalation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Chronic_inhalation"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.1</span> <span>Chronic inhalation</span> </div> </a> <ul id="toc-Chronic_inhalation-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Acute_irritation_and_allergic_reaction" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Acute_irritation_and_allergic_reaction"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.2</span> <span>Acute irritation and allergic reaction</span> </div> </a> <ul id="toc-Acute_irritation_and_allergic_reaction-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Other_routes" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Other_routes"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.3</span> <span>Other routes</span> </div> </a> <ul id="toc-Other_routes-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Regulation" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Regulation"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>Regulation</span> </div> </a> <ul id="toc-Regulation-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Contaminant_in_food" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Contaminant_in_food"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>Contaminant in food</span> </div> </a> <ul id="toc-Contaminant_in_food-sublist" class="vector-toc-list"> </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">10</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">11</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Notes" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Notes"> <div class="vector-toc-text"> <span class="vector-toc-numb">12</span> <span>Notes</span> </div> </a> <ul id="toc-Notes-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">13</span> <span>External links</span> </div> </a> <ul id="toc-External_links-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" title="Table of Contents" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span class="vector-dropdown-label-text">Toggle the table of contents</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Formaldehyde</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 71 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-71" 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">71 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-af mw-list-item"><a href="https://af.wikipedia.org/wiki/Formaldehied" title="Formaldehied – Afrikaans" lang="af" hreflang="af" data-title="Formaldehied" data-language-autonym="Afrikaans" data-language-local-name="Afrikaans" class="interlanguage-link-target"><span>Afrikaans</span></a></li><li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D9%85%D9%8A%D8%AB%D8%A7%D9%86%D8%A7%D9%84" title="ميثانال – Arabic" lang="ar" hreflang="ar" data-title="ميثانال" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-ast mw-list-item"><a href="https://ast.wikipedia.org/wiki/Formaldeh%C3%ADdu" title="Formaldehídu – Asturian" lang="ast" hreflang="ast" data-title="Formaldehídu" data-language-autonym="Asturianu" data-language-local-name="Asturian" class="interlanguage-link-target"><span>Asturianu</span></a></li><li class="interlanguage-link interwiki-az mw-list-item"><a href="https://az.wikipedia.org/wiki/Formaldehid" title="Formaldehid – Azerbaijani" lang="az" hreflang="az" data-title="Formaldehid" data-language-autonym="Azərbaycanca" data-language-local-name="Azerbaijani" class="interlanguage-link-target"><span>Azərbaycanca</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D9%81%D8%B1%D9%85%D8%A7%D9%84%D8%AF%D9%87%DB%8C%D8%AF" title="فرمالدهید – South Azerbaijani" lang="azb" hreflang="azb" data-title="فرمالدهید" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-bn mw-list-item"><a href="https://bn.wikipedia.org/wiki/%E0%A6%AB%E0%A6%B0%E0%A6%AE%E0%A6%BE%E0%A6%B2%E0%A6%BF%E0%A6%A8" title="ফরমালিন – Bangla" lang="bn" hreflang="bn" data-title="ফরমালিন" data-language-autonym="বাংলা" data-language-local-name="Bangla" class="interlanguage-link-target"><span>বাংলা</span></a></li><li class="interlanguage-link interwiki-be mw-list-item"><a href="https://be.wikipedia.org/wiki/%D0%A4%D0%B0%D1%80%D0%BC%D0%B0%D0%BB%D1%8C%D0%B4%D1%8D%D0%B3%D1%96%D0%B4" title="Фармальдэгід – Belarusian" lang="be" hreflang="be" data-title="Фармальдэгід" data-language-autonym="Беларуская" data-language-local-name="Belarusian" class="interlanguage-link-target"><span>Беларуская</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%A4%D0%BE%D1%80%D0%BC%D0%B0%D0%BB%D0%B4%D0%B5%D1%85%D0%B8%D0%B4" title="Формалдехид – Bulgarian" lang="bg" hreflang="bg" data-title="Формалдехид" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target"><span>Български</span></a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Formaldehid" title="Formaldehid – Bosnian" lang="bs" hreflang="bs" data-title="Formaldehid" data-language-autonym="Bosanski" data-language-local-name="Bosnian" class="interlanguage-link-target"><span>Bosanski</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Formaldehid" title="Formaldehid – Catalan" lang="ca" hreflang="ca" data-title="Formaldehid" 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/Formaldehyd" title="Formaldehyd – Czech" lang="cs" hreflang="cs" data-title="Formaldehyd" 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/Formaldehyd" title="Formaldehyd – Danish" lang="da" hreflang="da" data-title="Formaldehyd" data-language-autonym="Dansk" data-language-local-name="Danish" class="interlanguage-link-target"><span>Dansk</span></a></li><li class="interlanguage-link interwiki-de badge-Q17437796 badge-featuredarticle mw-list-item" title="featured article badge"><a href="https://de.wikipedia.org/wiki/Formaldehyd" title="Formaldehyd – German" lang="de" hreflang="de" data-title="Formaldehyd" 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/Metanaal" title="Metanaal – Estonian" lang="et" hreflang="et" data-title="Metanaal" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%A6%CE%BF%CF%81%CE%BC%CE%B1%CE%BB%CE%B4%CE%B5%CE%B0%CE%B4%CE%B7" title="Φορμαλδεΰδη – Greek" lang="el" hreflang="el" data-title="Φορμαλδεΰδη" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target"><span>Ελληνικά</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Formaldeh%C3%ADdo" title="Formaldehído – Spanish" lang="es" hreflang="es" data-title="Formaldehído" 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/Formaldehido" title="Formaldehido – Esperanto" lang="eo" hreflang="eo" data-title="Formaldehido" 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/Formaldehido" title="Formaldehido – Basque" lang="eu" hreflang="eu" data-title="Formaldehido" 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%81%D8%B1%D9%85%D8%A7%D9%84%D8%AF%D9%87%DB%8C%D8%AF" title="فرمالدهید – Persian" lang="fa" hreflang="fa" data-title="فرمالدهید" 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/M%C3%A9thanal" title="Méthanal – French" lang="fr" hreflang="fr" data-title="Méthanal" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ga mw-list-item"><a href="https://ga.wikipedia.org/wiki/Formaild%C3%A9ad" title="Formaildéad – Irish" lang="ga" hreflang="ga" data-title="Formaildéad" data-language-autonym="Gaeilge" data-language-local-name="Irish" class="interlanguage-link-target"><span>Gaeilge</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Formaldehido" title="Formaldehido – Galician" lang="gl" hreflang="gl" data-title="Formaldehido" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%ED%8F%BC%EC%95%8C%EB%8D%B0%ED%95%98%EC%9D%B4%EB%93%9C" title="폼알데하이드 – Korean" lang="ko" hreflang="ko" data-title="폼알데하이드" 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%84%D6%80%D5%BB%D5%B6%D5%A1%D5%AC%D5%A4%D5%A5%D5%B0%D5%AB%D5%A4" title="Մրջնալդեհիդ – Armenian" lang="hy" hreflang="hy" data-title="Մրջնալդեհիդ" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-hi mw-list-item"><a href="https://hi.wikipedia.org/wiki/%E0%A4%AB%E0%A4%BE%E0%A4%B0%E0%A5%8D%E0%A4%AE%E0%A4%B2%E0%A5%8D%E0%A4%A1%E0%A4%BF%E0%A4%B9%E0%A4%BE%E0%A4%87%E0%A4%A1" title="फार्मल्डिहाइड – Hindi" lang="hi" hreflang="hi" data-title="फार्मल्डिहाइड" data-language-autonym="हिन्दी" data-language-local-name="Hindi" class="interlanguage-link-target"><span>हिन्दी</span></a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Formaldehid" title="Formaldehid – Croatian" lang="hr" hreflang="hr" data-title="Formaldehid" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-io mw-list-item"><a href="https://io.wikipedia.org/wiki/Formaldehido" title="Formaldehido – Ido" lang="io" hreflang="io" data-title="Formaldehido" data-language-autonym="Ido" data-language-local-name="Ido" class="interlanguage-link-target"><span>Ido</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Formaldehida" title="Formaldehida – Indonesian" lang="id" hreflang="id" data-title="Formaldehida" 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/Formaldeide" title="Formaldeide – Italian" lang="it" hreflang="it" data-title="Formaldeide" 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%95%D7%A8%D7%9E%D7%9C%D7%99%D7%9F" title="פורמלין – Hebrew" lang="he" hreflang="he" data-title="פורמלין" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-jv mw-list-item"><a href="https://jv.wikipedia.org/wiki/Formaldehida" title="Formaldehida – Javanese" lang="jv" hreflang="jv" data-title="Formaldehida" data-language-autonym="Jawa" data-language-local-name="Javanese" class="interlanguage-link-target"><span>Jawa</span></a></li><li class="interlanguage-link interwiki-ka mw-list-item"><a href="https://ka.wikipedia.org/wiki/%E1%83%A4%E1%83%9D%E1%83%A0%E1%83%9B%E1%83%90%E1%83%9A%E1%83%93%E1%83%94%E1%83%B0%E1%83%98%E1%83%93%E1%83%98" title="ფორმალდეჰიდი – Georgian" lang="ka" hreflang="ka" data-title="ფორმალდეჰიდი" data-language-autonym="ქართული" data-language-local-name="Georgian" class="interlanguage-link-target"><span>ქართული</span></a></li><li class="interlanguage-link interwiki-kk mw-list-item"><a href="https://kk.wikipedia.org/wiki/%D0%A4%D0%BE%D1%80%D0%BC%D0%B0%D0%BB%D1%8C%D0%B4%D0%B5%D0%B3%D0%B8%D0%B4" title="Формальдегид – Kazakh" lang="kk" hreflang="kk" data-title="Формальдегид" data-language-autonym="Қазақша" data-language-local-name="Kazakh" class="interlanguage-link-target"><span>Қазақша</span></a></li><li class="interlanguage-link interwiki-ky mw-list-item"><a href="https://ky.wikipedia.org/wiki/%D0%A4%D0%BE%D1%80%D0%BC%D0%B0%D0%BB%D1%8C%D0%B4%D0%B5%D0%B3%D0%B8%D0%B4" title="Формальдегид – Kyrgyz" lang="ky" hreflang="ky" data-title="Формальдегид" data-language-autonym="Кыргызча" data-language-local-name="Kyrgyz" class="interlanguage-link-target"><span>Кыргызча</span></a></li><li class="interlanguage-link interwiki-la mw-list-item"><a href="https://la.wikipedia.org/wiki/Methanal" title="Methanal – Latin" lang="la" hreflang="la" data-title="Methanal" data-language-autonym="Latina" data-language-local-name="Latin" class="interlanguage-link-target"><span>Latina</span></a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Formaldeh%C4%ABds" title="Formaldehīds – Latvian" lang="lv" hreflang="lv" data-title="Formaldehīds" 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/Formaldehidas" title="Formaldehidas – Lithuanian" lang="lt" hreflang="lt" data-title="Formaldehidas" data-language-autonym="Lietuvių" data-language-local-name="Lithuanian" class="interlanguage-link-target"><span>Lietuvių</span></a></li><li class="interlanguage-link interwiki-lij mw-list-item"><a href="https://lij.wikipedia.org/wiki/Formaldeide" title="Formaldeide – Ligurian" lang="lij" hreflang="lij" data-title="Formaldeide" data-language-autonym="Ligure" data-language-local-name="Ligurian" class="interlanguage-link-target"><span>Ligure</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Formaldehid" title="Formaldehid – Hungarian" lang="hu" hreflang="hu" data-title="Formaldehid" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%A4%D0%BE%D1%80%D0%BC%D0%B0%D0%BB%D0%B4%D0%B5%D1%85%D0%B8%D0%B4" title="Формалдехид – Macedonian" lang="mk" hreflang="mk" data-title="Формалдехид" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-ml mw-list-item"><a href="https://ml.wikipedia.org/wiki/%E0%B4%AB%E0%B5%8B%E0%B5%BC%E0%B4%AE%E0%B4%BE%E0%B5%BE%E0%B4%A1%E0%B4%BF%E0%B4%B9%E0%B5%88%E0%B4%A1%E0%B5%8D" title="ഫോർമാൾഡിഹൈഡ് – Malayalam" lang="ml" hreflang="ml" data-title="ഫോർമാൾഡിഹൈഡ്" data-language-autonym="മലയാളം" data-language-local-name="Malayalam" class="interlanguage-link-target"><span>മലയാളം</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Formaldehid" title="Formaldehid – Malay" lang="ms" hreflang="ms" data-title="Formaldehid" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" class="interlanguage-link-target"><span>Bahasa Melayu</span></a></li><li class="interlanguage-link interwiki-my mw-list-item"><a href="https://my.wikipedia.org/wiki/%E1%80%96%E1%80%B1%E1%80%AC%E1%80%BA%E1%80%99%E1%80%9C%E1%80%84%E1%80%BA" title="ဖော်မလင် – Burmese" lang="my" hreflang="my" data-title="ဖော်မလင်" data-language-autonym="မြန်မာဘာသာ" data-language-local-name="Burmese" class="interlanguage-link-target"><span>မြန်မာဘာသာ</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Formaldehyde" title="Formaldehyde – Dutch" lang="nl" hreflang="nl" data-title="Formaldehyde" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%9B%E3%83%AB%E3%83%A0%E3%82%A2%E3%83%AB%E3%83%87%E3%83%92%E3%83%89" title="ホルムアルデヒド – Japanese" lang="ja" hreflang="ja" data-title="ホルムアルデヒド" 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/Formaldehyd" title="Formaldehyd – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Formaldehyd" data-language-autonym="Norsk bokmål" data-language-local-name="Norwegian Bokmål" class="interlanguage-link-target"><span>Norsk bokmål</span></a></li><li class="interlanguage-link interwiki-uz mw-list-item"><a href="https://uz.wikipedia.org/wiki/Formaldegid" title="Formaldegid – Uzbek" lang="uz" hreflang="uz" data-title="Formaldegid" data-language-autonym="Oʻzbekcha / ўзбекча" data-language-local-name="Uzbek" class="interlanguage-link-target"><span>Oʻzbekcha / ўзбекча</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Aldehyd_mr%C3%B3wkowy" title="Aldehyd mrówkowy – Polish" lang="pl" hreflang="pl" data-title="Aldehyd mrówkowy" 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/Metanal" title="Metanal – Portuguese" lang="pt" hreflang="pt" data-title="Metanal" 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/Formaldehid%C4%83" title="Formaldehidă – Romanian" lang="ro" hreflang="ro" data-title="Formaldehidă" 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%A4%D0%BE%D1%80%D0%BC%D0%B0%D0%BB%D1%8C%D0%B4%D0%B5%D0%B3%D0%B8%D0%B4" title="Формальдегид – Russian" lang="ru" hreflang="ru" data-title="Формальдегид" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sco mw-list-item"><a href="https://sco.wikipedia.org/wiki/Formaldehyde" title="Formaldehyde – Scots" lang="sco" hreflang="sco" data-title="Formaldehyde" data-language-autonym="Scots" data-language-local-name="Scots" class="interlanguage-link-target"><span>Scots</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Formaldehyde" title="Formaldehyde – Simple English" lang="en-simple" hreflang="en-simple" data-title="Formaldehyde" data-language-autonym="Simple English" data-language-local-name="Simple English" class="interlanguage-link-target"><span>Simple English</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Formaldehyd" title="Formaldehyd – Slovak" lang="sk" hreflang="sk" data-title="Formaldehyd" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Formaldehid" title="Formaldehid – Slovenian" lang="sl" hreflang="sl" data-title="Formaldehid" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-sr badge-Q17437798 badge-goodarticle mw-list-item" title="good article badge"><a href="https://sr.wikipedia.org/wiki/%D0%A4%D0%BE%D1%80%D0%BC%D0%B0%D0%BB%D0%B4%D0%B5%D1%85%D0%B8%D0%B4" title="Формалдехид – Serbian" lang="sr" hreflang="sr" data-title="Формалдехид" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Formaldehid" title="Formaldehid – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Formaldehid" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-su mw-list-item"><a href="https://su.wikipedia.org/wiki/Formaldehida" title="Formaldehida – Sundanese" lang="su" hreflang="su" data-title="Formaldehida" data-language-autonym="Sunda" data-language-local-name="Sundanese" class="interlanguage-link-target"><span>Sunda</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Formaldehydi" title="Formaldehydi – Finnish" lang="fi" hreflang="fi" data-title="Formaldehydi" 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/Formaldehyd" title="Formaldehyd – Swedish" lang="sv" hreflang="sv" data-title="Formaldehyd" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%AA%E0%AE%BE%E0%AE%B0%E0%AF%8D%E0%AE%AE%E0%AE%BE%E0%AE%B2%E0%AF%8D%E0%AE%9F%E0%AE%BF%E0%AE%95%E0%AF%88%E0%AE%9F%E0%AF%81" title="பார்மால்டிகைடு – Tamil" lang="ta" hreflang="ta" data-title="பார்மால்டிகைடு" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-te mw-list-item"><a href="https://te.wikipedia.org/wiki/%E0%B0%AB%E0%B0%BE%E0%B0%B0%E0%B1%8D%E0%B0%AE%E0%B0%BE%E0%B0%B2%E0%B1%8D%E0%B0%A1%E0%B0%BF%E0%B0%B9%E0%B1%88%E0%B0%A1%E0%B1%8D" title="ఫార్మాల్డిహైడ్ – Telugu" lang="te" hreflang="te" data-title="ఫార్మాల్డిహైడ్" data-language-autonym="తెలుగు" data-language-local-name="Telugu" class="interlanguage-link-target"><span>తెలుగు</span></a></li><li class="interlanguage-link interwiki-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B8%9F%E0%B8%AD%E0%B8%A3%E0%B9%8C%E0%B8%A1%E0%B8%B2%E0%B8%A5%E0%B8%94%E0%B8%B5%E0%B9%84%E0%B8%AE%E0%B8%94%E0%B9%8C" title="ฟอร์มาลดีไฮด์ – Thai" lang="th" hreflang="th" data-title="ฟอร์มาลดีไฮด์" 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/Formaldehit" title="Formaldehit – Turkish" lang="tr" hreflang="tr" data-title="Formaldehit" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-uk badge-Q17437798 badge-goodarticle mw-list-item" title="good article badge"><a href="https://uk.wikipedia.org/wiki/%D0%A4%D0%BE%D1%80%D0%BC%D0%B0%D0%BB%D1%8C%D0%B4%D0%B5%D0%B3%D1%96%D0%B4" title="Формальдегід – Ukrainian" lang="uk" hreflang="uk" data-title="Формальдегід" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-ur mw-list-item"><a href="https://ur.wikipedia.org/wiki/%D9%81%D8%A7%D8%B1%D9%85%D9%84%DA%88%DB%8C%DB%81%D8%A7%D8%A6%DA%88" title="فارملڈیہائڈ – Urdu" lang="ur" hreflang="ur" data-title="فارملڈیہائڈ" data-language-autonym="اردو" data-language-local-name="Urdu" class="interlanguage-link-target"><span>اردو</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Formaldehyde" title="Formaldehyde – Vietnamese" lang="vi" hreflang="vi" data-title="Formaldehyde" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target"><span>Tiếng Việt</span></a></li><li class="interlanguage-link interwiki-war mw-list-item"><a href="https://war.wikipedia.org/wiki/Formaldehyde" title="Formaldehyde – Waray" lang="war" hreflang="war" data-title="Formaldehyde" data-language-autonym="Winaray" data-language-local-name="Waray" class="interlanguage-link-target"><span>Winaray</span></a></li><li class="interlanguage-link interwiki-wuu mw-list-item"><a href="https://wuu.wikipedia.org/wiki/%E7%94%B2%E9%86%9B" title="甲醛 – Wu" lang="wuu" 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dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Organic compound (H–CHO); simplest aldehyde</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">"Methanal" redirects here. Not to be confused with <a href="/wiki/Methanol" title="Methanol">Methanol</a> or <a href="/wiki/Menthol" title="Menthol">Menthol</a>.</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">For other uses, see <a href="/wiki/Formaldehyde_(disambiguation)" class="mw-disambig" title="Formaldehyde (disambiguation)">Formaldehyde (disambiguation)</a>.</div> <style data-mw-deduplicate="TemplateStyles:r1268415487">.mw-parser-output .ib-chembox{border-collapse:collapse;text-align:left}.mw-parser-output .ib-chembox td,.mw-parser-output .ib-chembox th{border:1px solid #a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}</style> <table class="infobox ib-chembox"> <caption>Formaldehyde </caption> <tbody><tr> <td colspan="2" class="borderless" style="text-align:center"> <table border="0" style="width:100%;display:inline-table;"> <tbody><tr> <td style="border-right:1px solid #aaa; width:50%;"><figure class="mw-halign-center skin-invert-image" typeof="mw:File"><a href="/wiki/File:Structural_formula_of_formaldehyde.svg" class="mw-file-description" title="Structural formula of formaldehyde (with hydrogens)"><img alt="Structural formula of formaldehyde (with hydrogens)" src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0c/Structural_formula_of_formaldehyde.svg/110px-Structural_formula_of_formaldehyde.svg.png" decoding="async" width="110" height="102" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0c/Structural_formula_of_formaldehyde.svg/165px-Structural_formula_of_formaldehyde.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/0c/Structural_formula_of_formaldehyde.svg/220px-Structural_formula_of_formaldehyde.svg.png 2x" data-file-width="114" data-file-height="106" /></a><figcaption>Structural formula of formaldehyde (with hydrogens)</figcaption></figure> </td> <td style="width:50%;"><figure class="mw-halign-center bg-transparent" typeof="mw:File"><a href="/wiki/File:Formaldehyde-3D-vdW.png" class="mw-file-description" title="Spacefill model of formaldehyde"><img alt="Spacefill model of formaldehyde" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a3/Formaldehyde-3D-vdW.png/110px-Formaldehyde-3D-vdW.png" decoding="async" width="110" height="119" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a3/Formaldehyde-3D-vdW.png/165px-Formaldehyde-3D-vdW.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a3/Formaldehyde-3D-vdW.png/220px-Formaldehyde-3D-vdW.png 2x" data-file-width="1016" data-file-height="1100" /></a><figcaption>Spacefill model of formaldehyde</figcaption></figure> </td></tr></tbody></table> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><figure class="mw-halign-center bg-transparent" typeof="mw:File"><a href="/wiki/File:Formaldehyde-3D-balls-A.png" class="mw-file-description" title="Ball and stick model of formaldehyde"><img alt="Ball and stick model of formaldehyde" src="//upload.wikimedia.org/wikipedia/commons/thumb/7/76/Formaldehyde-3D-balls-A.png/121px-Formaldehyde-3D-balls-A.png" decoding="async" width="121" height="129" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/76/Formaldehyde-3D-balls-A.png/182px-Formaldehyde-3D-balls-A.