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vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Chemical_characteristics"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>Chemical characteristics</span> </div> </a> <ul id="toc-Chemical_characteristics-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Biochemistry" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Biochemistry"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Biochemistry</span> </div> </a> <button aria-controls="toc-Biochemistry-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 Biochemistry subsection</span> </button> <ul id="toc-Biochemistry-sublist" class="vector-toc-list"> <li id="toc-Citric_acid_cycle" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Citric_acid_cycle"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.1</span> <span>Citric acid cycle</span> </div> </a> <ul id="toc-Citric_acid_cycle-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Other_biological_roles" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Other_biological_roles"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.2</span> <span>Other biological roles</span> </div> </a> <ul id="toc-Other_biological_roles-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Applications" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Applications"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Applications</span> </div> </a> <button aria-controls="toc-Applications-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 Applications subsection</span> </button> <ul id="toc-Applications-sublist" class="vector-toc-list"> <li id="toc-Food_and_drink" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Food_and_drink"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.1</span> <span>Food and drink</span> </div> </a> <ul id="toc-Food_and_drink-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Cleaning_and_chelating_agent" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Cleaning_and_chelating_agent"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.2</span> <span>Cleaning and chelating agent</span> </div> </a> <ul id="toc-Cleaning_and_chelating_agent-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Cosmetics,_pharmaceuticals,_dietary_supplements,_and_foods" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Cosmetics,_pharmaceuticals,_dietary_supplements,_and_foods"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.3</span> <span>Cosmetics, pharmaceuticals, dietary supplements, and foods</span> </div> </a> <ul id="toc-Cosmetics,_pharmaceuticals,_dietary_supplements,_and_foods-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Other_uses" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Other_uses"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.4</span> <span>Other uses</span> </div> </a> <ul id="toc-Other_uses-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Synthesis_of_other_organic_compounds" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Synthesis_of_other_organic_compounds"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Synthesis of other organic compounds</span> </div> </a> <ul id="toc-Synthesis_of_other_organic_compounds-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Safety" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Safety"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Safety</span> </div> </a> <ul id="toc-Safety-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Compendial_status" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Compendial_status"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Compendial status</span> </div> </a> <ul id="toc-Compendial_status-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <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-Explanatory_notes" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Explanatory_notes"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>Explanatory notes</span> </div> </a> <ul id="toc-Explanatory_notes-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">10</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">11</span> <span>External links</span> </div> </a> <ul id="toc-External_links-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header 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">Citric acid</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 76 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-76" 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">76 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/Sitroensuur" title="Sitroensuur – Afrikaans" lang="af" hreflang="af" data-title="Sitroensuur" 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%AD%D9%85%D8%B6_%D8%A7%D9%84%D9%84%D9%8A%D9%85%D9%88%D9%86" title="حمض الليمون – Arabic" lang="ar" hreflang="ar" data-title="حمض الليمون" 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%81cidu_c%C3%ADtrico" title="Ácidu cítrico – Asturian" lang="ast" hreflang="ast" data-title="Ácidu cítrico" 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/Limon_tur%C5%9Fusu" title="Limon turşusu – Azerbaijani" lang="az" hreflang="az" data-title="Limon turşusu" data-language-autonym="Azərbaycanca" data-language-local-name="Azerbaijani" class="interlanguage-link-target"><span>Azərbaycanca</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D8%B3%DB%8C%D8%AA%D8%B1%DB%8C%DA%A9_%D8%A7%D8%B3%DB%8C%D8%AF" title="سیتریک اسید – South Azerbaijani" lang="azb" hreflang="azb" data-title="سیتریک اسید" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-bn mw-list-item"><a href="https://bn.wikipedia.org/wiki/%E0%A6%B8%E0%A6%BE%E0%A6%87%E0%A6%9F%E0%A7%8D%E0%A6%B0%E0%A6%BF%E0%A6%95_%E0%A6%85%E0%A7%8D%E0%A6%AF%E0%A6%BE%E0%A6%B8%E0%A6%BF%E0%A6%A1" title="সাইট্রিক অ্যাসিড – Bangla" lang="bn" hreflang="bn" data-title="সাইট্রিক অ্যাসিড" data-language-autonym="বাংলা" data-language-local-name="Bangla" class="interlanguage-link-target"><span>বাংলা</span></a></li><li class="interlanguage-link interwiki-zh-min-nan mw-list-item"><a href="https://zh-min-nan.wikipedia.org/wiki/L%C3%AAng-sng" title="Lêng-sng – Minnan" lang="nan" hreflang="nan" data-title="Lêng-sng" 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%9B%D1%96%D0%BC%D0%BE%D0%BD%D0%BD%D0%B0%D1%8F_%D0%BA%D1%96%D1%81%D0%BB%D0%B0%D1%82%D0%B0" title="Лімонная кіслата – Belarusian" lang="be" hreflang="be" data-title="Лімонная кіслата" 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%A6%D1%8B%D1%82%D1%80%D1%8B%D0%BD%D0%B0%D0%B2%D0%B0%D1%8F_%D0%BA%D1%96%D1%81%D1%8C%D0%BB%D1%8F" title="Цытрынавая кісьля – Belarusian (Taraškievica orthography)" lang="be-tarask" hreflang="be-tarask" data-title="Цытрынавая кісьля" 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-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%9B%D0%B8%D0%BC%D0%BE%D0%BD%D0%B5%D0%BD%D0%B0_%D0%BA%D0%B8%D1%81%D0%B5%D0%BB%D0%B8%D0%BD%D0%B0" title="Лимонена киселина – Bulgarian" lang="bg" hreflang="bg" data-title="Лимонена киселина" 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/Limunska_kiselina" title="Limunska kiselina – Bosnian" lang="bs" hreflang="bs" data-title="Limunska kiselina" 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%80cid_c%C3%ADtric" title="Àcid cítric – Catalan" lang="ca" hreflang="ca" data-title="Àcid cítric" 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/Kyselina_citronov%C3%A1" title="Kyselina citronová – Czech" lang="cs" hreflang="cs" data-title="Kyselina citronová" 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/Asid_sitrig" title="Asid sitrig – Welsh" lang="cy" hreflang="cy" data-title="Asid sitrig" 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/Citronsyre" title="Citronsyre – Danish" lang="da" hreflang="da" data-title="Citronsyre" 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/Citronens%C3%A4ure" title="Citronensäure – German" lang="de" hreflang="de" data-title="Citronensäure" 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/Sidrunhape" title="Sidrunhape – Estonian" lang="et" hreflang="et" data-title="Sidrunhape" 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%9A%CE%B9%CF%84%CF%81%CE%B9%CE%BA%CF%8C_%CE%BF%CE%BE%CF%8D" title="Κιτρικό οξύ – Greek" lang="el" hreflang="el" data-title="Κιτρικό οξύ" 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%81cido_c%C3%ADtrico" title="Ácido cítrico – Spanish" lang="es" hreflang="es" data-title="Ácido cítrico" 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/Citrato" title="Citrato – Esperanto" lang="eo" hreflang="eo" data-title="Citrato" 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/Azido_zitriko" title="Azido zitriko – Basque" lang="eu" hreflang="eu" data-title="Azido zitriko" 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%B3%DB%8C%D8%AA%D8%B1%DB%8C%DA%A9_%D8%A7%D8%B3%DB%8C%D8%AF" title="سیتریک اسید – Persian" lang="fa" hreflang="fa" data-title="سیتریک اسید" 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/Acide_citrique" title="Acide citrique – French" lang="fr" hreflang="fr" data-title="Acide citrique" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ga mw-list-item"><a href="https://ga.wikipedia.org/wiki/Aig%C3%A9ad_citreach" title="Aigéad citreach – Irish" lang="ga" hreflang="ga" data-title="Aigéad citreach" 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%81cido_c%C3%ADtrico" title="Ácido cítrico – Galician" lang="gl" hreflang="gl" data-title="Ácido cítrico" 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%8B%9C%ED%8A%B8%EB%A5%B4%EC%82%B0" title="시트르산 – Korean" lang="ko" hreflang="ko" data-title="시트르산" 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%BF%D5%AB%D5%BF%D6%80%D5%B8%D5%B6%D5%A1%D5%A9%D5%A9%D5%B8%D6%82" title="Կիտրոնաթթու – Armenian" lang="hy" hreflang="hy" data-title="Կիտրոնաթթու" 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%B8%E0%A4%BF%E0%A4%9F%E0%A5%8D%E0%A4%B0%E0%A4%BF%E0%A4%95_%E0%A4%85%E0%A4%AE%E0%A5%8D%E0%A4%B2" title="सिट्रिक अम्ल – Hindi" lang="hi" hreflang="hi" data-title="सिट्रिक अम्ल" 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/Limunska_kiselina" title="Limunska kiselina – Croatian" lang="hr" hreflang="hr" data-title="Limunska kiselina" 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/Asam_sitrat" title="Asam sitrat – Indonesian" lang="id" hreflang="id" data-title="Asam sitrat" 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/S%C3%ADtr%C3%B3nus%C3%BDra" title="Sítrónusýra – Icelandic" lang="is" hreflang="is" data-title="Sítrónusýra" 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/Acido_citrico" title="Acido citrico – Italian" lang="it" hreflang="it" data-title="Acido citrico" 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%97%D7%95%D7%9E%D7%A6%D7%94_%D7%A6%D7%99%D7%98%D7%A8%D7%99%D7%AA" title="חומצה ציטרית – Hebrew" lang="he" hreflang="he" data-title="חומצה ציטרית" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-jv mw-list-item"><a href="https://jv.wikipedia.org/wiki/Asem_sitrat" title="Asem sitrat – Javanese" lang="jv" hreflang="jv" data-title="Asem sitrat" data-language-autonym="Jawa" data-language-local-name="Javanese" class="interlanguage-link-target"><span>Jawa</span></a></li><li class="interlanguage-link interwiki-kn mw-list-item"><a href="https://kn.wikipedia.org/wiki/%E0%B2%B8%E0%B2%BF%E0%B2%9F%E0%B3%8D%E0%B2%B0%E0%B2%BF%E0%B2%95%E0%B3%8D_%E0%B2%86%E0%B2%AE%E0%B3%8D%E0%B2%B2" title="ಸಿಟ್ರಿಕ್ ಆಮ್ಲ – Kannada" lang="kn" hreflang="kn" data-title="ಸಿಟ್ರಿಕ್ ಆಮ್ಲ" data-language-autonym="ಕನ್ನಡ" data-language-local-name="Kannada" class="interlanguage-link-target"><span>ಕನ್ನಡ</span></a></li><li class="interlanguage-link interwiki-ka mw-list-item"><a href="https://ka.wikipedia.org/wiki/%E1%83%9A%E1%83%98%E1%83%9B%E1%83%9D%E1%83%9C%E1%83%9B%E1%83%9F%E1%83%90%E1%83%95%E1%83%90" title="ლიმონმჟავა – Georgian" lang="ka" hreflang="ka" data-title="ლიმონმჟავა" data-language-autonym="ქართული" data-language-local-name="Georgian" class="interlanguage-link-target"><span>ქართული</span></a></li><li class="interlanguage-link interwiki-kk mw-list-item"><a href="https://kk.wikipedia.org/wiki/%D0%9B%D0%B8%D0%BC%D0%BE%D0%BD_%D2%9B%D1%8B%D1%88%D2%9B%D1%8B%D0%BB%D1%8B" title="Лимон қышқылы – Kazakh" lang="kk" hreflang="kk" data-title="Лимон қышқылы" data-language-autonym="Қазақша" data-language-local-name="Kazakh" class="interlanguage-link-target"><span>Қазақша</span></a></li><li class="interlanguage-link interwiki-ky mw-list-item"><a href="https://ky.wikipedia.org/wiki/%D0%9B%D0%B8%D0%BC%D0%BE%D0%BD_%D0%BA%D0%B8%D1%81%D0%BB%D0%BE%D1%82%D0%B0%D1%81%D1%8B" title="Лимон кислотасы – Kyrgyz" lang="ky" hreflang="ky" data-title="Лимон кислотасы" data-language-autonym="Кыргызча" data-language-local-name="Kyrgyz" class="interlanguage-link-target"><span>Кыргызча</span></a></li><li class="interlanguage-link interwiki-la mw-list-item"><a href="https://la.wikipedia.org/wiki/Acidum_citricum" title="Acidum citricum – Latin" lang="la" hreflang="la" data-title="Acidum citricum" 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/Citronsk%C4%81be" title="Citronskābe – Latvian" lang="lv" hreflang="lv" data-title="Citronskābe" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target"><span>Latviešu</span></a></li><li class="interlanguage-link interwiki-lb mw-list-item"><a href="https://lb.wikipedia.org/wiki/Zitrounesaier" title="Zitrounesaier – Luxembourgish" lang="lb" hreflang="lb" data-title="Zitrounesaier" data-language-autonym="Lëtzebuergesch" data-language-local-name="Luxembourgish" class="interlanguage-link-target"><span>Lëtzebuergesch</span></a></li><li class="interlanguage-link interwiki-lt mw-list-item"><a href="https://lt.wikipedia.org/wiki/Citrinos_r%C5%ABg%C5%A1tis" title="Citrinos rūgštis – Lithuanian" lang="lt" hreflang="lt" data-title="Citrinos rūgštis" data-language-autonym="Lietuvių" data-language-local-name="Lithuanian" class="interlanguage-link-target"><span>Lietuvių</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Citromsav" title="Citromsav – Hungarian" lang="hu" hreflang="hu" data-title="Citromsav" 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%9B%D0%B8%D0%BC%D0%BE%D0%BD%D1%81%D0%BA%D0%B0_%D0%BA%D0%B8%D1%81%D0%B5%D0%BB%D0%B8%D0%BD%D0%B0" title="Лимонска киселина – Macedonian" lang="mk" hreflang="mk" data-title="Лимонска киселина" 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%B8%E0%B4%BF%E0%B4%9F%E0%B5%8D%E0%B4%B0%E0%B4%BF%E0%B4%95%E0%B5%8D_%E0%B4%86%E0%B4%B8%E0%B4%BF%E0%B4%A1%E0%B5%8D" title="സിട്രിക് ആസിഡ് – Malayalam" lang="ml" hreflang="ml" data-title="സിട്രിക് ആസിഡ്" 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/Asid_sitrik" title="Asid sitrik – Malay" lang="ms" hreflang="ms" data-title="Asid sitrik" 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/Citroenzuur" title="Citroenzuur – Dutch" lang="nl" hreflang="nl" data-title="Citroenzuur" 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%AF%E3%82%A8%E3%83%B3%E9%85%B8" title="クエン酸 – Japanese" lang="ja" hreflang="ja" data-title="クエン酸" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Sitronsyre" title="Sitronsyre – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Sitronsyre" 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/Sitronsyre" title="Sitronsyre – Norwegian Nynorsk" lang="nn" hreflang="nn" data-title="Sitronsyre" data-language-autonym="Norsk nynorsk" data-language-local-name="Norwegian Nynorsk" class="interlanguage-link-target"><span>Norsk nynorsk</span></a></li><li class="interlanguage-link interwiki-uz mw-list-item"><a href="https://uz.wikipedia.org/wiki/Limon_kislota" title="Limon kislota – Uzbek" lang="uz" hreflang="uz" data-title="Limon kislota" data-language-autonym="Oʻzbekcha / ўзбекча" data-language-local-name="Uzbek" class="interlanguage-link-target"><span>Oʻzbekcha / ўзбекча</span></a></li><li class="interlanguage-link interwiki-pa mw-list-item"><a href="https://pa.wikipedia.org/wiki/%E0%A8%B8%E0%A8%BF%E0%A8%9F%E0%A8%B0%E0%A8%BF%E0%A8%95_%E0%A8%A4%E0%A9%87%E0%A8%9C%E0%A8%BC%E0%A8%BE%E0%A8%AC" title="ਸਿਟਰਿਕ ਤੇਜ਼ਾਬ – Punjabi" lang="pa" hreflang="pa" data-title="ਸਿਟਰਿਕ ਤੇਜ਼ਾਬ" data-language-autonym="ਪੰਜਾਬੀ" data-language-local-name="Punjabi" class="interlanguage-link-target"><span>ਪੰਜਾਬੀ</span></a></li><li class="interlanguage-link interwiki-pnb mw-list-item"><a href="https://pnb.wikipedia.org/wiki/%D8%B3%D9%B9%D8%B1%DA%A9_%D8%AA%DB%8C%D8%B2%D8%A7%D8%A8" title="سٹرک تیزاب – Western Punjabi" lang="pnb" hreflang="pnb" data-title="سٹرک تیزاب" data-language-autonym="پنجابی" data-language-local-name="Western Punjabi" class="interlanguage-link-target"><span>پنجابی</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Kwas_cytrynowy" title="Kwas cytrynowy – Polish" lang="pl" hreflang="pl" data-title="Kwas cytrynowy" 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%81cido_c%C3%ADtrico" title="Ácido cítrico – Portuguese" lang="pt" hreflang="pt" data-title="Ácido cítrico" 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/Acid_citric" title="Acid citric – Romanian" lang="ro" hreflang="ro" data-title="Acid citric" 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%9B%D0%B8%D0%BC%D0%BE%D0%BD%D0%BD%D0%B0%D1%8F_%D0%BA%D0%B8%D1%81%D0%BB%D0%BE%D1%82%D0%B0" title="Лимонная кислота – Russian" lang="ru" hreflang="ru" data-title="Лимонная кислота" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sco mw-list-item"><a href="https://sco.wikipedia.org/wiki/Citric_acid" title="Citric acid – Scots" lang="sco" hreflang="sco" data-title="Citric acid" data-language-autonym="Scots" data-language-local-name="Scots" class="interlanguage-link-target"><span>Scots</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Citric_acid" title="Citric acid – Simple English" lang="en-simple" hreflang="en-simple" data-title="Citric acid" 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/Kyselina_citr%C3%B3nov%C3%A1" title="Kyselina citrónová – Slovak" lang="sk" hreflang="sk" data-title="Kyselina citrónová" 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/Citronska_kislina" title="Citronska kislina – Slovenian" lang="sl" hreflang="sl" data-title="Citronska kislina" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Limunska_kiselina" title="Limunska kiselina – Serbian" lang="sr" hreflang="sr" data-title="Limunska kiselina" 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/Limunska_kiselina" title="Limunska kiselina – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Limunska kiselina" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Sitruunahappo" title="Sitruunahappo – Finnish" lang="fi" hreflang="fi" data-title="Sitruunahappo" 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/Citronsyra" title="Citronsyra – Swedish" lang="sv" hreflang="sv" data-title="Citronsyra" 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%9A%E0%AE%BF%E0%AE%9F%E0%AF%8D%E0%AE%B0%E0%AE%BF%E0%AE%95%E0%AF%8D_%E0%AE%85%E0%AE%AE%E0%AE%BF%E0%AE%B2%E0%AE%AE%E0%AF%8D" title="சிட்ரிக் அமிலம் – Tamil" lang="ta" hreflang="ta" data-title="சிட்ரிக் அமிலம்" 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%B8%E0%B0%BF%E0%B0%9F%E0%B1%8D%E0%B0%B0%E0%B0%BF%E0%B0%95%E0%B1%8D_%E0%B0%86%E0%B0%AE%E0%B1%8D%E0%B0%B2%E0%B0%82" title="సిట్రిక్ ఆమ్లం – Telugu" lang="te" hreflang="te" data-title="సిట్రిక్ ఆమ్లం" data-language-autonym="తెలుగు" data-language-local-name="Telugu" class="interlanguage-link-target"><span>తెలుగు</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Sitrik_asit" title="Sitrik asit – Turkish" lang="tr" hreflang="tr" data-title="Sitrik asit" 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%9B%D0%B8%D0%BC%D0%BE%D0%BD%D0%BD%D0%B0_%D0%BA%D0%B8%D1%81%D0%BB%D0%BE%D1%82%D0%B0" title="Лимонна кислота – Ukrainian" lang="uk" hreflang="uk" data-title="Лимонна кислота" 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%B3%D8%AA_%D9%84%DB%8C%D9%85%D9%88%DA%BA" title="ست لیموں – Urdu" lang="ur" hreflang="ur" data-title="ست لیموں" 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/Acid_citric" title="Acid citric – Vietnamese" lang="vi" hreflang="vi" data-title="Acid citric" 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-wa mw-list-item"><a href="https://wa.wikipedia.org/wiki/Seur_di_citron" title="Seur di citron – Walloon" lang="wa" hreflang="wa" data-title="Seur di citron" data-language-autonym="Walon" data-language-local-name="Walloon" class="interlanguage-link-target"><span>Walon</span></a></li><li class="interlanguage-link interwiki-war mw-list-item"><a href="https://war.wikipedia.org/wiki/Aksido_Citrico" title="Aksido Citrico – Waray" lang="war" hreflang="war" data-title="Aksido Citrico" 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/%E6%9F%A0%E6%AA%AC%E9%85%B8" title="柠檬酸 – Wu" lang="wuu" hreflang="wuu" data-title="柠檬酸" 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/%E6%AA%B8%E6%AA%AC%E9%85%B8" title="檸檬酸 – Cantonese" lang="yue" hreflang="yue" data-title="檸檬酸" 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/%E6%AA%B8%E6%AA%AC%E9%85%B8" title="檸檬酸 – Chinese" lang="zh" hreflang="zh" data-title="檸檬酸" 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/Q159683#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/Citric_acid" title="View the content page [c]" accesskey="c"><span>Article</span></a></li><li id="ca-talk" class="vector-tab-noicon mw-list-item"><a href="/wiki/Talk:Citric_acid" rel="discussion" 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id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Weak organic acid</div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">"E330" redirects here. For the locomotive, see <a href="/wiki/FS_Class_E330" class="mw-redirect" title="FS Class E330">FS Class E330</a>.