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<a class="vector-toc-link" href="#Metabolism_and_exercise"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.2</span> <span>Metabolism and exercise</span> </div> </a> <ul id="toc-Metabolism_and_exercise-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Neural_tissue_energy_source" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Neural_tissue_energy_source"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.3</span> <span>Neural tissue energy source</span> </div> </a> <ul id="toc-Neural_tissue_energy_source-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Brain_development_metabolism" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Brain_development_metabolism"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.4</span> <span>Brain development metabolism</span> </div> </a> <ul id="toc-Brain_development_metabolism-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Blood_testing" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Blood_testing"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Blood testing</span> </div> </a> <ul id="toc-Blood_testing-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Uses" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Uses"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Uses</span> </div> </a> <button aria-controls="toc-Uses-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Uses subsection</span> </button> <ul id="toc-Uses-sublist" class="vector-toc-list"> <li id="toc-Polymer_precursor" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Polymer_precursor"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1</span> <span>Polymer precursor</span> </div> </a> <ul id="toc-Polymer_precursor-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Pharmaceutical_and_cosmetic_applications" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Pharmaceutical_and_cosmetic_applications"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.2</span> <span>Pharmaceutical and cosmetic applications</span> </div> </a> <ul id="toc-Pharmaceutical_and_cosmetic_applications-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Foods" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Foods"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.3</span> <span>Foods</span> </div> </a> <ul id="toc-Foods-sublist" class="vector-toc-list"> <li id="toc-Fermented_food" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Fermented_food"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.3.1</span> <span>Fermented food</span> </div> </a> <ul id="toc-Fermented_food-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Separately_added" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Separately_added"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.3.2</span> <span>Separately added</span> </div> </a> <ul id="toc-Separately_added-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Forgery" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Forgery"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.4</span> <span>Forgery</span> </div> </a> <ul id="toc-Forgery-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Cleaning_products" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Cleaning_products"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.5</span> <span>Cleaning products</span> </div> </a> <ul id="toc-Cleaning_products-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>See also</span> </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</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">8</span> <span>External links</span> </div> </a> <ul id="toc-External_links-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span class="vector-dropdown-label-text">Toggle the table of contents</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Lactic 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 71 languages" > <label id="p-lang-btn-label" for="p-lang-btn-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--action-progressive mw-portlet-lang-heading-71" aria-hidden="true" ><span class="vector-icon mw-ui-icon-language-progressive mw-ui-icon-wikimedia-language-progressive"></span> <span class="vector-dropdown-label-text">71 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%AD%D9%85%D8%B6_%D8%A7%D9%84%D9%84%D8%A8%D9%86%D9%8A%D9%83" title="حمض اللبنيك – Arabic" lang="ar" hreflang="ar" data-title="حمض اللبنيك" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-ast mw-list-item"><a href="https://ast.wikipedia.org/wiki/%C3%81cidu_l%C3%A1ctico" title="Ácidu láctico – Asturian" lang="ast" hreflang="ast" data-title="Ácidu láctico" data-language-autonym="Asturianu" data-language-local-name="Asturian" class="interlanguage-link-target"><span>Asturianu</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D8%A7%D8%B3%DB%8C%D8%AF_%D9%84%D8%A7%DA%A9%D8%AA%DB%8C%DA%A9" title="اسید لاکتیک – South Azerbaijani" lang="azb" hreflang="azb" data-title="اسید لاکتیک" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-be mw-list-item"><a href="https://be.wikipedia.org/wiki/%D0%9C%D0%B0%D0%BB%D0%BE%D1%87%D0%BD%D0%B0%D1%8F_%D0%BA%D1%96%D1%81%D0%BB%D0%B0%D1%82%D0%B0" title="Малочная кіслата – Belarusian" lang="be" hreflang="be" data-title="Малочная 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%9C%D0%B0%D0%BB%D0%BE%D1%87%D0%BD%D0%B0%D1%8F_%D0%BA%D1%96%D1%81%D1%8C%D0%BB%D1%8F" title="Малочная кісьля – Belarusian (Taraškievica orthography)" lang="be-tarask" hreflang="be-tarask" data-title="Малочная 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%9C%D0%BB%D0%B5%D1%87%D0%BD%D0%B0_%D0%BA%D0%B8%D1%81%D0%B5%D0%BB%D0%B8%D0%BD%D0%B0" title="Млечна киселина – Bulgarian" lang="bg" hreflang="bg" data-title="Млечна киселина" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target"><span>Български</span></a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Mlije%C4%8Dna_kiselina" title="Mliječna kiselina – Bosnian" lang="bs" hreflang="bs" data-title="Mliječna kiselina" data-language-autonym="Bosanski" data-language-local-name="Bosnian" class="interlanguage-link-target"><span>Bosanski</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/%C3%80cid_l%C3%A0ctic" title="Àcid làctic – Catalan" lang="ca" hreflang="ca" data-title="Àcid làctic" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-cv mw-list-item"><a href="https://cv.wikipedia.org/wiki/%D0%A1%C4%95%D1%82_%D0%B9%D3%B3%C3%A7%D0%B5%D0%BA%C4%95" title="Сĕт йӳçекĕ – Chuvash" lang="cv" hreflang="cv" data-title="Сĕт йӳçекĕ" data-language-autonym="Чӑвашла" data-language-local-name="Chuvash" class="interlanguage-link-target"><span>Чӑвашла</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Kyselina_ml%C3%A9%C4%8Dn%C3%A1" title="Kyselina mléčná – Czech" lang="cs" hreflang="cs" data-title="Kyselina mléčná" 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_lactig" title="Asid lactig – Welsh" lang="cy" hreflang="cy" data-title="Asid lactig" 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/M%C3%A6lkesyre" title="Mælkesyre – Danish" lang="da" hreflang="da" data-title="Mælkesyre" 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/Milchs%C3%A4ure" title="Milchsäure – German" lang="de" hreflang="de" data-title="Milchsäure" 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/Piimhape" title="Piimhape – Estonian" lang="et" hreflang="et" data-title="Piimhape" 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%93%CE%B1%CE%BB%CE%B1%CE%BA%CF%84%CE%B9%CE%BA%CF%8C_%CE%BF%CE%BE%CF%8D" title="Γαλακτικό οξύ – Greek" lang="el" hreflang="el" data-title="Γαλακτικό 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_l%C3%A1ctico" title="Ácido láctico – Spanish" lang="es" hreflang="es" data-title="Ácido láctico" 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/Laktata_acido" title="Laktata acido – Esperanto" lang="eo" hreflang="eo" data-title="Laktata 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_laktiko" title="Azido laktiko – Basque" lang="eu" hreflang="eu" data-title="Azido laktiko" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%A7%D8%B3%DB%8C%D8%AF_%D9%84%D8%A7%DA%A9%D8%AA%DB%8C%DA%A9" title="اسید لاکتیک – Persian" lang="fa" hreflang="fa" data-title="اسید لاکتیک" 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_lactique" title="Acide lactique – French" lang="fr" hreflang="fr" data-title="Acide lactique" 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_lachtach" title="Aigéad lachtach – Irish" lang="ga" hreflang="ga" data-title="Aigéad lachtach" 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_l%C3%A1ctico" title="Ácido láctico – Galician" lang="gl" hreflang="gl" data-title="Ácido láctico" 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/%EB%9D%BD%ED%8A%B8%EC%82%B0" title="락트산 – Korean" lang="ko" hreflang="ko" data-title="락트산" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D4%BF%D5%A1%D5%A9%D5%B6%D5%A1%D5%A9%D5%A9%D5%B8%D6%82" title="Կաթնաթթու – Armenian" lang="hy" hreflang="hy" data-title="Կաթնաթթու" 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%B2%E0%A5%88%E0%A4%95%E0%A5%8D%E0%A4%9F%E0%A4%BF%E0%A4%95_%E0%A4%85%E0%A4%AE%E0%A5%8D%E0%A4%B2" title="लैक्टिक अम्ल – Hindi" lang="hi" hreflang="hi" data-title="लैक्टिक 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/Mlije%C4%8Dna_kiselina" title="Mliječna kiselina – Croatian" lang="hr" hreflang="hr" data-title="Mliječna 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_laktat" title="Asam laktat – Indonesian" lang="id" hreflang="id" data-title="Asam laktat" 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/Mj%C3%B3lkurs%C3%BDra" title="Mjólkursýra – Icelandic" lang="is" hreflang="is" data-title="Mjólkursýra" 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_lattico" title="Acido lattico – Italian" lang="it" hreflang="it" data-title="Acido lattico" 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%9C%D7%A7%D7%98%D7%99%D7%AA" title="חומצה לקטית – Hebrew" lang="he" hreflang="he" data-title="חומצה לקטית" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-jv mw-list-item"><a href="https://jv.wikipedia.org/wiki/Asem_laktat" title="Asem laktat – Javanese" lang="jv" hreflang="jv" data-title="Asem laktat" data-language-autonym="Jawa" data-language-local-name="Javanese" class="interlanguage-link-target"><span>Jawa</span></a></li><li class="interlanguage-link interwiki-ka mw-list-item"><a href="https://ka.wikipedia.org/wiki/%E1%83%A0%E1%83%AB%E1%83%94%E1%83%9B%E1%83%9F%E1%83%90%E1%83%95%E1%83%90" title="რძემჟავა – Georgian" lang="ka" hreflang="ka" data-title="რძემჟავა" data-language-autonym="ქართული" data-language-local-name="Georgian" class="interlanguage-link-target"><span>ქართული</span></a></li><li class="interlanguage-link interwiki-kk mw-list-item"><a href="https://kk.wikipedia.org/wiki/%D0%A1%D2%AF%D1%82_%D2%9B%D1%8B%D1%88%D2%9B%D1%8B%D0%BB%D1%8B" title="Сүт қышқылы – Kazakh" lang="kk" hreflang="kk" data-title="Сүт қышқылы" data-language-autonym="Қазақша" data-language-local-name="Kazakh" class="interlanguage-link-target"><span>Қазақша</span></a></li><li class="interlanguage-link interwiki-ht mw-list-item"><a href="https://ht.wikipedia.org/wiki/Asid_laktik" title="Asid laktik – Haitian Creole" lang="ht" hreflang="ht" data-title="Asid laktik" data-language-autonym="Kreyòl ayisyen" data-language-local-name="Haitian Creole" class="interlanguage-link-target"><span>Kreyòl ayisyen</span></a></li><li class="interlanguage-link interwiki-la mw-list-item"><a href="https://la.wikipedia.org/wiki/Acidum_lacticum" title="Acidum lacticum – Latin" lang="la" hreflang="la" data-title="Acidum lacticum" 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/Piensk%C4%81be" title="Pienskābe – Latvian" lang="lv" hreflang="lv" data-title="Pienskābe" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target"><span>Latviešu</span></a></li><li class="interlanguage-link interwiki-lb mw-list-item"><a href="https://lb.wikipedia.org/wiki/M%C3%ABllechsaier" title="Mëllechsaier – Luxembourgish" lang="lb" hreflang="lb" data-title="Mëllechsaier" data-language-autonym="Lëtzebuergesch" data-language-local-name="Luxembourgish" class="interlanguage-link-target"><span>Lëtzebuergesch</span></a></li><li class="interlanguage-link interwiki-lt mw-list-item"><a href="https://lt.wikipedia.org/wiki/Pieno_r%C5%ABg%C5%A1tis" title="Pieno rūgštis – Lithuanian" lang="lt" hreflang="lt" data-title="Pieno 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/Tejsav" title="Tejsav – Hungarian" lang="hu" hreflang="hu" data-title="Tejsav" 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%9C%D0%BB%D0%B5%D1%87%D0%BD%D0%B0_%D0%BA%D0%B8%D1%81%D0%B5%D0%BB%D0%B8%D0%BD%D0%B0" title="Млечна киселина – Macedonian" lang="mk" hreflang="mk" data-title="Млечна 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%B2%E0%B4%BE%E0%B4%95%E0%B5%8D%E0%B4%B1%E0%B5%8D%E0%B4%B1%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="ലാക്റ്റിക് ആസിഡ് – Malayalam" lang="ml" hreflang="ml" data-title="ലാക്റ്റിക് 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_laktik" title="Asid laktik – Malay" lang="ms" hreflang="ms" data-title="Asid laktik" 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/Melkzuur" title="Melkzuur – Dutch" lang="nl" hreflang="nl" data-title="Melkzuur" 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/%E4%B9%B3%E9%85%B8" title="乳酸 – Japanese" lang="ja" hreflang="ja" data-title="乳酸" 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/Melkesyre" title="Melkesyre – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Melkesyre" 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/Mj%C3%B8lkesyre" title="Mjølkesyre – Norwegian Nynorsk" lang="nn" hreflang="nn" data-title="Mjølkesyre" 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/Sut_kislota" title="Sut kislota – Uzbek" lang="uz" hreflang="uz" data-title="Sut 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_mlekowy" title="Kwas mlekowy – Polish" lang="pl" hreflang="pl" data-title="Kwas mlekowy" 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_l%C3%A1ctico" title="Ácido láctico – Portuguese" lang="pt" hreflang="pt" data-title="Ácido láctico" 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_lactic" title="Acid lactic – Romanian" lang="ro" hreflang="ro" data-title="Acid lactic" 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%9C%D0%BE%D0%BB%D0%BE%D1%87%D0%BD%D0%B0%D1%8F_%D0%BA%D0%B8%D1%81%D0%BB%D0%BE%D1%82%D0%B0" title="Молочная кислота – Russian" lang="ru" hreflang="ru" data-title="Молочная кислота" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sq mw-list-item"><a href="https://sq.wikipedia.org/wiki/Acidi_Laktik" title="Acidi Laktik – Albanian" lang="sq" hreflang="sq" data-title="Acidi Laktik" data-language-autonym="Shqip" data-language-local-name="Albanian" class="interlanguage-link-target"><span>Shqip</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Lactic_acid" title="Lactic acid – Simple English" lang="en-simple" hreflang="en-simple" data-title="Lactic 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_mlie%C4%8Dna" title="Kyselina mliečna – Slovak" lang="sk" hreflang="sk" data-title="Kyselina mliečna" 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/Mle%C4%8Dna_kislina" title="Mlečna kislina – Slovenian" lang="sl" hreflang="sl" data-title="Mlečna 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/%D0%9C%D0%BB%D0%B5%D1%87%D0%BD%D0%B0_%D0%BA%D0%B8%D1%81%D0%B5%D0%BB%D0%B8%D0%BD%D0%B0" title="Млечна киселина – Serbian" lang="sr" hreflang="sr" data-title="Млечна киселина" 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/Mlije%C4%8Dna_kiselina" title="Mliječna kiselina – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Mliječna 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-su mw-list-item"><a href="https://su.wikipedia.org/wiki/Asam_laktat" title="Asam laktat – Sundanese" lang="su" hreflang="su" data-title="Asam laktat" data-language-autonym="Sunda" data-language-local-name="Sundanese" class="interlanguage-link-target"><span>Sunda</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Maitohappo" title="Maitohappo – Finnish" lang="fi" hreflang="fi" data-title="Maitohappo" 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/Mj%C3%B6lksyra" title="Mjölksyra – Swedish" lang="sv" hreflang="sv" data-title="Mjölksyra" 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%B2%E0%AE%BE%E0%AE%95%E0%AF%8D%E0%AE%9F%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="லாக்டிக் அமிலம் – Tamil" lang="ta" hreflang="ta" data-title="லாக்டிக் 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%B2%E0%B0%BE%E0%B0%95%E0%B1%8D%E0%B0%9F%E0%B0%BF%E0%B0%95%E0%B0%BE%E0%B0%AE%E0%B1%8D%E0%B0%B2%E0%B0%82" title="లాక్టికామ్లం – Telugu" lang="te" hreflang="te" data-title="లాక్టికామ్లం" 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%B9%81%E0%B8%A5%E0%B9%87%E0%B8%81%E0%B8%95%E0%B8%B4%E0%B8%81" title="กรดแล็กติก – Thai" lang="th" hreflang="th" data-title="กรดแล็กติก" 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/Laktik_asit" title="Laktik asit – Turkish" lang="tr" hreflang="tr" data-title="Laktik 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%9C%D0%BE%D0%BB%D0%BE%D1%87%D0%BD%D0%B0_%D0%BA%D0%B8%D1%81%D0%BB%D0%BE%D1%82%D0%B0" title="Молочна кислота – Ukrainian" lang="uk" hreflang="uk" data-title="Молочна кислота" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-ur mw-list-item"><a href="https://ur.wikipedia.org/wiki/%D9%84%DB%8C%DA%A9%D9%B9%DA%A9_%D8%A7%DB%8C%D8%B3%DA%88" title="لیکٹک ایسڈ – Urdu" lang="ur" hreflang="ur" data-title="لیکٹک ایسڈ" data-language-autonym="اردو" data-language-local-name="Urdu" class="interlanguage-link-target"><span>اردو</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Acid_lactic" title="Acid lactic – Vietnamese" lang="vi" hreflang="vi" data-title="Acid lactic" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target"><span>Tiếng Việt</span></a></li><li class="interlanguage-link interwiki-war mw-list-item"><a href="https://war.wikipedia.org/wiki/Aksido_Lactico" title="Aksido Lactico – Waray" lang="war" hreflang="war" data-title="Aksido Lactico" data-language-autonym="Winaray" data-language-local-name="Waray" class="interlanguage-link-target"><span>Winaray</span></a></li><li class="interlanguage-link interwiki-wuu mw-list-item"><a href="https://wuu.wikipedia.org/wiki/%E4%B9%B3%E9%85%B8" title="乳酸 – Wu" lang="wuu" hreflang="wuu" data-title="乳酸" 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/%E4%B9%B3%E9%85%B8" title="乳酸 – Cantonese" lang="yue" hreflang="yue" data-title="乳酸" 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/%E4%B9%B3%E9%85%B8" title="乳酸 – Chinese" lang="zh" hreflang="zh" data-title="乳酸" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target"><span>中文</span></a></li> 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vector-pinnable-header-pinned" data-feature-name="appearance-pinned" data-pinnable-element-id="vector-appearance" data-pinned-container-id="vector-appearance-pinned-container" data-unpinned-container-id="vector-appearance-unpinned-container" > <div class="vector-pinnable-header-label">Appearance</div> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-appearance.pin">move to sidebar</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-appearance.unpin">hide</button> </div> </div> </div> </nav> </div> </div> <div id="bodyContent" class="vector-body" aria-labelledby="firstHeading" data-mw-ve-target-container> <div class="vector-body-before-content"> <div class="mw-indicators"> </div> <div id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Organic acid</div> <p> <style data-mw-deduplicate="TemplateStyles:r1084375498">.mw-parser-output .ib-chembox{border-collapse:collapse;text-align:left}.mw-parser-output .ib-chembox td,.mw-parser-output .ib-chembox th{border:1px solid #a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}</style> </p> <table class="infobox ib-chembox"> <caption>Lactic acid </caption> <tbody><tr> <td colspan="2" class="borderless" style="text-align:center"> <table border="0" style="width:100%;display:inline-table;"> <tbody><tr> <td style="border-right:1px solid #aaa; width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Lactic-acid-skeletal.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d3/Lactic-acid-skeletal.svg/130px-Lactic-acid-skeletal.svg.png" decoding="async" width="130" height="119" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d3/Lactic-acid-skeletal.svg/195px-Lactic-acid-skeletal.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d3/Lactic-acid-skeletal.svg/260px-Lactic-acid-skeletal.svg.png 2x" data-file-width="128" data-file-height="117" /></a><figcaption></figcaption></figure> </td> <td style="width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Lactic-acid-from-xtal-3D-bs-17.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/47/Lactic-acid-from-xtal-3D-bs-17.png/130px-Lactic-acid-from-xtal-3D-bs-17.png" decoding="async" width="130" height="118" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/47/Lactic-acid-from-xtal-3D-bs-17.png/195px-Lactic-acid-from-xtal-3D-bs-17.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/47/Lactic-acid-from-xtal-3D-bs-17.png/260px-Lactic-acid-from-xtal-3D-bs-17.png 2x" data-file-width="2559" data-file-height="2316" /></a><figcaption></figcaption></figure> </td></tr></tbody></table> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Preferred_IUPAC_name" title="Preferred IUPAC name">Preferred IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;">2-Hydroxypropanoic 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;"><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>Lactic 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></li><li>Milk acid</li></ul></div></div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=50-21-5">50-21-5</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="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=79-33-4">79-33-4</a></span> (<span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">L</span></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="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=10326-41-7">10326-41-7</a></span> (<span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">D</span></span>)<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=CC%28O%29C%28%3DO%29O">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td>3DMet </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.3dmet.dna.affrc.go.jp"><a rel="nofollow" class="external text" href="http://www.3dmet.dna.affrc.go.jp/cgi/show_data.php?acc=B01180">B01180</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>1720251 </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=422">CHEBI:422</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembldb/index.php/compound/inspect/ChEMBL330546">ChEMBL330546</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.96860.html">96860</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a> </td> <td><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.000.017">100.000.017</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q161249#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span> </td></tr> <tr> <td><a href="/wiki/European_Community_number" title="European Community number"><span title="European Community number (chemical identifier)">EC Number</span></a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>200-018-0</li></ul></div> </td></tr> <tr> <td><a href="/wiki/E_number" title="E number"><span title="E number (food additive code)">E number</span></a> </td> <td>E270 <a href="/wiki/E_number#E200–E299" title="E number">(preservatives)</a> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Gmelin_database" title="Gmelin database">Gmelin Reference</a></div> </td> <td>362717 </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/IUPHAR/BPS" class="mw-redirect" title="IUPHAR/BPS">IUPHAR/BPS</a></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.guidetopharmacology.org"><a rel="nofollow" class="external text" href="http://www.guidetopharmacology.org/GRAC/LigandDisplayForward?tab=summary&ligandId=2932">2932</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/KEGG" title="KEGG">KEGG</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.kegg.jp"><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/D00111">D00111</a></span></li><li><span title="www.kegg.jp"><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/C00186">C00186</a></span></li><li><span title="www.kegg.jp"><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/C00256">C00256</a></span></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/612">612</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>OD2800000</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/3B8D35Y7S4">3B8D35Y7S4</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/F9S9FFU82N">F9S9FFU82N</a></span> (<span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">L</span></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/3Q6M5SET7W">3Q6M5SET7W</a></span> (<span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">D</span></span>)<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/UN_number" title="UN number">UN number</a> </td> <td>3265 </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/DTXSID7023192">DTXSID7023192</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q161249#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></span></li></ul></div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/C3H6O3/c1-2(4)3(5)6/h2,4H,1H3,(H,5,6)/t2-/m0/s1<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: JVTAAEKCZFNVCJ-REOHCLBHSA-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; background:transparent;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">CC(O)C(=O)O</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td><span title="Carbon">C</span><sub>3</sub><span title="Hydrogen">H</span><sub>6</sub><span title="Oxygen">O</span><sub>3</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="7001900780000000000♠"></span>90.078</span> g·mol<sup>−1</sup>   </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>18 °C (64 °F; 291 K) </td></tr> <tr> <td><a href="/wiki/Boiling_point" title="Boiling point">Boiling point</a> </td> <td>122 °C (252 °F; 395 K) at 15<span class="nowrap"> </span>mmHg </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>Miscible<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> </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>3.86,<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> 15.1<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> <th colspan="2" style="background: #f8eaba; text-align: center;">Thermochemistry </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Standard_enthalpy_change_of_combustion" class="mw-redirect" title="Standard enthalpy change of combustion">Std enthalpy of<br />combustion</a> <span style="font-size:112%;">(Δ<sub>c</sub><i>H</i><sup>⦵</sup><sub>298</sub>)</span></div> </td> <td>1361.9<span class="nowrap"> </span>kJ/mol, 325.5<span class="nowrap"> </span>kcal/mol, 15.1<span class="nowrap"> </span>kJ/g, 3.61<span class="nowrap"> </span>kcal/g </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Related compounds </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Other <a href="/wiki/Ion" title="Ion">anions</a></div> </td> <td>Lactate </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Related <a href="/wiki/Carboxylic_acid" title="Carboxylic acid">carboxylic acids</a></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a href="/wiki/Acetic_acid" title="Acetic acid">Acetic acid</a></li><li><a href="/wiki/Glycolic_acid" title="Glycolic acid">Glycolic acid</a></li><li><a href="/wiki/Propionic_acid" title="Propionic acid">Propionic acid</a></li><li><a href="/wiki/3-Hydroxypropanoic_acid" class="mw-redirect" title="3-Hydroxypropanoic acid">3-Hydroxypropanoic acid</a></li><li><a href="/wiki/Malonic_acid" title="Malonic acid">Malonic acid</a></li><li><a href="/wiki/Butyric_acid" title="Butyric acid">Butyric acid</a></li><li><a href="/wiki/Hydroxybutyric_acid" title="Hydroxybutyric acid">Hydroxybutyric acid</a></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Related compounds</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a href="/wiki/1-Propanol" title="1-Propanol">1-Propanol</a></li><li><a href="/wiki/2-Propanol" class="mw-redirect" title="2-Propanol">2-Propanol</a></li><li><a href="/wiki/Propionaldehyde" title="Propionaldehyde">Propionaldehyde</a></li><li><a href="/wiki/Acrolein" title="Acrolein">Acrolein</a></li><li><a href="/wiki/Sodium_lactate" title="Sodium lactate">Sodium lactate</a></li><li><a href="/wiki/Ethyl_lactate" title="Ethyl lactate">Ethyl lactate</a></li></ul></div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Pharmacology </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Anatomical_Therapeutic_Chemical_Classification_System" title="Anatomical Therapeutic Chemical Classification System">ATC code</a></div> </td> <td><a href="/wiki/ATC_code_G01" title="ATC code G01">G01AD01</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=G01AD01">WHO</a></span>) <a href="/wiki/ATC_code_P53" class="mw-redirect" title="ATC code P53">QP53AG02</a> (<span title="www.whocc.no/atcvet"><a rel="nofollow" class="external text" href="https://www.whocc.no/atcvet/atcvet_index/?code=QP53AG02">WHO</a></span>) </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Hazards </th></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;"><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><sup id="cite_ref-sigma_5-0" class="reference"><a href="#cite_note-sigma-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </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="H315: Causes skin irritation">H315</abbr>, <abbr class="abbr" title="H318: Causes serious eye damage">H318</abbr><sup id="cite_ref-sigma_5-1" class="reference"><a href="#cite_note-sigma-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </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="P280: Wear protective gloves/protective clothing/eye protection/face protection.">P280</abbr>, <abbr class="abbr" title="P305+P351+P338: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do. Continue rinsing.">P305+P351+P338</abbr><sup id="cite_ref-sigma_5-2" class="reference"><a href="#cite_note-sigma-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"><div style="text-align:center;"><span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/12px-Yes_check.svg.png" decoding="async" width="12" height="12" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/18px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/24px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span> <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=477002503&page2=Lactic+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>Lactic acid</b> is an <a href="/wiki/Organic_acid" title="Organic acid">organic acid</a>. It has the molecular formula <b>C<sub>3</sub>H<sub>6</sub>O<sub>3</sub></b>. It is white in the solid state and it is <a href="/wiki/Miscibility" title="Miscibility">miscible</a> with water.<sup id="cite_ref-GESTIS_2-1" class="reference"><a href="#cite_note-GESTIS-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> When in the dissolved state, it forms a colorless solution. Production includes both artificial synthesis as well as natural sources. Lactic acid is an <a href="/wiki/Alpha-hydroxy_acid" class="mw-redirect" title="Alpha-hydroxy acid">alpha-hydroxy acid</a> (AHA) due to the presence of a <a href="/wiki/Hydroxyl" class="mw-redirect" title="Hydroxyl">hydroxyl</a> group adjacent to the <a href="/wiki/Carboxyl" class="mw-redirect" title="Carboxyl">carboxyl</a> group. It is used as a synthetic intermediate in many <a href="/wiki/Organic_synthesis" title="Organic synthesis">organic synthesis</a> industries and in various <a href="/wiki/Biochemical" class="mw-redirect" title="Biochemical">biochemical</a> industries. The <a href="/wiki/Conjugate_base" class="mw-redirect" title="Conjugate base">conjugate base</a> of lactic acid is called <b>lactate</b> (or the lactate anion). The name of the derived <a href="/wiki/Acyl_group" title="Acyl group">acyl group</a> is <b>lactoyl</b>. </p><p>In solution, it can ionize by a loss of a proton to produce the lactate <a href="/wiki/Ion" title="Ion">ion</a> <span class="chemf nowrap">CH<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">3</sub></span></span>CH(OH)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>. Compared to <a href="/wiki/Acetic_acid" title="Acetic acid">acetic acid</a>, its <a href="/wiki/Acid_dissociation_constant" title="Acid dissociation constant">p<i>K</i><sub>a</sub></a> is 1 unit less, meaning lactic acid is ten times more acidic than acetic acid. This higher acidity is the consequence of the intramolecular hydrogen bonding between the α-hydroxyl and the carboxylate group. </p><p>Lactic acid is <a href="/wiki/Chirality_(chemistry)" title="Chirality (chemistry)">chiral</a>, consisting of two <a href="/wiki/Enantiomer" title="Enantiomer">enantiomers</a>. One is known as <span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">L</span></span>-lactic acid, (<i>S</i>)-lactic acid, or (+)-lactic acid, and the other, its mirror image, is <span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">D</span></span>-lactic acid, (<i>R</i>)-lactic acid, or (−)-lactic acid. A mixture of the two in equal amounts is called <span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">DL</span></span>-lactic acid, or <a href="/wiki/Racemic" class="mw-redirect" title="Racemic">racemic</a> lactic acid. Lactic acid is <a href="/wiki/Hygroscopy" title="Hygroscopy">hygroscopic</a>. <span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">DL</span></span>-Lactic acid is <a href="/wiki/Miscible" class="mw-redirect" title="Miscible">miscible</a> with water and with ethanol above its melting point, which is about 16 to 18 °C (61 to 64 °F). <span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">D</span></span>-Lactic acid and <span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">L</span></span>-lactic acid have a higher melting point. Lactic acid produced by fermentation of milk is often racemic, although certain species of bacteria produce solely <span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">D</span></span>-lactic acid.<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> On the other hand, lactic acid produced by fermentation in animal muscles has the (<span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">L</span></span>) enantiomer and is sometimes called "sarcolactic" acid, from the Greek <span title="Ancient Greek (to 1453)-language romanization"><i lang="grc-Latn">sarx</i></span>, meaning "flesh". </p><p>In animals, <span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">L</span></span>-lactate is constantly produced from <a href="/wiki/Pyruvate" class="mw-redirect" title="Pyruvate">pyruvate</a> via the <a href="/wiki/Enzyme" title="Enzyme">enzyme</a> <a href="/wiki/Lactate_dehydrogenase" title="Lactate dehydrogenase">lactate dehydrogenase</a> (LDH) in a process of <a href="/wiki/Fermentation_(biochemistry)" class="mw-redirect" title="Fermentation (biochemistry)">fermentation</a> during normal <a href="/wiki/Metabolism" title="Metabolism">metabolism</a> and <a href="/wiki/Exercise" title="Exercise">exercise</a>.<sup id="cite_ref-Skeletal_muscle_PGC-1α_controls_who_7-0" class="reference"><a href="#cite_note-Skeletal_muscle_PGC-1α_controls_who-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> It does not increase in concentration until the rate of lactate production exceeds the rate of lactate removal, which is governed by a number of factors, including <a href="/wiki/Monocarboxylate_transporter" title="Monocarboxylate transporter">monocarboxylate transporters</a>, concentration and isoform of LDH, and oxidative capacity of tissues.<sup id="cite_ref-Skeletal_muscle_PGC-1α_controls_who_7-1" class="reference"><a href="#cite_note-Skeletal_muscle_PGC-1α_controls_who-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> The concentration of <a href="/wiki/Blood" title="Blood">blood</a> lactate is usually <span class="nowrap">1–2</span><span class="nowrap"> </span><a href="/wiki/Millimolar" class="mw-redirect" title="Millimolar"><abbr title="millimolar">mM</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip millimolar</span> at rest, but can rise to over 20<span class="nowrap"> </span>mM during intense exertion and as high as 25<span class="nowrap"> </span>mM afterward.<sup id="cite_ref-LA-UCD_8-0" class="reference"><a href="#cite_note-LA-UCD-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> In addition to other biological roles, <span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">L</span></span>-lactic acid is the primary <a href="/wiki/Endogenous" class="mw-redirect" title="Endogenous">endogenous</a> <a href="/wiki/Agonist" title="Agonist">agonist</a> of <a href="/wiki/Hydroxycarboxylic_acid_receptor_1" title="Hydroxycarboxylic acid receptor 1">hydroxycarboxylic acid receptor 1</a> (HCA<sub>1</sub>), which is a <span class="nowrap"><a href="/wiki/Gi_alpha_subunit" title="Gi alpha subunit">G<sub>i/o</sub>-coupled</a></span> <a href="/wiki/G_protein-coupled_receptor" title="G protein-coupled receptor">G protein-coupled receptor</a> (GPCR).<sup id="cite_ref-IUPHAR's_comprehensive_2011_review_on_HCARs_10-0" class="reference"><a href="#cite_note-IUPHAR's_comprehensive_2011_review_on_HCARs-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-IUPHAR-DB_HCAR_family_page_11-0" class="reference"><a href="#cite_note-IUPHAR-DB_HCAR_family_page-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p><p>In industry, <a href="/wiki/Lactic_acid_fermentation" title="Lactic acid fermentation">lactic acid fermentation</a> is performed by <a href="/wiki/Lactic_acid_bacteria" title="Lactic acid bacteria">lactic acid bacteria</a>, which convert simple <a href="/wiki/Carbohydrates" class="mw-redirect" title="Carbohydrates">carbohydrates</a> such as <a href="/wiki/Glucose" title="Glucose">glucose</a>, <a href="/wiki/Sucrose" title="Sucrose">sucrose</a>, or <a href="/wiki/Galactose" title="Galactose">galactose</a> to lactic acid. These bacteria can also grow in the <a href="/wiki/Mouth" title="Mouth">mouth</a>; the <a href="/wiki/Acid" title="Acid">acid</a> they produce is responsible for the <a href="/wiki/Tooth" title="Tooth">tooth</a> decay known as <a href="/wiki/Tooth_decay" title="Tooth decay">cavities</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><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><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><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> In <a href="/wiki/Medicine" title="Medicine">medicine</a>, lactate is one of the main components of <a href="/wiki/Lactated_Ringer%27s_solution" class="mw-redirect" title="Lactated Ringer's solution">lactated Ringer's solution</a> and <a href="/wiki/Hartmann%27s_solution" class="mw-redirect" title="Hartmann's solution">Hartmann's solution</a>. These <a href="/wiki/Intravenous" class="mw-redirect" title="Intravenous">intravenous</a> fluids consist of <a href="/wiki/Sodium" title="Sodium">sodium</a> and <a href="/wiki/Potassium" title="Potassium">potassium</a> <a href="/wiki/Cation" class="mw-redirect" title="Cation">cations</a> along with lactate and <a href="/wiki/Chloride" title="Chloride">chloride</a> <a href="/wiki/Anion" class="mw-redirect" title="Anion">anions</a> in solution with distilled <a href="/wiki/Water" title="Water">water</a>, generally in concentrations <a href="/wiki/Isotonicity" class="mw-redirect" title="Isotonicity">isotonic</a> with <a href="/wiki/Human" title="Human">human</a> <a href="/wiki/Blood" title="Blood">blood</a>. It is most commonly used for fluid <a href="/wiki/Resuscitation" title="Resuscitation">resuscitation</a> after blood loss due to <a href="/wiki/Physical_trauma" class="mw-redirect" title="Physical trauma">trauma</a>, <a href="/wiki/Surgery" title="Surgery">surgery</a>, or <a href="/wiki/Burn_(injury)" class="mw-redirect" title="Burn (injury)">burns</a>. </p><p>Lactic acid is produced in human tissues when the demand for oxygen is limited by the supply. This occurs during tissue <a href="/wiki/Ischemia" title="Ischemia">ischemia</a> when the flow of blood is limited as in sepsis or hemorrhagic shock. It may also occur when demand for oxygen is high such as with intense exercise. The process of <a href="/wiki/Lactic_acidosis" title="Lactic acidosis">lactic acidosis</a> produces lactic acid which results in an <a href="https://en.wiktionary.org/wiki/oxygen_debt" class="extiw" title="wikt:oxygen debt">oxygen debt</a> which can be resolved or repaid when tissue oxygenation improves.<sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p> <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=Lactic_acid&action=edit&section=1" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Swedish chemist <a href="/wiki/Carl_Wilhelm_Scheele" title="Carl Wilhelm Scheele">Carl Wilhelm Scheele</a> was the first person to isolate lactic acid in 1780 from sour <a href="/wiki/Milk" title="Milk">milk</a>.<sup id="cite_ref-Parks_17-0" class="reference"><a href="#cite_note-Parks-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> The name reflects the <i><a href="https://en.wiktionary.org/wiki/lact-#Prefix" class="extiw" title="wikt:lact-">lact-</a></i> combining form derived from the Latin word <span title="Latin-language text"><i lang="la"><a href="https://en.wiktionary.org/wiki/lac#Latin" class="extiw" title="wikt:lac">lac</a></i></span>, meaning "milk". In 1808, <a href="/wiki/J%C3%B6ns_Jacob_Berzelius" title="Jöns Jacob Berzelius">Jöns Jacob Berzelius</a> discovered that lactic acid (actually <span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">L</span></span>-lactate) is also produced in <a href="/wiki/Muscle" title="Muscle">muscles</a> during exertion.<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> Its structure was established by <a href="/wiki/Johannes_Wislicenus" title="Johannes Wislicenus">Johannes Wislicenus</a> in 1873. </p><p>In 1856, the role of <i><a href="/wiki/Lactobacillus" title="Lactobacillus">Lactobacillus</a></i> in the synthesis of lactic acid was discovered by <a href="/wiki/Louis_Pasteur" title="Louis Pasteur">Louis Pasteur</a>. This pathway was used commercially by the German <a href="/wiki/Pharmacy" title="Pharmacy">pharmacy</a> <a href="/wiki/Boehringer_Ingelheim" title="Boehringer Ingelheim">Boehringer Ingelheim</a> in 1895.<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. (May 2024)">citation needed</span></a></i>]</sup> </p><p>In 2006, global production of lactic acid reached 275,000 tonnes with an average annual growth of 10%.<sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> </p> <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=Lactic_acid&action=edit&section=2" title="Edit section: Production"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Lactic acid is produced industrially by bacterial <a href="/wiki/Fermentation" title="Fermentation">fermentation</a> of <a href="/wiki/Carbohydrate" title="Carbohydrate">carbohydrates</a>, or by chemical synthesis from <a href="/wiki/Acetaldehyde" title="Acetaldehyde">acetaldehyde</a>.<sup id="cite_ref-benn_20-0" class="reference"><a href="#cite_note-benn-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> As of 2009<sup class="plainlinks noexcerpt noprint asof-tag update" style="display:none;"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Lactic_acid&action=edit">[update]</a></sup>, lactic acid was produced predominantly (70–90%)<sup id="cite_ref-21" class="reference"><a href="#cite_note-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> by fermentation. Production of racemic lactic acid consisting of a 1:1 mixture of <span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">D</span></span> and <span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">L</span></span> stereoisomers, or of mixtures with up to 99.9% <span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">L</span></span>-lactic acid, is possible by microbial fermentation. Industrial scale production of <span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">D</span></span>-lactic acid by fermentation is possible, but much more challenging.<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. (May 2024)">citation needed</span></a></i>]</sup> </p> <div class="mw-heading mw-heading3"><h3 id="Fermentative_production">Fermentative production</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lactic_acid&action=edit&section=3" title="Edit section: Fermentative production"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Fermented_milk_products" class="mw-redirect" title="Fermented milk products">Fermented milk products</a> are obtained industrially by fermentation of <a href="/wiki/Milk" title="Milk">milk</a> or <a href="/wiki/Whey" title="Whey">whey</a> by <i>Lactobacillus</i> bacteria: <i><a href="/wiki/Lactobacillus_acidophilus" title="Lactobacillus acidophilus">Lactobacillus acidophilus</a></i>, <i><a href="/wiki/Lacticaseibacillus_casei" title="Lacticaseibacillus casei">Lacticaseibacillus casei</a></i> (<i>Lactobacillus casei</i>), <a href="/wiki/Lactobacillus_delbrueckii_subsp._bulgaricus" title="Lactobacillus delbrueckii subsp. bulgaricus"><i>Lactobacillus delbrueckii</i> subsp. <i>bulgaricus</i></a> (<i>Lactobacillus bulgaricus</i>), <i><a href="/wiki/Lactobacillus_helveticus" title="Lactobacillus helveticus">Lactobacillus helveticus</a></i>, <i><a href="/wiki/Lactococcus_lactis" title="Lactococcus lactis">Lactococcus lactis</a></i> ,<i> <a href="/wiki/Bacillus_amyloliquefaciens" title="Bacillus amyloliquefaciens">Bacillus amyloliquefaciens</a></i>, and <a href="/wiki/Streptococcus_salivarius_subsp._thermophilus" class="mw-redirect" title="Streptococcus salivarius subsp. thermophilus"><i>Streptococcus salivarius</i> subsp. <i>thermophilus</i></a> (<i>Streptococcus thermophilus</i>).<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. (May 2024)">citation needed</span></a></i>]</sup> </p><p>As a starting material for industrial production of lactic acid, almost any carbohydrate source containing <span class="chemf nowrap"><a href="/wiki/Pentose" title="Pentose">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">5</sub></span></span></a></span> (Pentose sugar) and <span class="chemf nowrap"><a href="/wiki/Hexose" title="Hexose">C<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">6</sub></span></span></a></span> (Hexose sugar) can be used. Pure sucrose, glucose from starch, raw sugar, and beet juice are frequently used.<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> Lactic acid producing bacteria can be divided in two classes: homofermentative bacteria like <i>Lactobacillus casei</i> and <i>Lactococcus lactis</i>, producing two moles of lactate from one mole of glucose, and heterofermentative species producing one mole of lactate from one mole of glucose as well as <a href="/wiki/Carbon_dioxide" title="Carbon dioxide">carbon dioxide</a> and <a href="/wiki/Acetic_acid" title="Acetic acid">acetic acid</a>/<a href="/wiki/Ethanol" title="Ethanol">ethanol</a>.<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> </p> <div class="mw-heading mw-heading3"><h3 id="Chemical_production">Chemical production</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lactic_acid&action=edit&section=4" title="Edit section: Chemical production"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Racemic lactic acid is synthesized industrially by reacting <a href="/wiki/Acetaldehyde" title="Acetaldehyde">acetaldehyde</a> with <a href="/wiki/Hydrogen_cyanide" title="Hydrogen cyanide">hydrogen cyanide</a> and hydrolysing the resultant <a href="/wiki/Lactonitrile" title="Lactonitrile">lactonitrile</a>. When <a href="/wiki/Hydrolysis" title="Hydrolysis">hydrolysis</a> is performed by <a href="/wiki/Hydrochloric_acid" title="Hydrochloric acid">hydrochloric acid</a>, <a href="/wiki/Ammonium_chloride" title="Ammonium chloride">ammonium chloride</a> forms as a by-product; the Japanese company Musashino is one of the last big manufacturers of lactic acid by this route.<sup id="cite_ref-24" class="reference"><a href="#cite_note-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> Synthesis of both racemic and enantiopure lactic acids is also possible from other starting materials (<a href="/wiki/Vinyl_acetate" title="Vinyl acetate">vinyl acetate</a>, <a href="/wiki/Glycerol" title="Glycerol">glycerol</a>, etc.) by application of catalytic procedures.<sup id="cite_ref-25" class="reference"><a href="#cite_note-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Biology">Biology</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lactic_acid&action=edit&section=5" title="Edit section: Biology"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Molecular_biology">Molecular biology</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lactic_acid&action=edit&section=6" title="Edit section: Molecular biology"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">L</span></span>-Lactic acid is the primary <a href="/wiki/Endogenous" class="mw-redirect" title="Endogenous">endogenous</a> <a href="/wiki/Agonist" title="Agonist">agonist</a> of <a href="/wiki/Hydroxycarboxylic_acid_receptor_1" title="Hydroxycarboxylic acid receptor 1">hydroxycarboxylic acid receptor 1</a> (HCA<sub>1</sub>), a <span class="nowrap"><a href="/wiki/Gi_alpha_subunit" title="Gi alpha subunit">G<sub>i/o</sub>-coupled</a></span> <a href="/wiki/G_protein-coupled_receptor" title="G protein-coupled receptor">G protein-coupled receptor</a> (GPCR).<sup id="cite_ref-IUPHAR's_comprehensive_2011_review_on_HCARs_10-1" class="reference"><a href="#cite_note-IUPHAR's_comprehensive_2011_review_on_HCARs-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-IUPHAR-DB_HCAR_family_page_11-1" class="reference"><a href="#cite_note-IUPHAR-DB_HCAR_family_page-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Metabolism_and_exercise">Metabolism and exercise</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lactic_acid&action=edit&section=7" title="Edit section: Metabolism and exercise"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/N-Lactoylphenylalanine" class="mw-redirect" title="N-Lactoylphenylalanine">N-Lactoylphenylalanine</a></div> <p>During power exercises such as <a href="/wiki/Sprint_(running)" title="Sprint (running)">sprinting</a>, when the rate of demand for energy is high, <a href="/wiki/Glucose" title="Glucose">glucose</a> is broken down and oxidized to <a href="/wiki/Pyruvate" class="mw-redirect" title="Pyruvate">pyruvate</a>, and lactate is then produced from the pyruvate faster than the body can process it, causing lactate concentrations to rise. The production of lactate is beneficial for <a href="/wiki/Nicotinamide_adenine_dinucleotide" title="Nicotinamide adenine dinucleotide">NAD<sup>+</sup></a> regeneration (pyruvate is reduced to lactate while NADH is oxidized to NAD<sup>+</sup>), which is used up in oxidation of <a href="/wiki/Glyceraldehyde_3-phosphate" title="Glyceraldehyde 3-phosphate">glyceraldehyde 3-phosphate</a> during production of pyruvate from glucose, and this ensures that energy production is maintained and exercise can continue. During intense exercise, the respiratory chain cannot keep up with the amount of hydrogen ions that join to form NADH, and cannot regenerate NAD<sup>+</sup> quickly enough, so pyruvate is converted to lactate to allow energy production by <a href="/wiki/Glycolysis" title="Glycolysis">glycolysis</a> to continue.<sup id="cite_ref-Ferguson_2018_26-0" class="reference"><a href="#cite_note-Ferguson_2018-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> </p><p>The resulting lactate can be used in two ways: </p> <ul><li><a href="/wiki/Oxidation" class="mw-redirect" title="Oxidation">Oxidation</a> back to <a href="/wiki/Pyruvate" class="mw-redirect" title="Pyruvate">pyruvate</a> by well-oxygenated <a href="/wiki/Muscle" title="Muscle">muscle</a> cells, heart cells, and brain cells <ul><li>Pyruvate is then directly used to fuel the <a href="/wiki/Krebs_cycle" class="mw-redirect" title="Krebs cycle">Krebs cycle</a></li></ul></li> <li>Conversion to <a href="/wiki/Glucose" title="Glucose">glucose</a> via <a href="/wiki/Gluconeogenesis" title="Gluconeogenesis">gluconeogenesis</a> in the liver and release back into circulation by means of the <a href="/wiki/Cori_cycle" title="Cori cycle">Cori cycle</a><sup id="cite_ref-mcardlekatch_27-0" class="reference"><a href="#cite_note-mcardlekatch-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> <ul><li>If blood glucose concentrations are high, the glucose can be used to build up the liver's <a href="/wiki/Glycogen" title="Glycogen">glycogen</a> stores.