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/76/Formaldehyde-3D-balls-A.png/242px-Formaldehyde-3D-balls-A.png 2x" data-file-width="1030" data-file-height="1100" /></a><figcaption>Ball and stick model of formaldehyde</figcaption></figure> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Preferred_IUPAC_name" title="Preferred IUPAC name">Preferred IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;">Formaldehyde<sup id="cite_ref-iupac2013_1-0" class="reference"><a href="#cite_note-iupac2013-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup></div></div> </td></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Chemical_nomenclature#Systematic_name" title="Chemical nomenclature">Systematic IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;">Methanal<sup id="cite_ref-iupac2013_1-1" class="reference"><a href="#cite_note-iupac2013-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup></div></div> </td></tr> <tr> <td colspan="2" style="text-align:left;">Other names <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li>Methyl aldehyde</li><li><a href="/wiki/Methylene_glycol" class="mw-redirect" title="Methylene glycol">Methylene glycol</a> (diol forms in aqueous solution)</li><li>Methylene oxide</li><li>Formalin (aqueous solution)</li><li>Formol</li><li>Carbonyl hydride</li><li>Methanone</li><li>Oxomethane</li></ul></div></div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=50-00-0">50-00-0</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=C%3DO">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Beilstein_database" title="Beilstein database">Beilstein Reference</a></div> </td> <td>1209228 </td></tr> <tr> <td><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=16842">CHEBI:16842</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembl/explore/compound/ChEMBL1255">ChEMBL1255</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.692.html">692</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/DrugBank" title="DrugBank">DrugBank</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.drugbank.ca"><a rel="nofollow" class="external text" href="https://www.drugbank.ca/drugs/DB03843">DB03843</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a> </td> <td><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.000.002">100.000.002</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q161210#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span> </td></tr> <tr> <td><a href="/wiki/European_Community_number" title="European Community number"><span title="European Community number (chemical identifier)">EC Number</span></a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>200-001-8</li></ul></div> </td></tr> <tr> <td><a href="/wiki/E_number" title="E number"><span title="E number (food additive code)">E number</span></a> </td> <td>E240 <a href="/wiki/E_number#E200–E299" title="E number">(preservatives)</a> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Gmelin_database" title="Gmelin database">Gmelin Reference</a></div> </td> <td>445 </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/IUPHAR/BPS" class="mw-redirect" title="IUPHAR/BPS">IUPHAR/BPS</a></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.guidetopharmacology.org"><a rel="nofollow" class="external text" href="http://www.guidetopharmacology.org/GRAC/LigandDisplayForward?tab=summary&ligandId=4196">4196</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/KEGG" title="KEGG">KEGG</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.kegg.jp"><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/D00017">D00017</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/Medical_Subject_Headings" title="Medical Subject Headings">MeSH</a> </td> <td><span title="www.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://www.nlm.nih.gov/cgi/mesh/2014/MB_cgi?mode=&term=Formaldehyde">Formaldehyde</a></span> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/712">712</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/RTECS" class="mw-redirect" title="RTECS">RTECS number</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>LP8925000</li></ul></div> </td></tr> <tr> <td><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/1HG84L3525">1HG84L3525</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/UN_number" title="UN number">UN number</a> </td> <td>2209 </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID7020637">DTXSID7020637</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q161210#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></span></li></ul></div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/CH2O/c1-2/h1H2<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: WSFSSNUMVMOOMR-UHFFFAOYSA-N<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div></div></li><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1/CH2O/c1-2/h1H2</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: WSFSSNUMVMOOMR-UHFFFAOYAT</div></div></li></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">C=O</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Properties<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> </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td><span title="Carbon">C</span><span title="Hydrogen">H</span><sub>2</sub><span title="Oxygen">O</span> </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td><span class="nowrap"><span data-sort-value="7001300260000000000♠"></span>30.026</span> g·mol<sup>−1</sup>   </td></tr> <tr> <td>Appearance </td> <td>Colorless gas </td></tr> <tr> <td><a href="/wiki/Density" title="Density">Density</a> </td> <td>0.8153 g/cm<sup>3</sup> (−20 °C)<sup id="cite_ref-ipcs_2-0" class="reference"><a href="#cite_note-ipcs-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> (liquid) </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>−92 °C (−134 °F; 181 K) </td></tr> <tr> <td><a href="/wiki/Boiling_point" title="Boiling point">Boiling point</a> </td> <td>−19 °C (−2 °F; 254 K)<sup id="cite_ref-ipcs_2-1" class="reference"><a href="#cite_note-ipcs-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Aqueous_solution" title="Aqueous solution">Solubility in water</a></div> </td> <td>400 g/L </td></tr> <tr> <td><a href="/wiki/Partition_coefficient" title="Partition coefficient">log <i>P</i></a> </td> <td>0.350 </td></tr> <tr> <td><a href="/wiki/Vapor_pressure" title="Vapor pressure">Vapor pressure</a> </td> <td>> 1 atm<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> </td></tr> <tr> <td><a href="/wiki/Acid_dissociation_constant" title="Acid dissociation constant">Acidity</a> (p<i>K</i><sub>a</sub>) </td> <td>13.27 (hydrate)<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><sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Magnetic_susceptibility" title="Magnetic susceptibility">Magnetic susceptibility</a> (χ)</div> </td> <td>−18.6·10<sup>−6</sup> cm<sup>3</sup>/mol </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Dipole#Molecular_dipoles" title="Dipole">Dipole moment</a></div> </td> <td>2.330 D<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> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Structure </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Molecular_symmetry" title="Molecular symmetry">Point group</a></div> </td> <td>C<sub>2v</sub> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Molecular_geometry" title="Molecular geometry">Molecular shape</a></div> </td> <td>Trigonal planar </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Thermochemistry<sup id="cite_ref-CRC97_8-0" class="reference"><a href="#cite_note-CRC97-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Heat_capacity" title="Heat capacity">Heat capacity</a> <span style="font-size:112%;">(<i>C</i>)</span></div> </td> <td>35.387 J·mol<sup>−1</sup>·K<sup>−1</sup> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Standard_molar_entropy" title="Standard molar entropy">Std molar<br />entropy</a> <span style="font-size:112%;">(<i>S</i><sup>⦵</sup><sub>298</sub>)</span></div> </td> <td>218.760 J·mol<sup>−1</sup>·K<sup>−1</sup> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Standard_enthalpy_change_of_formation" class="mw-redirect" title="Standard enthalpy change of formation">Std enthalpy of<br />formation</a> <span style="font-size:112%;">(Δ<sub>f</sub><i>H</i><sup>⦵</sup><sub>298</sub>)</span></div> </td> <td>−108.700 kJ·mol<sup>−1</sup> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Gibbs_free_energy#Standard_energy_change_of_formation" title="Gibbs free energy">Gibbs free energy</a> <span style="font-size:112%;">(Δ<sub>f</sub><i>G</i><sup>⦵</sup>)</span></div> </td> <td>−102.667 kJ·mol<sup>−1</sup> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Standard_enthalpy_change_of_combustion" class="mw-redirect" title="Standard enthalpy change of combustion">Std enthalpy of<br />combustion</a> <span style="font-size:112%;">(Δ<sub>c</sub><i>H</i><sup>⦵</sup><sub>298</sub>)</span></div> </td> <td>571 kJ·mol<sup>−1</sup> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Pharmacology </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Anatomical_Therapeutic_Chemical_Classification_System#ATCvet" title="Anatomical Therapeutic Chemical Classification System">ATCvet code</a></div> </td> <td><a href="/wiki/ATC_code_P53" class="mw-redirect" title="ATC code P53">QP53AX19</a> (<span title="www.whocc.no/atcvet"><a rel="nofollow" class="external text" href="https://www.whocc.no/atcvet/atcvet_index/?code=QP53AX19">WHO</a></span>)  </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Hazards </th></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;color:inherit;"><a href="/wiki/Globally_Harmonized_System_of_Classification_and_Labelling_of_Chemicals" title="Globally Harmonized System of Classification and Labelling of Chemicals"><b>GHS</b> labelling</a>: </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_hazard_pictograms" title="GHS hazard pictograms">Pictograms</a></div> </td> <td><span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-skull.svg" class="mw-file-description" title="GHS06: Toxic"><img alt="GHS06: Toxic" src="//upload.wikimedia.org/wikipedia/commons/thumb/5/58/GHS-pictogram-skull.svg/50px-GHS-pictogram-skull.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/58/GHS-pictogram-skull.svg/75px-GHS-pictogram-skull.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/58/GHS-pictogram-skull.svg/100px-GHS-pictogram-skull.svg.png 2x" data-file-width="724" data-file-height="724" /></a></span><span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-acid.svg" class="mw-file-description" title="GHS05: Corrosive"><img alt="GHS05: Corrosive" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a1/GHS-pictogram-acid.svg/50px-GHS-pictogram-acid.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a1/GHS-pictogram-acid.svg/75px-GHS-pictogram-acid.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a1/GHS-pictogram-acid.svg/100px-GHS-pictogram-acid.svg.png 2x" data-file-width="724" data-file-height="724" /></a></span><span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-silhouette.svg" class="mw-file-description" title="GHS08: Health hazard"><img alt="GHS08: Health hazard" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/GHS-pictogram-silhouette.svg/50px-GHS-pictogram-silhouette.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/GHS-pictogram-silhouette.svg/75px-GHS-pictogram-silhouette.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/21/GHS-pictogram-silhouette.svg/100px-GHS-pictogram-silhouette.svg.png 2x" data-file-width="724" data-file-height="724" /></a></span><sup id="cite_ref-GESTIS_9-0" class="reference"><a href="#cite_note-GESTIS-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Globally_Harmonized_System_of_Classification_and_Labelling_of_Chemicals#Signal_word" title="Globally Harmonized System of Classification and Labelling of Chemicals">Signal word</a></div> </td> <td><b>Danger</b> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_hazard_statements" title="GHS hazard statements">Hazard statements</a></div> </td> <td><abbr class="abbr" title="H301+H311+H331: Toxic if swallowed, in contact with skin or if inhaled">H301+H311+H331</abbr>, <abbr class="abbr" title="H314: Causes severe skin burns and eye damage">H314</abbr>, <abbr class="abbr" title="H317: May cause an allergic skin reaction">H317</abbr>, <abbr class="abbr" title="H335: May cause respiratory irritation">H335</abbr>, <abbr class="abbr" title="H341: Suspected of causing genetic defects">H341</abbr>, <abbr class="abbr" title="H350: May cause cancer">H350</abbr>, <abbr class="abbr" title="H370: Causes damage to organs">H370</abbr><sup id="cite_ref-GESTIS_9-1" class="reference"><a href="#cite_note-GESTIS-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_precautionary_statements" title="GHS precautionary statements">Precautionary statements</a></div> </td> <td><abbr class="abbr" title="P201: Obtain special instructions before use.">P201</abbr>, <abbr class="abbr" title="P280: Wear protective gloves/protective clothing/eye protection/face protection.">P280</abbr>, <abbr class="abbr" title="P303+P361+P353: IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water [or shower].">P303+P361+P353</abbr>, <abbr class="abbr" title="P304+P340+P310: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing. Immediately call a POISON CENTER or doctor/physician.">P304+P340+P310</abbr>, <abbr class="abbr" title="P305+P351+P338: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do. Continue rinsing.">P305+P351+P338</abbr>, <abbr class="abbr" title="P308+P310: IF exposed or concerned: Immediately call a POISON CENTER or doctor/physician.">P308+P310</abbr><sup id="cite_ref-GESTIS_9-2" class="reference"><a href="#cite_note-GESTIS-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/NFPA_704" title="NFPA 704"><b>NFPA 704</b></a> (fire diamond) </td> <td><style data-mw-deduplicate="TemplateStyles:r1170367383">.mw-parser-output .nfpa-704-diamond-ref{float:right;padding:1px;text-align:right}.mw-parser-output .nfpa-704-diamond-container{width:82px;font-family:sans-serif;margin:0 auto}.mw-parser-output .nfpa-704-diamond-container-ref{float:left;margin-left:1em}.mw-parser-output .nfpa-704-diamond-images{float:left;font-size:20px;text-align:center;position:relative;height:80px;width:80px;padding:1px}.mw-parser-output .nfpa-704-diamond-map{position:absolute;height:80px;width:80px}.mw-parser-output .nfpa-704-diamond .noresize{margin:0 auto}.mw-parser-output .nfpa-704-diamond-code{line-height:1em;text-align:center;position:absolute}.mw-parser-output .nfpa-704-diamond-code>a{color:black}.mw-parser-output .nfpa-704-diamond-blue{width:13px;top:31px;left:15px}.mw-parser-output .nfpa-704-diamond-red{width:12px;top:12px;left:35px}.mw-parser-output .nfpa-704-diamond-yellow{width:13px;top:31px;left:54px}.mw-parser-output .nfpa-704-diamond-white-image{position:relative;top:51px;left:0}.mw-parser-output .nfpa-704-diamond-white-text{vertical-align:middle;text-align:center;line-height:80%;position:absolute;top:52px}.mw-parser-output .nfpa-704-diamond-white-text a>span{position:absolute;color:black}.mw-parser-output .nfpa-704-diamond-white-wors{font-size:15px;width:23px;left:29px}.mw-parser-output .nfpa-704-diamond-white-wox{font-size:15px;font-stretch:condensed;width:21px;line-height:80%;top:-4px;left:29px}.mw-parser-output .nfpa-704-diamond-white-abcp{font-size:13.5px;font-stretch:condensed;width:28px;left:26px}.mw-parser-output .nfpa-704-diamond-white-ac{font-size:10px;width:30px;left:25px}.mw-parser-output .nfpa-704-diamond-white-strike{text-decoration:line-through}</style><div class="nfpa-704-diamond notheme"><div class="nfpa-704-diamond-container"><div class="nfpa-704-diamond-images nounderlines"> <div class="nfpa-704-diamond-map"><figure class="noresize" typeof="mw:File"><span><img alt="NFPA 704 four-colored diamond" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/80px-NFPA_704.svg.png" decoding="async" width="80" height="80" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/120px-NFPA_704.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/160px-NFPA_704.svg.png 2x" data-file-width="512" data-file-height="512" usemap="#ImageMap_2c0cf5af8cd61e7a" /></span><map name="ImageMap_2c0cf5af8cd61e7a"><area href="/wiki/NFPA_704#Blue" shape="poly" coords="23,23,47,47,23,70,0,47" alt="Health 4: Very short exposure could cause death or major residual injury. E.g. VX gas" title="Health 4: Very short exposure could cause death or major residual injury. E.g. VX gas" /><area href="/wiki/NFPA_704#Red" shape="poly" coords="47,0,70,23,47,47,23,23" alt="Flammability 4: Will rapidly or completely vaporize at normal atmospheric pressure and temperature, or is readily dispersed in air and will burn readily. Flash point below 23 °C (73 °F). E.g. propane" title="Flammability 4: Will rapidly or completely vaporize at normal atmospheric pressure and temperature, or is readily dispersed in air and will burn readily. Flash point below 23 °C (73 °F). E.g. propane" /><area href="/wiki/NFPA_704#Yellow" shape="poly" coords="70,23,94,47,70,70,47,47" alt="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" title="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" /><area href="/wiki/NFPA_704#White" shape="poly" coords="47,47,70,70,47,94,23,70" alt="Special hazard COR: Corrosive; strong acid or base. E.g. sulfuric acid, potassium hydroxide" title="Special hazard COR: Corrosive; strong acid or base. E.g. sulfuric acid, potassium hydroxide" /></map><figcaption></figcaption></figure></div><div class="nfpa-704-diamond-code nfpa-704-diamond-blue"> <a href="/wiki/NFPA_704#Blue" title="NFPA 704"><span title="Health 4: Very short exposure could cause death or major residual injury. E.g. VX gas" class="notheme mw-no-invert">4</span></a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-red"> <a href="/wiki/NFPA_704#Red" title="NFPA 704"><span title="Flammability 4: Will rapidly or completely vaporize at normal atmospheric pressure and temperature, or is readily dispersed in air and will burn readily. Flash point below 23 °C (73 °F). E.g. propane" class="notheme mw-no-invert">4</span></a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-yellow"> <a href="/wiki/NFPA_704#Yellow" title="NFPA 704"><span title="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" class="notheme mw-no-invert">0</span></a></div><div class="nfpa-704-diamond-white-text mw-no-invert"><a href="/wiki/NFPA_704#White" title="NFPA 704"><span class="nfpa-704-diamond-white-abcp" title="Special hazard COR: Corrosive; strong acid or base. E.g. sulfuric acid, potassium hydroxide">COR</span></a></div></div></div></div> </td></tr> <tr> <td><a href="/wiki/Flash_point" title="Flash point">Flash point</a> </td> <td>64 °C (147 °F; 337 K) </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Autoignition_temperature" title="Autoignition temperature">Autoignition<br />temperature</a></div> </td> <td>430 °C (806 °F; 703 K) </td></tr> <tr> <td><a href="/wiki/Explosive_limit" class="mw-redirect" title="Explosive limit">Explosive limits</a> </td> <td>7–73% </td></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;color:inherit;"><b>Lethal dose</b> or concentration (LD, LC): </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">LD<sub>50</sub> (<a href="/wiki/Lethal_dose#LD50" title="Lethal dose">median dose</a>)</div> </td> <td>100 mg/kg (oral, rat)<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> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">LC<sub>50</sub> (<a href="/wiki/Lethal_dose#LC50" title="Lethal dose">median concentration</a>)</div> </td> <td>333 ppm (mouse, 2 <a href="/wiki/Hour" title="Hour">h</a>)<br />815 ppm (rat, 30 min)<sup id="cite_ref-IDLH_13-0" class="reference"><a href="#cite_note-IDLH-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">LC<sub>Lo</sub> (<a href="/wiki/Lethal_dose#LCLo" title="Lethal dose">lowest published</a>)</div> </td> <td>333 ppm (cat, 2 <a href="/wiki/Hour" title="Hour">h</a>)<sup id="cite_ref-IDLH_13-1" class="reference"><a href="#cite_note-IDLH-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;color:inherit;"><a href="/wiki/National_Institute_for_Occupational_Safety_and_Health" title="National Institute for Occupational Safety and Health"><b>NIOSH</b></a> (US health exposure limits): </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Permissible_exposure_limit" title="Permissible exposure limit">PEL</a> (Permissible)</div> </td> <td>TWA 0.75 ppm ST 2 ppm (as formaldehyde and formalin)<sup id="cite_ref-PGCH_10-0" class="reference"><a href="#cite_note-PGCH-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Recommended_exposure_limit" title="Recommended exposure limit">REL</a> (Recommended)</div> </td> <td>Ca TWA 0.016 ppm C 0.1 ppm [15-minute]<sup id="cite_ref-PGCH_10-1" class="reference"><a href="#cite_note-PGCH-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/IDLH" class="mw-redirect" title="IDLH">IDLH</a> (Immediate danger)</div> </td> <td>Ca [20 ppm]<sup id="cite_ref-PGCH_10-2" class="reference"><a href="#cite_note-PGCH-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Safety_data_sheet" title="Safety data sheet">Safety data sheet</a> (SDS) </td> <td><a rel="nofollow" class="external text" href="https://www.fishersci.com/shop/msdsproxy?productName=F75P1GAL&productDescription=formaldehyde--by-weight-histological-fisher-chemical&catNo=F75P-1GAL&vendorId=VN00000001&storeId=10652">MSDS</a>(<a rel="nofollow" class="external text" href="https://web.archive.org/web/20170918021414/https://www.fishersci.com/shop/msdsproxy?productName=F75P1GAL&productDescription=formaldehyde--by-weight-histological-fisher-chemical&catNo=F75P-1GAL&vendorId=VN00000001&storeId=10652">Archived</a>) </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Related compounds </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Related <a href="/wiki/Aldehyde" title="Aldehyde">aldehydes</a></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a href="/wiki/Acetaldehyde" title="Acetaldehyde">Acetaldehyde</a></li><li><a href="/wiki/Propionaldehyde" title="Propionaldehyde">Propionaldehyde</a></li><li><a href="/wiki/Butyraldehyde" title="Butyraldehyde">Butyraldehyde</a></li><li><a href="/wiki/Pentanal" title="Pentanal">Pentanal</a></li><li><a href="/wiki/Hexanal" title="Hexanal">Hexanal</a></li><li><a href="/wiki/Heptanal" title="Heptanal">Heptanal</a></li><li><a href="/wiki/Octanal" title="Octanal">Octanal</a></li><li><a href="/wiki/Nonanal" title="Nonanal">Nonanal</a></li><li><a href="/wiki/Decanal" title="Decanal">Decanal</a></li><li><a href="/wiki/Octadecanal" title="Octadecanal">Octadecanal</a></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Related compounds</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a href="/wiki/Methanol" title="Methanol">Methanol</a></li><li><a href="/wiki/Formic_acid" title="Formic acid">Formic acid</a></li><li><a href="/wiki/Methanimine" class="mw-redirect" title="Methanimine">Methanimine</a></li><li><a href="/wiki/Ethylene" title="Ethylene">Ethylene</a></li><li><a href="/wiki/Phosgene" title="Phosgene">Phosgene</a></li><li><a href="/wiki/Carbonyl_fluoride" title="Carbonyl fluoride">Carbonyl fluoride</a></li><li><a href="/wiki/Thioformaldehyde" title="Thioformaldehyde">Thioformaldehyde</a></li></ul></div> </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; color:inherit; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"><div style="text-align:center;"><span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/12px-Yes_check.svg.png" decoding="async" width="12" height="12" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/18px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/24px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span> <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=464368486&page2=Formaldehyde">verify</a></span> (<a href="/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validation" title="Wikipedia:WikiProject Chemicals/Chembox validation">what is</a> <sup><span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup> ?) </div></div> <div style="margin-top: 0.3em; text-align: center;"><a href="/wiki/Wikipedia:Chemical_infobox#References" title="Wikipedia:Chemical