</div> <p> <style data-mw-deduplicate="TemplateStyles:r1084375498">.mw-parser-output .ib-chembox{border-collapse:collapse;text-align:left}.mw-parser-output .ib-chembox td,.mw-parser-output .ib-chembox th{border:1px solid #a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}</style> </p> <table class="infobox ib-chembox"> <caption>Citric acid </caption> <tbody><tr> <td colspan="2" class="borderless" style="text-align:center"> <table border="0" style="width:100%;display:inline-table;"> <tbody><tr> <td style="border-right:1px solid #aaa; width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Zitronens%C3%A4ure_-_Citric_acid.svg" class="mw-file-description" title="Stereo skeletal formula of citric acid"><img alt="Stereo skeletal formula of citric acid" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c5/Zitronens%C3%A4ure_-_Citric_acid.svg/150px-Zitronens%C3%A4ure_-_Citric_acid.svg.png" decoding="async" width="150" height="68" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c5/Zitronens%C3%A4ure_-_Citric_acid.svg/225px-Zitronens%C3%A4ure_-_Citric_acid.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c5/Zitronens%C3%A4ure_-_Citric_acid.svg/300px-Zitronens%C3%A4ure_-_Citric_acid.svg.png 2x" data-file-width="256" data-file-height="116" /></a><figcaption>Stereo skeletal formula of citric acid</figcaption></figure> </td> <td style="width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Citric-acid-3D-balls.png" class="mw-file-description" title="Ball-and-stick model of citric acid"><img alt="Ball-and-stick model of citric acid" src="//upload.wikimedia.org/wikipedia/commons/thumb/7/7a/Citric-acid-3D-balls.png/150px-Citric-acid-3D-balls.png" decoding="async" width="150" height="87" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/7a/Citric-acid-3D-balls.png/225px-Citric-acid-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/7a/Citric-acid-3D-balls.png/300px-Citric-acid-3D-balls.png 2x" data-file-width="1100" data-file-height="635" /></a><figcaption>Ball-and-stick model of citric acid</figcaption></figure> </td></tr></tbody></table> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Zitronens%C3%A4ure_Kristallzucht.jpg" class="mw-file-description" title="Crystal sample from the saturated citric acid solution."><img alt="Crystal sample from the saturated citric acid solution." src="//upload.wikimedia.org/wikipedia/commons/thumb/d/da/Zitronens%C3%A4ure_Kristallzucht.jpg/320px-Zitronens%C3%A4ure_Kristallzucht.jpg" decoding="async" width="320" height="264" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/da/Zitronens%C3%A4ure_Kristallzucht.jpg/480px-Zitronens%C3%A4ure_Kristallzucht.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/da/Zitronens%C3%A4ure_Kristallzucht.jpg/640px-Zitronens%C3%A4ure_Kristallzucht.jpg 2x" data-file-width="1822" data-file-height="1503" /></a></span> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Chemical_nomenclature" title="Chemical nomenclature">IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">Citric acid<sup id="cite_ref-IUPAC2014_1-0" class="reference"><a href="#cite_note-IUPAC2014-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup></div> </td></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Preferred_IUPAC_name" title="Preferred IUPAC name">Preferred IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;">2-Hydroxypropane-1,2,3-tricarboxylic acid<sup id="cite_ref-IUPAC2014_1-1" class="reference"><a href="#cite_note-IUPAC2014-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup></div></div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=77-92-9">77-92-9</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=OC%28%3DO%29CC%28O%29%28C%28%3DO%29O%29CC%28%3DO%29O">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=30769">CHEBI:30769</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembldb/index.php/compound/inspect/ChEMBL1261">ChEMBL1261</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.305.html">305</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/DrugBank" title="DrugBank">DrugBank</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.drugbank.ca"><a rel="nofollow" class="external text" href="https://www.drugbank.ca/drugs/DB04272">DB04272</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a> </td> <td><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.000.973">100.000.973</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q159683#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span> </td></tr> <tr> <td><a href="/wiki/European_Community_number" title="European Community number"><span title="European Community number (chemical identifier)">EC Number</span></a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>201-069-1</li></ul></div> </td></tr> <tr> <td><a href="/wiki/E_number" title="E number"><span title="E number (food additive code)">E number</span></a> </td> <td>E330 <a href="/wiki/E_number#E300–E399" title="E number">(antioxidants, ...)</a> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/IUPHAR/BPS" class="mw-redirect" title="IUPHAR/BPS">IUPHAR/BPS</a></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.guidetopharmacology.org"><a rel="nofollow" class="external text" href="http://www.guidetopharmacology.org/GRAC/LigandDisplayForward?tab=summary&ligandId=2478">2478</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/KEGG" title="KEGG">KEGG</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.kegg.jp"><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/D00037">D00037</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/311">311</a></span></li><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/22230">22230</a></span> (monohydrate)</li></ul></div> </td></tr> <tr> <td><a href="/wiki/RTECS" class="mw-redirect" title="RTECS">RTECS number</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>GE7350000</li></ul></div> </td></tr> <tr> <td><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/XF417D3PSL">XF417D3PSL</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID3020332">DTXSID3020332</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q159683#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></span></li></ul></div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/C6H8O7/c7-3(8)1-6(13,5(11)12)2-4(9)10/h13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: KRKNYBCHXYNGOX-UHFFFAOYSA-N<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div></div></li><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1/C6H8O7/c7-3(8)1-6(13,5(11)12)2-4(9)10/h13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: KRKNYBCHXYNGOX-UHFFFAOYAM</div></div></li></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">OC(=O)CC(O)(C(=O)O)CC(=O)O</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td><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">C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">8</sub>O<sub class="template-chem2-sub">7</sub></span>  </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td>192.123<span class="nowrap"> </span>g/mol (anhydrous), 210.14<span class="nowrap"> </span>g/mol (monohydrate)<sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup>    </td></tr> <tr> <td>Appearance </td> <td>white solid </td></tr> <tr> <td><a href="/wiki/Odor" title="Odor">Odor</a> </td> <td>Odorless </td></tr> <tr> <td><a href="/wiki/Density" title="Density">Density</a> </td> <td>1.665<span class="nowrap"> </span>g/cm<sup>3</sup> (anhydrous)<br /> 1.542<span class="nowrap"> </span>g/cm<sup>3</sup> (18<span class="nowrap"> </span>°C, monohydrate) </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>156 °C (313 °F; 429 K) </td></tr> <tr> <td><a href="/wiki/Boiling_point" title="Boiling point">Boiling point</a> </td> <td>310 °C (590 °F; 583 K) decomposes from 175<span class="nowrap"> </span>°C<sup id="cite_ref-chemister_3-0" class="reference"><a href="#cite_note-chemister-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Aqueous_solution" title="Aqueous solution">Solubility in water</a></div> </td> <td>54%<span class="nowrap"> </span>w/w (10<span class="nowrap"> </span>°C)<br /> 59.2%<span class="nowrap"> </span>w/w (20<span class="nowrap"> </span>°C)<br /> 64.3%<span class="nowrap"> </span>w/w (30<span class="nowrap"> </span>°C)<br /> 68.6%<span class="nowrap"> </span>w/w (40<span class="nowrap"> </span>°C)<br /> 70.9%<span class="nowrap"> </span>w/w (50<span class="nowrap"> </span>°C)<br /> 73.5%<span class="nowrap"> </span>w/w (60<span class="nowrap"> </span>°C)<br /> 76.2%<span class="nowrap"> </span>w/w (70<span class="nowrap"> </span>°C)<br /> 78.8%<span class="nowrap"> </span>w/w (80<span class="nowrap"> </span>°C)<br /> 81.4%<span class="nowrap"> </span>w/w (90<span class="nowrap"> </span>°C)<br /> 84%<span class="nowrap"> </span>w/w (100<span class="nowrap"> </span>°C)<sup id="cite_ref-pubchem_4-0" class="reference"><a href="#cite_note-pubchem-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Solubility" title="Solubility">Solubility</a> </td> <td>Soluble in <a href="/wiki/Acetone" title="Acetone">acetone</a>, <a href="/wiki/Ethanol" title="Ethanol">alcohol</a>, <a href="/wiki/Diethyl_ether" title="Diethyl ether">ether</a>, <a href="/wiki/Ethyl_acetate" title="Ethyl acetate">ethyl acetate</a>, <a href="/wiki/Dimethyl_sulfoxide" title="Dimethyl sulfoxide">DMSO</a><br /> Insoluble in <a href="/wiki/Benzene" title="Benzene"><span class="chemf nowrap">C<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">6</sub></span></span>H<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">6</sub></span></span></span></a>, <a href="/wiki/Chloroform" title="Chloroform">CHCl<sub>3</sub></a>, <a href="/wiki/Carbon_disulfide" title="Carbon disulfide">CS<sub>2</sub></a>, <a href="/wiki/Toluene" title="Toluene">toluene</a><sup id="cite_ref-chemister_3-1" class="reference"><a href="#cite_note-chemister-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Solubility" title="Solubility">Solubility</a> in <a href="/wiki/Ethanol" title="Ethanol">ethanol</a> </td> <td>62<span class="nowrap"> </span>g/100 g (25<span class="nowrap"> </span>°C)<sup id="cite_ref-chemister_3-2" class="reference"><a href="#cite_note-chemister-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Solubility" title="Solubility">Solubility</a> in <a href="/wiki/Amyl_acetate" title="Amyl acetate">amyl acetate</a> </td> <td>4.41<span class="nowrap"> </span>g/100 g (25<span class="nowrap"> </span>°C)<sup id="cite_ref-chemister_3-3" class="reference"><a href="#cite_note-chemister-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Solubility" title="Solubility">Solubility</a> in <a href="/wiki/Diethyl_ether" title="Diethyl ether">diethyl ether</a> </td> <td>1.05<span class="nowrap"> </span>g/100 g (25<span class="nowrap"> </span>°C)<sup id="cite_ref-chemister_3-4" class="reference"><a href="#cite_note-chemister-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Solubility" title="Solubility">Solubility</a> in <a href="/wiki/1,4-dioxane" class="mw-redirect" title="1,4-dioxane">1,4-dioxane</a> </td> <td>35.9<span class="nowrap"> </span>g/100 g (25<span class="nowrap"> </span>°C)<sup id="cite_ref-chemister_3-5" class="reference"><a href="#cite_note-chemister-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Partition_coefficient" title="Partition coefficient">log <i>P</i></a> </td> <td>−1.64 </td></tr> <tr> <td><a href="/wiki/Acid_dissociation_constant" title="Acid dissociation constant">Acidity</a> (p<i>K</i><sub>a</sub>) </td> <td>p<i>K</i><sub>a1</sub> = 3.13<sup id="cite_ref-sigma_5-0" class="reference"><a href="#cite_note-sigma-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><br /> p<i>K</i><sub>a2</sub> = 4.76<sup id="cite_ref-sigma_5-1" class="reference"><a href="#cite_note-sigma-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><br /> p<i>K</i><sub>a3</sub> = 6.39,<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> 6.40<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup><br />p<i>K</i><sub>a4</sub> = 14.4<sup id="cite_ref-Silva_Kong_Hider_2009_pp._771–778_8-0" class="reference"><a href="#cite_note-Silva_Kong_Hider_2009_pp._771–778-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Refractive_index" title="Refractive index">Refractive index</a> (<i>n</i><sub>D</sub>)</div> </td> <td>1.493–1.509 (20<span class="nowrap"> </span>°C)<sup id="cite_ref-pubchem_4-1" class="reference"><a href="#cite_note-pubchem-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><br /> 1.46 (150<span class="nowrap"> </span>°C)<sup id="cite_ref-chemister_3-6" class="reference"><a href="#cite_note-chemister-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Viscosity" title="Viscosity">Viscosity</a> </td> <td>6.5<span class="nowrap"> </span>cP (50% <abbr title="aqueous solution">aq. sol.</abbr>)<sup id="cite_ref-pubchem_4-2" class="reference"><a href="#cite_note-pubchem-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Structure </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Crystal_structure" title="Crystal structure">Crystal structure</a></div> </td> <td>Monoclinic </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Thermochemistry </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Heat_capacity" title="Heat capacity">Heat capacity</a> <span style="font-size:112%;">(<i>C</i>)</span></div> </td> <td>226.51<span class="nowrap"> </span>J/(mol·K) (26.85<span class="nowrap"> </span>°C)<sup id="cite_ref-nist_9-0" class="reference"><a href="#cite_note-nist-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Standard_molar_entropy" title="Standard molar entropy">Std molar<br />entropy</a> <span style="font-size:112%;">(<i>S</i><sup>⦵</sup><sub>298</sub>)</span></div> </td> <td>252.1<span class="nowrap"> </span>J/(mol·K)<sup id="cite_ref-nist_9-1" class="reference"><a href="#cite_note-nist-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Standard_enthalpy_change_of_formation" class="mw-redirect" title="Standard enthalpy change of formation">Std enthalpy of<br />formation</a> <span style="font-size:112%;">(Δ<sub>f</sub><i>H</i><sup>⦵</sup><sub>298</sub>)</span></div> </td> <td>−1543.8<span class="nowrap"> </span>kJ/mol<sup id="cite_ref-pubchem_4-3" class="reference"><a href="#cite_note-pubchem-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Heat_of_combustion#Higher_heating_value" title="Heat of combustion">Heat of combustion, higher value</a> (HHV)</div> </td> <td>1985.3 kJ/mol (474.5 kcal/mol, 2.47 kcal/g),<sup id="cite_ref-pubchem_4-4" class="reference"><a href="#cite_note-pubchem-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> 1960.6<span class="nowrap"> </span>kJ/mol<sup id="cite_ref-nist_9-2" class="reference"><a href="#cite_note-nist-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup><br /> 1972.34 kJ/mol (471.4 kcal/mol, 2.24 kcal/g) (monohydrate)<sup id="cite_ref-pubchem_4-5" class="reference"><a href="#cite_note-pubchem-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Pharmacology </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Anatomical_Therapeutic_Chemical_Classification_System" title="Anatomical Therapeutic Chemical Classification System">ATC code</a></div> </td> <td><a href="/wiki/ATC_code_A09" title="ATC code A09">A09AB04</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=A09AB04">WHO</a></span>)  </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Hazards </th></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;"><b><a href="/wiki/Occupational_safety_and_health" title="Occupational safety and health">Occupational safety and health</a></b> (OHS/OSH): </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Main hazards</div> </td> <td>Skin and eye irritant </td></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;"><a href="/wiki/Globally_Harmonized_System_of_Classification_and_Labelling_of_Chemicals" title="Globally Harmonized System of Classification and Labelling of Chemicals"><b>GHS</b> labelling</a>: </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_hazard_pictograms" title="GHS hazard pictograms">Pictograms</a></div> </td> <td><span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-acid.svg" class="mw-file-description" title="GHS05: Corrosive"><img alt="GHS05: Corrosive" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a1/GHS-pictogram-acid.svg/50px-GHS-pictogram-acid.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a1/GHS-pictogram-acid.svg/75px-GHS-pictogram-acid.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a1/GHS-pictogram-acid.svg/100px-GHS-pictogram-acid.svg.png 2x" data-file-width="724" data-file-height="724" /></a></span><span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-exclam.svg" class="mw-file-description" title="GHS07: Exclamation mark"><img alt="GHS07: Exclamation mark" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/50px-GHS-pictogram-exclam.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/75px-GHS-pictogram-exclam.