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data-event-name="pinnable-header.vector-toc.pin">move to sidebar</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-toc.unpin">hide</button> </div> <ul class="vector-toc-contents" id="mw-panel-toc-list"> <li id="toc-mw-content-text" class="vector-toc-list-item vector-toc-level-1"> <a href="#" class="vector-toc-link"> <div class="vector-toc-text">(Top)</div> </a> </li> <li id="toc-Nomenclature" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Nomenclature"> <div class="vector-toc-text"> <span class="vector-toc-numb">1</span> <span>Nomenclature</span> </div> </a> <button aria-controls="toc-Nomenclature-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 Nomenclature subsection</span> </button> <ul id="toc-Nomenclature-sublist" class="vector-toc-list"> <li id="toc-Etymology" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Etymology"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.1</span> <span>Etymology</span> </div> </a> <ul id="toc-Etymology-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-IUPAC_nomenclature" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#IUPAC_nomenclature"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.2</span> <span>IUPAC nomenclature</span> </div> </a> <ul id="toc-IUPAC_nomenclature-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Orthoesters" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Orthoesters"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.3</span> <span>Orthoesters</span> </div> </a> <ul id="toc-Orthoesters-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Esters_of_inorganic_acids" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Esters_of_inorganic_acids"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.4</span> <span>Esters of inorganic acids</span> </div> </a> <ul id="toc-Esters_of_inorganic_acids-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Structure_and_bonding" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Structure_and_bonding"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>Structure and bonding</span> </div> </a> <ul id="toc-Structure_and_bonding-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Physical_properties_and_characterization" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Physical_properties_and_characterization"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Physical properties and characterization</span> </div> </a> <button aria-controls="toc-Physical_properties_and_characterization-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 Physical properties and characterization subsection</span> </button> <ul id="toc-Physical_properties_and_characterization-sublist" class="vector-toc-list"> <li id="toc-Characterization_and_analysis" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Characterization_and_analysis"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.1</span> <span>Characterization and analysis</span> </div> </a> <ul id="toc-Characterization_and_analysis-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Applications_and_occurrence" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Applications_and_occurrence"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Applications and occurrence</span> </div> </a> <ul id="toc-Applications_and_occurrence-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Preparation" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Preparation"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Preparation</span> </div> </a> <button aria-controls="toc-Preparation-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 Preparation subsection</span> </button> <ul id="toc-Preparation-sublist" class="vector-toc-list"> <li id="toc-Esterification_of_carboxylic_acids_with_alcohols" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Esterification_of_carboxylic_acids_with_alcohols"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1</span> <span>Esterification of carboxylic acids with alcohols</span> </div> </a> <ul id="toc-Esterification_of_carboxylic_acids_with_alcohols-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Esterification_of_carboxylic_acids_with_epoxides" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Esterification_of_carboxylic_acids_with_epoxides"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.2</span> <span>Esterification of carboxylic acids with epoxides</span> </div> </a> <ul id="toc-Esterification_of_carboxylic_acids_with_epoxides-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Alcoholysis_of_acyl_chlorides_and_acid_anhydrides" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Alcoholysis_of_acyl_chlorides_and_acid_anhydrides"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.3</span> <span>Alcoholysis of acyl chlorides and acid anhydrides</span> </div> </a> <ul id="toc-Alcoholysis_of_acyl_chlorides_and_acid_anhydrides-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Alkylation_of_carboxylic_acids_and_their_salts" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Alkylation_of_carboxylic_acids_and_their_salts"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.4</span> <span>Alkylation of carboxylic acids and their salts</span> </div> </a> <ul id="toc-Alkylation_of_carboxylic_acids_and_their_salts-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Transesterification" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Transesterification"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.5</span> <span>Transesterification</span> </div> </a> <ul id="toc-Transesterification-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Carbonylation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Carbonylation"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.6</span> <span>Carbonylation</span> </div> </a> <ul id="toc-Carbonylation-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Addition_of_carboxylic_acids_to_alkenes_and_alkynes" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Addition_of_carboxylic_acids_to_alkenes_and_alkynes"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.7</span> <span>Addition of carboxylic acids to alkenes and alkynes</span> </div> </a> <ul id="toc-Addition_of_carboxylic_acids_to_alkenes_and_alkynes-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-From_aldehydes" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#From_aldehydes"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.8</span> <span>From aldehydes</span> </div> </a> <ul id="toc-From_aldehydes-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Other_methods" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Other_methods"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.9</span> <span>Other methods</span> </div> </a> <ul id="toc-Other_methods-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Reactions" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Reactions"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Reactions</span> </div> </a> <button aria-controls="toc-Reactions-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 Reactions subsection</span> </button> <ul id="toc-Reactions-sublist" class="vector-toc-list"> <li id="toc-Transesterification_2" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Transesterification_2"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.1</span> <span>Transesterification</span> </div> </a> <ul id="toc-Transesterification_2-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Hydrolysis_and_saponification" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Hydrolysis_and_saponification"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.2</span> <span>Hydrolysis and saponification</span> </div> </a> <ul id="toc-Hydrolysis_and_saponification-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Reduction" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Reduction"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.3</span> <span>Reduction</span> </div> </a> <ul id="toc-Reduction-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Claisen_condensation_and_related_reactions" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Claisen_condensation_and_related_reactions"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.4</span> <span>Claisen condensation and related reactions</span> </div> </a> <ul id="toc-Claisen_condensation_and_related_reactions-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Other_ester_reactivities" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Other_ester_reactivities"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.5</span> <span>Other ester reactivities</span> </div> </a> <ul id="toc-Other_ester_reactivities-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">6.6</span> <span>Other reactions</span> </div> </a> <ul id="toc-Other_reactions-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Protecting_groups" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Protecting_groups"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.7</span> <span>Protecting groups</span> </div> </a> <ul id="toc-Protecting_groups-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-List_of_ester_odorants" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#List_of_ester_odorants"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>List of ester odorants</span> </div> </a> <ul id="toc-List_of_ester_odorants-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">8</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">9</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">10</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" > <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">Ester</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 78 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-78" 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">78 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/Ester" title="Ester – Afrikaans" lang="af" hreflang="af" data-title="Ester" data-language-autonym="Afrikaans" data-language-local-name="Afrikaans" class="interlanguage-link-target"><span>Afrikaans</span></a></li><li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%A5%D8%B3%D8%AA%D8%B1" title="إستر – Arabic" lang="ar" hreflang="ar" data-title="إستر" 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/%C3%89ster" title="Éster – Asturian" lang="ast" hreflang="ast" data-title="Éster" 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/M%C3%BCr%C9%99kk%C9%99b_efirl%C9%99r" title="Mürəkkəb efirlər – Azerbaijani" lang="az" hreflang="az" data-title="Mürəkkəb efirlər" data-language-autonym="Azərbaycanca" data-language-local-name="Azerbaijani" class="interlanguage-link-target"><span>Azərbaycanca</span></a></li><li class="interlanguage-link interwiki-zh-min-nan mw-list-item"><a href="https://zh-min-nan.wikipedia.org/wiki/Ester" title="Ester – Minnan" lang="nan" hreflang="nan" data-title="Ester" data-language-autonym="閩南語 / Bân-lâm-gú" data-language-local-name="Minnan" class="interlanguage-link-target"><span>閩南語 / Bân-lâm-gú</span></a></li><li class="interlanguage-link interwiki-be mw-list-item"><a href="https://be.wikipedia.org/wiki/%D0%AD%D1%81%D1%82%D1%8D%D1%80%D1%8B" title="Эстэры – Belarusian" lang="be" hreflang="be" data-title="Эстэры" data-language-autonym="Беларуская" data-language-local-name="Belarusian" class="interlanguage-link-target"><span>Беларуская</span></a></li><li class="interlanguage-link interwiki-be-x-old mw-list-item"><a href="https://be-tarask.wikipedia.org/wiki/%D0%A1%D0%BA%D0%BB%D0%B0%D0%B4%D0%B0%D0%BD%D1%8B%D1%8F_%D1%8D%D1%82%D1%8D%D1%80%D1%8B" title="Складаныя этэры – Belarusian (Taraškievica orthography)" lang="be-tarask" hreflang="be-tarask" data-title="Складаныя этэры" data-language-autonym="Беларуская (тарашкевіца)" data-language-local-name="Belarusian (Taraškievica orthography)" class="interlanguage-link-target"><span>Беларуская (тарашкевіца)</span></a></li><li class="interlanguage-link interwiki-bcl mw-list-item"><a href="https://bcl.wikipedia.org/wiki/Ester" title="Ester – Central Bikol" lang="bcl" hreflang="bcl" data-title="Ester" data-language-autonym="Bikol Central" data-language-local-name="Central Bikol" class="interlanguage-link-target"><span>Bikol Central</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%95%D1%81%D1%82%D0%B5%D1%80" title="Естер – Bulgarian" lang="bg" hreflang="bg" data-title="Естер" 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/Ester" title="Ester – Bosnian" lang="bs" hreflang="bs" data-title="Ester" 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/%C3%88ster" title="Èster – Catalan" lang="ca" hreflang="ca" data-title="Èster" 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/Estery" title="Estery – Czech" lang="cs" hreflang="cs" data-title="Estery" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-cy mw-list-item"><a href="https://cy.wikipedia.org/wiki/Ester" title="Ester – Welsh" lang="cy" hreflang="cy" data-title="Ester" data-language-autonym="Cymraeg" data-language-local-name="Welsh" class="interlanguage-link-target"><span>Cymraeg</span></a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Ester_(kemi)" title="Ester (kemi) – Danish" lang="da" hreflang="da" data-title="Ester (kemi)" data-language-autonym="Dansk" data-language-local-name="Danish" class="interlanguage-link-target"><span>Dansk</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Ester" title="Ester – German" lang="de" hreflang="de" data-title="Ester" 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/Estrid" title="Estrid – Estonian" lang="et" hreflang="et" data-title="Estrid" 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%95%CF%83%CF%84%CE%AD%CF%81%CE%B5%CF%82" title="Εστέρες – Greek" lang="el" hreflang="el" data-title="Εστέρες" 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/%C3%89ster" title="Éster – Spanish" lang="es" hreflang="es" data-title="Éster" 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/Estero" title="Estero – Esperanto" lang="eo" hreflang="eo" data-title="Estero" 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/Ester" title="Ester – Basque" lang="eu" hreflang="eu" data-title="Ester" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%A7%D8%B3%D8%AA%D8%B1_(%D8%B4%DB%8C%D9%85%DB%8C)" title="استر (شیمی) – Persian" lang="fa" hreflang="fa" data-title="استر (شیمی)" 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/Ester" title="Ester – French" lang="fr" hreflang="fr" data-title="Ester" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-fy mw-list-item"><a href="https://fy.wikipedia.org/wiki/Ester_(skiekunde)" title="Ester (skiekunde) – Western Frisian" lang="fy" hreflang="fy" data-title="Ester (skiekunde)" data-language-autonym="Frysk" data-language-local-name="Western Frisian" class="interlanguage-link-target"><span>Frysk</span></a></li><li class="interlanguage-link interwiki-ga mw-list-item"><a href="https://ga.wikipedia.org/wiki/Eistear" title="Eistear – Irish" lang="ga" hreflang="ga" data-title="Eistear" 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/%C3%89ster" title="Éster – Galician" lang="gl" hreflang="gl" data-title="Éster" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EC%97%90%EC%8A%A4%ED%84%B0" title="에스터 – Korean" lang="ko" hreflang="ko" data-title="에스터" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D4%B7%D5%BD%D5%A9%D5%A5%D6%80%D5%B6%D5%A5%D6%80" title="Էսթերներ – Armenian" lang="hy" hreflang="hy" data-title="Էսթերներ" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-hi mw-list-item"><a href="https://hi.wikipedia.org/wiki/%E0%A4%8F%E0%A4%B8%E0%A5%8D%E0%A4%9F%E0%A4%B0" title="एस्टर – Hindi" lang="hi" hreflang="hi" data-title="एस्टर" 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/Esteri" title="Esteri – Croatian" lang="hr" hreflang="hr" data-title="Esteri" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Ester_(kimia)" title="Ester (kimia) – Indonesian" lang="id" hreflang="id" data-title="Ester (kimia)" 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-is mw-list-item"><a href="https://is.wikipedia.org/wiki/Estri" title="Estri – Icelandic" lang="is" hreflang="is" data-title="Estri" data-language-autonym="Íslenska" data-language-local-name="Icelandic" class="interlanguage-link-target"><span>Íslenska</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Esteri" title="Esteri – Italian" lang="it" hreflang="it" data-title="Esteri" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%90%D7%A1%D7%98%D7%A8" title="אסטר – Hebrew" lang="he" hreflang="he" data-title="אסטר" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-kk mw-list-item"><a href="https://kk.wikipedia.org/wiki/%D0%9A%D2%AF%D1%80%D0%B4%D0%B5%D0%BB%D1%96_%D1%8D%D1%84%D0%B8%D1%80%D0%BB%D0%B5%D1%80" title="Күрделі эфирлер – Kazakh" lang="kk" hreflang="kk" data-title="Күрделі эфирлер" data-language-autonym="Қазақша" data-language-local-name="Kazakh" class="interlanguage-link-target"><span>Қазақша</span></a></li><li class="interlanguage-link interwiki-ht mw-list-item"><a href="https://ht.wikipedia.org/wiki/Est%C3%A8" title="Estè – Haitian Creole" lang="ht" hreflang="ht" data-title="Estè" data-language-autonym="Kreyòl ayisyen" data-language-local-name="Haitian Creole" class="interlanguage-link-target"><span>Kreyòl ayisyen</span></a></li><li class="interlanguage-link interwiki-la mw-list-item"><a href="https://la.wikipedia.org/wiki/Ester" title="Ester – Latin" lang="la" hreflang="la" data-title="Ester" 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/Esteri" title="Esteri – Latvian" lang="lv" hreflang="lv" data-title="Esteri" 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/Esteris" title="Esteris – Lithuanian" lang="lt" hreflang="lt" data-title="Esteris" data-language-autonym="Lietuvių" data-language-local-name="Lithuanian" class="interlanguage-link-target"><span>Lietuvių</span></a></li><li class="interlanguage-link interwiki-lmo mw-list-item"><a href="https://lmo.wikipedia.org/wiki/Ester" title="Ester – Lombard" lang="lmo" hreflang="lmo" data-title="Ester" data-language-autonym="Lombard" data-language-local-name="Lombard" class="interlanguage-link-target"><span>Lombard</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/%C3%89szterek" title="Észterek – Hungarian" lang="hu" hreflang="hu" data-title="Észterek" 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%95%D1%81%D1%82%D0%B5%D1%80" title="Естер – Macedonian" lang="mk" hreflang="mk" data-title="Естер" 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%8E%E0%B4%B8%E0%B5%8D%E0%B4%B1%E0%B5%8D%E0%B4%B1%E0%B5%BC" title="എസ്റ്റർ – Malayalam" lang="ml" hreflang="ml" data-title="എസ്റ്റർ" 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/Ester" title="Ester – Malay" lang="ms" hreflang="ms" data-title="Ester" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" class="interlanguage-link-target"><span>Bahasa Melayu</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Ester_(scheikunde)" title="Ester (scheikunde) – Dutch" lang="nl" hreflang="nl" data-title="Ester (scheikunde)" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%A8%E3%82%B9%E3%83%86%E3%83%AB" title="エステル – Japanese" lang="ja" hreflang="ja" data-title="エステル" 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-frr mw-list-item"><a href="https://frr.wikipedia.org/wiki/Ester" title="Ester – Northern Frisian" lang="frr" hreflang="frr" data-title="Ester" data-language-autonym="Nordfriisk" data-language-local-name="Northern Frisian" class="interlanguage-link-target"><span>Nordfriisk</span></a></li><li class="interlanguage-link interwiki-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Ester" title="Ester – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Ester" data-language-autonym="Norsk bokmål" data-language-local-name="Norwegian Bokmål" class="interlanguage-link-target"><span>Norsk bokmål</span></a></li><li class="interlanguage-link interwiki-nn mw-list-item"><a href="https://nn.wikipedia.org/wiki/Ester" title="Ester – Norwegian Nynorsk" lang="nn" hreflang="nn" data-title="Ester" data-language-autonym="Norsk nynorsk" data-language-local-name="Norwegian Nynorsk" class="interlanguage-link-target"><span>Norsk nynorsk</span></a></li><li class="interlanguage-link interwiki-oc mw-list-item"><a href="https://oc.wikipedia.org/wiki/Est%C3%A8r" title="Estèr – Occitan" lang="oc" hreflang="oc" data-title="Estèr" data-language-autonym="Occitan" data-language-local-name="Occitan" class="interlanguage-link-target"><span>Occitan</span></a></li><li class="interlanguage-link interwiki-pa mw-list-item"><a href="https://pa.wikipedia.org/wiki/%E0%A8%90%E0%A8%B8%E0%A8%9F%E0%A8%B0" title="ਐਸਟਰ – Punjabi" lang="pa" hreflang="pa" data-title="ਐਸਟਰ" data-language-autonym="ਪੰਜਾਬੀ" data-language-local-name="Punjabi" class="interlanguage-link-target"><span>ਪੰਜਾਬੀ</span></a></li><li class="interlanguage-link interwiki-ps mw-list-item"><a href="https://ps.wikipedia.org/wiki/%D8%A7%DB%8C%D8%B3%D8%AA%D8%B1" title="ایستر – Pashto" lang="ps" hreflang="ps" data-title="ایستر" data-language-autonym="پښتو" data-language-local-name="Pashto" class="interlanguage-link-target"><span>پښتو</span></a></li><li class="interlanguage-link interwiki-nds mw-list-item"><a href="https://nds.wikipedia.org/wiki/Ester" title="Ester – Low German" lang="nds" hreflang="nds" data-title="Ester" data-language-autonym="Plattdüütsch" data-language-local-name="Low German" class="interlanguage-link-target"><span>Plattdüütsch</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Estry" title="Estry – Polish" lang="pl" hreflang="pl" data-title="Estry" 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/%C3%89ster" title="Éster – Portuguese" lang="pt" hreflang="pt" data-title="Éster" 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/Ester" title="Ester – Romanian" lang="ro" hreflang="ro" data-title="Ester" 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%A1%D0%BB%D0%BE%D0%B6%D0%BD%D1%8B%D0%B5_%D1%8D%D1%84%D0%B8%D1%80%D1%8B" title="Сложные эфиры – Russian" lang="ru" hreflang="ru" data-title="Сложные эфиры" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sq mw-list-item"><a href="https://sq.wikipedia.org/wiki/Esteret" title="Esteret – Albanian" lang="sq" hreflang="sq" data-title="Esteret" data-language-autonym="Shqip" data-language-local-name="Albanian" class="interlanguage-link-target"><span>Shqip</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Ester" title="Ester – Simple English" lang="en-simple" hreflang="en-simple" data-title="Ester" 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/Ester_(chemick%C3%A1_zl%C3%BA%C4%8Denina)" title="Ester (chemická zlúčenina) – Slovak" lang="sk" hreflang="sk" data-title="Ester (chemická zlúčenina)" 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/Ester" title="Ester – Slovenian" lang="sl" hreflang="sl" data-title="Ester" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-ckb mw-list-item"><a href="https://ckb.wikipedia.org/wiki/%D8%A6%DB%95%D8%B3%D8%AA%DB%95%D8%B1" title="ئەستەر – Central Kurdish" lang="ckb" hreflang="ckb" data-title="ئەستەر" data-language-autonym="کوردی" data-language-local-name="Central Kurdish" class="interlanguage-link-target"><span>کوردی</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Estar" title="Estar – Serbian" lang="sr" hreflang="sr" data-title="Estar" 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/Estri" title="Estri – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Estri" 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/%C3%89ster" title="Éster – Sundanese" lang="su" hreflang="su" data-title="Éster" 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/Esterit" title="Esterit – Finnish" lang="fi" hreflang="fi" data-title="Esterit" 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/Estrar" title="Estrar – Swedish" lang="sv" hreflang="sv" data-title="Estrar" 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%8E%E0%AE%9A%E0%AF%81%E0%AE%A4%E0%AF%8D%E0%AE%A4%E0%AE%B0%E0%AF%8D" title="எசுத்தர் – Tamil" lang="ta" hreflang="ta" data-title="எசுத்தர்" 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%8E%E0%B0%B8%E0%B1%8D%E0%B0%9F%E0%B0%B0%E0%B1%8D" title="ఎస్టర్ – Telugu" lang="te" hreflang="te" data-title="ఎస్టర్" 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%B9%80%E0%B8%AD%E0%B8%AA%E0%B9%80%E0%B8%97%E0%B8%AD%E0%B8%A3%E0%B9%8C" title="เอสเทอร์ – Thai" lang="th" hreflang="th" data-title="เอสเทอร์" 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/Ester" title="Ester – Turkish" lang="tr" hreflang="tr" data-title="Ester" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%95%D1%81%D1%82%D0%B5%D1%80%D0%B8" title="Естери – Ukrainian" lang="uk" hreflang="uk" data-title="Естери" 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/%D8%A7%D8%B3%D9%B9%D8%B1" title="اسٹر – Urdu" lang="ur" hreflang="ur" data-title="اسٹر" 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/Ester" title="Ester – Vietnamese" lang="vi" hreflang="vi" data-title="Ester" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target"><span>Tiếng Việt</span></a></li><li class="interlanguage-link interwiki-zh-classical mw-list-item"><a href="https://zh-classical.wikipedia.org/wiki/%E9%85%AF" title="酯 – Literary Chinese" lang="lzh" hreflang="lzh" data-title="酯" data-language-autonym="文言" data-language-local-name="Literary Chinese" class="interlanguage-link-target"><span>文言</span></a></li><li class="interlanguage-link interwiki-war mw-list-item"><a href="https://war.wikipedia.org/wiki/Ester" title="Ester – Waray" lang="war" hreflang="war" data-title="Ester" 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/%E9%85%AF" title="酯 – Wu" lang="wuu" hreflang="wuu" data-title="酯" data-language-autonym="吴语" data-language-local-name="Wu" class="interlanguage-link-target"><span>吴语</span></a></li><li class="interlanguage-link interwiki-zh-yue mw-list-item"><a href="https://zh-yue.wikipedia.org/wiki/%E9%85%AF" title="酯 – Cantonese" lang="yue" hreflang="yue" data-title="酯" data-language-autonym="粵語" data-language-local-name="Cantonese" class="interlanguage-link-target"><span>粵語</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E9%85%AF" title="酯 – Chinese" lang="zh" hreflang="zh" data-title="酯" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target"><span>中文</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span class="wb-langlinks-edit wb-langlinks-link"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q101487#sitelinks-wikipedia" title="Edit interlanguage links" class="wbc-editpage">Edit links</a></span></div> </div> </div> </div> </header> <div class="vector-page-toolbar"> <div class="vector-page-toolbar-container"> <div id="left-navigation"> <nav aria-label="Namespaces"> <div id="p-associated-pages" class="vector-menu vector-menu-tabs mw-portlet mw-portlet-associated-pages" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="ca-nstab-main" class="selected vector-tab-noicon mw-list-item"><a href="/wiki/Ester" 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print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">For other uses, see <a href="/wiki/Ester_(disambiguation)" class="mw-disambig" title="Ester (disambiguation)">Ester (disambiguation)</a>.</div> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Ester-general.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/34/Ester-general.svg/130px-Ester-general.svg.png" decoding="async" width="130" height="100" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/34/Ester-general.svg/195px-Ester-general.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/34/Ester-general.svg/260px-Ester-general.svg.png 2x" data-file-width="625" data-file-height="480" /></a><figcaption>An ester of a <a href="/wiki/Carboxylic_acid" title="Carboxylic acid">carboxylic acid</a>. R stands for any group (typically <a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a> or <a href="/wiki/Organyl" class="mw-redirect" title="Organyl">organyl</a>) and R<span class="nowrap" style="padding-left:0.15em;">′</span> stands for any organyl group.</figcaption></figure> <p>In <a href="/wiki/Chemistry" title="Chemistry">chemistry</a>, an <b>ester</b> is a <a href="/wiki/Chemical_compound" title="Chemical compound">compound</a> derived from an <a href="/wiki/Acid" title="Acid">acid</a> (organic or inorganic) in which the <a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a> atom (H) of at least one <a href="/wiki/Acid" title="Acid">acidic</a> <a href="/wiki/Hydroxyl" class="mw-redirect" title="Hydroxyl">hydroxyl</a> group (<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">−OH</span>) of that acid is replaced by an <a href="/wiki/Organyl" class="mw-redirect" title="Organyl">organyl</a> group (R<span class="nowrap" style="padding-left:0.15em;">′</span>).<sup id="cite_ref-iupac_1-0" class="reference"><a href="#cite_note-iupac-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> These compounds contain a <a href="/wiki/Functional_group#Groups_containing_oxygen" title="Functional group">distinctive functional group</a>. Analogues derived from <a href="/wiki/Oxygen" title="Oxygen">oxygen</a> replaced by other <a href="/wiki/Chalcogen" title="Chalcogen">chalcogens</a> belong to the ester category as well.<sup id="cite_ref-iupac_1-1" class="reference"><a href="#cite_note-iupac-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> According to some authors, organyl derivatives of acidic hydrogen of other acids are esters as well (e.g. <a href="/wiki/Amides" class="mw-redirect" title="Amides">amides</a>), but not according to the <a href="/wiki/IUPAC" class="mw-redirect" title="IUPAC">IUPAC</a>.<sup id="cite_ref-iupac_1-2" class="reference"><a href="#cite_note-iupac-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p><p><a href="/wiki/Glycerides" class="mw-redirect" title="Glycerides">Glycerides</a> are <a href="/wiki/Fatty_acid_ester" title="Fatty acid ester">fatty acid esters</a> of <a href="/wiki/Glycerol" title="Glycerol">glycerol</a>; they are important in biology, being one of the main classes of <a href="/wiki/Lipid" title="Lipid">lipids</a> and comprising the bulk of <a href="/wiki/Animal_fat" title="Animal fat">animal fats</a> and <a href="/wiki/Vegetable_oil" title="Vegetable oil">vegetable oils</a>. <a href="/wiki/Lactone" title="Lactone">Lactones</a> are cyclic carboxylic esters; naturally occurring lactones are mainly 5- and 6-membered ring lactones. Lactones contribute to the aroma of fruits, butter, cheese, <a href="/wiki/Vegetables" class="mw-redirect" title="Vegetables">vegetables</a> like <a href="/wiki/Celery" title="Celery">celery</a> and other foods. </p><p>Esters can be formed from <a href="/wiki/Oxoacid" class="mw-redirect" title="Oxoacid">oxoacids</a> (e.g. esters of <a href="/wiki/Acetic_acid" title="Acetic acid">acetic acid</a>, <a href="/wiki/Carbonic_acid" title="Carbonic acid">carbonic acid</a>, <a href="/wiki/Sulfuric_acid" title="Sulfuric acid">sulfuric acid</a>, <a href="/wiki/Phosphoric_acid" title="Phosphoric acid">phosphoric acid</a>, <a href="/wiki/Nitric_acid" title="Nitric acid">nitric acid</a>, <a href="/wiki/Xanthic_acid" class="mw-redirect" title="Xanthic acid">xanthic acid</a>), but also from acids that do not contain oxygen (e.g. esters of <a href="/wiki/Thiocyanic_acid" title="Thiocyanic acid">thiocyanic acid</a> and <a href="/wiki/Trithiocarbonate" class="mw-redirect" title="Trithiocarbonate">trithiocarbonic acid</a>). An example of an ester formation is the <a href="/wiki/Substitution_reaction" title="Substitution reaction">substitution reaction</a> between a <a href="/wiki/Carboxylic_acid" title="Carboxylic acid">carboxylic acid</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">R−C(=O)−OH</span>) and an <a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">alcohol</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">R'−OH</span>), forming an ester (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">R−C(=O)−O−R'</span>), where R stands for any group (typically hydrogen or organyl) and R<span class="nowrap" style="padding-left:0.15em;">′</span> stands for organyl group. </p><p>Organyl esters of carboxylic acids typically have a pleasant smell; those of low molecular weight are commonly used as fragrances and are found in <a href="/wiki/Essential_oil" title="Essential oil">essential oils</a> and <a href="/wiki/Pheromone" title="Pheromone">pheromones</a>. They perform as high-grade <a href="/wiki/Solvent" title="Solvent">solvents</a> for a broad array of <a href="/wiki/Plastics" class="mw-redirect" title="Plastics">plastics</a>, <a href="/wiki/Plasticizer" title="Plasticizer">plasticizers</a>, <a href="/wiki/Resin" title="Resin">resins</a>, and <a href="/wiki/Lacquer" title="Lacquer">lacquers</a>,<sup id="cite_ref-Wright1986_2-0" class="reference"><a href="#cite_note-Wright1986-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> and are one of the largest classes of synthetic <a href="/wiki/Lubricants" class="mw-redirect" title="Lubricants">lubricants</a> on the commercial market.<sup id="cite_ref-Booser1993_3-0" class="reference"><a href="#cite_note-Booser1993-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Polyester" title="Polyester">Polyesters</a> are important plastics, with <a href="/wiki/Monomer" title="Monomer">monomers</a> linked by ester <a href="/wiki/Moiety_(chemistry)" title="Moiety (chemistry)">moieties</a>. <a href="/wiki/Phosphoester" class="mw-redirect" title="Phosphoester">Esters of phosphoric acid</a> form the backbone of <a href="/wiki/DNA" title="DNA">DNA</a> molecules. <a href="/wiki/Nitrate_ester" title="Nitrate ester">Esters of nitric acid</a>, such as <a href="/wiki/Nitroglycerin" title="Nitroglycerin">nitroglycerin</a>, are known for their explosive properties. </p><p>There are compounds in which an acidic hydrogen of acids mentioned in this article are not replaced by an organyl, but by some other group. According to some authors, those compounds are esters as well, especially when the first carbon atom of the organyl group replacing acidic hydrogen, is replaced by another atom from the <a href="/wiki/Group_14_elements" class="mw-redirect" title="Group 14 elements">group 14 elements</a> (<a href="/wiki/Silicon" title="Silicon">Si</a>, <a href="/wiki/Germanium" title="Germanium">Ge</a>, <a href="/wiki/Tin" title="Tin">Sn</a>, <a href="/wiki/Lead" title="Lead">Pb</a>); for example, according to them, <a href="/w/index.php?title=Trimethylstannyl_acetate&action=edit&redlink=1" class="new" title="Trimethylstannyl acetate (page does not exist)">trimethylstannyl acetate</a> (or trimethyltin acetate) <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>COOSn(CH<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">3</sub></span> is a <a href="/wiki/Organotin" class="mw-redirect" title="Organotin">trimethylstannyl</a> ester of <a href="/wiki/Acetic_acid" title="Acetic acid">acetic acid</a>, and <a href="/wiki/Dibutyltin_dilaurate" title="Dibutyltin dilaurate">dibutyltin dilaurate</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">(CH<sub class="template-chem2-sub">3</sub>(CH<sub class="template-chem2-sub">2</sub>)<sub class="template-chem2-sub">10</sub>COO)<sub class="template-chem2-sub">2</sub>Sn((CH<sub class="template-chem2-sub">2</sub>)<sub class="template-chem2-sub">3</sub>CH<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">2</sub></span> is a <a href="/wiki/Organotin" class="mw-redirect" title="Organotin">dibutylstannylene</a> ester of <a href="/wiki/Lauric_acid" title="Lauric acid">lauric acid</a>, and the <a href="/wiki/Phillips_catalyst" title="Phillips catalyst">Phillips catalyst</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CrO<sub class="template-chem2-sub">2</sub>(OSi(OCH<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">2</sub></span> is a trimethoxysilyl ester of <a href="/wiki/Chromic_acid" title="Chromic acid">chromic acid</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">H<sub class="template-chem2-sub">2</sub>CrO<sub class="template-chem2-sub">4</sub></span>).<sup id="cite_ref-pubchem1_4-0" class="reference"><a href="#cite_note-pubchem1-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-chemspider1_5-0" class="reference"><a href="#cite_note-chemspider1-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Nomenclature">Nomenclature</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ester&action=edit&section=1" title="Edit section: Nomenclature"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Etymology">Etymology</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ester&action=edit&section=2" title="Edit section: Etymology"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The word <i>ester</i> was coined in 1848 by a German chemist <a href="/wiki/Leopold_Gmelin" title="Leopold Gmelin">Leopold Gmelin</a>,<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> probably as a contraction of the German <span title="German-language text"><i lang="de">Essigäther</i></span>, "<a href="/wiki/Ethyl_acetate" title="Ethyl acetate">acetic ether</a>". </p> <div class="mw-heading mw-heading3"><h3 id="IUPAC_nomenclature">IUPAC nomenclature</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ester&action=edit&section=3" title="Edit section: IUPAC nomenclature"><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/IUPAC_nomenclature_of_organic_chemistry#Esters" title="IUPAC nomenclature of organic chemistry">IUPAC nomenclature of organic chemistry § Esters</a></div> <p>The names of esters that are formed from an alcohol and an acid, are derived from the parent alcohol and the parent acid, where the latter may be organic or inorganic. Esters derived from the simplest <a href="/wiki/Carboxylic_acid" title="Carboxylic acid">carboxylic acids</a> are commonly named according to the more traditional, so-called "<a href="/wiki/Trivial_names" class="mw-redirect" title="Trivial names">trivial names</a>" e.g. as formate, acetate, propionate, and butyrate, as opposed to the IUPAC nomenclature methanoate, ethanoate, propanoate, and butanoate. Esters derived from more complex carboxylic acids are, on the other hand, more frequently named using the systematic IUPAC name, based on the name for the acid followed by the suffix <i>-oate</i>. For example, the ester hexyl octanoate, also known under the trivial name hexyl <a href="/wiki/Caprylic_acid" title="Caprylic acid">caprylate</a>, has the formula <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>(CH<sub class="template-chem2-sub">2</sub>)<sub class="template-chem2-sub">6</sub>CO<sub class="template-chem2-sub">2</sub>(CH<sub class="template-chem2-sub">2</sub>)<sub class="template-chem2-sub">5</sub>CH<sub class="template-chem2-sub">3</sub></span>. </p> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Butyl_acetate_ester_example.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c0/Butyl_acetate_ester_example.png/220px-Butyl_acetate_ester_example.png" decoding="async" width="220" height="111" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c0/Butyl_acetate_ester_example.png/330px-Butyl_acetate_ester_example.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c0/Butyl_acetate_ester_example.png/440px-Butyl_acetate_ester_example.png 2x" data-file-width="1080" data-file-height="547" /></a><figcaption><a href="/wiki/Butyl_acetate" title="Butyl acetate">Butyl acetate</a>, an ester derived from a residue of <a href="/wiki/Butanol" title="Butanol">butanol</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>CH<sub class="template-chem2-sub">2</sub>CH<sub class="template-chem2-sub">2</sub>CH<sub class="template-chem2-sub">2</sub>OH</span>) (the butanol residue is <a href="/wiki/Butyl_group" title="Butyl group">butyl group</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−CH<sub class="template-chem2-sub">2</sub>CH<sub class="template-chem2-sub">2</sub>CH<sub class="template-chem2-sub">2</sub>CH<sub class="template-chem2-sub">3</sub></span>) (right side of the picture, blue) and <a href="/wiki/Acetic_acid" title="Acetic acid">acetic acid</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>CO<sub class="template-chem2-sub">2</sub>H</span> (left side of the picture, orange). The <a href="/wiki/Acid" title="Acid">acidic</a> <a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a> atom (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−H</span>) from acetic acid <a href="/wiki/Molecule" title="Molecule">molecule</a> is replaced by the butyl group.