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<span>Production</span> </div> </a> <button aria-controls="toc-Production-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Production subsection</span> </button> <ul id="toc-Production-sublist" class="vector-toc-list"> <li id="toc-Industrial" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Industrial"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.1</span> <span>Industrial</span> </div> </a> <ul id="toc-Industrial-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Laboratory" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Laboratory"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.2</span> <span>Laboratory</span> </div> </a> <ul id="toc-Laboratory-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Structure" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Structure"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Structure</span> </div> </a> <button aria-controls="toc-Structure-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 Structure subsection</span> </button> <ul id="toc-Structure-sublist" class="vector-toc-list"> <li id="toc-Anhydrous" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Anhydrous"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.1</span> <span>Anhydrous</span> </div> </a> <ul id="toc-Anhydrous-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Dihydrate" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Dihydrate"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.2</span> <span>Dihydrate</span> </div> </a> <ul id="toc-Dihydrate-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Reactions" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Reactions"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Reactions</span> </div> </a> <button aria-controls="toc-Reactions-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Reactions subsection</span> </button> <ul id="toc-Reactions-sublist" class="vector-toc-list"> <li id="toc-Acid–base_properties" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Acid–base_properties"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.1</span> <span>Acid–base properties</span> </div> </a> <ul id="toc-Acid–base_properties-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Metal-binding_properties" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Metal-binding_properties"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.2</span> <span>Metal-binding properties</span> </div> </a> <ul id="toc-Metal-binding_properties-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Other" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Other"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.3</span> <span>Other</span> </div> </a> <ul id="toc-Other-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Occurrence" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Occurrence"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Occurrence</span> </div> </a> <button aria-controls="toc-Occurrence-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Occurrence subsection</span> </button> <ul id="toc-Occurrence-sublist" class="vector-toc-list"> <li id="toc-Biosynthesis" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Biosynthesis"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1</span> <span>Biosynthesis</span> </div> </a> <ul id="toc-Biosynthesis-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Occurrence_in_foods_and_plants" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Occurrence_in_foods_and_plants"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.2</span> <span>Occurrence in foods and plants</span> </div> </a> <ul id="toc-Occurrence_in_foods_and_plants-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Production_by_fungi" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Production_by_fungi"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.3</span> <span>Production by fungi</span> </div> </a> <ul id="toc-Production_by_fungi-sublist" class="vector-toc-list"> </ul> </li> </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">6</span> <span>Biochemistry</span> </div> </a> <ul id="toc-Biochemistry-sublist" class="vector-toc-list"> </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">7</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-Niche_uses" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Niche_uses"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.1</span> <span>Niche uses</span> </div> </a> <ul id="toc-Niche_uses-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Semiconductor_industry" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Semiconductor_industry"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.2</span> <span>Semiconductor industry</span> </div> </a> <ul id="toc-Semiconductor_industry-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Proposed_uses" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Proposed_uses"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.3</span> <span>Proposed uses</span> </div> </a> <ul id="toc-Proposed_uses-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Content_in_food_items" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Content_in_food_items"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>Content in food items</span> </div> </a> <ul id="toc-Content_in_food_items-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Toxicity" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Toxicity"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>Toxicity</span> </div> </a> <ul id="toc-Toxicity-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Kidney_stones" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Kidney_stones"> <div class="vector-toc-text"> <span class="vector-toc-numb">10</span> <span>Kidney stones</span> </div> </a> <ul id="toc-Kidney_stones-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Notes" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Notes"> <div class="vector-toc-text"> <span class="vector-toc-numb">11</span> <span>Notes</span> </div> </a> <ul id="toc-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">12</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">13</span> <span>External links</span> </div> </a> <ul id="toc-External_links-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" title="Table of Contents" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span class="vector-dropdown-label-text">Toggle the table of contents</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Oxalic 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 66 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-66" 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">66 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/Oksaalsuur" title="Oksaalsuur – Afrikaans" lang="af" hreflang="af" data-title="Oksaalsuur" 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%D8%A3%D9%83%D8%B3%D8%A7%D9%84%D9%8A%D9%83" title="حمض الأكساليك – Arabic" lang="ar" hreflang="ar" data-title="حمض الأكساليك" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-az mw-list-item"><a href="https://az.wikipedia.org/wiki/Oksalat_tur%C5%9Fusu" title="Oksalat turşusu – Azerbaijani" lang="az" hreflang="az" data-title="Oksalat 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%A7%D9%82%D8%B2%D8%A7%D9%84%DB%8C%DA%A9_%D8%A7%D8%B3%DB%8C%D8%AF" title="اقزالیک اسید – South Azerbaijani" lang="azb" hreflang="azb" data-title="اقزالیک 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%85%E0%A6%95%E0%A7%8D%E0%A6%B8%E0%A6%BE%E0%A6%B2%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="অক্সালিক অ্যাসিড – Bangla" lang="bn" hreflang="bn" data-title="অক্সালিক 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/Chh%C3%A1u-sng" title="Chháu-sng – Minnan" lang="nan" hreflang="nan" data-title="Chháu-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%A8%D1%87%D0%B0%D1%9E%D0%B5%D0%B2%D0%B0%D1%8F_%D0%BA%D1%96%D1%81%D0%BB%D0%B0%D1%82%D0%B0" title="Шчаўевая кіслата – Belarusian" lang="be" hreflang="be" data-title="Шчаўевая 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%A8%D1%87%D0%B0%D1%9E%D0%B5%D0%B2%D0%B0%D1%8F_%D0%BA%D1%96%D1%81%D1%8C%D0%BB%D1%8F" title="Шчаўевая кісьля – Belarusian (Taraškievica orthography)" lang="be-tarask" hreflang="be-tarask" data-title="Шчаўевая 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%9E%D0%BA%D1%81%D0%B0%D0%BB%D0%BE%D0%B2%D0%B0_%D0%BA%D0%B8%D1%81%D0%B5%D0%BB%D0%B8%D0%BD%D0%B0" title="Оксалова киселина – Bulgarian" lang="bg" hreflang="bg" data-title="Оксалова киселина" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target"><span>Български</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/%C3%80cid_ox%C3%A0lic" title="Àcid oxàlic – Catalan" lang="ca" hreflang="ca" data-title="Àcid oxàlic" 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_%C5%A1%C5%A5avelov%C3%A1" title="Kyselina šťavelová – Czech" lang="cs" hreflang="cs" data-title="Kyselina šťavelová" 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_ocsalig" title="Asid ocsalig – Welsh" lang="cy" hreflang="cy" data-title="Asid ocsalig" 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/Oxalsyre" title="Oxalsyre – Danish" lang="da" hreflang="da" data-title="Oxalsyre" 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/Oxals%C3%A4ure" title="Oxalsäure – German" lang="de" hreflang="de" data-title="Oxalsäure" 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/Oblikhape" title="Oblikhape – Estonian" lang="et" hreflang="et" data-title="Oblikhape" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%91%CE%B9%CE%B8%CE%B1%CE%BD%CE%BF%CE%B4%CE%B9%CE%B9%CE%BA%CF%8C_%CE%BF%CE%BE%CF%8D" title="Αιθανοδιικό οξύ – Greek" lang="el" hreflang="el" data-title="Αιθανοδιικό 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_ox%C3%A1lico" title="Ácido oxálico – Spanish" lang="es" hreflang="es" data-title="Ácido oxálico" 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/Okzalata_acido" title="Okzalata acido – Esperanto" lang="eo" hreflang="eo" data-title="Okzalata acido" 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_oxaliko" title="Azido oxaliko – Basque" lang="eu" hreflang="eu" data-title="Azido oxaliko" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%A7%DA%AF%D8%B2%D8%A7%D9%84%DB%8C%DA%A9_%D8%A7%D8%B3%DB%8C%D8%AF" title="اگزالیک اسید – Persian" lang="fa" hreflang="fa" data-title="اگزالیک 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_oxalique" title="Acide oxalique – French" lang="fr" hreflang="fr" data-title="Acide oxalique" 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_ocsalach" title="Aigéad ocsalach – Irish" lang="ga" hreflang="ga" data-title="Aigéad ocsalach" 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_ox%C3%A1lico" title="Ácido oxálico – Galician" lang="gl" hreflang="gl" data-title="Ácido oxálico" 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%98%A5%EC%82%B4%EC%82%B0" title="옥살산 – Korean" lang="ko" hreflang="ko" data-title="옥살산" 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%B9%D6%80%D5%A9%D5%B6%D5%BB%D5%A1%D5%AF%D5%A1%D5%A9%D5%A9%D5%B8%D6%82" title="Թրթնջակաթթու – Armenian" lang="hy" hreflang="hy" data-title="Թրթնջակաթթու" 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%91%E0%A4%95%E0%A5%8D%E0%A4%B8%E0%A5%88%E0%A4%B2%E0%A4%BF%E0%A4%95_%E0%A4%85%E0%A4%AE%E0%A5%8D%E0%A4%B2" title="ऑक्सैलिक अम्ल – Hindi" lang="hi" hreflang="hi" data-title="ऑक्सैलिक 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/Oksalna_kiselina" title="Oksalna kiselina – Croatian" lang="hr" hreflang="hr" data-title="Oksalna 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_oksalat" title="Asam oksalat – Indonesian" lang="id" hreflang="id" data-title="Asam oksalat" 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/Oxals%C3%BDra" title="Oxalsýra – Icelandic" lang="is" hreflang="is" data-title="Oxalsýra" 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_ossalico" title="Acido ossalico – Italian" lang="it" hreflang="it" data-title="Acido ossalico" 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%90%D7%95%D7%A7%D7%A1%D7%9C%D7%99%D7%AA" title="חומצה אוקסלית – Hebrew" lang="he" hreflang="he" data-title="חומצה אוקסלית" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-kn mw-list-item"><a href="https://kn.wikipedia.org/wiki/%E0%B2%86%E0%B2%95%E0%B3%8D%E0%B2%B8%E0%B2%BE%E0%B2%B2%E0%B2%BF%E0%B2%95%E0%B3%8D_%E0%B2%86%E0%B2%AE%E0%B3%8D%E0%B2%B2" title="ಆಕ್ಸಾಲಿಕ್ ಆಮ್ಲ – Kannada" lang="kn" hreflang="kn" data-title="ಆಕ್ಸಾಲಿಕ್ 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%9B%E1%83%9F%E1%83%90%E1%83%A3%E1%83%9C%E1%83%9B%E1%83%9F%E1%83%90%E1%83%95%E1%83%90" title="მჟაუნმჟავა – Georgian" lang="ka" hreflang="ka" data-title="მჟაუნმჟავა" data-language-autonym="ქართული" data-language-local-name="Georgian" class="interlanguage-link-target"><span>ქართული</span></a></li><li class="interlanguage-link interwiki-la mw-list-item"><a href="https://la.wikipedia.org/wiki/Acidum_oxalicum" title="Acidum oxalicum – Latin" lang="la" hreflang="la" data-title="Acidum oxalicum" 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/Sk%C4%81be%C5%86sk%C4%81be" title="Skābeņskābe – Latvian" lang="lv" hreflang="lv" data-title="Skābeņskābe" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target"><span>Latviešu</span></a></li><li