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/100px-GHS-pictogram-exclam.svg.png 2x" data-file-width="512" data-file-height="512" /></a></span><sup id="cite_ref-sigma_5-2" class="reference"><a href="#cite_note-sigma-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Globally_Harmonized_System_of_Classification_and_Labelling_of_Chemicals#Signal_word" title="Globally Harmonized System of Classification and Labelling of Chemicals">Signal word</a></div> </td> <td><b>Warning</b> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_hazard_statements" title="GHS hazard statements">Hazard statements</a></div> </td> <td><abbr class="abbr" title="H290: May be corrosive to metals">H290</abbr>, <abbr class="abbr" title="H319: Causes serious eye irritation">H319</abbr>, <abbr class="abbr" title="H315: Causes skin irritation">H315</abbr><sup id="cite_ref-sigma_5-3" class="reference"><a href="#cite_note-sigma-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_precautionary_statements" title="GHS precautionary statements">Precautionary statements</a></div> </td> <td><abbr class="abbr" title="P305+P351+P338: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do. Continue rinsing.">P305+P351+P338</abbr><sup id="cite_ref-sigma_5-4" class="reference"><a href="#cite_note-sigma-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/NFPA_704" title="NFPA 704"><b>NFPA 704</b></a> (fire diamond) </td> <td><style data-mw-deduplicate="TemplateStyles:r1170367383">.mw-parser-output .nfpa-704-diamond-ref{float:right;padding:1px;text-align:right}.mw-parser-output .nfpa-704-diamond-container{width:82px;font-family:sans-serif;margin:0 auto}.mw-parser-output .nfpa-704-diamond-container-ref{float:left;margin-left:1em}.mw-parser-output .nfpa-704-diamond-images{float:left;font-size:20px;text-align:center;position:relative;height:80px;width:80px;padding:1px}.mw-parser-output .nfpa-704-diamond-map{position:absolute;height:80px;width:80px}.mw-parser-output .nfpa-704-diamond .noresize{margin:0 auto}.mw-parser-output .nfpa-704-diamond-code{line-height:1em;text-align:center;position:absolute}.mw-parser-output .nfpa-704-diamond-code>a{color:black}.mw-parser-output .nfpa-704-diamond-blue{width:13px;top:31px;left:15px}.mw-parser-output .nfpa-704-diamond-red{width:12px;top:12px;left:35px}.mw-parser-output .nfpa-704-diamond-yellow{width:13px;top:31px;left:54px}.mw-parser-output .nfpa-704-diamond-white-image{position:relative;top:51px;left:0}.mw-parser-output .nfpa-704-diamond-white-text{vertical-align:middle;text-align:center;line-height:80%;position:absolute;top:52px}.mw-parser-output .nfpa-704-diamond-white-text a>span{position:absolute;color:black}.mw-parser-output .nfpa-704-diamond-white-wors{font-size:15px;width:23px;left:29px}.mw-parser-output .nfpa-704-diamond-white-wox{font-size:15px;font-stretch:condensed;width:21px;line-height:80%;top:-4px;left:29px}.mw-parser-output .nfpa-704-diamond-white-abcp{font-size:13.5px;font-stretch:condensed;width:28px;left:26px}.mw-parser-output .nfpa-704-diamond-white-ac{font-size:10px;width:30px;left:25px}.mw-parser-output .nfpa-704-diamond-white-strike{text-decoration:line-through}</style><div class="nfpa-704-diamond notheme"><div class="nfpa-704-diamond-container"><div class="nfpa-704-diamond-images nounderlines"> <div class="nfpa-704-diamond-map"><figure class="noresize" typeof="mw:File"><span><img alt="NFPA 704 four-colored diamond" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/80px-NFPA_704.svg.png" decoding="async" width="80" height="80" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/120px-NFPA_704.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/160px-NFPA_704.svg.png 2x" data-file-width="512" data-file-height="512" usemap="#ImageMap_482e25fdfe95519d" /></span><map name="ImageMap_482e25fdfe95519d"><area href="/wiki/NFPA_704#Blue" shape="poly" coords="23,23,47,47,23,70,0,47" alt="Health 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroform" title="Health 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroform" /><area href="/wiki/NFPA_704#Red" shape="poly" coords="47,0,70,23,47,47,23,23" alt="Flammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oil" title="Flammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oil" /><area href="/wiki/NFPA_704#Yellow" shape="poly" coords="70,23,94,47,70,70,47,47" alt="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" title="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" /><area href="/wiki/NFPA_704#White" shape="poly" coords="47,47,70,70,47,94,23,70" alt="Special hazards (white): no code" title="Special hazards (white): no code" /></map><figcaption></figcaption></figure></div><div class="nfpa-704-diamond-code nfpa-704-diamond-blue"> <a href="/wiki/NFPA_704#Blue" title="NFPA 704"><span title="Health 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroform" class="notheme mw-no-invert">2</span></a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-red"> <a href="/wiki/NFPA_704#Red" title="NFPA 704"><span title="Flammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oil" class="notheme mw-no-invert">1</span></a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-yellow"> <a href="/wiki/NFPA_704#Yellow" title="NFPA 704"><span title="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" class="notheme mw-no-invert">0</span></a></div></div></div></div> </td></tr> <tr> <td><a href="/wiki/Flash_point" title="Flash point">Flash point</a> </td> <td>155 °C (311 °F; 428 K) </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Autoignition_temperature" title="Autoignition temperature">Autoignition<br />temperature</a></div> </td> <td>345 °C (653 °F; 618 K) </td></tr> <tr> <td><a href="/wiki/Explosive_limit" class="mw-redirect" title="Explosive limit">Explosive limits</a> </td> <td>8%<sup id="cite_ref-sigma_5-5" class="reference"><a href="#cite_note-sigma-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;"><b>Lethal dose</b> or concentration (LD, LC): </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">LD<sub>50</sub> (<a href="/wiki/Lethal_dose#LD50" title="Lethal dose">median dose</a>)</div> </td> <td>3000<span class="nowrap"> </span>mg/kg (rats, oral) </td></tr> <tr> <td><a href="/wiki/Safety_data_sheet" title="Safety data sheet">Safety data sheet</a> (SDS) </td> <td><a rel="nofollow" class="external text" href="http://www.hmdb.ca/system/metabolites/msds/000/000/065/original/HMDB00094.pdf?1358893891">HMDB</a> (PDF) </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"></div> <div style="margin-top: 0.3em; text-align: center;"><a href="/wiki/Wikipedia:Chemical_infobox#References" title="Wikipedia:Chemical infobox">Infobox references</a></div> </td></tr> </tbody></table><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound</div> <p><b>Citric acid</b> is an <a href="/wiki/Organic_compound" title="Organic compound">organic compound</a> with the <a href="/wiki/Skeletal_formula" title="Skeletal formula">skeletal formula</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap"><a href="/wiki/Hydrogen" title="Hydrogen">H</a><a href="/wiki/Oxygen" title="Oxygen">O</a><a href="/wiki/Carbon" title="Carbon">C</a>(CO<sub class="template-chem2-sub">2</sub>H)(CH<sub class="template-chem2-sub">2</sub>CO<sub class="template-chem2-sub">2</sub>H)<sub class="template-chem2-sub">2</sub></span>.<sup id="cite_ref-:1_10-0" class="reference"><a href="#cite_note-:1-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> It is a <a href="/wiki/Transparency_and_translucency" title="Transparency and translucency">colorless</a> <a href="/wiki/Weak_acid" class="mw-redirect" title="Weak acid">weak</a> <a href="/wiki/Organic_acid" title="Organic acid">organic acid</a>.<sup id="cite_ref-:1_10-1" class="reference"><a href="#cite_note-:1-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> It occurs naturally in <a href="/wiki/Citrus" title="Citrus">citrus fruits</a>. In <a href="/wiki/Biochemistry" title="Biochemistry">biochemistry</a>, it is an intermediate in the <a href="/wiki/Citric_acid_cycle" title="Citric acid cycle">citric acid cycle</a>, which occurs in the <a href="/wiki/Metabolism" title="Metabolism">metabolism</a> of all <a href="/wiki/Aerobic_organism" title="Aerobic organism">aerobic organisms</a>.<sup id="cite_ref-:1_10-2" class="reference"><a href="#cite_note-:1-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p><p>More than two million tons of citric acid <a href="/wiki/Commodity_chemicals" title="Commodity chemicals">are manufactured</a> every year. It is used widely as <a href="/wiki/Acidifier" title="Acidifier">acidifier</a>, <a href="/wiki/Flavoring" title="Flavoring">flavoring</a>, <a href="/wiki/Preservative" title="Preservative">preservative</a>, and <a href="/wiki/Chelating_agent" class="mw-redirect" title="Chelating agent">chelating agent</a>.<sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p><p>A <b>citrate</b> is a derivative of citric acid; that is, the <a href="/wiki/Salt_(chemistry)" title="Salt (chemistry)">salts</a>, <a href="/wiki/Ester" title="Ester">esters</a>, and the <a href="/wiki/Polyatomic_ion" title="Polyatomic ion">polyatomic anion</a> found in solutions and salts of citric acid. An example of the former, a salt is <a href="/wiki/Trisodium_citrate" title="Trisodium citrate">trisodium citrate</a>; an ester is <a href="/wiki/Triethyl_citrate" title="Triethyl citrate">triethyl citrate</a>. When citrate <a href="/wiki/Anion" class="mw-redirect" title="Anion">trianion</a> is part of a salt, the formula of the citrate trianion is written as <span class="chemf nowrap">C<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">6</sub></span></span>H<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">5</sub></span></span>O<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">3−</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">7</sub></span></span></span> or <span class="chemf nowrap">C<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">3</sub></span></span>H<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">5</sub></span></span>O(COO)<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">3−</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">3</sub></span></span></span>. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Natural_occurrence_and_industrial_production">Natural occurrence and industrial production</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Citric_acid&action=edit&section=1" title="Edit section: Natural occurrence and industrial production"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:Citrus_fruits.jpg" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e0/Citrus_fruits.jpg/220px-Citrus_fruits.jpg" decoding="async" width="220" height="145" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e0/Citrus_fruits.jpg/330px-Citrus_fruits.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e0/Citrus_fruits.jpg/440px-Citrus_fruits.jpg 2x" data-file-width="2700" data-file-height="1779" /></a><figcaption>Lemons, oranges, limes, and other citrus fruits contain high concentrations of citric acid.</figcaption></figure> <p>Citric acid occurs in a variety of fruits and vegetables, most notably <a href="/wiki/Citrus" title="Citrus">citrus fruits</a>. <a href="/wiki/Lemon" title="Lemon">Lemons</a> and <a href="/wiki/Lime_(fruit)" title="Lime (fruit)">limes</a> have particularly high concentrations of the acid; it can constitute as much as 8% of the dry weight of these fruits (about 47 g/L in the juices<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>).<sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>a<span class="cite-bracket">]</span></a></sup> The concentrations of citric acid in citrus fruits range from 0.005 <a href="/wiki/Molarity" class="mw-redirect" title="Molarity">mol/L</a> for oranges and grapefruits to 0.30 mol/L in lemons and limes; these values vary within species depending upon the <a href="/wiki/Cultivar" title="Cultivar">cultivar</a> and the circumstances under which the fruit was grown. </p><p>Citric acid was first isolated in 1784 by the chemist <a href="/wiki/Carl_Wilhelm_Scheele" title="Carl Wilhelm Scheele">Carl Wilhelm Scheele</a>, who crystallized it from lemon juice.<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-book1_15-0" class="reference"><a href="#cite_note-book1-15"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p><p>Industrial-scale citric acid production first began in 1890 based on the Italian <a href="/wiki/Citrus_fruit" class="mw-redirect" title="Citrus fruit">citrus fruit</a> industry, where the juice was treated with hydrated lime (<a href="/wiki/Calcium_hydroxide" title="Calcium hydroxide">calcium hydroxide</a>) to precipitate <a href="/wiki/Calcium_citrate" title="Calcium citrate">calcium citrate</a>, which was isolated and converted back to the acid using diluted <a href="/wiki/Sulfuric_acid" title="Sulfuric acid">sulfuric acid</a>.<sup id="cite_ref-ullmann_16-0" class="reference"><a href="#cite_note-ullmann-16"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> In 1893, <a href="/wiki/Carl_Wehmer_(chemist)" class="mw-redirect" title="Carl Wehmer (chemist)">C. Wehmer</a> discovered <i><a href="/wiki/Penicillium" title="Penicillium">Penicillium</a></i> <a href="/wiki/Mold_(fungus)" class="mw-redirect" title="Mold (fungus)">mold</a> could produce citric acid from sugar.<sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> However, microbial production of citric acid did not become industrially important until World War I disrupted Italian citrus exports. </p><p>In 1917, American food chemist James Currie discovered that certain strains of the mold <i><a href="/wiki/Aspergillus_niger" title="Aspergillus niger">Aspergillus niger</a></i> could be efficient citric acid producers,<sup id="cite_ref-18" class="reference"><a href="#cite_note-18"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> and the pharmaceutical company <a href="/wiki/Pfizer" title="Pfizer">Pfizer</a> began industrial-level production using this technique two years later, followed by <a href="/wiki/Citrique_Belge" title="Citrique Belge">Citrique Belge</a> in 1929. In this production technique, which is still the major industrial route to citric acid used today, cultures of <i>Aspergillus niger</i> are fed on a <a href="/wiki/Sucrose" title="Sucrose">sucrose</a> or <a href="/wiki/Glucose" title="Glucose">glucose</a>-containing medium to produce citric acid. The source of sugar is <a href="/wiki/Corn_steep_liquor" title="Corn steep liquor">corn steep liquor</a>, <a href="/wiki/Molasses" title="Molasses">molasses</a>, hydrolyzed <a href="/wiki/Corn_starch" title="Corn starch">corn starch</a>, or other inexpensive, <a href="/wiki/Carbohydrate" title="Carbohydrate">carbohydrate</a> solution.<sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> After the mold is filtered out of the resulting <a href="/wiki/Suspension_(chemistry)" title="Suspension (chemistry)">suspension</a>, citric acid is isolated by <a href="/wiki/Precipitation_(chemistry)" title="Precipitation (chemistry)">precipitating</a> it with calcium hydroxide to yield calcium citrate salt, from which citric acid is regenerated by treatment with sulfuric acid, as in the direct extraction from citrus fruit juice. </p><p>In 1977, a patent was granted to <a href="/wiki/Lever_Brothers" title="Lever Brothers">Lever Brothers</a> for the chemical synthesis of citric acid starting either from aconitic or isocitrate (also called alloisocitrate) calcium salts under high pressure conditions; this produced citric acid in near quantitative conversion under what appeared to be a reverse, non-enzymatic <a href="/wiki/Krebs_cycle_reaction" class="mw-redirect" title="Krebs cycle reaction">Krebs cycle reaction</a>.<sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> </p><p>Global production was in excess of 2,000,000 tons in 2018.<sup id="cite_ref-21" class="reference"><a href="#cite_note-21"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> More than 50% of this volume was produced in China. More than 50% was used as an <a href="/wiki/Acidity_regulator" title="Acidity regulator">acidity regulator</a> in beverages, some 20% in other food applications, 20% for detergent applications, and 10% for applications other than food, such as cosmetics, pharmaceuticals, and in the chemical industry.<sup id="cite_ref-ullmann_16-1" class="reference"><a href="#cite_note-ullmann-16"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Chemical_characteristics">Chemical characteristics</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Citric_acid&action=edit&section=2" title="Edit section: Chemical characteristics"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:Citric_acid_speciation.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/00/Citric_acid_speciation.svg/220px-Citric_acid_speciation.svg.png" decoding="async" width="220" height="131" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/00/Citric_acid_speciation.svg/330px-Citric_acid_speciation.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/00/Citric_acid_speciation.svg/440px-Citric_acid_speciation.svg.png 2x" data-file-width="723" data-file-height="432" /></a><figcaption><a href="/wiki/Ion_speciation" title="Ion speciation">Speciation</a> diagram for a 10-millimolar solution of citric acid</figcaption></figure> <p>Citric acid can be obtained as an <a href="/wiki/Anhydrous" title="Anhydrous">anhydrous</a> (water-free) form or as a <a href="/wiki/Hydrate" title="Hydrate">monohydrate</a>. The anhydrous form crystallizes from hot water, while the monohydrate forms when citric acid is crystallized from cold water. The monohydrate can be converted to the anhydrous form at about 78 °C. Citric acid also dissolves in absolute (anhydrous) <a href="/wiki/Ethanol" title="Ethanol">ethanol</a> (76 parts of citric acid per 100 parts of ethanol) at 15 °C. It <a href="/wiki/Decarboxylation" title="Decarboxylation">decomposes</a> with loss of carbon dioxide above about 175 °C. </p><p>Citric acid is a tribasic <a href="/wiki/Acid" title="Acid">acid</a>, with <a href="/wiki/Acid_dissociation_constant" title="Acid dissociation constant">pK<sub>a</sub></a> values, extrapolated to zero ionic strength, of 3.128, 4.761, and 6.396 at 25 °C.<sup id="cite_ref-22" class="reference"><a href="#cite_note-22"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> The pK<sub>a</sub> of the hydroxyl group has been found, by means of <a href="/wiki/Carbon-13_NMR_spectroscopy" class="mw-redirect" title="Carbon-13 NMR spectroscopy"><sup>13</sup>C NMR spectroscopy</a>, to be 14.4.<sup id="cite_ref-23" class="reference"><a href="#cite_note-23"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> The speciation diagram shows that solutions of citric acid are <a href="/wiki/Buffer_solution" title="Buffer solution">buffer solutions</a> between about pH 2 and pH 8. In biological systems around pH 7, the two species present are the citrate ion and mono-hydrogen citrate ion. The SSC 20X hybridization buffer is an example in common use.<sup id="cite_ref-24" class="reference"><a href="#cite_note-24"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-25" class="reference"><a href="#cite_note-25"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> Tables compiled for biochemical studies are available.<sup id="cite_ref-26" class="reference"><a href="#cite_note-26"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> </p><p>Conversely, the pH of a 1 mM solution of citric acid will be about 3.2. The pH of fruit juices from <a href="/wiki/Citrus_fruit" class="mw-redirect" title="Citrus fruit">citrus fruits</a> like oranges and lemons depends on the citric acid concentration, with a higher concentration of citric acid resulting in a lower pH. </p><p><a href="/wiki/Acid_salt" title="Acid salt">Acid salts</a> of citric acid can be prepared by careful adjustment of the pH before crystallizing the compound. See, for example, <a href="/wiki/Sodium_citrate" title="Sodium citrate">sodium citrate</a>. </p><p>The citrate ion forms complexes with metallic cations. The <a href="/wiki/Stability_constants_of_complexes" title="Stability constants of complexes">stability constants</a> for the formation of these complexes are quite large because of the <a href="/wiki/Chelate_effect" class="mw-redirect" title="Chelate effect">chelate effect</a>. Consequently, it forms complexes even with alkali metal cations. However, when a chelate complex is formed using all three carboxylate groups, the chelate rings have 7 and 8 members, which are generally less stable thermodynamically than smaller chelate rings. In consequence, the hydroxyl group can be deprotonated, forming part of a more stable 5-membered ring, as in <a href="/wiki/Ammonium_ferric_citrate" title="Ammonium ferric citrate">ammonium ferric citrate</a>, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">[NH<span class="template-chem2-su"><span>+</span><span>4</span></span>]<sub class="template-chem2-sub">5</sub>Fe<sup>3+</sup>(C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">4</sub>O<span class="template-chem2-su"><span>4−</span><span>7</span></span>)<sub class="template-chem2-sub">2</sub>·2H<sub>2</sub>O</span>.