</li></ul></li></ul> <p>Lactate is continually formed at rest and during all exercise intensities. Lactate serves as a metabolic fuel being produced and oxidatively disposed in resting and exercising muscle and other tissues.<sup id="cite_ref-Ferguson_2018_26-1" class="reference"><a href="#cite_note-Ferguson_2018-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> Some sources of excess lactate production are metabolism in <a href="/wiki/Red_blood_cell" title="Red blood cell">red blood cells</a>, which lack <a href="/wiki/Mitochondria" class="mw-redirect" title="Mitochondria">mitochondria</a> that perform aerobic respiration, and limitations in the rates of enzyme activity in muscle fibers during intense exertion.<sup id="cite_ref-mcardlekatch_27-1" class="reference"><a href="#cite_note-mcardlekatch-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Lactic_acidosis" title="Lactic acidosis">Lactic acidosis</a> is a <a href="/wiki/Physiology" title="Physiology">physiological condition</a> characterized by accumulation of lactate (especially <span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">L</span></span>-lactate), with formation of an excessively high proton concentration [H<sup>+</sup>] and correspondingly low <a href="/wiki/PH" title="PH">pH</a> in the tissues, a form of <a href="/wiki/Metabolic_acidosis" title="Metabolic acidosis">metabolic acidosis</a>.<sup id="cite_ref-Ferguson_2018_26-2" class="reference"><a href="#cite_note-Ferguson_2018-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> </p><p>The first stage in metabolizing glucose is <a href="/wiki/Glycolysis" title="Glycolysis">glycolysis</a>, the conversion of glucose to pyruvate<sup>−</sup> and H<sup>+</sup>: </p> <dl><dd><style data-mw-deduplicate="TemplateStyles:r1123817410">.mw-parser-output .template-chem2-su{display:inline-block;font-size:80%;line-height:1;vertical-align:-0.35em}.mw-parser-output .template-chem2-su>span{display:block;text-align:left}.mw-parser-output sub.template-chem2-sub{font-size:80%;vertical-align:-0.35em}.mw-parser-output sup.template-chem2-sup{font-size:80%;vertical-align:0.65em}</style><span class="chemf nowrap">C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">12</sub>O<sub class="template-chem2-sub">6</sub> + 2 NAD<sup class="template-chem2-sup">+</sup> + 2 ADP<sup>3−</sup> + 2 HPO<span class="template-chem2-su"><span>2−</span><span>4</span></span> → 2 CH<sub class="template-chem2-sub">3</sub>COCO<span class="template-chem2-su"><span>−</span><span>2</span></span> + 2 H<sup class="template-chem2-sup">+</sup> + 2 NADH + 2 ATP<sup>4−</sup> + 2 H<sub class="template-chem2-sub">2</sub>O</span></dd></dl> <p>When sufficient oxygen is present for aerobic respiration, the pyruvate is oxidized to <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CO<sub class="template-chem2-sub">2</sub></span> and water by the Krebs cycle, in which <a href="/wiki/Oxidative_phosphorylation" title="Oxidative phosphorylation">oxidative phosphorylation</a> generates ATP for use in powering the cell. When insufficient oxygen is present, or when there is insufficient capacity for pyruvate oxidation to keep up with rapid pyruvate production during intense exertion, the pyruvate is converted to lactate<sup>−</sup> by <a href="/wiki/Lactate_dehydrogenase" title="Lactate dehydrogenase">lactate dehydrogenase</a>), a process that absorbs these protons:<sup id="cite_ref-Robergs_28-0" class="reference"><a href="#cite_note-Robergs-28"><span class="cite-bracket">[</span>28<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">2 CH<sub class="template-chem2-sub">3</sub>COCO<span class="template-chem2-su"><span>−</span><span>2</span></span> + 2 H<sup class="template-chem2-sup">+</sup> + 2 NADH → 2 CH<sub class="template-chem2-sub">3</sub>CH(OH)CO<span class="template-chem2-su"><span>−</span><span>2</span></span> + 2 NAD<sup class="template-chem2-sup">+</sup></span></dd></dl> <p>The combined effect is: </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">12</sub>O<sub class="template-chem2-sub">6</sub> + 2 ADP<sup>3−</sup> + 2HPO<span class="template-chem2-su"><span>2−</span><span>4</span></span> → 2 CH<sub class="template-chem2-sub">3</sub>CH(OH)CO<span class="template-chem2-su"><span>−</span><span>2</span></span> + 2 ATP<sup>4−</sup> + 2 H<sub class="template-chem2-sub">2</sub>O</span></dd></dl> <p>The production of lactate from glucose (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">glucose → 2 lactate<sup class="template-chem2-sup">−</sup> + 2 H<sup class="template-chem2-sup">+</sup></span>), when viewed in isolation, releases two H<sup>+</sup>. The H<sup>+</sup> are absorbed in the production of ATP, but H<sup>+</sup> is subsequently released during hydrolysis of ATP: </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">ATP<sup>4−</sup> + H<sub class="template-chem2-sub">2</sub>O → ADP<sup>3−</sup> + HPO<span class="template-chem2-su"><span>2−</span><span>4</span></span> + H<sup class="template-chem2-sup">+</sup></span></dd></dl> <p>Once the production and use of ATP is included, the overall reaction is </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">12</sub>O<sub class="template-chem2-sub">6</sub> → 2 CH<sub class="template-chem2-sub">3</sub>CH(OH)CO<span class="template-chem2-su"><span>−</span><span>2</span></span> + 2 H<sup class="template-chem2-sup">+</sup></span></dd></dl> <p>The resulting increase in acidity persists until the excess lactate and protons are converted back to pyruvate, and then to glucose for later use, or to <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CO<sub class="template-chem2-sub">2</sub></span> and water for the production of ATP.<sup id="cite_ref-Ferguson_2018_26-3" class="reference"><a href="#cite_note-Ferguson_2018-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Neural_tissue_energy_source">Neural tissue energy source</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lactic_acid&action=edit&section=8" title="Edit section: Neural tissue energy source"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Although <a href="/wiki/Glucose" title="Glucose">glucose</a> is usually assumed to be the main energy source for living tissues, there is evidence that lactate, in preference to glucose, is preferentially metabolized by <a href="/wiki/Neuron" title="Neuron">neurons</a> in the <a href="/wiki/Brain" title="Brain">brains</a> of several <a href="/wiki/Mammalian" class="mw-redirect" title="Mammalian">mammalian</a> species that include <a href="/wiki/Mouse" title="Mouse">mice</a>, <a href="/wiki/Rat" title="Rat">rats</a>, and <a href="/wiki/Human" title="Human">humans</a>.<sup id="cite_ref-zilberter2010_29-0" class="reference"><a href="#cite_note-zilberter2010-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup><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><sup id="cite_ref-Ferguson_2018_26-4" class="reference"><a href="#cite_note-Ferguson_2018-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> According to the <a href="/wiki/Lactate_shuttle" class="mw-redirect" title="Lactate shuttle">lactate-shuttle hypothesis</a>, <a href="/wiki/Glia" title="Glia">glial</a> cells are responsible for transforming glucose into lactate, and for providing lactate to the neurons.<sup id="cite_ref-31" class="reference"><a href="#cite_note-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-32" class="reference"><a href="#cite_note-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> Because of this local metabolic activity of glial cells, the <a href="/wiki/Extracellular_fluid" title="Extracellular fluid">extracellular fluid</a> immediately surrounding neurons strongly differs in composition from the <a href="/wiki/Blood" title="Blood">blood</a> or <a href="/wiki/Cerebrospinal_fluid" title="Cerebrospinal fluid">cerebrospinal fluid</a>, being much richer with lactate, as was found in <a href="/wiki/Microdialysis" title="Microdialysis">microdialysis</a> studies.<sup id="cite_ref-zilberter2010_29-1" class="reference"><a href="#cite_note-zilberter2010-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Brain_development_metabolism">Brain development metabolism</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lactic_acid&action=edit&section=9" title="Edit section: Brain development metabolism"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Some evidence suggests that lactate is important at early stages of development for brain metabolism in <a href="/wiki/Prenatal" class="mw-redirect" title="Prenatal">prenatal</a> and early <a href="/wiki/Postnatal" class="mw-redirect" title="Postnatal">postnatal</a> subjects, with lactate at these stages having higher concentrations in body liquids, and being utilized by the brain preferentially over glucose.<sup id="cite_ref-zilberter2010_29-2" class="reference"><a href="#cite_note-zilberter2010-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> It was also hypothesized that lactate may exert a strong action over <a href="/wiki/GABA" title="GABA">GABAergic</a> networks in the <a href="/wiki/Brain_development" class="mw-redirect" title="Brain development">developing brain</a>, making them more <a href="/wiki/Inhibitory" class="mw-redirect" title="Inhibitory">inhibitory</a> than it was previously assumed,<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> acting either through better support of metabolites,<sup id="cite_ref-zilberter2010_29-3" class="reference"><a href="#cite_note-zilberter2010-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> or alterations in base intracellular <a href="/wiki/PH" title="PH">pH</a> levels,<sup id="cite_ref-34" class="reference"><a href="#cite_note-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-35" class="reference"><a href="#cite_note-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> or both.<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><p>Studies of brain slices of mice show that <a href="/wiki/Beta-hydroxybutyrate" class="mw-redirect" title="Beta-hydroxybutyrate">β-hydroxybutyrate</a>, lactate, and pyruvate act as oxidative energy substrates, causing an increase in the NAD(P)H oxidation phase, that glucose was insufficient as an energy carrier during intense synaptic activity and, finally, that lactate can be an efficient energy substrate capable of sustaining and enhancing brain aerobic energy metabolism <i>in vitro</i>.<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 study "provides novel data on biphasic NAD(P)H fluorescence transients, an important physiological response to neural activation that has been reproduced in many studies and that is believed to originate predominantly from activity-induced concentration changes to the cellular NADH pools."<sup id="cite_ref-38" class="reference"><a href="#cite_note-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup> </p><p>Lactate can also serve as an important source of energy for other organs, including the heart and liver. During physical activity, up to 60% of the heart muscle's energy turnover rate derives from lactate oxidation.<sup id="cite_ref-Parks_17-1" class="reference"><a href="#cite_note-Parks-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Blood_testing">Blood testing</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lactic_acid&action=edit&section=10" title="Edit section: Blood testing"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Blood_values_sorted_by_mass_and_molar_concentration.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/cb/Blood_values_sorted_by_mass_and_molar_concentration.png/450px-Blood_values_sorted_by_mass_and_molar_concentration.png" decoding="async" width="450" height="65" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/cb/Blood_values_sorted_by_mass_and_molar_concentration.png/675px-Blood_values_sorted_by_mass_and_molar_concentration.