class="interlanguage-link interwiki-lt mw-list-item"><a href="https://lt.wikipedia.org/wiki/Oksalo_r%C5%ABg%C5%A1tis" title="Oksalo rūgštis – Lithuanian" lang="lt" hreflang="lt" data-title="Oksalo 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/Ox%C3%A1lsav" title="Oxálsav – Hungarian" lang="hu" hreflang="hu" data-title="Oxálsav" 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%9E%D0%BA%D1%81%D0%B0%D0%BB%D0%BD%D0%B0_%D0%BA%D0%B8%D1%81%D0%B5%D0%BB%D0%B8%D0%BD%D0%B0" title="Оксална киселина – Macedonian" lang="mk" hreflang="mk" data-title="Оксална 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%93%E0%B4%95%E0%B5%8D%E0%B4%B8%E0%B4%BE%E0%B4%B2%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="ഓക്സാലിക് ആസിഡ് – Malayalam" lang="ml" hreflang="ml" data-title="ഓക്സാലിക് 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_oksalik" title="Asid oksalik – Malay" lang="ms" hreflang="ms" data-title="Asid oksalik" 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/Oxaalzuur" title="Oxaalzuur – Dutch" lang="nl" hreflang="nl" data-title="Oxaalzuur" 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%B7%E3%83%A5%E3%82%A6%E9%85%B8" title="シュウ酸 – Japanese" lang="ja" hreflang="ja" data-title="シュウ酸" 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/Oksalsyre" title="Oksalsyre – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Oksalsyre" 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/Oksalsyre" title="Oksalsyre – Norwegian Nynorsk" lang="nn" hreflang="nn" data-title="Oksalsyre" 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/Oksalat_kislota" title="Oksalat kislota – Uzbek" lang="uz" hreflang="uz" data-title="Oksalat 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-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Kwas_szczawiowy" title="Kwas szczawiowy – Polish" lang="pl" hreflang="pl" data-title="Kwas szczawiowy" 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_ox%C3%A1lico" title="Ácido oxálico – Portuguese" lang="pt" hreflang="pt" data-title="Ácido oxálico" 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_oxalic" title="Acid oxalic – Romanian" lang="ro" hreflang="ro" data-title="Acid oxalic" 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%A9%D0%B0%D0%B2%D0%B5%D0%BB%D0%B5%D0%B2%D0%B0%D1%8F_%D0%BA%D0%B8%D1%81%D0%BB%D0%BE%D1%82%D0%B0" title="Щавелевая кислота – Russian" lang="ru" hreflang="ru" data-title="Щавелевая кислота" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Oxalic_acid" title="Oxalic acid – Simple English" lang="en-simple" hreflang="en-simple" data-title="Oxalic 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_et%C3%A1ndiov%C3%A1" title="Kyselina etándiová – Slovak" lang="sk" hreflang="sk" data-title="Kyselina etándiová" 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/Oksalna_kislina" title="Oksalna kislina – Slovenian" lang="sl" hreflang="sl" data-title="Oksalna 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/Oksalna_kiselina" title="Oksalna kiselina – Serbian" lang="sr" hreflang="sr" data-title="Oksalna 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/Oksalna_kiselina" title="Oksalna kiselina – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Oksalna 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/Oksaalihappo" title="Oksaalihappo – Finnish" lang="fi" hreflang="fi" data-title="Oksaalihappo" 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/Oxalsyra" title="Oxalsyra – Swedish" lang="sv" hreflang="sv" data-title="Oxalsyra" 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%86%E0%AE%95%E0%AF%8D%E0%AE%9A%E0%AE%BE%E0%AE%B2%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="ஆக்சாலிக் அமிலம் – Tamil" lang="ta" hreflang="ta" data-title="ஆக்சாலிக் 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%86%E0%B0%95%E0%B1%8D%E0%B0%B8%E0%B0%BE%E0%B0%B2%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="ఆక్సాలిక్ ఆమ్లం – Telugu" lang="te" hreflang="te" data-title="ఆక్సాలిక్ ఆమ్లం" data-language-autonym="తెలుగు" data-language-local-name="Telugu" class="interlanguage-link-target"><span>తెలుగు</span></a></li><li class="interlanguage-link interwiki-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B8%81%E0%B8%A3%E0%B8%94%E0%B8%AD%E0%B8%AD%E0%B8%81%E0%B8%8B%E0%B8%B2%E0%B8%A5%E0%B8%B4%E0%B8%81" title="กรดออกซาลิก – Thai" lang="th" hreflang="th" data-title="กรดออกซาลิก" data-language-autonym="ไทย" data-language-local-name="Thai" class="interlanguage-link-target"><span>ไทย</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Oksalik_asit" title="Oksalik asit – Turkish" lang="tr" hreflang="tr" data-title="Oksalik 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%A9%D0%B0%D0%B2%D0%BB%D0%B5%D0%B2%D0%B0_%D0%BA%D0%B8%D1%81%D0%BB%D0%BE%D1%82%D0%B0" title="Щавлева кислота – Ukrainian" lang="uk" hreflang="uk" data-title="Щавлева кислота" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Acid_oxalic" title="Acid oxalic – Vietnamese" lang="vi" hreflang="vi" data-title="Acid oxalic" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target"><span>Tiếng Việt</span></a></li><li class="interlanguage-link interwiki-zh-classical mw-list-item"><a href="https://zh-classical.wikipedia.org/wiki/%E8%8D%89%E9%85%B8" title="草酸 – Literary Chinese" lang="lzh" hreflang="lzh" data-title="草酸" data-language-autonym="文言" data-language-local-name="Literary Chinese" class="interlanguage-link-target"><span>文言</span></a></li><li class="interlanguage-link interwiki-wuu mw-list-item"><a href="https://wuu.wikipedia.org/wiki/%E8%8D%89%E9%85%B8" title="草酸 – Wu" lang="wuu" hreflang="wuu" data-title="草酸" 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/%E8%8D%89%E9%85%B8" title="草酸 – Cantonese" lang="yue" hreflang="yue" data-title="草酸" 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/%E8%8D%89%E9%85%B8" title="草酸 – Chinese" lang="zh" hreflang="zh" data-title="草酸" 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/Q184832#sitelinks-wikipedia" title="Edit interlanguage links" class="wbc-editpage">Edit links</a></span></div> </div> </div> </div> </header> 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.ib-chembox td,.mw-parser-output .ib-chembox th{border:1px solid #a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}</style> <table class="infobox ib-chembox"> <caption>Oxalic acid </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Oxals%C3%A4ure2.svg" class="mw-file-description"><img alt="Structural formula of oxalic acid" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a8/Oxals%C3%A4ure2.svg/140px-Oxals%C3%A4ure2.svg.png" decoding="async" width="140" height="105" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a8/Oxals%C3%A4ure2.svg/210px-Oxals%C3%A4ure2.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a8/Oxals%C3%A4ure2.svg/280px-Oxals%C3%A4ure2.svg.png 2x" data-file-width="824" data-file-height="616" /></a><figcaption></figcaption></figure> </td></tr> <tr> <td colspan="2" class="borderless" style="text-align:center"> <table border="0" style="width:100%;display:inline-table;"> <tbody><tr> <td style="border-right:1px solid #aaa; width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Oxalic_acid_molecule_ball_from_xtal.png" class="mw-file-description"><img alt="Skeletal formula of oxalic acid" src="//upload.wikimedia.org/wikipedia/commons/thumb/4/47/Oxalic_acid_molecule_ball_from_xtal.png/120px-Oxalic_acid_molecule_ball_from_xtal.png" decoding="async" width="120" height="90" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/47/Oxalic_acid_molecule_ball_from_xtal.png/180px-Oxalic_acid_molecule_ball_from_xtal.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/47/Oxalic_acid_molecule_ball_from_xtal.png/240px-Oxalic_acid_molecule_ball_from_xtal.png 2x" data-file-width="3000" data-file-height="2253" /></a><figcaption></figcaption></figure> </td> <td style="width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Oxalic_acid_molecule_spacefill_from_xtal.png" class="mw-file-description"><img alt="Space-filling model of oxalic acid" src="//upload.wikimedia.org/wikipedia/commons/thumb/1/1f/Oxalic_acid_molecule_spacefill_from_xtal.png/120px-Oxalic_acid_molecule_spacefill_from_xtal.png" decoding="async" width="120" height="106" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/1f/Oxalic_acid_molecule_spacefill_from_xtal.png/180px-Oxalic_acid_molecule_spacefill_from_xtal.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/1f/Oxalic_acid_molecule_spacefill_from_xtal.png/240px-Oxalic_acid_molecule_spacefill_from_xtal.png 2x" data-file-width="3000" data-file-height="2652" /></a><figcaption></figcaption></figure> </td></tr></tbody></table> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Oxalic_acid_dihydrate.jpg" class="mw-file-description" title="Oxalic acid dihydrate"><img alt="Oxalic acid dihydrate" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/20/Oxalic_acid_dihydrate.jpg/220px-Oxalic_acid_dihydrate.jpg" decoding="async" width="220" height="165" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/20/Oxalic_acid_dihydrate.jpg/330px-Oxalic_acid_dihydrate.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/20/Oxalic_acid_dihydrate.jpg/440px-Oxalic_acid_dihydrate.jpg 2x" data-file-width="5152" data-file-height="3864" /></a><figcaption>Oxalic acid dihydrate</figcaption></figure><div style="text-align:center;">Oxalic acid dihydrate</div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Chemical_nomenclature" title="Chemical nomenclature">IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">1,2-ethanedioic acid</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;">Oxalic acid<sup id="cite_ref-iupac2013_1-0" class="reference"><a href="#cite_note-iupac2013-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup></div></div> </td></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Chemical_nomenclature#Systematic_name" title="Chemical nomenclature">Systematic IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;">Ethanedioic acid<sup id="cite_ref-iupac2013_1-1" class="reference"><a href="#cite_note-iupac2013-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup></div></div> </td></tr> <tr> <td colspan="2" style="text-align:left;">Other names <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">Wood bleach<br />(Carboxyl)carboxylic acid<br />Carboxylformic acid<br />Dicarboxylic acid<br />Diformic acid</div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><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=144-62-7">144-62-7</a></span> (anhydrous)<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><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=6153-56-6">6153-56-6</a></span> (dihydrate)<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%29C%28%3DO%29O">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Beilstein_database" title="Beilstein database">Beilstein Reference</a></div> </td> <td>385686 </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=16995">CHEBI:16995</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembl/explore/compound/ChEMBL146755">ChEMBL146755</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.946.html">946</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/DB03902">DB03902</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/100.005.123">100.005.123</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q184832#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>205-634-3</li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Gmelin_database" title="Gmelin database">Gmelin Reference</a></div> </td> <td>2208 </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/C00209">C00209</a></span><sup> <span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/Medical_Subject_Headings" title="Medical Subject Headings">MeSH</a> </td> <td><span title="www.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://www.nlm.nih.gov/cgi/mesh/2014/MB_cgi?mode=&term=Oxalic+acid">Oxalic+acid</a></span> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/971">971</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/RTECS" class="mw-redirect" title="RTECS">RTECS number</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li>RO2450000</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/9E7R5L6H31">9E7R5L6H31</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><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/0K2L2IJ59O">0K2L2IJ59O</a></span> (dihydrate)<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/UN_number" title="UN number">UN number</a> </td> <td>3261 </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/DTXSID0025816">DTXSID0025816</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q184832#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></span></li></ul></div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/C6H6O6/c3-1(4)2(5)6/h(H,3,4)(H,5,6)<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: MUBZPKHOEPUJKR-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></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">OC(=O)C(=O)O</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td><span title="Carbon">C</span><sub>2</sub><span title="Hydrogen">H</span><sub>2</sub><span title="Oxygen">O</span><sub>4</sub> </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td><span class="nowrap"><span data-sort-value="7001900340000000000♠"></span>90.034</span> g·mol<sup>−1</sup> (anhydrous)<br />126.065 g·mol<sup>−1</sup> (dihydrate)   </td></tr> <tr> <td>Appearance </td> <td>White crystals </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>1.90 g/cm<sup>3</sup> (anhydrous, at 17 °C)<sup id="cite_ref-GESTIS_2-0" class="reference"><a href="#cite_note-GESTIS-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><br /> 1.653 g/cm<sup>3</sup> (dihydrate) </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>189 to 191 °C (372 to 376 °F; 462 to 464 K) <br />101.5 °C (214.7 °F; 374.6 K) dihydrate </td></tr> <tr> <td><a href="/wiki/Boiling_point" title="Boiling point">Boiling point</a> </td> <td>decomposes (see article for details) </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><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li>In g/L:</li><li>46.9 (5 °C)</li><li>57.2 (10 °C)</li><li>75.5 (15 °C)</li><li>95.5 (20 °C)</li><li>118 (25 °C)</li><li>139 (30 °C)</li><li>178 (35 °C)</li><li>217 (40 °C)</li><li>261 (45 °C)</li><li>315 (50 °C)</li><li>376 (55 °C)</li><li>426 (60 °C)</li><li>548 (65 °C)</li></ul></div><sup id="cite_ref-apel1987_3-0" class="reference"><a href="#cite_note-apel1987-3"><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> </td> <td>237 g/L (15 °C) in <a href="/wiki/Ethanol" title="Ethanol">ethanol</a> <hr /> 14 g/L (15 °C) in <a href="/wiki/Diethyl_ether" title="Diethyl ether">diethyl ether</a><sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Vapor_pressure" title="Vapor pressure">Vapor pressure</a> </td> <td><0.001 mmHg (20 °C)<sup id="cite_ref-PGCH_5-0" class="reference"><a href="#cite_note-PGCH-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Acid_dissociation_constant" title="Acid dissociation constant">Acidity</a> (p<i>K</i><sub>a</sub>) </td> <td>p<i>K</i><sub>a1</sub> = 1.25<br />p<i>K</i><sub>a2</sub> = 4.14<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Conjugate_base" class="mw-redirect" title="Conjugate base">Conjugate base</a> </td> <td><a href="/wiki/Hydrogenoxalate" title="Hydrogenoxalate">Hydrogenoxalate</a> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Magnetic_susceptibility" title="Magnetic susceptibility">Magnetic susceptibility</a> (χ)</div> </td> <td>−60.05·10<sup>−6</sup> cm<sup>3</sup>/mol </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Thermochemistry<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Heat_capacity" title="Heat capacity">Heat capacity</a> <span style="font-size:112%;">(<i>C</i>)</span></div> </td> <td>91.0 J/(mol·K) </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Standard_molar_entropy" title="Standard molar entropy">Std molar<br />entropy</a> <span style="font-size:112%;">(<i>S</i><sup>⦵</sup><sub>298</sub>)</span></div> </td> <td>109.8 J/(mol·K) </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Standard_enthalpy_change_of_formation" class="mw-redirect" title="Standard enthalpy change of formation">Std enthalpy of<br />formation</a> <span style="font-size:112%;">(Δ<sub>f</sub><i>H</i><sup>⦵</sup><sub>298</sub>)</span></div> </td> <td>−829.9 kJ/mol </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Pharmacology </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Anatomical_Therapeutic_Chemical_Classification_System#ATCvet" title="Anatomical Therapeutic Chemical Classification System">ATCvet code</a></div> </td> <td><a href="/wiki/ATC_code_P53" class="mw-redirect" title="ATC code P53">QP53AG03</a> (<span title="www.whocc.no/atcvet"><a rel="nofollow" class="external text" href="https://www.whocc.no/atcvet/atcvet_index/?code=QP53AG03">WHO</a></span>)  </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Hazards </th></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;color:inherit;"><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>Corrosive </td></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;color:inherit;"><a href="/wiki/Globally_Harmonized_System_of_Classification_and_Labelling_of_Chemicals" title="Globally Harmonized System of Classification and Labelling of Chemicals"><b>GHS</b> labelling</a>: </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_hazard_pictograms" title="GHS hazard pictograms">Pictograms</a></div> </td> <td><span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-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><span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-silhouette.svg" class="mw-file-description" title="GHS08: Health hazard"><img alt="GHS08: Health hazard" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/GHS-pictogram-silhouette.svg/50px-GHS-pictogram-silhouette.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/GHS-pictogram-silhouette.svg/75px-GHS-pictogram-silhouette.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/21/GHS-pictogram-silhouette.svg/100px-GHS-pictogram-silhouette.svg.png 2x" data-file-width="724" data-file-height="724" /></a></span> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Globally_Harmonized_System_of_Classification_and_Labelling_of_Chemicals#Signal_word" title="Globally Harmonized System of Classification and Labelling of Chemicals">Signal word</a></div> </td> <td><b>Danger</b> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_hazard_statements" title="GHS hazard statements">Hazard statements</a></div> </td> <td><abbr class="abbr" title="H302+H312: Harmful if swallowed or in contact with skin">H302+H312</abbr>, <abbr class="abbr" title="H318: Causes serious eye damage">H318</abbr>, <abbr class="abbr" title="H402: Harmful to aquatic life">H402</abbr> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_precautionary_statements" title="GHS precautionary statements">Precautionary statements</a></div> </td> <td><abbr class="abbr" title="P264: Wash ... thoroughly after handling.">P264</abbr>, <abbr class="abbr" title="P270: Do not eat, drink or smoke when using this product.">P270</abbr>, <abbr class="abbr" title="P273: Avoid release to the environment.">P273</abbr>, <abbr class="abbr" title="P280: Wear protective gloves/protective clothing/eye protection/face protection.">P280</abbr>, <abbr class="abbr" title="P301+P312+P330: IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell. Rinse mouth.">P301+P312+P330</abbr>, <abbr class="abbr" title="P302+P352+P312: IF ON SKIN: Wash with soap and water. Call a POISON CENTER or doctor/physician if you feel unwell.">P302+P352+P312</abbr>, <abbr class="abbr" title="P305+P351+P338+P310: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do. Continue rinsing. Immediately call a POISON CENTER or doctor/physician.">P305+P351+P338+P310</abbr>, <abbr class="abbr" title="P362+P364: Take off contaminated clothing and wash it before reuse.">P362+P364</abbr>, <abbr class="abbr" title="P501: Dispose of contents/container to ...">P501</abbr> </td></tr> <tr> <td><a href="/wiki/NFPA_704" title="NFPA 704"><b>NFPA 704</b></a> (fire diamond) </td> <td><style data-mw-deduplicate="TemplateStyles:r1170367383">.mw-parser-output .nfpa-704-diamond-ref{float:right;padding:1px;text-align:right}.mw-parser-output .nfpa-704-diamond-container{width:82px;font-family:sans-serif;margin:0 auto}.mw-parser-output .nfpa-704-diamond-container-ref{float:left;margin-left:1em}.mw-parser-output .nfpa-704-diamond-images{float:left;font-size:20px;text-align:center;position:relative;height:80px;width:80px;padding:1px}.mw-parser-output .nfpa-704-diamond-map{position:absolute;height:80px;width:80px}.mw-parser-output .nfpa-704-diamond .noresize{margin:0 auto}.mw-parser-output .nfpa-704-diamond-code{line-height:1em;text-align:center;position:absolute}.mw-parser-output .nfpa-704-diamond-code>a{color:black}.mw-parser-output .nfpa-704-diamond-blue{width:13px;top:31px;left:15px}.mw-parser-output .nfpa-704-diamond-red{width:12px;top:12px;left:35px}.mw-parser-output .nfpa-704-diamond-yellow{width:13px;top:31px;left:54px}.mw-parser-output .nfpa-704-diamond-white-image{position:relative;top:51px;left:0}.mw-parser-output .nfpa-704-diamond-white-text{vertical-align:middle;text-align:center;line-height:80%;position:absolute;top:52px}.mw-parser-output .nfpa-704-diamond-white-text a>span{position:absolute;color:black}.mw-parser-output .nfpa-704-diamond-white-wors{font-size:15px;width:23px;left:29px}.mw-parser-output .nfpa-704-diamond-white-wox{font-size:15px;font-stretch:condensed;width:21px;line-height:80%;top:-4px;left:29px}.mw-parser-output .nfpa-704-diamond-white-abcp{font-size:13.5px;font-stretch:condensed;width:28px;left:26px}.mw-parser-output .nfpa-704-diamond-white-ac{font-size:10px;width:30px;left:25px}.mw-parser-output .nfpa-704-diamond-white-strike{text-decoration:line-through}</style><div class="nfpa-704-diamond notheme"><div class="nfpa-704-diamond-container"><div class="nfpa-704-diamond-images nounderlines"> <div class="nfpa-704-diamond-map"><figure class="noresize" typeof="mw:File"><span><img alt="NFPA 704 four-colored diamond" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/80px-NFPA_704.svg.png" decoding="async" width="80" height="80" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/120px-NFPA_704.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/160px-NFPA_704.svg.png 2x" data-file-width="512" data-file-height="512" usemap="#ImageMap_b74ef64284781bca" /></span><map name="ImageMap_b74ef64284781bca"><area href="/wiki/NFPA_704#Blue" shape="poly" coords="23,23,47,47,23,70,0,47" alt="Health 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gas" title="Health 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gas" /><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 hazard ACID: Acid" title="Special hazard ACID: Acid" /></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 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gas" class="notheme mw-no-invert">3</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 class="nfpa-704-diamond-white-text mw-no-invert"><a href="/wiki/NFPA_704#White" title="NFPA 704"><span class="nfpa-704-diamond-white-ac" title="Special hazard ACID: Acid">ACID</span></a></div></div></div></div> </td></tr> <tr> <td><a href="/wiki/Flash_point" title="Flash point">Flash point</a> </td> <td>166 °C (331 °F; 439 K) </td></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;color:inherit;"><b>Lethal dose</b> or concentration (LD, LC): </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">LD<sub>Lo</sub> (<a href="/wiki/Lethal_dose#LDLo" title="Lethal dose">lowest published</a>)</div> </td> <td>1000 mg/kg (dog, oral)<br />1400 mg/kg (rat)<br />7500 mg/kg (rat, oral)<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;color:inherit;"><a href="/wiki/National_Institute_for_Occupational_Safety_and_Health" title="National Institute for Occupational Safety and Health"><b>NIOSH</b></a> (US health exposure limits): </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Permissible_exposure_limit" title="Permissible exposure limit">PEL</a> (Permissible)</div> </td> <td>TWA 1 mg/m<sup>3</sup><sup id="cite_ref-PGCH_5-1" class="reference"><a href="#cite_note-PGCH-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/Recommended_exposure_limit" title="Recommended exposure limit">REL</a> (Recommended)</div> </td> <td>TWA 1 mg/m<sup>3</sup> ST 2 mg/m<sup>3</sup><sup id="cite_ref-PGCH_5-2" class="reference"><a href="#cite_note-PGCH-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/IDLH" class="mw-redirect" title="IDLH">IDLH</a> (Immediate danger)</div> </td> <td>500 mg/m<sup>3</sup><sup id="cite_ref-PGCH_5-3" class="reference"><a href="#cite_note-PGCH-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Safety_data_sheet" title="Safety data sheet">Safety data sheet</a> (SDS) </td> <td><a rel="nofollow" class="external text" href="https://www.fishersci.com/store/msds?partNumber=AC186432500&productDescription=OXALIC+ACID+ANHYDROUS+250GR&vendorId=VN00032119&countryCode=US&language=en">External MSDS</a> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Related compounds </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Related compounds</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"> <ul><li><a href="/wiki/Oxalyl_chloride" title="Oxalyl chloride">oxalyl chloride</a></li> <li><a href="/wiki/Disodium_oxalate" class="mw-redirect" title="Disodium oxalate">disodium oxalate</a></li> <li><a href="/wiki/Calcium_oxalate" title="Calcium oxalate">calcium oxalate</a></li> <li><a href="/wiki/Phenyl_oxalate_ester" class="mw-redirect" title="Phenyl oxalate ester">phenyl oxalate ester</a></li></ul> </div> </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; color:inherit; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"><div style="text-align:center;"><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/12px-X_mark.svg.png" decoding="async" width="12" height="14" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/18px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/24px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span> <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=476995784&page2=Oxalic+acid">verify</a></span> (<a