</figcaption></figure> <p>The chemical formulas of organic esters formed from carboxylic acids and alcohols usually take the form <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">RCO<sub class="template-chem2-sub">2</sub>R'</span> or RCOOR', where R and R' are the <a href="/wiki/Organyl" class="mw-redirect" title="Organyl">organyl</a> parts of the carboxylic acid and the alcohol, respectively, and R can be a <a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a> in the case of esters of <a href="/wiki/Formic_acid" title="Formic acid">formic acid</a>. For example, <a href="/wiki/Butyl_acetate" title="Butyl acetate">butyl acetate</a> (systematically butyl ethanoate), derived from <a href="/wiki/N-Butanol" class="mw-redirect" title="N-Butanol">butanol</a> and <a href="/wiki/Acetic_acid" title="Acetic acid">acetic acid</a> (systematically ethanoic acid) would be written <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>CO<sub class="template-chem2-sub">2</sub>(CH<sub class="template-chem2-sub">2</sub>)<sub class="template-chem2-sub">3</sub>CH<sub class="template-chem2-sub">3</sub></span>. Alternative presentations are common including BuOAc and <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>COO(CH<sub class="template-chem2-sub">2</sub>)<sub class="template-chem2-sub">3</sub>CH<sub class="template-chem2-sub">3</sub></span>. </p><p>Cyclic esters are called <a href="/wiki/Lactone" title="Lactone">lactones</a>, regardless of whether they are derived from an organic or inorganic acid. One example of an organic lactone is <a href="/wiki/Gamma-valerolactone" class="mw-redirect" title="Gamma-valerolactone">γ-valerolactone</a>. </p> <div class="mw-heading mw-heading3"><h3 id="Orthoesters">Orthoesters</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ester&action=edit&section=4" title="Edit section: Orthoesters"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>An uncommon class of esters are the <a href="/wiki/Orthoester" class="mw-redirect" title="Orthoester">orthoesters</a>. One of them are the esters of orthocarboxylic acids. Those esters have the formula <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">RC(OR′)<sub class="template-chem2-sub">3</sub></span>, where R stands for any group (organic or inorganic) and R<span class="nowrap" style="padding-left:0.15em;">′</span> stands for <a href="/wiki/Organyl" class="mw-redirect" title="Organyl">organyl</a> group. For example, <a href="/wiki/Triethyl_orthoformate" title="Triethyl orthoformate">triethyl orthoformate</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">HC(OCH<sub class="template-chem2-sub">2</sub>CH<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">3</sub></span>) is derived, in terms of its name (but not its synthesis) from <a href="/wiki/Esterification" class="mw-redirect" title="Esterification">esterification</a> of <a href="/wiki/Orthoformic_acid" title="Orthoformic acid">orthoformic acid</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">HC(OH)<sub class="template-chem2-sub">3</sub></span>) with <a href="/wiki/Ethanol" title="Ethanol">ethanol</a>. </p> <div class="mw-heading mw-heading3"><h3 id="Esters_of_inorganic_acids">Esters of inorganic acids</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ester&action=edit&section=5" title="Edit section: Esters of inorganic acids"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Phosphate_Group.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d2/Phosphate_Group.svg/130px-Phosphate_Group.svg.png" decoding="async" width="130" height="79" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d2/Phosphate_Group.svg/195px-Phosphate_Group.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d2/Phosphate_Group.svg/260px-Phosphate_Group.svg.png 2x" data-file-width="1025" data-file-height="621" /></a><figcaption>A phosphoric acid ester, where R stands for an <a href="/wiki/Organyl" class="mw-redirect" title="Organyl">organyl</a> group.</figcaption></figure> <p>Esters can also be derived from inorganic acids. </p> <ul><li><a href="/wiki/Perchloric_acid" title="Perchloric acid">Perchloric acid</a> forms <a href="/wiki/Perchlorate" title="Perchlorate">perchlorate</a> esters, e.g., <a href="/wiki/Methyl_perchlorate" title="Methyl perchlorate">methyl perchlorate</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>−O−Cl(=O)<sub class="template-chem2-sub">3</sub></span>)</li> <li><a href="/wiki/Sulfuric_acid" title="Sulfuric acid">Sulfuric acid</a> forms <a href="/wiki/Organosulfate" title="Organosulfate">sulfate esters</a>, e.g., <a href="/wiki/Dimethyl_sulfate" title="Dimethyl sulfate">dimethyl sulfate</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">(CH<sub class="template-chem2-sub">3</sub>−O−)<sub class="template-chem2-sub">2</sub>S(=O)<sub class="template-chem2-sub">2</sub></span>) and <a href="/wiki/Methyl_bisulfate" title="Methyl bisulfate">methyl bisulfate</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>−O−S(=O)<sub class="template-chem2-sub">2</sub>−OH</span>)</li> <li><a href="/wiki/Nitric_acid" title="Nitric acid">Nitric acid</a> forms <a href="/wiki/Organic_nitrate" class="mw-redirect" title="Organic nitrate">nitrate esters</a>, e.g. <a href="/wiki/Methyl_nitrate" title="Methyl nitrate">methyl nitrate</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>−O−NO<sub class="template-chem2-sub">2</sub></span>) and <a href="/wiki/Nitroglycerin" title="Nitroglycerin">nitroglycerin</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH(−O−NO<sub class="template-chem2-sub">2</sub>)(−CH<sub class="template-chem2-sub">2</sub>−O−NO<sub class="template-chem2-sub">2</sub>)<sub class="template-chem2-sub">2</sub></span>)</li> <li><a href="/wiki/Phosphoric_acid" title="Phosphoric acid">Phosphoric acid</a> forms <a href="/wiki/Phosphate_ester" class="mw-redirect" title="Phosphate ester">phosphate esters</a>, e.g. <a href="/wiki/Triphenyl_phosphate" title="Triphenyl phosphate">triphenyl phosphate</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">O=P(−O−C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">5</sub>)<sub class="template-chem2-sub">3</sub></span>) and <a href="/w/index.php?title=Methyl_dihydrogen_phosphate&action=edit&redlink=1" class="new" title="Methyl dihydrogen phosphate (page does not exist)">methyl dihydrogen phosphate</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">O=P(−O−CH<sub class="template-chem2-sub">3</sub>)(−OH)<sub class="template-chem2-sub">2</sub></span>) <ul><li><a href="/wiki/Pyrophosphoric_acid" title="Pyrophosphoric acid">Pyrophosphoric (diphosphoric) acid</a> forms <a href="/wiki/Pyrophosphate" title="Pyrophosphate">pyrophosphate</a> esters, e.g. <a href="/wiki/Tetraethyl_pyrophosphate" title="Tetraethyl pyrophosphate">tetraethyl pyrophosphate</a>, <a href="/wiki/Adenosine_diphosphate" title="Adenosine diphosphate">ADP</a>, <a href="/wiki/DADP" class="mw-redirect" title="DADP">dADP</a>, <a href="/wiki/ADPR" class="mw-redirect" title="ADPR">ADPR</a>, <a href="/wiki/CADPR" class="mw-redirect" title="CADPR">cADPR</a>, <a href="/wiki/Cytidine_diphosphate" title="Cytidine diphosphate">CDP</a>, <a href="/wiki/DCDP" class="mw-redirect" title="DCDP">dCDP</a>, <a href="/wiki/Guanosine_diphosphate" title="Guanosine diphosphate">GDP</a>, <a href="/wiki/Deoxyguanosine_diphosphate" title="Deoxyguanosine diphosphate">dGDP</a>, <a href="/wiki/Uridine_diphosphate" title="Uridine diphosphate">UDP</a>, <a href="/wiki/DTDP" class="mw-redirect" title="DTDP">dTDP</a>, <a href="/wiki/MEcPP" class="mw-redirect" title="MEcPP">MEcPP</a>, <a href="/wiki/HMBPP" class="mw-redirect" title="HMBPP">HMBPP</a>, <a href="/wiki/DMAPP" class="mw-redirect" title="DMAPP">DMAPP</a>, <a href="/wiki/Isopentenyl_pyrophosphate" title="Isopentenyl pyrophosphate">IPP</a>, <a href="/wiki/Geranyl_pyrophosphate" title="Geranyl pyrophosphate">GPP</a>, <a href="/wiki/Farnesyl_pyrophosphate" title="Farnesyl pyrophosphate">FPP</a>, <a href="/wiki/Geranylgeranyl_pyrophosphate" title="Geranylgeranyl pyrophosphate">GGPP</a>, <a href="/wiki/ThDP" class="mw-redirect" title="ThDP">ThDP</a>, <a href="/wiki/FAD" class="mw-redirect" title="FAD">FAD</a>, <a href="/wiki/Nicotinamide_adenine_dinucleotide" title="Nicotinamide adenine dinucleotide">NAD</a>, <a href="/wiki/NADP" class="mw-redirect" title="NADP">NADP</a>.</li> <li><a href="/wiki/Triphosphoric_acid" title="Triphosphoric acid">Triphosphoric acid</a> forms <a href="/wiki/Triphosphate" class="mw-redirect" title="Triphosphate">triphosphate</a> esters, e.g. <a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate">ATP</a>, <a href="/wiki/DATP" class="mw-redirect" title="DATP">dATP</a>, <a href="/wiki/Cytidine_triphosphate" title="Cytidine triphosphate">CTP</a>, <a href="/wiki/DCTP" class="mw-redirect" title="DCTP">dCTP</a>, <a href="/wiki/Guanosine_triphosphate" title="Guanosine triphosphate">GTP</a>, <a href="/wiki/DGTP" class="mw-redirect" title="DGTP">dGTP</a>, <a href="/wiki/Uridine_triphosphate" title="Uridine triphosphate">UTP</a>, <a href="/wiki/DTTP" class="mw-redirect" title="DTTP">dTTP</a>, <a href="/wiki/Inosine_triphosphate" title="Inosine triphosphate">ITP</a>, <a href="/wiki/Xanthosine_triphosphate" title="Xanthosine triphosphate">XTP</a>, <a href="/wiki/ThTP" class="mw-redirect" title="ThTP">ThTP</a>, <a href="/wiki/AThTP" class="mw-redirect" title="AThTP">AThTP</a>.</li></ul></li> <li><a href="/wiki/Carbonic_acid" title="Carbonic acid">Carbonic acid</a> forms <a href="/wiki/Carbonate_ester" title="Carbonate ester">carbonate esters</a>, e.g. <a href="/wiki/Dimethyl_carbonate" title="Dimethyl carbonate">dimethyl carbonate</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">(CH<sub class="template-chem2-sub">3</sub>−O−)<sub class="template-chem2-sub">2</sub>C=O</span>) and 5-membered <a href="/wiki/Cyclic_compound" title="Cyclic compound">cyclic</a> <a href="/wiki/Ethylene_carbonate" title="Ethylene carbonate">ethylene carbonate</a> (<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">2</sub>C=O</span>) (if one classifies carbonic acid as an inorganic compound)</li> <li><a href="/wiki/Thiocarbonic_acid" title="Thiocarbonic acid">Trithiocarbonic acid</a> forms <a href="/wiki/Thiocarbonate" title="Thiocarbonate">trithiocarbonate esters</a>, e.g. <a href="/wiki/Dimethyl_trithiocarbonate" title="Dimethyl trithiocarbonate">dimethyl trithiocarbonate</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">(CH<sub class="template-chem2-sub">3</sub>−S−)<sub class="template-chem2-sub">2</sub>C=S</span>) (if one classifies trithiocarbonic acid as an inorganic compound)</li> <li><a href="/wiki/Chloroformic_acid" title="Chloroformic acid">Chloroformic acid</a> forms <a href="/wiki/Chloroformate" title="Chloroformate">chloroformate</a> esters, e.g. <a href="/wiki/Methyl_chloroformate" title="Methyl chloroformate">methyl chloroformate</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Cl−C(=O)−O−CH<sub class="template-chem2-sub">3</sub></span>) (if one classifies chloroformic acid as an inorganic compound)</li> <li><a href="/wiki/Boric_acid" title="Boric acid">Boric acid</a> forms <a href="/wiki/Borate#Borate_esters" title="Borate">borate esters</a>, e.g. <a href="/wiki/Trimethyl_borate" title="Trimethyl borate">trimethyl borate</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">B(−O−CH<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">3</sub></span>)</li> <li><a href="/wiki/Chromic_acid" title="Chromic acid">Chromic acid</a> forms <a href="/wiki/Di-tert-butyl_chromate" title="Di-tert-butyl chromate">di-<i>tert</i>-butyl chromate</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">((CH<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">3</sub>C−O−)<sub class="template-chem2-sub">2</sub>Cr(=O)<sub class="template-chem2-sub">2</sub></span>)</li></ul> <p>Inorganic acids that exist as <a href="/wiki/Tautomers" class="mw-redirect" title="Tautomers">tautomers</a> form two or more types of esters. </p> <ul><li><a href="/wiki/Thiosulfuric_acid" title="Thiosulfuric acid">Thiosulfuric acid</a> forms two types of <a href="/wiki/Thiosulfate" title="Thiosulfate">thiosulfate</a> esters, e.g. <i>O</i>,<i>O</i>-dimethyl thiosulfate (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">(CH<sub class="template-chem2-sub">3</sub>−O−)<sub class="template-chem2-sub">2</sub>S(=O)(=S)</span>) and <i>O</i>,<i>S</i>-dimethyl thiosulfate (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">(CH<sub class="template-chem2-sub">3</sub>−O−)(CH<sub class="template-chem2-sub">3</sub>−S−)S(=O)<sub class="template-chem2-sub">2</sub></span>)</li> <li><a href="/wiki/Thiocyanic_acid" title="Thiocyanic acid">Thiocyanic acid</a> forms <a href="/wiki/Thiocyanate" title="Thiocyanate">thiocyanate</a> esters, e.g. <a href="/wiki/Methyl_thiocyanate" title="Methyl thiocyanate">methyl thiocyanate</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>−S−C≡N</span>) (if one classifies thiocyanic acid as an inorganic compound), but forms <a href="/wiki/Isothiocyanate" title="Isothiocyanate">isothiocyanate</a> "esters" as well, e.g. <a href="/wiki/Methyl_isothiocyanate" title="Methyl isothiocyanate">methyl isothiocyanate</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>−N=C=S</span>), although <a href="/wiki/Organyl" class="mw-redirect" title="Organyl">organyl</a> isothiocyanates are not classified as esters by the <a href="/wiki/IUPAC" class="mw-redirect" title="IUPAC">IUPAC</a></li> <li><a href="/wiki/Phosphorous_acid" title="Phosphorous acid">Phosphorous acid</a> forms two types of esters: <a href="/wiki/Phosphite_ester" title="Phosphite ester">phosphite esters</a>, e.g. <a href="/wiki/Triethyl_phosphite" title="Triethyl phosphite">triethyl phosphite</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">P(−O−CH<sub class="template-chem2-sub">2</sub>CH<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">3</sub></span>), and <a href="/wiki/Phosphonate" title="Phosphonate">phosphonate esters</a>, e.g. <a href="/wiki/Diethyl_phosphite" class="mw-redirect" title="Diethyl phosphite">diethyl phosphonate</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">H−P(=O)(−O−CH<sub class="template-chem2-sub">2</sub>CH<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">2</sub></span>)</li></ul> <p>Some inorganic acids that are unstable or elusive form stable esters. </p> <ul><li><a href="/wiki/Sulfurous_acid" title="Sulfurous acid">Sulfurous acid</a>, which is unstable, forms stable <a href="/wiki/Dimethyl_sulfite" title="Dimethyl sulfite">dimethyl sulfite</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">(CH<sub class="template-chem2-sub">3</sub>−O−)<sub class="template-chem2-sub">2</sub>S=O</span>)</li> <li><a href="/wiki/Dicarbonic_acid" class="mw-redirect" title="Dicarbonic acid">Dicarbonic acid</a>, which is unstable, forms stable <a href="/wiki/Dimethyl_dicarbonate" title="Dimethyl dicarbonate">dimethyl dicarbonate</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>−O−C(=O)−O−C(=O)−O−CH<sub class="template-chem2-sub">3</sub></span>)</li></ul> <p>In principle, a part of metal and metalloid <a href="/wiki/Alkoxide" title="Alkoxide">alkoxides</a>, of which many hundreds are known, could be classified as esters of the corresponding acids (e.g. <a href="/wiki/Aluminium_triethoxide" class="mw-redirect" title="Aluminium triethoxide">aluminium triethoxide</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Al(OCH<sub class="template-chem2-sub">2</sub>CH<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">3</sub></span>) could be classified as an ester of aluminic acid which is <a href="/wiki/Aluminium_hydroxide" title="Aluminium hydroxide">aluminium hydroxide</a>, <a href="/wiki/Tetraethyl_orthosilicate" title="Tetraethyl orthosilicate">tetraethyl orthosilicate</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Si(OCH<sub class="template-chem2-sub">2</sub>CH<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">4</sub></span>) could be classified as an ester of <a href="/wiki/Orthosilicic_acid" title="Orthosilicic acid">orthosilicic acid</a>, and <a href="/wiki/Titanium_ethoxide" title="Titanium ethoxide">titanium ethoxide</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Ti(OCH<sub class="template-chem2-sub">2</sub>CH<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">4</sub></span>) could be classified as an ester of <a href="/wiki/Titanic_acid" title="Titanic acid">orthotitanic acid</a>). </p> <div class="mw-heading mw-heading2"><h2 id="Structure_and_bonding">Structure and bonding</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ester&action=edit&section=6" title="Edit section: Structure and bonding"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Esters derived from <a href="/wiki/Carboxylic_acids" class="mw-redirect" title="Carboxylic acids">carboxylic acids</a> and <a href="/wiki/Alcohols" class="mw-redirect" title="Alcohols">alcohols</a> contain a <a href="/wiki/Carbonyl" class="mw-redirect" title="Carbonyl">carbonyl</a> group C=O, which is a <a href="/wiki/Divalent" class="mw-redirect" title="Divalent">divalent</a> group at <a href="/wiki/Carbon" title="Carbon">C</a> atom, which gives rise to 120° C–C–O and O–C–O angles. Unlike <a href="/wiki/Amide" title="Amide">amides</a>, carboxylic acid esters are structurally flexible functional groups because rotation about the C–O–C bonds has a low barrier. Their flexibility and low polarity is manifested in their physical properties; they tend to be less rigid (lower melting point) and more volatile (lower boiling point) than the corresponding <a href="/wiki/Amides" class="mw-redirect" title="Amides">amides</a>.<sup id="cite_ref-March_7-0" class="reference"><a href="#cite_note-March-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> The <a href="/wiki/Acid_dissociation_constant" title="Acid dissociation constant">p<i>K</i><sub>a</sub></a> of the alpha-hydrogens on esters of carboxylic acids is around 25 (alpha-hydrogen is a hydrogen bound to the carbon adjacent to the <a href="/wiki/Carbonyl_group" title="Carbonyl group">carbonyl group</a> (C=O) of carboxylate esters).<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p><p>Many carboxylic acid esters have the potential for <a href="/wiki/Conformational_isomerism" title="Conformational isomerism">conformational isomerism</a>, but they tend to adopt an <i>S</i>-<i>cis</i> (or <i>Z</i>) conformation rather than the <i>S</i>-<i>trans</i> (or <i>E</i>) alternative, due to a combination of <a href="/wiki/Anomeric_effect#Dipole_Minimization" title="Anomeric effect">hyperconjugation and dipole minimization</a> effects. The preference for the <i>Z</i> conformation is influenced by the nature of the substituents and solvent, if present.<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Lactone" title="Lactone">Lactones</a> with small rings are restricted to the <i>s</i>-trans (i.e. <i>E</i>) conformation due to their cyclic structure. </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Ester_conformers.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6a/Ester_conformers.png/300px-Ester_conformers.png" decoding="async" width="300" height="116" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6a/Ester_conformers.png/450px-Ester_conformers.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6a/Ester_conformers.png/600px-Ester_conformers.png 2x" data-file-width="832" data-file-height="322" /></a><figcaption></figcaption></figure> <figure class="mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:PhCO2MeStructure.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/8c/PhCO2MeStructure.png/144px-PhCO2MeStructure.png" decoding="async" width="144" height="163" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/8c/PhCO2MeStructure.png/216px-PhCO2MeStructure.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/8c/PhCO2MeStructure.png/288px-PhCO2MeStructure.png 2x" data-file-width="518" data-file-height="587" /></a><figcaption>Metrical details for <a href="/wiki/Methyl_benzoate" title="Methyl benzoate">methyl benzoate</a>, distances in picometers.<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></figcaption></figure> <div class="mw-heading mw-heading2"><h2 id="Physical_properties_and_characterization">Physical properties and characterization</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ester&action=edit&section=7" title="Edit section: Physical properties and characterization"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Esters derived from <a href="/wiki/Carboxylic_acid" title="Carboxylic acid">carboxylic acids</a> and alcohols are more polar than <a href="/wiki/Ethers" class="mw-redirect" title="Ethers">ethers</a> but less polar than alcohols. They participate in <a href="/wiki/Hydrogen_bond" title="Hydrogen bond">hydrogen bonds</a> as hydrogen-bond acceptors, but cannot act as hydrogen-bond donors, unlike their parent alcohols. This ability to participate in hydrogen bonding confers some water-solubility. Because of their lack of hydrogen-bond-donating ability, esters do not self-associate. Consequently, esters are more volatile than carboxylic acids of similar molecular weight.