infobox">Infobox references</a></div> </td></tr> </tbody></table><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound</div> <p><b>Formaldehyde</b> (<span class="rt-commentedText nowrap"><span class="IPA nopopups noexcerpt" lang="en-fonipa"><a href="/wiki/Help:IPA/English" title="Help:IPA/English">/<span style="border-bottom:1px dotted"><span title="'f' in 'find'">f</span><span title="/ɔːr/: 'ar' in 'war'">ɔːr</span><span title="/ˈ/: primary stress follows">ˈ</span><span title="'m' in 'my'">m</span><span title="/æ/: 'a' in 'bad'">æ</span><span title="'l' in 'lie'">l</span><span title="'d' in 'dye'">d</span><span title="/ɪ/: 'i' in 'kit'">ɪ</span><span title="'h' in 'hi'">h</span><span title="/aɪ/: 'i' in 'tide'">aɪ</span><span title="'d' in 'dye'">d</span></span>/</a></span> <span class="ext-phonos"><span data-nosnippet="" id="ooui-php-1" class="noexcerpt ext-phonos-PhonosButton ext-phonos-PhonosButton-emptylabel oo-ui-widget oo-ui-widget-enabled oo-ui-buttonElement oo-ui-buttonElement-frameless oo-ui-iconElement oo-ui-buttonWidget" data-ooui="{"_":"mw.Phonos.PhonosButton","href":"\/\/upload.wikimedia.org\/wikipedia\/commons\/transcoded\/e\/e3\/En-us-Formaldehyde2.ogg\/En-us-Formaldehyde2.ogg.mp3","rel":["nofollow"],"framed":false,"icon":"volumeUp","data":{"ipa":"","text":"","lang":"en","wikibase":"","file":"En-us-Formaldehyde2.ogg"},"classes":["noexcerpt","ext-phonos-PhonosButton","ext-phonos-PhonosButton-emptylabel"]}"><a role="button" tabindex="0" href="//upload.wikimedia.org/wikipedia/commons/transcoded/e/e3/En-us-Formaldehyde2.ogg/En-us-Formaldehyde2.ogg.mp3" rel="nofollow" aria-label="Play audio" title="Play audio" class="oo-ui-buttonElement-button"><span class="oo-ui-iconElement-icon oo-ui-icon-volumeUp"></span><span class="oo-ui-labelElement-label"></span><span class="oo-ui-indicatorElement-indicator oo-ui-indicatorElement-noIndicator"></span></a></span><sup class="ext-phonos-attribution noexcerpt navigation-not-searchable"><a href="/wiki/File:En-us-Formaldehyde2.ogg" title="File:En-us-Formaldehyde2.ogg">ⓘ</a></sup></span></span> <a href="/wiki/Help:Pronunciation_respelling_key" title="Help:Pronunciation respelling key"><i title="English pronunciation respelling">for-<span style="font-size:90%">MAL</span>-di-hide</i></a>, <span class="rt-commentedText nowrap"><style data-mw-deduplicate="TemplateStyles:r1177148991">.mw-parser-output .IPA-label-small{font-size:85%}.mw-parser-output .references .IPA-label-small,.mw-parser-output .infobox .IPA-label-small,.mw-parser-output .navbox .IPA-label-small{font-size:100%}</style><span class="IPA-label IPA-label-small"><a href="/wiki/American_English" title="American English">US</a> also </span><span class="IPA nopopups noexcerpt" lang="en-fonipa"><a href="/wiki/Help:IPA/English" title="Help:IPA/English">/<span style="border-bottom:1px dotted"><span title="'f' in 'find'">f</span><span title="/ə/: 'a' in 'about'">ə</span><span title="'r' in 'rye'">r</span></span>-/</a></span> <span class="ext-phonos"><span data-nosnippet="" id="ooui-php-2" class="noexcerpt ext-phonos-PhonosButton ext-phonos-PhonosButton-emptylabel oo-ui-widget oo-ui-widget-enabled oo-ui-buttonElement oo-ui-buttonElement-frameless oo-ui-iconElement oo-ui-buttonWidget" data-ooui="{"_":"mw.Phonos.PhonosButton","href":"\/\/upload.wikimedia.org\/wikipedia\/commons\/transcoded\/f\/f4\/En-us-Formaldehyde.ogg\/En-us-Formaldehyde.ogg.mp3","rel":["nofollow"],"framed":false,"icon":"volumeUp","data":{"ipa":"","text":"","lang":"en","wikibase":"","file":"En-us-Formaldehyde.ogg"},"classes":["noexcerpt","ext-phonos-PhonosButton","ext-phonos-PhonosButton-emptylabel"]}"><a role="button" tabindex="0" href="//upload.wikimedia.org/wikipedia/commons/transcoded/f/f4/En-us-Formaldehyde.ogg/En-us-Formaldehyde.ogg.mp3" rel="nofollow" aria-label="Play audio" title="Play audio" class="oo-ui-buttonElement-button"><span class="oo-ui-iconElement-icon oo-ui-icon-volumeUp"></span><span class="oo-ui-labelElement-label"></span><span class="oo-ui-indicatorElement-indicator oo-ui-indicatorElement-noIndicator"></span></a></span><sup class="ext-phonos-attribution noexcerpt navigation-not-searchable"><a href="/wiki/File:En-us-Formaldehyde.ogg" title="File:En-us-Formaldehyde.ogg">ⓘ</a></sup></span></span> <a href="/wiki/Help:Pronunciation_respelling_key" title="Help:Pronunciation respelling key"><i title="English pronunciation respelling">fər-</i></a>) (<a href="/wiki/Preferred_IUPAC_name" title="Preferred IUPAC name">systematic name</a> <b>methanal</b>) is an <a href="/wiki/Organic_compound" title="Organic compound">organic compound</a> with the <a href="/wiki/Chemical_formula" title="Chemical formula">chemical formula</a> <style data-mw-deduplicate="TemplateStyles:r1123817410">.mw-parser-output .template-chem2-su{display:inline-block;font-size:80%;line-height:1;vertical-align:-0.35em}.mw-parser-output .template-chem2-su>span{display:block;text-align:left}.mw-parser-output sub.template-chem2-sub{font-size:80%;vertical-align:-0.35em}.mw-parser-output sup.template-chem2-sup{font-size:80%;vertical-align:0.65em}</style><span class="chemf nowrap">CH<sub class="template-chem2-sub">2</sub>O</span> and structure <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">H−CHO</span>, more precisely <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">H<sub class="template-chem2-sub">2</sub>C=O</span>. The compound is a pungent, colourless gas that <a href="/wiki/Polymerization" title="Polymerization">polymerises</a> spontaneously into <a href="/wiki/Paraformaldehyde" title="Paraformaldehyde">paraformaldehyde</a>. It is stored as aqueous solutions (<b>formalin</b>), which consists mainly of the hydrate CH<sub>2</sub>(OH)<sub>2</sub>. It is the simplest of the <a href="/wiki/Aldehyde" title="Aldehyde">aldehydes</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">R−CHO</span>). As a precursor to many other materials and chemical compounds, in 2006 the global production of formaldehyde was estimated at 12 million tons per year.<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> It is mainly used in the production of industrial <a href="/wiki/Resin" title="Resin">resins</a>, e.g., for <a href="/wiki/Particle_board" title="Particle board">particle board</a> and <a href="/wiki/Coating" title="Coating">coatings</a>. Small amounts also occur naturally. </p><p>Formaldehyde is classified as a <a href="/wiki/Carcinogen" title="Carcinogen">carcinogen</a><sup id="cite_ref-carcinogen_16-0" class="reference"><a href="#cite_note-carcinogen-16"><span class="cite-bracket">[</span>note 1<span class="cite-bracket">]</span></a></sup> and can cause respiratory and skin <a href="/wiki/Irritation" title="Irritation">irritation</a> upon exposure.<sup id="cite_ref-cancer.gov_15-1" class="reference"><a href="#cite_note-cancer.gov-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Forms">Forms</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Formaldehyde&action=edit&section=1" title="Edit section: Forms"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Formaldehyde is more complicated than many simple carbon compounds in that it adopts several diverse forms. These compounds can often be used interchangeably and can be interconverted.<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. (January 2025)">citation needed</span></a></i>]</sup> </p> <ul><li>Molecular formaldehyde. A colorless gas with a characteristic pungent, irritating odor. It is stable at about 150 °C, but it polymerizes when condensed to a liquid.</li> <li><a href="/wiki/1,3,5-Trioxane" title="1,3,5-Trioxane">1,3,5-Trioxane</a>, with the formula (CH<sub>2</sub>O)<sub>3</sub>. It is a white solid that dissolves without degradation in organic solvents. It is a <a href="/wiki/Trimer_(chemistry)" title="Trimer (chemistry)">trimer</a> of molecular formaldehyde.</li> <li><a href="/wiki/Paraformaldehyde" title="Paraformaldehyde">Paraformaldehyde</a>, with the formula HO(CH<sub>2</sub>O)<sub>n</sub>H. It is a white solid that is insoluble in most solvents.</li> <li><a href="/wiki/Methanediol" title="Methanediol">Methanediol</a>, with the formula CH<sub>2</sub>(OH)<sub>2</sub>. This compound also exists in equilibrium with various <a href="/wiki/Oligomer" title="Oligomer">oligomers</a> (short polymers), depending on the concentration and temperature. A saturated water solution, of about 40% formaldehyde by volume or 37% by mass, is called "100% formalin".</li></ul> <p>A small amount of <a href="/wiki/Stabilizer_(chemistry)" title="Stabilizer (chemistry)">stabilizer</a>, such as <a href="/wiki/Methanol" title="Methanol">methanol</a>, is usually added to suppress <a href="/wiki/Oxidation" class="mw-redirect" title="Oxidation">oxidation</a> and <a href="/wiki/Polymerization" title="Polymerization">polymerization</a>. A typical commercial-grade formalin may contain 10–12% methanol in addition to various metallic impurities. </p><p>"Formaldehyde" was first used as a <a href="/wiki/Generic_trademark" title="Generic trademark">generic trademark</a> in 1893 following a previous trade name, "formalin".<sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p> <ul class="gallery mw-gallery-traditional"> <li class="gallerycaption">Main forms of formaldehyde</li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Structural_formula_of_formaldehyde.svg" class="mw-file-description" title="Monomeric formaldehyde (subject of this article)"><img alt="Monomeric formaldehyde (subject of this article)" src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0c/Structural_formula_of_formaldehyde.svg/120px-Structural_formula_of_formaldehyde.svg.png" decoding="async" width="120" height="112" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0c/Structural_formula_of_formaldehyde.svg/180px-Structural_formula_of_formaldehyde.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/0c/Structural_formula_of_formaldehyde.svg/240px-Structural_formula_of_formaldehyde.svg.png 2x" data-file-width="114" data-file-height="106" /></a></span></div> <div class="gallerytext">Monomeric formaldehyde (subject of this article)</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:S-Trioxane.svg" class="mw-file-description" title="Trioxane is a stable cyclic trimer of formaldehyde."><img alt="Trioxane is a stable cyclic trimer of formaldehyde." src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b9/S-Trioxane.svg/114px-S-Trioxane.svg.png" decoding="async" width="114" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b9/S-Trioxane.svg/170px-S-Trioxane.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b9/S-Trioxane.svg/227px-S-Trioxane.svg.png 2x" data-file-width="303" data-file-height="320" /></a></span></div> <div class="gallerytext">Trioxane is a stable cyclic trimer of formaldehyde.</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Paraformaldehyd.svg" class="mw-file-description" title="Paraformaldehyde is a common form of formaldehyde for industrial applications."><img alt="Paraformaldehyde is a common form of formaldehyde for industrial applications." src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f4/Paraformaldehyd.svg/120px-Paraformaldehyd.svg.png" decoding="async" width="120" height="74" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f4/Paraformaldehyd.svg/180px-Paraformaldehyd.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f4/Paraformaldehyd.svg/240px-Paraformaldehyd.svg.png 2x" data-file-width="176" data-file-height="108" /></a></span></div> <div class="gallerytext">Paraformaldehyde is a common form of formaldehyde for industrial applications.</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Methanediol-2D.png" class="mw-file-description" title="Methanediol, the predominant species in dilute aqueous solutions of formaldehyde"><img alt="Methanediol, the predominant species in dilute aqueous solutions of formaldehyde" src="//upload.wikimedia.org/wikipedia/commons/thumb/1/15/Methanediol-2D.png/120px-Methanediol-2D.png" decoding="async" width="120" height="104" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/15/Methanediol-2D.png/180px-Methanediol-2D.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/15/Methanediol-2D.png/240px-Methanediol-2D.png 2x" data-file-width="912" data-file-height="792" /></a></span></div> <div class="gallerytext">Methanediol, the predominant species in dilute aqueous solutions of formaldehyde</div> </li> </ul> <div class="mw-heading mw-heading3"><h3 id="Structure_and_bonding">Structure and bonding</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Formaldehyde&action=edit&section=2" title="Edit section: Structure and bonding"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Molecular formaldehyde contains a central carbon atom with a <a href="/wiki/Carbonyl_group" title="Carbonyl group">double bond to the oxygen atom</a> and a <a href="/wiki/Carbon%E2%80%93hydrogen_bond" title="Carbon–hydrogen bond">single bond to each hydrogen atom</a>. This structure is summarised by the <a href="/wiki/Structural_formula#Condensed_formulas" title="Structural formula">condensed formula</a> H<sub>2</sub>C=O.<sup id="cite_ref-Wells_18-0" class="reference"><a href="#cite_note-Wells-18"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> The molecule is planar, Y-shaped and its <a href="/wiki/Molecular_symmetry" title="Molecular symmetry">molecular symmetry</a> belongs to the <a href="/wiki/Molecular_symmetry#Common_point_groups" title="Molecular symmetry"><i>C</i><sub>2v</sub> point group</a>.<sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> The precise <a href="/wiki/Molecular_geometry" title="Molecular geometry">molecular geometry</a> of gaseous formaldehyde has been determined by <a href="/wiki/Gas_electron_diffraction" title="Gas electron diffraction">gas electron diffraction</a><sup id="cite_ref-Wells_18-1" class="reference"><a href="#cite_note-Wells-18"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-CKIM_20-0" class="reference"><a href="#cite_note-CKIM-20"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> and <a href="/wiki/Microwave_spectroscopy" title="Microwave spectroscopy">microwave spectroscopy</a>.<sup id="cite_ref-CRC_21-0" class="reference"><a href="#cite_note-CRC-21"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Duncan_22-0" class="reference"><a href="#cite_note-Duncan-22"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> The <a href="/wiki/Bond_length" title="Bond length">bond lengths</a> are 1.21 <a href="/wiki/%C3%85ngstrom" class="mw-redirect" title="Ångstrom">Å</a> for the <a href="/wiki/Carbon%E2%80%93oxygen_bond" title="Carbon–oxygen bond">carbon–oxygen bond</a><sup id="cite_ref-Wells_18-2" class="reference"><a href="#cite_note-Wells-18"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-CKIM_20-1" class="reference"><a href="#cite_note-CKIM-20"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-CRC_21-1" class="reference"><a href="#cite_note-CRC-21"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Duncan_22-1" class="reference"><a href="#cite_note-Duncan-22"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-March_23-0" class="reference"><a href="#cite_note-March-23"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> and around 1.11 Å for the <a href="/wiki/Carbon%E2%80%93hydrogen_bond" title="Carbon–hydrogen bond">carbon–hydrogen bond</a>,<sup id="cite_ref-Wells_18-3" class="reference"><a href="#cite_note-Wells-18"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-CKIM_20-2" class="reference"><a href="#cite_note-CKIM-20"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-CRC_21-2" class="reference"><a href="#cite_note-CRC-21"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Duncan_22-2" class="reference"><a href="#cite_note-Duncan-22"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> while the H–C–H <a href="/wiki/Bond_angle" class="mw-redirect" title="Bond angle">bond angle</a> is 117°,<sup id="cite_ref-CRC_21-3" class="reference"><a href="#cite_note-CRC-21"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Duncan_22-3" class="reference"><a href="#cite_note-Duncan-22"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> close to the 120° angle found in an ideal <a href="/wiki/Trigonal_planar_molecular_geometry" title="Trigonal planar molecular geometry">trigonal planar molecule</a>.<sup id="cite_ref-Wells_18-4" class="reference"><a href="#cite_note-Wells-18"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> Some <a href="/wiki/Excited_state" title="Excited state">excited electronic states</a> of formaldehyde are <a href="/wiki/Trigonal_pyramidal_molecular_geometry" title="Trigonal pyramidal molecular geometry">pyramidal</a> rather than planar as in the <a href="/wiki/Ground_state" title="Ground state">ground state</a>.<sup id="cite_ref-March_23-1" class="reference"><a href="#cite_note-March-23"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Occurrence">Occurrence</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Formaldehyde&action=edit&section=3" title="Edit section: Occurrence"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Processes in the upper <a href="/wiki/Earth%27s_atmosphere" class="mw-redirect" title="Earth's atmosphere">atmosphere</a> contribute more than 80% of the total formaldehyde in the environment.<sup id="cite_ref-24" class="reference"><a href="#cite_note-24"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> Formaldehyde is an intermediate in the oxidation (or <a href="/wiki/Combustion" title="Combustion">combustion</a>) of <a href="/wiki/Methane" title="Methane">methane</a>, as well as of other carbon compounds, e.g. in <a href="/wiki/Forest_fire" class="mw-redirect" title="Forest fire">forest fires</a>, <a href="/wiki/Automobile" class="mw-redirect" title="Automobile">automobile</a> exhaust, and <a href="/wiki/Tobacco_smoke" title="Tobacco smoke">tobacco smoke</a>. When produced in the atmosphere by the action of sunlight and <a href="/wiki/Oxygen" title="Oxygen">oxygen</a> on <a href="/wiki/Atmospheric_methane" title="Atmospheric methane">atmospheric methane</a> and other <a href="/wiki/Hydrocarbon" title="Hydrocarbon">hydrocarbons</a>, it becomes part of <a href="/wiki/Smog" title="Smog">smog</a>. Formaldehyde has also been detected in outer space. </p><p>Formaldehyde and its <a href="/wiki/Adducts" class="mw-redirect" title="Adducts">adducts</a> are ubiquitous in nature. Food may contain formaldehyde at levels 1–100 mg/kg.<sup id="cite_ref-25" class="reference"><a href="#cite_note-25"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> Formaldehyde, formed in the metabolism of the amino acids <a href="/wiki/Serine" title="Serine">serine</a> and <a href="/wiki/Threonine" title="Threonine">threonine</a>, is found in the bloodstream of humans and other primates at concentrations of approximately 50 <a href="/wiki/Micromolar" class="mw-redirect" title="Micromolar">micromolar</a>.<sup id="cite_ref-Chang_26-0" class="reference"><a href="#cite_note-Chang-26"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> Experiments in which animals are exposed to an atmosphere containing isotopically labeled formaldehyde have demonstrated that even in deliberately exposed animals, the majority of formaldehyde-DNA adducts found in non-respiratory tissues are derived from endogenously produced formaldehyde.<sup id="cite_ref-27" class="reference"><a href="#cite_note-27"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> </p><p>Formaldehyde does not accumulate in the environment, because it is broken down within a few hours by sunlight or by bacteria present in soil or water. Humans metabolize formaldehyde quickly, converting it to <a href="/wiki/Formic_acid" title="Formic acid">formic acid</a>.<sup id="cite_ref-28" class="reference"><a href="#cite_note-28"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-29" class="reference"><a href="#cite_note-29"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> It nonetheless presents <a href="#Safety">significant health concerns</a>, as a <a href="/wiki/Contaminant" class="mw-redirect" title="Contaminant">contaminant</a>. </p> <div class="mw-heading mw-heading3"><h3 id="Interstellar_formaldehyde">Interstellar formaldehyde</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Formaldehyde&action=edit&section=4" title="Edit section: Interstellar formaldehyde"><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/Interstellar_formaldehyde" title="Interstellar formaldehyde">Interstellar formaldehyde</a></div> <p>Formaldehyde appears to be a useful probe in astrochemistry due to prominence of the 1<sub>10</sub>←1<sub>11</sub> and 2<sub>11</sub>←2<sub>12</sub> <i>K</i>-doublet transitions. It was the first polyatomic <a href="/wiki/Organic_chemistry" title="Organic chemistry">organic</a> molecule detected in the <a href="/wiki/Interstellar_medium" title="Interstellar medium">interstellar medium</a>.<sup id="cite_ref-30" class="reference"><a href="#cite_note-30"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> Since its initial detection in 1969, it has been observed in many regions of the <a href="/wiki/Milky_Way_galaxy" class="mw-redirect" title="Milky Way galaxy">galaxy</a>. Because of the widespread interest in interstellar formaldehyde, it has been extensively studied, yielding new extragalactic sources.<sup id="cite_ref-mangum_31-0" class="reference"><a href="#cite_note-mangum-31"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> A proposed mechanism for the formation is the hydrogenation of CO ice:<sup id="cite_ref-Woon_32-0" class="reference"><a href="#cite_note-Woon-32"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> </p> <dl><dd>H + CO → HCO</dd> <dd>HCO + H → CH<sub>2</sub>O</dd></dl> <p><a href="/wiki/Hydrogen_cyanide" title="Hydrogen cyanide">HCN</a>, <a href="/wiki/Hydrogen_isocyanide" title="Hydrogen isocyanide">HNC</a>, H<sub>2</sub>CO, and <a href="/wiki/Dust" title="Dust">dust</a> have also been observed inside the <a href="/wiki/Coma_(cometary)" class="mw-redirect" title="Coma (cometary)">comae</a> of <a href="/wiki/Comet" title="Comet">comets</a> <a href="/wiki/C/2012_F6_(Lemmon)" title="C/2012 F6 (Lemmon)">C/2012 F6 (Lemmon)</a> and <a href="/wiki/Comet_ISON" title="Comet ISON">C/2012 S1 (ISON)</a>.<sup id="cite_ref-NASA-20140811_33-0" class="reference"><a href="#cite_note-NASA-20140811-33"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-AJL-20140811_34-0" class="reference"><a href="#cite_note-AJL-20140811-34"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Synthesis_and_industrial_production">Synthesis and industrial production</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Formaldehyde&action=edit&section=5" title="Edit section: Synthesis and industrial production"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Laboratory_synthesis">Laboratory synthesis</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Formaldehyde&action=edit&section=6" title="Edit section: Laboratory synthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Formaldehyde was discovered in 1859 by the Russian chemist <a href="/wiki/Aleksandr_Butlerov" class="mw-redirect" title="Aleksandr Butlerov">Aleksandr Butlerov</a> (1828–1886) when he attempted to synthesize methanediol ("methylene glycol") from <a href="/wiki/Iodomethane" title="Iodomethane">iodomethane</a> and <a href="/wiki/Silver_oxalate" title="Silver oxalate">silver oxalate</a>.