href="/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validation" title="Wikipedia:WikiProject Chemicals/Chembox validation">what is</a> <sup><span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup> ?) </div></div> <div style="margin-top: 0.3em; text-align: center;"><a href="/wiki/Wikipedia:Chemical_infobox#References" title="Wikipedia:Chemical infobox">Infobox references</a></div> </td></tr> </tbody></table><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound</div> <p><b>Oxalic acid</b> is an <a href="/wiki/Organic_acid" title="Organic acid">organic acid</a> with the systematic name <b>ethanedioic acid</b> and <a href="/wiki/Chemical_formula" title="Chemical formula">chemical formula</a> <style data-mw-deduplicate="TemplateStyles:r1123817410">.mw-parser-output .template-chem2-su{display:inline-block;font-size:80%;line-height:1;vertical-align:-0.35em}.mw-parser-output .template-chem2-su>span{display:block;text-align:left}.mw-parser-output sub.template-chem2-sub{font-size:80%;vertical-align:-0.35em}.mw-parser-output sup.template-chem2-sup{font-size:80%;vertical-align:0.65em}</style><span class="chemf nowrap">HO−C(=O)−C(=O)−OH</span>, also written as <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">(COOH)<sub class="template-chem2-sub">2</sub></span> or <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">(CO<sub class="template-chem2-sub">2</sub>H)<sub class="template-chem2-sub">2</sub></span> or <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">H<sub class="template-chem2-sub">2</sub>C<sub class="template-chem2-sub">2</sub>O<sub class="template-chem2-sub">4</sub></span>. It is the simplest <a href="/wiki/Dicarboxylic_acid" title="Dicarboxylic acid">dicarboxylic acid</a>. It is a white crystalline solid that forms a colorless solution in water. Its name is derived from early investigators who isolated oxalic acid from <a href="/wiki/Flowering_plant" title="Flowering plant">flowering plants</a> of the genus <i><a href="/wiki/Oxalis" title="Oxalis">Oxalis</a></i>, commonly known as wood-sorrels. It occurs naturally in many foods. Excessive ingestion of oxalic acid or prolonged skin contact can be dangerous. </p><p>Oxalic acid has much greater acid strength than <a href="/wiki/Acetic_acid" title="Acetic acid">acetic acid</a>. It is a <a href="/wiki/Reducing_agent" title="Reducing agent">reducing agent</a><sup id="cite_ref-Oxalic_Acid:_Uses_9-0" class="reference"><a href="#cite_note-Oxalic_Acid:_Uses-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> and its <a href="/wiki/Conjugate_base" class="mw-redirect" title="Conjugate base">conjugate bases</a> <a href="/wiki/Hydrogen_oxalate" class="mw-redirect" title="Hydrogen oxalate">hydrogen oxalate</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">HC<sub class="template-chem2-sub">2</sub>O<span class="template-chem2-su"><span>−</span><span>4</span></span></span>) and <a href="/wiki/Oxalate" title="Oxalate">oxalate</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">C<sub class="template-chem2-sub">2</sub>O<span class="template-chem2-su"><span>2−</span><span>4</span></span></span>) are <a href="/wiki/Chelating_agents" class="mw-redirect" title="Chelating agents">chelating agents</a> for metal cations. It is used as a cleaning agent, especially for the removal of <a href="/wiki/Rust" title="Rust">rust</a>, because it forms a water-soluble ferric iron complex, the <a href="/wiki/Ferrioxalate" title="Ferrioxalate">ferrioxalate</a> ion. Oxalic acid typically occurs as the <a href="/wiki/Water_of_crystallization" title="Water of crystallization">dihydrate</a> with the formula <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">H<sub class="template-chem2-sub">2</sub>C<sub class="template-chem2-sub">2</sub>O<sub class="template-chem2-sub">4</sub>·2H<sub>2</sub>O</span>. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="History">History</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Oxalic_acid&action=edit&section=1" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The preparation of salts of oxalic acid from plants had been known, at least since 1745, when the Dutch botanist and physician <a href="/wiki/Herman_Boerhaave" title="Herman Boerhaave">Herman Boerhaave</a> isolated a salt from <a href="/wiki/Oxalis" title="Oxalis">wood sorrel</a>, akin to <a href="/wiki/Kraft_process" title="Kraft process">kraft process</a>.<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> By 1773, François Pierre Savary of Fribourg, Switzerland had isolated oxalic acid from its salt in sorrel.<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>In 1776, Swedish chemists <a href="/wiki/Carl_Wilhelm_Scheele" title="Carl Wilhelm Scheele">Carl Wilhelm Scheele</a> and <a href="/wiki/Torbern_Bergman" title="Torbern Bergman">Torbern Olof Bergman</a><sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> produced oxalic acid by reacting sugar with concentrated <a href="/wiki/Nitric_acid" title="Nitric acid">nitric acid</a>; Scheele called the acid that resulted <i>socker-syra</i> or <i>såcker-syra</i> (sugar acid). By 1784, Scheele had shown that "sugar acid" and oxalic acid from natural sources were identical.<sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> The modern name was introduced along with <a href="/wiki/Chemical_nomenclature#History" title="Chemical nomenclature">many other acid names</a> by <a href="/wiki/Louis-Bernard_Guyton_de_Morveau" title="Louis-Bernard Guyton de Morveau">de Morveau</a>, <a href="/wiki/Lavoisier" class="mw-redirect" title="Lavoisier">Lavoisier</a> and coauthors in 1787.<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p><p>In 1824, the German chemist <a href="/wiki/Friedrich_W%C3%B6hler" title="Friedrich Wöhler">Friedrich Wöhler</a> obtained oxalic acid by reacting <a href="/wiki/Cyanogen" title="Cyanogen">cyanogen</a> with ammonia in aqueous solution.<sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> This experiment may represent the first synthesis of a <a href="/wiki/Natural_product" title="Natural product">natural product</a>.<sup id="cite_ref-Ullmann_16-0" class="reference"><a href="#cite_note-Ullmann-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Production">Production</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Oxalic_acid&action=edit&section=2" title="Edit section: Production"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Industrial">Industrial</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Oxalic_acid&action=edit&section=3" title="Edit section: Industrial"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Oxalic acid is mainly manufactured by the oxidation of <a href="/wiki/Carbohydrate" title="Carbohydrate">carbohydrates</a> or <a href="/wiki/Glucose" title="Glucose">glucose</a> using <a href="/wiki/Nitric_acid" title="Nitric acid">nitric acid</a> or air in the presence of <a href="/wiki/Vanadium_pentoxide" class="mw-redirect" title="Vanadium pentoxide">vanadium pentoxide</a>. Another process uses oxygen to regenerate the nitric acid, using a variety of precursors including <a href="/wiki/Glycolic_acid" title="Glycolic acid">glycolic acid</a> and <a href="/wiki/Ethylene_glycol" title="Ethylene glycol">ethylene glycol</a>.<sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> As of 2011, this process was only used by <a href="/wiki/Mitsubishi" title="Mitsubishi">Mitsubishi</a> in Japan.<sup id="cite_ref-18" class="reference"><a href="#cite_note-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> A newer method entails oxidative <a href="/wiki/Carbonylation" title="Carbonylation">carbonylation</a> of <a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">alcohols</a> to give the <a href="/wiki/Ester" title="Ester">diesters</a> of oxalic acid: </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">4 ROH + 4 CO + O<sub class="template-chem2-sub">2</sub> → 2 (CO<sub class="template-chem2-sub">2</sub>R)<sub class="template-chem2-sub">2</sub> + 2 H<sub class="template-chem2-sub">2</sub>O</span></dd></dl> <p>These diesters are subsequently hydrolyzed to oxalic acid. Approximately 120,000 <a href="/wiki/Tonne" title="Tonne">tonnes</a> are produced annually.<sup id="cite_ref-Ullmann_16-1" class="reference"><a href="#cite_note-Ullmann-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p><p>Historically oxalic acid was obtained exclusively by using caustics, such as sodium or <a href="/wiki/Potassium_hydroxide" title="Potassium hydroxide">potassium hydroxide</a>, on <a href="/wiki/Sawdust" title="Sawdust">sawdust</a>, followed by acidification of the oxalate by mineral acids, such as <a href="/wiki/Sulfuric_acid" title="Sulfuric acid">sulfuric acid</a>.<sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> Oxalic acid can also be formed by the heating of <a href="/wiki/Sodium_formate" title="Sodium formate">sodium formate</a> in the presence of an <a href="/wiki/Alkali" title="Alkali">alkaline</a> catalyst.<sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Laboratory">Laboratory</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Oxalic_acid&action=edit&section=4" title="Edit section: Laboratory"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Although it can be readily purchased, oxalic acid can be prepared in the laboratory by <a href="/wiki/Oxidizer" class="mw-redirect" title="Oxidizer">oxidizing</a> <a href="/wiki/Sucrose" title="Sucrose">sucrose</a> using <a href="/wiki/Nitric_acid" title="Nitric acid">nitric acid</a> in the presence of a small amount of <a href="/wiki/Vanadium_pentoxide" class="mw-redirect" title="Vanadium pentoxide">vanadium pentoxide</a> as a <a href="/wiki/Catalyst" class="mw-redirect" title="Catalyst">catalyst</a>.<sup id="cite_ref-cohen_21-0" class="reference"><a href="#cite_note-cohen-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> </p><p>The hydrated solid can be dehydrated with heat or by <a href="/wiki/Azeotropic_distillation" title="Azeotropic distillation">azeotropic distillation</a>.<sup id="cite_ref-22" class="reference"><a href="#cite_note-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Structure">Structure</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Oxalic_acid&action=edit&section=5" title="Edit section: Structure"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Anhydrous">Anhydrous</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Oxalic_acid&action=edit&section=6" title="Edit section: Anhydrous"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Anhydrous oxalic acid exists as two <a href="/wiki/Polymorphism_(materials_science)" class="mw-redirect" title="Polymorphism (materials science)">polymorphs</a>; in one the <a href="/wiki/Hydrogen-bonding" class="mw-redirect" title="Hydrogen-bonding">hydrogen-bonding</a> results in a chain-like structure, whereas the hydrogen bonding pattern in the other form defines a sheet-like structure.<sup id="cite_ref-23" class="reference"><a href="#cite_note-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> Because the anhydrous material is both acidic and <a href="/wiki/Hydrophilic" class="mw-redirect" title="Hydrophilic">hydrophilic</a> (water seeking), it is used in <a href="/wiki/Esterification" class="mw-redirect" title="Esterification">esterifications</a>. </p> <div class="mw-heading mw-heading3"><h3 id="Dihydrate">Dihydrate</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Oxalic_acid&action=edit&section=7" title="Edit section: Dihydrate"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The dihydrate <span class="chemf nowrap">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">2</sub></span></span>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">2</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"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">4</sub></span></span></span>·2<span class="chemf nowrap">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">2</sub></span></span>O</span> has space group <i>C</i><sup>5</sup><sub>2<i>h</i></sub>–<i>P</i>2<sub>1</sub>/<i>n</i>, with <a href="/wiki/Lattice_parameter" class="mw-redirect" title="Lattice parameter">lattice parameters</a> <span class="nowrap"><i>a</i> = 611.9 <a href="/wiki/Picometre" title="Picometre">pm</a></span>, <span class="nowrap"><i>b</i> = 360.7 pm</span>, <span class="nowrap"><i>c</i> = 1205.7 pm</span>, <span class="nowrap"><i>β</i> = 106°19′</span>, <span class="nowrap"><i>Z</i> = 2</span>.<sup id="cite_ref-sabi1969_24-0" class="reference"><a href="#cite_note-sabi1969-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> The main inter-atomic distances are: C−C 153 pm, C−O<sub>1</sub> 129 pm, C−O<sub>2</sub> 119 pm.<sup id="cite_ref-ahmed1953_25-0" class="reference"><a href="#cite_note-ahmed1953-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Reactions">Reactions</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Oxalic_acid&action=edit&section=8" title="Edit section: Reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Acid–base_properties"><span id="Acid.E2.80.93base_properties"></span>Acid–base properties</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Oxalic_acid&action=edit&section=9" title="Edit section: Acid–base properties"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Oxalic acid's p<i>K</i><sub>a</sub> values vary in the literature from 1.25 to 1.46 and from 3.81 to 4.40.