<sup id="cite_ref-March_7-1" class="reference"><a href="#cite_note-March-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Characterization_and_analysis">Characterization and analysis</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ester&action=edit&section=8" title="Edit section: Characterization and analysis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Esters are generally identified by gas chromatography, taking advantage of their volatility. <a href="/wiki/IR_spectroscopy" class="mw-redirect" title="IR spectroscopy">IR spectra</a> for esters feature an intense sharp band in the range 1730–1750 cm<sup>−1</sup> assigned to <i>ν</i><sub>C=O</sub>. This peak changes depending on the functional groups attached to the carbonyl. For example, a benzene ring or double bond in conjunction with the carbonyl will bring the wavenumber down about 30 cm<sup>−1</sup>. </p> <div class="mw-heading mw-heading2"><h2 id="Applications_and_occurrence">Applications and occurrence</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ester&action=edit&section=9" title="Edit section: Applications and occurrence"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Esters are widespread in nature and are widely used in industry. In nature, <a href="/wiki/Fat" title="Fat">fats</a> are, in general, triesters derived from <a href="/wiki/Glycerol" title="Glycerol">glycerol</a> and <a href="/wiki/Fatty_acid" title="Fatty acid">fatty acids</a>.<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> Esters are responsible for the aroma of many fruits, including <a href="/wiki/Apple" title="Apple">apples</a>, <a href="/wiki/Durian" title="Durian">durians</a>, <a href="/wiki/Pear" title="Pear">pears</a>, <a href="/wiki/Banana" title="Banana">bananas</a>, <a href="/wiki/Pineapple" title="Pineapple">pineapples</a>, and <a href="/wiki/Strawberry" title="Strawberry">strawberries</a>.<sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> Several billion kilograms of <a href="/wiki/Polyester" title="Polyester">polyesters</a> are produced industrially annually, important products being <a href="/wiki/Polyethylene_terephthalate" title="Polyethylene terephthalate">polyethylene terephthalate</a>, <a href="/wiki/Acrylate_ester" class="mw-redirect" title="Acrylate ester">acrylate esters</a>, and <a href="/wiki/Cellulose_acetate" title="Cellulose acetate">cellulose acetate</a>.<sup id="cite_ref-Ullmann_14-0" class="reference"><a href="#cite_note-Ullmann-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Triglyceride_unsaturated_Structural_Formulae_V2.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/85/Triglyceride_unsaturated_Structural_Formulae_V2.svg/450px-Triglyceride_unsaturated_Structural_Formulae_V2.svg.png" decoding="async" width="450" height="236" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/85/Triglyceride_unsaturated_Structural_Formulae_V2.svg/675px-Triglyceride_unsaturated_Structural_Formulae_V2.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/85/Triglyceride_unsaturated_Structural_Formulae_V2.svg/900px-Triglyceride_unsaturated_Structural_Formulae_V2.svg.png 2x" data-file-width="512" data-file-height="269" /></a><figcaption>Representative <a href="/wiki/Triglyceride" title="Triglyceride">triglyceride</a> found in a linseed oil, a triester of <a href="/wiki/Glycerol" title="Glycerol"><span style="color:black;"><b>glycerol</b></span></a> (center, black) derived of <a href="/wiki/Linoleic_acid" title="Linoleic acid"><span style="color:green;"><b>linoleic acid</b></span></a> (bottom right, green), <a href="/wiki/Alpha-linolenic_acid" class="mw-redirect" title="Alpha-linolenic acid"><span style="color:red;"><b>alpha-linolenic acid</b></span></a> (left, red), and <a href="/wiki/Oleic_acid" title="Oleic acid"><span style="color:blue;"><b>oleic acid</b></span></a> (top right, blue).</figcaption></figure></dd></dl> <div class="mw-heading mw-heading2"><h2 id="Preparation">Preparation</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ester&action=edit&section=10" title="Edit section: Preparation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Esterification is the general name for a <a href="/wiki/Chemical_reaction" title="Chemical reaction">chemical reaction</a> in which two reactants (typically an alcohol and an acid) form an ester as the <a href="/wiki/Product_(chemistry)" title="Product (chemistry)">reaction product</a>. Esters are common in organic chemistry and biological materials, and often have a pleasant characteristic, fruity odor. This leads to their extensive use in the <a href="/wiki/Fragrance" class="mw-redirect" title="Fragrance">fragrance</a> and <a href="/wiki/Flavoring" title="Flavoring">flavor</a> industry. Ester bonds are also found in many <a href="/wiki/Polymer" title="Polymer">polymers</a>. </p> <div class="mw-heading mw-heading3"><h3 id="Esterification_of_carboxylic_acids_with_alcohols">Esterification of carboxylic acids with alcohols</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ester&action=edit&section=11" title="Edit section: Esterification of carboxylic acids with alcohols"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The classic synthesis is the <a href="/wiki/Fischer_esterification" class="mw-redirect" title="Fischer esterification">Fischer esterification</a>, which involves treating a carboxylic acid with an alcohol in the presence of a <a href="/wiki/Dehydration_reaction" title="Dehydration reaction">dehydrating</a> agent: </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">RCO<sub class="template-chem2-sub">2</sub>H + R'OH ⇌ RCO<sub class="template-chem2-sub">2</sub>R' + H<sub class="template-chem2-sub">2</sub>O</span></dd></dl> <p>The equilibrium constant for such reactions is about 5 for typical esters, e.g., ethyl acetate.<sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> The reaction is slow in the absence of a catalyst. <a href="/wiki/Sulfuric_acid" title="Sulfuric acid">Sulfuric acid</a> is a typical catalyst for this reaction. Many other acids are also used such as <a href="/wiki/Dowex" class="mw-redirect" title="Dowex">polymeric sulfonic acids</a>. Since esterification is highly reversible, the yield of the ester can be improved using <a href="/wiki/Le_Chatelier%27s_principle" title="Le Chatelier's principle">Le Chatelier's principle</a>: </p> <ul><li>Using the alcohol in large excess (i.e., as a solvent).</li> <li>Using a dehydrating agent: sulfuric acid not only catalyzes the reaction but sequesters water (a reaction product). Other drying agents such as <a href="/wiki/Molecular_sieves" class="mw-redirect" title="Molecular sieves">molecular sieves</a> are also effective.</li> <li>Removal of water by physical means such as <a href="/wiki/Distillation" title="Distillation">distillation</a> as a low-boiling <a href="/wiki/Azeotrope" title="Azeotrope">azeotrope</a> with <a href="/wiki/Toluene" title="Toluene">toluene</a>, in conjunction with a <a href="/wiki/Dean-Stark_apparatus" class="mw-redirect" title="Dean-Stark apparatus">Dean-Stark apparatus</a>.</li></ul> <p>Reagents are known that drive the dehydration of mixtures of alcohols and carboxylic acids. One example is the <a href="/wiki/Steglich_esterification" title="Steglich esterification">Steglich esterification</a>, which is a method of forming esters under mild conditions. The method is popular in <a href="/wiki/Peptide_synthesis" title="Peptide synthesis">peptide synthesis</a>, where the substrates are sensitive to harsh conditions like high heat. DCC (<a href="/wiki/Dicyclohexylcarbodiimide" class="mw-redirect" title="Dicyclohexylcarbodiimide">dicyclohexylcarbodiimide</a>) is used to activate the carboxylic acid to further reaction. <a href="/wiki/4-Dimethylaminopyridine" title="4-Dimethylaminopyridine">4-Dimethylaminopyridine</a> (DMAP) is used as an acyl-transfer <a href="/wiki/Catalyst" class="mw-redirect" title="Catalyst">catalyst</a>.<sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><span typeof="mw:File"><a href="/wiki/File:Steglich-1.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/86/Steglich-1.svg/300px-Steglich-1.svg.png" decoding="async" width="300" height="88" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/86/Steglich-1.svg/450px-Steglich-1.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/86/Steglich-1.svg/600px-Steglich-1.svg.png 2x" data-file-width="539" data-file-height="159" /></a></span></dd></dl> <p>Another method for the dehydration of mixtures of alcohols and carboxylic acids is the <a href="/wiki/Mitsunobu_reaction" title="Mitsunobu reaction">Mitsunobu reaction</a>: </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">RCO<sub class="template-chem2-sub">2</sub>H + R'OH + P(C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">5</sub>)<sub class="template-chem2-sub">3</sub> + R<sub class="template-chem2-sub">2</sub>N<sub class="template-chem2-sub">2</sub> → RCO<sub class="template-chem2-sub">2</sub>R' + OP(C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">5</sub>)<sub class="template-chem2-sub">3</sub> + R<sub class="template-chem2-sub">2</sub>N<sub class="template-chem2-sub">2</sub>H<sub class="template-chem2-sub">2</sub></span></dd></dl> <p>Carboxylic acids can be esterified using <a href="/wiki/Diazomethane" title="Diazomethane">diazomethane</a>: </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">RCO<sub class="template-chem2-sub">2</sub>H + CH<sub class="template-chem2-sub">2</sub>N<sub class="template-chem2-sub">2</sub> → RCO<sub class="template-chem2-sub">2</sub>CH<sub class="template-chem2-sub">3</sub> + N<sub class="template-chem2-sub">2</sub></span></dd></dl> <p>Using this diazomethane, mixtures of carboxylic acids can be converted to their methyl esters in near quantitative yields, e.g., for analysis by <a href="/wiki/Gas_chromatography" title="Gas chromatography">gas chromatography</a>. The method is useful in specialized organic synthetic operations but is considered too hazardous and expensive for large-scale applications. </p> <div class="mw-heading mw-heading3"><h3 id="Esterification_of_carboxylic_acids_with_epoxides">Esterification of carboxylic acids with epoxides</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ester&action=edit&section=12" title="Edit section: Esterification of carboxylic acids with epoxides"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Carboxylic acids are esterified by treatment with <a href="/wiki/Epoxides" class="mw-redirect" title="Epoxides">epoxides</a>, giving β-hydroxyesters: </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">RCO<sub class="template-chem2-sub">2</sub>H + RCHCH<sub class="template-chem2-sub">2</sub>O → RCO<sub class="template-chem2-sub">2</sub>CH<sub class="template-chem2-sub">2</sub>CH(OH)R</span></dd></dl> <p>This reaction is employed in the production of <a href="/wiki/Vinyl_ester_resin" title="Vinyl ester resin">vinyl ester resin</a> from <a href="/wiki/Acrylic_acid" title="Acrylic acid">acrylic acid</a>. </p> <div class="mw-heading mw-heading3"><h3 id="Alcoholysis_of_acyl_chlorides_and_acid_anhydrides">Alcoholysis of acyl chlorides and acid anhydrides</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ester&action=edit&section=13" title="Edit section: Alcoholysis of acyl chlorides and acid anhydrides"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Alcohols react with <a href="/wiki/Acyl_chloride" title="Acyl chloride">acyl chlorides</a> and <a href="/wiki/Acid_anhydride" title="Acid anhydride">acid anhydrides</a> to give esters: </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">RCOCl + R'OH → RCO<sub class="template-chem2-sub">2</sub>R' + HCl</span></dd> <dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">(RCO)<sub class="template-chem2-sub">2</sub>O + R'OH → RCO<sub class="template-chem2-sub">2</sub>R' + RCO<sub class="template-chem2-sub">2</sub>H</span></dd></dl> <p>The reactions are irreversible simplifying <a href="/wiki/Work-up_(chemistry)" class="mw-redirect" title="Work-up (chemistry)">work-up</a>. Since acyl chlorides and acid anhydrides also react with water, anhydrous conditions are preferred. The analogous acylations of amines to give <a href="/wiki/Amide" title="Amide">amides</a> are less sensitive because amines are stronger <a href="/wiki/Nucleophile" title="Nucleophile">nucleophiles</a> and react more rapidly than does water. This method is employed only for laboratory-scale procedures, as it is expensive. </p> <div class="mw-heading mw-heading3"><h3 id="Alkylation_of_carboxylic_acids_and_their_salts">Alkylation of carboxylic acids and their salts</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ester&action=edit&section=14" title="Edit section: Alkylation of carboxylic acids and their salts"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Trimethyloxonium_tetrafluoroborate" title="Trimethyloxonium tetrafluoroborate">Trimethyloxonium tetrafluoroborate</a> can be used for <a href="/wiki/Esterification" class="mw-redirect" title="Esterification">esterification</a> of carboxylic acids under conditions where acid-catalyzed reactions are infeasible:<sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">RCO<sub class="template-chem2-sub">2</sub>H + (CH<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">3</sub>OBF<sub class="template-chem2-sub">4</sub> → RCO<sub class="template-chem2-sub">2</sub>CH<sub class="template-chem2-sub">3</sub> + (CH<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">2</sub>O + HBF<sub class="template-chem2-sub">4</sub></span></dd></dl> <p>Although rarely employed for esterifications, carboxylate salts (often generated <i>in situ</i>) react with <a href="/wiki/Electrophilic" class="mw-redirect" title="Electrophilic">electrophilic</a> <a href="/wiki/Alkylating_agent" class="mw-redirect" title="Alkylating agent">alkylating agents</a>, such as <a href="/wiki/Alkyl_halide" class="mw-redirect" title="Alkyl halide">alkyl halides</a>, to give esters.<sup id="cite_ref-Ullmann_14-1" class="reference"><a href="#cite_note-Ullmann-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-18" class="reference"><a href="#cite_note-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> Anion availability can inhibit this reaction, which correspondingly benefits from <a href="/wiki/Phase_transfer_catalyst" class="mw-redirect" title="Phase transfer catalyst">phase transfer catalysts</a> or such highly polar <a href="/wiki/Aprotic_solvent" class="mw-redirect" title="Aprotic solvent">aprotic solvents</a> as <a href="/wiki/Dimethylformamide" title="Dimethylformamide">DMF</a>. An additional iodide salt may, via the <a href="/wiki/Finkelstein_reaction" title="Finkelstein reaction">Finkelstein reaction</a>, catalyze the reaction of a recalcitrant alkyl halide. Alternatively, salts of a coordinating metal, such as silver, may improve the reaction rate by easing halide elimination. </p> <div class="mw-heading mw-heading3"><h3 id="Transesterification">Transesterification</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ester&action=edit&section=15" title="Edit section: Transesterification"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Transesterification" title="Transesterification">Transesterification</a>, which involves changing one ester into another one, is widely practiced: </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">RCO<sub class="template-chem2-sub">2</sub>R' + CH<sub class="template-chem2-sub">3</sub>OH → RCO<sub class="template-chem2-sub">2</sub>CH<sub class="template-chem2-sub">3</sub> + R'OH</span></dd></dl> <p>Like the hydrolysation, transesterification is catalysed by acids and bases. The reaction is widely used for degrading <a href="/wiki/Triglyceride" title="Triglyceride">triglycerides</a>, e.g. in the production of fatty acid esters and alcohols. <a href="/wiki/Poly(ethylene_terephthalate)" class="mw-redirect" title="Poly(ethylene terephthalate)">Poly(ethylene terephthalate)</a> is produced by the transesterification of <a href="/wiki/Dimethyl_terephthalate" title="Dimethyl terephthalate">dimethyl terephthalate</a> and ethylene glycol:<sup id="cite_ref-Ullmann_14-2" class="reference"><a href="#cite_note-Ullmann-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap"><i>n</i> (C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">4</sub>)(CO<sub class="template-chem2-sub">2</sub>CH<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">2</sub> + 2<i>n</i> C<sub class="template-chem2-sub">2</sub>H<sub class="template-chem2-sub">4</sub>(OH)<sub class="template-chem2-sub">2</sub> → [(C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">4</sub>)(CO<sub class="template-chem2-sub">2</sub>)<sub class="template-chem2-sub">2</sub>(C<sub class="template-chem2-sub">2</sub>H<sub class="template-chem2-sub">4</sub>)]<sub class="template-chem2-sub"><i>n</i></sub> + 2<i>n</i> CH<sub class="template-chem2-sub">3</sub>OH</span></dd></dl> <p>A subset of transesterification is the alcoholysis of <a href="/wiki/Diketene" title="Diketene">diketene</a>. This reaction affords 2-ketoesters.<sup id="cite_ref-Ullmann_14-3" class="reference"><a href="#cite_note-Ullmann-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">(CH<sub class="template-chem2-sub">2</sub>CO)<sub class="template-chem2-sub">2</sub> + ROH → CH<sub class="template-chem2-sub">3</sub>C(O)CH<sub class="template-chem2-sub">2</sub>CO<sub class="template-chem2-sub">2</sub>R</span></dd></dl> <div class="mw-heading mw-heading3"><h3 id="Carbonylation">Carbonylation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ester&action=edit&section=16" title="Edit section: Carbonylation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Alkenes undergo <a href="/wiki/Carboalkoxylation" title="Carboalkoxylation">carboalkoxylation</a> in the presence of <a href="/wiki/Metal_carbonyl" title="Metal carbonyl">metal carbonyl</a> catalysts. Esters of <a href="/wiki/Propanoic_acid" class="mw-redirect" title="Propanoic acid">propanoic acid</a> are produced commercially by this method: </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">H<sub class="template-chem2-sub">2</sub>C=CH<sub class="template-chem2-sub">2</sub> + ROH + CO → CH<sub class="template-chem2-sub">3</sub>CH<sub class="template-chem2-sub">2</sub>CO<sub class="template-chem2-sub">2</sub>R</span></dd></dl> <p>A preparation of <a href="/wiki/Methyl_propionate" title="Methyl propionate">methyl propionate</a> is one illustrative example. </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">H<sub class="template-chem2-sub">2</sub>C=CH<sub class="template-chem2-sub">2</sub> + CO + CH<sub class="template-chem2-sub">3</sub>OH → CH<sub class="template-chem2-sub">3</sub>CH<sub class="template-chem2-sub">2</sub>CO<sub class="template-chem2-sub">2</sub>CH<sub class="template-chem2-sub">3</sub></span></dd></dl> <p>The carbonylation of <a href="/wiki/Methanol" title="Methanol">methanol</a> yields <a href="/wiki/Methyl_formate" title="Methyl formate">methyl formate</a>, which is the main commercial source of <a href="/wiki/Formic_acid" title="Formic acid">formic acid</a>. The reaction is catalyzed by <a href="/wiki/Sodium_methoxide" title="Sodium methoxide">sodium methoxide</a>: </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>OH + CO → HCO<sub class="template-chem2-sub">2</sub>CH<sub class="template-chem2-sub">3</sub></span></dd></dl> <div class="mw-heading mw-heading3"><h3 id="Addition_of_carboxylic_acids_to_alkenes_and_alkynes">Addition of carboxylic acids to alkenes and alkynes</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ester&action=edit&section=17" title="Edit section: Addition of carboxylic acids to alkenes and alkynes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In <a href="/wiki/Hydroesterification" class="mw-redirect" title="Hydroesterification">hydroesterification</a>, alkenes and alkynes insert into the <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">O−H</span> bond of carboxylic acids. <a href="/wiki/Vinyl_acetate" title="Vinyl acetate">Vinyl acetate</a> is produced industrially by the addition of acetic acid to <a href="/wiki/Acetylene" title="Acetylene">acetylene</a> in the presence of <a href="/wiki/Zinc_acetate" title="Zinc acetate">zinc acetate</a> catalysts:<sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">HC≡CH + CH<sub class="template-chem2-sub">3</sub>CO<sub class="template-chem2-sub">2</sub>H → CH<sub class="template-chem2-sub">3</sub>CO<sub class="template-chem2-sub">2</sub>CH=CH<sub class="template-chem2-sub">2</sub></span></dd></dl> <p><a href="/wiki/Vinyl_acetate" title="Vinyl acetate">Vinyl acetate</a> can also be produced by <a href="/wiki/Palladium" title="Palladium">palladium</a>-catalyzed reaction of ethylene, <a href="/wiki/Acetic_acid" title="Acetic acid">acetic acid</a>, and <a href="/wiki/Oxygen" title="Oxygen">oxygen</a>: </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">2 H<sub class="template-chem2-sub">2</sub>C=CH<sub class="template-chem2-sub">2</sub> + 2 CH<sub class="template-chem2-sub">3</sub>CO<sub class="template-chem2-sub">2</sub>H + O<sub class="template-chem2-sub">2</sub> → 2 CH<sub class="template-chem2-sub">3</sub>CO<sub class="template-chem2-sub">2</sub>CH=CH<sub class="template-chem2-sub">2</sub> + 2 H<sub class="template-chem2-sub">2</sub>O</span></dd></dl> <p><a href="/wiki/Silicotungstic_acid" title="Silicotungstic acid">Silicotungstic acid</a> is used to manufacture <a href="/wiki/Ethyl_acetate" title="Ethyl acetate">ethyl acetate</a> by the <a href="/wiki/Alkylation" title="Alkylation">alkylation</a> of <a href="/wiki/Acetic_acid" title="Acetic acid">acetic acid</a> by ethylene: </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">H<sub class="template-chem2-sub">2</sub>C=CH<sub class="template-chem2-sub">2</sub> + CH<sub class="template-chem2-sub">3</sub>CO<sub class="template-chem2-sub">2</sub>H → CH<sub class="template-chem2-sub">3</sub>CO<sub class="template-chem2-sub">2</sub>CH<sub class="template-chem2-sub">2</sub>CH<sub class="template-chem2-sub">3</sub></span></dd></dl> <div class="mw-heading mw-heading3"><h3 id="From_aldehydes">From aldehydes</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ester&action=edit&section=18" title="Edit section: From aldehydes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The <a href="/wiki/Tishchenko_reaction" title="Tishchenko reaction">Tishchenko reaction</a> involves <a href="/wiki/Disproportionation" title="Disproportionation">disproportionation</a> of an <a href="/wiki/Aldehyde" title="Aldehyde">aldehyde</a> in the presence of an anhydrous base to give an ester. <a href="/wiki/Catalyst" class="mw-redirect" title="Catalyst">Catalysts</a> are aluminium alkoxides or sodium alkoxides. <a href="/wiki/Benzaldehyde" title="Benzaldehyde">Benzaldehyde</a> reacts with sodium benzyloxide (generated from <a href="/wiki/Sodium" title="Sodium">sodium</a> and <a href="/wiki/Benzyl_alcohol" title="Benzyl alcohol">benzyl alcohol</a>) to generate <a href="/wiki/Benzyl_benzoate" title="Benzyl benzoate">benzyl benzoate</a>.