<sup id="cite_ref-27" class="reference"><a href="#cite_note-27"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> </p><p>Citric acid can be <a href="/wiki/Ester" title="Ester">esterified</a> at one or more of its three <a href="/wiki/Carboxylic_acid" title="Carboxylic acid">carboxylic acid</a> groups to form any of a variety of mono-, di-, tri-, and mixed esters.<sup id="cite_ref-28" class="reference"><a href="#cite_note-28"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Biochemistry">Biochemistry</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Citric_acid&action=edit&section=3" title="Edit section: Biochemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Citric_acid_cycle">Citric acid cycle</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Citric_acid&action=edit&section=4" title="Edit section: Citric acid cycle"><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/Citric_acid_cycle" title="Citric acid cycle">Citric acid cycle</a></div> <p>Citrate is an intermediate in the <a href="/wiki/Citric_acid_cycle" title="Citric acid cycle">citric acid cycle</a>, also known as the TCA (<b>T</b>ri<b>C</b>arboxylic <b>A</b>cid) cycle or the Krebs cycle, a central metabolic pathway for animals, plants, and bacteria. In the Krebs cycle, <a href="/wiki/Citrate_synthase" title="Citrate synthase">citrate synthase</a> catalyzes the condensation of <a href="/wiki/Oxaloacetate" class="mw-redirect" title="Oxaloacetate">oxaloacetate</a> with acetyl CoA to form citrate. Citrate then acts as the substrate for <a href="/wiki/Aconitase" title="Aconitase">aconitase</a> and is converted into <a href="/wiki/Aconitic_acid" title="Aconitic acid">aconitic acid</a>. The cycle ends with regeneration of oxaloacetate. This series of chemical reactions is the source of two-thirds of the food-derived energy in higher organisms. The chemical energy released is available under the form of <a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate">Adenosine triphosphate</a> (ATP). <a href="/wiki/Hans_Adolf_Krebs" class="mw-redirect" title="Hans Adolf Krebs">Hans Adolf Krebs</a> received the 1953 <a href="/wiki/Nobel_Prize_in_Physiology_or_Medicine" title="Nobel Prize in Physiology or Medicine">Nobel Prize in Physiology or Medicine</a> for the discovery. </p> <div class="mw-heading mw-heading3"><h3 id="Other_biological_roles">Other biological roles</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Citric_acid&action=edit&section=5" title="Edit section: Other biological roles"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Citrate can be transported out of the <a href="/wiki/Mitochondria" class="mw-redirect" title="Mitochondria">mitochondria</a> and into the cytoplasm, then broken down into <a href="/wiki/Acetyl-CoA" title="Acetyl-CoA">acetyl-CoA</a> for <a href="/wiki/Fatty_acid_synthesis" title="Fatty acid synthesis">fatty acid synthesis</a>, and into oxaloacetate. Citrate is a positive modulator of this conversion, and <a href="/wiki/Allosterically" class="mw-redirect" title="Allosterically">allosterically</a> regulates the enzyme <a href="/wiki/Acetyl-CoA_carboxylase" title="Acetyl-CoA carboxylase">acetyl-CoA carboxylase</a>, which is the regulating enzyme in the conversion of acetyl-CoA into <a href="/wiki/Malonyl-CoA" title="Malonyl-CoA">malonyl-CoA</a> (the commitment step in fatty acid synthesis). In short, citrate is transported into the cytoplasm, converted into acetyl-CoA, which is then converted into malonyl-CoA by acetyl-CoA carboxylase, which is allosterically modulated by citrate. </p><p>High concentrations of cytosolic citrate can inhibit <a href="/wiki/Phosphofructokinase" title="Phosphofructokinase">phosphofructokinase</a>, the catalyst of a rate-limiting step of <a href="/wiki/Glycolysis" title="Glycolysis">glycolysis</a>. This effect is advantageous: high concentrations of citrate indicate that there is a large supply of biosynthetic precursor molecules, so there is no need for phosphofructokinase to continue to send molecules of its substrate, <a href="/wiki/Fructose_6-phosphate" title="Fructose 6-phosphate">fructose 6-phosphate</a>, into glycolysis. Citrate acts by augmenting the inhibitory effect of high concentrations of <a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate">ATP</a>, another sign that there is no need to carry out glycolysis.<sup id="cite_ref-Tightly_Controlled_29-0" class="reference"><a href="#cite_note-Tightly_Controlled-29"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> </p><p>Citrate is a vital component of bone, helping to regulate the size of <a href="/wiki/Apatite" title="Apatite">apatite</a> crystals.<sup id="cite_ref-30" class="reference"><a href="#cite_note-30"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Applications">Applications</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Citric_acid&action=edit&section=6" title="Edit section: Applications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Food_and_drink">Food and drink</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Citric_acid&action=edit&section=7" title="Edit section: Food and drink"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1235681985">.mw-parser-output .side-box{margin:4px 0;box-sizing:border-box;border:1px solid #aaa;font-size:88%;line-height:1.25em;background-color:var(--background-color-interactive-subtle,#f8f9fa);display:flow-root}.mw-parser-output .side-box-abovebelow,.mw-parser-output .side-box-text{padding:0.25em 0.9em}.mw-parser-output .side-box-image{padding:2px 0 2px 0.9em;text-align:center}.mw-parser-output .side-box-imageright{padding:2px 0.9em 2px 0;text-align:center}@media(min-width:500px){.mw-parser-output .side-box-flex{display:flex;align-items:center}.mw-parser-output .side-box-text{flex:1;min-width:0}}@media(min-width:720px){.mw-parser-output .side-box{width:238px}.mw-parser-output .side-box-right{clear:right;float:right;margin-left:1em}.mw-parser-output .side-box-left{margin-right:1em}}</style><style data-mw-deduplicate="TemplateStyles:r1237033735">@media print{body.ns-0 .mw-parser-output .sistersitebox{display:none!important}}@media screen{html.skin-theme-clientpref-night .mw-parser-output .sistersitebox img[src*="Wiktionary-logo-en-v2.svg"]{background-color:white}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .sistersitebox img[src*="Wiktionary-logo-en-v2.svg"]{background-color:white}}</style><div class="side-box side-box-right plainlinks sistersitebox"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"> <div class="side-box-flex"> <div class="side-box-image"><span class="noviewer" typeof="mw:File"><span><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/d/df/Wikibooks-logo-en-noslogan.svg/40px-Wikibooks-logo-en-noslogan.svg.png" decoding="async" width="40" height="40" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/df/Wikibooks-logo-en-noslogan.svg/60px-Wikibooks-logo-en-noslogan.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/df/Wikibooks-logo-en-noslogan.svg/80px-Wikibooks-logo-en-noslogan.svg.png 2x" data-file-width="400" data-file-height="400" /></span></span></div> <div class="side-box-text plainlist">Wikibooks <a href="https://en.wikibooks.org/wiki/Cookbook" class="extiw" title="wikibooks:Cookbook">Cookbook</a> has a recipe/module on <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist" style="margin-left: 1.6em;"> <ul><li><i><b><a href="https://en.wikibooks.org/wiki/Cookbook:Citric_Acid" class="extiw" title="wikibooks:Cookbook:Citric Acid"> Citric Acid</a></b></i></li></ul> </div></div></div> </div><figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Lemon_pepper_preparation.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/7b/Lemon_pepper_preparation.jpg/220px-Lemon_pepper_preparation.jpg" decoding="async" width="220" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/7b/Lemon_pepper_preparation.jpg/330px-Lemon_pepper_preparation.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/7b/Lemon_pepper_preparation.jpg/440px-Lemon_pepper_preparation.jpg 2x" data-file-width="800" data-file-height="438" /></a><figcaption>Powdered citric acid being used to prepare <a href="/wiki/Lemon_pepper" title="Lemon pepper">lemon pepper</a> seasoning</figcaption></figure> <p>Because it is one of the stronger edible acids, the dominant use of citric acid is as a flavoring and preservative in food and beverages, especially soft drinks and candies.<sup id="cite_ref-ullmann_16-2" class="reference"><a href="#cite_note-ullmann-16"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> Within the <a href="/wiki/European_Union" title="European Union">European Union</a> it is denoted by <a href="/wiki/E_number" title="E number">E number</a> <b>E330</b>. Citrate salts of various metals are used to deliver those minerals in a biologically available form in many <a href="/wiki/Dietary_supplement" title="Dietary supplement">dietary supplements</a>. Citric acid has 247 kcal per 100 g.<sup id="cite_ref-FAOSouthgate_31-0" class="reference"><a href="#cite_note-FAOSouthgate-31"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> In the United States the purity requirements for citric acid as a food additive are defined by the <a href="/wiki/Food_Chemicals_Codex" title="Food Chemicals Codex">Food Chemicals Codex</a>, which is published by the <a href="/wiki/United_States_Pharmacopoeia" class="mw-redirect" title="United States Pharmacopoeia">United States Pharmacopoeia</a> (USP). </p><p>Citric acid can be added to ice cream as an emulsifying agent to keep fats from separating, to caramel to prevent sucrose crystallization, or in recipes in place of fresh lemon juice. Citric acid is used with <a href="/wiki/Sodium_bicarbonate" title="Sodium bicarbonate">sodium bicarbonate</a> in a wide range of <a href="/wiki/Effervescence" title="Effervescence">effervescent</a> formulae, both for ingestion (e.g., powders and tablets) and for personal care (<i>e.g.</i>, <a href="/wiki/Bath_salts" title="Bath salts">bath salts</a>, <a href="/wiki/Bath_bomb" title="Bath bomb">bath bombs</a>, and cleaning of <a href="/wiki/Petroleum" title="Petroleum">grease</a>). Citric acid sold in a dry powdered form is commonly sold in markets and groceries as "sour salt", due to its physical resemblance to table salt. It has use in culinary applications, as an alternative to vinegar or lemon juice, where a pure acid is needed. Citric acid can be used in <a href="/wiki/Food_coloring" title="Food coloring">food coloring</a> to balance the pH level of a normally basic dye.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (October 2019)">citation needed</span></a></i>]</sup> </p> <div class="mw-heading mw-heading3"><h3 id="Cleaning_and_chelating_agent">Cleaning and chelating agent</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Citric_acid&action=edit&section=8" title="Edit section: Cleaning and chelating agent"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:Fe2CITdianion.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/Fe2CITdianion.svg/144px-Fe2CITdianion.svg.png" decoding="async" width="144" height="162" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/Fe2CITdianion.svg/216px-Fe2CITdianion.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/Fe2CITdianion.svg/288px-Fe2CITdianion.svg.png 2x" data-file-width="129" data-file-height="145" /></a><figcaption>Structure of an iron(III) citrate complex<sup id="cite_ref-xiang_32-0" class="reference"><a href="#cite_note-xiang-32"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-shweky_33-0" class="reference"><a href="#cite_note-shweky-33"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup></figcaption></figure> <p>Citric acid is an excellent <a href="/wiki/Chelation" title="Chelation">chelating agent</a>, binding metals by making them soluble. It is used to remove and discourage the buildup of <a href="/wiki/Limescale" title="Limescale">limescale</a> from boilers and evaporators.<sup id="cite_ref-ullmann_16-3" class="reference"><a href="#cite_note-ullmann-16"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> It can be used to treat water, which makes it useful in improving the effectiveness of soaps and laundry detergents. By chelating the metals in <a href="/wiki/Hard_water" title="Hard water">hard water</a>, it lets these cleaners produce foam and work better without need for water softening. Citric acid is the active ingredient in some bathroom and kitchen cleaning solutions. A solution with a six percent concentration of citric acid will remove hard water stains from glass without scrubbing. Citric acid can be used in shampoo to wash out wax and coloring from the hair. Illustrative of its chelating abilities, citric acid was the first successful <a href="/wiki/Eluant" class="mw-redirect" title="Eluant">eluant</a> used for total ion-exchange separation of the <a href="/wiki/Lanthanide" title="Lanthanide">lanthanides</a>, during the <a href="/wiki/Manhattan_Project" title="Manhattan Project">Manhattan Project</a> in the 1940s.<sup id="cite_ref-34" class="reference"><a href="#cite_note-34"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> In the 1950s, it was replaced by the far more efficient<sup id="cite_ref-35" class="reference"><a href="#cite_note-35"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Ethylenediaminetetraacetic_acid" title="Ethylenediaminetetraacetic acid">EDTA</a>. </p><p>In industry, it is used to dissolve rust from steel, and to <a href="/wiki/Passivation_(chemistry)" title="Passivation (chemistry)">passivate</a> <a href="/wiki/Stainless_steel" title="Stainless steel">stainless steels</a>.<sup id="cite_ref-36" class="reference"><a href="#cite_note-36"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Cosmetics,_pharmaceuticals,_dietary_supplements,_and_foods"><span id="Cosmetics.2C_pharmaceuticals.2C_dietary_supplements.2C_and_foods"></span>Cosmetics, pharmaceuticals, dietary supplements, and foods</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Citric_acid&action=edit&section=9" title="Edit section: Cosmetics, pharmaceuticals, dietary supplements, and foods"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Citric acid is used as an <a href="/wiki/Acidulant" title="Acidulant">acidulant</a> in creams, gels, and liquids. Used in foods and dietary supplements, it may be classified as a processing aid if it was added for a technical or functional effect (e.g. acidulent, chelator, viscosifier, etc.). If it is still present in insignificant amounts, and the technical or functional effect is no longer present, it may be exempt from labeling <21 CFR §101.100(c)>. </p><p>Citric acid is an <a href="/wiki/Alpha_hydroxy_acid" class="mw-redirect" title="Alpha hydroxy acid">alpha hydroxy acid</a> and is an active ingredient in chemical skin peels.<sup id="cite_ref-37" class="reference"><a href="#cite_note-37"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup> </p><p>Citric acid is commonly used as a buffer to increase the solubility of brown <a href="/wiki/Heroin" title="Heroin">heroin</a>.<sup id="cite_ref-38" class="reference"><a href="#cite_note-38"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup> </p><p>Citric acid is used as one of the active ingredients in the production of facial tissues with antiviral properties.<sup id="cite_ref-39" class="reference"><a href="#cite_note-39"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Other_uses">Other uses</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Citric_acid&action=edit&section=10" title="Edit section: Other uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The <a href="/wiki/Buffering_agent" class="mw-redirect" title="Buffering agent">buffering</a> properties of citrates are used to control <a href="/wiki/PH" title="PH">pH</a> in household cleaners and <a href="/wiki/Pharmaceutical" class="mw-redirect" title="Pharmaceutical">pharmaceuticals</a>. </p><p>Citric acid is used as an odorless alternative to <a href="/wiki/White_vinegar" class="mw-redirect" title="White vinegar">white vinegar</a> for fabric dyeing with <a href="/wiki/Acid_dye" title="Acid dye">acid dyes</a>. </p><p>Sodium citrate is a component of <a href="/wiki/Benedict%27s_reagent" title="Benedict's reagent">Benedict's reagent</a>, used for both qualitative and quantitative identification of reducing sugars.<sup id="cite_ref-40" class="reference"><a href="#cite_note-40"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup> </p><p>Citric acid can be used as an alternative to nitric acid in <a href="/wiki/Passivation_(chemistry)" title="Passivation (chemistry)">passivation</a> of <a href="/wiki/Stainless_steel" title="Stainless steel">stainless steel</a>.<sup id="cite_ref-41" class="reference"><a href="#cite_note-41"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup> </p><p>Citric acid can be used as a lower-odor <a href="/wiki/Stop_bath" title="Stop bath">stop bath</a> as part of the process for developing <a href="/wiki/Photographic_film" title="Photographic film">photographic film</a>. <a href="/wiki/Photographic_developer" title="Photographic developer">Photographic developers</a> are alkaline, so a mild acid is used to neutralize and stop their action quickly, but commonly used <a href="/wiki/Acetic_acid" title="Acetic acid">acetic acid</a> leaves a strong vinegar odor in the darkroom.<sup id="cite_ref-42" class="reference"><a href="#cite_note-42"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> </p><p><a href="/wiki/Citric_acid/potassium-sodium_citrate" title="Citric acid/potassium-sodium citrate">Citric acid/potassium-sodium citrate</a> can be used as a blood acid regulator. The citric acid is included to improve palatability<sup id="cite_ref-43" class="reference"><a href="#cite_note-43"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup> </p><p>Citric acid is an excellent <a href="/wiki/Soldering" title="Soldering">soldering</a> <a href="/wiki/Flux_(metallurgy)" title="Flux (metallurgy)">flux</a>,<sup id="cite_ref-44" class="reference"><a href="#cite_note-44"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup> either dry or as a concentrated solution in water. It should be removed after soldering, especially with fine wires, as it is mildly corrosive. It dissolves and rinses quickly in hot water. </p><p><a href="/wiki/Alkali_citrate" title="Alkali citrate">Alkali citrate</a> can be used as an inhibitor of kidney stones by increasing urine citrate levels, useful for prevention of calcium stones, and increasing urine pH, useful for preventing uric acid and cystine stones.<sup id="cite_ref-45" class="reference"><a href="#cite_note-45"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Synthesis_of_other_organic_compounds">Synthesis of other organic compounds</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Citric_acid&action=edit&section=11" title="Edit section: Synthesis of other organic compounds"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Citric acid is a versatile precursor to many other organic compounds. Dehydration routes give <a href="/wiki/Itaconic_acid" title="Itaconic acid">itaconic acid</a> and its anhydride.<sup id="cite_ref-46" class="reference"><a href="#cite_note-46"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Citraconic_acid" title="Citraconic acid">Citraconic acid</a> can be produced via thermal isomerization of itaconic acid anhydride.<sup id="cite_ref-47" class="reference"><a href="#cite_note-47"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup> The required itaconic acid anhydride is obtained by dry distillation of citric acid. <a href="/wiki/Aconitic_acid" title="Aconitic acid">Aconitic acid</a> can be synthesized by dehydration of citric acid using <a href="/wiki/Sulfuric_acid" title="Sulfuric acid">sulfuric acid</a>:<sup id="cite_ref-48" class="reference"><a href="#cite_note-48"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup> </p> <dl><dd>(HO<sub>2</sub>CCH<sub>2</sub>)<sub>2</sub>C(OH)CO<sub>2</sub>H → HO<sub>2</sub>CCH=C(CO<sub>2</sub>H)CH<sub>2</sub>CO<sub>2</sub>H + H<sub>2</sub>O</dd></dl> <p><a href="/wiki/Acetonedicarboxylic_acid" title="Acetonedicarboxylic acid">Acetonedicarboxylic acid</a> can also be prepared by <a href="/wiki/Decarboxylation" title="Decarboxylation">decarboxylation</a> of citric acid in fuming sulfuric acid.