<sup id="cite_ref-35" class="reference"><a href="#cite_note-35"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> In his paper, Butlerov referred to formaldehyde as "dioxymethylen" (methylene dioxide) because his empirical formula for it was incorrect, as atomic weights were not precisely determined until the <a href="/wiki/Karlsruhe_Congress" title="Karlsruhe Congress">Karlsruhe Congress</a>. </p><p>The compound was identified as an aldehyde by <a href="/wiki/August_Wilhelm_von_Hofmann" title="August Wilhelm von Hofmann">August Wilhelm von Hofmann</a>, who first announced its production by passing methanol vapor in air over hot platinum wire.<sup id="cite_ref-36" class="reference"><a href="#cite_note-36"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-37" class="reference"><a href="#cite_note-37"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup> With modifications, Hofmann's method remains the basis of the present day industrial route. </p><p>Solution routes to formaldehyde also entail oxidation of methanol or <a href="/wiki/Iodomethane" title="Iodomethane">iodomethane</a>.<sup id="cite_ref-38" class="reference"><a href="#cite_note-38"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Industry">Industry</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Formaldehyde&action=edit&section=7" title="Edit section: Industry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Formaldehyde is produced industrially by the catalytic oxidation of <a href="/wiki/Methanol" title="Methanol">methanol</a>. The most common catalysts are <a href="/wiki/Silver" title="Silver">silver</a> metal (i.e. the <a href="/wiki/Fasil_process" title="Fasil process">FASIL process</a>), <a href="/wiki/Iron(III)_oxide" title="Iron(III) oxide">iron(III) oxide</a>,<sup id="cite_ref-39" class="reference"><a href="#cite_note-39"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup> iron molybdenum <a href="/wiki/Oxide" title="Oxide">oxides</a> (e.g. iron(III) <a href="/wiki/Molybdate" title="Molybdate">molybdate</a>) with a <a href="/wiki/Molybdenum" title="Molybdenum">molybdenum</a>-enriched surface,<sup id="cite_ref-40" class="reference"><a href="#cite_note-40"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup> or <a href="/wiki/Vanadium_pentoxide" class="mw-redirect" title="Vanadium pentoxide">vanadium</a> <a href="/wiki/Oxide" title="Oxide">oxides</a>. In the commonly used <a href="/wiki/Formox_process" title="Formox process">formox process</a>, methanol and oxygen react at c. 250–400 °C in presence of iron oxide in combination with molybdenum and/or vanadium to produce formaldehyde according to the <a href="/wiki/Chemical_equation" title="Chemical equation">chemical equation</a>:<sup id="cite_ref-Ullmann_41-0" class="reference"><a href="#cite_note-Ullmann-41"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup> </p> <dl><dd>2<span class="nowrap"> </span>CH<sub>3</sub>OH + O<sub>2</sub> → 2<span class="nowrap"> </span>CH<sub>2</sub>O + 2<span class="nowrap"> </span>H<sub>2</sub>O</dd></dl> <p>The silver-based catalyst usually operates at a higher temperature, about 650 °C. Two chemical reactions on it simultaneously produce formaldehyde: that shown above and the <a href="/wiki/Dehydrogenation" title="Dehydrogenation">dehydrogenation</a> reaction: </p> <dl><dd>CH<sub>3</sub>OH → CH<sub>2</sub>O + H<sub>2</sub></dd></dl> <p>In principle, formaldehyde could be generated by oxidation of <a href="/wiki/Methane" title="Methane">methane</a>, but this route is not industrially viable because the methanol is more easily oxidized than methane.<sup id="cite_ref-Ullmann_41-1" class="reference"><a href="#cite_note-Ullmann-41"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Biochemistry">Biochemistry</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Formaldehyde&action=edit&section=8" title="Edit section: Biochemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Formaldehyde is produced via several enzyme-catalyzed routes.<sup id="cite_ref-Kamps_42-0" class="reference"><a href="#cite_note-Kamps-42"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> Living beings, including humans, produce formaldehyde as part of their metabolism. Formaldehyde is key to several bodily functions (e.g. <a href="/wiki/Epigenetic" class="mw-redirect" title="Epigenetic">epigenetics</a><sup id="cite_ref-Chang_26-1" class="reference"><a href="#cite_note-Chang-26"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup>), but its amount must also be tightly controlled to avoid self-poisoning.<sup id="cite_ref-43" class="reference"><a href="#cite_note-43"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup> </p> <ul><li><a href="/wiki/Serine_hydroxymethyltransferase" title="Serine hydroxymethyltransferase">Serine hydroxymethyltransferase</a> can decompose <a href="/wiki/Serine" title="Serine">serine</a> into formaldehyde and <a href="/wiki/Glycine" title="Glycine">glycine</a>, according to this reaction: HOCH<sub>2</sub>CH(NH<sub>2</sub>)CO<sub>2</sub>H → CH<sub>2</sub>O + H<sub>2</sub>C(NH<sub>2</sub>)CO<sub>2</sub>H.</li> <li><a href="/wiki/Methylotroph" title="Methylotroph">Methylotrophic</a> microbes convert methanol into formaldehyde and energy via <a href="/wiki/Methanol_dehydrogenase" title="Methanol dehydrogenase">methanol dehydrogenase</a>: CH<sub>3</sub>OH → CH<sub>2</sub>O + 2e<sup>−</sup> + 2H<sup>+</sup></li> <li>Other routes to formaldehyde include oxidative <a href="/wiki/Demethylation" title="Demethylation">demethylations</a>, <a href="/wiki/Semicarbazide" title="Semicarbazide">semicarbazide</a>-sensitive <a href="/wiki/Amine_oxidase" title="Amine oxidase">amine oxidases</a>, <a href="/wiki/Dimethylglycine_dehydrogenase" title="Dimethylglycine dehydrogenase">dimethylglycine dehydrogenases</a>, <a href="/wiki/Lipid_peroxidase" class="mw-redirect" title="Lipid peroxidase">lipid peroxidases</a>, <a href="/wiki/P450_oxidase" class="mw-redirect" title="P450 oxidase">P450 oxidases</a>, and <i>N</i>-methyl group demethylases.<sup id="cite_ref-Kamps_42-1" class="reference"><a href="#cite_note-Kamps-42"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup></li></ul> <p>Formaldehyde is catabolized by <a href="/wiki/Alcohol_dehydrogenase" title="Alcohol dehydrogenase">alcohol dehydrogenase</a> <a href="/wiki/ADH5" title="ADH5">ADH5</a> and <a href="/wiki/Aldehyde_dehydrogenase" title="Aldehyde dehydrogenase">aldehyde dehydrogenase</a> <a href="/wiki/ALDH2" title="ALDH2">ALDH2</a>.<sup id="cite_ref-44" class="reference"><a href="#cite_note-44"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Organic_chemistry">Organic chemistry</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Formaldehyde&action=edit&section=9" title="Edit section: Organic chemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Formaldehyde is a building block in the synthesis of many other compounds of specialised and industrial significance. It exhibits most of the chemical properties of other aldehydes but is more reactive.<sup id="cite_ref-45" class="reference"><a href="#cite_note-45"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Polymerization_and_hydration">Polymerization and hydration</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Formaldehyde&action=edit&section=10" title="Edit section: Polymerization and hydration"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Monomeric CH<sub>2</sub>O is a gas and is rarely encountered in the laboratory. Aqueous formaldehyde, unlike some other small aldehydes (which need specific conditions to oligomerize through <a href="/wiki/Aldol_condensation" title="Aldol condensation">aldol condensation</a>) oligomerizes spontaneously at a common state. The trimer 1,3,5-trioxane, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">(CH<sub class="template-chem2-sub">2</sub>O)<sub class="template-chem2-sub">3</sub></span>, is a typical oligomer. Many cyclic <a href="/wiki/Oligomer" title="Oligomer">oligomers</a> of other sizes have been isolated. Similarly, formaldehyde hydrates to give the geminal diol <a href="/wiki/Methanediol" title="Methanediol">methanediol</a>, which condenses further to form hydroxy-terminated oligomers HO(CH<sub>2</sub>O)<sub><i>n</i></sub>H. The polymer is called <a href="/wiki/Paraformaldehyde" title="Paraformaldehyde">paraformaldehyde</a>. The higher concentration of formaldehyde—the more equilibrium shifts towards polymerization. Diluting with water or increasing the solution temperature, as well as adding alcohols (such as methanol or ethanol) lowers that tendency. </p><p>Gaseous formaldehyde polymerizes at active sites on vessel walls, but the mechanism of the reaction is unknown.<sup id="cite_ref-46" class="reference"><a href="#cite_note-46"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup> Small amounts of <a href="/wiki/Hydrogen_chloride" title="Hydrogen chloride">hydrogen chloride</a>, <a href="/wiki/Boron_trifluoride" title="Boron trifluoride">boron trifluoride</a>, or <a href="/wiki/Stannic_chloride" class="mw-redirect" title="Stannic chloride">stannic chloride</a> present in gaseous formaldehyde provide the catalytic effect and make the polymerization rapid.<sup id="cite_ref-47" class="reference"><a href="#cite_note-47"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Cross-linking_reactions"><a href="/wiki/Cross-link" title="Cross-link">Cross-linking</a> reactions</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Formaldehyde&action=edit&section=11" title="Edit section: Cross-linking reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Formaldehyde forms cross-links by first combining with a protein to form <a href="/wiki/Methylol" class="mw-redirect" title="Methylol">methylol</a>, which loses a water molecule to form a <a href="/wiki/Schiff_base" title="Schiff base">Schiff base</a>.<sup id="cite_ref-pmid26354429_48-0" class="reference"><a href="#cite_note-pmid26354429-48"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup> The Schiff base can then react with DNA or protein to create a cross-linked product.<sup id="cite_ref-pmid26354429_48-1" class="reference"><a href="#cite_note-pmid26354429-48"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup> This reaction is the basis for the most common process of <a href="/wiki/Fixation_(histology)#Chemical_fixation" title="Fixation (histology)">chemical fixation</a>. </p> <div class="mw-heading mw-heading3"><h3 id="Oxidation_and_reduction">Oxidation and reduction</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Formaldehyde&action=edit&section=12" title="Edit section: Oxidation and reduction"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Formaldehyde is readily <a href="/wiki/Oxidation" class="mw-redirect" title="Oxidation">oxidized</a> by atmospheric oxygen into <a href="/wiki/Formic_acid" title="Formic acid">formic acid</a>. For this reason, commercial formaldehyde is typically contaminated with formic acid. Formaldehyde can be hydrogenated into <a href="/wiki/Methanol" title="Methanol">methanol</a>. </p><p>In the <a href="/wiki/Cannizzaro_reaction" title="Cannizzaro reaction">Cannizzaro reaction</a>, formaldehyde and <a href="/wiki/Base_(chemistry)" title="Base (chemistry)">base</a> react to produce <a href="/wiki/Formic_acid" title="Formic acid">formic acid</a> and methanol, a <a href="/wiki/Disproportionation_reaction" class="mw-redirect" title="Disproportionation reaction">disproportionation reaction</a>. </p> <div class="mw-heading mw-heading3"><h3 id="Hydroxymethylation_and_chloromethylation">Hydroxymethylation and chloromethylation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Formaldehyde&action=edit&section=13" title="Edit section: Hydroxymethylation and chloromethylation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Formaldehyde reacts with many compounds, resulting in <a href="/wiki/Hydroxymethylation" title="Hydroxymethylation">hydroxymethylation</a>: </p> <dl><dd>X-H + CH<sub>2</sub>O → X-CH<sub>2</sub>OH<span class="nowrap">     </span>(X = R<sub>2</sub>N, RC(O)NR', SH).</dd></dl> <p>The resulting hydroxymethyl derivatives typically react further. Thus, amines give <a href="/wiki/Hexahydro-1,3,5-triazine" title="Hexahydro-1,3,5-triazine">hexahydro-1,3,5-triazines</a>: </p> <dl><dd>3<span class="nowrap"> </span>RNH<sub>2</sub> + 3<span class="nowrap"> </span>CH<sub>2</sub>O → (RNCH<sub>2</sub>)<sub>3</sub> + 3<span class="nowrap"> </span>H<sub>2</sub>O</dd></dl> <p>Similarly, when combined with <a href="/wiki/Hydrogen_sulfide" title="Hydrogen sulfide">hydrogen sulfide</a>, it forms <a href="/wiki/Trithiane" class="mw-redirect" title="Trithiane">trithiane</a>:<sup id="cite_ref-49" class="reference"><a href="#cite_note-49"><span class="cite-bracket">[</span>48<span class="cite-bracket">]</span></a></sup> </p> <dl><dd>3<span class="nowrap"> </span>CH<sub>2</sub>O + 3<span class="nowrap"> </span>H<sub>2</sub>S → (CH<sub>2</sub>S)<sub>3</sub> + 3<span class="nowrap"> </span>H<sub>2</sub>O</dd></dl> <p>In the presence of acids, it participates in <a href="/wiki/Electrophilic_aromatic_substitution" title="Electrophilic aromatic substitution">electrophilic aromatic substitution</a> reactions with <a href="/wiki/Aromatic_compound" title="Aromatic compound">aromatic compounds</a> resulting in hydroxymethylated derivatives: </p> <dl><dd>ArH + CH<sub>2</sub>O → ArCH<sub>2</sub>OH</dd></dl> <p>When conducted in the presence of hydrogen chloride, the product is the chloromethyl compound, as described in the <a href="/wiki/Blanc_chloromethylation" title="Blanc chloromethylation">Blanc chloromethylation</a>. If the arene is electron-rich, as in phenols, elaborate condensations ensue. With 4-substituted phenols one obtains <a href="/wiki/Calixarenes" class="mw-redirect" title="Calixarenes">calixarenes</a>.<sup id="cite_ref-50" class="reference"><a href="#cite_note-50"><span class="cite-bracket">[</span>49<span class="cite-bracket">]</span></a></sup> Phenol results in polymers. </p> <div class="mw-heading mw-heading3"><h3 id="Other_reactions">Other reactions</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Formaldehyde&action=edit&section=14" title="Edit section: Other reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Many amino acids react with formaldehyde.<sup id="cite_ref-Kamps_42-2" class="reference"><a href="#cite_note-Kamps-42"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> Cysteine converts to <a href="/wiki/Thioproline" title="Thioproline">thioproline</a>. </p> <div class="mw-heading mw-heading2"><h2 id="Uses">Uses</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Formaldehyde&action=edit&section=15" title="Edit section: Uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Industrial_applications">Industrial applications</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Formaldehyde&action=edit&section=16" title="Edit section: Industrial applications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Formaldehyde is a common precursor to more complex compounds and materials. In approximate order of decreasing consumption, products generated from formaldehyde include <a href="/wiki/Urea_formaldehyde_resin" class="mw-redirect" title="Urea formaldehyde resin">urea formaldehyde resin</a>, <a href="/wiki/Melamine_resin" title="Melamine resin">melamine resin</a>, <a href="/wiki/Phenol_formaldehyde_resin" title="Phenol formaldehyde resin">phenol formaldehyde resin</a>, <a href="/wiki/Polyoxymethylene_plastic" class="mw-redirect" title="Polyoxymethylene plastic">polyoxymethylene plastics</a>, <a href="/wiki/1,4-butanediol" class="mw-redirect" title="1,4-butanediol">1,4-butanediol</a>, and <a href="/wiki/Methylene_diphenyl_diisocyanate" title="Methylene diphenyl diisocyanate">methylene diphenyl diisocyanate</a>.<sup id="cite_ref-Ullmann_41-2" class="reference"><a href="#cite_note-Ullmann-41"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup> The <a href="/wiki/Textile_industry" title="Textile industry">textile industry</a> uses formaldehyde-based resins as <a href="/wiki/Finishing_(textiles)" title="Finishing (textiles)">finishers</a> to make fabrics crease-resistant.<sup id="cite_ref-51" class="reference"><a href="#cite_note-51"><span class="cite-bracket">[</span>50<span class="cite-bracket">]</span></a></sup> </p> <figure typeof="mw:File/Thumb"><a href="/wiki/File:UFresinSyn.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/07/UFresinSyn.svg/340px-UFresinSyn.svg.png" decoding="async" width="340" height="157" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/07/UFresinSyn.svg/510px-UFresinSyn.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/07/UFresinSyn.svg/680px-UFresinSyn.svg.png 2x" data-file-width="2894" data-file-height="1333" /></a><figcaption>Two steps in formation of urea-formaldehyde resin, which is widely used in the production of particle board</figcaption></figure> <p>When condensed with <a href="/wiki/Phenol" title="Phenol">phenol</a>, <a href="/wiki/Urea" title="Urea">urea</a>, or <a href="/wiki/Melamine" title="Melamine">melamine</a>, formaldehyde produces, respectively, hard thermoset phenol formaldehyde resin, urea formaldehyde resin, and melamine resin. These polymers are permanent adhesives used in <a href="/wiki/Plywood" title="Plywood">plywood</a> and <a href="/wiki/Carpet" title="Carpet">carpeting</a>. They are also foamed to make <a href="/wiki/Thermal_insulation" title="Thermal insulation">insulation</a>, or <a href="/wiki/Casting" title="Casting">cast</a> into moulded products. Production of formaldehyde resins accounts for more than half of formaldehyde consumption. </p><p>Formaldehyde is also a precursor to polyfunctional <a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">alcohols</a> such as <a href="/wiki/Pentaerythritol" title="Pentaerythritol">pentaerythritol</a>, which is used to make <a href="/wiki/Paint" title="Paint">paints</a> and <a href="/wiki/Explosive" title="Explosive">explosives</a>. Other formaldehyde derivatives include methylene diphenyl diisocyanate, an important component in <a href="/wiki/Polyurethane" title="Polyurethane">polyurethane</a> paints and foams, and <a href="/wiki/Hexamine" class="mw-redirect" title="Hexamine">hexamine</a>, which is used in phenol-formaldehyde resins as well as the explosive <a href="/wiki/RDX" title="RDX">RDX</a>. </p><p>Condensation with acetaldehyde affords <a href="/wiki/Pentaerythritol" title="Pentaerythritol">pentaerythritol</a>, a chemical necessary in synthesizing <a href="/wiki/PETN" class="mw-redirect" title="PETN">PETN</a>, a high explosive:<sup id="cite_ref-52" class="reference"><a href="#cite_note-52"><span class="cite-bracket">[</span>51<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Pentaerythritol_Synthesis.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/83/Pentaerythritol_Synthesis.svg/600px-Pentaerythritol_Synthesis.svg.png" decoding="async" width="600" height="73" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/83/Pentaerythritol_Synthesis.svg/900px-Pentaerythritol_Synthesis.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/83/Pentaerythritol_Synthesis.svg/1200px-Pentaerythritol_Synthesis.svg.png 2x" data-file-width="793" data-file-height="96" /></a><figcaption></figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="Niche_uses">Niche uses</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Formaldehyde&action=edit&section=17" title="Edit section: Niche uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading4"><h4 id="Disinfectant_and_biocide">Disinfectant and biocide</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Formaldehyde&action=edit&section=18" title="Edit section: Disinfectant and biocide"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>An aqueous solution of formaldehyde can be useful as a disinfectant as it kills most <a href="/wiki/Bacteria" title="Bacteria">bacteria</a> and fungi (including their spores). It is used as an additive in vaccine manufacturing to inactivate toxins and pathogens.<sup id="cite_ref-53" class="reference"><a href="#cite_note-53"><span class="cite-bracket">[</span>52<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Formaldehyde_releaser" title="Formaldehyde releaser">Formaldehyde releasers</a> are used as biocides in personal care products such as cosmetics. Although present at levels not normally considered harmful, they are known to cause allergic <a href="/wiki/Contact_dermatitis" title="Contact dermatitis">contact dermatitis</a> in certain sensitised individuals.<sup id="cite_ref-Formaldehyde_Releasers_54-0" class="reference"><a href="#cite_note-Formaldehyde_Releasers-54"><span class="cite-bracket">[</span>53<span class="cite-bracket">]</span></a></sup> </p><p>Aquarists use formaldehyde as a treatment for the parasites <i><a href="/wiki/Ichthyophthirius_multifiliis" title="Ichthyophthirius multifiliis">Ichthyophthirius multifiliis</a></i> and <i><a href="/wiki/Cryptocaryon_irritans" class="mw-redirect" title="Cryptocaryon irritans">Cryptocaryon irritans</a></i>.<sup id="cite_ref-55" class="reference"><a href="#cite_note-55"><span class="cite-bracket">[</span>54<span class="cite-bracket">]</span></a></sup> Formaldehyde is one of the main disinfectants recommended for destroying <a href="/wiki/Anthrax" title="Anthrax">anthrax</a>.<sup id="cite_ref-56" class="reference"><a href="#cite_note-56"><span class="cite-bracket">[</span>55<span class="cite-bracket">]</span></a></sup> </p><p>Formaldehyde is also approved for use in the manufacture of animal feeds in the US. It is an antimicrobial agent used to maintain complete animal feeds or feed ingredients <i>Salmonella</i> negative for up to 21 days.<sup id="cite_ref-57" class="reference"><a href="#cite_note-57"><span class="cite-bracket">[</span>56<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Tissue_fixative_and_embalming_agent">Tissue fixative and embalming agent</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Formaldehyde&action=edit&section=19" title="Edit section: Tissue fixative and embalming agent"><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:Steve_O%27Shea_injecting_formalin.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/2c/Steve_O%27Shea_injecting_formalin.jpg/220px-Steve_O%27Shea_injecting_formalin.jpg" decoding="async" width="220" height="293" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/2c/Steve_O%27Shea_injecting_formalin.jpg/330px-Steve_O%27Shea_injecting_formalin.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/2c/Steve_O%27Shea_injecting_formalin.jpg/440px-Steve_O%27Shea_injecting_formalin.jpg 2x" data-file-width="480" data-file-height="640" /></a><figcaption>Injecting a <a href="/wiki/Giant_squid" title="Giant squid">giant squid</a> specimen with formalin for preservation</figcaption></figure> <p>Formaldehyde preserves or <a href="/wiki/Fixation_(histology)" title="Fixation (histology)">fixes</a> tissue or cells. The process involves <a href="/wiki/Cross-link" title="Cross-link">cross-linking</a> of primary <a href="/wiki/Amino_group" class="mw-redirect" title="Amino group">amino groups</a>. The European Union has banned the use of formaldehyde as a <a href="/wiki/Biocide" title="Biocide">biocide</a> (including <a href="/wiki/Embalming" title="Embalming">embalming</a>) under the <a href="/wiki/Biocidal_Products_Directive" title="Biocidal Products Directive">Biocidal Products Directive</a> (98/8/EC) due to its carcinogenic properties.