<sup id="cite_ref-26" class="reference"><a href="#cite_note-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-27" class="reference"><a href="#cite_note-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-28" class="reference"><a href="#cite_note-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> The 100th ed of the CRC, released in 2019, has values of 1.25 and 3.81.<sup id="cite_ref-29" class="reference"><a href="#cite_note-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> Oxalic acid is relatively strong compared to other <a href="/wiki/Carboxylic_acid" title="Carboxylic acid">carboxylic acids</a>: </p> <style data-mw-deduplicate="TemplateStyles:r996643573">.mw-parser-output .block-indent{padding-left:3em;padding-right:0;overflow:hidden}</style><div class="block-indent"> <table> <tbody><tr> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">H<sub class="template-chem2-sub">2</sub>C<sub class="template-chem2-sub">2</sub>O<sub class="template-chem2-sub">4</sub> ⇌ HC<sub class="template-chem2-sub">2</sub>O<span class="template-chem2-su"><span>−</span><span>4</span></span> + H<sup class="template-chem2-sup">+</sup></span></td> <td><span class="nowrap">          </span></td> <td>p<i>K</i><sub>a1</sub> = 1.27 </td></tr> <tr> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">HC<sub class="template-chem2-sub">2</sub>O<span class="template-chem2-su"><span>−</span><span>4</span></span> ⇌ C<sub class="template-chem2-sub">2</sub>O<span class="template-chem2-su"><span>2−</span><span>4</span></span> + H<sup class="template-chem2-sup">+</sup></span></td> <td><span class="nowrap">          </span></td> <td>p<i>K</i><sub>a2</sub> = 4.27 </td></tr></tbody></table></div> <p>Oxalic acid undergoes many of the reactions characteristic for other carboxylic acids. It forms esters such as <a href="/wiki/Dimethyl_oxalate" title="Dimethyl oxalate">dimethyl oxalate</a> (<a href="/wiki/Melting_point" title="Melting point">m.p.</a> 52.5 to 53.5 °C, 126.5 to 128.3 °F).<sup id="cite_ref-30" class="reference"><a href="#cite_note-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> It forms an acid chloride called <a href="/wiki/Oxalyl_chloride" title="Oxalyl chloride">oxalyl chloride</a>. </p> <div class="mw-heading mw-heading3"><h3 id="Metal-binding_properties">Metal-binding properties</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Oxalic_acid&action=edit&section=10" title="Edit section: Metal-binding properties"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Transition_metal_oxalate_complex" title="Transition metal oxalate complex">Transition metal oxalate complexes</a> are numerous, e.g. the drug <a href="/wiki/Oxaliplatin" title="Oxaliplatin">oxaliplatin</a>. Oxalic acid has been shown to reduce <a href="/wiki/Manganese_dioxide" title="Manganese dioxide">manganese dioxide</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">MnO<sub class="template-chem2-sub">2</sub></span> in <a href="/wiki/Manganese" title="Manganese">manganese</a> ores to allow the leaching of the metal by <a href="/wiki/Sulfuric_acid" title="Sulfuric acid">sulfuric acid</a>.<sup id="cite_ref-31" class="reference"><a href="#cite_note-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> </p><p>Oxalic acid is an important reagent in <a href="/wiki/Lanthanide" title="Lanthanide">lanthanide</a> chemistry. Hydrated lanthanide oxalates form readily in very strongly acidic solutions as a densely <a href="/wiki/Crystalline" class="mw-redirect" title="Crystalline">crystalline</a>, easily filtered form, largely free of contamination by nonlanthanide elements: </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">2 Ln<sup>3+</sup> + 3 H<sub class="template-chem2-sub">2</sub>C<sub class="template-chem2-sub">2</sub>O<sub class="template-chem2-sub">4</sub> → Ln<sub class="template-chem2-sub">2</sub>(C<sub class="template-chem2-sub">2</sub>O<sub class="template-chem2-sub">4</sub>)<sub class="template-chem2-sub">3</sub> + 6 H<sup class="template-chem2-sup">+</sup></span></dd></dl> <p>Thermal decomposition of these oxalates gives the <a href="/wiki/Oxide" title="Oxide">oxides</a>, which is the most commonly marketed form of these elements.<sup id="cite_ref-32" class="reference"><a href="#cite_note-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Other">Other</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Oxalic_acid&action=edit&section=11" title="Edit section: Other"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Oxalic acid and oxalates can be oxidized by <a href="/wiki/Permanganate" title="Permanganate">permanganate</a> in an <a href="/wiki/Autocatalytic" class="mw-redirect" title="Autocatalytic">autocatalytic</a> reaction.<sup id="cite_ref-33" class="reference"><a href="#cite_note-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> </p><p>Oxalic acid vapor decomposes at 125–175 <a href="/wiki/Celsius" title="Celsius">°C</a> into <a href="/wiki/Carbon_dioxide" title="Carbon dioxide">carbon dioxide</a> <span class="chemf nowrap">CO<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">2</sub></span></span></span> and <a href="/wiki/Formic_acid" title="Formic acid">formic acid</a> HCOOH. <a href="/wiki/Photolysis" class="mw-redirect" title="Photolysis">Photolysis</a> with 237–313 <a href="/wiki/Nanometre" title="Nanometre">nm</a> <a href="/wiki/Ultraviolet" title="Ultraviolet">UV</a> light also produces <a href="/wiki/Carbon_monoxide" title="Carbon monoxide">carbon monoxide</a> CO and water.<sup id="cite_ref-zhou1997_34-0" class="reference"><a href="#cite_note-zhou1997-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> </p><p>Evaporation of a solution of <a href="/wiki/Urea" title="Urea">urea</a> and oxalic acid in 2:1 molar ratio yields a solid crystalline compound <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">H<sub class="template-chem2-sub">2</sub>C<sub class="template-chem2-sub">2</sub>O<sub class="template-chem2-sub">4</sub>·2CO(NH<sub class="template-chem2-sub">2</sub>)<sub class="template-chem2-sub">2</sub></span>, consisting of stacked two-dimensional networks of the neutral molecules held together by <a href="/wiki/Hydrogen_bond" title="Hydrogen bond">hydrogen bonds</a> with the oxygen atoms.<sup id="cite_ref-hark1972_35-0" class="reference"><a href="#cite_note-hark1972-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Occurrence">Occurrence</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Oxalic_acid&action=edit&section=12" title="Edit section: Occurrence"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Biosynthesis">Biosynthesis</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Oxalic_acid&action=edit&section=13" title="Edit section: Biosynthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>At least two pathways exist for the enzyme-mediated formation of oxalate. In one pathway, <a href="/wiki/Oxaloacetate" class="mw-redirect" title="Oxaloacetate">oxaloacetate</a>, a component of the <a href="/wiki/Krebs_citric_acid_cycle" class="mw-redirect" title="Krebs citric acid cycle">Krebs citric acid cycle</a>, is hydrolyzed to oxalate and acetic acid by the enzyme <a href="/wiki/Oxaloacetase" title="Oxaloacetase">oxaloacetase</a>:<sup id="cite_ref-36" class="reference"><a href="#cite_note-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">[O<sub class="template-chem2-sub">2</sub>CC(O)CH<sub class="template-chem2-sub">2</sub>CO<sub class="template-chem2-sub">2</sub>]<sup>2−</sup> + H<sub class="template-chem2-sub">2</sub>O → C<sub class="template-chem2-sub">2</sub>O<span class="template-chem2-su"><span>2−</span><span>4</span></span> + CH<sub class="template-chem2-sub">3</sub>CO<span class="template-chem2-su"><span>−</span><span>2</span></span> + H<sup class="template-chem2-sup">+</sup></span></dd></dl> <p>It also arises from the dehydrogenation of <a href="/wiki/Glycolic_acid" title="Glycolic acid">glycolic acid</a>, which is produced by the metabolism of <a href="/wiki/Ethylene_glycol" title="Ethylene glycol">ethylene glycol</a>. </p> <div class="mw-heading mw-heading3"><h3 id="Occurrence_in_foods_and_plants">Occurrence in foods and plants<span class="anchor" id="found_in_foods_plants"></span></h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Oxalic_acid&action=edit&section=14" title="Edit section: Occurrence in foods and plants"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:OxalisTriangularis.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a1/OxalisTriangularis.jpg/220px-OxalisTriangularis.jpg" decoding="async" width="220" height="165" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a1/OxalisTriangularis.jpg/330px-OxalisTriangularis.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a1/OxalisTriangularis.jpg/440px-OxalisTriangularis.jpg 2x" data-file-width="2816" data-file-height="2112" /></a><figcaption>Stems of <i><a href="/wiki/Oxalis_triangularis" title="Oxalis triangularis">Oxalis triangularis</a></i> contain oxalic acid.</figcaption></figure> <p>Early investigators isolated oxalic acid from <a href="/wiki/Oxalis" title="Oxalis">wood-sorrel</a> (<i>Oxalis</i>). Members of the <a href="/wiki/Spinach" title="Spinach">spinach</a> family and the <a href="/wiki/Brassica" title="Brassica">brassicas</a> (<a href="/wiki/Cabbage" title="Cabbage">cabbage</a>, <a href="/wiki/Broccoli" title="Broccoli">broccoli</a>, <a href="/wiki/Brussels_sprouts" class="mw-redirect" title="Brussels sprouts">brussels sprouts</a>) are high in oxalates, as are <a href="/wiki/Sorrel" title="Sorrel">sorrel</a> and <a href="/wiki/Umbellifer" class="mw-redirect" title="Umbellifer">umbellifers</a> like <a href="/wiki/Parsley" title="Parsley">parsley</a>.<sup id="cite_ref-37" class="reference"><a href="#cite_note-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup> The leaves and stems of all species of the genus <i><a href="/wiki/Chenopodium" title="Chenopodium">Chenopodium</a></i> and related genera of the family <a href="/wiki/Amaranthaceae" title="Amaranthaceae">Amaranthaceae</a>, which includes <a href="/wiki/Quinoa" title="Quinoa">quinoa</a>, contain high levels of oxalic acid.<sup id="cite_ref-oxalic_acid_quinoa_leaves_38-0" class="reference"><a href="#cite_note-oxalic_acid_quinoa_leaves-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Rhubarb" title="Rhubarb">Rhubarb</a> leaves contain about 0.5% oxalic acid, and jack-in-the-pulpit (<i><a href="/wiki/Arisaema_triphyllum" title="Arisaema triphyllum">Arisaema triphyllum</a></i>) contains <a href="/wiki/Calcium_oxalate" title="Calcium oxalate">calcium oxalate</a> crystals. Similarly, the <a href="/wiki/Parthenocissus_quinquefolia" title="Parthenocissus quinquefolia">Virginia creeper</a>, a common decorative vine, produces oxalic acid in its berries as well as oxalate crystals in the sap, in the form of <a href="/wiki/Raphide" title="Raphide">raphides</a>. Bacteria produce oxalates from oxidation of <a href="/wiki/Carbohydrate" title="Carbohydrate">carbohydrates</a>.<sup id="cite_ref-Ullmann_16-2" class="reference"><a href="#cite_note-Ullmann-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p><p>Plants of the genus <i><a href="/wiki/Fenestraria" title="Fenestraria">Fenestraria</a></i> produce optical fibers made from crystalline oxalic acid to transmit light to subterranean photosynthetic sites.<sup id="cite_ref-39" class="reference"><a href="#cite_note-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup> </p><p><a href="/wiki/Carambola" title="Carambola">Carambola</a>, also known as starfruit, also contains oxalic acid along with <a href="/wiki/Caramboxin" title="Caramboxin">caramboxin</a>. Citrus juice contains small amounts of oxalic acid. </p><p>The formation of naturally occurring calcium oxalate <a href="/wiki/Patina" title="Patina">patinas</a> on certain <a href="/wiki/Limestone" title="Limestone">limestone</a> and <a href="/wiki/Marble" title="Marble">marble</a> statues and monuments has been proposed to be caused by the chemical reaction of the carbonate stone with oxalic acid secreted by <a href="/wiki/Lichen" title="Lichen">lichen</a> or other <a href="/wiki/Microorganisms" class="mw-redirect" title="Microorganisms">microorganisms</a>.<sup id="cite_ref-40" class="reference"><a href="#cite_note-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-41" class="reference"><a href="#cite_note-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Production_by_fungi">Production by fungi</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Oxalic_acid&action=edit&section=15" title="Edit section: Production by fungi"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Many soil fungus species secrete oxalic acid, which results in greater solubility of metal cations and increased availability of certain soil nutrients, and can lead to the formation of calcium oxalate crystals.