<sup id="cite_ref-49" class="reference"><a href="#cite_note-49"><span class="cite-bracket">[</span>48<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Safety">Safety</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Citric_acid&action=edit&section=12" title="Edit section: Safety"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Although a weak acid, exposure to pure citric acid can cause adverse effects. Inhalation may cause cough, shortness of breath, or sore throat. Over-ingestion may cause abdominal pain and sore throat. Exposure of concentrated solutions to skin and eyes can cause redness and pain.<sup id="cite_ref-ICSC_50-0" class="reference"><a href="#cite_note-ICSC-50"><span class="cite-bracket">[</span>49<span class="cite-bracket">]</span></a></sup> Long-term or repeated consumption may cause erosion of <a href="/wiki/Tooth_enamel" title="Tooth enamel">tooth enamel</a>.<sup id="cite_ref-ICSC_50-1" class="reference"><a href="#cite_note-ICSC-50"><span class="cite-bracket">[</span>49<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-51" class="reference"><a href="#cite_note-51"><span class="cite-bracket">[</span>50<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-52" class="reference"><a href="#cite_note-52"><span class="cite-bracket">[</span>51<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Compendial_status">Compendial status</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Citric_acid&action=edit&section=13" title="Edit section: Compendial status"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/British_Pharmacopoeia" title="British Pharmacopoeia">British Pharmacopoeia</a><sup id="cite_ref-ib29_53-0" class="reference"><a href="#cite_note-ib29-53"><span class="cite-bracket">[</span>52<span class="cite-bracket">]</span></a></sup></li> <li><a href="/wiki/Japanese_Pharmacopoeia" title="Japanese Pharmacopoeia">Japanese Pharmacopoeia</a><sup id="cite_ref-jp15_54-0" class="reference"><a href="#cite_note-jp15-54"><span class="cite-bracket">[</span>53<span class="cite-bracket">]</span></a></sup></li></ul> <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=Citric_acid&action=edit&section=14" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li>Closely related acids: <a href="/wiki/Isocitric_acid" title="Isocitric acid">isocitric acid</a>, <a href="/wiki/Aconitic_acid" title="Aconitic acid">aconitic acid</a>, and <a href="/wiki/Propane-1,2,3-tricarboxylic_acid" title="Propane-1,2,3-tricarboxylic acid">propane-1,2,3-tricarboxylic acid</a> (tricarballylic acid, carballylic acid)</li> <li><a href="/wiki/Acids_in_wine" title="Acids in wine">Acids in wine</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="Explanatory_notes">Explanatory notes</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Citric_acid&action=edit&section=15" title="Edit section: Explanatory notes"><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 reflist-lower-alpha" style="column-width: 30em;"> <ol class="references"> <li id="cite_note-13"><span class="mw-cite-backlink"><b><a href="#cite_ref-13">^</a></b></span> <span class="reference-text">This still does not make the lemon particularly strongly acidic. This is because, as a weak acid, most of the acid molecules are not dissociated so not contributing to acidity inside the lemon or its juice.</span> </li> </ol></div> <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=Citric_acid&action=edit&section=16" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239543626"><div class="reflist reflist-columns references-column-width" style="column-width: 30em;"> <ol class="references"> <li id="cite_note-IUPAC2014-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-IUPAC2014_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-IUPAC2014_1-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFInternational_Union_of_Pure_and_Applied_Chemistry2014" class="citation book cs1"><a href="/wiki/International_Union_of_Pure_and_Applied_Chemistry" title="International Union of Pure and Applied Chemistry">International Union of Pure and Applied Chemistry</a> (2014). <i>Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013</i>. <a href="/wiki/Royal_Society_of_Chemistry" title="Royal Society of Chemistry">The Royal Society of Chemistry</a>. p. 747. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1039%2F9781849733069">10.1039/9781849733069</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-85404-182-4" title="Special:BookSources/978-0-85404-182-4"><bdi>978-0-85404-182-4</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Nomenclature+of+Organic+Chemistry%3A+IUPAC+Recommendations+and+Preferred+Names+2013&rft.pages=747&rft.pub=The+Royal+Society+of+Chemistry&rft.date=2014&rft_id=info%3Adoi%2F10.1039%2F9781849733069&rft.isbn=978-0-85404-182-4&rft.au=International+Union+of+Pure+and+Applied+Chemistry&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACitric+acid" class="Z3988"></span></span> </li> <li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/22230">CID 22230</a> from <a href="/wiki/PubChem" title="PubChem">PubChem</a></span> </li> <li id="cite_note-chemister-3"><span class="mw-cite-backlink">^ <a href="#cite_ref-chemister_3-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-chemister_3-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-chemister_3-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-chemister_3-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-chemister_3-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-chemister_3-5"><sup><i><b>f</b></i></sup></a> <a href="#cite_ref-chemister_3-6"><sup><i><b>g</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20141129151027/http://chemister.ru/Database/properties-en.php?dbid=1&id=1624">"citric acid"</a>. <i>chemister.ru</i>. Archived from <a rel="nofollow" class="external text" href="http://chemister.ru/Database/properties-en.php?dbid=1&id=1624">the original</a> on November 29, 2014<span class="reference-accessdate">. Retrieved <span class="nowrap">June 1,</span> 2014</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=chemister.ru&rft.atitle=citric+acid&rft_id=http%3A%2F%2Fchemister.ru%2FDatabase%2Fproperties-en.php%3Fdbid%3D1%26id%3D1624&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACitric+acid" class="Z3988"></span></span> </li> <li id="cite_note-pubchem-4"><span class="mw-cite-backlink">^ <a href="#cite_ref-pubchem_4-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-pubchem_4-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-pubchem_4-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-pubchem_4-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-pubchem_4-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-pubchem_4-5"><sup><i><b>f</b></i></sup></a></span> <span class="reference-text"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/311">CID 311</a> from <a href="/wiki/PubChem" title="PubChem">PubChem</a></span> </li> <li id="cite_note-sigma-5"><span class="mw-cite-backlink">^ <a href="#cite_ref-sigma_5-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-sigma_5-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-sigma_5-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-sigma_5-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-sigma_5-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-sigma_5-5"><sup><i><b>f</b></i></sup></a></span> <span class="reference-text"><a href="/wiki/Fisher_Scientific" title="Fisher Scientific">Fisher Scientific</a>, <a rel="nofollow" class="external text" href="http://www.sigmaaldrich.com/catalog/product/sial/251275">Citric acid</a>. Retrieved on 2014-06-02.</span> </li> <li id="cite_note-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-6">^</a></b></span> <span class="reference-text"> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://www.zirchrom.com/organic.htm">"Data for Biochemical Research"</a>. ZirChrom Separations, Inc<span class="reference-accessdate">. Retrieved <span class="nowrap">January 11,</span> 2012</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Data+for+Biochemical+Research&rft.pub=ZirChrom+Separations%2C+Inc&rft_id=http%3A%2F%2Fwww.zirchrom.com%2Forganic.htm&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACitric+acid" class="Z3988"></span></span> </li> <li id="cite_note-7"><span class="mw-cite-backlink"><b><a href="#cite_ref-7">^</a></b></span> <span class="reference-text"> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://www2.chemistry.msu.edu/faculty/reusch/VirtTxtJml/acidity2.htm">"Ionization Constants of Organic Acids"</a>. Michigan State University<span class="reference-accessdate">. Retrieved <span class="nowrap">January 11,</span> 2012</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Ionization+Constants+of+Organic+Acids&rft.pub=Michigan+State+University&rft_id=http%3A%2F%2Fwww2.chemistry.msu.edu%2Ffaculty%2Freusch%2FVirtTxtJml%2Facidity2.htm&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACitric+acid" class="Z3988"></span></span> </li> <li id="cite_note-Silva_Kong_Hider_2009_pp._771–778-8"><span class="mw-cite-backlink"><b><a href="#cite_ref-Silva_Kong_Hider_2009_pp._771–778_8-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSilvaKongHider2009" class="citation journal cs1">Silva, Andre M. N.; Kong, Xiaole; Hider, Robert C. (2009). "Determination of the pKa value of the hydroxyl group in the α-hydroxycarboxylates citrate, malate and lactate by 13C NMR: implications for metal coordination in biological systems". <i>BioMetals</i>. <b>22</b> (5): 771–778. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2Fs10534-009-9224-5">10.1007/s10534-009-9224-5</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0966-0844">0966-0844</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/19288211">19288211</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=BioMetals&rft.atitle=Determination+of+the+pKa+value+of+the+hydroxyl+group+in+the+%CE%B1-hydroxycarboxylates+citrate%2C+malate+and+lactate+by+13C+NMR%3A+implications+for+metal+coordination+in+biological+systems&rft.volume=22&rft.issue=5&rft.pages=771-778&rft.date=2009&rft.issn=0966-0844&rft_id=info%3Apmid%2F19288211&rft_id=info%3Adoi%2F10.1007%2Fs10534-009-9224-5&rft.aulast=Silva&rft.aufirst=Andre+M.+N.&rft.au=Kong%2C+Xiaole&rft.au=Hider%2C+Robert+C.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACitric+acid" class="Z3988"></span></span> </li> <li id="cite_note-nist-9"><span class="mw-cite-backlink">^ <a href="#cite_ref-nist_9-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-nist_9-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-nist_9-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><a rel="nofollow" class="external text" href="http://webbook.nist.gov/cgi/cbook.cgi?ID=C77929&Mask=FFFF&Units=SI">Citric acid</a> in Linstrom, Peter J.; Mallard, William G. (eds.); <i><a rel="nofollow" class="external text" href="http://webbook.nist.gov">NIST Chemistry WebBook</a>, NIST Standard Reference Database Number 69</i>, National Institute of Standards and Technology, Gaithersburg (MD) (retrieved 2014-06-02)</span> </li> <li id="cite_note-:1-10"><span class="mw-cite-backlink">^ <a href="#cite_ref-:1_10-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-:1_10-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-:1_10-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20220119023922/https://pubchem.ncbi.nlm.nih.gov/compound/citric_acid">"Citric acid | C6H8O7 - PubChem"</a>. Archived from <a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/citric_acid/">the original</a> on January 19, 2022<span class="reference-accessdate">. Retrieved <span class="nowrap">December 19,</span> 2021</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Citric+acid+%26%23124%3B+C6H8O7+-+PubChem&rft_id=https%3A%2F%2Fpubchem.ncbi.nlm.nih.gov%2Fcompound%2Fcitric_acid%2F&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACitric+acid" class="Z3988"></span></span> </li> <li id="cite_note-11"><span class="mw-cite-backlink"><b><a href="#cite_ref-11">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFApleblat2014" class="citation book cs1">Apleblat, Alexander (2014). <i>Citric acid</i>. Springer. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-319-11232-9" title="Special:BookSources/978-3-319-11232-9"><bdi>978-3-319-11232-9</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Citric+acid&rft.pub=Springer&rft.date=2014&rft.isbn=978-3-319-11232-9&rft.aulast=Apleblat&rft.aufirst=Alexander&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACitric+acid" class="Z3988"></span></span> </li> <li id="cite_note-12"><span class="mw-cite-backlink"><b><a href="#cite_ref-12">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPennistonNakadaHolmesAssimos2008" class="citation journal cs1">Penniston KL, Nakada SY, Holmes RP, Assimos DG (2008). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2637791">"Quantitative Assessment of Citric Acid in Lemon Juice, Lime Juice, and Commercially-Available Fruit Juice Products"</a>. <i>Journal of Endourology</i>. <b>22</b> (3): 567–570. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1089%2Fend.2007.0304">10.1089/end.2007.0304</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2637791">2637791</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/18290732">18290732</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Endourology&rft.atitle=Quantitative+Assessment+of+Citric+Acid+in+Lemon+Juice%2C+Lime+Juice%2C+and+Commercially-Available+Fruit+Juice+Products&rft.volume=22&rft.issue=3&rft.pages=567-570&rft.date=2008&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC2637791%23id-name%3DPMC&rft_id=info%3Apmid%2F18290732&rft_id=info%3Adoi%2F10.1089%2Fend.2007.0304&rft.aulast=Penniston&rft.aufirst=KL&rft.au=Nakada%2C+SY&rft.au=Holmes%2C+RP&rft.au=Assimos%2C+DG&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC2637791&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACitric+acid" class="Z3988"></span></span> </li> <li id="cite_note-14"><span class="mw-cite-backlink"><b><a href="#cite_ref-14">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFScheele1784" class="citation journal cs1 cs1-prop-foreign-lang-source">Scheele, Carl Wilhelm (1784). <a rel="nofollow" class="external text" href="https://babel.hathitrust.org/cgi/pt?id=mdp.39015009215438;view=1up;seq=115">"Anmärkning om Citron-saft, samt sätt at crystallisera densamma"</a> [Note about lemon juice, as well as ways to crystallize it]. <i>Kungliga Vetenskaps Academiens Nya Handlingar [New Proceedings of the Royal Academy of Science]</i>. 2nd series (in Swedish). <b>5</b>: 105–109.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Kungliga+Vetenskaps+Academiens+Nya+Handlingar+%5BNew+Proceedings+of+the+Royal+Academy+of+Science%5D&rft.atitle=Anm%C3%A4rkning+om+Citron-saft%2C+samt+s%C3%A4tt+at+crystallisera+densamma&rft.volume=5&rft.pages=105-109&rft.date=1784&rft.aulast=Scheele&rft.aufirst=Carl+Wilhelm&rft_id=https%3A%2F%2Fbabel.hathitrust.org%2Fcgi%2Fpt%3Fid%3Dmdp.39015009215438%3Bview%3D1up%3Bseq%3D115&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACitric+acid" class="Z3988"></span></span> </li> <li id="cite_note-book1-15"><span class="mw-cite-backlink"><b><a href="#cite_ref-book1_15-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGraham1842" class="citation book cs1">Graham, Thomas (1842). <a rel="nofollow" class="external text" href="https://archive.org/details/elementschemist00grahgoog"><i>Elements of chemistry, including the applications of the science in the arts</i></a>. Hippolyte Baillière, foreign bookseller to the Royal College of Surgeons, and to the Royal Society, 219, Regent Street. p. <a rel="nofollow" class="external text" href="https://archive.org/details/elementschemist00grahgoog/page/n973">944</a><span class="reference-accessdate">. Retrieved <span class="nowrap">June 4,</span> 2010</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Elements+of+chemistry%2C+including+the+applications+of+the+science+in+the+arts&rft.pages=944&rft.pub=Hippolyte+Bailli%C3%A8re%2C+foreign+bookseller+to+the+Royal+College+of+Surgeons%2C+and+to+the+Royal+Society%2C+219%2C+Regent+Street.&rft.date=1842&rft.aulast=Graham&rft.aufirst=Thomas&rft_id=https%3A%2F%2Farchive.org%2Fdetails%2Felementschemist00grahgoog&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACitric+acid" class="Z3988"></span></span> </li> <li id="cite_note-ullmann-16"><span class="mw-cite-backlink">^ <a href="#cite_ref-ullmann_16-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-ullmann_16-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-ullmann_16-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-ullmann_16-3"><sup><i><b>d</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFVerhoffBauweleers2014" class="citation encyclopaedia cs1">Verhoff, Frank H.; Bauweleers, Hugo (2014). "Citric Acid". <i><a href="/wiki/Ullmann%27s_Encyclopedia_of_Industrial_Chemistry" title="Ullmann's Encyclopedia of Industrial Chemistry">Ullmann's Encyclopedia of Industrial Chemistry</a></i>. Weinheim: Wiley-VCH. <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.a07_103.pub3">10.1002/14356007.a07_103.pub3</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3527306732" title="Special:BookSources/978-3527306732"><bdi>978-3527306732</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Citric+Acid&rft.btitle=Ullmann%27s+Encyclopedia+of+Industrial+Chemistry&rft.place=Weinheim&rft.pub=Wiley-VCH&rft.date=2014&rft_id=info%3Adoi%2F10.1002%2F14356007.a07_103.pub3&rft.isbn=978-3527306732&rft.aulast=Verhoff&rft.aufirst=Frank+H.&rft.au=Bauweleers%2C+Hugo&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACitric+acid" class="Z3988"></span></span> </li> <li id="cite_note-17"><span class="mw-cite-backlink"><b><a href="#cite_ref-17">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFH._Benninga1990" class="citation book cs1">H. Benninga (June 30, 1990). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=fdBMcYg_xGYC&pg=PA140"><i>A History of Lactic Acid Making: A Chapter in the History of Biotechnology</i></a>. Springer Science & Business Media. pp. 140–5. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-7923-0625-2" title="Special:BookSources/978-0-7923-0625-2"><bdi>978-0-7923-0625-2</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+History+of+Lactic+Acid+Making%3A+A+Chapter+in+the+History+of+Biotechnology&rft.pages=140-5&rft.pub=Springer+Science+%26+Business+Media&rft.date=1990-06-30&rft.isbn=978-0-7923-0625-2&rft.au=H.+Benninga&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DfdBMcYg_xGYC%26pg%3DPA140&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACitric+acid" class="Z3988"></span></span> </li> <li id="cite_note-18"><span class="mw-cite-backlink"><b><a href="#cite_ref-18">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCurrie1917" class="citation book cs1">Currie, James (1917). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=7q8BAAAAYAAJ&pg=PA15"><i>The Journal of Biological Chemistry</i></a>. American Society for Biochemistry and Molecular Biology. pp. 15–27.