<sup id="cite_ref-58" class="reference"><a href="#cite_note-58"><span class="cite-bracket">[</span>57<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-59" class="reference"><a href="#cite_note-59"><span class="cite-bracket">[</span>58<span class="cite-bracket">]</span></a></sup> Countries with a strong tradition of embalming corpses, such as Ireland and other colder-weather countries, have raised concerns. Despite reports to the contrary,<sup id="cite_ref-60" class="reference"><a href="#cite_note-60"><span class="cite-bracket">[</span>59<span class="cite-bracket">]</span></a></sup> no decision on the inclusion of formaldehyde on Annex I of the Biocidal Products Directive for product-type 22 (embalming and taxidermist fluids) had been made as of September 2009<sup class="plainlinks noexcerpt noprint asof-tag update" style="display:none;"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Formaldehyde&action=edit">[update]</a></sup>.<sup id="cite_ref-61" class="reference"><a href="#cite_note-61"><span class="cite-bracket">[</span>60<span class="cite-bracket">]</span></a></sup> </p><p>Formaldehyde-based crosslinking is exploited in <a href="/wiki/ChIP-on-chip" title="ChIP-on-chip">ChIP-on-chip</a> or <a href="/wiki/ChIP-sequencing" class="mw-redirect" title="ChIP-sequencing">ChIP-sequencing</a> genomics experiments, where DNA-binding proteins are cross-linked to their cognate binding sites on the chromosome and analyzed to determine what genes are regulated by the proteins. Formaldehyde is also used as a denaturing agent in <a href="/wiki/RNA" title="RNA">RNA</a> gel <a href="/wiki/Electrophoresis" title="Electrophoresis">electrophoresis</a>, preventing RNA from forming secondary structures. A solution of 4% formaldehyde fixes pathology tissue specimens at about one mm per hour at room temperature. </p> <div class="mw-heading mw-heading4"><h4 id="Drug_testing">Drug testing</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Formaldehyde&action=edit&section=20" title="Edit section: Drug testing"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Formaldehyde and 18 <a href="/wiki/Concentration#Molality" title="Concentration">M</a> (concentrated) <a href="/wiki/Sulfuric_acid" title="Sulfuric acid">sulfuric acid</a> makes <a href="/wiki/Marquis_reagent" title="Marquis reagent">Marquis reagent</a>—which can identify <a href="/wiki/Alkaloid" title="Alkaloid">alkaloids</a> and other compounds. </p> <div class="mw-heading mw-heading3"><h3 id="Photography">Photography</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Formaldehyde&action=edit&section=21" title="Edit section: Photography"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In photography, formaldehyde is used in low concentrations for the process <a href="/wiki/C-41_process" title="C-41 process">C-41</a> (color negative film) stabilizer in the final wash step,<sup id="cite_ref-62" class="reference"><a href="#cite_note-62"><span class="cite-bracket">[</span>61<span class="cite-bracket">]</span></a></sup> as well as in the <a href="/wiki/E-6_process" title="E-6 process">process E-6</a> pre-bleach step, to make it unnecessary in the final wash. Due to improvements in dye coupler chemistry, more modern (2006 or later) E-6 and C-41 films do not need formaldehyde, as their dyes are already stable. </p> <div class="mw-heading mw-heading2"><h2 id="Safety">Safety</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Formaldehyde&action=edit&section=22" title="Edit section: Safety"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In view of its widespread use, toxicity, and volatility, formaldehyde poses a significant danger to human health.<sup id="cite_ref-IARC_63-0" class="reference"><a href="#cite_note-IARC-63"><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>63<span class="cite-bracket">]</span></a></sup> In 2011, the US <a href="/wiki/National_Toxicology_Program" title="National Toxicology Program">National Toxicology Program</a> described formaldehyde as "known to be a human carcinogen".<sup id="cite_ref-Harris_65-0" class="reference"><a href="#cite_note-Harris-65"><span class="cite-bracket">[</span>64<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-12Report2011_66-0" class="reference"><a href="#cite_note-12Report2011-66"><span class="cite-bracket">[</span>65<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-roc2011_67-0" class="reference"><a href="#cite_note-roc2011-67"><span class="cite-bracket">[</span>66<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Chronic_inhalation">Chronic inhalation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Formaldehyde&action=edit&section=23" title="Edit section: Chronic inhalation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1251242444">.mw-parser-output .ambox{border:1px solid #a2a9b1;border-left:10px solid #36c;background-color:#fbfbfb;box-sizing:border-box}.mw-parser-output .ambox+link+.ambox,.mw-parser-output .ambox+link+style+.ambox,.mw-parser-output .ambox+link+link+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+style+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+link+.ambox{margin-top:-1px}html body.mediawiki .mw-parser-output .ambox.mbox-small-left{margin:4px 1em 4px 0;overflow:hidden;width:238px;border-collapse:collapse;font-size:88%;line-height:1.25em}.mw-parser-output .ambox-speedy{border-left:10px solid #b32424;background-color:#fee7e6}.mw-parser-output .ambox-delete{border-left:10px solid #b32424}.mw-parser-output .ambox-content{border-left:10px solid #f28500}.mw-parser-output .ambox-style{border-left:10px solid #fc3}.mw-parser-output .ambox-move{border-left:10px solid #9932cc}.mw-parser-output .ambox-protection{border-left:10px solid #a2a9b1}.mw-parser-output .ambox .mbox-text{border:none;padding:0.25em 0.5em;width:100%}.mw-parser-output .ambox .mbox-image{border:none;padding:2px 0 2px 0.5em;text-align:center}.mw-parser-output .ambox .mbox-imageright{border:none;padding:2px 0.5em 2px 0;text-align:center}.mw-parser-output .ambox .mbox-empty-cell{border:none;padding:0;width:1px}.mw-parser-output .ambox .mbox-image-div{width:52px}@media(min-width:720px){.mw-parser-output .ambox{margin:0 10%}}@media print{body.ns-0 .mw-parser-output .ambox{display:none!important}}</style><table class="box-Cleanup plainlinks metadata ambox ambox-style ambox-Cleanup" role="presentation"><tbody><tr><td class="mbox-image"><div class="mbox-image-div"><span typeof="mw:File"><span><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/f/f2/Edit-clear.svg/40px-Edit-clear.svg.png" decoding="async" width="40" height="40" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/f2/Edit-clear.svg/60px-Edit-clear.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/f2/Edit-clear.svg/80px-Edit-clear.svg.png 2x" data-file-width="48" data-file-height="48" /></span></span></div></td><td class="mbox-text"><div class="mbox-text-span">This section may <b>require <a href="/wiki/Wikipedia:Cleanup" title="Wikipedia:Cleanup">cleanup</a></b> to meet Wikipedia's <a href="/wiki/Wikipedia:Manual_of_Style" title="Wikipedia:Manual of Style">quality standards</a>. The specific problem is: <b>A little too scattered among different types of risks. Needs some reorganization.</b><span class="hide-when-compact"> Please help <a href="/wiki/Special:EditPage/Formaldehyde" title="Special:EditPage/Formaldehyde">improve this section</a> if you can.</span> <span class="date-container"><i>(<span class="date">November 2023</span>)</i></span><span class="hide-when-compact"><i> (<small><a href="/wiki/Help:Maintenance_template_removal" title="Help:Maintenance template removal">Learn how and when to remove this message</a></small>)</i></span></div></td></tr></tbody></table> <p>Concerns are associated with chronic (long-term) exposure by inhalation as may happen from <a href="/wiki/Thermal_decomposition" title="Thermal decomposition">thermal</a> or <a href="/wiki/Chemical_decomposition" title="Chemical decomposition">chemical decomposition</a> of formaldehyde-based resins and the production of formaldehyde resulting from the <a href="/wiki/Combustion" title="Combustion">combustion</a> of a variety of organic compounds (for example, exhaust gases). As formaldehyde resins are used in many <a href="/wiki/Construction_materials" class="mw-redirect" title="Construction materials">construction materials</a>, it is one of the more common <a href="/wiki/Indoor_air_quality" title="Indoor air quality">indoor air pollutants</a>.<sup id="cite_ref-68" class="reference"><a href="#cite_note-68"><span class="cite-bracket">[</span>67<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-69" class="reference"><a href="#cite_note-69"><span class="cite-bracket">[</span>68<span class="cite-bracket">]</span></a></sup> At concentrations above 0.1 ppm in air, formaldehyde can irritate the eyes and <a href="/wiki/Mucous_membrane" title="Mucous membrane">mucous membranes</a>.<sup id="cite_ref-70" class="reference"><a href="#cite_note-70"><span class="cite-bracket">[</span>69<span class="cite-bracket">]</span></a></sup> Formaldehyde inhaled at this concentration may cause headaches, a burning sensation in the throat, and difficulty breathing, and can trigger or aggravate asthma symptoms.<sup id="cite_ref-71" class="reference"><a href="#cite_note-71"><span class="cite-bracket">[</span>70<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-72" class="reference"><a href="#cite_note-72"><span class="cite-bracket">[</span>71<span class="cite-bracket">]</span></a></sup> </p><p>The <a href="/wiki/Centers_for_Disease_Control_and_Prevention" title="Centers for Disease Control and Prevention">CDC</a> considers formaldehyde as a systemic poison. Formaldehyde poisoning can cause permanent changes in the <a href="/wiki/Nervous_system" title="Nervous system">nervous system</a>'s functions.<sup id="cite_ref-cdc1_73-0" class="reference"><a href="#cite_note-cdc1-73"><span class="cite-bracket">[</span>72<span class="cite-bracket">]</span></a></sup> </p><p>A 1988 Canadian study of houses with <a href="/wiki/Urea-formaldehyde" title="Urea-formaldehyde">urea-formaldehyde</a> foam insulation found that formaldehyde levels as low as 0.046 ppm were positively correlated with eye and nasal irritation.<sup id="cite_ref-74" class="reference"><a href="#cite_note-74"><span class="cite-bracket">[</span>73<span class="cite-bracket">]</span></a></sup> A 2009 review of studies has shown a strong association between exposure to formaldehyde and the development of childhood <a href="/wiki/Asthma" title="Asthma">asthma</a>.<sup id="cite_ref-75" class="reference"><a href="#cite_note-75"><span class="cite-bracket">[</span>74<span class="cite-bracket">]</span></a></sup> </p><p>A theory was proposed for the carcinogenesis of formaldehyde in 1978.<sup id="cite_ref-76" class="reference"><a href="#cite_note-76"><span class="cite-bracket">[</span>75<span class="cite-bracket">]</span></a></sup> In 1987 the <a href="/wiki/United_States_Environmental_Protection_Agency" title="United States Environmental Protection Agency">United States Environmental Protection Agency</a> (EPA) classified it as a <i>probable human carcinogen</i>, and after more studies the <a href="/wiki/WHO" class="mw-redirect" title="WHO">WHO</a> <a href="/wiki/International_Agency_for_Research_on_Cancer" title="International Agency for Research on Cancer">International Agency for Research on Cancer</a> (IARC) in 1995 also classified it as a <i>probable human carcinogen</i>. Further information and evaluation of all known data led the IARC to reclassify formaldehyde as a <i>known human carcinogen</i><sup id="cite_ref-International_Agency_for_Research_on_Cancer,_Monographs_Vol_88_77-0" class="reference"><a href="#cite_note-International_Agency_for_Research_on_Cancer,_Monographs_Vol_88-77"><span class="cite-bracket">[</span>76<span class="cite-bracket">]</span></a></sup> associated with nasal sinus cancer and <a href="/wiki/Nasopharyngeal_cancer" class="mw-redirect" title="Nasopharyngeal cancer">nasopharyngeal cancer</a>.<sup id="cite_ref-NCI_78-0" class="reference"><a href="#cite_note-NCI-78"><span class="cite-bracket">[</span>77<span class="cite-bracket">]</span></a></sup> Studies in 2009 and 2010 have also shown a positive correlation between exposure to formaldehyde and the development of <a href="/wiki/Leukemia" title="Leukemia">leukemia</a>, particularly <a href="/wiki/Myeloid_leukemia" title="Myeloid leukemia">myeloid leukemia</a>.<sup id="cite_ref-79" class="reference"><a href="#cite_note-79"><span class="cite-bracket">[</span>78<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-80" class="reference"><a href="#cite_note-80"><span class="cite-bracket">[</span>79<span class="cite-bracket">]</span></a></sup> Nasopharyngeal and sinonasal cancers are relatively rare, with a combined annual incidence in the United States of < 4,000 cases.<sup id="cite_ref-81" class="reference"><a href="#cite_note-81"><span class="cite-bracket">[</span>80<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-82" class="reference"><a href="#cite_note-82"><span class="cite-bracket">[</span>81<span class="cite-bracket">]</span></a></sup> About 30,000 cases of myeloid leukemia occur in the United States each year.<sup id="cite_ref-83" class="reference"><a href="#cite_note-83"><span class="cite-bracket">[</span>82<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-84" class="reference"><a href="#cite_note-84"><span class="cite-bracket">[</span>83<span class="cite-bracket">]</span></a></sup> Some evidence suggests that workplace exposure to formaldehyde contributes to sinonasal cancers.<sup id="cite_ref-cancer.org_85-0" class="reference"><a href="#cite_note-cancer.org-85"><span class="cite-bracket">[</span>84<span class="cite-bracket">]</span></a></sup> Professionals exposed to formaldehyde in their occupation, such as funeral industry workers and <a href="/wiki/Embalming" title="Embalming">embalmers</a>, showed an increased risk of leukemia and brain cancer compared with the general population.<sup id="cite_ref-86" class="reference"><a href="#cite_note-86"><span class="cite-bracket">[</span>85<span class="cite-bracket">]</span></a></sup> Other factors are important in determining individual risk for the development of leukemia or nasopharyngeal cancer.<sup id="cite_ref-cancer.org_85-1" class="reference"><a href="#cite_note-cancer.org-85"><span class="cite-bracket">[</span>84<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-87" class="reference"><a href="#cite_note-87"><span class="cite-bracket">[</span>86<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-88" class="reference"><a href="#cite_note-88"><span class="cite-bracket">[</span>87<span class="cite-bracket">]</span></a></sup> In yeast, formaldehyde is found to perturb pathways for DNA repair and cell cycle.<sup id="cite_ref-89" class="reference"><a href="#cite_note-89"><span class="cite-bracket">[</span>88<span class="cite-bracket">]</span></a></sup> </p><p>In the residential environment, formaldehyde exposure comes from a number of routes; formaldehyde can be emitted by treated <a href="/wiki/Wood" title="Wood">wood</a> products, such as <a href="/wiki/Plywood" title="Plywood">plywood</a> or <a href="/wiki/Particle_board" title="Particle board">particle board</a>, but it is produced by paints, <a href="/wiki/Varnishes" class="mw-redirect" title="Varnishes">varnishes</a>, floor finishes, and <a href="/wiki/Cigarette" title="Cigarette">cigarette</a> smoking as well.<sup id="cite_ref-90" class="reference"><a href="#cite_note-90"><span class="cite-bracket">[</span>89<span class="cite-bracket">]</span></a></sup> In July 2016, the U.S. EPA released a prepublication version of its final rule on Formaldehyde Emission Standards for Composite Wood Products.<sup id="cite_ref-91" class="reference"><a href="#cite_note-91"><span class="cite-bracket">[</span>90<span class="cite-bracket">]</span></a></sup> These new rules impact manufacturers, importers, distributors, and retailers of products containing composite wood, including fiberboard, particleboard, and various laminated products, who must comply with more stringent record-keeping and labeling requirements.<sup id="cite_ref-92" class="reference"><a href="#cite_note-92"><span class="cite-bracket">[</span>91<span class="cite-bracket">]</span></a></sup> </p> <style data-mw-deduplicate="TemplateStyles:r1257001546">.mw-parser-output .infobox-subbox{padding:0;border:none;margin:-3px;width:auto;min-width:100%;font-size:100%;clear:none;float:none;background-color:transparent}.mw-parser-output .infobox-3cols-child{margin:auto}.mw-parser-output .infobox .navbar{font-size:100%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .infobox-full-data:not(.notheme)>div:not(.notheme)[style]{background:#1f1f23!important;color:#f8f9fa}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .infobox-full-data:not(.notheme) div:not(.notheme){background:#1f1f23!important;color:#f8f9fa}}@media(min-width:640px){body.skin--responsive .mw-parser-output .infobox-table{display:table!important}body.skin--responsive .mw-parser-output .infobox-table>caption{display:table-caption!important}body.skin--responsive .mw-parser-output .infobox-table>tbody{display:table-row-group}body.skin--responsive .mw-parser-output .infobox-table tr{display:table-row!important}body.skin--responsive .mw-parser-output .infobox-table th,body.skin--responsive .mw-parser-output .infobox-table td{padding-left:inherit;padding-right:inherit}}</style><table class="infobox" style="width: 210px; clear: right; float:right;margin:0 0 1.5em 1.5em"><tbody><tr><th colspan="2" class="infobox-above" style="font-size:115%">External videos</th></tr><tr><td colspan="2" class="infobox-image"><span typeof="mw:File"><a href="/wiki/File:Fema_trailer_1_Mariel_Carr_Chemical_Heritage_Foundation_Video.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/38/Fema_trailer_1_Mariel_Carr_Chemical_Heritage_Foundation_Video.jpg/200px-Fema_trailer_1_Mariel_Carr_Chemical_Heritage_Foundation_Video.jpg" decoding="async" width="200" height="113" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/38/Fema_trailer_1_Mariel_Carr_Chemical_Heritage_Foundation_Video.jpg/300px-Fema_trailer_1_Mariel_Carr_Chemical_Heritage_Foundation_Video.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/38/Fema_trailer_1_Mariel_Carr_Chemical_Heritage_Foundation_Video.jpg/400px-Fema_trailer_1_Mariel_Carr_Chemical_Heritage_Foundation_Video.jpg 2x" data-file-width="2880" data-file-height="1622" /></a></span></td></tr><tr><td colspan="2" class="infobox-full-data" style="text-align: left"><span typeof="mw:File"><span><img alt="video icon" src="//upload.wikimedia.org/wikipedia/commons/thumb/1/1b/Nuvola_apps_kaboodle.svg/16px-Nuvola_apps_kaboodle.svg.png" decoding="async" width="16" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/1b/Nuvola_apps_kaboodle.svg/24px-Nuvola_apps_kaboodle.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/1b/Nuvola_apps_kaboodle.svg/32px-Nuvola_apps_kaboodle.svg.png 2x" data-file-width="128" data-file-height="128" /></span></span> <a rel="nofollow" class="external text" href="https://www.sciencehistory.org/distillations/video/where-have-all-the-trailers-gone"><i>Where Have All the Trailers Gone?</i></a>, Video by Mariel Carr (Videographer) & Nick Shapiro (Researcher), 2015, <a href="/wiki/Science_History_Institute" title="Science History Institute">Science History Institute</a></td></tr></tbody></table> <p>The U.S. EPA allows no more than 0.016 ppm formaldehyde in the air in new buildings constructed for that agency.<sup id="cite_ref-93" class="reference"><a href="#cite_note-93"><span class="cite-bracket">[</span>92<span class="cite-bracket">]</span></a></sup><sup class="noprint Inline-Template" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Verifiability" title="Wikipedia:Verifiability"><span title="Dead URL & the archived document (multiple versions) doesn't show this limitation. (April 2019)">failed verification</span></a></i>]</sup> A U.S. EPA study found a new home measured 0.076 ppm when brand new and 0.045 ppm after 30 days.<sup id="cite_ref-94" class="reference"><a href="#cite_note-94"><span class="cite-bracket">[</span>93<span class="cite-bracket">]</span></a></sup> The <a href="/wiki/Federal_Emergency_Management_Agency" title="Federal Emergency Management Agency">Federal Emergency Management Agency</a> (FEMA) has also announced limits on the formaldehyde levels in trailers purchased by that agency.<sup id="cite_ref-95" class="reference"><a href="#cite_note-95"><span class="cite-bracket">[</span>94<span class="cite-bracket">]</span></a></sup> The EPA recommends the use of "exterior-grade" pressed-wood products with phenol instead of urea resin to limit formaldehyde exposure, since pressed-wood products containing formaldehyde resins are often a significant source of formaldehyde in homes.<sup id="cite_ref-NCI_78-1" class="reference"><a href="#cite_note-NCI-78"><span class="cite-bracket">[</span>77<span class="cite-bracket">]</span></a></sup> </p><p>The eyes are most sensitive to formaldehyde exposure: The lowest level at which many people can begin to smell formaldehyde ranges between 0.05 and 1 ppm. The maximum concentration value at the workplace is 0.3 ppm.<sup id="cite_ref-96" class="reference"><a href="#cite_note-96"><span class="cite-bracket">[</span>95<span class="cite-bracket">]</span></a></sup><sup class="noprint Inline-Template" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Verifiability" title="Wikipedia:Verifiability"><span title="Quotation needed from source to verify. (April 2019)">need quotation to verify</span></a></i>]</sup> In controlled chamber studies, individuals begin to sense eye irritation at about 0.5 ppm; 5 to 20 percent report eye irritation at 0.5 to 1 ppm; and greater certainty for sensory irritation occurred at 1 ppm and above. While some agencies have used a level as low as 0.1 ppm as a threshold for irritation, the expert panel found that a level of 0.3 ppm would protect against nearly all irritation. In fact, the expert panel found that a level of 1.0 ppm would avoid eye irritation—the most sensitive endpoint—in 75–95% of all people exposed.<sup id="cite_ref-97" class="reference"><a href="#cite_note-97"><span class="cite-bracket">[</span>96<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Rowenta_Intense_Pure_Air_air_purifier.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/bd/Rowenta_Intense_Pure_Air_air_purifier.jpg/170px-Rowenta_Intense_Pure_Air_air_purifier.jpg" decoding="async" width="170" height="299" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/bd/Rowenta_Intense_Pure_Air_air_purifier.jpg/255px-Rowenta_Intense_Pure_Air_air_purifier.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/bd/Rowenta_Intense_Pure_Air_air_purifier.jpg/340px-Rowenta_Intense_Pure_Air_air_purifier.jpg 2x" data-file-width="2304" data-file-height="4056" /></a><figcaption>Some <a href="/wiki/Air_purifier" title="Air purifier">air purifiers</a> include filtering technology that is supposed to lower indoor formaldehyde concentration.