<sup id="cite_ref-kamm_20-0" class="reference"><a href="#cite_note-kamm-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> The method is used in the production of <a href="/wiki/Ethyl_acetate" title="Ethyl acetate">ethyl acetate</a> from <a href="/wiki/Acetaldehyde" title="Acetaldehyde">acetaldehyde</a>.<sup id="cite_ref-Ullmann_14-4" class="reference"><a href="#cite_note-Ullmann-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Other_methods">Other methods</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ester&action=edit&section=19" title="Edit section: Other methods"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Favorskii_rearrangement" title="Favorskii rearrangement">Favorskii rearrangement</a> of α-haloketones in presence of base</li> <li><a href="/wiki/Baeyer%E2%80%93Villiger_oxidation" title="Baeyer–Villiger oxidation">Baeyer–Villiger oxidation</a> of ketones with peroxides</li> <li><a href="/wiki/Pinner_reaction" title="Pinner reaction">Pinner reaction</a> of <a href="/wiki/Nitrile" title="Nitrile">nitriles</a> with an alcohol</li> <li><a href="/wiki/Nucleophilic_abstraction" title="Nucleophilic abstraction">Nucleophilic abstraction</a> of a metal–acyl complex</li> <li>Hydrolysis of <a href="/wiki/Orthoesters" class="mw-redirect" title="Orthoesters">orthoesters</a> in aqueous acid</li> <li>Cellulolysis via esterification<sup id="cite_ref-Synthesis_of_glucose_esters_from_cellulose_in_ionic_liquids_21-0" class="reference"><a href="#cite_note-Synthesis_of_glucose_esters_from_cellulose_in_ionic_liquids-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup></li> <li><a href="/wiki/Ozonolysis" title="Ozonolysis">Ozonolysis</a> of <a href="/wiki/Alkene" title="Alkene">alkenes</a> using a <a href="/wiki/Work-up_(chemistry)" class="mw-redirect" title="Work-up (chemistry)">work up</a> in the presence of <a href="/wiki/Hydrochloric_acid" title="Hydrochloric acid">hydrochloric acid</a> and various <a href="/wiki/Alcohols" class="mw-redirect" title="Alcohols">alcohols</a>.<sup id="cite_ref-22" class="reference"><a href="#cite_note-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup></li> <li><a href="/wiki/Electrosynthesis#Anodic_oxidations" title="Electrosynthesis">Anodic oxidation</a> of <a href="/wiki/Methyl_group" title="Methyl group">methyl</a> <a href="/wiki/Ketones" class="mw-redirect" title="Ketones">ketones</a> leading to methyl esters.<sup id="cite_ref-23" class="reference"><a href="#cite_note-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup></li> <li><a href="/wiki/Fat_interesterification" title="Fat interesterification">Interesterification</a> exchanges the fatty acid groups of different esters.</li></ul> <div class="mw-heading mw-heading2"><h2 id="Reactions">Reactions</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ester&action=edit&section=20" title="Edit section: Reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Esters are less reactive than acid halides and anhydrides. As with more reactive acyl derivatives, they can react with <a href="/wiki/Ammonia" title="Ammonia">ammonia</a> and primary and secondary amines to give amides, although this type of reaction is not often used, since acid halides give better yields. </p> <div class="mw-heading mw-heading3"><h3 id="Transesterification_2">Transesterification</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ester&action=edit&section=21" title="Edit section: Transesterification"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Esters can be converted to other esters in a process known as <a href="/wiki/Transesterification" title="Transesterification">transesterification</a>. Transesterification can be either acid- or base-catalyzed, and involves the reaction of an ester with an alcohol. Unfortunately, because the leaving group is also an alcohol, the forward and reverse reactions will often occur at similar rates. Using a large excess of the <a href="/wiki/Reactant" class="mw-redirect" title="Reactant">reactant</a> alcohol or removing the leaving group alcohol (e.g. via <a href="/wiki/Distillation" title="Distillation">distillation</a>) will drive the forward reaction towards completion, in accordance with <a href="/wiki/Le_Chatelier%27s_principle" title="Le Chatelier's principle">Le Chatelier's principle</a>.<sup id="cite_ref-wade_24-0" class="reference"><a href="#cite_note-wade-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Hydrolysis_and_saponification">Hydrolysis and saponification</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ester&action=edit&section=22" title="Edit section: Hydrolysis and saponification"><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/Ester_hydrolysis" title="Ester hydrolysis">Ester hydrolysis</a></div> <p>Acid-catalyzed hydrolysis of esters is also an equilibrium process – essentially the reverse of the <a href="/wiki/Fischer_esterification" class="mw-redirect" title="Fischer esterification">Fischer esterification</a> reaction. Because an alcohol (which acts as the leaving group) and water (which acts as the nucleophile) have similar p<i>K</i><sub>a</sub> values, the forward and reverse reactions compete with each other. As in transesterification, using a large excess of reactant (water) or removing one of the products (the alcohol) can promote the forward reaction. </p> <figure class="mw-default-size mw-halign-center" typeof="mw:File"><a href="/wiki/File:Fischer_esterification-hydrolysis_equilibrium.svg" class="mw-file-description" title="The acid-catalyzed hydrolysis of an ester and Fischer esterification correspond to two directions of an equilibrium process."><img alt="The acid-catalyzed hydrolysis of an ester and Fischer esterification correspond to two directions of an equilibrium process." src="//upload.wikimedia.org/wikipedia/commons/thumb/e/ed/Fischer_esterification-hydrolysis_equilibrium.svg/824px-Fischer_esterification-hydrolysis_equilibrium.svg.png" decoding="async" width="824" height="226" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/ed/Fischer_esterification-hydrolysis_equilibrium.svg/1236px-Fischer_esterification-hydrolysis_equilibrium.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/ed/Fischer_esterification-hydrolysis_equilibrium.svg/1648px-Fischer_esterification-hydrolysis_equilibrium.svg.png 2x" data-file-width="824" data-file-height="226" /></a><figcaption>The acid-catalyzed hydrolysis of an ester and Fischer esterification correspond to two directions of an equilibrium process.</figcaption></figure> <p>Basic hydrolysis of esters, known as <a href="/wiki/Saponification" title="Saponification">saponification</a>, is not an equilibrium process; a full equivalent of base is consumed in the reaction, which produces one equivalent of alcohol and one equivalent of a carboxylate salt. The saponification of esters of <a href="/wiki/Fatty_acid" title="Fatty acid">fatty acids</a> is an industrially important process, used in the production of soap.<sup id="cite_ref-wade_24-1" class="reference"><a href="#cite_note-wade-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> </p><p>Esterification is a reversible reaction. Esters undergo <a href="/wiki/Hydrolysis" title="Hydrolysis">hydrolysis</a> under acidic and basic conditions. Under acidic conditions, the reaction is the reverse reaction of the <a href="/wiki/Fischer_esterification" class="mw-redirect" title="Fischer esterification">Fischer esterification</a>. Under basic conditions, <a href="/wiki/Hydroxide" title="Hydroxide">hydroxide</a> acts as a nucleophile, while an alkoxide is the leaving group. This reaction, <a href="/wiki/Saponification" title="Saponification">saponification</a>, is the basis of soap making. </p> <dl><dd><span typeof="mw:File"><a href="/wiki/File:Ester_hydrolysis.svg" class="mw-file-description" title="Ester saponification (basic hydrolysis)"><img alt="Ester saponification (basic hydrolysis)" src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f6/Ester_hydrolysis.svg/750px-Ester_hydrolysis.svg.png" decoding="async" width="750" height="189" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f6/Ester_hydrolysis.svg/1125px-Ester_hydrolysis.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f6/Ester_hydrolysis.svg/1500px-Ester_hydrolysis.svg.png 2x" data-file-width="869" data-file-height="219" /></a></span></dd></dl> <p>The alkoxide group may also be displaced by stronger nucleophiles such as <a href="/wiki/Ammonia" title="Ammonia">ammonia</a> or primary or secondary <a href="/wiki/Amine" title="Amine">amines</a> to give <a href="/wiki/Amide" title="Amide">amides</a> (ammonolysis reaction): </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">RCO<sub class="template-chem2-sub">2</sub>R' + NH<sub class="template-chem2-sub">2</sub>R″ → RCONHR″ + R'OH</span></dd></dl> <p>This reaction is not usually reversible. Hydrazines and hydroxylamine can be used in place of amines. Esters can be converted to <a href="/wiki/Isocyanate" title="Isocyanate">isocyanates</a> through intermediate <a href="/wiki/Hydroxamic_acid" title="Hydroxamic acid">hydroxamic acids</a> in the <a href="/wiki/Lossen_rearrangement" title="Lossen rearrangement">Lossen rearrangement</a>. </p><p>Sources of carbon nucleophiles, e.g., <a href="/wiki/Grignard_reagent" title="Grignard reagent">Grignard reagents</a> and organolithium compounds, add readily to the carbonyl. </p> <div class="mw-heading mw-heading3"><h3 id="Reduction">Reduction</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ester&action=edit&section=23" title="Edit section: Reduction"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Compared to ketones and aldehydes, esters are <a href="/wiki/Carbonyl_reduction#Trends_in_carbonyl_reactivity" title="Carbonyl reduction">relatively resistant to reduction</a>. The introduction of catalytic hydrogenation in the early part of the 20th century was a breakthrough; esters of fatty acids are hydrogenated to <a href="/wiki/Fatty_alcohol" title="Fatty alcohol">fatty alcohols</a>. </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">RCO<sub class="template-chem2-sub">2</sub>R' + 2 H<sub class="template-chem2-sub">2</sub> → RCH<sub class="template-chem2-sub">2</sub>OH + R'OH</span></dd></dl> <p>A typical catalyst is <a href="/wiki/Copper_chromite" title="Copper chromite">copper chromite</a>. Prior to the development of <a href="/wiki/Catalytic_hydrogenation" class="mw-redirect" title="Catalytic hydrogenation">catalytic hydrogenation</a>, esters were reduced on a large scale using the <a href="/wiki/Bouveault%E2%80%93Blanc_reduction" title="Bouveault–Blanc reduction">Bouveault–Blanc reduction</a>. This method, which is largely obsolete, uses sodium in the presence of proton sources. </p><p>Especially for fine chemical syntheses, <a href="/wiki/Lithium_aluminium_hydride" title="Lithium aluminium hydride">lithium aluminium hydride</a> is used to reduce esters to two primary alcohols. The related reagent <a href="/wiki/Sodium_borohydride" title="Sodium borohydride">sodium borohydride</a> is slow in this reaction. <a href="/wiki/DIBAH" class="mw-redirect" title="DIBAH">DIBAH</a> reduces esters to aldehydes.<sup id="cite_ref-25" class="reference"><a href="#cite_note-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> </p><p>Direct reduction to give the corresponding <a href="/wiki/Ether" title="Ether">ether</a> is difficult as the intermediate <a href="/wiki/Hemiacetal" title="Hemiacetal">hemiacetal</a> tends to decompose to give an alcohol and an aldehyde (which is rapidly reduced to give a second alcohol). The reaction can be achieved using <a href="/wiki/Triethylsilane" title="Triethylsilane">triethylsilane</a> with a variety of Lewis acids.<sup id="cite_ref-26" class="reference"><a href="#cite_note-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-27" class="reference"><a href="#cite_note-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Claisen_condensation_and_related_reactions">Claisen condensation and related reactions</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ester&action=edit&section=24" title="Edit section: Claisen condensation and related reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Esters can undergo a variety of reactions with carbon nucleophiles. They react with an excess of a Grignard reagent to give tertiary alcohols. Esters also react readily with <a href="/wiki/Enolate" title="Enolate">enolates</a>. In the <a href="/wiki/Claisen_condensation" title="Claisen condensation">Claisen condensation</a>, an enolate of one ester (<b>1</b>) will attack the carbonyl group of another ester (<b>2</b>) to give tetrahedral intermediate <b>3</b>. The intermediate collapses, forcing out an alkoxide (R'O<sup>−</sup>) and producing β-keto ester <b>4</b>. </p> <figure class="mw-default-size mw-halign-center" typeof="mw:File"><a href="/wiki/File:Claisen_condensation_-_general_mechanism.svg" class="mw-file-description" title="The Claisen condensation involves the reaction of an ester enolate and an ester to form a beta-keto ester."><img alt="The Claisen condensation involves the reaction of an ester enolate and an ester to form a beta-keto ester." src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e5/Claisen_condensation_-_general_mechanism.svg/666px-Claisen_condensation_-_general_mechanism.svg.png" decoding="async" width="666" height="136" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e5/Claisen_condensation_-_general_mechanism.svg/999px-Claisen_condensation_-_general_mechanism.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e5/Claisen_condensation_-_general_mechanism.svg/1332px-Claisen_condensation_-_general_mechanism.svg.png 2x" data-file-width="666" data-file-height="136" /></a><figcaption>The Claisen condensation involves the reaction of an ester enolate and an ester to form a beta-keto ester.</figcaption></figure> <p>Crossed Claisen condensations, in which the enolate and nucleophile are different esters, are also possible. An <a href="/wiki/Intramolecular_reaction" title="Intramolecular reaction">intramolecular</a> Claisen condensation is called a <a href="/wiki/Dieckmann_condensation" title="Dieckmann condensation">Dieckmann condensation</a> or Dieckmann cyclization, since it can be used to form rings. Esters can also undergo condensations with ketone and aldehyde enolates to give β-dicarbonyl compounds.<sup id="cite_ref-28" class="reference"><a href="#cite_note-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> A specific example of this is the <a href="/wiki/Baker%E2%80%93Venkataraman_rearrangement" title="Baker–Venkataraman rearrangement">Baker–Venkataraman rearrangement</a>, in which an aromatic <i>ortho</i>-acyloxy ketone undergoes an intramolecular nucleophilic acyl substitution and subsequent rearrangement to form an aromatic β-diketone.<sup id="cite_ref-29" class="reference"><a href="#cite_note-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> The <a href="/wiki/Chan_rearrangement" title="Chan rearrangement">Chan rearrangement</a> is another example of a rearrangement resulting from an intramolecular nucleophilic acyl substitution reaction. </p> <div class="mw-heading mw-heading3"><h3 id="Other_ester_reactivities">Other ester reactivities</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ester&action=edit&section=25" title="Edit section: Other ester reactivities"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Esters react with nucleophiles at the carbonyl carbon.<sup id="cite_ref-30" class="reference"><a href="#cite_note-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> The carbonyl is weakly electrophilic but is attacked by strong nucleophiles (amines, alkoxides, hydride sources, organolithium compounds, etc.). The C–H bonds adjacent to the carbonyl are weakly acidic but undergo deprotonation with strong bases. This process is the one that usually initiates condensation reactions. The carbonyl oxygen in esters is weakly basic, less so than the carbonyl oxygen in amides due to resonance donation of an electron pair from nitrogen in amides, but forms <a href="/wiki/Adduct" title="Adduct">adducts</a>. </p><p>As for <a href="/wiki/Aldehydes" class="mw-redirect" title="Aldehydes">aldehydes</a>, the hydrogen atoms on the carbon adjacent ("α to") the carboxyl group in esters are sufficiently acidic to undergo deprotonation, which in turn leads to a variety of useful reactions. Deprotonation requires relatively strong bases, such as <a href="/wiki/Alkoxide" title="Alkoxide">alkoxides</a>. Deprotonation gives a nucleophilic <a href="/wiki/Enolate" title="Enolate">enolate</a>, which can further react, e.g., the <a href="/wiki/Claisen_condensation" title="Claisen condensation">Claisen condensation</a> and its intramolecular equivalent, the <a href="/wiki/Dieckmann_condensation" title="Dieckmann condensation">Dieckmann condensation</a>. This conversion is exploited in the <a href="/wiki/Malonic_ester_synthesis" title="Malonic ester synthesis">malonic ester synthesis</a>, wherein the diester of <a href="/wiki/Malonic_acid" title="Malonic acid">malonic acid</a> reacts with an electrophile (e.g., <a href="/wiki/Alkyl_halide" class="mw-redirect" title="Alkyl halide">alkyl halide</a>), and is subsequently decarboxylated. Another variation is the <a href="/wiki/Fr%C3%A1ter%E2%80%93Seebach_alkylation" title="Fráter–Seebach alkylation">Fráter–Seebach alkylation</a>. </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=Ester&action=edit&section=26" title="Edit section: Other reactions"><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-More_citations_needed_section plainlinks metadata ambox ambox-content ambox-Refimprove" role="presentation"><tbody><tr><td class="mbox-image"><div class="mbox-image-div"><span typeof="mw:File"><a href="/wiki/File:Question_book-new.svg" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/9/99/Question_book-new.svg/50px-Question_book-new.svg.png" decoding="async" width="50" height="39" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/9/99/Question_book-new.svg/75px-Question_book-new.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/9/99/Question_book-new.svg/100px-Question_book-new.svg.png 2x" data-file-width="512" data-file-height="399" /></a></span></div></td><td class="mbox-text"><div class="mbox-text-span">This section <b>needs additional citations for <a href="/wiki/Wikipedia:Verifiability" title="Wikipedia:Verifiability">verification</a></b>.