<sup id="cite_ref-42" class="reference"><a href="#cite_note-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-43" class="reference"><a href="#cite_note-43"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup> Some fungi such as <i><a href="/wiki/Aspergillus_niger" title="Aspergillus niger">Aspergillus niger</a></i> have been extensively studied for the industrial production of oxalic acid;<sup id="cite_ref-stra1994_44-0" class="reference"><a href="#cite_note-stra1994-44"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup> however, those processes are not yet economically competitive with production from oil and gas.<sup id="cite_ref-tkacz2012_45-0" class="reference"><a href="#cite_note-tkacz2012-45"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup> <i><a href="/wiki/Cryphonectria_parasitica" class="mw-redirect" title="Cryphonectria parasitica">Cryphonectria parasitica</a></i> may excrete oxalic acid containing solutions at the advancing edge of its chestnut <a href="/wiki/Cambium" title="Cambium">cambium</a> infection. The lower pH (<2.5) of more concentrated oxalic acid excretions may degrade cambium cell walls and have a toxic effect on chestnut cambium cells. Cambium cells that burst provide nutrients for a blight infection advance. <sup id="cite_ref-46" class="reference"><a href="#cite_note-46"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup> <sup id="cite_ref-47" class="reference"><a href="#cite_note-47"><span class="cite-bracket">[</span>47<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=Oxalic_acid&action=edit&section=16" title="Edit section: Biochemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The <a href="/wiki/Conjugate_base" class="mw-redirect" title="Conjugate base">conjugate base</a> of oxalic acid is the hydrogenoxalate anion, and its conjugate base (<a href="/wiki/Oxalate" title="Oxalate">oxalate</a>) is a <a href="/wiki/Competitive_inhibitor" class="mw-redirect" title="Competitive inhibitor">competitive inhibitor</a> of the <a href="/wiki/Lactate_dehydrogenase" title="Lactate dehydrogenase">lactate dehydrogenase</a> (LDH) enzyme.<sup id="cite_ref-48" class="reference"><a href="#cite_note-48"><span class="cite-bracket">[</span>48<span class="cite-bracket">]</span></a></sup> LDH catalyses the conversion of <a href="/wiki/Pyruvate" class="mw-redirect" title="Pyruvate">pyruvate</a> to <a href="/wiki/Lactic_acid" title="Lactic acid">lactic acid</a> (end product of the fermentation (anaerobic) process) oxidising the coenzyme <a href="/wiki/NADH" class="mw-redirect" title="NADH">NADH</a> to <a href="/wiki/NAD%2B" class="mw-redirect" title="NAD+">NAD<sup>+</sup></a> and <a href="/wiki/Hydron_(chemistry)" title="Hydron (chemistry)">H<sup>+</sup></a> concurrently. Restoring NAD<sup>+</sup> levels is essential to the continuation of anaerobic energy metabolism through <a href="/wiki/Glycolysis" title="Glycolysis">glycolysis</a>. As cancer cells preferentially use anaerobic metabolism (see <a href="/wiki/Warburg_effect_(oncology)" title="Warburg effect (oncology)">Warburg effect</a>) inhibition of LDH has been shown to inhibit tumor formation and growth,<sup id="cite_ref-49" class="reference"><a href="#cite_note-49"><span class="cite-bracket">[</span>49<span class="cite-bracket">]</span></a></sup> thus is an interesting potential course of cancer treatment. </p><p>Oxalic acid plays a key role in the interaction between pathogenic fungi and plants. Small amounts of oxalic acid enhances plant resistance to fungi, but higher amounts cause widespread programmed cell death of the plant and help with fungi infection. Plants normally produce it in small amounts, but some pathogenic fungi such as <i><a href="/wiki/Sclerotinia_sclerotiorum" title="Sclerotinia sclerotiorum">Sclerotinia sclerotiorum</a></i> cause a toxic accumulation.<sup id="cite_ref-50" class="reference"><a href="#cite_note-50"><span class="cite-bracket">[</span>50<span class="cite-bracket">]</span></a></sup> </p><p>Oxalate, besides being biosynthesised, may also be biodegraded. <i><a href="/wiki/Oxalobacter_formigenes" title="Oxalobacter formigenes">Oxalobacter formigenes</a></i> is an important gut bacterium that helps animals (including humans) degrade oxalate.<sup id="cite_ref-51" class="reference"><a href="#cite_note-51"><span class="cite-bracket">[</span>51<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Applications">Applications</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Oxalic_acid&action=edit&section=17" title="Edit section: Applications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Oxalic acid's main applications include cleaning or bleaching, especially for the removal of rust (iron complexing agent). Its utility in rust removal agents is due to its forming a stable, water-soluble salt with ferric iron, <a href="/wiki/Sodium_ferrioxalate" title="Sodium ferrioxalate">ferrioxalate</a> ion. Oxalic acid is an ingredient in some tooth whitening products. About 25% of produced oxalic acid is used as a <a href="/wiki/Mordant" title="Mordant">mordant</a> in dyeing processes. It is also used in <a href="/wiki/Bleach_(chemical)" class="mw-redirect" title="Bleach (chemical)">bleaches</a>, especially for <a href="/wiki/Pulpwood" title="Pulpwood">pulpwood</a>, cork, straw, cane, feathers, and for rust removal and other cleaning, in baking powder, and as a third reagent in silica analysis instruments. </p> <div class="mw-heading mw-heading3"><h3 id="Niche_uses">Niche uses</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Oxalic_acid&action=edit&section=18" title="Edit section: Niche uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Beecrystals.PNG" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/23/Beecrystals.PNG/220px-Beecrystals.PNG" decoding="async" width="220" height="190" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/23/Beecrystals.PNG/330px-Beecrystals.PNG 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/23/Beecrystals.PNG/440px-Beecrystals.PNG 2x" data-file-width="773" data-file-height="668" /></a><figcaption>Honeybee coated with oxalate crystals</figcaption></figure> <p>Oxalic acid is used by some <a href="/wiki/Beekeeper" title="Beekeeper">beekeepers</a> as a <a href="/wiki/Miticide" class="mw-redirect" title="Miticide">miticide</a> against the parasitic <a href="/wiki/Varroa_destructor" title="Varroa destructor">varroa mite</a>.<sup id="cite_ref-52" class="reference"><a href="#cite_note-52"><span class="cite-bracket">[</span>52<span class="cite-bracket">]</span></a></sup> </p><p>Dilute solutions (0.05–0.15 <a href="/wiki/Molar_concentration" title="Molar concentration">M</a>) of oxalic acid can be used to remove iron from clays such as <a href="/wiki/Kaolinite" title="Kaolinite">kaolinite</a> to produce light-colored <a href="/wiki/Ceramic" title="Ceramic">ceramics</a>.<sup id="cite_ref-lee2007_53-0" class="reference"><a href="#cite_note-lee2007-53"><span class="cite-bracket">[</span>53<span class="cite-bracket">]</span></a></sup> </p><p>Oxalic acid can be used to clean minerals like many other acids. Two such examples are quartz crystals and pyrite.<sup id="cite_ref-54" class="reference"><a href="#cite_note-54"><span class="cite-bracket">[</span>54<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-55" class="reference"><a href="#cite_note-55"><span class="cite-bracket">[</span>55<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-56" class="reference"><a href="#cite_note-56"><span class="cite-bracket">[</span>56<span class="cite-bracket">]</span></a></sup> </p><p>Oxalic acid is sometimes used in the aluminum <a href="/wiki/Anodizing" title="Anodizing">anodizing</a> process, with or without sulfuric acid.<sup id="cite_ref-57" class="reference"><a href="#cite_note-57"><span class="cite-bracket">[</span>57<span class="cite-bracket">]</span></a></sup> Compared to sulfuric-acid anodizing, the coatings obtained are thinner and exhibit lower surface roughness. </p><p>Oxalic acid is also widely used as a wood bleach, most often in its crystalline form to be mixed with water to its proper dilution for use.<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. (March 2023)">citation needed</span></a></i>]</sup> </p> <div class="mw-heading mw-heading3"><h3 id="Semiconductor_industry">Semiconductor industry</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Oxalic_acid&action=edit&section=19" title="Edit section: Semiconductor industry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Oxalic acid is also used in electronic and semiconductor industries. In 2006 it was reported being used in <a href="/wiki/Chemical-mechanical_polishing" title="Chemical-mechanical polishing">electrochemical–mechanical planarization</a> of copper layers in the semiconductor devices fabrication process.<sup id="cite_ref-58" class="reference"><a href="#cite_note-58"><span class="cite-bracket">[</span>58<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Proposed_uses">Proposed uses</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Oxalic_acid&action=edit&section=20" title="Edit section: Proposed uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Reduction of <a href="/wiki/Carbon_dioxide" title="Carbon dioxide">carbon dioxide</a> to oxalic acid by various methods, such as <a href="/wiki/Electrosynthesis" title="Electrosynthesis">electrocatalysis</a> using a <a href="/wiki/Copper" title="Copper">copper</a> complex,<sup id="cite_ref-59" class="reference"><a href="#cite_note-59"><span class="cite-bracket">[</span>59<span class="cite-bracket">]</span></a></sup> is under study as a proposed chemical intermediate for <a href="/wiki/Carbon_capture_and_utilization" class="mw-redirect" title="Carbon capture and utilization">carbon capture and utilization</a>.<sup id="cite_ref-60" class="reference"><a href="#cite_note-60"><span class="cite-bracket">[</span>60<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Content_in_food_items">Content in food items</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Oxalic_acid&action=edit&section=21" title="Edit section: Content in food items"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><sup id="cite_ref-61" class="reference"><a href="#cite_note-61"><span class="cite-bracket">[</span>61<span class="cite-bracket">]</span></a></sup><sup class="noprint Inline-Template" style="margin-left:0.1em; white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Please_clarify" title="Wikipedia:Please clarify"><span title="data in this chart, which is copied from the 1984 USDA publication cited, is inconsistent with more recent studies. Several listed values are off by a factor of 10, which is significant. (December 2018)">clarification needed</span></a></i>]</sup> </p><p><br /> </p> <table class="wikitable sortable"> <tbody><tr> <th>Vegetable</th> <th>Content of oxalic acid<br />(%)<sup class="plainlinks nourlexpansion citation" id="ref_reference_name_A"><a href="#endnote_reference_name_A">a</a></sup> </th></tr> <tr> <td><a href="/wiki/Amaranth" title="Amaranth">Amaranth</a></td> <td><span data-sort-value="7000109000000000000♠" style="display:none"></span> 1.09 </td></tr> <tr> <td><a href="/wiki/Asparagus" title="Asparagus">Asparagus</a></td> <td><span data-sort-value="6999130000000000000♠" style="display:none"></span> 0.13 </td></tr> <tr> <td><a href="/wiki/Snap_beans" class="mw-redirect" title="Snap beans">Beans, snap</a></td> <td><span data-sort-value="6999360000000000000♠" style="display:none"></span> 0.36 </td></tr> <tr> <td><a href="/wiki/Beet" class="mw-redirect" title="Beet">Beet</a> leaves</td> <td><span data-sort-value="6999610000000000000♠" style="display:none"></span> 0.61 </td></tr> <tr> <td><a href="/wiki/Beetroot" title="Beetroot">Beetroot</a></td> <td><span data-sort-value="6998600000000000000♠" style="display:none"></span> 0.06<sup id="cite_ref-ReferenceA_62-0" class="reference"><a href="#cite_note-ReferenceA-62"><span class="cite-bracket">[</span>62<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Broccoli" title="Broccoli">Broccoli</a></td> <td><span data-sort-value="6999190000000000000♠" style="display:none"></span> 0.19 </td></tr> <tr> <td><a href="/wiki/Brussels_sprouts" class="mw-redirect" title="Brussels sprouts">Brussels sprouts</a></td> <td><span data-sort-value="6998200000000000000♠" style="display:none"></span> 0.02<sup id="cite_ref-ReferenceA_62-1" class="reference"><a href="#cite_note-ReferenceA-62"><span class="cite-bracket">[</span>62<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Cabbage" title="Cabbage">Cabbage</a></td> <td><span data-sort-value="6999100000000000000♠" style="display:none"></span> 0.10 </td></tr> <tr> <td><a href="/wiki/Carrot" title="Carrot">Carrot</a></td> <td><span data-sort-value="6999500000000000000♠" style="display:none"></span> 0.50 </td></tr> <tr> <td><a href="/wiki/Cassava" title="Cassava">Cassava</a></td> <td><span data-sort-value="7000126000000000000♠" style="display:none"></span> 1.26 </td></tr> <tr> <td><a href="/wiki/Cauliflower" title="Cauliflower">Cauliflower</a></td> <td><span data-sort-value="6999150000000000000♠" style="display:none"></span> 0.15 </td></tr> <tr> <td><a href="/wiki/Celery" title="Celery">Celery</a></td> <td><span data-sort-value="6999190000000000000♠" style="display:none"></span> 0.19 </td></tr> <tr> <td><a href="/wiki/Chicory" title="Chicory">Chicory</a></td> <td><span data-sort-value="6999210000000000000♠" style="display:none"></span> 0.2 </td></tr> <tr> <td><a