</figcaption></figure> <p>Formaldehyde levels in building environments are affected by a number of factors. These include the potency of formaldehyde-emitting products present, the ratio of the surface area of emitting materials to volume of space, environmental factors, product age, interactions with other materials, and ventilation conditions. Formaldehyde emits from a variety of construction materials, furnishings, and consumer products. The three products that emit the highest concentrations are <a href="/wiki/Medium_density_fiberboard" class="mw-redirect" title="Medium density fiberboard">medium density fiberboard</a>, hardwood plywood, and particle board. Environmental factors such as temperature and relative humidity can elevate levels because formaldehyde has a high vapor pressure. Formaldehyde levels from building materials are the highest when a building first opens because materials would have less time to off-gas. Formaldehyde levels decrease over time as the sources suppress. </p><p>In <a href="/wiki/Operating_rooms" class="mw-redirect" title="Operating rooms">operating rooms</a>, formaldehyde is produced as a byproduct of electrosurgery and is present in surgical smoke, exposing surgeons and healthcare workers to potentially unsafe concentrations.<sup id="cite_ref-98" class="reference"><a href="#cite_note-98"><span class="cite-bracket">[</span>97<span class="cite-bracket">]</span></a></sup> </p><p>Formaldehyde levels in air can be sampled and tested in several ways, including impinger, treated sorbent, and passive monitors.<sup id="cite_ref-99" class="reference"><a href="#cite_note-99"><span class="cite-bracket">[</span>98<span class="cite-bracket">]</span></a></sup> The <a href="/wiki/National_Institute_for_Occupational_Safety_and_Health" title="National Institute for Occupational Safety and Health">National Institute for Occupational Safety and Health</a> (NIOSH) has measurement methods numbered 2016, 2541, 3500, and 3800.<sup id="cite_ref-100" class="reference"><a href="#cite_note-100"><span class="cite-bracket">[</span>99<span class="cite-bracket">]</span></a></sup> </p><p>In June 2011, the twelfth edition of the <a href="/wiki/National_Toxicology_Program" title="National Toxicology Program">National Toxicology Program</a> (NTP) Report on Carcinogens (RoC) changed the listing status of formaldehyde from "reasonably anticipated to be a human carcinogen" to "known to be a human carcinogen."<sup id="cite_ref-Harris_65-1" class="reference"><a href="#cite_note-Harris-65"><span class="cite-bracket">[</span>64<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-12Report2011_66-1" class="reference"><a href="#cite_note-12Report2011-66"><span class="cite-bracket">[</span>65<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-roc2011_67-1" class="reference"><a href="#cite_note-roc2011-67"><span class="cite-bracket">[</span>66<span class="cite-bracket">]</span></a></sup> Concurrently, a <a href="/wiki/United_States_National_Academy_of_Sciences" class="mw-redirect" title="United States National Academy of Sciences">National Academy of Sciences</a> (NAS) committee was convened and issued an independent review of the draft U.S. <a href="/wiki/EPA_IRIS" class="mw-redirect" title="EPA IRIS">EPA IRIS</a> assessment of formaldehyde, providing a comprehensive health effects assessment and quantitative estimates of human risks of adverse effects.<sup id="cite_ref-101" class="reference"><a href="#cite_note-101"><span class="cite-bracket">[</span>100<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Acute_irritation_and_allergic_reaction">Acute irritation and allergic reaction</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Formaldehyde&action=edit&section=24" title="Edit section: Acute irritation and allergic reaction"><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:Epikutanni-test.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/4c/Epikutanni-test.jpg/220px-Epikutanni-test.jpg" decoding="async" width="220" height="165" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/4c/Epikutanni-test.jpg/330px-Epikutanni-test.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/4c/Epikutanni-test.jpg/440px-Epikutanni-test.jpg 2x" data-file-width="1600" data-file-height="1200" /></a><figcaption><a href="/wiki/Patch_test" title="Patch test">Patch test</a></figcaption></figure> <p>For most people, irritation from formaldehyde is temporary and reversible, although formaldehyde can cause allergies and is part of the standard patch test series. In 2005–06, it was the seventh-most-prevalent <a href="/wiki/Allergen" title="Allergen">allergen</a> in <a href="/wiki/Patch_test" title="Patch test">patch tests</a> (9.0%).<sup id="cite_ref-102" class="reference"><a href="#cite_note-102"><span class="cite-bracket">[</span>101<span class="cite-bracket">]</span></a></sup> People with formaldehyde allergy are advised to avoid <a href="/wiki/Formaldehyde_releasers" class="mw-redirect" title="Formaldehyde releasers">formaldehyde releasers</a> as well (e.g., <a href="/wiki/Quaternium-15" title="Quaternium-15">Quaternium-15</a>, <a href="/wiki/Imidazolidinyl_urea" title="Imidazolidinyl urea">imidazolidinyl urea</a>, and <a href="/wiki/Diazolidinyl_urea" title="Diazolidinyl urea">diazolidinyl urea</a>).<sup id="cite_ref-103" class="reference"><a href="#cite_note-103"><span class="cite-bracket">[</span>102<span class="cite-bracket">]</span></a></sup> People who suffer allergic reactions to formaldehyde tend to display lesions on the skin in the areas that have had direct contact with the substance, such as the neck or thighs (often due to formaldehyde released from permanent press finished clothing) or <a href="/wiki/Dermatitis" title="Dermatitis">dermatitis</a> on the face (typically from cosmetics).<sup id="cite_ref-Formaldehyde_Releasers_54-1" class="reference"><a href="#cite_note-Formaldehyde_Releasers-54"><span class="cite-bracket">[</span>53<span class="cite-bracket">]</span></a></sup> Formaldehyde has been banned in cosmetics in both <a href="/wiki/Sweden" title="Sweden">Sweden</a><sup id="cite_ref-104" class="reference"><a href="#cite_note-104"><span class="cite-bracket">[</span>103<span class="cite-bracket">]</span></a></sup> and <a href="/wiki/Japan" title="Japan">Japan</a>.<sup id="cite_ref-105" class="reference"><a href="#cite_note-105"><span class="cite-bracket">[</span>104<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Other_routes">Other routes</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Formaldehyde&action=edit&section=25" title="Edit section: Other routes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Formaldehyde occurs naturally, and is "an essential intermediate in cellular metabolism in mammals and humans."<sup id="cite_ref-Ullmann_41-3" class="reference"><a href="#cite_note-Ullmann-41"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup> According to the <a href="/wiki/American_Chemistry_Council" title="American Chemistry Council">American Chemistry Council</a>, "Formaldehyde is found in every living system—from plants to animals to humans. It metabolizes quickly in the body, breaks down rapidly, is not persistent and does not accumulate in the body."<sup id="cite_ref-106" class="reference"><a href="#cite_note-106"><span class="cite-bracket">[</span>105<span class="cite-bracket">]</span></a></sup> </p><p>The twelfth edition of NTP Report on Carcinogens notes that "food and water contain measureable concentrations of formaldehyde, but the significance of ingestion as a source of formaldehyde exposure for the general population is questionable." Food formaldehyde generally occurs in a bound form and formaldehyde is unstable in an aqueous solution.<sup id="cite_ref-roc2011_67-2" class="reference"><a href="#cite_note-roc2011-67"><span class="cite-bracket">[</span>66<span class="cite-bracket">]</span></a></sup> </p><p>In humans, ingestion of as little as 30 millilitres (1.0 US fl oz) of 37% formaldehyde solution can cause death. Other symptoms associated with ingesting such a solution include gastrointestinal damage (vomiting, abdominal pain), and systematic damage (dizziness).<sup id="cite_ref-cdc1_73-1" class="reference"><a href="#cite_note-cdc1-73"><span class="cite-bracket">[</span>72<span class="cite-bracket">]</span></a></sup> Testing for formaldehyde is by blood and/or urine by <a href="/wiki/Gas_chromatography%E2%80%93mass_spectrometry" title="Gas chromatography–mass spectrometry">gas chromatography–mass spectrometry</a>. Other methods include infrared detection, gas detector tubes, etc., of which <a href="/wiki/High-performance_liquid_chromatography" title="High-performance liquid chromatography">high-performance liquid chromatography</a> is the most sensitive.<sup id="cite_ref-107" class="reference"><a href="#cite_note-107"><span class="cite-bracket">[</span>106<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Regulation">Regulation</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Formaldehyde&action=edit&section=26" title="Edit section: Regulation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Several web articles<sup class="noprint Inline-Template" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Avoid_weasel_words" class="mw-redirect" title="Wikipedia:Avoid weasel words"><span title="The material near this tag may use weasel words or too-vague attribution. (June 2022)">like whom?</span></a></i>]</sup> claim that formaldehyde has been banned from manufacture or import into the European Union (EU) under REACH (Registration, Evaluation, Authorization, and restriction of Chemical substances) legislation. That is a misconception, as formaldehyde is not listed in the Annex I of Regulation (EC) No 689/2008 (export and import of dangerous chemicals regulation), nor on a priority list for risk assessment. However, formaldehyde is banned from use in certain applications (preservatives for liquid-cooling and processing systems, <a href="/wiki/Slimicide" title="Slimicide">slimicides</a>, metalworking-fluid preservatives, and antifouling products) under the Biocidal Products Directive.<sup id="cite_ref-108" class="reference"><a href="#cite_note-108"><span class="cite-bracket">[</span>107<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-109" class="reference"><a href="#cite_note-109"><span class="cite-bracket">[</span>108<span class="cite-bracket">]</span></a></sup> In the EU, the maximum allowed concentration of formaldehyde in finished products is 0.2%, and any product that exceeds 0.05% has to include a warning that the product contains formaldehyde.<sup id="cite_ref-Formaldehyde_Releasers_54-2" class="reference"><a href="#cite_note-Formaldehyde_Releasers-54"><span class="cite-bracket">[</span>53<span class="cite-bracket">]</span></a></sup> </p><p>In the United States, <a href="/wiki/United_States_Congress" title="United States Congress">Congress</a> passed a bill July 7, 2010, regarding the use of formaldehyde in hardwood <a href="/wiki/Plywood" title="Plywood">plywood</a>, <a href="/wiki/Particle_board" title="Particle board">particle board</a>, and <a href="/wiki/Medium_density_fiberboard" class="mw-redirect" title="Medium density fiberboard">medium density fiberboard</a>. The bill limited the allowable amount of formaldehyde emissions from these wood products to 0.09 ppm, and required companies to meet this standard by January 2013.<sup id="cite_ref-110" class="reference"><a href="#cite_note-110"><span class="cite-bracket">[</span>109<span class="cite-bracket">]</span></a></sup> The final U.S. EPA rule specified maximum emissions of "0.05 ppm formaldehyde for hardwood plywood, 0.09 ppm formaldehyde for particleboard, 0.11 ppm formaldehyde for medium-density fiberboard, and 0.13 ppm formaldehyde for thin medium-density fiberboard."<sup id="cite_ref-111" class="reference"><a href="#cite_note-111"><span class="cite-bracket">[</span>110<span class="cite-bracket">]</span></a></sup> </p><p>Formaldehyde was declared a toxic substance by the <a href="/wiki/1999_Canadian_Environmental_Protection_Act" class="mw-redirect" title="1999 Canadian Environmental Protection Act">1999 Canadian Environmental Protection Act</a>.<sup id="cite_ref-112" class="reference"><a href="#cite_note-112"><span class="cite-bracket">[</span>111<span class="cite-bracket">]</span></a></sup> </p><p>The <a href="/wiki/FDA" class="mw-redirect" title="FDA">FDA</a> is proposing a ban on hair relaxers with formaldehyde due to cancer concerns.<sup id="cite_ref-113" class="reference"><a href="#cite_note-113"><span class="cite-bracket">[</span>112<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Contaminant_in_food">Contaminant in food</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Formaldehyde&action=edit&section=27" title="Edit section: Contaminant in food"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Scandals have broken in both the <a href="/wiki/2005_Indonesia_food_scare" title="2005 Indonesia food scare">2005 Indonesia food scare</a> and <a href="/wiki/2007_Vietnam_food_scare" title="2007 Vietnam food scare">2007 Vietnam food scare</a> regarding the addition of formaldehyde to foods to extend shelf life. In 2011, after a four-year absence, Indonesian authorities found foods with formaldehyde being sold in markets in a number of regions across the country.<sup id="cite_ref-114" class="reference"><a href="#cite_note-114"><span class="cite-bracket">[</span>113<span class="cite-bracket">]</span></a></sup> In August 2011, at least at two <a href="/wiki/Carrefour" title="Carrefour">Carrefour</a> supermarkets, the Central <a href="/wiki/Jakarta" title="Jakarta">Jakarta</a> Livestock and Fishery Sub-Department found <a href="/wiki/Cendol" title="Cendol">cendol</a> containing 10 <a href="/wiki/Parts_per_million" class="mw-redirect" title="Parts per million">parts per million</a> of formaldehyde.<sup id="cite_ref-115" class="reference"><a href="#cite_note-115"><span class="cite-bracket">[</span>114<span class="cite-bracket">]</span></a></sup> In 2014, the owner of two noodle factories in <a href="/wiki/Bogor" title="Bogor">Bogor</a>, Indonesia, was arrested for using formaldehyde in noodles. 50 kg of formaldehyde was confiscated.<sup id="cite_ref-116" class="reference"><a href="#cite_note-116"><span class="cite-bracket">[</span>115<span class="cite-bracket">]</span></a></sup> Foods known to be contaminated included noodles, salted fish, and tofu. Chicken and beer were also rumored to be contaminated. In some places, such as China, manufacturers still use formaldehyde illegally as a preservative in foods, which exposes people to formaldehyde ingestion.<sup id="cite_ref-117" class="reference"><a href="#cite_note-117"><span class="cite-bracket">[</span>116<span class="cite-bracket">]</span></a></sup> In the early 1900s, it was frequently added by US milk plants to milk bottles as a method of pasteurization due to the lack of knowledge and concern<sup id="cite_ref-118" class="reference"><a href="#cite_note-118"><span class="cite-bracket">[</span>117<span class="cite-bracket">]</span></a></sup> regarding formaldehyde's toxicity.<sup id="cite_ref-119" class="reference"><a href="#cite_note-119"><span class="cite-bracket">[</span>118<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-120" class="reference"><a href="#cite_note-120"><span class="cite-bracket">[</span>119<span class="cite-bracket">]</span></a></sup> </p><p>In 2011 in <a href="/wiki/Nakhon_Ratchasima" title="Nakhon Ratchasima">Nakhon Ratchasima</a>, Thailand, truckloads of rotten chicken were treated with formaldehyde for sale in which "a large network", including 11 slaughterhouses run by a criminal gang, were implicated.<sup id="cite_ref-121" class="reference"><a href="#cite_note-121"><span class="cite-bracket">[</span>120<span class="cite-bracket">]</span></a></sup> In 2012, 1 billion rupiah (almost US$100,000) of fish imported from <a href="/wiki/Pakistan" title="Pakistan">Pakistan</a> to <a href="/wiki/Batam" title="Batam">Batam</a>, Indonesia, were found laced with formaldehyde.<sup id="cite_ref-122" class="reference"><a href="#cite_note-122"><span class="cite-bracket">[</span>121<span class="cite-bracket">]</span></a></sup> </p><p>Formalin contamination of foods has been reported in <a href="/wiki/Bangladesh" title="Bangladesh">Bangladesh</a>, with stores and supermarkets selling fruits, fishes, and vegetables that have been treated with formalin to keep them fresh.<sup id="cite_ref-123" class="reference"><a href="#cite_note-123"><span class="cite-bracket">[</span>122<span class="cite-bracket">]</span></a></sup> However, in 2015, a <i>Formalin Control Bill</i> was passed in the <a href="/wiki/Jatiyo_Sangshad" class="mw-redirect" title="Jatiyo Sangshad">Parliament of Bangladesh</a> with a provision of life-term imprisonment as the maximum punishment as well as a maximum fine of 2,000,000 <a href="/wiki/Bangladeshi_taka" title="Bangladeshi taka">BDT</a> but not less than 500,000 <a href="/wiki/Bangladeshi_taka" title="Bangladeshi taka">BDT</a> for importing, producing, or hoarding formalin without a license.<sup id="cite_ref-124" class="reference"><a href="#cite_note-124"><span class="cite-bracket">[</span>123<span class="cite-bracket">]</span></a></sup> </p><p>Formaldehyde was one of the chemicals used in 19th century industrialised food production that was investigated by Dr. <a href="/wiki/Harvey_W._Wiley" class="mw-redirect" title="Harvey W. Wiley">Harvey W. Wiley</a> with his famous 'Poison Squad' as part of the <a href="/wiki/US_Department_of_Agriculture" class="mw-redirect" title="US Department of Agriculture">US Department of Agriculture</a>. This led to the 1906 <a href="/wiki/Pure_Food_and_Drug_Act" title="Pure Food and Drug Act">Pure Food and Drug Act</a>, a landmark event in the <a href="/wiki/Early_history_of_food_regulation_in_the_United_States" title="Early history of food regulation in the United States">early history of food regulation in the United States</a>.<sup id="cite_ref-125" class="reference"><a href="#cite_note-125"><span class="cite-bracket">[</span>124<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Formaldehyde&action=edit&section=28" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/1,3-Dioxetane" title="1,3-Dioxetane">1,3-Dioxetane</a></li> <li><a href="/wiki/DMDM_hydantoin" title="DMDM hydantoin">DMDM hydantoin</a></li> <li><a href="/wiki/Sawdust" title="Sawdust">Sawdust</a> | <a href="/wiki/Health_impacts_of_sawdust" title="Health impacts of sawdust">Health impacts of sawdust</a></li> <li><a href="/wiki/Sulphobes" title="Sulphobes">Sulphobes</a></li> <li><a href="/wiki/Transition_metal_complexes_of_aldehydes_and_ketones" title="Transition metal complexes of aldehydes and ketones">Transition metal complexes of aldehydes and ketones</a></li> <li><a href="/wiki/Wood_glue" title="Wood glue">Wood glue</a></li> <li><a href="/wiki/Wood_preservation" title="Wood preservation">Wood preservation</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=Formaldehyde&action=edit&section=29" 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-iupac2013-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-iupac2013_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-iupac2013_1-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite class="citation book cs1">"Front Matter". <i>Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book)</i>. 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Hofmann (1868) <a rel="nofollow" class="external text" href="https://books.google.com/books?id=4hNLAAAAYAAJ&pg=PA246">"Zur Kenntnis des Methylaldehyds"</a>, <i>Journal für praktische Chemie</i> (Journal for Practical Chemistry), vol. 103, no. 1, pages 246–250.</li></ul> However, it was not until 1869 that Hofmann determined the correct empirical formula of formaldehyde. See: A.W. Hofmann (5 April 1869) <a rel="nofollow" class="external text" href="https://books.google.com/books?id=58YAAAAAYAAJ&pg=PA362">"Beiträge zur Kenntnis des Methylaldehyds"</a>, <i>Monatsbericht der Königlich Preussischen Akademie der Wissenschaften zu Berlin</i>, vol. ?, pages 362–372. Reprinted in: <ul><li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHofmann1869" class="citation journal cs1">Hofmann, A.W. 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"Formaldehyde in China: Production, consumption, exposure levels, and health effects". <i>Environment International</i>. <b>35</b> (8): <span class="nowrap">1210–</span>1224. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2009EnInt..35.1210T">2009EnInt..35.1210T</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.envint.2009.06.002">10.1016/j.envint.2009.06.002</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0160-4120">0160-4120</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/19589601">19589601</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Environment+International&rft.atitle=Formaldehyde+in+China%3A+Production%2C+consumption%2C+exposure+levels%2C+and+health+effects&rft.volume=35&rft.issue=8&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1210-%3C%2Fspan%3E1224&rft.date=2009&rft_id=info%3Adoi%2F10.1016%2Fj.envint.2009.06.002&rft.issn=0160-4120&rft_id=info%3Apmid%2F19589601&rft_id=info%3Abibcode%2F2009EnInt..35.1210T&rft.aulast=Tang&rft.aufirst=Xiaojiang&rft.au=Bai%2C+Yang&rft.au=Duong%2C+Anh&rft.au=Smith%2C+Martyn+T.&rft.au=Li%2C+Laiyu&rft.au=Zhang%2C+Luoping&rfr_id=info%3Asid%2Fen.wikipedia.org%3AFormaldehyde" class="Z3988"></span></li> <li>see references cited on p. 1216 above</li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation news cs1"><a rel="nofollow" class="external text" href="http://www.chinadaily.com.cn/china/2011-03/18/content_12189671.htm">"Municipality sees red over bad blood processing"</a>. <i>China Daily</i>. 2011-03-18. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20181024232323/http://www.chinadaily.com.cn/china/2011-03/18/content_12189671.htm">Archived</a> from the original on 2018-10-24.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=China+Daily&rft.atitle=Municipality+sees+red+over+bad+blood+processing&rft.date=2011-03-18&rft_id=http%3A%2F%2Fwww.chinadaily.com.cn%2Fchina%2F2011-03%2F18%2Fcontent_12189671.htm&rfr_id=info%3Asid%2Fen.wikipedia.org%3AFormaldehyde" class="Z3988"></span></li></ul> </span></li> <li id="cite_note-118"><span class="mw-cite-backlink"><b><a href="#cite_ref-118">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBlum,_Deborah,_1954-2018" class="citation book cs1">Blum, Deborah, 1954- (2018-09-25). <i>The poison squad: one chemist's single-minded crusade for food safety at the turn of the twentieth century</i>. Go Big Read (Program). New York, New York. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9781594205149" title="Special:BookSources/9781594205149"><bdi>9781594205149</bdi></a>. <a href="/wiki/OCLC_(identifier)" class="mw-redirect" title="OCLC (identifier)">OCLC</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/oclc/1024107182">1024107182</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+poison+squad%3A+one+chemist%27s+single-minded+crusade+for+food+safety+at+the+turn+of+the+twentieth+century&rft.place=New+York%2C+New+York&rft.date=2018-09-25&rft_id=info%3Aoclcnum%2F1024107182&rft.isbn=9781594205149&rft.au=Blum%2C+Deborah%2C+1954-&rfr_id=info%3Asid%2Fen.wikipedia.org%3AFormaldehyde" class="Z3988"></span><span class="cs1-maint citation-comment"><code class="cs1-code">{{<a href="/wiki/Template:Cite_book" title="Template:Cite book">cite book</a>}}</code>: CS1 maint: location missing publisher (<a href="/wiki/Category:CS1_maint:_location_missing_publisher" title="Category:CS1 maint: location missing publisher">link</a>) CS1 maint: multiple names: authors list (<a href="/wiki/Category:CS1_maint:_multiple_names:_authors_list" title="Category:CS1 maint: multiple names: authors list">link</a>) CS1 maint: numeric names: authors list (<a href="/wiki/Category:CS1_maint:_numeric_names:_authors_list" title="Category:CS1 maint: numeric names: authors list">link</a>)</span></span> </li> <li id="cite_note-119"><span class="mw-cite-backlink"><b><a href="#cite_ref-119">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation news cs1"><a rel="nofollow" class="external text" href="https://www.newspapers.com/clip/888392/formaldehyde_in_milk/">"Was Death in the Milk?"