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/cb/Blood_values_sorted_by_mass_and_molar_concentration.png/900px-Blood_values_sorted_by_mass_and_molar_concentration.png 2x" data-file-width="6798" data-file-height="977" /></a><figcaption><a href="/wiki/Reference_ranges_for_blood_tests" title="Reference ranges for blood tests">Reference ranges for blood tests</a>, comparing lactate content (shown in violet at center-right) to other constituents in human blood</figcaption></figure> <p><a href="/wiki/Blood_test" title="Blood test">Blood tests</a> for lactate are performed to determine the status of the <a href="/wiki/Acid_base_homeostasis" class="mw-redirect" title="Acid base homeostasis">acid base homeostasis</a> in the body. <a href="/wiki/Blood_sampling" class="mw-redirect" title="Blood sampling">Blood sampling</a> for this purpose is often <a href="/wiki/Arterial_blood_sampling" class="mw-redirect" title="Arterial blood sampling">arterial</a> (even if it is more difficult than <a href="/wiki/Venipuncture" title="Venipuncture">venipuncture</a>), because lactate levels differ substantially between arterial and venous, and the arterial level is more representative for this purpose. </p> <table class="wikitable"> <caption>Reference ranges </caption> <tbody><tr> <th> </th> <th>Lower limit </th> <th>Upper limit </th> <th>Unit </th></tr> <tr> <th rowspan="2">Venous </th> <td>4.5<sup id="cite_ref-bloodbook_39-0" class="reference"><a href="#cite_note-bloodbook-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup></td> <td>19.8<sup id="cite_ref-bloodbook_39-1" class="reference"><a href="#cite_note-bloodbook-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup></td> <td>mg/dL </td></tr> <tr> <td>0.5<sup id="cite_ref-lactate-mass_40-0" class="reference"><a href="#cite_note-lactate-mass-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup></td> <td>2.2<sup id="cite_ref-lactate-mass_40-1" class="reference"><a href="#cite_note-lactate-mass-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup></td> <td>mmol/L </td></tr> <tr> <th rowspan="2">Arterial </th> <td>4.5<sup id="cite_ref-bloodbook_39-2" class="reference"><a href="#cite_note-bloodbook-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup></td> <td>14.4<sup id="cite_ref-bloodbook_39-3" class="reference"><a href="#cite_note-bloodbook-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup></td> <td>mg/dL </td></tr> <tr> <td>0.5<sup id="cite_ref-lactate-mass_40-2" class="reference"><a href="#cite_note-lactate-mass-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup></td> <td>1.6<sup id="cite_ref-lactate-mass_40-3" class="reference"><a href="#cite_note-lactate-mass-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup></td> <td>mmol/L </td></tr></tbody></table> <p>During <a href="/wiki/Childbirth" title="Childbirth">childbirth</a>, lactate levels in the fetus can be quantified by <a href="/wiki/Fetal_scalp_blood_testing" title="Fetal scalp blood testing">fetal scalp blood testing</a>. </p> <div class="mw-heading mw-heading2"><h2 id="Uses">Uses</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lactic_acid&action=edit&section=11" title="Edit section: Uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Polymer_precursor">Polymer precursor</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lactic_acid&action=edit&section=12" title="Edit section: Polymer precursor"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Polylactic_acid" title="Polylactic acid">polylactic acid</a></div> <p>Two molecules of lactic acid can be dehydrated to the <a href="/wiki/Lactone" title="Lactone">lactone</a> <a href="/wiki/Lactide" title="Lactide">lactide</a>. In the presence of <a href="/wiki/Catalysts" class="mw-redirect" title="Catalysts">catalysts</a> lactide polymerize to either atactic or <a href="/wiki/Syndiotactic" class="mw-redirect" title="Syndiotactic">syndiotactic</a> <a href="/wiki/Polylactic_acid" title="Polylactic acid">polylactide</a> (PLA), which are <a href="/wiki/Biodegradable" class="mw-redirect" title="Biodegradable">biodegradable</a> <a href="/wiki/Polyester" title="Polyester">polyesters</a>. PLA is an example of a plastic that is not derived from <a href="/wiki/Petrochemical" title="Petrochemical">petrochemicals</a>. </p> <div class="mw-heading mw-heading3"><h3 id="Pharmaceutical_and_cosmetic_applications">Pharmaceutical and cosmetic applications</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lactic_acid&action=edit&section=13" title="Edit section: Pharmaceutical and cosmetic applications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Lactic acid is also employed in <a href="/wiki/Pharmaceutical_technology" class="mw-redirect" title="Pharmaceutical technology">pharmaceutical technology</a> to produce water-soluble lactates from otherwise-insoluble active ingredients. It finds further use in topical preparations and <a href="/wiki/Cosmetics" title="Cosmetics">cosmetics</a> to adjust acidity and for its <a href="/wiki/Disinfectant" title="Disinfectant">disinfectant</a> and <a href="/wiki/Keratolytic" title="Keratolytic">keratolytic</a> properties. </p><p>Lactic acid containing bacteria have shown promise in reducing <a href="/wiki/Oxaluria" class="mw-redirect" title="Oxaluria">oxaluria</a> with its descaling properties on calcium compounds.<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="Foods">Foods</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lactic_acid&action=edit&section=14" title="Edit section: Foods"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading4"><h4 id="Fermented_food">Fermented food</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lactic_acid&action=edit&section=15" title="Edit section: Fermented food"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Lactic acid is found primarily in sour <a href="/wiki/Milk" title="Milk">milk</a> products, such as <a href="/wiki/Kumis" title="Kumis">kumis</a>, <a href="/wiki/Strained_yogurt" title="Strained yogurt">laban</a>, <a href="/wiki/Yogurt" title="Yogurt">yogurt</a>, <a href="/wiki/Kefir" title="Kefir">kefir</a>, and some <a href="/wiki/Cottage_cheese" title="Cottage cheese">cottage cheeses</a>. The <a href="/wiki/Casein" title="Casein">casein</a> in fermented milk is coagulated (curdled) by lactic acid. Lactic acid is also responsible for the sour flavor of <a href="/wiki/Sourdough" title="Sourdough">sourdough</a> bread. </p><p>In lists of <a href="/wiki/Nutritional_information" class="mw-redirect" title="Nutritional information">nutritional information</a> lactic acid might be included under the term "carbohydrate" (or "carbohydrate by difference") because this often includes everything other than water, protein, fat, ash, and ethanol.<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> If this is the case then the calculated <a href="/wiki/Food_energy" title="Food energy">food energy</a> may use the standard 4 kilocalories (17 kJ) per gram that is often used for all carbohydrates. But in some cases lactic acid is ignored in the calculation.<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> The energy density of lactic acid is 362 kilocalories (1,510 kJ) per 100 g.<sup id="cite_ref-FAOSouthgate_44-0" class="reference"><a href="#cite_note-FAOSouthgate-44"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup> </p><p>Some beers (<a href="/wiki/Sour_beer" title="Sour beer">sour beer</a>) purposely contain lactic acid, one such type being Belgian <a href="/wiki/Lambic" title="Lambic">lambics</a>. Most commonly, this is produced naturally by various strains of bacteria. These bacteria ferment sugars into acids, unlike the yeast that ferment sugar into ethanol. After cooling the <a href="/wiki/Wort" title="Wort">wort</a>, yeast and bacteria are allowed to "fall" into the open fermenters. Brewers of more common beer styles would ensure that no such bacteria are allowed to enter the fermenter. Other sour styles of beer include <a href="/wiki/Berliner_weisse" class="mw-redirect" title="Berliner weisse">Berliner weisse</a>, <a href="/wiki/Flanders_red" class="mw-redirect" title="Flanders red">Flanders red</a> and <a href="/wiki/American_wild_ale" title="American wild ale">American wild ale</a>.<sup id="cite_ref-45" class="reference"><a href="#cite_note-45"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-46" class="reference"><a href="#cite_note-46"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup> </p><p>In winemaking, a bacterial process, natural or controlled, is often used to convert the naturally present <a href="/wiki/Malic_acid" title="Malic acid">malic acid</a> to lactic acid, to reduce the sharpness and for other flavor-related reasons. This <a href="/wiki/Malolactic_fermentation" title="Malolactic fermentation">malolactic fermentation</a> is undertaken by <a href="/wiki/Lactic_acid_bacteria" title="Lactic acid bacteria">lactic acid bacteria</a>. </p><p>While not normally found in significant quantities in fruit, lactic acid is the primary organic acid in <a href="/wiki/Akebia" title="Akebia">akebia</a> fruit, making up 2.12% of the juice.<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-heading4"><h4 id="Separately_added">Separately added</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lactic_acid&action=edit&section=16" title="Edit section: Separately added"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>As a <a href="/wiki/Food_additive" title="Food additive">food additive</a> it is approved for use in the EU,<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> United States<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> and Australia and New Zealand;<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> it is listed by its <a href="/wiki/INS_number" class="mw-redirect" title="INS number">INS number</a> 270 or as <a href="/wiki/E_number" title="E number">E number</a> E270. Lactic acid is used as a food preservative, curing agent, and flavoring agent.<sup id="cite_ref-fda-lactic-acid_51-0" class="reference"><a href="#cite_note-fda-lactic-acid-51"><span class="cite-bracket">[</span>51<span class="cite-bracket">]</span></a></sup> It is an ingredient in processed foods and is used as a decontaminant during meat processing.<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> Lactic acid is produced commercially by fermentation of carbohydrates such as glucose, sucrose, or lactose, or by chemical synthesis.<sup id="cite_ref-fda-lactic-acid_51-1" class="reference"><a href="#cite_note-fda-lactic-acid-51"><span class="cite-bracket">[</span>51<span class="cite-bracket">]</span></a></sup> Carbohydrate sources include corn, beets, and cane sugar.<sup id="cite_ref-53" class="reference"><a href="#cite_note-53"><span class="cite-bracket">[</span>53<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Forgery">Forgery</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lactic_acid&action=edit&section=17" title="Edit section: Forgery"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Lactic acid has historically been used to assist with the erasure of inks from official papers to be modified during <a href="/wiki/Forgery" title="Forgery">forgery</a>.<sup id="cite_ref-54" class="reference"><a href="#cite_note-54"><span class="cite-bracket">[</span>54<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Cleaning_products">Cleaning products</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lactic_acid&action=edit&section=18" title="Edit section: Cleaning products"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Lactic acid is used in some liquid cleaners as a <a href="/wiki/Descaling_agent" title="Descaling agent">descaling agent</a> for removing <a href="/wiki/Hard_water" title="Hard water">hard water</a> deposits such as <a href="/wiki/Calcium_carbonate" title="Calcium carbonate">calcium carbonate</a>.<sup id="cite_ref-55" class="reference"><a href="#cite_note-55"><span class="cite-bracket">[</span>55<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lactic_acid&action=edit&section=19" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Category:Lactates" title="Category:Lactates">Category: Salts of lactic acid</a></li> <li><a href="/wiki/Category:Lactate_esters" title="Category:Lactate esters">Category:Lactate esters</a></li> <li><a href="/wiki/Acids_in_wine" title="Acids in wine">Acids in wine</a></li> <li><a href="/wiki/Alanine_cycle" class="mw-redirect" title="Alanine cycle">Alanine cycle</a></li> <li><a href="/wiki/Biodegradable_plastic" title="Biodegradable plastic">Biodegradable plastic</a></li> <li><a href="/wiki/Dental_caries" class="mw-redirect" title="Dental caries">Dental caries</a></li> <li><a href="/wiki/MCT1" class="mw-redirect" title="MCT1">MCT1</a>, a lactate transporter</li> <li><a href="/wiki/Thiolactic_acid" title="Thiolactic acid">Thiolactic acid</a></li> <li><a href="/wiki/Methacrylic_acid" title="Methacrylic acid">Methacrylic acid</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lactic_acid&action=edit&section=20" 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">"CHAPTER P-6. Applications to Specific Classes of Compounds". <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. p. 748. <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%2F9781849733069-00648">10.1039/9781849733069-00648</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=CHAPTER+P-6.+Applications+to+Specific+Classes+of+Compounds&rft.btitle=Nomenclature+of+Organic+Chemistry+%3A+IUPAC+Recommendations+and+Preferred+Names+2013+%28Blue+Book%29&rft.place=Cambridge&rft.pages=748&rft.pub=The+Royal+Society+of+Chemistry&rft.date=2014&rft_id=info%3Adoi%2F10.1039%2F9781849733069-00648&rft.isbn=978-0-85404-182-4&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALactic+acid" class="Z3988"></span></span> </li> <li id="cite_note-GESTIS-2"><span class="mw-cite-backlink">^ <a href="#cite_ref-GESTIS_2-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-GESTIS_2-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><a rel="nofollow" class="external text" href="https://gestis.dguv.de/data?name=013000&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-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-3">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFDawson1959" class="citation book cs1">Dawson RM, et al. 