href="/wiki/Chives" title="Chives">Chives</a></td> <td><span data-sort-value="7000148000000000000♠" style="display:none"></span> 1.48 </td></tr> <tr> <td><a href="/wiki/Collards" class="mw-redirect" title="Collards">Collards</a></td> <td><span data-sort-value="6999450000000000000♠" style="display:none"></span> 0.45 </td></tr> <tr> <td><a href="/wiki/Coriander" title="Coriander">Coriander</a></td> <td><span data-sort-value="6998100000000000000♠" style="display:none"></span> 0.01 </td></tr> <tr> <td><a href="/wiki/Sweet_corn" title="Sweet corn">Corn, sweet</a></td> <td><span data-sort-value="6998100000000000000♠" style="display:none"></span> 0.01 </td></tr> <tr> <td><a href="/wiki/Cucumber" title="Cucumber">Cucumber</a></td> <td><span data-sort-value="6998200000000000000♠" style="display:none"></span> 0.02 </td></tr> <tr> <td><a href="/wiki/Eggplant" title="Eggplant">Eggplant</a></td> <td><span data-sort-value="6999190000000000000♠" style="display:none"></span> 0.19 </td></tr> <tr> <td><a href="/wiki/Endive" title="Endive">Endive</a></td> <td><span data-sort-value="6999110000000000000♠" style="display:none"></span> 0.11 </td></tr> <tr> <td><a href="/wiki/Garlic" title="Garlic">Garlic</a></td> <td><span data-sort-value="6999360000000000000♠" style="display:none"></span> 0.36 </td></tr> <tr> <td><a href="/wiki/Kale" title="Kale">Kale</a></td> <td><span data-sort-value="6998200000000000000♠" style="display:none"></span> 0.02 </td></tr> <tr> <td><a href="/wiki/Lettuce" title="Lettuce">Lettuce</a></td> <td><span data-sort-value="6999330000000000000♠" style="display:none"></span> 0.33 </td></tr> <tr> <td><a href="/wiki/Okra" title="Okra">Okra</a></td> <td><span data-sort-value="6998500000000000000♠" style="display:none"></span> 0.05 </td></tr> <tr> <td><a href="/wiki/Onion" title="Onion">Onion</a></td> <td><span data-sort-value="6998500000000000000♠" style="display:none"></span> 0.05 </td></tr> <tr> <td><a href="/wiki/Parsley" title="Parsley">Parsley</a></td> <td><span data-sort-value="7000170000000000000♠" style="display:none"></span> 1.70 </td></tr> <tr> <td><a href="/wiki/Parsnip" title="Parsnip">Parsnip</a></td> <td><span data-sort-value="6998400000000000000♠" style="display:none"></span> 0.04 </td></tr> <tr> <td><a href="/wiki/Pea" title="Pea">Pea</a></td> <td><span data-sort-value="6998500000000000000♠" style="display:none"></span> 0.05 </td></tr> <tr> <td><a href="/wiki/Bell_pepper" title="Bell pepper">Bell pepper</a></td> <td><span data-sort-value="6998400000000000000♠" style="display:none"></span> 0.04 </td></tr> <tr> <td><a href="/wiki/Potato" title="Potato">Potato</a></td> <td><span data-sort-value="6998500000000000000♠" style="display:none"></span> 0.05 </td></tr> <tr> <td><a href="/wiki/Portulaca_oleracea" title="Portulaca oleracea">Purslane</a></td> <td><span data-sort-value="7000131000000000000♠" style="display:none"></span> 1.31 </td></tr> <tr> <td><a href="/wiki/Radish" title="Radish">Radish</a></td> <td><span data-sort-value="6999480000000000000♠" style="display:none"></span> 0.48 </td></tr> <tr> <td><a href="/wiki/Rhubarb" title="Rhubarb">Rhubarb</a> leaves</td> <td><span data-sort-value="6999520000000000000♠" style="display:none"></span> 0.52<sup id="cite_ref-63" class="reference"><a href="#cite_note-63"><span class="cite-bracket">[</span>63<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Rutabaga" title="Rutabaga">Rutabaga</a></td> <td><span data-sort-value="6998300000000000000♠" style="display:none"></span> 0.03 </td></tr> <tr> <td><a href="/wiki/Spinach" title="Spinach">Spinach</a></td> <td><span data-sort-value="6999970000000000000♠" style="display:none"></span> 0.97 <small>(ranges from 0.65% to 1.3%<br />on fresh weight basis)</small><sup id="cite_ref-64" class="reference"><a href="#cite_note-64"><span class="cite-bracket">[</span>64<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Squash_(plant)" class="mw-redirect" title="Squash (plant)">Squash</a></td> <td><span data-sort-value="6998200000000000000♠" style="display:none"></span> 0.02 </td></tr> <tr> <td><a href="/wiki/Sweet_potato" title="Sweet potato">Sweet potato</a></td> <td><span data-sort-value="6999240000000000000♠" style="display:none"></span> 0.24 </td></tr> <tr> <td><a href="/wiki/Swiss_chard" class="mw-redirect" title="Swiss chard">Swiss chard</a>, green</td> <td><span data-sort-value="6999960000000000000♠" style="display:none"></span> 0.96 <sup id="cite_ref-ReferenceA_62-2" class="reference"><a href="#cite_note-ReferenceA-62"><span class="cite-bracket">[</span>62<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Tomato" title="Tomato">Tomato</a></td> <td><span data-sort-value="6998500000000000000♠" style="display:none"></span> 0.05 </td></tr> <tr> <td><a href="/wiki/Turnip" title="Turnip">Turnip</a></td> <td><span data-sort-value="6999210000000000000♠" style="display:none"></span> 0.21 </td></tr> <tr> <td><a href="/wiki/Turnip_greens" class="mw-redirect" title="Turnip greens">Turnip greens</a></td> <td><span data-sort-value="6998500000000000000♠" style="display:none"></span> 0.05 </td></tr> <tr> <td><a href="/wiki/Watercress" title="Watercress">Watercress</a></td> <td><span data-sort-value="6999310000000000000♠" style="display:none"></span> 0.31 </td></tr></tbody></table> <div class="mw-heading mw-heading2"><h2 id="Toxicity">Toxicity</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Oxalic_acid&action=edit&section=22" title="Edit section: Toxicity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Oxalic acid has an oral <a href="/wiki/Lowest_published_lethal_dose" class="mw-redirect" title="Lowest published lethal dose">LD<sub>Lo</sub></a> (lowest published lethal dose) of 600 mg/kg.<sup id="cite_ref-65" class="reference"><a href="#cite_note-65"><span class="cite-bracket">[</span>65<span class="cite-bracket">]</span></a></sup> It has been reported that the lethal oral dose is 15 to 30 grams.<sup id="cite_ref-66" class="reference"><a href="#cite_note-66"><span class="cite-bracket">[</span>66<span class="cite-bracket">]</span></a></sup> The toxicity of oxalic acid is due to kidney failure caused by precipitation of solid <a href="/wiki/Calcium_oxalate" title="Calcium oxalate">calcium oxalate</a>.<sup id="cite_ref-67" class="reference"><a href="#cite_note-67"><span class="cite-bracket">[</span>67<span class="cite-bracket">]</span></a></sup> </p><p>Oxalate is known to cause <a href="/wiki/Mitochondrial_dysfunction" class="mw-redirect" title="Mitochondrial dysfunction">mitochondrial dysfunction</a>.<sup id="cite_ref-68" class="reference"><a href="#cite_note-68"><span class="cite-bracket">[</span>68<span class="cite-bracket">]</span></a></sup> </p><p>Ingestion of <a href="/wiki/Ethylene_glycol" title="Ethylene glycol">ethylene glycol</a> results in oxalic acid as a metabolite which can also cause acute kidney failure. </p> <div class="mw-heading mw-heading2"><h2 id="Kidney_stones">Kidney stones</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Oxalic_acid&action=edit&section=23" title="Edit section: Kidney stones"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Most <a href="/wiki/Kidney_stone" class="mw-redirect" title="Kidney stone">kidney stones</a>, 76%, are composed of <a href="/wiki/Calcium_oxalate" title="Calcium oxalate">calcium oxalate</a>.<sup id="cite_ref-Singh_69-0" class="reference"><a href="#cite_note-Singh-69"><span class="cite-bracket">[</span>69<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Notes">Notes</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Oxalic_acid&action=edit&section=24" title="Edit section: Notes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><style data-mw-deduplicate="TemplateStyles:r1041539562">.mw-parser-output .citation{word-wrap:break-word}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}</style><span class="citation wikicite" id="endnote_reference_name_A"><b><a href="#ref_reference_name_A">^a</a></b></span> Unless otherwise cited, all measurements are based on raw vegetable weights with original moisture content. </p> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Oxalic_acid&action=edit&section=25" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist reflist-columns references-column-width" style="column-width: 30em;"> <ol class="references"> <li id="cite_note-iupac2013-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-iupac2013_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-iupac2013_1-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite class="citation book cs1">"Front Matter". <i>Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book)</i>. Cambridge: <a href="/wiki/Royal_Society_of_Chemistry" title="Royal Society of Chemistry">The Royal Society of Chemistry</a>. 2014. pp. <span class="nowrap">P001 –</span> <span class="nowrap">P004</span>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1039%2F9781849733069-FP001">10.1039/9781849733069-FP001</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-85404-182-4" title="Special:BookSources/978-0-85404-182-4"><bdi>978-0-85404-182-4</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Front+Matter&rft.btitle=Nomenclature+of+Organic+Chemistry+%3A+IUPAC+Recommendations+and+Preferred+Names+2013+%28Blue+Book%29&rft.place=Cambridge&rft.pages=%3Cspan+class%3D%22nowrap%22%3EP001+-%3C%2Fspan%3E+%3Cspan+class%3D%22nowrap%22%3EP004%3C%2Fspan%3E&rft.pub=The+Royal+Society+of+Chemistry&rft.date=2014&rft_id=info%3Adoi%2F10.1039%2F9781849733069-FP001&rft.isbn=978-0-85404-182-4&rfr_id=info%3Asid%2Fen.wikipedia.org%3AOxalic+acid" class="Z3988"></span></span> </li> <li id="cite_note-GESTIS-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-GESTIS_2-0">^</a></b></span> <span class="reference-text"><a rel="nofollow" class="external text" href="https://gestis.dguv.de/data?name=017910&lang=en">Record </a> in the <a href="/wiki/GESTIS_Substance_Database" title="GESTIS Substance Database">GESTIS Substance Database</a> of the <a href="/wiki/Institute_for_Occupational_Safety_and_Health_of_the_German_Social_Accident_Insurance" title="Institute for Occupational Safety and Health of the German Social Accident Insurance">Institute for Occupational Safety and Health</a> </span> </li> <li id="cite_note-apel1987-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-apel1987_3-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFApelblatManzurola1987" class="citation journal cs1">Apelblat, Alexander; Manzurola, Emanuel (1987). "Solubility of oxalic, malonic, succinic, adipic, maleic, malic, citric, and tartaric acids in water from 278.15 to 338.15 K". <i>The Journal of Chemical Thermodynamics</i>. <b>19</b> (3): <span class="nowrap">317–</span>320. <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/1987JChTh..19..317A">1987JChTh..19..317A</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%2F0021-9614%2887%2990139-X">10.1016/0021-9614(87)90139-X</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+Chemical+Thermodynamics&rft.atitle=Solubility+of+oxalic%2C+malonic%2C+succinic%2C+adipic%2C+maleic%2C+malic%2C+citric%2C+and+tartaric+acids+in+water+from+278.15+to+338.15+K&rft.volume=19&rft.issue=3&rft.pages=%3Cspan+class%3D%22nowrap%22%3E317-%3C%2Fspan%3E320&rft.date=1987&rft_id=info%3Adoi%2F10.1016%2F0021-9614%2887%2990139-X&rft_id=info%3Abibcode%2F1987JChTh..19..317A&rft.aulast=Apelblat&rft.aufirst=Alexander&rft.au=Manzurola%2C+Emanuel&rfr_id=info%3Asid%2Fen.wikipedia.org%3AOxalic+acid" class="Z3988"></span></span> </li> <li id="cite_note-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-4">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFRadiant_Agro_Chem" class="citation web cs1">Radiant Agro Chem. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20110715144417/http://www.racpl.com/oa_msds.htm">"Oxalic Acid MSDS"</a>. Archived from <a rel="nofollow" class="external text" href="http://www.racpl.com/oa_msds.htm">the original</a> on 2011-07-15<span class="reference-accessdate">. Retrieved <span class="nowrap">2012-02-02</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Oxalic+Acid+MSDS&rft.au=Radiant+Agro+Chem&rft_id=http%3A%2F%2Fwww.racpl.com%2Foa_msds.htm&rfr_id=info%3Asid%2Fen.wikipedia.org%3AOxalic+acid" class="Z3988"></span></span> </li> <li id="cite_note-PGCH-5"><span class="mw-cite-backlink">^ <a href="#cite_ref-PGCH_5-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-PGCH_5-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-PGCH_5-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-PGCH_5-3"><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="CITEREFNIOSH_Pocket_Guide_to_Chemical_Hazards" class="citation web cs1">NIOSH Pocket Guide to Chemical Hazards. <a rel="nofollow" class="external text" href="https://www.cdc.gov/niosh/npg/npgd0474.html">"#0474"</a>. <a href="/wiki/National_Institute_for_Occupational_Safety_and_Health" title="National Institute for Occupational Safety and Health">National Institute for Occupational Safety and Health</a> (NIOSH).</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=%230474&rft.pub=National+Institute+for+Occupational+Safety+and+Health+%28NIOSH%29&rft.au=NIOSH+Pocket+Guide+to+Chemical+Hazards&rft_id=https%3A%2F%2Fwww.cdc.gov%2Fniosh%2Fnpg%2Fnpgd0474.