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+Journal+of+Biological+Chemistry&rft.pages=15-27&rft.pub=American+Society+for+Biochemistry+and+Molecular+Biology&rft.date=1917&rft.aulast=Currie&rft.aufirst=James&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D7q8BAAAAYAAJ%26pg%3DPA15&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACitric+acid" class="Z3988"></span></span> </li> <li id="cite_note-19"><span class="mw-cite-backlink"><b><a href="#cite_ref-19">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLotfyGhanemEl-Helow2007" class="citation journal cs1">Lotfy, Walid A.; Ghanem, Khaled M.; El-Helow, Ehab R. (2007). <a rel="nofollow" class="external text" href="https://scholar.google.com/scholar?hl=en&as_sdt=0%2C5&q=Citric+acid+production+by+a+novel+Aspergillus+niger+isolate%3A+II.+Optimization+of+process+parameters+through+statistical+experimental+designs&btnG=">"Citric acid production by a novel <i>Aspergillus niger</i> isolate: II. Optimization of process parameters through statistical experimental designs"</a> <span class="cs1-format">(PDF)</span>. <i>Bioresource Technology</i>. <b>98</b> (18): 3470–3477. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2007BiTec..98.3470L">2007BiTec..98.3470L</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.biortech.2006.11.032">10.1016/j.biortech.2006.11.032</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/17317159">17317159</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Bioresource+Technology&rft.atitle=Citric+acid+production+by+a+novel+Aspergillus+niger+isolate%3A+II.+Optimization+of+process+parameters+through+statistical+experimental+designs&rft.volume=98&rft.issue=18&rft.pages=3470-3477&rft.date=2007&rft_id=info%3Apmid%2F17317159&rft_id=info%3Adoi%2F10.1016%2Fj.biortech.2006.11.032&rft_id=info%3Abibcode%2F2007BiTec..98.3470L&rft.aulast=Lotfy&rft.aufirst=Walid+A.&rft.au=Ghanem%2C+Khaled+M.&rft.au=El-Helow%2C+Ehab+R.&rft_id=https%3A%2F%2Fscholar.google.com%2Fscholar%3Fhl%3Den%26as_sdt%3D0%252C5%26q%3DCitric%2Bacid%2Bproduction%2Bby%2Ba%2Bnovel%2BAspergillus%2Bniger%2Bisolate%253A%2BII.%2BOptimization%2Bof%2Bprocess%2Bparameters%2Bthrough%2Bstatistical%2Bexperimental%2Bdesigns%26btnG%3D&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACitric+acid" class="Z3988"></span></span> </li> <li id="cite_note-20"><span class="mw-cite-backlink"><b><a href="#cite_ref-20">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLambertiGutierrez1977" class="citation web cs1">Lamberti, Vincent; Gutierrez, Eddie N. (November 1, 1977). <a rel="nofollow" class="external text" href="https://patents.google.com/patent/US4056567A/en">"Chemical processes for preparing citric acid"</a>. <i>Google Patents</i><span class="reference-accessdate">. Retrieved <span class="nowrap">August 4,</span> 2024</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Google+Patents&rft.atitle=Chemical+processes+for+preparing+citric+acid&rft.date=1977-11-01&rft.aulast=Lamberti&rft.aufirst=Vincent&rft.au=Gutierrez%2C+Eddie+N.&rft_id=https%3A%2F%2Fpatents.google.com%2Fpatent%2FUS4056567A%2Fen&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACitric+acid" class="Z3988"></span> (US 4056567)</span> </li> <li id="cite_note-21"><span class="mw-cite-backlink"><b><a href="#cite_ref-21">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.prnewswire.com/news-releases/global-citric-acid-markets-report-2011-2018--2019-2024-300814817.html">"Global Citric Acid Markets Report, 2011-2018 & 2019-2024"</a>. <i>prnewswire.com</i>. March 19, 2019<span class="reference-accessdate">. Retrieved <span class="nowrap">October 28,</span> 2019</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=prnewswire.com&rft.atitle=Global+Citric+Acid+Markets+Report%2C+2011-2018+%26+2019-2024&rft.date=2019-03-19&rft_id=https%3A%2F%2Fwww.prnewswire.com%2Fnews-releases%2Fglobal-citric-acid-markets-report-2011-2018--2019-2024-300814817.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACitric+acid" class="Z3988"></span></span> </li> <li id="cite_note-22"><span class="mw-cite-backlink"><b><a href="#cite_ref-22">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGoldbergKishoreLennen2002" class="citation journal cs1">Goldberg, Robert N.; Kishore, Nand; Lennen, Rebecca M. (2002). <a rel="nofollow" class="external text" href="https://www.nist.gov/system/files/documents/srd/jpcrd615.pdf#page=35&zoom=auto,-76,487">"Thermodynamic Quantities for the Ionization Reactions of Buffers"</a> <span class="cs1-format">(PDF)</span>. <i>J. Phys. Chem. Ref. Data</i>. <b>31</b> (1): 231–370. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2002JPCRD..31..231G">2002JPCRD..31..231G</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1063%2F1.1416902">10.1063/1.1416902</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:94614267">94614267</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J.+Phys.+Chem.+Ref.+Data&rft.atitle=Thermodynamic+Quantities+for+the+Ionization+Reactions+of+Buffers&rft.volume=31&rft.issue=1&rft.pages=231-370&rft.date=2002&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A94614267%23id-name%3DS2CID&rft_id=info%3Adoi%2F10.1063%2F1.1416902&rft_id=info%3Abibcode%2F2002JPCRD..31..231G&rft.aulast=Goldberg&rft.aufirst=Robert+N.&rft.au=Kishore%2C+Nand&rft.au=Lennen%2C+Rebecca+M.&rft_id=https%3A%2F%2Fwww.nist.gov%2Fsystem%2Ffiles%2Fdocuments%2Fsrd%2Fjpcrd615.pdf%23page%3D35%26zoom%3Dauto%2C-76%2C487&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACitric+acid" class="Z3988"></span> (Link added 4 August 2024)</span> </li> <li id="cite_note-23"><span class="mw-cite-backlink"><b><a href="#cite_ref-23">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSilvaKongHider2009" class="citation journal cs1">Silva, Andre M. N.; Kong, Xiaole; Hider, Robert C. (2009). "Determination of the pKa value of the hydroxyl group in the α-hydroxycarboxylates citrate, malate and lactate by <sup>13</sup>C NMR: implications for metal coordination in biological systems". <i>Biometals</i>. <b>22</b> (5): 771–778. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2Fs10534-009-9224-5">10.1007/s10534-009-9224-5</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/19288211">19288211</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:11615864">11615864</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Biometals&rft.atitle=Determination+of+the+pKa+value+of+the+hydroxyl+group+in+the+%CE%B1-hydroxycarboxylates+citrate%2C+malate+and+lactate+by+%3Csup%3E13%3C%2Fsup%3EC+NMR%3A+implications+for+metal+coordination+in+biological+systems&rft.volume=22&rft.issue=5&rft.pages=771-778&rft.date=2009&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A11615864%23id-name%3DS2CID&rft_id=info%3Apmid%2F19288211&rft_id=info%3Adoi%2F10.1007%2Fs10534-009-9224-5&rft.aulast=Silva&rft.aufirst=Andre+M.+N.&rft.au=Kong%2C+Xiaole&rft.au=Hider%2C+Robert+C.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACitric+acid" class="Z3988"></span></span> </li> <li id="cite_note-24"><span class="mw-cite-backlink"><b><a href="#cite_ref-24">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://openwetware.org/wiki/SSC">"SSC - OpenWetWare"</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=SSC+-+OpenWetWare&rft_id=http%3A%2F%2Fopenwetware.org%2Fwiki%2FSSC&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACitric+acid" class="Z3988"></span></span> </li> <li id="cite_note-25"><span class="mw-cite-backlink"><b><a href="#cite_ref-25">^</a></b></span> <span class="reference-text">Maniatis, T.; Fritsch, E. F.; Sambrook, J. 1982. Molecular Cloning: A Laboratory Manual. Cold Spring Harbor Laboratory, Cold Spring Harbor, NY.</span> </li> <li id="cite_note-26"><span class="mw-cite-backlink"><b><a href="#cite_ref-26">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGomori1955" class="citation book cs1">Gomori, G. (1955). <a rel="nofollow" class="external text" href="https://static.igem.org/mediawiki/2008/8/84/Protein_Buffers.pdf">"[16] Preparation of buffers for use in enzyme studies"</a> <span class="cs1-format">(PDF)</span>. <a rel="nofollow" class="external text" href="https://archive.org/details/methodsinenzymol01acad/page/138"><i>Methods in Enzymology Volume 1</i></a>. Vol. 1. pp. 138–146. <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%2F0076-6879%2855%2901020-3">10.1016/0076-6879(55)01020-3</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780121818012" title="Special:BookSources/9780121818012"><bdi>9780121818012</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=%5B16%5D+Preparation+of+buffers+for+use+in+enzyme+studies&rft.btitle=Methods+in+Enzymology+Volume+1&rft.pages=138-146&rft.date=1955&rft_id=info%3Adoi%2F10.1016%2F0076-6879%2855%2901020-3&rft.isbn=9780121818012&rft.aulast=Gomori&rft.aufirst=G.&rft_id=https%3A%2F%2Fstatic.igem.org%2Fmediawiki%2F2008%2F8%2F84%2FProtein_Buffers.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACitric+acid" class="Z3988"></span></span> </li> <li id="cite_note-27"><span class="mw-cite-backlink"><b><a href="#cite_ref-27">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMatzapetakisRaptopoulouTsohosPapaefthymiou1998" class="citation journal cs1">Matzapetakis, M.; Raptopoulou, C. P.; Tsohos, A.; Papaefthymiou, V.; Moon, S. N.; Salifoglou, A. (1998). "Synthesis, Spectroscopic and Structural Characterization of the First Mononuclear, Water Soluble Iron−Citrate Complex, (NH<sub>4</sub>)<sub>5</sub>Fe(C<sub>6</sub>H<sub>4</sub>O<sub>7</sub>)<sub>2</sub>·2H<sub>2</sub>O". <i>J. Am. Chem. Soc</i>. <b>120</b> (50): 13266–13267. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fja9807035">10.1021/ja9807035</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J.+Am.+Chem.+Soc.&rft.atitle=Synthesis%2C+Spectroscopic+and+Structural+Characterization+of+the+First+Mononuclear%2C+Water+Soluble+Iron%E2%88%92Citrate+Complex%2C+%28NH%3Csub%3E4%3C%2Fsub%3E%29%3Csub%3E5%3C%2Fsub%3EFe%28C%3Csub%3E6%3C%2Fsub%3EH%3Csub%3E4%3C%2Fsub%3EO%3Csub%3E7%3C%2Fsub%3E%29%3Csub%3E2%3C%2Fsub%3E%C2%B72H%3Csub%3E2%3C%2Fsub%3EO&rft.volume=120&rft.issue=50&rft.pages=13266-13267&rft.date=1998&rft_id=info%3Adoi%2F10.1021%2Fja9807035&rft.aulast=Matzapetakis&rft.aufirst=M.&rft.au=Raptopoulou%2C+C.+P.&rft.au=Tsohos%2C+A.&rft.au=Papaefthymiou%2C+V.&rft.au=Moon%2C+S.+N.&rft.au=Salifoglou%2C+A.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACitric+acid" class="Z3988"></span></span> </li> <li id="cite_note-28"><span class="mw-cite-backlink"><b><a href="#cite_ref-28">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBergeronXinSmithWollenweber1997" class="citation journal cs1">Bergeron, Raymond J.; Xin, Meiguo; Smith, Richard E.; Wollenweber, Markus; McManis, James S.; Ludin, Christian; Abboud, Khalil A. (1997). "Total synthesis of rhizoferrin, an iron chelator". <i>Tetrahedron</i>. <b>53</b> (2): 427–434. <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%2FS0040-4020%2896%2901061-7">10.1016/S0040-4020(96)01061-7</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Tetrahedron&rft.atitle=Total+synthesis+of+rhizoferrin%2C+an+iron+chelator&rft.volume=53&rft.issue=2&rft.pages=427-434&rft.date=1997&rft_id=info%3Adoi%2F10.1016%2FS0040-4020%2896%2901061-7&rft.aulast=Bergeron&rft.aufirst=Raymond+J.&rft.au=Xin%2C+Meiguo&rft.au=Smith%2C+Richard+E.&rft.au=Wollenweber%2C+Markus&rft.au=McManis%2C+James+S.&rft.au=Ludin%2C+Christian&rft.au=Abboud%2C+Khalil+A.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACitric+acid" class="Z3988"></span></span> </li> <li id="cite_note-Tightly_Controlled-29"><span class="mw-cite-backlink"><b><a href="#cite_ref-Tightly_Controlled_29-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFStryerBergTymoczko2003" class="citation book cs1">Stryer, Lubert; Berg, Jeremy; Tymoczko, John (2003). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/books/NBK22395/">"Section 16.2: The Glycolytic Pathway Is Tightly Controlled"</a>. <i>Biochemistry</i> (5. ed., international ed., 3. printing ed.). New York: Freeman. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0716746843" title="Special:BookSources/978-0716746843"><bdi>978-0716746843</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Section+16.2%3A+The+Glycolytic+Pathway+Is+Tightly+Controlled&rft.btitle=Biochemistry&rft.place=New+York&rft.edition=5.+ed.%2C+international+ed.%2C+3.+printing&rft.pub=Freeman&rft.date=2003&rft.isbn=978-0716746843&rft.aulast=Stryer&rft.aufirst=Lubert&rft.au=Berg%2C+Jeremy&rft.au=Tymoczko%2C+John&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fbooks%2FNBK22395%2F&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACitric+acid" class="Z3988"></span></span> </li> <li id="cite_note-30"><span class="mw-cite-backlink"><b><a href="#cite_ref-30">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHuRawalSchmidt-Rohr2010" class="citation journal cs1">Hu, Y.-Y.; Rawal, A.; Schmidt-Rohr, K. (December 2010). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3012505">"Strongly bound citrate stabilizes the apatite nanocrystals in bone"</a>. <i>Proceedings of the National Academy of Sciences</i>. <b>107</b> (52): 22425–22429. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2010PNAS..10722425H">2010PNAS..10722425H</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1073%2Fpnas.1009219107">10.1073/pnas.1009219107</a></span>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3012505">3012505</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/21127269">21127269</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Proceedings+of+the+National+Academy+of+Sciences&rft.atitle=Strongly+bound+citrate+stabilizes+the+apatite+nanocrystals+in+bone&rft.volume=107&rft.issue=52&rft.pages=22425-22429&rft.date=2010-12&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3012505%23id-name%3DPMC&rft_id=info%3Apmid%2F21127269&rft_id=info%3Adoi%2F10.1073%2Fpnas.1009219107&rft_id=info%3Abibcode%2F2010PNAS..10722425H&rft.aulast=Hu&rft.aufirst=Y.-Y.&rft.au=Rawal%2C+A.&rft.au=Schmidt-Rohr%2C+K.&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3012505&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACitric+acid" class="Z3988"></span></span> </li> <li id="cite_note-FAOSouthgate-31"><span class="mw-cite-backlink"><b><a href="#cite_ref-FAOSouthgate_31-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGreenfieldSouthgate2003" class="citation book cs1">Greenfield, Heather; Southgate, D.A.T. (2003). <i>Food Composition Data: Production, Management and Use</i>. Rome: <a href="/wiki/FAO" class="mw-redirect" title="FAO">FAO</a>. p. 146. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9789251049495" title="Special:BookSources/9789251049495"><bdi>9789251049495</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Food+Composition+Data%3A+Production%2C+Management+and+Use&rft.place=Rome&rft.pages=146&rft.pub=FAO&rft.date=2003&rft.isbn=9789251049495&rft.aulast=Greenfield&rft.aufirst=Heather&rft.au=Southgate%2C+D.A.T.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACitric+acid" class="Z3988"></span></span> </li> <li id="cite_note-xiang-32"><span class="mw-cite-backlink"><b><a href="#cite_ref-xiang_32-0">^</a></b></span> <span class="reference-text">Xiang Hao, Yongge Wei, Shiwei Zhang (2001): "Synthesis, crystal structure and magnetic property of a binuclear iron(III) citrate complex". <i>Transition Metal Chemistry</i>, volume 26, issue 4, pages 384–387. <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/10.1023%2FA%3A1011055306645">10.1023/A:1011055306645</a></span> </li> <li id="cite_note-shweky-33"><span class="mw-cite-backlink"><b><a href="#cite_ref-shweky_33-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFShwekyBinoGoldbergLippard1994" class="citation journal cs1">Shweky, Itzhak; Bino, Avi; Goldberg, David P.; Lippard, Stephen J. (1994). "Syntheses, Structures, and Magnetic Properties of Two Dinuclear Iron(III) Citrate Complexes". <i>Inorganic Chemistry</i>. <b>33</b> (23): 5161–5162. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fic00101a001">10.1021/ic00101a001</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Inorganic+Chemistry&rft.atitle=Syntheses%2C+Structures%2C+and+Magnetic+Properties+of+Two+Dinuclear+Iron%28III%29+Citrate+Complexes&rft.volume=33&rft.issue=23&rft.pages=5161-5162&rft.date=1994&rft_id=info%3Adoi%2F10.1021%2Fic00101a001&rft.aulast=Shweky&rft.aufirst=Itzhak&rft.au=Bino%2C+Avi&rft.au=Goldberg%2C+David+P.&rft.au=Lippard%2C+Stephen+J.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACitric+acid" class="Z3988"></span></span> </li> <li id="cite_note-34"><span class="mw-cite-backlink"><b><a href="#cite_ref-34">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFJOHNSONQUILLDANIELS1947" class="citation journal cs1">JOHNSON, WARREN C.; QUILL, LAURENCE L.; DANIELS, FARRINGTON (September 1, 1947). <a rel="nofollow" class="external text" href="https://dx.doi.org/10.1021/cen-v025n035.p2494">"Rare Earths Separation Developed on Manhattan Project"</a>. <i>Chemical & Engineering News Archive</i>. <b>25</b> (35): 2494. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fcen-v025n035.p2494">10.1021/cen-v025n035.p2494</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0009-2347">0009-2347</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Chemical+%26+Engineering+News+Archive&rft.atitle=Rare+Earths+Separation+Developed+on+Manhattan+Project&rft.volume=25&rft.issue=35&rft.pages=2494&rft.date=1947-09-01&rft_id=info%3Adoi%2F10.1021%2Fcen-v025n035.p2494&rft.issn=0009-2347&rft.aulast=JOHNSON&rft.aufirst=WARREN+C.&rft.au=QUILL%2C+LAURENCE+L.&rft.au=DANIELS%2C+FARRINGTON&rft_id=http%3A%2F%2Fdx.doi.org%2F10.1021%2Fcen-v025n035.p2494&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACitric+acid" class="Z3988"></span></span> </li> <li id="cite_note-35"><span class="mw-cite-backlink"><b><a href="#cite_ref-35">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSaleemAliRehmanRizwan2020" class="citation journal cs1">Saleem, Muhammad Hamzah; Ali, Shafaqat; Rehman, Muzammal; Rizwan, Muhammad; Kamran, Muhammad; Mohamed, Ibrahim A.A.; Khan, Zaid; Bamagoos, Atif A.; Alharby, Hesham F.; Hakeem, Khalid Rehman; Liu, Lijun (August 1, 2020). <a rel="nofollow" class="external text" href="https://scholar.google.com/scholar?hl=en&as_sdt=0%2C5&q=Individual+and+combined+application+of+EDTA+and+citric+acid+assisted+phytoextraction+of+copper+using+jute+%28Corchorus+capsularis+L.%29+seedlings&btnG=">"Individual and combined application of EDTA and citric acid assisted phytoextraction of copper using jute (Corchorus capsularis L.) seedlings"</a>. <i>Environmental Technology & Innovation</i>. <b>19</b>: 100895. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2020EnvTI..1900895S">2020EnvTI..1900895S</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.eti.2020.100895">10.1016/j.eti.2020.100895</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/2352-1864">2352-1864</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:219432688">219432688</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Environmental+Technology+%26+Innovation&rft.atitle=Individual+and+combined+application+of+EDTA+and+citric+acid+assisted+phytoextraction+of+copper+using+jute+%28Corchorus+capsularis+L.%29+seedlings&rft.volume=19&rft.pages=100895&rft.date=2020-08-01&rft_id=info%3Adoi%2F10.1016%2Fj.eti.2020.100895&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A219432688%23id-name%3DS2CID&rft.issn=2352-1864&rft_id=info%3Abibcode%2F2020EnvTI..1900895S&rft.aulast=Saleem&rft.aufirst=Muhammad+Hamzah&rft.au=Ali%2C+Shafaqat&rft.au=Rehman%2C+Muzammal&rft.au=Rizwan%2C+Muhammad&rft.au=Kamran%2C+Muhammad&rft.au=Mohamed%2C+Ibrahim+A.A.&rft.au=Khan%2C+Zaid&rft.au=Bamagoos%2C+Atif+A.&rft.au=Alharby%2C+Hesham+F.&rft.au=Hakeem%2C+Khalid+Rehman&rft.au=Liu%2C+Lijun&rft_id=https%3A%2F%2Fscholar.google.com%2Fscholar%3Fhl%3Den%26as_sdt%3D0%252C5%26q%3DIndividual%2Band%2Bcombined%2Bapplication%2Bof%2BEDTA%2Band%2Bcitric%2Bacid%2Bassisted%2Bphytoextraction%2Bof%2Bcopper%2Busing%2Bjute%2B%2528Corchorus%2Bcapsularis%2BL.