</a>. <i>The Indianapolis News</i>. 1900-07-31. p. 5. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20181117064648/https://www.newspapers.com/clip/888392/formaldehyde_in_milk/">Archived</a> from the original on 2018-11-17<span class="reference-accessdate">. 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Food Inspector Farnsworth Would Have Use of Formaldehyde in Milk Stopped"</a>. <i>The Topeka Daily Capital</i>. 1903-08-30. p. 8. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20181117052444/https://www.newspapers.com/clip/888394/formaldehyde_in_milk/">Archived</a> from the original on 2018-11-17<span class="reference-accessdate">. Retrieved <span class="nowrap">2014-08-20</span></span> – via Newspapers.com.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Topeka+Daily+Capital&rft.atitle=Wants+New+Law+Enacted.+Food+Inspector+Farnsworth+Would+Have+Use+of+Formaldehyde+in+Milk+Stopped&rft.pages=8&rft.date=1903-08-30&rft_id=https%3A%2F%2Fwww.newspapers.com%2Fclip%2F888394%2Fformaldehyde_in_milk%2F&rfr_id=info%3Asid%2Fen.wikipedia.org%3AFormaldehyde" class="Z3988"></span> <span style="position:relative; top: -2px;"><span typeof="mw:File"><a href="/wiki/Open_access" title="open access publication – free to read"><img alt="Open access icon" src="//upload.wikimedia.org/wikipedia/commons/thumb/7/77/Open_Access_logo_PLoS_transparent.svg/9px-Open_Access_logo_PLoS_transparent.svg.png" decoding="async" width="9" height="14" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/77/Open_Access_logo_PLoS_transparent.svg/14px-Open_Access_logo_PLoS_transparent.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/77/Open_Access_logo_PLoS_transparent.svg/18px-Open_Access_logo_PLoS_transparent.svg.png 2x" data-file-width="640" data-file-height="1000" /></a></span></span></span> </li> <li id="cite_note-121"><span class="mw-cite-backlink"><b><a href="#cite_ref-121">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation news cs1"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20110616192558/http://www.nationmultimedia.com/2011/06/16/national/Illegal-business-being-run-by-a-gang-30157928.html">"Illegal business 'being run by a gang'<span class="cs1-kern-right"></span>"</a>. <i>The Nation</i>. 2011-06-16. Archived from <a rel="nofollow" class="external text" href="http://www.nationmultimedia.com/2011/06/16/national/Illegal-business-being-run-by-a-gang-30157928.html">the original</a> on 2011-06-16.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Nation&rft.atitle=Illegal+business+%27being+run+by+a+gang%27&rft.date=2011-06-16&rft_id=http%3A%2F%2Fwww.nationmultimedia.com%2F2011%2F06%2F16%2Fnational%2FIllegal-business-being-run-by-a-gang-30157928.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AFormaldehyde" class="Z3988"></span></span> </li> <li id="cite_note-122"><span class="mw-cite-backlink"><b><a href="#cite_ref-122">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation news cs1"><a rel="nofollow" class="external text" href="https://www.thejakartapost.com/news/2012/02/23/import-formaldehyde-fish-pakistan-foiled-batam.html">"Import of formaldehyde fish from Pakistan foiled in Batam"</a>. <i>The Jakarta Post</i>. 2012-02-23. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20181216032155/https://www.thejakartapost.com/news/2012/02/23/import-formaldehyde-fish-pakistan-foiled-batam.html">Archived</a> from the original on 2018-12-16.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Jakarta+Post&rft.atitle=Import+of+formaldehyde+fish+from+Pakistan+foiled+in+Batam&rft.date=2012-02-23&rft_id=http%3A%2F%2Fwww.thejakartapost.com%2Fnews%2F2012%2F02%2F23%2Fimport-formaldehyde-fish-pakistan-foiled-batam.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AFormaldehyde" class="Z3988"></span></span> </li> <li id="cite_note-123"><span class="mw-cite-backlink"><b><a href="#cite_ref-123">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation news cs1"><a rel="nofollow" class="external text" href="https://www.thedailystar.net/news-detail-103948">"Trader Fined for Selling Fish Treated with Formalin"</a>. <i>The Daily Star</i>. 2009-08-31. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20190429100540/https://www.thedailystar.net/news-detail-103948">Archived</a> from the original on 2019-04-29.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Daily+Star&rft.atitle=Trader+Fined+for+Selling+Fish+Treated+with+Formalin&rft.date=2009-08-31&rft_id=https%3A%2F%2Fwww.thedailystar.net%2Fnews-detail-103948&rfr_id=info%3Asid%2Fen.wikipedia.org%3AFormaldehyde" class="Z3988"></span></span> </li> <li id="cite_note-124"><span class="mw-cite-backlink"><b><a href="#cite_ref-124">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation news cs1"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20180323012557/http://en.ntvbd.com/bangladesh/923/Formalin-Control-Bill-2015-passed">"Formalin Control Bill 2015 passed"</a>. <i>ntv online</i>. 2015-02-16. Archived from <a rel="nofollow" class="external text" href="http://en.ntvbd.com/bangladesh/923/Formalin-Control-Bill-2015-passed">the original</a> on 2018-03-23<span class="reference-accessdate">. Retrieved <span class="nowrap">2015-03-04</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=ntv+online&rft.atitle=Formalin+Control+Bill+2015+passed&rft.date=2015-02-16&rft_id=http%3A%2F%2Fen.ntvbd.com%2Fbangladesh%2F923%2FFormalin-Control-Bill-2015-passed&rfr_id=info%3Asid%2Fen.wikipedia.org%3AFormaldehyde" class="Z3988"></span></span> </li> <li id="cite_note-125"><span class="mw-cite-backlink"><b><a href="#cite_ref-125">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMeadows2006" class="citation journal cs1">Meadows, Michelle (January 2006). <a rel="nofollow" class="external text" href="https://www.fda.gov/media/110464/download">"A Century of Ensuring Safe Foods and Cosmetics"</a> <span class="cs1-format">(PDF)</span>. <i>FDA Consumer</i>. <b>40</b> (1): <span class="nowrap">6–</span>13. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/16528821">16528821</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=FDA+Consumer&rft.atitle=A+Century+of+Ensuring+Safe+Foods+and+Cosmetics&rft.volume=40&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E6-%3C%2Fspan%3E13&rft.date=2006-01&rft_id=info%3Apmid%2F16528821&rft.aulast=Meadows&rft.aufirst=Michelle&rft_id=https%3A%2F%2Fwww.fda.gov%2Fmedia%2F110464%2Fdownload&rfr_id=info%3Asid%2Fen.wikipedia.org%3AFormaldehyde" class="Z3988"></span></span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="Notes">Notes</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Formaldehyde&action=edit&section=30" title="Edit section: Notes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239543626"><div class="reflist"> <div class="mw-references-wrap"><ol class="references"> <li id="cite_note-carcinogen-16"><span class="mw-cite-backlink"><b><a href="#cite_ref-carcinogen_16-0">^</a></b></span> <span class="reference-text">Formaldehyde is classified as a carcinogen, according to the <a href="/wiki/United_States_Environmental_Protection_Agency" title="United States Environmental Protection Agency">Environmental Protection Agency</a>, <a href="/wiki/International_Agency_for_Research_on_Cancer" title="International Agency for Research on Cancer">International Agency for Research on Cancer (IARC)</a>, and U.S. National Toxicology Program.<sup id="cite_ref-cancer.gov_15-0" class="reference"><a href="#cite_note-cancer.gov-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup></span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Formaldehyde&action=edit&section=31" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1235681985">.mw-parser-output .side-box{margin:4px 0;box-sizing:border-box;border:1px solid #aaa;font-size:88%;line-height:1.25em;background-color:var(--background-color-interactive-subtle,#f8f9fa);display:flow-root}.mw-parser-output .side-box-abovebelow,.mw-parser-output .side-box-text{padding:0.25em 0.9em}.mw-parser-output .side-box-image{padding:2px 0 2px 0.9em;text-align:center}.mw-parser-output .side-box-imageright{padding:2px 0.9em 2px 0;text-align:center}@media(min-width:500px){.mw-parser-output .side-box-flex{display:flex;align-items:center}.mw-parser-output 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</div> <ul><li><a rel="nofollow" class="external text" href="https://www.ilo.org/dyn/icsc/showcard.display?p_lang=en&p_card_id=0275&p_version=2">International Chemical Safety Card 0275</a> (<i>gas</i>)</li> <li><a rel="nofollow" class="external text" href="https://www.ilo.org/dyn/icsc/showcard.display?p_lang=en&p_card_id=0695&p_version=2">International Chemical Safety Card 0695</a> (<i>solution</i>)</li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFNIOSH_Pocket_Guide_to_Chemical_Hazards" class="citation web cs1">NIOSH Pocket Guide to Chemical Hazards. <a rel="nofollow" class="external text" href="https://www.cdc.gov/niosh/npg/npgd0293.html">"#0293"</a>. <a href="/wiki/National_Institute_for_Occupational_Safety_and_Health" title="National Institute for Occupational Safety and Health">National Institute for Occupational Safety and Health</a> (NIOSH).</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=%230293&rft.pub=National+Institute+for+Occupational+Safety+and+Health+%28NIOSH%29&rft.au=NIOSH+Pocket+Guide+to+Chemical+Hazards&rft_id=https%3A%2F%2Fwww.cdc.gov%2Fniosh%2Fnpg%2Fnpgd0293.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AFormaldehyde" class="Z3988"></span></li> <li><a rel="nofollow" class="external text" href="http://www.npi.gov.au/database/substance-info/profiles/45.html">Entry for "Formaldehyde"</a> on the Australian <a href="/wiki/National_Pollutant_Inventory" title="National Pollutant Inventory">National Pollutant Inventory</a></li> <li><a rel="nofollow" class="external text" href="http://chemsub.online.fr/name/formaldehyde.html">Formaldehyde</a> from ChemSub Online</li> <li><a rel="nofollow" class="external text" href="https://www.irsst.qc.ca/media/documents/pubirsst/rg-473.pdf?i=0&redirected=1">Prevention guide—Formaldehyde in the Workplace (PDF)</a> from the IRSST</li> <li><a rel="nofollow" class="external text" href="https://www.cdc.gov/niosh/topics/formaldehyde/">Formaldehyde</a> from the <a href="/wiki/National_Institute_for_Occupational_Safety_and_Health" title="National Institute for Occupational Safety and Health">National Institute for Occupational Safety and Health</a></li> <li><a href="/wiki/International_Programme_on_Chemical_Safety" title="International Programme on Chemical Safety">IPCS</a> <a href="/wiki/IPCS_Health_and_Safety_Guide" title="IPCS Health and Safety Guide">Health and Safety Guide</a> <a rel="nofollow" class="external text" href="http://www.inchem.org/documents/hsg/hsg/hsg057.htm">57: Formaldehyde</a></li> <li><a href="/wiki/International_Programme_on_Chemical_Safety" title="International Programme on Chemical Safety">IPCS</a> <a href="/wiki/Environmental_Health_Criteria" class="mw-redirect" title="Environmental Health Criteria">Environmental Health Criteria</a> <a rel="nofollow" class="external text" href="http://www.inchem.org/documents/ehc/ehc/ehc89.htm">89: Formaldehyde</a></li> <li><a rel="nofollow" class="external text" href="http://www.inchem.org/documents/sids/sids/FORMALDEHYDE.pdf">SIDS Initial Assessment Report for Formaldehyde</a> from the <a href="/wiki/Organisation_for_Economic_Co-operation_and_Development" class="mw-redirect" title="Organisation for Economic Co-operation and Development">Organisation for Economic Co-operation and Development</a> (OECD)</li> <li><a rel="nofollow" class="external text" href="https://www.democracynow.org/2011/6/14/formaldehyde_added_to_known_carcinogens_list">"Formaldehyde Added to 'Known Carcinogens' List Despite Lobbying by Chemical Industry"</a>—video report by <i><a href="/wiki/Democracy_Now!" title="Democracy Now!">Democracy Now!</a></i></li> <li><a rel="nofollow" class="external text" href="http://assets.grist.org/article/people-are-still-living-in-femas-toxic-katrina-trailers-and-they-likely-have-no-idea/index.html">Do you own a 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Check your VIN#</a></li> <li><a rel="nofollow" class="external text" href="https://grist.org/article/what-do-i-do-if-i-am-living-in-a-fema-trailer/">So you're living in one of FEMA's Katrina trailers... 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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 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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> <li><a href="/wiki/Wine_fraud" title="Wine fraud">Wine</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 href="/wiki/Polycyclic_aromatic_hydrocarbon" title="Polycyclic aromatic hydrocarbon">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" class="mw-redirect" 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=1959_Moroccan_oil_poisoning_disaster&action=edit&redlink=1" class="new" title="1959 Moroccan oil poisoning disaster (page does not exist)">1959 Moroccan oil poisoning disaster</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_space800" 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_space800" 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/Imidogen" title="Imidogen">Imidogen</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/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_mononitride" title="Sulfur mononitride">Sulfur mononitride</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="/wiki/Iron(II)_cyanide" title="Iron(II) cyanide">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/Methylidynephosphane" title="Methylidynephosphane">Methylidynephosphane</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/Potassium_cyanide" title="Potassium cyanide">Potassium cyanide</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/Trihydrogen_cation" title="Trihydrogen cation">Trihydrogen cation</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/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="/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="/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/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/Thiocyanic_acid" title="Thiocyanic acid">Thiocyanic acid</a></li> <li><a href="/wiki/Thioformaldehyde" title="Thioformaldehyde">Thioformaldehyde</a></li> <li><a href="/wiki/Tricarbon_monosulfide" title="Tricarbon monosulfide">Tricarbon monosulfide</a></li> <li><a href="/wiki/Tricarbon_monoxide" title="Tricarbon monoxide">Tricarbon monoxide</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="/wiki/Cyclopropenone" title="Cyclopropenone">Cyclopropenone</a></li> <li><a href="/wiki/Diacetylene" title="Diacetylene">Diacetylene</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/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/Methyl_isocyanate" title="Methyl isocyanate">Methyl isocyanate</a></li> <li><a href="/wiki/Methylamine" title="Methylamine">Methylamine</a></li> <li><a href="/wiki/Propyne" title="Propyne">Propyne</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/Acrolein" title="Acrolein">Acrolein</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/Methyl_formate" title="Methyl formate">Methyl formate</a></li> <li><a href="/wiki/Polyyne" title="Polyyne">Methylcyanoacetylene</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/Ethanethiol" title="Ethanethiol">Ethanethiol</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/N-Methylformamide" title="N-Methylformamide">N-Methylformamide</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/Propionitrile" title="Propionitrile">Propionitrile</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/Butyronitrile" title="Butyronitrile">Butyronitrile</a></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/Ethyl_formate" title="Ethyl formate">Ethyl formate</a></li> <li><a href="/wiki/Ethylene_glycol" title="Ethylene glycol">Ethylene glycol</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> <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/Pyrimidine" title="Pyrimidine">Pyrimidine</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 class="mw-selflink selflink">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/Diazenylium" title="Diazenylium">N<sub>2</sub>D<sup>+</sup></a></li> <li><a href="/wiki/Propyne" title="Propyne">Propyne</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/Glycine" title="Glycine">Glycine</a></li> <li><a href="/wiki/Graphene" title="Graphene">Graphene</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/Hemolithin" title="Hemolithin">Hemolithin</a></li> <li><a href="/wiki/Carbon" title="Carbon">Linear C<sub>5</sub></a></li> <li><a href="/wiki/Methoxyethane" title="Methoxyethane">Methoxyethane</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/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/Photodissociation_region" title="Photodissociation region">Photodissociation region</a></li> <li><a href="/wiki/Polycyclic_aromatic_hydrocarbon" title="Polycyclic aromatic hydrocarbon">Polycyclic aromatic hydrocarbon</a> (PAH)</li> <li><a href="/wiki/Pseudo-panspermia" title="Pseudo-panspermia">Pseudo-panspermia</a></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" 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src="//upload.wikimedia.org/wikipedia/commons/thumb/e/ed/Papapishu-Lab-icon-6.svg/16px-Papapishu-Lab-icon-6.svg.png" decoding="async" width="16" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/ed/Papapishu-Lab-icon-6.svg/24px-Papapishu-Lab-icon-6.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/ed/Papapishu-Lab-icon-6.svg/32px-Papapishu-Lab-icon-6.svg.png 2x" data-file-width="512" data-file-height="512" /></span></span> </span><a href="/wiki/Portal:Chemistry" title="Portal:Chemistry">Chemistry portal</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="TRP_channel_modulators711" style="padding:3px"><table class="nowraplinks mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Transient_receptor_potential_channel_modulators" title="Template:Transient receptor potential channel modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Transient_receptor_potential_channel_modulators" title="Template talk:Transient receptor potential channel modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Transient_receptor_potential_channel_modulators" title="Special:EditPage/Template:Transient receptor potential channel modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="TRP_channel_modulators711" style="font-size:114%;margin:0 4em"><a href="/wiki/Transient_receptor_potential_channel" title="Transient receptor potential channel"><abbr title="Transient receptor potential">TRP</abbr> channel</a> <a href="/wiki/Channel_modulator" title="Channel modulator">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><abbr title="Transient receptor potential ankyrin channel"><a href="/wiki/TRPA_(ion_channel)" title="TRPA (ion channel)">TRPA</a></abbr></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Activators</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/4-Hydroxynonenal" title="4-Hydroxynonenal">4-Hydroxynonenal</a></li> <li><a href="/wiki/4-Oxo-2-nonenal" title="4-Oxo-2-nonenal">4-Oxo-2-nonenal</a></li> <li><a href="/wiki/Epoxyeicosatrienoic_acid" title="Epoxyeicosatrienoic acid">5,6-EET</a></li> <li><a href="/wiki/12-Hydroxyeicosatetraenoic_acid" title="12-Hydroxyeicosatetraenoic acid">12S-HpETE</a></li> <li><a href="/wiki/Cyclopentenone_prostaglandins" title="Cyclopentenone prostaglandins">15-Deoxy-Δ<sup>12,14</sup>-prostaglandin J2</a></li> <li><a href="/wiki/Hydroxy-%CE%B1-sanshool" title="Hydroxy-α-sanshool">α-Sanshool</a> (<a href="/wiki/Ginger" title="Ginger">ginger</a>, <a href="/wiki/Sichuan_pepper" title="Sichuan pepper">Sichuan</a> and <a href="/wiki/Grains_of_paradise" title="Grains of paradise">melegueta peppers</a>)</li> <li><a href="/wiki/Acrolein" title="Acrolein">Acrolein</a></li> <li><a href="/wiki/Allicin" title="Allicin">Allicin</a> (<a href="/wiki/Garlic" title="Garlic">garlic</a>)</li> <li><a href="/wiki/Allyl_isothiocyanate" title="Allyl isothiocyanate">Allyl isothiocyanate</a> (<a href="/wiki/Mustard_plant" title="Mustard plant">mustard</a>, <a href="/wiki/Radish" title="Radish">radish</a>, <a href="/wiki/Horseradish" title="Horseradish">horseradish</a>, <a href="/wiki/Wasabi" title="Wasabi">wasabi</a>)</li> <li><a href="/wiki/AM404" title="AM404">AM404</a></li> <li><a href="/wiki/ASP-7663" title="ASP-7663">ASP-7663</a></li> <li><a href="/wiki/Bradykinin" title="Bradykinin">Bradykinin</a></li> <li><a href="/wiki/Cannabichromene" title="Cannabichromene">Cannabichromene</a> (<a href="/wiki/Cannabis" title="Cannabis">cannabis</a>)</li> <li><a href="/wiki/Cannabidiol" title="Cannabidiol">Cannabidiol</a> (<a href="/wiki/Cannabis" title="Cannabis">cannabis</a>)</li> <li><a href="/wiki/Cannabigerol" title="Cannabigerol">Cannabigerol</a> (<a href="/wiki/Cannabis" title="Cannabis">cannabis</a>)</li> <li><a href="/wiki/Cinnamaldehyde" title="Cinnamaldehyde">Cinnamaldehyde</a> (<a href="/wiki/Cinnamon" title="Cinnamon">cinnamon</a>)</li> <li><a href="/wiki/CR_gas" title="CR gas">CR gas (dibenzoxazepine; DBO)</a></li> <li><a href="/wiki/CS_gas" title="CS gas">CS gas (2-chlorobenzal malononitrile)</a></li> <li><a href="/wiki/Cuminaldehyde" title="Cuminaldehyde">Cuminaldehyde</a> (<a href="/wiki/Cumin" title="Cumin">cumin</a>)</li> <li><a href="/wiki/Curcumin" title="Curcumin">Curcumin</a> (<a href="/wiki/Turmeric" title="Turmeric">turmeric</a>)</li> <li><a href="/w/index.php?title=Dehydroligustilide&action=edit&redlink=1" class="new" title="Dehydroligustilide (page does not exist)">Dehydroligustilide</a> (<a href="/wiki/Celery" title="Celery">celery</a>)</li> <li><a href="/wiki/Diallyl_disulfide" title="Diallyl disulfide">Diallyl disulfide</a></li> <li><a href="/wiki/Dicentrine" title="Dicentrine">Dicentrine</a> (<i><a href="/wiki/Lindera" title="Lindera">Lindera</a></i> spp.)