<span class="hide-when-compact"> Please help <a href="/wiki/Special:EditPage/Ester" title="Special:EditPage/Ester">improve this article</a> by <a href="/wiki/Help:Referencing_for_beginners" title="Help:Referencing for beginners">adding citations to reliable sources</a> in this section. Unsourced material may be challenged and removed.</span> <span class="date-container"><i>(<span class="date">September 2024</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> <ul><li>Esters can be directly converted to <a href="/wiki/Nitriles" class="mw-redirect" title="Nitriles">nitriles</a>.<sup id="cite_ref-31" class="reference"><a href="#cite_note-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup><sup class="noprint Inline-Template noprint Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:No_original_research#Primary,_secondary_and_tertiary_sources" title="Wikipedia:No original research"><span title="This claim needs references to reliable secondary sources. (September 2024)">non-primary source needed</span></a></i>]</sup></li> <li>Methyl esters are often susceptible to decarboxylation in the <a href="/wiki/Krapcho_decarboxylation" title="Krapcho decarboxylation">Krapcho decarboxylation</a>.</li> <li>Phenyl esters react to hydroxyarylketones in the <a href="/wiki/Fries_rearrangement" title="Fries rearrangement">Fries rearrangement</a>.</li> <li>Specific esters are functionalized with an α-hydroxyl group in the <a href="/wiki/Chan_rearrangement" title="Chan rearrangement">Chan rearrangement</a>.</li> <li>Esters with β-hydrogen atoms can be converted to alkenes in <a href="/wiki/Ester_pyrolysis" title="Ester pyrolysis">ester pyrolysis</a>.</li> <li>Pairs of esters are coupled to give <a href="/wiki/Alpha-hydroxy_ketone" class="mw-redirect" title="Alpha-hydroxy ketone">α-hydroxyketones</a> in the <a href="/wiki/Acyloin_condensation" title="Acyloin condensation">acyloin condensation</a></li></ul> <div class="mw-heading mw-heading3"><h3 id="Protecting_groups">Protecting groups</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ester&action=edit&section=27" title="Edit section: Protecting groups"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>As a class, esters serve as <a href="/wiki/Protecting_group" title="Protecting group">protecting groups</a> for <a href="/wiki/Carboxylic_acid" title="Carboxylic acid">carboxylic acids</a>. Protecting a carboxylic acid is useful in peptide synthesis, to prevent self-reactions of the bifunctional <a href="/wiki/Amino_acid" title="Amino acid">amino acids</a>. Methyl and ethyl esters are commonly available for many amino acids; the <i>t</i>-butyl ester tends to be more expensive. However, <i>t</i>-butyl esters are particularly useful because, under strongly acidic conditions, the <i>t</i>-butyl esters undergo elimination to give the carboxylic acid and <a href="/wiki/Isobutylene" title="Isobutylene">isobutylene</a>, simplifying work-up. </p> <div class="mw-heading mw-heading2"><h2 id="List_of_ester_odorants">List of ester odorants</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ester&action=edit&section=28" title="Edit section: List of ester odorants"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Many esters have distinctive fruit-like odors, and many occur naturally in the essential oils of plants. This has also led to their common use in artificial flavorings and fragrances which aim to mimic those odors.<sup id="cite_ref-32" class="reference"><a href="#cite_note-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> </p> <table class="wikitable"> <tbody><tr> <th valign="top" align="left">Acetate ester </th> <th valign="top" align="left">Structure </th> <th valign="top" align="left">Odor or occurrence </th></tr> <tr> <td><a href="/wiki/Methyl_acetate" title="Methyl acetate">Methyl acetate</a> </td> <td><span typeof="mw:File"><a href="/wiki/File:Methyl-acetate-2D-skeletal.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b7/Methyl-acetate-2D-skeletal.svg/75px-Methyl-acetate-2D-skeletal.svg.png" decoding="async" width="75" height="61" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b7/Methyl-acetate-2D-skeletal.svg/113px-Methyl-acetate-2D-skeletal.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b7/Methyl-acetate-2D-skeletal.svg/150px-Methyl-acetate-2D-skeletal.svg.png 2x" data-file-width="157" data-file-height="127" /></a></span> </td> <td><a href="/wiki/Glue" class="mw-redirect" title="Glue">glue</a> </td></tr> <tr> <td><a href="/wiki/Ethyl_acetate" title="Ethyl acetate">Ethyl acetate</a> </td> <td><span typeof="mw:File"><a href="/wiki/File:Ethyl-acetate-2D-skeletal.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c9/Ethyl-acetate-2D-skeletal.svg/75px-Ethyl-acetate-2D-skeletal.svg.png" decoding="async" width="75" height="47" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c9/Ethyl-acetate-2D-skeletal.svg/113px-Ethyl-acetate-2D-skeletal.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c9/Ethyl-acetate-2D-skeletal.svg/150px-Ethyl-acetate-2D-skeletal.svg.png 2x" data-file-width="201" data-file-height="127" /></a></span> </td> <td><a href="/wiki/Nail_polish_remover" class="mw-redirect" title="Nail polish remover">nail polish remover</a>, <a href="/wiki/Scale_model" title="Scale model">model</a> <a href="/wiki/Paint" title="Paint">paint</a>, <a href="/wiki/Model_aircraft" title="Model aircraft">model airplane</a> <a href="/wiki/Adhesive" title="Adhesive">glue</a>, <a href="/wiki/Pears" class="mw-redirect" title="Pears">pears</a> </td></tr> <tr> <td><a href="/wiki/Propyl_acetate" title="Propyl acetate">Propyl acetate</a> </td> <td><span typeof="mw:File"><a href="/wiki/File:Propyl_acetate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/bd/Propyl_acetate.svg/75px-Propyl_acetate.svg.png" decoding="async" width="75" height="38" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/bd/Propyl_acetate.svg/113px-Propyl_acetate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/bd/Propyl_acetate.svg/150px-Propyl_acetate.svg.png 2x" data-file-width="192" data-file-height="96" /></a></span> </td> <td><a href="/wiki/Pear" title="Pear">pear</a> </td></tr> <tr> <td><a href="/wiki/Isopropyl_acetate" title="Isopropyl acetate">Isopropyl acetate</a> </td> <td><span typeof="mw:File"><a href="/wiki/File:Isopropyl_acetate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/be/Isopropyl_acetate.svg/75px-Isopropyl_acetate.svg.png" decoding="async" width="75" height="42" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/be/Isopropyl_acetate.svg/113px-Isopropyl_acetate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/be/Isopropyl_acetate.svg/150px-Isopropyl_acetate.svg.png 2x" data-file-width="520" data-file-height="294" /></a></span> </td> <td>fruity </td></tr> <tr> <td><a href="/wiki/Butyl_acetate" title="Butyl acetate">Butyl acetate</a> </td> <td><span typeof="mw:File"><a href="/wiki/File:Butylacetat.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/8b/Butylacetat.svg/75px-Butylacetat.svg.png" decoding="async" width="75" height="29" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/8b/Butylacetat.svg/113px-Butylacetat.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/8b/Butylacetat.svg/150px-Butylacetat.svg.png 2x" data-file-width="264" data-file-height="103" /></a></span> </td> <td><a href="/wiki/Apple" title="Apple">apple</a>, <a href="/wiki/Honey" title="Honey">honey</a> </td></tr> <tr> <td><a href="/wiki/Isobutyl_acetate" title="Isobutyl acetate">Isobutyl acetate</a> </td> <td><span typeof="mw:File"><a href="/wiki/File:Isobutyl-acetate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/4e/Isobutyl-acetate.svg/75px-Isobutyl-acetate.svg.png" decoding="async" width="75" height="51" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/4e/Isobutyl-acetate.svg/113px-Isobutyl-acetate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/4e/Isobutyl-acetate.svg/150px-Isobutyl-acetate.svg.png 2x" data-file-width="331" data-file-height="226" /></a></span> </td> <td><a href="/wiki/Cherry" title="Cherry">cherry</a>, <a href="/wiki/Raspberry" title="Raspberry">raspberry</a>, <a href="/wiki/Strawberry" title="Strawberry">strawberry</a> </td></tr> <tr> <td><a href="/wiki/Amyl_acetate" title="Amyl acetate">Amyl acetate</a> (pentyl acetate) </td> <td><span typeof="mw:File"><a href="/wiki/File:Amyl_acetate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e0/Amyl_acetate.svg/75px-Amyl_acetate.svg.png" decoding="async" width="75" height="25" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e0/Amyl_acetate.svg/113px-Amyl_acetate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e0/Amyl_acetate.svg/150px-Amyl_acetate.svg.png 2x" data-file-width="893" data-file-height="293" /></a></span> </td> <td><a href="/wiki/Apple" title="Apple">apple</a>, <a href="/wiki/Banana" title="Banana">banana</a> </td></tr> <tr> <td><a href="/wiki/Isoamyl_acetate" title="Isoamyl acetate">Isoamyl acetate</a> </td> <td><span typeof="mw:File"><a href="/wiki/File:Isoamyl_acetate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/ba/Isoamyl_acetate.svg/75px-Isoamyl_acetate.svg.png" decoding="async" width="75" height="31" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/ba/Isoamyl_acetate.svg/113px-Isoamyl_acetate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/ba/Isoamyl_acetate.svg/150px-Isoamyl_acetate.svg.png 2x" data-file-width="349" data-file-height="144" /></a></span> </td> <td><a href="/wiki/Pear" title="Pear">pear</a>, <a href="/wiki/Banana" title="Banana">banana</a> (main component of banana essence) (flavoring in <a href="/wiki/Pear_drop" title="Pear drop">Pear drops</a>) </td></tr> <tr> <td><a href="/wiki/Hexyl_acetate" title="Hexyl acetate">hexyl acetate</a> </td> <td><span typeof="mw:File"><a href="/wiki/File:Octyl_acetate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/67/Octyl_acetate.svg/75px-Octyl_acetate.svg.png" decoding="async" width="75" height="20" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/67/Octyl_acetate.svg/113px-Octyl_acetate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/67/Octyl_acetate.svg/150px-Octyl_acetate.svg.png 2x" data-file-width="632" data-file-height="172" /></a></span> </td> <td>pear-like </td></tr> <tr> <td><a href="/w/index.php?title=2-Hexenyl_acetate&action=edit&redlink=1" class="new" title="2-Hexenyl acetate (page does not exist)">2-Hexenyl acetate</a> </td> <td> </td> <td>fruity, both cis and trans are used, sometimes individually </td></tr> <tr> <td><a href="/w/index.php?title=3,5,5-Trimethylhexyl_acetate&action=edit&redlink=1" class="new" title="3,5,5-Trimethylhexyl acetate (page does not exist)">3,5,5-Trimethylhexyl acetate</a> </td> <td> </td> <td>woody </td></tr> <tr> <td><a href="/wiki/Octyl_acetate" title="Octyl acetate">Octyl acetate</a> </td> <td><span typeof="mw:File"><a href="/wiki/File:Octyl_acetate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/67/Octyl_acetate.svg/75px-Octyl_acetate.svg.png" decoding="async" width="75" height="20" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/67/Octyl_acetate.svg/113px-Octyl_acetate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/67/Octyl_acetate.svg/150px-Octyl_acetate.svg.png 2x" data-file-width="632" data-file-height="172" /></a></span> </td> <td>fruity-<a href="/wiki/Orange_(fruit)" title="Orange (fruit)">orange</a> </td></tr> <tr> <td><a href="/wiki/Benzyl_acetate" title="Benzyl acetate">Benzyl acetate</a> </td> <td><span typeof="mw:File"><a href="/wiki/File:Benzyl_acetate-structure.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/2f/Benzyl_acetate-structure.svg/75px-Benzyl_acetate-structure.svg.png" decoding="async" width="75" height="48" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/2f/Benzyl_acetate-structure.svg/113px-Benzyl_acetate-structure.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/2f/Benzyl_acetate-structure.svg/150px-Benzyl_acetate-structure.svg.png 2x" data-file-width="587" data-file-height="374" /></a></span> </td> <td><a href="/wiki/Pear" title="Pear">pear</a>, <a href="/wiki/Strawberry" title="Strawberry">strawberry</a>, <a href="/wiki/Jasmine" title="Jasmine">jasmine</a> </td></tr> <tr> <td><a href="/wiki/Bornyl_acetate" title="Bornyl acetate">Bornyl acetate</a> </td> <td><span typeof="mw:File"><a href="/wiki/File:Bornyl_acetate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/7b/Bornyl_acetate.svg/75px-Bornyl_acetate.svg.png" decoding="async" width="75" height="101" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/7b/Bornyl_acetate.svg/113px-Bornyl_acetate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/7b/Bornyl_acetate.svg/150px-Bornyl_acetate.svg.png 2x" data-file-width="292" data-file-height="393" /></a></span> </td> <td><a href="/wiki/Pine" title="Pine">pine</a> (see also <a href="/wiki/Isobornyl_acetate" title="Isobornyl acetate">isobornyl acetate</a>) </td></tr> <tr> <td><a href="/wiki/Geranyl_acetate" title="Geranyl acetate">Geranyl acetate</a> </td> <td><span typeof="mw:File"><a href="/wiki/File:Geranyl-acetate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/06/Geranyl-acetate.svg/75px-Geranyl-acetate.svg.png" decoding="async" width="75" height="20" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/06/Geranyl-acetate.svg/113px-Geranyl-acetate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/06/Geranyl-acetate.svg/150px-Geranyl-acetate.svg.png 2x" data-file-width="630" data-file-height="172" /></a></span> </td> <td><a href="/wiki/Pelargonium" title="Pelargonium">geranium</a> </td></tr> <tr> <td><a href="/wiki/Menthyl_acetate" title="Menthyl acetate">menthyl acetate</a> </td> <td> </td> <td>peppermint </td></tr> <tr> <td><a href="/wiki/Linalyl_acetate" title="Linalyl acetate">Linalyl acetate</a> </td> <td><span typeof="mw:File"><a href="/wiki/File:Linalyl_acetate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b5/Linalyl_acetate.svg/75px-Linalyl_acetate.svg.png" decoding="async" width="75" height="43" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b5/Linalyl_acetate.svg/113px-Linalyl_acetate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b5/Linalyl_acetate.svg/150px-Linalyl_acetate.svg.png 2x" data-file-width="512" data-file-height="291" /></a></span> </td> <td><a href="/wiki/Lavender" class="mw-redirect" title="Lavender">lavender</a>, <a href="/wiki/Common_sage" class="mw-redirect" title="Common sage">sage</a> </td></tr> </tbody></table> <table class="wikitable"> <tbody><tr> <th valign="top" align="left">Formate esters </th> <th valign="top" align="left">Structure </th> <th valign="top" align="left">Odor or occurrence </th></tr> <tr> <td><a href="/wiki/Isobutyl_formate" title="Isobutyl formate">Isobutyl formate</a> </td> <td><span typeof="mw:File"><a href="/wiki/File:Isobutyl_formate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b9/Isobutyl_formate.svg/75px-Isobutyl_formate.svg.png" decoding="async" width="75" height="25" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b9/Isobutyl_formate.svg/113px-Isobutyl_formate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b9/Isobutyl_formate.svg/150px-Isobutyl_formate.svg.png 2x" data-file-width="512" data-file-height="171" /></a></span> </td> <td><a href="/wiki/Raspberry" title="Raspberry">raspberry</a> </td></tr> <tr> <td><a href="/w/index.php?title=Linalyl_formate&action=edit&redlink=1" class="new" title="Linalyl formate (page does not exist)">Linalyl formate</a> </td> <td><span typeof="mw:File"><a href="/wiki/File:Linalyl_formate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a3/Linalyl_formate.svg/75px-Linalyl_formate.svg.png" decoding="async" width="75" height="42" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a3/Linalyl_formate.svg/113px-Linalyl_formate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a3/Linalyl_formate.svg/150px-Linalyl_formate.svg.png 2x" data-file-width="512" data-file-height="287" /></a></span> </td> <td><a href="/wiki/Apple" title="Apple">apple</a>, <a href="/wiki/Peach" title="Peach">peach</a> </td></tr> <tr> <td><a href="/wiki/Isoamyl_formate" title="Isoamyl formate">Isoamyl formate</a> </td> <td><span typeof="mw:File"><a href="/wiki/File:Isoamyl_formate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/43/Isoamyl_formate.svg/75px-Isoamyl_formate.svg.png" decoding="async" width="75" height="28" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/43/Isoamyl_formate.svg/113px-Isoamyl_formate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/43/Isoamyl_formate.svg/150px-Isoamyl_formate.svg.png 2x" data-file-width="111" data-file-height="41" /></a></span> </td> <td><a href="/wiki/Plum" title="Plum">plum</a>, <a href="/wiki/Blackcurrant" title="Blackcurrant">blackcurrant</a> </td></tr> <tr> <td><a href="/wiki/Ethyl_formate" title="Ethyl formate">Ethyl formate</a> </td> <td><span typeof="mw:File"><a href="/wiki/File:Ethyl_formate_Structural_Formulae.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0a/Ethyl_formate_Structural_Formulae.svg/75px-Ethyl_formate_Structural_Formulae.svg.png" decoding="async" width="75" height="36" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0a/Ethyl_formate_Structural_Formulae.svg/113px-Ethyl_formate_Structural_Formulae.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/0a/Ethyl_formate_Structural_Formulae.svg/150px-Ethyl_formate_Structural_Formulae.svg.png 2x" data-file-width="294" data-file-height="141" /></a></span> </td> <td><a href="/wiki/Lemon" title="Lemon">lemon</a>, <a href="/wiki/Rum" title="Rum">rum</a>, <a href="/wiki/Strawberry" title="Strawberry">strawberry</a> </td></tr> <tr> <td><a href="/wiki/Methyl_formate" title="Methyl formate">Methyl formate</a> </td> <td><span typeof="mw:File"><a href="/wiki/File:Methyl_formate.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/80/Methyl_formate.png/75px-Methyl_formate.png" decoding="async" width="75" height="40" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/80/Methyl_formate.png/113px-Methyl_formate.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/80/Methyl_formate.png/150px-Methyl_formate.png 2x" data-file-width="949" data-file-height="500" /></a></span> </td> <td>pleasant, <a href="/wiki/Diethyl_ether" title="Diethyl ether">ethereal</a>, <a href="/wiki/Rum" title="Rum">rum</a>, sweet </td></tr></tbody></table> <table class="wikitable"> <tbody><tr> <th valign="top" align="left">Propionate, butyrate, and isobutyrate esters </th> <th valign="top" align="left">Structure </th> <th valign="top" align="left">Odor or occurrence </th></tr> <tr> <td><a href="/wiki/Butyl_propionate" title="Butyl propionate">Butyl propionate</a> </td> <td><span typeof="mw:File"><a href="/wiki/File:Butyl_propionate.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d4/Butyl_propionate.png/75px-Butyl_propionate.png" decoding="async" width="75" height="34" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d4/Butyl_propionate.png/113px-Butyl_propionate.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d4/Butyl_propionate.png/150px-Butyl_propionate.png 2x" data-file-width="1080" data-file-height="486" /></a></span> </td> <td><a href="/wiki/Pear_drops" class="mw-redirect" title="Pear drops">pear drops</a>, <a href="/wiki/Apple" title="Apple">apple</a>, rare example of a propionate odorant </td></tr> <tr> <td><a href="/wiki/Methyl_butyrate" title="Methyl butyrate">Methyl butyrate</a> </td> <td><span typeof="mw:File"><a href="/wiki/File:Buttersauremethylester.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/15/Buttersauremethylester.svg/75px-Buttersauremethylester.svg.png" decoding="async" width="75" height="37" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/15/Buttersauremethylester.svg/113px-Buttersauremethylester.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/15/Buttersauremethylester.svg/150px-Buttersauremethylester.svg.png 2x" data-file-width="123" data-file-height="60" /></a></span> </td> <td><a href="/wiki/Pineapple" title="Pineapple">pineapple</a>, <a href="/wiki/Apple" title="Apple">apple</a>, <a href="/wiki/Strawberry" title="Strawberry">strawberry</a> </td></tr> <tr> <td><a href="/wiki/Ethyl_butyrate" title="Ethyl butyrate">Ethyl butyrate</a> </td> <td><span typeof="mw:File"><a href="/wiki/File:Ethyl_butyrate2.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0e/Ethyl_butyrate2.svg/75px-Ethyl_butyrate2.svg.png" decoding="async" width="75" height="33" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0e/Ethyl_butyrate2.svg/113px-Ethyl_butyrate2.