%2529%2Bseedlings%26btnG%3D&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACitric+acid" class="Z3988"></span></span> </li> <li id="cite_note-36"><span class="mw-cite-backlink"><b><a href="#cite_ref-36">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.astm.org/Standards/A967.htm">"ASTM A967 / A967M - 17 Standard Specification for Chemical Passivation Treatments for Stainless Steel Parts"</a>. <i>www.astm.org</i>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=www.astm.org&rft.atitle=ASTM+A967+%2F+A967M+-+17+Standard+Specification+for+Chemical+Passivation+Treatments+for+Stainless+Steel+Parts&rft_id=https%3A%2F%2Fwww.astm.org%2FStandards%2FA967.htm&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACitric+acid" class="Z3988"></span></span> </li> <li id="cite_note-37"><span class="mw-cite-backlink"><b><a href="#cite_ref-37">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFTangYang2018" class="citation journal cs1">Tang, Sheau-Chung; Yang, Jen-Hung (April 10, 2018). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6017965">"Dual Effects of Alpha-Hydroxy Acids on the Skin"</a>. <i>Molecules</i>. <b>23</b> (4): 863. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.3390%2Fmolecules23040863">10.3390/molecules23040863</a></span>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/1420-3049">1420-3049</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6017965">6017965</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/29642579">29642579</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Molecules&rft.atitle=Dual+Effects+of+Alpha-Hydroxy+Acids+on+the+Skin&rft.volume=23&rft.issue=4&rft.pages=863&rft.date=2018-04-10&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6017965%23id-name%3DPMC&rft.issn=1420-3049&rft_id=info%3Apmid%2F29642579&rft_id=info%3Adoi%2F10.3390%2Fmolecules23040863&rft.aulast=Tang&rft.aufirst=Sheau-Chung&rft.au=Yang%2C+Jen-Hung&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6017965&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACitric+acid" class="Z3988"></span></span> </li> <li id="cite_note-38"><span class="mw-cite-backlink"><b><a href="#cite_ref-38">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFStrangKeaneyButterworthNoble2001" class="citation journal cs1">Strang J, Keaney F, Butterworth G, Noble A, Best D (April 2001). "Different forms of heroin and their relationship to cook-up techniques: data on, and explanation of, use of lemon juice and other acids". <i>Subst Use Misuse</i>. <b>36</b> (5): 573–88. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1081%2Fja-100103561">10.1081/ja-100103561</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/11419488">11419488</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:8516420">8516420</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Subst+Use+Misuse&rft.atitle=Different+forms+of+heroin+and+their+relationship+to+cook-up+techniques%3A+data+on%2C+and+explanation+of%2C+use+of+lemon+juice+and+other+acids&rft.volume=36&rft.issue=5&rft.pages=573-88&rft.date=2001-04&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A8516420%23id-name%3DS2CID&rft_id=info%3Apmid%2F11419488&rft_id=info%3Adoi%2F10.1081%2Fja-100103561&rft.aulast=Strang&rft.aufirst=J&rft.au=Keaney%2C+F&rft.au=Butterworth%2C+G&rft.au=Noble%2C+A&rft.au=Best%2C+D&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACitric+acid" class="Z3988"></span></span> </li> <li id="cite_note-39"><span class="mw-cite-backlink"><b><a href="#cite_ref-39">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation news cs1"><a rel="nofollow" class="external text" href="https://money.cnn.com/2004/07/14/news/fortune500/kleenex/">"Tissues that fight germs"</a>. CNN. July 14, 2004<span class="reference-accessdate">. Retrieved <span class="nowrap">May 8,</span> 2008</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Tissues+that+fight+germs&rft.date=2004-07-14&rft_id=https%3A%2F%2Fmoney.cnn.com%2F2004%2F07%2F14%2Fnews%2Ffortune500%2Fkleenex%2F&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACitric+acid" class="Z3988"></span></span> </li> <li id="cite_note-40"><span class="mw-cite-backlink"><b><a href="#cite_ref-40">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFChenAbramowitz2014" class="citation journal cs1">Chen, Wei; Abramowitz, Matthew K. (February 2014). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3946919">"Treatment of Metabolic Acidosis in Patients With CKD"</a>. <i>American Journal of Kidney Diseases</i>. <b>63</b> (2): 311–317. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1053%2Fj.ajkd.2013.06.017">10.1053/j.ajkd.2013.06.017</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0272-6386">0272-6386</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3946919">3946919</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/23932089">23932089</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=American+Journal+of+Kidney+Diseases&rft.atitle=Treatment+of+Metabolic+Acidosis+in+Patients+With+CKD&rft.volume=63&rft.issue=2&rft.pages=311-317&rft.date=2014-02&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3946919%23id-name%3DPMC&rft.issn=0272-6386&rft_id=info%3Apmid%2F23932089&rft_id=info%3Adoi%2F10.1053%2Fj.ajkd.2013.06.017&rft.aulast=Chen&rft.aufirst=Wei&rft.au=Abramowitz%2C+Matthew+K.&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3946919&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACitric+acid" class="Z3988"></span></span> </li> <li id="cite_note-41"><span class="mw-cite-backlink"><b><a href="#cite_ref-41">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20120912054431/http://www.euro-inox.org/pdf/map/Passivating_Pickling_EN.pdf">"Pickling and Passivating Stainless Steel"</a> <span class="cs1-format">(PDF)</span>. Euro-inox.org. Archived from <a rel="nofollow" class="external text" href="http://www.euro-inox.org/pdf/map/Passivating_Pickling_EN.pdf">the original</a> <span class="cs1-format">(PDF)</span> on September 12, 2012<span class="reference-accessdate">. Retrieved <span class="nowrap">2013-01-01</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Pickling+and+Passivating+Stainless+Steel&rft.pub=Euro-inox.org&rft_id=http%3A%2F%2Fwww.euro-inox.org%2Fpdf%2Fmap%2FPassivating_Pickling_EN.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACitric+acid" class="Z3988"></span></span> </li> <li id="cite_note-42"><span class="mw-cite-backlink"><b><a href="#cite_ref-42">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFAnchell" class="citation web cs1">Anchell, Steve. <a rel="nofollow" class="external text" href="http://www.focalpress.com/books/details/9780240810553/">"The Darkroom Cookbook: 3rd Edition (Paperback)"</a>. Focal Press<span class="reference-accessdate">. Retrieved <span class="nowrap">January 1,</span> 2013</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=The+Darkroom+Cookbook%3A+3rd+Edition+%28Paperback%29&rft.pub=Focal+Press&rft.aulast=Anchell&rft.aufirst=Steve&rft_id=http%3A%2F%2Fwww.focalpress.com%2Fbooks%2Fdetails%2F9780240810553%2F&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACitric+acid" class="Z3988"></span></span> </li> <li id="cite_note-43"><span class="mw-cite-backlink"><b><a href="#cite_ref-43">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPubChem" class="citation web cs1">PubChem. <a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/6224">"Sodium citrate"</a>. <i>pubchem.ncbi.nlm.nih.gov</i><span class="reference-accessdate">. Retrieved <span class="nowrap">August 2,</span> 2021</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=pubchem.ncbi.nlm.nih.gov&rft.atitle=Sodium+citrate&rft.au=PubChem&rft_id=https%3A%2F%2Fpubchem.ncbi.nlm.nih.gov%2Fcompound%2F6224&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACitric+acid" class="Z3988"></span></span> </li> <li id="cite_note-44"><span class="mw-cite-backlink"><b><a href="#cite_ref-44">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20200315161916/https://apps.dtic.mil/dtic/tr/fulltext/u2/a295042.pdf">"An Investigation of the Chemistry of Citric Acid in Military Soldering Applications"</a> <span class="cs1-format">(PDF)</span>. June 19, 1995. Archived from <a rel="nofollow" class="external text" href="https://apps.dtic.mil/dtic/tr/fulltext/u2/a295042.pdf">the original</a> <span class="cs1-format">(PDF)</span> on March 15, 2020.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=An+Investigation+of+the+Chemistry+of+Citric+Acid+in+Military+Soldering+Applications&rft.date=1995-06-19&rft_id=https%3A%2F%2Fapps.dtic.mil%2Fdtic%2Ftr%2Ffulltext%2Fu2%2Fa295042.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACitric+acid" class="Z3988"></span></span> </li> <li id="cite_note-45"><span class="mw-cite-backlink"><b><a href="#cite_ref-45">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBergLarssonTiselius1992" class="citation journal cs1">Berg, C.; Larsson, L.; Tiselius, H. G. (1992). <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/1507355/">"The effects of a single evening dose of alkaline citrate on urine composition and calcium stone formation"</a>. <i>The Journal of Urology</i>. <b>148</b> (3 Pt 2): 979–985. <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%2Fs0022-5347%2817%2936795-2">10.1016/s0022-5347(17)36795-2</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0022-5347">0022-5347</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/1507355">1507355</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Journal+of+Urology&rft.atitle=The+effects+of+a+single+evening+dose+of+alkaline+citrate+on+urine+composition+and+calcium+stone+formation&rft.volume=148&rft.issue=3+Pt+2&rft.pages=979-985&rft.date=1992&rft.issn=0022-5347&rft_id=info%3Apmid%2F1507355&rft_id=info%3Adoi%2F10.1016%2Fs0022-5347%2817%2936795-2&rft.aulast=Berg&rft.aufirst=C.&rft.au=Larsson%2C+L.&rft.au=Tiselius%2C+H.+G.&rft_id=https%3A%2F%2Fpubmed.ncbi.nlm.nih.gov%2F1507355%2F&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACitric+acid" class="Z3988"></span></span> </li> <li id="cite_note-46"><span class="mw-cite-backlink"><b><a href="#cite_ref-46">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFR._L._ShrinerS._G._Fordl._J._Roll1931" class="citation journal cs1">R. L. Shriner; S. G. Ford; l. J. Roll (1931). "Itaconic anhydride and itaconic acid". <i>Org. Synth</i>. <b>11</b>: 70. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.15227%2Forgsyn.011.0070">10.15227/orgsyn.011.0070</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Org.+Synth.&rft.atitle=Itaconic+anhydride+and+itaconic+acid&rft.volume=11&rft.pages=70&rft.date=1931&rft_id=info%3Adoi%2F10.15227%2Forgsyn.011.0070&rft.au=R.+L.+Shriner&rft.au=S.+G.+Ford&rft.au=l.+J.+Roll&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACitric+acid" class="Z3988"></span></span> </li> <li id="cite_note-47"><span class="mw-cite-backlink"><b><a href="#cite_ref-47">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFR._L._ShrinerS._G._Fordl._J._Roll1931" class="citation journal cs1">R. L. Shriner; S. G. Ford; l. J. Roll (1931). "Citraconic Anhydride and Citraconic Acid". <i>Org. Synth</i>. <b>28</b>: 28. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.15227%2Forgsyn.011.0028">10.15227/orgsyn.011.0028</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Org.+Synth.&rft.atitle=Citraconic+Anhydride+and+Citraconic+Acid&rft.volume=28&rft.pages=28&rft.date=1931&rft_id=info%3Adoi%2F10.15227%2Forgsyn.011.0028&rft.au=R.+L.+Shriner&rft.au=S.+G.+Ford&rft.au=l.+J.+Roll&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACitric+acid" class="Z3988"></span></span> </li> <li id="cite_note-48"><span class="mw-cite-backlink"><b><a href="#cite_ref-48">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBruce,_W._F.1937" class="citation journal cs1">Bruce, W. F. (1937). "Aconitic Acid". <i>Organic Syntheses</i>. <b>17</b>: 1. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.15227%2Forgsyn.017.0001">10.15227/orgsyn.017.0001</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Organic+Syntheses&rft.atitle=Aconitic+Acid&rft.volume=17&rft.pages=1&rft.date=1937&rft_id=info%3Adoi%2F10.15227%2Forgsyn.017.0001&rft.au=Bruce%2C+W.+F.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACitric+acid" class="Z3988"></span></span> </li> <li id="cite_note-49"><span class="mw-cite-backlink"><b><a href="#cite_ref-49">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRoger_AdamsH._M._ChilesC._F._Rassweiler1925" class="citation journal cs1">Roger Adams; H. M. Chiles; C. F. Rassweiler (1925). "Acetonedicarboxylic Acid". <i><a href="/wiki/Organic_Syntheses" title="Organic Syntheses">Organic Syntheses</a></i>. <b>5</b>: 5. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.15227%2Forgsyn.005.0005">10.15227/orgsyn.005.0005</a></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Organic+Syntheses&rft.atitle=Acetonedicarboxylic+Acid&rft.volume=5&rft.pages=5&rft.date=1925&rft_id=info%3Adoi%2F10.15227%2Forgsyn.005.0005&rft.au=Roger+Adams&rft.au=H.+M.+Chiles&rft.au=C.+F.+Rassweiler&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACitric+acid" class="Z3988"></span>.</span> </li> <li id="cite_note-ICSC-50"><span class="mw-cite-backlink">^ <a href="#cite_ref-ICSC_50-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-ICSC_50-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20180712084742/https://www.cdc.gov/niosh/ipcsneng/neng0855.html">"Citric acid"</a>. <i>International Chemical Safety Cards</i>. <a href="/wiki/NIOSH" class="mw-redirect" title="NIOSH">NIOSH</a>. September 18, 2018. Archived from <a rel="nofollow" class="external text" href="https://www.cdc.gov/niosh/ipcsneng/neng0855.html">the original</a> on July 12, 2018<span class="reference-accessdate">. Retrieved <span class="nowrap">September 9,</span> 2017</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=International+Chemical+Safety+Cards&rft.atitle=Citric+acid&rft.date=2018-09-18&rft_id=https%3A%2F%2Fwww.cdc.gov%2Fniosh%2Fipcsneng%2Fneng0855.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACitric+acid" class="Z3988"></span></span> </li> <li id="cite_note-51"><span class="mw-cite-backlink"><b><a href="#cite_ref-51">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFJ._ZhengF._XiaoL._M._QianZ._R._Zhou2009" class="citation journal cs1">J. Zheng; F. Xiao; L. M. Qian; Z. R. Zhou (December 2009). "Erosion behavior of human tooth enamel in citric acid solution". <i>Tribology International</i>. <b>42</b> (11–12): 1558–1564. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.triboint.2008.12.008">10.1016/j.triboint.2008.12.008</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Tribology+International&rft.atitle=Erosion+behavior+of+human+tooth+enamel+in+citric+acid+solution&rft.volume=42&rft.issue=11%E2%80%9312&rft.pages=1558-1564&rft.date=2009-12&rft_id=info%3Adoi%2F10.1016%2Fj.triboint.2008.12.008&rft.au=J.+Zheng&rft.au=F.+Xiao&rft.au=L.+M.+Qian&rft.au=Z.+R.+Zhou&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACitric+acid" class="Z3988"></span></span> </li> <li id="cite_note-52"><span class="mw-cite-backlink"><b><a href="#cite_ref-52">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://www.livestrong.com/article/147503-the-effect-of-citric-acid-on-tooth-enamel">"Effect of Citric Acid on Tooth Enamel"</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Effect+of+Citric+Acid+on+Tooth+Enamel&rft_id=http%3A%2F%2Fwww.livestrong.com%2Farticle%2F147503-the-effect-of-citric-acid-on-tooth-enamel&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACitric+acid" class="Z3988"></span></span> </li> <li id="cite_note-ib29-53"><span class="mw-cite-backlink"><b><a href="#cite_ref-ib29_53-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBritish_Pharmacopoeia_Commission_Secretariat2009" class="citation web cs1">British Pharmacopoeia Commission Secretariat (2009). <a rel="nofollow" class="external text" href="https://web.archive.org/web/20090411071437/http://www.pharmacopoeia.co.uk/pdf/2009_index.pdf">"Index, BP 2009"</a> <span class="cs1-format">(PDF)</span>. Archived from <a rel="nofollow" class="external text" href="http://www.pharmacopoeia.co.uk/pdf/2009_index.pdf">the original</a> <span class="cs1-format">(PDF)</span> on April 11, 2009<span class="reference-accessdate">. Retrieved <span class="nowrap">February 4,</span> 2010</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Index%2C+BP+2009&rft.date=2009&rft.au=British+Pharmacopoeia+Commission+Secretariat&rft_id=http%3A%2F%2Fwww.pharmacopoeia.co.uk%2Fpdf%2F2009_index.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACitric+acid" class="Z3988"></span></span> </li> <li id="cite_note-jp15-54"><span class="mw-cite-backlink"><b><a href="#cite_ref-jp15_54-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20110722105441/http://jpdb.nihs.go.jp/jp15e/JP15.pdf">"Japanese Pharmacopoeia, Fifteenth Edition"</a> <span class="cs1-format">(PDF)</span>. 2006. Archived from <a rel="nofollow" class="external text" href="http://jpdb.nihs.go.jp/jp15e/JP15.pdf">the original</a> <span class="cs1-format">(PDF)</span> on July 22, 2011<span class="reference-accessdate">. Retrieved <span class="nowrap">4 February</span> 2010</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Japanese+Pharmacopoeia%2C+Fifteenth+Edition&rft.date=2006&rft_id=http%3A%2F%2Fjpdb.nihs.go.jp%2Fjp15e%2FJP15.