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"Determination of the pKa value of the hydroxyl group in the alpha-hydroxycarboxylates citrate, malate and lactate by 13C NMR: implications for metal coordination in biological systems". <i>Biometals</i>. <b>22</b> (5): 771–8. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2Fs10534-009-9224-5">10.1007/s10534-009-9224-5</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/19288211">19288211</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:11615864">11615864</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Biometals&rft.atitle=Determination+of+the+pKa+value+of+the+hydroxyl+group+in+the+alpha-hydroxycarboxylates+citrate%2C+malate+and+lactate+by+13C+NMR%3A+implications+for+metal+coordination+in+biological+systems&rft.volume=22&rft.issue=5&rft.pages=771-8&rft.date=2009-10&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A11615864%23id-name%3DS2CID&rft_id=info%3Apmid%2F19288211&rft_id=info%3Adoi%2F10.1007%2Fs10534-009-9224-5&rft.aulast=Silva&rft.aufirst=AM&rft.au=Kong%2C+X&rft.au=Hider%2C+RC&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALactic+acid" class="Z3988"></span></span> </li> <li id="cite_note-sigma-5"><span class="mw-cite-backlink">^ <a href="#cite_ref-sigma_5-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-sigma_5-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-sigma_5-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><a href="/wiki/Sigma-Aldrich" title="Sigma-Aldrich">Sigma-Aldrich Co.</a>, <a rel="nofollow" class="external text" href="https://www.sigmaaldrich.com/catalog/product/sial/69785"><span style="font-size:85%;">DL</span>-Lactic acid</a>. </span> </li> <li id="cite_note-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-6">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?printerFriendlyView=true&locale=null&chebiId=422&viewTermLineage=null&structureView=&">"(S)-lactic acid (CHEBI:422)"</a>. <i>www.ebi.ac.uk</i><span class="reference-accessdate">. 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title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Frontiers+in+Neuroenergetics&rft.atitle=Lactate+Effectively+Covers+Energy+Demands+during+Neuronal+Network+Activity+in+Neonatal+Hippocampal+Slices&rft.volume=3&rft.pages=2&rft.date=2011&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3092068%23id-name%3DPMC&rft_id=info%3Apmid%2F21602909&rft_id=info%3Adoi%2F10.3389%2Ffnene.2011.00002&rft.aulast=Ivanov&rft.aufirst=A&rft.au=Mukhtarov%2C+M&rft.au=Bregestovski%2C+P&rft.au=Zilberter%2C+Y&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3092068&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALactic+acid" class="Z3988"></span></span> </li> <li id="cite_note-38"><span class="mw-cite-backlink"><b><a href="#cite_ref-38">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKasischke2011" class="citation journal cs1">Kasischke K 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title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Frontiers+in+Neuroenergetics&rft.atitle=Lactate+fuels+the+neonatal+brain&rft.volume=3&rft.pages=4&rft.date=2011&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3108381%23id-name%3DPMC&rft_id=info%3Apmid%2F21687795&rft_id=info%3Adoi%2F10.3389%2Ffnene.2011.00004&rft.aulast=Kasischke&rft.aufirst=K&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3108381&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALactic+acid" class="Z3988"></span></span> </li> <li id="cite_note-bloodbook-39"><span class="mw-cite-backlink">^ <a href="#cite_ref-bloodbook_39-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-bloodbook_39-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-bloodbook_39-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-bloodbook_39-3"><sup><i><b>d</b></i></sup></a></span> <span class="reference-text"><a rel="nofollow" class="external text" href="http://www.bloodbook.com/ranges.html">Blood Test Results – Normal Ranges</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20121102092931/http://www.bloodbook.com/ranges.html">Archived</a> 2 November 2012 at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a> Bloodbook.Com</span> </li> <li id="cite_note-lactate-mass-40"><span class="mw-cite-backlink">^ <a href="#cite_ref-lactate-mass_40-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-lactate-mass_40-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-lactate-mass_40-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-lactate-mass_40-3"><sup><i><b>d</b></i></sup></a></span> <span class="reference-text">Derived from mass values using molar mass of 90.08 g/mol</span> </li> <li id="cite_note-41"><span class="mw-cite-backlink"><b><a href="#cite_ref-41">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCampieriCampieriBertuzziSwennen2001" class="citation journal cs1">Campieri, C.; Campieri, M.; Bertuzzi, V.; Swennen, E.; Matteuzzi, D.; Stefoni, S.; Pirovano, F.; Centi, C.; Ulisse, S.; Famularo, G.; De Simone, C. (September 2001). <a rel="nofollow" class="external text" href="https://doi.org/10.1046%2Fj.1523-1755.2001.0600031097.x">"Reduction of oxaluria after an oral course of lactic acid bacteria at high concentration"</a>. <i>Kidney International</i>. <b>60</b> (3): 1097–1105. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1046%2Fj.1523-1755.2001.0600031097.x">10.1046/j.1523-1755.2001.0600031097.x</a></span>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0085-2538">0085-2538</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/11532105">11532105</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Kidney+International&rft.atitle=Reduction+of+oxaluria+after+an+oral+course+of+lactic+acid+bacteria+at+high+concentration&rft.volume=60&rft.issue=3&rft.pages=1097-1105&rft.date=2001-09&rft.issn=0085-2538&rft_id=info%3Apmid%2F11532105&rft_id=info%3Adoi%2F10.1046%2Fj.1523-1755.2001.0600031097.x&rft.aulast=Campieri&rft.aufirst=C.&rft.au=Campieri%2C+M.&rft.au=Bertuzzi%2C+V.&rft.au=Swennen%2C+E.&rft.au=Matteuzzi%2C+D.&rft.au=Stefoni%2C+S.&rft.au=Pirovano%2C+F.&rft.au=Centi%2C+C.&rft.au=Ulisse%2C+S.&rft.au=Famularo%2C+G.&rft.au=De+Simone%2C+C.&rft_id=https%3A%2F%2Fdoi.org%2F10.1046%252Fj.1523-1755.2001.0600031097.x&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALactic+acid" class="Z3988"></span></span> </li> <li id="cite_note-42"><span class="mw-cite-backlink"><b><a href="#cite_ref-42">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.ars.usda.gov/sp2UserFiles/Place/80400525/Data/SR/SR28/sr28_doc.pdf">"USDA National Nutrient Database for Standard Reference, Release 28 (2015) Documentation and User Guide"</a> <span class="cs1-format">(PDF)</span>. 2015. p. 13.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=USDA+National+Nutrient+Database+for+Standard+Reference%2C+Release+28+%282015%29+Documentation+and+User+Guide&rft.pages=13&rft.date=2015&rft_id=http%3A%2F%2Fwww.ars.usda.gov%2Fsp2UserFiles%2FPlace%2F80400525%2FData%2FSR%2FSR28%2Fsr28_doc.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALactic+acid" class="Z3988"></span></span> </li> <li id="cite_note-43"><span class="mw-cite-backlink"><b><a href="#cite_ref-43">^</a></b></span> <span class="reference-text">For example, in <a rel="nofollow" class="external text" href="https://web.archive.org/web/20181116194139/https://ndb.nal.usda.gov/ndb/foods/show/105?n1=%7BQv%3D1%7D">this USDA database entry for yoghurt</a> the food energy is calculated using given coefficients for carbohydrate, fat, and protein. (One must click on "Full report" to see the coefficients.) The calculated value is based on 4.66 grams of carbohydrate, which is exactly equal to the sugars.</span> </li> <li id="cite_note-FAOSouthgate-44"><span class="mw-cite-backlink"><b><a href="#cite_ref-FAOSouthgate_44-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGreenfieldSouthgate2003" class="citation book cs1">Greenfield H, Southgate D (2003). <i>Food Composition Data: Production, Management and Use</i>. 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Archived from <a rel="nofollow" class="external text" href="http://www.purac.com/EN/Food/Markets/Meat_poultry_and_fish/Applications/Carcass.aspx">the original</a> on 29 July 2013<span class="reference-accessdate">. Retrieved <span class="nowrap">20 May</span> 2013</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Purac+Carcass+Applications&rft.pub=Purac&rft_id=http%3A%2F%2Fwww.purac.com%2FEN%2FFood%2FMarkets%2FMeat_poultry_and_fish%2FApplications%2FCarcass.aspx&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALactic+acid" class="Z3988"></span></span> </li> <li id="cite_note-53"><span class="mw-cite-backlink"><b><a href="#cite_ref-53">^</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.fda.gov/Food/IngredientsPackagingLabeling/GRAS/NoticeInventory/ucm153929.htm">"Agency Response Letter GRAS Notice No. GRN 000240"</a>. <i>FDA</i>. US FDA<span class="reference-accessdate">. Retrieved <span class="nowrap">20 May</span> 2013</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=FDA&rft.atitle=Agency+Response+Letter+GRAS+Notice+No.+GRN+000240&rft_id=https%3A%2F%2Fwww.fda.gov%2FFood%2FIngredientsPackagingLabeling%2FGRAS%2FNoticeInventory%2Fucm153929.htm&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALactic+acid" class="Z3988"></span></span> </li> <li id="cite_note-54"><span class="mw-cite-backlink"><b><a href="#cite_ref-54">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFDruckerman2016" class="citation news cs1">Druckerman P (2 October 2016). <a rel="nofollow" class="external text" href="https://www.nytimes.com/2016/10/02/opinion/sunday/if-i-sleep-for-an-hour-30-people-will-die.html">"If I Sleep for an Hour, 30 People Will Die"</a>. <i>The New York Times</i>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+New+York+Times&rft.atitle=If+I+Sleep+for+an+Hour%2C+30+People+Will+Die&rft.date=2016-10-02&rft.aulast=Druckerman&rft.aufirst=Pamela&rft_id=https%3A%2F%2Fwww.nytimes.com%2F2016%2F10%2F02%2Fopinion%2Fsunday%2Fif-i-sleep-for-an-hour-30-people-will-die.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALactic+acid" class="Z3988"></span></span> </li> <li id="cite_note-55"><span class="mw-cite-backlink"><b><a href="#cite_ref-55">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFNaushadLichtfouse2019" class="citation book cs1">Naushad, Mu.; Lichtfouse, Eric (2019). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=gBCTDwAAQBAJ"><i>Sustainable Agriculture Reviews 34: Date Palm for Food Medicine and the Environment</i></a>. Springer. p. 162. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-030-11345-2" title="Special:BookSources/978-3-030-11345-2"><bdi>978-3-030-11345-2</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Sustainable+Agriculture+Reviews+34%3A+Date+Palm+for+Food+Medicine+and+the+Environment&rft.pages=162&rft.pub=Springer&rft.date=2019&rft.isbn=978-3-030-11345-2&rft.aulast=Naushad&rft.aufirst=Mu.&rft.au=Lichtfouse%2C+Eric&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DgBCTDwAAQBAJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALactic+acid" class="Z3988"></span></span> </li> </ol></div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lactic_acid&action=edit&section=21" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a rel="nofollow" class="external text" href="http://www.smithsonianmag.com/science-nature/10022381.html">Corn Plastic to the Rescue</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20131121122758/http://www.smithsonianmag.com/science-nature/10022381.html">Archived</a> 21 November 2013 at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a></li> <li><a rel="nofollow" class="external text" href="http://www.webmd.com/a-to-z-guides/lactic-acid">Lactic Acid: Information and Resources</a></li> <li><a rel="nofollow" class="external text" href="https://www.nytimes.com/2006/05/16/health/nutrition/16run.html">Lactic Acid Is Not Muscles' Foe, It's Fuel</a></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFitzgerald2010" class="citation web cs1">Fitzgerald M (26 January 2010). <a rel="nofollow" class="external text" href="https://web.archive.org/web/20180825120642/http://running.competitor.com/2010/01/training/the-lactic-acid-myths_7938">"The Lactic Acid Myths"</a>. <i>Competitor Running</i>. Archived from <a rel="nofollow" class="external text" href="https://running.competitor.com/2010/01/training/the-lactic-acid-myths_7938">the original</a> on 25 August 2018.