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AOxalic+acid" class="Z3988"></span></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 id="CITEREFBjerrumSillénSchwarzenbachAnderegg1958" class="citation book cs1">Bjerrum, Jannik; Sillén, Lars Gunnar; Schwarzenbach, Gerold Karl; Anderegg, Giorgio (1958). <i>Stability constants of metal-ion complexes, with solubility products of inorganic substances</i>. London: <a href="/wiki/Chemical_Society" title="Chemical Society">Chemical Society</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Stability+constants+of+metal-ion+complexes%2C+with+solubility+products+of+inorganic+substances&rft.place=London&rft.pub=Chemical+Society&rft.date=1958&rft.aulast=Bjerrum&rft.aufirst=Jannik&rft.au=Sill%C3%A9n%2C+Lars+Gunnar&rft.au=Schwarzenbach%2C+Gerold+Karl&rft.au=Anderegg%2C+Giorgio&rfr_id=info%3Asid%2Fen.wikipedia.org%3AOxalic+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 book cs1"><a rel="nofollow" class="external text" href="https://www.worldcat.org/oclc/930681942"><i>CRC handbook of chemistry and physics : a ready-reference book of chemical and physical data</i></a>. William M. Haynes, David R. Lide, Thomas J. Bruno (2016-2017, 97th ed.). Boca Raton, Florida. 2016. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4987-5428-6" title="Special:BookSources/978-1-4987-5428-6"><bdi>978-1-4987-5428-6</bdi></a>. <a href="/wiki/OCLC_(identifier)" class="mw-redirect" title="OCLC (identifier)">OCLC</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/oclc/930681942">930681942</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=CRC+handbook+of+chemistry+and+physics+%3A+a+ready-reference+book+of+chemical+and+physical+data.&rft.place=Boca+Raton%2C+Florida&rft.edition=2016-2017%2C+97th&rft.date=2016&rft_id=info%3Aoclcnum%2F930681942&rft.isbn=978-1-4987-5428-6&rft_id=https%3A%2F%2Fwww.worldcat.org%2Foclc%2F930681942&rfr_id=info%3Asid%2Fen.wikipedia.org%3AOxalic+acid" class="Z3988"></span><span class="cs1-maint citation-comment"><code class="cs1-code">{{<a href="/wiki/Template:Cite_book" title="Template:Cite book">cite book</a>}}</code>: CS1 maint: location missing publisher (<a href="/wiki/Category:CS1_maint:_location_missing_publisher" title="Category:CS1 maint: location missing publisher">link</a>) CS1 maint: others (<a href="/wiki/Category:CS1_maint:_others" title="Category:CS1 maint: others">link</a>)</span></span> </li> <li id="cite_note-8"><span class="mw-cite-backlink"><b><a href="#cite_ref-8">^</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.cdc.gov/niosh/idlh/144627.html">"Oxalic acid"</a>. <i>Immediately Dangerous to Life or Health Concentrations (IDLH)</i>. <a href="/wiki/National_Institute_for_Occupational_Safety_and_Health" title="National Institute for Occupational Safety and Health">National Institute for Occupational Safety and Health</a> (NIOSH).</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Immediately+Dangerous+to+Life+or+Health+Concentrations+%28IDLH%29&rft.atitle=Oxalic+acid&rft_id=https%3A%2F%2Fwww.cdc.gov%2Fniosh%2Fidlh%2F144627.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AOxalic+acid" class="Z3988"></span></span> </li> <li id="cite_note-Oxalic_Acid:_Uses-9"><span class="mw-cite-backlink"><b><a href="#cite_ref-Oxalic_Acid:_Uses_9-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation book cs1"><i>Ullmann's Encyclopedia of Industrial Chemistry</i>. Wiley. 2005. pp. 17624/28029. <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">10.1002/14356007</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9783527306732" title="Special:BookSources/9783527306732"><bdi>9783527306732</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Ullmann%27s+Encyclopedia+of+Industrial+Chemistry&rft.pages=17624%2F28029&rft.pub=Wiley&rft.date=2005&rft_id=info%3Adoi%2F10.1002%2F14356007&rft.isbn=9783527306732&rfr_id=info%3Asid%2Fen.wikipedia.org%3AOxalic+acid" class="Z3988"></span></span> </li> <li id="cite_note-10"><span class="mw-cite-backlink"><b><a href="#cite_ref-10">^</a></b></span> <span class="reference-text">See: <ul><li>Herman Boerhaave, <i>Elementa Chemiae</i> (Basil, Switzerland: Johann Rudolph Im-hoff, 1745), volume 2, <a rel="nofollow" class="external text" href="https://books.google.com/books?id=_gVAAAAAcAAJ&pg=PA35">pp. 35-38.</a> (in Latin) From p. 35: <i>"Processus VII. Sal nativum plantarum paratus de succo illarum recens presso. Hic Acetosae."</i> (Procedure 7. A natural salt of plants prepared from their freshly pressed juice. This [salt obtained] from sorrel.)</li> <li>Henry Enfield Roscoe and Carl Schorlemmer, ed.s, <i>A Treatise on Chemistry</i> (New York, New York: D. Appleton and Co., 1890), volume 3, part 2, <a rel="nofollow" class="external text" href="https://books.google.com/books?id=xM4cAQAAIAAJ&pg=PA105">p. 105.</a></li> <li>See also Wikipedia's articles "<a href="/wiki/Oxalis_acetosella" title="Oxalis acetosella">Oxalis acetosella</a>" and "<a href="/wiki/Potassium_hydrogenoxalate" title="Potassium hydrogenoxalate">Potassium hydrogen oxalate</a>".</li></ul> </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">See: <ul><li>François Pierre Savary, <a rel="nofollow" class="external text" href="https://books.google.com/books?id=a7JTAAAAcAAJ&pg=PA1"><i>Dissertatio Inauguralis De Sale Essentiali Acetosellæ</i></a> [Inaugural dissertation on the essential salt of wood sorrel] (Jean François Le Roux, 1773). (in Latin) Savary noticed that when he distilled sorrel salt (potassium hydrogen oxalate), crystals would sublimate onto the receiver. From p. 17: <i>"Unum adhuc circa liquorem acidum, quem sal acetosellae tam sincerissimum a nobis paratum quam venale destillatione fundit phoenomenon erit notandum, nimirum quod aliquid ejus sub forma sicca crystallina lateribus excipuli accrescat, ..."</i> (One more [thing] will be noted regarding the acid liquid, which furnished for us sorrel salt as pure as commercial distillations, [it] produces a phenomenon, that evidently something in dry, crystalline form grows on the sides of the receiver, ...) These were crystals of oxalic acid.</li> <li>Leopold Gmelin with Henry Watts, trans., <i>Hand-book of Chemistry</i> (London, England: Cavendish Society, 1855), volume 9, <a rel="nofollow" class="external text" href="https://archive.org/details/handbookchemist09wattgoog/page/n139">p. 111.</a></li></ul> </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">See: <ul><li>Torbern Bergman with Johan Afzelius (1776) <i>Dissertatio chemica de acido sacchari</i> [Chemical dissertation on sugar acid] (Uppsala, Sweden: Edman, 1776).</li> <li>Torbern Bergman, <i>Opuscula Physica et Chemica</i>, (Leipzig (Lipsia), (Germany): I.G. Müller, 1776), volume 1, <a rel="nofollow" class="external text" href="https://books.google.com/books?id=HcuNbkfxYQMC&pg=PA238">"VIII. De acido Sacchari," pp. 238–263.</a></li></ul> </span></li> <li id="cite_note-13"><span class="mw-cite-backlink"><b><a href="#cite_ref-13">^</a></b></span> <span class="reference-text">Carl Wilhelm Scheele (1784) <a rel="nofollow" class="external text" href="http://babel.hathitrust.org/cgi/pt?id=mdp.39015009215438;view=1up;seq=194">"Om Rhabarber-jordens bestånds-delar, samt sått at tilreda Acetosell-syran"</a> (On rhubarb-earth's constituents, as well as ways of preparing sorrel-acid), <i>Kungliga Vetenskapsakademiens Nya Handlingar</i> [New Proceedings of the Royal Academy of Science], 2nd series, <b>5</b> : 183-187. (in Swedish) From p. 187: <i>"Således finnes just samma syra som vi genom konst af socker med tilhjelp af salpeter-syra tilreda, redan förut af naturen tilredd uti o̊rten Acetosella."</i> (Thus it is concluded [that] the very same acid as we prepare artificially by means of sugar with the help of nitric acid, [was] previously prepared naturally in the herb <i>acetosella</i> [i.e., sorrel].)</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 class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.cnrtl.fr/definition/oxalique">"OXALIQUE : Définition de OXALIQUE"</a>. <i>www.cnrtl.fr</i><span class="reference-accessdate">. Retrieved <span class="nowrap">2024-09-27</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=www.cnrtl.fr&rft.atitle=OXALIQUE+%3A+D%C3%A9finition+de+OXALIQUE&rft_id=https%3A%2F%2Fwww.cnrtl.fr%2Fdefinition%2Foxalique&rfr_id=info%3Asid%2Fen.wikipedia.org%3AOxalic+acid" class="Z3988"></span></span> </li> <li id="cite_note-15"><span class="mw-cite-backlink"><b><a href="#cite_ref-15">^</a></b></span> <span class="reference-text">See: <ul><li>F. Wöhler (1824) <a rel="nofollow" class="external text" href="http://babel.hathitrust.org/cgi/pt?id=mdp.39015039477917;view=1up;seq=332">"Om några föreningar af Cyan"</a> (On some compounds of cyanide), <i>Kungliga Vetenskapsakademiens Handlingar</i> [Proceedings of the Royal Academy of Science], pp. 328–333. (in Swedish)</li> <li>Reprinted in German as: F. Wöhler (1825) <a rel="nofollow" class="external text" href="http://babel.hathitrust.org/cgi/pt?id=umn.31951d003167111;view=1up;seq=195">"Ueber Cyan-Verbindungen"</a> (On cyanide compounds), <i>Annalen der Physik und Chemie</i>, 2nd series, <b>3</b> : 177-182.</li></ul> </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></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFRiemenschneiderTanifuji2000" class="citation book cs1">Riemenschneider, Wilhelm; Tanifuji, Minoru (2000). 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title="wikisource:1911 Encyclopædia Britannica/Oxalic Acid">Oxalic Acid</a></span>".</div></div> </div> <ul><li><a rel="nofollow" class="external text" href="http://gmd.mpimp-golm.mpg.de/Spectrums/ad304d2f-132a-4bba-8e72-d931e77e1c6e.aspx">Oxalic acid MS Spectrum</a></li> <li><a rel="nofollow" class="external text" href="https://www.ilo.org/dyn/icsc/showcard.display?p_lang=en&p_card_id=0529&p_version=2">International Chemical Safety Card 0529</a></li> <li><a rel="nofollow" class="external text" href="https://www.cdc.gov/niosh/npg/npgd0474.html">NIOSH Guide to Chemical Hazards (CDC)</a></li> <li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20051024031722/http://www.nal.usda.gov/fnic/foodcomp/Data/Other/oxalic.html">Table: Oxalic acid content of selected vegetables (USDA)</a></li> <li><a rel="nofollow" class="external text" href="https://www.ars.usda.gov/Services/docs.htm?docid=9444">Alternative link: Table: Oxalic Acid Content of Selected Vegetables (USDA)</a></li> <li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20081016043139/http://www.rhubarbinfo.com/rhubarb-poison.html">About rhubarb poisoning (The Rhubarb Compendium)</a></li> <li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20110902070929/http://www.ohf.org/docs/Oxalate2008.pdf">Oxalosis & Hyperoxaluria Foundation (OHF) The Oxalate Content of Food 2008 (PDF)</a></li> <li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20110902020938/http://www.ohf.org/diet.html">Oxalosis & Hyperoxaluria Foundation (OHF) Diet Information</a></li> <li><a rel="nofollow" class="external text" href="http://www.aim.env.uea.ac.uk/aim/accent2/inputpage.php">Calculator: Water and solute activities in aqueous oxalic acid</a></li></ul> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist 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href="/wiki/Dicarboxylic_acid#Linear_saturated_dicarboxylic_acids" title="Dicarboxylic acid">Linear saturated dicarboxylic acids</a> (HO<sub>2</sub>C-R-CO<sub>2</sub>H)</div></th></tr><tr><td colspan="2" class="navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"><div class="hlist"><ul><li><a class="mw-selflink selflink">Ethanedioic acid</a> (Oxalic acid) (CO<sub>2</sub>H)</li><li><a href="/wiki/Malonic_acid" title="Malonic acid">Propanedioic acid</a> (Malonic acid) CH<sub>2</sub>(CO<sub>2</sub>H)</li><li><a href="/wiki/Succinic_acid" title="Succinic acid">Butanedioic acid</a> (Succinic acid) C<sub>2</sub>H<sub>4</sub>(CO<sub>2</sub>H)</li><li><a href="/wiki/Glutaric_acid" title="Glutaric acid">Pentanedioic acid</a> (Glutaric acid) C<sub>3</sub>H<sub>6</sub>(CO<sub>2</sub>H)</li><li><a href="/wiki/Adipic_acid" title="Adipic acid">Hexanedioic acid</a> (Adipic acid) C<sub>4</sub>H<sub>8</sub>(CO<sub>2</sub>H)</li><li><a href="/wiki/Pimelic_acid" title="Pimelic acid">Heptanedioic acid</a> (Pimelic acid) C<sub>7</sub>H<sub>12</sub>O<sub>4</sub></li><li><a href="/wiki/Suberic_acid" title="Suberic acid">Octanedioic acid</a> (Suberic acid) C<sub>8</sub>H<sub>14</sub>O<sub>4</sub></li><li><a href="/wiki/Azelaic_acid" title="Azelaic acid">Nonanedioic acid</a> (Azelaic acid) C<sub>9</sub>H<sub>16</sub>O<sub>4</sub></li><li><a href="/wiki/Sebacic_acid" title="Sebacic acid">Decanedioic acid</a> (Sebacic acid) C<sub>10</sub>H<sub>18</sub>O<sub>4</sub></li><li><a href="/wiki/Dodecanedioic_acid" title="Dodecanedioic acid">Dodecanedioic acid</a> C<sub>12</sub>H<sub>22</sub>O<sub>4</sub></li><li><a href="/wiki/Brassylic_acid" title="Brassylic acid">Tredecanedioic acid</a> (Brassylic acid) C<sub>13</sub>H<sub>24</sub>O<sub>4</sub></li><li><a href="/wiki/Thapsic_acid" title="Thapsic acid">Hexadecanedioic acid</a> (Thapsic acid) C<sub>16</sub>H<sub>30</sub>O<sub>4</sub></li><li><a href="/wiki/Docosanedioic_acid" title="Docosanedioic 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