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACitric+acid" class="Z3988"></span></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=Citric_acid&action=edit&section=17" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1235681985"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1237033735"><div class="side-box side-box-right plainlinks sistersitebox"><link rel="mw-deduplicated-inline-style" 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template">e</abbr></a></li></ul></div><div id="Digestives,_including_enzymes_(A09)" style="font-size:114%;margin:0 4em">Digestives, including <a href="/wiki/Enzyme" title="Enzyme">enzymes</a> (<a href="/wiki/ATC_code_A09" title="ATC code A09">A09</a>)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Enzyme" title="Enzyme">Enzymes</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/Diastase" title="Diastase">Diastase</a></li> <li><a href="/wiki/Pancreatin" class="mw-redirect" title="Pancreatin">Pancreatin</a></li> <li><a href="/wiki/Pancrelipase" class="mw-redirect" title="Pancrelipase">Pancrelipase</a></li> <li><a href="/wiki/Pepsin" title="Pepsin">Pepsin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Acid" title="Acid">Acid</a> preparations</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a class="mw-selflink selflink">Citric acid</a></li> <li><a href="/wiki/Hydrochloric_acid" title="Hydrochloric acid">Hydrochloric acid</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Citrus" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Citrus" title="Template:Citrus"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Citrus" title="Template talk:Citrus"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Citrus" title="Special:EditPage/Template:Citrus"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Citrus" style="font-size:114%;margin:0 4em"><a href="/wiki/Citrus" title="Citrus">Citrus</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">True <a href="/wiki/Species" title="Species">species</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/Australian_lime" title="Australian lime">Australian and Papuan wild limes group</a></li> <li><a href="/wiki/Citron" title="Citron">Citron</a></li> <li><a href="/wiki/Citrus_cavaleriei" title="Citrus cavaleriei">Ichang papeda</a></li> <li><a href="/wiki/Kaffir_lime" title="Kaffir lime">Kaffir lime</a></li> <li><a href="/wiki/Kumquat" title="Kumquat">Kumquats group</a></li> <li><a href="/wiki/Mandarin_orange" title="Mandarin orange">Mandarin orange</a></li> <li><a href="/wiki/Mangshanyegan" class="mw-redirect" title="Mangshanyegan">Mangshanyegan</a></li> <li><a href="/wiki/Citrus_halimii" title="Citrus halimii">Mountain citron</a></li> <li><a href="/wiki/Pomelo" title="Pomelo">Pomelo</a></li> <li><a href="/wiki/Citrus_ryukyuensis" title="Citrus ryukyuensis">Ryukyu mandarin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Major <a href="/wiki/Citrus_hybrid" class="mw-redirect" title="Citrus hybrid">hybrids</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/Grapefruit" title="Grapefruit">Grapefruit</a></li> <li><a href="/wiki/Lemon" title="Lemon">Lemon</a></li> <li><a href="/wiki/Lime_(fruit)" title="Lime (fruit)">Lime</a></li> <li><a href="/wiki/Orange_(fruit)" title="Orange (fruit)">Orange</a> <small>(<a href="/wiki/Citrus_%C3%97_sinensis" title="Citrus × sinensis">sweet orange</a>)</small></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">True and hybrid<br /><a href="/wiki/Cultivar" title="Cultivar">cultivars</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/Citrus_macrophylla" title="Citrus macrophylla">Alemow</a></li> <li><a href="/wiki/Amanatsu" title="Amanatsu">Amanatsu</a></li> <li><a href="/wiki/Assam_lemon" title="Assam lemon">Assam lemon</a></li> <li><a href="/wiki/Bergamot_orange" title="Bergamot orange">Bergamot orange</a></li> <li><a href="/wiki/Bizzarria" title="Bizzarria">Bizzarria</a></li> <li><a href="/wiki/Bitter_orange" title="Bitter orange">Bitter orange</a></li> <li><a href="/wiki/Blood_lime" title="Blood lime">Blood lime</a></li> <li><a href="/wiki/Blood_orange" title="Blood orange">Blood orange</a></li> <li><a href="/wiki/Byeonggyul" title="Byeonggyul">Byeonggyul</a></li> <li><a href="/wiki/Biasong" class="mw-redirect" title="Biasong">Biasong</a></li> <li><a href="/wiki/Cam_s%C3%A0nh" title="Cam sành">Cam sành</a></li> <li><a href="/wiki/Cara_cara_navel" title="Cara cara navel">Cara cara navel</a></li> <li><a href="/wiki/Citrange" title="Citrange">Citrange</a></li> <li><a href="/wiki/Citrumelo" title="Citrumelo">Citrumelo</a></li> <li><a href="/wiki/Clementine" title="Clementine">Clementine</a></li> <li><a href="/wiki/Coorg_orange" title="Coorg orange">Coorg orange</a></li> <li><a href="/wiki/Daidai" title="Daidai">Daidai</a></li> <li><a href="/wiki/Dekopon" title="Dekopon">Dekopon</a></li> <li><a href="/wiki/%27Encore%27_mandarin" title="'Encore' mandarin">Encore</a></li> <li><a href="/wiki/Fairchild_tangerine" title="Fairchild tangerine">Fairchild tangerine</a></li> <li><a href="/wiki/Florentine_citron" title="Florentine citron">Florentine citron</a></li> <li><a href="/wiki/Forbidden_fruit_(citrus)" title="Forbidden fruit (citrus)">Forbidden fruit</a></li> <li><a href="/wiki/Citrus_assamensis" title="Citrus assamensis">Ginger lime</a></li> <li><a href="/wiki/Haruka_(citrus)" title="Haruka (citrus)">Haruka</a></li> <li><a href="/wiki/Hassaku" title="Hassaku">Hassaku</a></li> <li><a href="/wiki/Hebesu" title="Hebesu">Hebesu</a></li> <li><a href="/wiki/Heen_naran" title="Heen naran">Heen naran</a></li> <li><a href="/wiki/Hyuganatsu" title="Hyuganatsu">Hyuganatsu</a></li> <li><a href="/wiki/Imperial_lemon" title="Imperial lemon">Imperial lemon</a></li> <li><a href="/wiki/Citrus_indica" title="Citrus indica">Indian wild orange</a></li> <li><a href="/wiki/Iyokan" title="Iyokan">Iyokan</a></li> <li><a href="/wiki/Jabara_(citrus)" title="Jabara (citrus)">Jabara</a></li> <li><a href="/wiki/Jaffa_orange" title="Jaffa orange">Jaffa orange</a></li> <li><a href="/wiki/Jamaican_tangelo" title="Jamaican tangelo">Jamaican tangelo</a></li> <li><a href="/wiki/Kabbad" title="Kabbad">Kabbad</a></li> <li><a href="/wiki/Kabosu" title="Kabosu">Kabosu</a></li> <li><a href="/wiki/Kaji_Nemu" title="Kaji Nemu">Kaji Nemu</a></li> <li><a href="/wiki/Citrus_gracilis" title="Citrus gracilis">Kakadu lime</a></li> <li><a href="/wiki/Kalpi_(fruit)" title="Kalpi (fruit)">Kalpi</a></li> <li><a href="/wiki/Kanpei" title="Kanpei">Kanpei</a></li> <li><a href="/wiki/Kawachi_bankan" title="Kawachi bankan">Kawachi bankan</a></li> <li><a href="/wiki/Key_lime" title="Key lime">Key lime</a></li> <li><a href="/wiki/Citrus_latipes" title="Citrus latipes">Khasi papeda</a></li> <li><a href="/wiki/Kinkoji_unshiu" title="Kinkoji unshiu">Kinkoji unshiu</a></li> <li><a href="/wiki/Kinnow" title="Kinnow">Kinnow</a></li> <li><a href="/wiki/Kishu_mikan" title="Kishu mikan">Kishu mikan</a></li> <li><a href="/wiki/Kiyomi" title="Kiyomi">Kiyomi</a></li> <li><a href="/wiki/Kobayashi_mikan" title="Kobayashi mikan">Kobayashi mikan</a></li> <li><a href="/wiki/Koji_orange" title="Koji orange">Koji</a></li> <li><a href="/wiki/Komikan_(fruit)" title="Komikan (fruit)">Komikan</a></li> <li><a href="/wiki/Laraha" title="Laraha">Laraha</a></li> <li><a href="/wiki/Lemonade_fruit" title="Lemonade fruit">Lemonade fruit</a></li> <li><a href="/wiki/Lim%C3%B3n_de_Pica" title="Limón de Pica">Limón de Pica</a></li> <li><a href="/wiki/Lumia_(citrus)" title="Lumia (citrus)">Lumia</a></li> <li><a href="/wiki/Mandelo" title="Mandelo">Mandelo</a></li> <li><a href="/wiki/Mandora_(fruit)" title="Mandora (fruit)">Mandora</a></li> <li><a href="/wiki/Citrus_macroptera" title="Citrus macroptera">Melanesian papeda</a></li> <li><a href="/wiki/Melogold" title="Melogold">Melogold</a></li> <li><a href="/wiki/Meyer_lemon" title="Meyer lemon">Meyer lemon</a></li> <li><a href="/wiki/Micrantha_(citrus)" title="Micrantha (citrus)">Micrantha</a></li> <li><a href="/wiki/Midknight_Valencia_Orange" title="Midknight Valencia Orange">Midknight Valencia Orange</a></li> <li><a href="/wiki/Murcott_(fruit)" title="Murcott (fruit)">Murcott</a></li> <li><a href="/wiki/Citrus_myrtifolia" title="Citrus myrtifolia">Myrtle-leaved orange tree</a></li> <li><a href="/wiki/Nagpur_orange" title="Nagpur orange">Nagpur orange</a></li> <li><a href="/wiki/Citrus_%C3%97_amblycarpa" title="Citrus × amblycarpa">Nasnaran</a></li> <li><a href="/wiki/New_Zealand_grapefruit" title="New Zealand grapefruit">New Zealand grapefruit</a></li> <li><a href="/wiki/%C5%8Cgonkan" title="Ōgonkan">Ōgonkan</a></li> <li><a href="/wiki/Orangelo" title="Orangelo">Orangelo/Chironja</a></li> <li><a href="/wiki/Oroblanco" title="Oroblanco">Oroblanco</a></li> <li><a href="/wiki/Palestinian_sweet_lime" title="Palestinian sweet lime">Palestinian sweet lime</a></li> <li><a href="/wiki/Persian_lime" title="Persian lime">Persian lime</a></li> <li><a href="/wiki/Pixie_mandarin" title="Pixie mandarin">Pixie mandarin</a></li> <li><a href="/wiki/Pompia" title="Pompia">Pompia</a></li> <li><a href="/wiki/Ponderosa_lemon" title="Ponderosa lemon">Ponderosa lemon</a></li> <li><a href="/wiki/Ponkan" title="Ponkan">Ponkan</a></li> <li><a href="/wiki/Rangpur_(fruit)" title="Rangpur (fruit)">Rangpur</a></li> <li><a href="/wiki/Reikou" title="Reikou">Reikou</a></li> <li><a href="/wiki/Rhobs_el_Arsa" title="Rhobs el Arsa">Rhobs el Arsa</a></li> <li><a href="/wiki/Rough_lemon" title="Rough lemon">Rough lemon</a></li> <li><a href="/wiki/Samuyao" class="mw-redirect" title="Samuyao">Samuyao</a></li> <li><a href="/wiki/Sanbokan" title="Sanbokan">Sanbokan</a></li> <li><a href="/wiki/Citrus_unshiu" title="Citrus unshiu">Satsuma mandarin</a></li> <li><a href="/wiki/Setoka" title="Setoka">Setoka</a></li> <li><a href="/wiki/Shangjuan" title="Shangjuan">Shangjuan</a></li> <li><a href="/wiki/Shonan_Gold" title="Shonan Gold">Shonan Gold</a></li> <li><a href="/wiki/Smith_Red_Valencia" title="Smith Red Valencia">Smith Red Valencia</a></li> <li><a href="/wiki/Sudachi" title="Sudachi">Sudachi</a></li> <li><a href="/wiki/Koji_orange#Varieties" title="Koji orange">Suruga yuko</a></li> <li><a href="/wiki/Sweet_lemon" title="Sweet lemon">Sweet lemon</a></li> <li><a href="/wiki/Citrus_limetta" title="Citrus limetta">Sweet limetta</a></li> <li><a href="/wiki/Tangelo" title="Tangelo">Tangelo</a></li> <li><a href="/wiki/Tangerine" title="Tangerine">Tangerine</a></li> <li><a href="/wiki/Tangor" title="Tangor">Tangor</a></li> <li><a href="/wiki/Tsunonozomi" title="Tsunonozomi">Tsunonozomi</a></li> <li><a href="/wiki/Valencia_orange" title="Valencia orange">Valencia orange</a></li> <li><a href="/wiki/Variegated_pink_lemon" title="Variegated pink lemon">Variegated pink lemon</a></li> <li><a href="/wiki/Volkamer_lemon" title="Volkamer lemon">Volkamer lemon</a></li> <li><a href="/wiki/Citrus_longispina" title="Citrus longispina">Winged lime</a></li> <li><a href="/wiki/X%C3%A3_%C4%90o%C3%A0i_orange" title="Xã Đoài orange">Xã Đoài orange</a></li> <li><a href="/wiki/Y%C5%ABk%C5%8D" title="Yūkō">Yūkō</a></li> <li><a href="/wiki/Yuzu" title="Yuzu">Yuzu</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Citron" title="Citron">Citrons</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/Balady_citron" title="Balady citron">Balady citron</a></li> <li><a href="/wiki/Corsican_citron" title="Corsican citron">Corsican citron</a></li> <li><a href="/wiki/Diamante_citron" title="Diamante citron">Diamante citron</a></li> <li><a href="/wiki/Fingered_citron" class="mw-redirect" title="Fingered citron">Fingered citron/Buddha's hand</a></li> <li><a href="/wiki/Greek_citron" title="Greek citron">Greek citron</a></li> <li><a href="/wiki/Moroccan_citron" title="Moroccan citron">Moroccan citron</a></li> <li><a href="/wiki/Yemenite_citron" title="Yemenite citron">Yemenite citron</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Mandarin_orange_varieties" title="Mandarin orange varieties">Mandarin oranges</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/Citrus_reshni" title="Citrus reshni">Cleopatra mandarin</a></li> <li><a href="/wiki/Citrus_depressa" title="Citrus depressa">Shīkwāsā</a></li> <li><a href="/wiki/Nanfengmiju" title="Nanfengmiju">Nanfengmiju</a></li> <li><a href="/wiki/Tachibana_orange" title="Tachibana orange">Tachibana</a></li> <li><a href="/wiki/Citrus_x_deliciosa" class="mw-redirect" title="Citrus x deliciosa">Willowleaf orange</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Papeda_(citrus)" title="Papeda (citrus)">Papedas</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/Citrus_celebica" class="mw-redirect" title="Citrus celebica">Celebes papeda</a></li> <li><a href="/wiki/Citrus_halimii" title="Citrus halimii">Mountain "citron"</a></li> <li><a href="/wiki/Citrus_ichangensis" class="mw-redirect" title="Citrus ichangensis">Ichang papeda</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Pomelos" class="mw-redirect" title="Pomelos">Pomelos</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/Banpeiyu" title="Banpeiyu">Banpeiyu</a></li> <li><a href="/wiki/Dangyuja" title="Dangyuja">Dangyuja</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Kumquat" title="Kumquat">Kumquats</a> group</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%">Kumquat species</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/Citrus_hindsii" title="Citrus hindsii">Hong Kong kumquat</a></li> <li><a href="/wiki/Citrus_crassifolia" title="Citrus crassifolia">Meiwa kumquat</a></li> <li><a href="/wiki/Citrus_margarita" title="Citrus margarita">Oval kumquat</a></li> <li><a href="/wiki/Citrus_japonica" title="Citrus japonica">Round kumquat</a></li> <li><a href="/wiki/Citrus_obovata" title="Citrus obovata">Jiangsu kumquat</a></li> <li><a href="/wiki/Citrus_swinglei" title="Citrus swinglei">Malayan kumquat</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Kumquat hybrids <br />(<a href="/wiki/Hybrid_name" title="Hybrid name">×</a> <a href="/wiki/Citrofortunella" title="Citrofortunella">Citrofortunella</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/Calamansi" title="Calamansi">Calamansi</a></li> <li><a href="/wiki/Citrangequat" title="Citrangequat">Citrangequat</a></li> <li><a href="/wiki/Limequat" title="Limequat">Limequat</a></li> <li><a href="/wiki/Mandarinquat" title="Mandarinquat">Mandarinquat</a></li> <li><a href="/wiki/Procimequat" title="Procimequat">Procimequat</a></li> <li><a href="/wiki/Sunquat" title="Sunquat">Sunquat</a></li> <li><a href="/wiki/Yuzuquat" title="Yuzuquat">Yuzuquat</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Australian_lime" title="Australian lime">Australian<br />and Papuan<br />wild limes group</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><i>Eromocitrus</i> <br /> <small>(former genera)</small></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/Citrus_glauca" title="Citrus glauca">Desert lime</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><i>Microcitrus</i> <br /> <small>(former genera)</small></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/Citrus_warburgiana" title="Citrus warburgiana">New Guinea wild lime</a></li> <li><a href="/wiki/Citrus_australis" title="Citrus australis">Australian round lime</a></li> <li><a href="/wiki/Citrus_inodora" title="Citrus inodora">Russell River lime</a></li> <li><a href="/wiki/Citrus_maideniana" class="mw-redirect" title="Citrus maideniana">Maiden's wild lime</a></li> <li><a href="/wiki/Citrus_garrawayi" title="Citrus garrawayi">Mount White lime</a></li> <li><a href="/wiki/Citrus_australasica" title="Citrus australasica">Australian finger lime</a></li> <li><a href="/wiki/Citrus_wintersii" title="Citrus wintersii">Brown River finger lime</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><i><a href="/wiki/Clymenia_(plant)" title="Clymenia (plant)">Clymenia</a></i> <br /> <small>(former genera)</small></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=Clymenia_platypoda&action=edit&redlink=1" class="new" title="Clymenia platypoda (page does not exist)">Clymenia platypoda</a></li> <li><a href="/w/index.php?title=Clymenia_polyandra&action=edit&redlink=1" class="new" title="Clymenia polyandra (page does not exist)">Clymenia polyandra</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><i><a href="/wiki/False_orange" title="False orange">Oxanthera</a></i> <br /> <small>(former genera)</small></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/Citrus_oxanthera" title="Citrus oxanthera">Orange-flowered oxanthera</a></li> <li><a href="/wiki/Citrus_neocaledonica" title="Citrus neocaledonica">Large-leaf oxanthera</a></li> <li><a href="/wiki/Citrus_undulata" title="Citrus undulata">Wavy-leaf oxanthera</a></li> <li><i><a href="/wiki/Oxanthera_brevipes" title="Oxanthera brevipes">Oxanthera brevipes</a></i></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Citrus_taxonomy#Trifoliate_orange" title="Citrus taxonomy">Related genera</a><br />(perhaps<br />properly <i>Citrus</i>)</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i><a href="/wiki/Trifoliate_orange" title="Trifoliate orange">Poncirus</a></i>/<a href="/wiki/Trifoliate_orange" title="Trifoliate orange">Trifoliate orange</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Drinks</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/Calamansi_juice" class="mw-redirect" title="Calamansi juice">Calamansi juice</a></li> <li><a href="/wiki/Ch%C5%ABhai" title="Chūhai">Chūhai</a></li> <li><a href="/wiki/Cura%C3%A7ao_(liqueur)" title="Curaçao (liqueur)">Curaçao</a></li> <li><a href="/wiki/Dried_lime_tea" title="Dried lime tea">Dried lime tea (noomi basra)</a></li> <li><a href="/wiki/Grapefruit_juice" title="Grapefruit juice">Grapefruit juice</a></li> <li><a href="/wiki/Lemonade" title="Lemonade">Lemonade</a></li> <li><a href="/wiki/Limeade" title="Limeade">Limeade</a></li> <li><a href="/wiki/Orange_juice" title="Orange juice">Orange juice</a></li> <li><a href="/wiki/Yuja-hwachae" title="Yuja-hwachae">Yuja-hwachae</a></li> <li><a href="/wiki/Yuja_tea" title="Yuja tea">Yuja tea</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Products</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/Calcium_citrate" title="Calcium citrate">Calcium citrate</a></li> <li><a class="mw-selflink selflink">Citric acid</a></li> <li><a href="/wiki/Biphenyl" title="Biphenyl">Lemonene</a></li> <li><a href="/wiki/Limonene" title="Limonene">Limonene</a></li> <li><a href="/wiki/Neroli" title="Neroli">Neroli</a></li> <li><a href="/wiki/Orange_flower_water" title="Orange flower water">Orange flower water</a></li> <li><a href="/wiki/Orange_oil" title="Orange oil">Orange oil</a></li> <li><a href="/wiki/Orangeat" class="mw-redirect" title="Orangeat">Orangeat</a></li> <li><a href="/wiki/Succade" title="Succade">Succade</a></li> <li><a href="/wiki/Zest_(ingredient)" title="Zest (ingredient)">Zest</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_citrus_diseases" title="List of citrus diseases">Diseases</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/Citrus_black_spot" title="Citrus black spot">Black spot</a></li> <li><a href="/wiki/Citrus_canker" title="Citrus canker">Canker</a></li> <li><a href="/wiki/Citrus_tristeza_virus" title="Citrus tristeza virus">CTV/Tristeza</a></li> <li><a href="/wiki/Citrus_exocortis" title="Citrus exocortis">Exocortis</a></li> <li><a href="/wiki/Citrus_greening_disease" title="Citrus greening disease">Greening</a></li> <li><a href="/wiki/Phoma_tracheiphila" title="Phoma tracheiphila">Mal secco</a></li> <li><a href="/wiki/Phytophthora" title="Phytophthora">Phytophthora</a> <ul><li><a href="/wiki/Phytophthora_citricola" title="Phytophthora citricola">citricola</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Citrus botanists</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/Clara_H._Hasse" title="Clara H. Hasse">Clara H. Hasse</a></li> <li><a href="/wiki/Robert_Willard_Hodgson" title="Robert Willard Hodgson">Robert Willard Hodgson</a></li> <li><a href="/wiki/Lena_B._Smithers_Hughes" title="Lena B. Smithers Hughes">Lena B. Smithers Hughes</a></li> <li><a href="/wiki/David_Mabberley" title="David Mabberley">David Mabberley</a></li> <li><a href="/wiki/Cl%C3%A9ment_Rodier" title="Clément Rodier">Clément Rodier</a></li> <li><a href="/wiki/Robert_Soost" title="Robert Soost">Robert Soost</a></li> <li><a href="/wiki/Walter_Tennyson_Swingle" title="Walter Tennyson Swingle">Walter Tennyson Swingle</a></li> <li><a href="/wiki/Ch%C5%8Dzabur%C5%8D_Tanaka" title="Chōzaburō Tanaka">Chōzaburō Tanaka</a></li> <li><a href="/wiki/Ikuro_Takahashi_(botanist)" title="Ikuro Takahashi (botanist)">Ikuro Takahashi</a></li> <li><a href="/wiki/Johann_Christoph_Volkamer" title="Johann Christoph Volkamer">Johann Christoph Volkamer</a></li> <li><a href="/wiki/Herbert_John_Webber" title="Herbert John Webber">Herbert John Webber</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Related topics</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i><a href="/wiki/The_Citrus_Industry" title="The Citrus Industry">The Citrus Industry</a></i></li> <li><a href="/wiki/Citrus_production" title="Citrus production">Citrus production</a></li> <li><a href="/wiki/Citrus_rootstock" title="Citrus rootstock">Citrus rootstock</a></li> <li><a href="/wiki/Citrus_taxonomy" title="Citrus taxonomy">Citrus taxonomy</a></li> <li><a href="/wiki/Cold-hardy_citrus" title="Cold-hardy citrus">Cold-hardy citrus</a></li> <li><a href="/wiki/Hesperidium" title="Hesperidium">Hesperidium</a></li> <li><a href="/wiki/Japanese_citrus" title="Japanese citrus">Japanese citrus</a></li> <li><a href="/wiki/List_of_citrus_fruits" title="List of citrus fruits">List of citrus fruits</a></li> <li><a href="/wiki/Mother_Orange_Tree" title="Mother Orange Tree">Mother Orange Tree</a></li> <li><a href="/wiki/Orangery" title="Orangery">Orangery</a></li> <li><a href="/wiki/University_of_California_Citrus_Experiment_Station" title="University of California Citrus Experiment Station">University of California Citrus Experiment Station</a></li> <li><a href="/wiki/University_of_California,_Riverside_Citrus_Variety_Collection" title="University of California, Riverside Citrus Variety Collection">University of California, Riverside Citrus Variety Collection</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <ul><li><span class="noviewer" typeof="mw:File"><span title="Category"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/16px-Symbol_category_class.svg.png" decoding="async" width="16" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/23px-Symbol_category_class.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/31px-Symbol_category_class.svg.png 2x" data-file-width="180" data-file-height="185" /></span></span> <b><a href="/wiki/Category:Citrus" 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