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/0e/Ethyl_butyrate2.svg/150px-Ethyl_butyrate2.svg.png 2x" data-file-width="393" data-file-height="172" /></a></span> </td> <td><a href="/wiki/Banana" title="Banana">banana</a>, <a href="/wiki/Pineapple" title="Pineapple">pineapple</a>, <a href="/wiki/Strawberry" title="Strawberry">strawberry</a>, perfumes </td></tr> <tr> <td><a href="/w/index.php?title=Propyl_isobutyrate&action=edit&redlink=1" class="new" title="Propyl isobutyrate (page does not exist)">Propyl isobutyrate</a> </td> <td><span typeof="mw:File"><a href="/wiki/File:Propyl_isobutyrate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/90/Propyl_isobutyrate.svg/75px-Propyl_isobutyrate.svg.png" decoding="async" width="75" height="43" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/90/Propyl_isobutyrate.svg/113px-Propyl_isobutyrate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/90/Propyl_isobutyrate.svg/150px-Propyl_isobutyrate.svg.png 2x" data-file-width="392" data-file-height="225" /></a></span> </td> <td><a href="/wiki/Rum" title="Rum">rum</a> </td></tr> <tr> <td><a href="/wiki/Butyl_butyrate" title="Butyl butyrate">Butyl butyrate</a> </td> <td><span typeof="mw:File"><a href="/wiki/File:Butyl_butyrate2.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e7/Butyl_butyrate2.svg/75px-Butyl_butyrate2.svg.png" decoding="async" width="75" height="22" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e7/Butyl_butyrate2.svg/113px-Butyl_butyrate2.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e7/Butyl_butyrate2.svg/150px-Butyl_butyrate2.svg.png 2x" data-file-width="513" data-file-height="150" /></a></span> </td> <td><a href="/wiki/Pineapple" title="Pineapple">pineapple</a>, honey </td></tr> <tr> <td><a href="/w/index.php?title=Isoamy_butyrate&action=edit&redlink=1" class="new" title="Isoamy butyrate (page does not exist)">Isoamy butyrate</a> </td> <td> </td> <td>banana </td></tr> <tr> <td><a href="/w/index.php?title=Hexyl_butyrate&action=edit&redlink=1" class="new" title="Hexyl butyrate (page does not exist)">hexyl butyrate</a> </td> <td> </td> <td><a href="/wiki/Fruit" title="Fruit">fruits</a> </td></tr> <tr> <td><a href="/w/index.php?title=Ethyl_isobutyrate&action=edit&redlink=1" class="new" title="Ethyl isobutyrate (page does not exist)">Ethyl isobutyrate</a> </td> <td> </td> <td>blueberries, used in alcoholic drinks </td></tr> <tr> <td><a href="/w/index.php?title=Linalyl_butyrate&action=edit&redlink=1" class="new" title="Linalyl butyrate (page does not exist)">Linalyl butyrate</a> </td> <td><span typeof="mw:File"><a href="/wiki/File:Linalyl_butyrate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b7/Linalyl_butyrate.svg/75px-Linalyl_butyrate.svg.png" decoding="async" width="75" height="38" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b7/Linalyl_butyrate.svg/113px-Linalyl_butyrate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b7/Linalyl_butyrate.svg/150px-Linalyl_butyrate.svg.png 2x" data-file-width="512" data-file-height="259" /></a></span> </td> <td><a href="/wiki/Peach" title="Peach">peach</a> </td></tr> <tr> <td><a href="/w/index.php?title=Geranyl_butyrate&action=edit&redlink=1" class="new" title="Geranyl butyrate (page does not exist)">Geranyl butyrate</a> </td> <td><span typeof="mw:File"><a href="/wiki/File:Geranyl_butyrate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/71/Geranyl_butyrate.svg/75px-Geranyl_butyrate.svg.png" decoding="async" width="75" height="17" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/71/Geranyl_butyrate.svg/113px-Geranyl_butyrate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/71/Geranyl_butyrate.svg/150px-Geranyl_butyrate.svg.png 2x" data-file-width="752" data-file-height="172" /></a></span> </td> <td><a href="/wiki/Cherry" title="Cherry">cherry</a> </td></tr> <tr> <td><a href="/w/index.php?title=Terpinyl_butyrate&action=edit&redlink=1" class="new" title="Terpinyl butyrate (page does not exist)">Terpinyl butyrate</a> </td> <td><span typeof="mw:File"><a href="/wiki/File:Terpenyl_butyrate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/5e/Terpenyl_butyrate.svg/75px-Terpenyl_butyrate.svg.png" decoding="async" width="75" height="52" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/5e/Terpenyl_butyrate.svg/113px-Terpenyl_butyrate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/5e/Terpenyl_butyrate.svg/150px-Terpenyl_butyrate.svg.png 2x" data-file-width="518" data-file-height="359" /></a></span> </td> <td><a href="/wiki/Cherry" title="Cherry">cherry</a> </td></tr></tbody></table> <table class="wikitable"> <tbody><tr> <th valign="top" align="left">C5-C9 aliphatic esters </th> <th valign="top" align="left">Structure </th> <th valign="top" align="left">Odor or occurrence </th></tr> <tr> <td><a href="/wiki/Methyl_pentanoate" title="Methyl pentanoate">Methyl pentanoate</a> (methyl valerate) </td> <td><span typeof="mw:File"><a href="/wiki/File:Methyl_pentanoate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/7b/Methyl_pentanoate.svg/75px-Methyl_pentanoate.svg.png" decoding="async" width="75" height="33" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/7b/Methyl_pentanoate.svg/113px-Methyl_pentanoate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/7b/Methyl_pentanoate.svg/150px-Methyl_pentanoate.svg.png 2x" data-file-width="512" data-file-height="225" /></a></span> </td> <td><a href="/wiki/Flower" title="Flower">flowery</a> </td></tr> <tr> <td><a href="/wiki/Ethyl_isovalerate" title="Ethyl isovalerate">Ethyl isovalerate</a> </td> <td><span typeof="mw:File"><a href="/wiki/File:Ethyl_isovalerate_structure.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f4/Ethyl_isovalerate_structure.svg/75px-Ethyl_isovalerate_structure.svg.png" decoding="async" width="75" height="32" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f4/Ethyl_isovalerate_structure.svg/113px-Ethyl_isovalerate_structure.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f4/Ethyl_isovalerate_structure.svg/150px-Ethyl_isovalerate_structure.svg.png 2x" data-file-width="385" data-file-height="165" /></a></span> </td> <td><a href="/wiki/Fruity" class="mw-redirect" title="Fruity">fruity</a>, used in alcoholic drinks </td></tr> <tr> <td><a href="/w/index.php?title=Geranyl_pentanoate&action=edit&redlink=1" class="new" title="Geranyl pentanoate (page does not exist)">Geranyl pentanoate</a> </td> <td><span typeof="mw:File"><a href="/wiki/File:Geranyl_pentanoate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/4c/Geranyl_pentanoate.svg/75px-Geranyl_pentanoate.svg.png" decoding="async" width="75" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/4c/Geranyl_pentanoate.svg/113px-Geranyl_pentanoate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/4c/Geranyl_pentanoate.svg/150px-Geranyl_pentanoate.svg.png 2x" data-file-width="575" data-file-height="123" /></a></span> </td> <td><a href="/wiki/Apple" title="Apple">apple</a> </td></tr> <tr> <td><a href="/wiki/Pentyl_pentanoate" title="Pentyl pentanoate">Pentyl pentanoate</a> (amyl valerate) </td> <td><span typeof="mw:File"><a href="/wiki/File:Pentyl_pentanoate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/44/Pentyl_pentanoate.svg/75px-Pentyl_pentanoate.svg.png" decoding="async" width="75" height="20" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/44/Pentyl_pentanoate.svg/113px-Pentyl_pentanoate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/44/Pentyl_pentanoate.svg/150px-Pentyl_pentanoate.svg.png 2x" data-file-width="630" data-file-height="172" /></a></span> </td> <td><a href="/wiki/Apple" title="Apple">apple</a> </td></tr> <tr> <td><a href="/wiki/Propyl_hexanoate" title="Propyl hexanoate">Propyl hexanoate</a> </td> <td><span typeof="mw:File"><a href="/wiki/File:Propyl-hexanoate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/cb/Propyl-hexanoate.svg/75px-Propyl-hexanoate.svg.png" decoding="async" width="75" height="23" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/cb/Propyl-hexanoate.svg/113px-Propyl-hexanoate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/cb/Propyl-hexanoate.svg/150px-Propyl-hexanoate.svg.png 2x" data-file-width="571" data-file-height="172" /></a></span> </td> <td><a href="/wiki/Blackberry" title="Blackberry">blackberry</a>, <a href="/wiki/Pineapple" title="Pineapple">pineapple</a> </td></tr> <tr> <td><a href="/wiki/Ethyl_heptanoate" title="Ethyl heptanoate">Ethyl heptanoate</a> </td> <td><span typeof="mw:File"><a href="/wiki/File:Ethyl-heptanoate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/82/Ethyl-heptanoate.svg/75px-Ethyl-heptanoate.svg.png" decoding="async" width="75" height="23" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/82/Ethyl-heptanoate.svg/113px-Ethyl-heptanoate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/82/Ethyl-heptanoate.svg/150px-Ethyl-heptanoate.svg.png 2x" data-file-width="572" data-file-height="172" /></a></span> </td> <td><a href="/wiki/Apricot" title="Apricot">apricot</a>, <a href="/wiki/Cherry" title="Cherry">cherry</a>, <a href="/wiki/Grape" title="Grape">grape</a>, <a href="/wiki/Raspberry" title="Raspberry">raspberry</a>, used in alcoholic drinks </td></tr> <tr> <td><a href="/wiki/Pentyl_hexanoate" title="Pentyl hexanoate">Pentyl hexanoate</a> (amyl caproate) </td> <td><span typeof="mw:File"><a href="/wiki/File:Pentyl_hexanoate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e8/Pentyl_hexanoate.svg/75px-Pentyl_hexanoate.svg.png" decoding="async" width="75" height="19" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e8/Pentyl_hexanoate.svg/113px-Pentyl_hexanoate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e8/Pentyl_hexanoate.svg/150px-Pentyl_hexanoate.svg.png 2x" data-file-width="690" data-file-height="172" /></a></span> </td> <td><a href="/wiki/Apple" title="Apple">apple</a>, <a href="/wiki/Pineapple" title="Pineapple">pineapple</a> </td></tr> <tr> <td><a href="/wiki/Allyl_hexanoate" title="Allyl hexanoate">Allyl hexanoate</a> </td> <td><span typeof="mw:File"><a href="/wiki/File:Prop-2-enyl_hexanoate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/3e/Prop-2-enyl_hexanoate.svg/75px-Prop-2-enyl_hexanoate.svg.png" decoding="async" width="75" height="20" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/3e/Prop-2-enyl_hexanoate.svg/113px-Prop-2-enyl_hexanoate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/3e/Prop-2-enyl_hexanoate.svg/150px-Prop-2-enyl_hexanoate.svg.png 2x" data-file-width="1887" data-file-height="500" /></a></span> </td> <td><a href="/wiki/Pineapple" title="Pineapple">pineapple</a> </td></tr> <tr> <td><a href="/wiki/Ethyl_hexanoate" title="Ethyl hexanoate">Ethyl hexanoate</a> </td> <td><span typeof="mw:File"><a href="/wiki/File:Ethyl-hexanoate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/da/Ethyl-hexanoate.svg/75px-Ethyl-hexanoate.svg.png" decoding="async" width="75" height="25" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/da/Ethyl-hexanoate.svg/113px-Ethyl-hexanoate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/da/Ethyl-hexanoate.svg/150px-Ethyl-hexanoate.svg.png 2x" data-file-width="513" data-file-height="172" /></a></span> </td> <td><a href="/wiki/Pineapple" title="Pineapple">pineapple</a>, <a href="/w/index.php?title=Waxy-green_banana&action=edit&redlink=1" class="new" title="Waxy-green banana (page does not exist)">waxy-green banana</a> </td></tr> <tr> <td><a href="/w/index.php?title=Ethyl_nonanoate&action=edit&redlink=1" class="new" title="Ethyl nonanoate (page does not exist)">Ethyl nonanoate</a> </td> <td><span typeof="mw:File"><a href="/wiki/File:Ethyl-nonanoate-2D-skeletal.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/84/Ethyl-nonanoate-2D-skeletal.svg/75px-Ethyl-nonanoate-2D-skeletal.svg.png" decoding="async" width="75" height="19" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/84/Ethyl-nonanoate-2D-skeletal.svg/113px-Ethyl-nonanoate-2D-skeletal.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/84/Ethyl-nonanoate-2D-skeletal.svg/150px-Ethyl-nonanoate-2D-skeletal.svg.png 2x" data-file-width="506" data-file-height="127" /></a></span> </td> <td><a href="/wiki/Grape" title="Grape">grape</a> </td></tr> <tr> <td><a href="/w/index.php?title=Nonyl_caprylate&action=edit&redlink=1" class="new" title="Nonyl caprylate (page does not exist)">Nonyl caprylate</a> </td> <td><span typeof="mw:File"><a href="/wiki/File:Nonyl_caprylate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/22/Nonyl_caprylate.svg/75px-Nonyl_caprylate.svg.png" decoding="async" width="75" height="12" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/22/Nonyl_caprylate.svg/113px-Nonyl_caprylate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/22/Nonyl_caprylate.svg/150px-Nonyl_caprylate.svg.png 2x" data-file-width="1050" data-file-height="172" /></a></span> </td> <td><a href="/wiki/Orange_(fruit)" title="Orange (fruit)">orange</a> </td></tr> </tbody></table> <table class="wikitable"> <tbody><tr> <th valign="top" align="left">Esters of aromatic acids </th> <th valign="top" align="left">Structure </th> <th valign="top" align="left">Odor or occurrence </th></tr> <tr> <td><a href="/wiki/Ethyl_benzoate" title="Ethyl benzoate">Ethyl benzoate</a> </td> <td><span typeof="mw:File"><a href="/wiki/File:Ethyl_benzoate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/80/Ethyl_benzoate.svg/75px-Ethyl_benzoate.svg.png" decoding="async" width="75" height="49" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/80/Ethyl_benzoate.svg/113px-Ethyl_benzoate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/80/Ethyl_benzoate.svg/150px-Ethyl_benzoate.svg.png 2x" data-file-width="395" data-file-height="260" /></a></span> </td> <td><a href="/wiki/Sweet" class="mw-redirect" title="Sweet">sweet</a>, <a href="/wiki/Wintergreen" title="Wintergreen">wintergreen</a>, <a href="/wiki/Fruit" title="Fruit">fruity</a>, medicinal, <a href="/wiki/Cherry" title="Cherry">cherry</a>, <a href="/wiki/Grape" title="Grape">grape</a> </td></tr> <tr> <td><a href="/wiki/Ethyl_cinnamate" title="Ethyl cinnamate">Ethyl cinnamate</a> </td> <td><span typeof="mw:File"><a href="/wiki/File:Ethyl-cinnamate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/20/Ethyl-cinnamate.svg/75px-Ethyl-cinnamate.svg.png" decoding="async" width="75" height="36" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/20/Ethyl-cinnamate.svg/113px-Ethyl-cinnamate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/20/Ethyl-cinnamate.svg/150px-Ethyl-cinnamate.svg.png 2x" data-file-width="1266" data-file-height="602" /></a></span> </td> <td><a href="/wiki/Cinnamon" title="Cinnamon">cinnamon</a> </td></tr> <tr> <td><a href="/wiki/Methyl_cinnamate" title="Methyl cinnamate">Methyl cinnamate</a> </td> <td><span typeof="mw:File"><a href="/wiki/File:Methyl_cinnamate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/9e/Methyl_cinnamate.svg/75px-Methyl_cinnamate.svg.png" decoding="async" width="75" height="37" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/9e/Methyl_cinnamate.svg/113px-Methyl_cinnamate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/9e/Methyl_cinnamate.svg/150px-Methyl_cinnamate.svg.png 2x" data-file-width="1234" data-file-height="604" /></a></span> </td> <td><a href="/wiki/Strawberry" title="Strawberry">strawberry</a> </td></tr> <tr> <td><a href="/wiki/Methyl_phenylacetate" title="Methyl phenylacetate">Methyl phenylacetate</a> </td> <td><span typeof="mw:File"><a href="/wiki/File:Methyl_phenylacetate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/df/Methyl_phenylacetate.svg/75px-Methyl_phenylacetate.svg.png" decoding="async" width="75" height="37" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/df/Methyl_phenylacetate.svg/113px-Methyl_phenylacetate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/df/Methyl_phenylacetate.svg/150px-Methyl_phenylacetate.svg.png 2x" data-file-width="394" data-file-height="196" /></a></span> </td> <td><a href="/wiki/Honey" title="Honey">honey</a> </td></tr> <tr> <td><a href="/wiki/Methyl_salicylate" title="Methyl salicylate">Methyl salicylate</a> (oil of wintergreen) </td> <td><span typeof="mw:File"><a href="/wiki/File:Methyl_salicylate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/95/Methyl_salicylate.svg/75px-Methyl_salicylate.svg.png" decoding="async" width="75" height="62" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/95/Methyl_salicylate.svg/113px-Methyl_salicylate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/95/Methyl_salicylate.svg/150px-Methyl_salicylate.svg.png 2x" data-file-width="334" data-file-height="277" /></a></span> </td> <td>Modern <a href="/wiki/Root_beer" title="Root beer">root beer</a>, <a href="/wiki/Wintergreen" title="Wintergreen">wintergreen</a>, <a href="/wiki/Germolene" title="Germolene">Germolene</a> and <a href="/wiki/Ralgex" title="Ralgex">Ralgex</a> ointments (UK) </td></tr> </tbody></table> <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=Ester&action=edit&section=29" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/List_of_esters" title="List of esters">List of esters</a></li> <li><a href="/wiki/Amide" title="Amide">Amide</a></li> <li><a href="/wiki/Thioamide" title="Thioamide">Thioamide</a></li> <li><a href="/wiki/Carboximidate" title="Carboximidate">Carboximidate</a></li> <li><a href="/wiki/Carbamate" title="Carbamate">Carbamate</a></li> <li><a href="/wiki/Xanthate" title="Xanthate">Xanthate</a></li> <li><a href="/wiki/Amidine" title="Amidine">Amidine</a></li> <li><a href="/wiki/Cyanate" title="Cyanate">Cyanate</a></li> <li><a href="/wiki/Thiocyanate" title="Thiocyanate">Thiocyanate</a></li> <li><a href="/wiki/Organic_selenocyanates" title="Organic selenocyanates">Selenocyanate</a></li> <li><a href="/w/index.php?title=Tellurocyanate&action=edit&redlink=1" class="new" title="Tellurocyanate (page does not exist)">Tellurocyanate</a></li> <li><a href="/wiki/Polyester" title="Polyester">Polyester</a>, <a href="/wiki/Plastics" class="mw-redirect" title="Plastics">plastics</a> made of <a href="/wiki/Polymer" title="Polymer">polymeric</a> ester</li> <li><a href="/wiki/Oligoester" title="Oligoester">Oligoester</a>, a polymeric ester made of small number of ester <a href="/wiki/Monomer" title="Monomer">monomers</a></li> <li><a href="/wiki/Polyolester" title="Polyolester">Polyolester</a>, an ester that is a <a href="/wiki/Synthetic_oil" title="Synthetic oil">synthetic oil</a> used in refrigeration <a href="/wiki/Compressors" class="mw-redirect" title="Compressors">compressors</a></li> <li><a href="/wiki/Thioester" title="Thioester">Thioester</a></li> <li><a href="/wiki/Transesterification" title="Transesterification">Transesterification</a></li> <li><a href="/wiki/Ether_lipid" title="Ether lipid">Ether lipid</a>, an ester that is a <a href="/wiki/Lipid" title="Lipid">lipid</a> and an <a href="/wiki/Ether" title="Ether">ether</a></li> <li><a href="/wiki/Acylal" title="Acylal">Acylal</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">(R<sup class="template-chem2-sup">1</sup>−C(=O)−O−)(R<sup class="template-chem2-sup">2</sup>−C(=O)−O−)CH−R<sup class="template-chem2-sup">3</sup></span>)</li> <li><a href="/wiki/Ortho_ester" title="Ortho ester">Ortho ester</a>, an ester of an <a href="/wiki/Ortho_acid" title="Ortho acid">ortho acid</a> (e.g. esters of <a href="/wiki/Ortho_ester" title="Ortho ester">orthocarboxylic acids</a>, <a href="/wiki/Orthocarbonic_acid" title="Orthocarbonic acid">orthocarbonic acid</a>, <a href="/wiki/Orthosilicic_acid" title="Orthosilicic acid">orthosilicic acid</a>, <a href="/wiki/Orthotelluric_acid" class="mw-redirect" title="Orthotelluric acid">orthotelluric acid</a>, <a href="/wiki/Orthophosphoric_acid" class="mw-redirect" title="Orthophosphoric acid">orthophosphoric acid</a>, <a href="/wiki/Orthoboric_acid" class="mw-redirect" title="Orthoboric acid">orthoboric acid</a>, ...)