</li> <li><a href="/w/index.php?title=Farnesyl_thiosalicylic_acid&action=edit&redlink=1" class="new" title="Farnesyl thiosalicylic acid (page does not exist)">Farnesyl thiosalicylic acid</a></li> <li><a href="/wiki/Formalin" class="mw-redirect" title="Formalin">Formalin</a></li> <li><a href="/wiki/Gingerol" title="Gingerol">Gingerols</a> (<a href="/wiki/Ginger" title="Ginger">ginger</a>)</li> <li><a href="/wiki/Hepoxilin_A3" class="mw-redirect" title="Hepoxilin A3">Hepoxilin A3</a></li> <li><a href="/wiki/Hepoxilin_B3" class="mw-redirect" title="Hepoxilin B3">Hepoxilin B3</a></li> <li><a href="/wiki/Hydrogen_peroxide" title="Hydrogen peroxide">Hydrogen peroxide</a></li> <li><a href="/wiki/Icilin" title="Icilin">Icilin</a></li> <li><a href="/wiki/Isothiocyanate" title="Isothiocyanate">Isothiocyanate</a></li> <li><a href="/wiki/JT-010" title="JT-010">JT-010</a></li> <li><a href="/wiki/Ligustilide" title="Ligustilide">Ligustilide</a> (<a href="/wiki/Celery" title="Celery">celery</a>, <i><a href="/wiki/Angelica_acutiloba" title="Angelica acutiloba">Angelica acutiloba</a></i>)</li> <li><a href="/wiki/Linalool" title="Linalool">Linalool</a> (<a href="/wiki/Sichuan_pepper" title="Sichuan pepper">Sichuan pepper</a>, <a href="/wiki/Thyme" title="Thyme">thyme</a>)</li> <li><a href="/wiki/Methylglyoxal" title="Methylglyoxal">Methylglyoxal</a></li> <li><a href="/wiki/Methyl_salicylate" title="Methyl salicylate">Methyl salicylate</a> (<a href="/wiki/Wintergreen" title="Wintergreen">wintergreen</a>)</li> <li><a href="/wiki/N-Methylmaleimide" title="N-Methylmaleimide">N-Methylmaleimide</a></li> <li><a href="/wiki/Nicotine" title="Nicotine">Nicotine</a> (<a href="/wiki/Tobacco" title="Tobacco">tobacco</a>)</li> <li><a href="/wiki/Oleocanthal" title="Oleocanthal">Oleocanthal</a> (<a href="/wiki/Olive_oil" title="Olive oil">olive oil</a>)</li> <li><a href="/wiki/Paclitaxel" title="Paclitaxel">Paclitaxel</a> (<a href="/wiki/Taxus_brevifolia" title="Taxus brevifolia">Pacific yew</a>)</li> <li><a href="/wiki/Paracetamol" title="Paracetamol">Paracetamol (acetaminophen)</a></li> <li><a href="/wiki/PF-4840154" title="PF-4840154">PF-4840154</a></li> <li><a href="/wiki/Phenacyl_chloride" title="Phenacyl chloride">Phenacyl chloride</a></li> <li><a href="/wiki/Polygodial" title="Polygodial">Polygodial</a> (<a href="/wiki/Tasmannia_stipitata" title="Tasmannia stipitata">Dorrigo pepper</a>)</li> <li><a href="/wiki/Shogaol" title="Shogaol">Shogaols</a> (<a href="/wiki/Ginger" title="Ginger">ginger</a>, <a href="/wiki/Sichuan_pepper" title="Sichuan pepper">Sichuan</a> and <a href="/wiki/Grains_of_paradise" title="Grains of paradise">melegueta peppers</a>)</li> <li><a href="/wiki/Tear_gas" title="Tear gas">Tear gases</a></li> <li><a href="/wiki/Tetrahydrocannabinol" title="Tetrahydrocannabinol">Tetrahydrocannabinol</a> (<a href="/wiki/Cannabis" title="Cannabis">cannabis</a>)</li> <li><a href="/wiki/Tetrahydrocannabiorcol" title="Tetrahydrocannabiorcol">Tetrahydrocannabiorcol</a></li> <li><a href="/wiki/Syn-Propanethial-S-oxide" title="Syn-Propanethial-S-oxide">Thiopropanal S-oxide</a> (<a href="/wiki/Onion" title="Onion">onion</a>)</li> <li><a href="/wiki/Umbellulone" title="Umbellulone">Umbellulone</a> (<i>Umbellularia californica</i>)</li> <li><a href="/wiki/WIN_55,212-2" title="WIN 55,212-2">WIN 55,212-2</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Blockers</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/A-967079" title="A-967079">A-967079</a></li> <li><a href="/wiki/AM-0902" title="AM-0902">AM-0902</a></li> <li><a href="/w/index.php?title=Dehydroligustilide&action=edit&redlink=1" class="new" title="Dehydroligustilide (page does not exist)">Dehydroligustilide</a> (<a href="/wiki/Celery" title="Celery">celery</a>)</li> <li><a href="/wiki/HC-030031" title="HC-030031">HC-030031</a></li> <li><a href="/wiki/Nicotine" title="Nicotine">Nicotine</a> (<a href="/wiki/Tobacco" title="Tobacco">tobacco</a>)</li> <li><a href="/wiki/PF-04745637" title="PF-04745637">PF-04745637</a></li> <li><a href="/wiki/Ruthenium_red" title="Ruthenium red">Ruthenium red</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><abbr title="Transient receptor potential canonical channel"><a href="/wiki/TRPC" title="TRPC">TRPC</a></abbr></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Activators</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/Adhyperforin" title="Adhyperforin">Adhyperforin</a> (<a href="/wiki/Hypericum_perforatum" title="Hypericum perforatum">St John's wort</a>)</li> <li><a href="/wiki/Diglyceride" title="Diglyceride">Diacyl glycerol</a></li> <li><a href="/wiki/GSK1702934A" title="GSK1702934A">GSK1702934A</a></li> <li><a href="/wiki/Hyperforin" title="Hyperforin">Hyperforin</a> (<a href="/wiki/Hypericum_perforatum" title="Hypericum perforatum">St John's wort</a>)</li> <li><a href="/wiki/Substance_P" title="Substance P">Substance P</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Blockers</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=3%E2%80%B2-5-Dichlorodiphenylamine-2-carboxylic_acid&action=edit&redlink=1" class="new" title="3′-5-Dichlorodiphenylamine-2-carboxylic acid (page does not exist)">DCDPC</a></li> <li><a href="/wiki/Dehydroepiandrosterone_sulfate" title="Dehydroepiandrosterone sulfate">DHEA-S</a></li> <li><a href="/wiki/Flufenamic_acid" title="Flufenamic acid">Flufenamic acid</a></li> <li><a href="/wiki/GSK417651A" title="GSK417651A">GSK417651A</a></li> <li><a href="/w/index.php?title=GSK2293017A&action=edit&redlink=1" class="new" title="GSK2293017A (page does not exist)">GSK2293017A</a></li> <li><a href="/wiki/Meclofenamic_acid" title="Meclofenamic acid">Meclofenamic acid</a></li> <li><a href="/wiki/N-(p-Amylcinnamoyl)anthranilic_acid" title="N-(p-Amylcinnamoyl)anthranilic acid">N-(p-Amylcinnamoyl)anthranilic acid</a></li> <li><a href="/wiki/Niflumic_acid" title="Niflumic acid">Niflumic acid</a></li> <li><a href="/wiki/Pregnenolone_sulfate" title="Pregnenolone sulfate">Pregnenolone sulfate</a></li> <li><a href="/wiki/Progesterone" title="Progesterone">Progesterone</a></li> <li><a href="/w/index.php?title=Pyr3&action=edit&redlink=1" class="new" title="Pyr3 (page does not exist)">Pyr3</a></li> <li><a href="/wiki/Tolfenamic_acid" title="Tolfenamic acid">Tolfenamic acid</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><abbr title="Transient receptor potential melastatin channel"><a href="/wiki/TRPM" title="TRPM">TRPM</a></abbr></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Activators</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/Adenosine_diphosphate_ribose" title="Adenosine diphosphate ribose">ADP-ribose</a></li> <li><a href="/w/index.php?title=BCTC_(drug)&action=edit&redlink=1" class="new" title="BCTC (drug) (page does not exist)">BCTC</a></li> <li><a href="/wiki/Calcium" title="Calcium">Calcium</a> (intracellular)</li> <li><a href="/wiki/CIM-0216" title="CIM-0216">CIM-0216</a></li> <li><a href="/wiki/Cold" title="Cold">Cold</a></li> <li><a href="/w/index.php?title=Coolact_P&action=edit&redlink=1" class="new" title="Coolact P (page does not exist)">Coolact P</a></li> <li><a href="/wiki/Cooling_Agent_10" class="mw-redirect" title="Cooling Agent 10">Cooling Agent 10</a></li> <li><a href="/wiki/Eucalyptol" title="Eucalyptol">Eucalyptol</a> (<a href="/wiki/Eucalyptus" title="Eucalyptus">eucalyptus</a>)</li> <li><a href="/w/index.php?title=Frescolat_MGA&action=edit&redlink=1" class="new" title="Frescolat MGA (page does not exist)">Frescolat MGA</a></li> <li><a href="/w/index.php?title=Frescolat_ML&action=edit&redlink=1" class="new" title="Frescolat ML (page does not exist)">Frescolat ML</a></li> <li><a href="/wiki/Geraniol" title="Geraniol">Geraniol</a></li> <li><a href="/wiki/Hydroxycitronellal" title="Hydroxycitronellal">Hydroxycitronellal</a></li> <li><a href="/wiki/Icilin" title="Icilin">Icilin</a></li> <li><a href="/wiki/Linalool" title="Linalool">Linalool</a></li> <li><a href="/wiki/Menthol" title="Menthol">Menthol</a> (<a href="/wiki/Mentha" title="Mentha">mint</a>)</li> <li><a href="/w/index.php?title=PMD_38&action=edit&redlink=1" class="new" title="PMD 38 (page does not exist)">PMD 38</a></li> <li><a href="/wiki/Pregnenolone_sulfate" title="Pregnenolone sulfate">Pregnenolone sulfate</a></li> <li><a href="/w/index.php?title=Rutamarin&action=edit&redlink=1" class="new" title="Rutamarin (page does not exist)">Rutamarin</a> (<i><a href="/wiki/Ruta_graveolens" title="Ruta graveolens">Ruta graveolens</a></i>)</li> <li><a href="/wiki/Steviol_glycoside" title="Steviol glycoside">Steviol glycosides</a> (e.g., <a href="/wiki/Stevioside" title="Stevioside">stevioside</a>) (<i><a href="/wiki/Stevia_rebaudiana" title="Stevia rebaudiana">Stevia rebaudiana</a></i>)</li> <li>Sweet <a href="/wiki/Taste" title="Taste">tastants</a> (e.g., <a href="/wiki/Glucose" title="Glucose">glucose</a>, <a href="/wiki/Fructose" title="Fructose">fructose</a>, <a href="/wiki/Sucrose" title="Sucrose">sucrose</a>; indirectly)</li> <li><a href="/w/index.php?title=Thio-BCTC&action=edit&redlink=1" class="new" title="Thio-BCTC (page does not exist)">Thio-BCTC</a></li> <li><a href="/wiki/WS-12" class="mw-redirect" title="WS-12">WS-12</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Blockers</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/AMG-333" title="AMG-333">AMG-333</a></li> <li><a href="/wiki/Capsazepine" title="Capsazepine">Capsazepine</a></li> <li><a href="/wiki/Clotrimazole" title="Clotrimazole">Clotrimazole</a></li> <li><a href="/w/index.php?title=3%E2%80%B2-5-Dichlorodiphenylamine-2-carboxylic_acid&action=edit&redlink=1" class="new" title="3′-5-Dichlorodiphenylamine-2-carboxylic acid (page does not exist)">DCDPC</a></li> <li><a href="/w/index.php?title=Elismetrep&action=edit&redlink=1" class="new" title="Elismetrep (page does not exist)">Elismetrep</a></li> <li><a href="/wiki/Flufenamic_acid" title="Flufenamic acid">Flufenamic acid</a></li> <li><a href="/wiki/Meclofenamic_acid" title="Meclofenamic acid">Meclofenamic acid</a></li> <li><a href="/wiki/Mefenamic_acid" title="Mefenamic acid">Mefenamic acid</a></li> <li><a href="/wiki/N-(p-Amylcinnamoyl)anthranilic_acid" title="N-(p-Amylcinnamoyl)anthranilic acid">N-(p-Amylcinnamoyl)anthranilic acid</a></li> <li><a href="/wiki/Nicotine" title="Nicotine">Nicotine</a> (<a href="/wiki/Tobacco" title="Tobacco">tobacco</a>)</li> <li><a href="/wiki/Niflumic_acid" title="Niflumic acid">Niflumic acid</a></li> <li><a href="/wiki/Ononetin" title="Ononetin">Ononetin</a></li> <li><a href="/wiki/PF-05105679" title="PF-05105679">PF-05105679</a></li> <li><a href="/wiki/RQ-00203078" title="RQ-00203078">RQ-00203078</a></li> <li><a href="/wiki/Ruthenium_red" title="Ruthenium red">Ruthenium red</a></li> <li><a href="/w/index.php?title=Rutamarin&action=edit&redlink=1" class="new" title="Rutamarin (page does not exist)">Rutamarin</a> (<i><a href="/wiki/Ruta_graveolens" title="Ruta graveolens">Ruta graveolens</a></i>)</li> <li><a href="/wiki/Tolfenamic_acid" title="Tolfenamic acid">Tolfenamic acid</a></li> <li><a href="/wiki/Triphenylphosphine_oxide" title="Triphenylphosphine oxide">TPPO</a></li> <li><a href="/wiki/TRPM4-IN-5" title="TRPM4-IN-5">TRPM4-IN-5</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><abbr title="Transient receptor potential mucolipin channel"><a href="/wiki/TRPML" title="TRPML">TRPML</a></abbr></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Activators</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="/w/index.php?title=EVP21&action=edit&redlink=1" class="new" title="EVP21 (page does not exist)">EVP21</a></li> <li><a href="/wiki/MK6-83" title="MK6-83">MK6-83</a></li> <li><a href="/wiki/ML-SA1" title="ML-SA1">ML-SA1</a></li> <li><a href="/wiki/ML2-SA1" title="ML2-SA1">ML2-SA1</a></li> <li><a href="/wiki/Phosphatidylinositol_3,5-bisphosphate" title="Phosphatidylinositol 3,5-bisphosphate">PI(3,5)P<sub>2</sub></a></li> <li><a href="/w/index.php?title=SF-22&action=edit&redlink=1" class="new" title="SF-22 (page does not exist)">SF-22</a></li> <li><a href="/wiki/SN-2" title="SN-2">SN-2</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Blockers</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/ML-SI3" title="ML-SI3">ML-SI3</a></li> <li><a href="/wiki/Phosphatidylinositol_4,5-bisphosphate" title="Phosphatidylinositol 4,5-bisphosphate">PI(4,5)P<sub>2</sub></a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><abbr title="Transient receptor potential polycystin channel"><a href="/wiki/TRPP" title="TRPP">TRPP</a></abbr></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Activators</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/Triptolide" title="Triptolide">Triptolide</a> (<i><a href="/wiki/Tripterygium_wilfordii" title="Tripterygium wilfordii">Tripterygium wilfordii</a></i>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Blockers</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/Ruthenium_red" title="Ruthenium red">Ruthenium red</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><abbr title="Transient receptor potential vanilloid channel"><a href="/wiki/TRPV" title="TRPV">TRPV</a></abbr></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Activators</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/2-Aminoethoxydiphenyl_borate" title="2-Aminoethoxydiphenyl borate">2-APB</a></li> <li><a href="/wiki/Epoxyeicosatrienoic_acid" title="Epoxyeicosatrienoic acid">5,6-EET</a></li> <li><a href="/wiki/9-Hydroxyoctadecadienoic_acid" title="9-Hydroxyoctadecadienoic acid">9-HODE</a></li> <li><a href="/wiki/9-Hydroxyoctadecadienoic_acid" title="9-Hydroxyoctadecadienoic acid">9-oxoODE</a></li> <li><a href="/wiki/12-Hydroxyeicosatetraenoic_acid" title="12-Hydroxyeicosatetraenoic acid">12S-HETE</a></li> <li><a href="/wiki/12-Hydroxyeicosatetraenoic_acid" title="12-Hydroxyeicosatetraenoic acid">12S-HpETE</a></li> <li><a href="/wiki/13-Hydroxyoctadecadienoic_acid" title="13-Hydroxyoctadecadienoic acid">13-HODE</a></li> <li><a href="/wiki/13-Hydroxyoctadecadienoic_acid" title="13-Hydroxyoctadecadienoic acid">13-oxoODE</a></li> <li><a href="/wiki/20-Hydroxyeicosatetraenoic_acid" title="20-Hydroxyeicosatetraenoic acid">20-HETE</a></li> <li><a href="/wiki/Hydroxy-%CE%B1-sanshool" title="Hydroxy-α-sanshool">α-Sanshool</a> (<a href="/wiki/Ginger" title="Ginger">ginger</a>, <a href="/wiki/Sichuan_pepper" title="Sichuan pepper">Sichuan</a> and <a href="/wiki/Grains_of_paradise" title="Grains of paradise">melegueta peppers</a>)</li> <li><a href="/wiki/Allicin" title="Allicin">Allicin</a> (<a href="/wiki/Garlic" title="Garlic">garlic</a>)</li> <li><a href="/wiki/AM404" title="AM404">AM404</a></li> <li><a href="/wiki/Anandamide" title="Anandamide">Anandamide</a></li> <li><a href="/w/index.php?title=Bisandrographolide&action=edit&redlink=1" class="new" title="Bisandrographolide (page does not exist)">Bisandrographolide</a> (<i><a href="/wiki/Andrographis_paniculata" title="Andrographis paniculata">Andrographis paniculata</a></i>)</li> <li><a href="/wiki/Camphor" title="Camphor">Camphor</a> (<a href="/wiki/Cinnamomum_camphora" class="mw-redirect" title="Cinnamomum camphora">camphor laurel</a>, <a href="/wiki/Rosemary" title="Rosemary">rosemary</a>, <a href="/wiki/Camphorweed" title="Camphorweed">camphorweed</a>, <a href="/wiki/African_blue_basil" title="African blue basil">African blue basil</a>, <a href="/wiki/Ocimum_kilimandscharicum" title="Ocimum kilimandscharicum">camphor basil</a>)</li> <li><a href="/wiki/Cannabidiol" title="Cannabidiol">Cannabidiol</a> (<a href="/wiki/Cannabis" title="Cannabis">cannabis</a>)</li> <li><a href="/wiki/Cannabidivarin" title="Cannabidivarin">Cannabidivarin</a> (<a href="/wiki/Cannabis" title="Cannabis">cannabis</a>)</li> <li><a href="/wiki/Capsaicin" title="Capsaicin">Capsaicin</a> (<a href="/wiki/Chili_pepper" title="Chili pepper">chili pepper</a>)</li> <li><a href="/wiki/Carvacrol" title="Carvacrol">Carvacrol</a> (<a href="/wiki/Oregano" title="Oregano">oregano</a>, <a href="/wiki/Thyme" title="Thyme">thyme</a>, <a href="/wiki/Lepidium" title="Lepidium">pepperwort</a>, <a href="/wiki/Monarda_fistulosa" title="Monarda fistulosa">wild bergamot</a>, others)</li> <li><a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone">DHEA</a></li> <li><a href="/wiki/Diglyceride" title="Diglyceride">Diacyl glycerol</a></li> <li><a href="/wiki/Dihydrocapsaicin" title="Dihydrocapsaicin">Dihydrocapsaicin</a> (<a href="/wiki/Chili_pepper" title="Chili pepper">chili pepper</a>)</li> <li><a href="/wiki/Estradiol" title="Estradiol">Estradiol</a></li> <li><a href="/wiki/Eugenol" title="Eugenol">Eugenol</a> (<a href="/wiki/Basil" title="Basil">basil</a>, <a href="/wiki/Clove" title="Clove">clove</a>)</li> <li><a href="/wiki/Evodiamine" title="Evodiamine">Evodiamine</a> (<i><a href="/wiki/Tetradium_ruticarpum" title="Tetradium ruticarpum">Euodia ruticarpa</a></i>)</li> <li><a href="/wiki/Gingerol" title="Gingerol">Gingerols</a> (<a href="/wiki/Ginger" title="Ginger">ginger</a>)</li> <li><a href="/wiki/GSK1016790A" title="GSK1016790A">GSK1016790A</a></li> <li><a href="/wiki/Heat" title="Heat">Heat</a></li> <li><a href="/wiki/Hepoxilin_A3" class="mw-redirect" title="Hepoxilin A3">Hepoxilin A3</a></li> <li><a href="/wiki/Hepoxilin_B3" class="mw-redirect" title="Hepoxilin B3">Hepoxilin B3</a></li> <li><a href="/wiki/Homocapsaicin" title="Homocapsaicin">Homocapsaicin</a> (<a href="/wiki/Chili_pepper" title="Chili pepper">chili pepper</a>)</li> <li><a href="/wiki/Homodihydrocapsaicin" title="Homodihydrocapsaicin">Homodihydrocapsaicin</a> (<a href="/wiki/Chili_pepper" title="Chili pepper">chili pepper</a>)</li> <li><a href="/wiki/Incensole" title="Incensole">Incensole</a> (<a href="/wiki/Incense" title="Incense">incense</a>)</li> <li><a href="/wiki/Lysophosphatidic_acid" title="Lysophosphatidic acid">Lysophosphatidic acid</a></li> <li>Low <a href="/wiki/PH" title="PH">pH</a> (acidic conditions)</li> <li><a href="/wiki/Menthol" title="Menthol">Menthol</a> (<a href="/wiki/Mentha" title="Mentha">mint</a>)</li> <li><a href="/wiki/N-Arachidonoyl_dopamine" title="N-Arachidonoyl dopamine">N-Arachidonoyl dopamine</a></li> <li><a href="/w/index.php?title=N-Oleoyldopamine&action=edit&redlink=1" class="new" title="N-Oleoyldopamine (page does not exist)">N-Oleoyldopamine</a></li> <li><a href="/wiki/Oleoylethanolamide" title="Oleoylethanolamide">N-Oleoylethanolamide</a></li> <li><a href="/wiki/Nonivamide" title="Nonivamide">Nonivamide (PAVA)</a> (<a href="/wiki/PAVA_spray" title="PAVA spray">PAVA spray</a>)</li> <li><a href="/wiki/Nordihydrocapsaicin" title="Nordihydrocapsaicin">Nordihydrocapsaicin</a> (<a href="/wiki/Chili_pepper" title="Chili pepper">chili pepper</a>)</li> <li><a href="/wiki/Paclitaxel" title="Paclitaxel">Paclitaxel</a> (<a href="/wiki/Taxus_brevifolia" title="Taxus brevifolia">Pacific yew</a>)</li> <li><a href="/wiki/Paracetamol" title="Paracetamol">Paracetamol (acetaminophen)</a></li> <li><a href="/wiki/Phenylacetylrinvanil" title="Phenylacetylrinvanil">Phenylacetylrinvanil</a></li> <li><a href="/wiki/Phorbol_esters" title="Phorbol esters">Phorbol esters</a> (e.g., <a href="/w/index.php?title=4%CE%B1-phorbol_12,13-didecanoate&action=edit&redlink=1" class="new" title="4α-phorbol 12,13-didecanoate (page does not exist)">4α-PDD</a>)</li> <li><a href="/wiki/Piperine" title="Piperine">Piperine</a> (<a href="/wiki/Black_pepper" title="Black pepper">black pepper</a>, <a href="/wiki/Long_pepper" title="Long pepper">long pepper</a>)</li> <li><a href="/wiki/Polygodial" title="Polygodial">Polygodial</a> (<a href="/wiki/Tasmannia_stipitata" title="Tasmannia stipitata">Dorrigo pepper</a>)</li> <li><a href="/wiki/Probenecid" title="Probenecid">Probenecid</a></li> <li><a href="/wiki/Proton" title="Proton">Protons</a></li> <li><a href="/wiki/RhTx" title="RhTx">RhTx</a></li> <li><a href="/w/index.php?title=Rutamarin&action=edit&redlink=1" class="new" title="Rutamarin (page does not exist)">Rutamarin</a> (<i><a href="/wiki/Ruta_graveolens" title="Ruta graveolens">Ruta graveolens</a></i>)</li> <li><a href="/wiki/Resiniferatoxin" title="Resiniferatoxin">Resiniferatoxin</a> (RTX) (<i><a href="/wiki/Euphorbia_resinifera" title="Euphorbia resinifera">Euphorbia resinifera</a>/<a href="/wiki/Euphorbia_poissonii" title="Euphorbia poissonii">pooissonii</a></i>)</li> <li><a href="/wiki/Shogaol" title="Shogaol">Shogaols</a> (<a href="/wiki/Ginger" title="Ginger">ginger</a>, <a href="/wiki/Sichuan_pepper" title="Sichuan pepper">Sichuan</a> and <a href="/wiki/Grains_of_paradise" title="Grains of paradise">melegueta peppers</a>)</li> <li><a href="/wiki/Tetrahydrocannabivarin" title="Tetrahydrocannabivarin">Tetrahydrocannabivarin</a> (<a href="/wiki/Cannabis" title="Cannabis">cannabis</a>)</li> <li><a href="/wiki/Thymol" title="Thymol">Thymol</a> (<a href="/wiki/Thyme" title="Thyme">thyme</a>, <a href="/wiki/Oregano" title="Oregano">oregano</a>)</li> <li><a href="/wiki/Tinyatoxin" title="Tinyatoxin">Tinyatoxin</a> (<i><a href="/wiki/Euphorbia_resinifera" title="Euphorbia resinifera">Euphorbia resinifera</a>/<a href="/wiki/Euphorbia_poissonii" title="Euphorbia poissonii">pooissonii</a></i>)</li> <li><a href="/wiki/Tramadol" title="Tramadol">Tramadol</a></li> <li><a href="/wiki/Vanillin" title="Vanillin">Vanillin</a> (<a href="/wiki/Vanilla" title="Vanilla">vanilla</a>)</li> <li><a href="/wiki/Zucapsaicin" title="Zucapsaicin">Zucapsaicin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Blockers</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/Spinasterol" title="Spinasterol">α-Spinasterol</a> (<i><a href="/wiki/Vernonia" title="Vernonia">Vernonia tweediana</a></i>)</li> <li><a href="/wiki/AMG-517" title="AMG-517">AMG-517</a></li> <li><a href="/wiki/AMG-9810" title="AMG-9810">AMG-9810</a></li> <li><a href="/w/index.php?title=Asivatrep&action=edit&redlink=1" class="new" title="Asivatrep (page does not exist)">Asivatrep</a></li> <li><a href="/w/index.php?title=BCTC_(drug)&action=edit&redlink=1" class="new" title="BCTC (drug) (page does not exist)">BCTC</a></li> <li><a href="/wiki/Cannabigerol" title="Cannabigerol">Cannabigerol</a> (<a href="/wiki/Cannabis" title="Cannabis">cannabis</a>)</li> <li><a href="/wiki/Cannabigerolic_acid" title="Cannabigerolic acid">Cannabigerolic acid</a> (<a href="/wiki/Cannabis" title="Cannabis">cannabis</a>)</li> <li><a href="/wiki/Cannabigerovarin" title="Cannabigerovarin">Cannabigerovarin</a> (<a href="/wiki/Cannabis" title="Cannabis">cannabis</a>)</li> <li><a href="/wiki/Cannabinol" title="Cannabinol">Cannabinol</a> (<a href="/wiki/Cannabis" title="Cannabis">cannabis</a>)</li> <li><a href="/wiki/Capsazepine" title="Capsazepine">Capsazepine</a></li> <li><a href="/w/index.php?title=3%E2%80%B2-5-Dichlorodiphenylamine-2-carboxylic_acid&action=edit&redlink=1" class="new" title="3′-5-Dichlorodiphenylamine-2-carboxylic acid (page does not exist)">DCDPC</a></li> <li><a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone">DHEA</a></li> <li><a href="/wiki/Dehydroepiandrosterone_sulfate" title="Dehydroepiandrosterone sulfate">DHEA-S</a></li> <li><a href="/wiki/Flufenamic_acid" title="Flufenamic acid">Flufenamic acid</a></li> <li><a href="/wiki/GRC-6211" title="GRC-6211">GRC-6211</a></li> <li><a href="/wiki/HC-067047" title="HC-067047">HC-067047</a></li> <li><a href="/wiki/Lanthanum" title="Lanthanum">Lanthanum</a></li> <li><a href="/wiki/Mavatrep" title="Mavatrep">Mavatrep</a></li> <li><a href="/wiki/Meclofenamic_acid" title="Meclofenamic acid">Meclofenamic acid</a></li> <li><a href="/wiki/N-(p-Amylcinnamoyl)anthranilic_acid" title="N-(p-Amylcinnamoyl)anthranilic acid">N-(p-Amylcinnamoyl)anthranilic acid</a></li> <li><a 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title="TRPV3-74a">TRPV3-74a</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div><i><b>See also:</b> <a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a> • <a href="/wiki/Template:Ion_channel_modulators" title="Template:Ion channel modulators">Ion channel modulators</a></i></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"><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"></div><div role="navigation" class="navbox authority-control" 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