</li> <li><a href="/wiki/Depside" title="Depside">Depside</a>, a polymeric ester, a type of <a href="/wiki/Polyphenol" title="Polyphenol">polyphenolic</a> compound composed of two or more monocyclic <a href="/wiki/Aromaticity" title="Aromaticity">aromatic</a> units linked by an ester group</li> <li><a href="/wiki/Depsipeptide" title="Depsipeptide">Depsipeptide</a>, a type of ester that is a <a href="/wiki/Peptide" title="Peptide">peptide</a> in which one or more of its <a href="/wiki/Amide" title="Amide">amide</a> groups (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−C(=O)−NH−</span>) are replaced by the corresponding ester groups (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−C(=O)−O−</span>)<sup id="cite_ref-GoldBookRef_33-0" class="reference"><a href="#cite_note-GoldBookRef-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup></li> <li><a href="/wiki/Glyceride" title="Glyceride">Glyceride</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">(R<sup class="template-chem2-sup">1</sup>−C(=O)−O−CH<sub class="template-chem2-sub">2</sub>−)(R<sup class="template-chem2-sup">2</sup>−C(=O)−O−CH<sub class="template-chem2-sub">2</sub>−)(R<sup class="template-chem2-sup">3</sup>−C(=O)−O−)CH</span>), an ester of <a href="/wiki/Fatty_acids" class="mw-redirect" title="Fatty acids">fatty acids</a> and <a href="/wiki/Glycerol" title="Glycerol">glycerol</a></li> <li><a href="/wiki/Lactone" title="Lactone">Lactone</a>, a cyclic carboxylic ester</li> <li><a href="/wiki/Lactide" title="Lactide">Lactide</a>, a type of lactone ester</li> <li><a href="/wiki/Vitamin_C" title="Vitamin C">Vitamin C</a> (ascorbic acid), a lactone ester, an <a href="/wiki/Nutrient#Essential_nutrients" title="Nutrient">essential nutrient</a> for humans and other animals</li> <li><a href="/wiki/Phthalide" title="Phthalide">Phthalide</a>, a type of lactone ester</li> <li><a href="/wiki/Coumarin" title="Coumarin">Coumarin</a>, a type of lactone ester</li> <li><a href="/wiki/Macrolide" title="Macrolide">Macrolide</a>, a class of natural esters that consist of a large <a href="/wiki/Macrocycle" title="Macrocycle">macrocyclic</a> lactone ring to which one or more <a href="/wiki/Deoxy_sugar" title="Deoxy sugar">deoxy sugars</a> may be attached</li> <li><a href="/wiki/Formate" title="Formate">Formate</a></li> <li><a href="/wiki/Chloroformate" title="Chloroformate">Chloroformate</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=Ester&action=edit&section=30" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist reflist-columns references-column-width" style="column-width: 30em;"> <ol class="references"> <li id="cite_note-iupac-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-iupac_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-iupac_1-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-iupac_1-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><a href="/wiki/International_Union_of_Pure_and_Applied_Chemistry" title="International Union of Pure and Applied Chemistry">IUPAC</a>, <i><a href="/wiki/IUPAC_books#Gold_Book" class="mw-redirect" title="IUPAC books">Compendium of Chemical Terminology</a></i>, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "<a rel="nofollow" class="external text" href="https://goldbook.iupac.org/terms/view/E02219.html">esters</a>". <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><a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1351%2Fgoldbook.E02219">10.1351/goldbook.E02219</a></span> </li> <li id="cite_note-Wright1986-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-Wright1986_2-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCameron_Wright1986" class="citation book cs1">Cameron Wright (1986). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=sFRZAAAAYAAJ"><i>A worker's guide to solvent hazards</i></a>. The Group. p. 48. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780969054542" title="Special:BookSources/9780969054542"><bdi>9780969054542</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=A+worker%27s+guide+to+solvent+hazards&rft.pages=48&rft.pub=The+Group&rft.date=1986&rft.isbn=9780969054542&rft.au=Cameron+Wright&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DsFRZAAAAYAAJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEster" class="Z3988"></span></span> </li> <li id="cite_note-Booser1993-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-Booser1993_3-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFE._Richard_Booser1993" class="citation book cs1">E. Richard Booser (21 December 1993). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=gnOJoug5R8IC&pg=PA237"><i>CRC Handbook of Lubrication and Tribology, Volume III: Monitoring, Materials, Synthetic Lubricants, and Applications</i></a>. 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Ester oder sauerstoffsäure Aetherarten.<br />Ethers du troisième genre.<br /><br />Viele mineralische und organische Sauerstoffsäuren treten mit einer Alkohol-Art unter Ausscheidung von Wasser zu neutralen flüchtigen ätherischen Verbindungen zusammen, welche man als gepaarte Verbindungen von Alkohol und Säuren-Wasser oder, nach der Radicaltheorie, als Salze betrachten kann, in welchen eine Säure mit einem Aether verbunden ist.</i></span></p></blockquote>Translation:<blockquote><p>b. Ester or oxy-acid ethers.<br />Ethers of the third type.<br /><br />Many mineral and organic acids containing oxygen combine with an alcohol upon elimination of water to [form] neutral, volatile ether compounds, which one can view as coupled compounds of alcohol and acid-water, or, according to the theory of radicals, as salts in which an acid is bonded with an ether. </p></blockquote></span> </li> <li id="cite_note-March-7"><span class="mw-cite-backlink">^ <a href="#cite_ref-March_7-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-March_7-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text">March, J. <i>Advanced Organic Chemistry</i> 4th Ed. J. 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"A direct conversion of esters to nitriles". <i>Tetrahedron Letters</i>. <b>20</b> (51): 4907. <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%2FS0040-4039%2801%2986746-0">10.1016/S0040-4039(01)86746-0</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Tetrahedron+Letters&rft.atitle=A+direct+conversion+of+esters+to+nitriles&rft.volume=20&rft.issue=51&rft.pages=4907&rft.date=1979&rft_id=info%3Adoi%2F10.1016%2FS0040-4039%2801%2986746-0&rft.aulast=Wood&rft.aufirst=J.+L.&rft.au=Khatri%2C+N.+A.&rft.au=Weinreb%2C+S.+M.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEster" class="Z3988"></span></span> </li> <li id="cite_note-32"><span class="mw-cite-backlink"><b><a href="#cite_ref-32">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPantenSurburg2015" class="citation book cs1">Panten, Johannes; Surburg, Horst (2015). "Flavors and Fragrances, 2. Aliphatic Compounds". <i>Ullmann's Encyclopedia of Industrial Chemistry</i>. pp. 1–55. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F14356007.t11_t01">10.1002/14356007.t11_t01</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-527-30673-2" title="Special:BookSources/978-3-527-30673-2"><bdi>978-3-527-30673-2</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Flavors+and+Fragrances%2C+2.+Aliphatic+Compounds&rft.btitle=Ullmann%27s+Encyclopedia+of+Industrial+Chemistry&rft.pages=1-55&rft.date=2015&rft_id=info%3Adoi%2F10.1002%2F14356007.t11_t01&rft.isbn=978-3-527-30673-2&rft.aulast=Panten&rft.aufirst=Johannes&rft.au=Surburg%2C+Horst&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEster" class="Z3988"></span></span> </li> <li id="cite_note-GoldBookRef-33"><span class="mw-cite-backlink"><b><a href="#cite_ref-GoldBookRef_33-0">^</a></b></span> <span class="reference-text"><a href="/wiki/International_Union_of_Pure_and_Applied_Chemistry" title="International Union of Pure and Applied Chemistry">IUPAC</a>, <i><a href="/wiki/IUPAC_books#Gold_Book" class="mw-redirect" title="IUPAC books">Compendium of Chemical Terminology</a></i>, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "<a rel="nofollow" class="external text" href="https://goldbook.iupac.org/terms/view/D01604.html">depsipeptides</a>". <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1351%2Fgoldbook.D01604">10.1351/goldbook.D01604</a></span> </li> </ol></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=Ester&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 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abbr{color:var(--color-base)!important}@media(prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}}@media print{.mw-parser-output .navbar{display:none!important}}</style><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Functional_groups" title="Template:Functional groups"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Functional_groups" title="Template talk:Functional groups"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Functional_groups" title="Special:EditPage/Template:Functional groups"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Functional_groups" style="font-size:114%;margin:0 4em"><a href="/wiki/Functional_group" title="Functional group">Functional groups</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Hydrocarbon" title="Hydrocarbon">Hydrocarbons</a> <br /><span class="nobold">(only C and H)</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Alkyl" class="mw-redirect" title="Alkyl">Alkyl</a> <ul><li><a href="/wiki/Methyl_group" title="Methyl group">Methyl</a></li> <li><a href="/wiki/Ethyl_group" title="Ethyl group">Ethyl</a></li> <li><a href="/wiki/Propyl_group" title="Propyl group">Propyl</a></li> <li><a href="/wiki/Cyclopropyl" class="mw-redirect" title="Cyclopropyl">Cyclopropyl</a></li> <li><a href="/wiki/Butyl_group" title="Butyl group">Butyl</a></li> <li><a href="/wiki/Pentyl_group" title="Pentyl group">Pentyl</a></li></ul></li> <li><a href="/wiki/Methylene_group" title="Methylene group">Methylene</a> <ul><li><a href="/wiki/Methylene_bridge" title="Methylene bridge">Bridge</a></li> <li><a href="/wiki/Methine_group" title="Methine group">Methine</a></li></ul></li> <li><a href="/wiki/Alkene" title="Alkene">Alkene</a> <ul><li><a href="/wiki/Vinyl_group" title="Vinyl group">Vinyl</a></li> <li><a href="/wiki/Allyl_group" title="Allyl group">Allyl</a></li> <li><a href="/wiki/Propenyl" title="Propenyl">1-Propenyl</a></li> <li><a href="/wiki/Crotyl_group" title="Crotyl group">Crotyl</a></li> <li><a href="/wiki/Allenes" title="Allenes">Allene</a></li> <li><a href="/wiki/Cumulene" title="Cumulene">Cumulene</a></li></ul></li> <li><a href="/wiki/Aryl" class="mw-redirect" title="Aryl">Aryl</a> <ul><li><a href="/wiki/Phenyl_group" title="Phenyl group">Phenyl</a></li> <li><a href="/wiki/Benzyl_group" title="Benzyl group">Benzyl</a></li></ul></li> <li><a href="/wiki/Alkyne" title="Alkyne">Alkyne</a></li> <li><a href="/wiki/Carbene" title="Carbene">Carbene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Only <a href="/wiki/Carbon" title="Carbon">carbon</a>, <br /><a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a>, <br />and <a href="/wiki/Oxygen" title="Oxygen">oxygen</a> <br /><span class="nobold">(only C, H and O)</span></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%">R-O-R</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/Acetal" title="Acetal">Acetal</a></li> <li><a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">Alcohol</a></li> <li><a href="/wiki/Alkoxy_group" title="Alkoxy group">Alkoxy</a> <ul><li><a href="/wiki/Methoxy_group" title="Methoxy group">Methoxy</a></li></ul></li> <li><a href="/wiki/Ether" title="Ether">Ether</a> <ul><li><a href="/wiki/Enol_ether" title="Enol ether">Enol ether</a></li> <li><a href="/wiki/Epoxide" title="Epoxide">Epoxide</a></li></ul></li> <li><a href="/wiki/Organic_peroxides" title="Organic peroxides">Peroxy</a> <ul><li><a href="/wiki/Hydroperoxide" title="Hydroperoxide">Hydroperoxy</a></li> <li><a href="/wiki/Dioxirane" title="Dioxirane">Dioxiranes</a></li></ul></li> <li><a href="/wiki/Ethylenedioxy" title="Ethylenedioxy">Ethylenedioxy</a></li> <li><a href="/wiki/Methylenedioxy" title="Methylenedioxy">Methylenedioxy</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Carbonyl_group" title="Carbonyl group">carbonyl</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/Acyl_group" title="Acyl group">Acyl</a> <ul><li><a href="/wiki/Acetyl_group" title="Acetyl group">Acetyl</a></li> <li><a href="/wiki/Acryloyl_group" class="mw-redirect" title="Acryloyl group">Acryloyl</a></li> <li><a href="/wiki/Benzoyl_group" title="Benzoyl group">Benzoyl</a></li></ul></li> <li><a href="/wiki/Aldehyde" title="Aldehyde">Aldehyde</a> <ul><li><a href="/wiki/Ketene" title="Ketene">Ketene</a></li></ul></li> <li><a href="/wiki/Ketone" title="Ketone">Ketone</a></li> <li><a href="/wiki/Ynone" title="Ynone">Ynone</a></li> <li><a href="/wiki/Reductone" title="Reductone">Reductone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">carboxy</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/Carboxylic_acid" title="Carboxylic acid">Carboxyl</a> <ul><li><a href="/wiki/Acetoxy_group" title="Acetoxy group">Acetoxy</a></li> <li><a href="/wiki/Carboxylic_anhydride" class="mw-redirect" title="Carboxylic anhydride">Anhydride</a></li></ul></li> <li><a class="mw-selflink selflink">Ester</a> <ul><li><a href="/wiki/Orthoester" class="mw-redirect" title="Orthoester">Orthoester</a></li></ul></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Only one <br />element, <br />not being <br />carbon, <br />hydrogen, <br />or oxygen <br /><span class="nobold">(one element, <br />not C, H or O)</span></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/Nitrogen" title="Nitrogen">Nitrogen</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/Amine" title="Amine">Amine</a> <ul><li><a href="/wiki/Enamine" title="Enamine">Enamine</a></li> <li><a href="/wiki/Quaternary_ammonium_cation" title="Quaternary ammonium cation">Ammonium</a></li></ul></li> <li><a href="/wiki/Hydrazines" title="Hydrazines">Hydrazo</a></li> <li><a href="/wiki/Nitrene" title="Nitrene">Nitrene</a></li> <li><a href="/wiki/Imine" title="Imine">Imine</a></li> <li><a href="/wiki/Oxime" title="Oxime">Oxime</a></li> <li><a href="/wiki/Hydrazone" title="Hydrazone">Hydrazone</a></li> <li><a href="/wiki/Azo_compound" title="Azo compound">Azo</a></li> <li><a href="/wiki/Amide_(functional_group)" title="Amide (functional group)">Amide</a></li> <li><a href="/wiki/Imidate" class="mw-redirect" title="Imidate">Imidate</a></li> <li><a href="/wiki/Amidine" title="Amidine">Amidine</a></li> <li><a href="/wiki/Carbamate" title="Carbamate">Carbamate</a></li> <li><a href="/wiki/Imide" title="Imide">Imide</a></li> <li><a href="/wiki/Nitrile" title="Nitrile">Nitrile</a></li> <li><a href="/wiki/Isocyanide" title="Isocyanide">Isonitrile</a></li> <li><a href="/wiki/Cyanate_ester" title="Cyanate ester">Cyanate</a></li> <li><a href="/wiki/Isocyanate" title="Isocyanate">Isocyanate</a></li> <li><a href="/wiki/Nitrate_ester" title="Nitrate ester">Nitrate</a></li> <li><a href="/wiki/Nitrite_ester" class="mw-redirect" title="Nitrite ester">Nitrite</a></li> <li><a href="/wiki/Nitro_compound" title="Nitro compound">Nitro</a></li> <li><a href="/wiki/Nitroso" title="Nitroso">Nitroso</a></li> <li><a href="/wiki/NONOate" title="NONOate">NONOate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phosphorus" title="Phosphorus">Phosphorus</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/Organophosphate" title="Organophosphate">Phosphate</a> <ul><li><a href="/wiki/Phosphodiester" class="mw-redirect" title="Phosphodiester">Phosphodiester</a></li></ul></li> <li><a href="/wiki/Phosphonate" title="Phosphonate">Phosphonate</a> <ul><li><a href="/wiki/Phosphite_ester" title="Phosphite ester">Phosphite</a></li></ul></li> <li><a href="/wiki/Phosphonite" title="Phosphonite">Phosphonous</a></li> <li><a href="/wiki/Phosphinate" title="Phosphinate">Phosphinate</a></li> <li><a href="/wiki/Phosphine_oxide" title="Phosphine oxide">Phosphine oxide</a></li> <li><a href="/wiki/Organophosphine" title="Organophosphine">Phosphine</a> <ul><li><a href="/wiki/Phosphonium" title="Phosphonium">Phosphonium</a></li></ul></li> <li><a href="/wiki/Phosphaalkene" title="Phosphaalkene">Phosphaalkene</a></li> <li><a href="/wiki/Phosphaalkyne" title="Phosphaalkyne">Phosphaalkyne</a></li> <li><a href="/wiki/1-Phosphaallenes" title="1-Phosphaallenes">Phosphaallene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Sulfur" title="Sulfur">Sulfur</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/Thiol" title="Thiol">Thiol</a></li> <li><a href="/wiki/Sulfide_(organic)" class="mw-redirect" title="Sulfide (organic)">Sulfide</a> <ul><li><a href="/wiki/Sulfonium" title="Sulfonium">Sulfonium</a></li></ul></li> <li><a href="/wiki/Persulfide" title="Persulfide">Persulfide</a></li> <li><a href="/wiki/Disulfide" title="Disulfide">Disulfide</a></li> <li><a href="/wiki/Sulfenic_acid" title="Sulfenic acid">Sulfenic acid</a></li> <li><a href="/wiki/Thiosulfinate" title="Thiosulfinate">Thiosulfinate</a></li> <li><a href="/wiki/Sulfoxide" title="Sulfoxide">Sulfoxide</a></li> <li><a href="/wiki/Thiosulfonate" title="Thiosulfonate">Thiosulfonate</a></li> <li><a href="/wiki/Sulfinic_acid" title="Sulfinic acid">Sulfinic acid</a></li> <li><a href="/wiki/Sulfone" title="Sulfone">Sulfone</a></li> <li><a href="/wiki/Sulfonic_acid" title="Sulfonic acid">Sulfonic acid</a></li> <li><a href="/wiki/Thioketone" title="Thioketone">Thioketone</a></li> <li><a href="/wiki/Thial" title="Thial">Thial</a></li> <li><a href="/wiki/Thioester" title="Thioester">Thioester</a></li> <li><a href="/wiki/Thionoester" class="mw-redirect" title="Thionoester">Thionoester</a></li> <li><a href="/wiki/Thioxanthate" title="Thioxanthate">Thioxanthate</a></li> <li><a href="/wiki/Xanthate" title="Xanthate">Xanthate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Boron" title="Boron">Boron</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/Boronic_acid" title="Boronic acid">Boronic acid</a></li> <li><a href="/wiki/Borinic_acid" title="Borinic acid">Borinic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Selenium" title="Selenium">Selenium</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/Selenol" title="Selenol">Selenol</a></li> <li><a href="/wiki/Selenonic_acid" title="Selenonic acid">Selenonic acid</a></li> <li><a href="/wiki/Seleninic_acid" title="Seleninic acid">Seleninic acid</a></li> <li><a href="/wiki/Selenenic_acid" title="Selenenic acid">Selenenic acid</a></li> <li><a href="/wiki/Selone" title="Selone">Selone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Tellurium" title="Tellurium">Tellurium</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/Tellurol" title="Tellurol">Tellurol</a></li> <li><a href="/wiki/Telluroketone" title="Telluroketone">Telluroketone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><i><a href="/wiki/Halocarbon" title="Halocarbon">Halo</a></i></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/Haloalkane" title="Haloalkane">Haloalkane</a> <ul><li><a href="/wiki/Fluoroethyl" title="Fluoroethyl">Fluoroethyl</a></li> <li><a href="/wiki/Trifluoromethyl" class="mw-redirect" title="Trifluoromethyl">Trifluoromethyl</a></li> <li><a href="/wiki/Trichloromethyl_group" title="Trichloromethyl group">Trichloromethyl</a></li> <li><a href="/wiki/Trifluoromethoxy_group" title="Trifluoromethoxy group">Trifluoromethoxy</a></li> <li><a href="/wiki/Iodane" class="mw-redirect" title="Iodane">Hypervalent iodine</a></li></ul></li> <li><a href="/wiki/Vinyl_halide" title="Vinyl halide">Vinyl halide</a> <ul><li><a href="/wiki/Vinyl_iodide_functional_group" title="Vinyl iodide functional group">Iodide</a></li></ul></li> <li><a href="/wiki/Acyl_halide" title="Acyl halide">Acyl halide</a> <ul><li><a href="/wiki/Acyl_chloride" title="Acyl chloride">Chloride</a></li></ul></li> <li><a href="/wiki/Perchlorate_ester" class="mw-redirect" title="Perchlorate ester">Perchlorate</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Isothiocyanate" title="Isothiocyanate">Isothiocyanate</a></li> <li><a href="/wiki/Phosphoramides" title="Phosphoramides">Phosphoramides</a></li> <li><a href="/wiki/Sulfenyl_chloride" title="Sulfenyl chloride">Sulfenyl chloride</a></li> <li><a href="/wiki/Sulfonamide" title="Sulfonamide">Sulfonamide</a></li> <li><a href="/wiki/Organic_thiocyanates" title="Organic thiocyanates">Thiocyanate</a></li> <li><a href="/wiki/Sulfinylamine" title="Sulfinylamine">Sulfinylamines</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt><span class="nobold">See also</span></dt> <dd><i><a href="/wiki/Chemical_classification" class="mw-redirect" title="Chemical classification">chemical classification</a></i></dd> <dd><i><a href="/wiki/Chemical_nomenclature" title="Chemical nomenclature">chemical nomenclature</a></i> <dl><dd><a href="/wiki/IUPAC_nomenclature_of_inorganic_chemistry" title="IUPAC nomenclature of inorganic chemistry">inorganic</a></dd> <dd><a href="/wiki/IUPAC_nomenclature_of_organic_chemistry" title="IUPAC nomenclature of organic chemistry">organic</a></dd></dl></dd></dl> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"><style data-mw-deduplicate="TemplateStyles:r1038841319">.mw-parser-output .tooltip-dotted{border-bottom:1px dotted;cursor:help}</style><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1038841319"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1038841319"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1038841319"><link rel="mw-deduplicated-inline-style" 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