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Competitor+Running&rft.atitle=The+Lactic+Acid+Myths&rft.date=2010-01-26&rft.aulast=Fitzgerald&rft.aufirst=Matt&rft_id=http%3A%2F%2Frunning.competitor.com%2F2010%2F01%2Ftraining%2Fthe-lactic-acid-myths_7938&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALactic+acid" class="Z3988"></span></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 ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output .hlist.inline,.mw-parser-output .hlist.inline dl,.mw-parser-output .hlist.inline ol,.mw-parser-output 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href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Lactate_salts" style="display:table;;padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit;table-layout:fixed;"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Lactates" title="Template:Lactates"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Lactates" title="Template talk:Lactates"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Lactates" title="Special:EditPage/Template:Lactates"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Lactate_salts" style="font-size:114%;margin:0 4em">Lactate salts</div></th></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0;border-width:0;"><div style="padding:0"><div class="mw-collapsible-content" style="overflow-x:auto"> <table class="center"> <tbody><tr style="background-color:mistyrose"> <td><a class="mw-selflink selflink"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">6</sub>O<sub class="template-chem2-sub">3</sub></span></a> </td> <td style="background-color:white;border:none"> </td> <td style="background-color:white;border:none" colspan="11" rowspan="3"> </td> <td style="background-color:white;border:none" colspan="5"> </td> <td>He </td></tr> <tr style="background-color:mistyrose"> <td><a href="/wiki/Lithium_lactate" title="Lithium lactate"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">LiC<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">5</sub>O<sub class="template-chem2-sub">3</sub></span></a> </td> <td><a href="/w/index.php?title=Beryllium_lactate&action=edit&redlink=1" class="new" title="Beryllium lactate (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Be(C<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">5</sub>O<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">2</sub></span></a> </td> <td> </td> <td> </td> <td><a href="/wiki/Ammonium_lactate" title="Ammonium lactate"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">NH<sub class="template-chem2-sub">4</sub>C<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">5</sub>O<sub class="template-chem2-sub">3</sub></span></a> </td> <td><a href="/w/index.php?title=Lactic_anhydride&action=edit&redlink=1" class="new" title="Lactic anhydride (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">8</sub>O<sub class="template-chem2-sub">5</sub></span></a> </td> <td> </td> <td>Ne </td></tr> <tr style="background-color:mistyrose"> <td><a href="/wiki/Sodium_lactate" title="Sodium lactate"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">NaC<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">5</sub>O<sub class="template-chem2-sub">3</sub></span></a> </td> <td><a href="/wiki/Magnesium_lactate" title="Magnesium lactate"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Mg(C<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">5</sub>O<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">2</sub></span></a> </td> <td><a href="/wiki/Aluminium_lactate" title="Aluminium lactate"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Al(C<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">5</sub>O<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">3</sub></span></a> </td> <td> </td> <td> </td> <td> </td> <td> </td> <td>Ar </td></tr> <tr style="background-color:mistyrose"> <td><a href="/wiki/Potassium_lactate" title="Potassium lactate"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">KC<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">5</sub>O<sub class="template-chem2-sub">3</sub></span></a> </td> <td><a href="/wiki/Calcium_lactate" title="Calcium lactate"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Ca(C<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">5</sub>O<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">2</sub></span></a> </td> <td style="background-color:white;border:none"> </td> <td><a href="/w/index.php?title=Scandium_lactate&action=edit&redlink=1" class="new" title="Scandium lactate (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Sc(C<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">5</sub>O<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">3</sub></span></a> </td> <td><a href="/wiki/Titanium_tetralactate" title="Titanium tetralactate"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Ti(C<sub class="template-chem2-sub">12</sub>H<sub class="template-chem2-sub">20</sub>O<sub class="template-chem2-sub">12</sub>)</span></a> </td> <td><a href="/w/index.php?title=Vanadium(II)_lactate&action=edit&redlink=1" class="new" title="Vanadium(II) lactate (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">V(C<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">5</sub>O<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">2</sub></span></a><br /><a href="/w/index.php?title=Vanadium(III)_lactate&action=edit&redlink=1" class="new" title="Vanadium(III) lactate (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">V(C<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">5</sub>O<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">3</sub></span></a> </td> <td><a href="/w/index.php?title=Chromium(II)_lactate&action=edit&redlink=1" class="new" title="Chromium(II) lactate (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Cr(C<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">5</sub>O<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">2</sub></span></a><br /><a href="/w/index.php?title=Chromium(III)_lactate&action=edit&redlink=1" class="new" title="Chromium(III) lactate (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Cr(C<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">5</sub>O<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">3</sub></span></a> </td> <td><a href="/wiki/Manganese_lactate" title="Manganese lactate"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Mn(C<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">5</sub>O<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">2</sub></span></a> </td> <td><a href="/wiki/Iron(II)_lactate" title="Iron(II) lactate"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Fe(C<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">5</sub>O<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">2</sub></span></a><br /><a href="/w/index.php?title=Iron(III)_lactate&action=edit&redlink=1" class="new" title="Iron(III) lactate (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Fe(C<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">5</sub>O<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">3</sub></span></a> </td> <td><a href="/wiki/Cobalt_lactate" title="Cobalt lactate"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Co(C<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">5</sub>O<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">2</sub></span></a> </td> <td><a href="/w/index.php?title=Nickel(II)_lactate&action=edit&redlink=1" class="new" title="Nickel(II) lactate (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Ni(C<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">5</sub>O<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">2</sub></span></a> </td> <td><a href="/w/index.php?title=Copper(I)_lactate&action=edit&redlink=1" class="new" title="Copper(I) lactate (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CuC<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">5</sub>O<sub class="template-chem2-sub">3</sub></span></a><br /><a href="/wiki/Copper(II)_lactate" title="Copper(II) lactate"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Cu(C<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">5</sub>O<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">2</sub></span></a> </td> <td><a href="/wiki/Zinc_lactate" title="Zinc lactate"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Zn(C<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">5</sub>O<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">2</sub></span></a> </td> <td><a href="/w/index.php?title=Gallium(III)_lactate&action=edit&redlink=1" class="new" title="Gallium(III) lactate (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Ga(C<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">5</sub>O<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">3</sub></span></a> </td> <td> </td> <td> </td> <td> </td> <td> </td> <td>Kr </td></tr> <tr style="background-color:mistyrose"> <td><a href="/w/index.php?title=Rubidium_lactate&action=edit&redlink=1" class="new" title="Rubidium lactate (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">RbC<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">5</sub>O<sub class="template-chem2-sub">3</sub></span></a> </td> <td><a href="/wiki/Strontium_lactate" title="Strontium lactate"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Sr(C<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">5</sub>O<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">2</sub></span></a> </td> <td style="background-color:white;border:none"> </td> <td><a href="/w/index.php?title=Yttrium(III)_lactate&action=edit&redlink=1" class="new" title="Yttrium(III) lactate (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Y(C<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">5</sub>O<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">3</sub></span></a> </td> <td><a href="/wiki/Zirconium_lactate" title="Zirconium lactate"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Zr(C<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">5</sub>O<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">4</sub></span></a> </td> <td><a href="/w/index.php?title=Niobium(V)_lactate&action=edit&redlink=1" class="new" title="Niobium(V) lactate (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Nb(C<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">5</sub>O<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">5</sub></span></a> </td> <td><a href="/w/index.php?title=Molybdenum(II)_lactate&action=edit&redlink=1" class="new" title="Molybdenum(II) lactate (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Mo(C<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">5</sub>O<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">2</sub></span></a><br /><a href="/w/index.php?title=Molybdenum(III)_lactate&action=edit&redlink=1" class="new" title="Molybdenum(III) lactate (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Mo(C<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">5</sub>O<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">3</sub></span></a><br /><a href="/w/index.php?title=Molybdenum(IV)_lactate&action=edit&redlink=1" class="new" title="Molybdenum(IV) lactate (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Mo(C<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">5</sub>O<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">4</sub></span></a> </td> <td><a href="/w/index.php?title=Technetium(IV)_lactate&action=edit&redlink=1" class="new" title="Technetium(IV) lactate (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Tc(C<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">5</sub>O<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">4</sub></span></a> </td> <td><a href="/w/index.php?title=Ruthenium(III)_lactate&action=edit&redlink=1" class="new" title="Ruthenium(III) lactate (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Ru(C<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">5</sub>O<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">3</sub></span></a> </td> <td><a href="/w/index.php?title=Rhodium(III)_lactate&action=edit&redlink=1" class="new" title="Rhodium(III) lactate (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Rh(C<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">5</sub>O<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">3</sub></span></a> </td> <td><a href="/w/index.php?title=Palladium(II)_lactate&action=edit&redlink=1" class="new" title="Palladium(II) lactate (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Pd(C<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">5</sub>O<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">2</sub></span></a> </td> <td><a href="/wiki/Silver_lactate" title="Silver lactate"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">AgC<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">5</sub>O<sub class="template-chem2-sub">3</sub></span></a> </td> <td><a href="/wiki/Cadmium_lactate" title="Cadmium lactate"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Cd(C<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">5</sub>O<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">2</sub></span></a> </td> <td><a href="/w/index.php?title=Indium(III)_lactate&action=edit&redlink=1" class="new" title="Indium(III) lactate (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">In(C<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">5</sub>O<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">3</sub></span></a> </td> <td><a href="/w/index.php?title=Tin(II)_lactate&action=edit&redlink=1" class="new" title="Tin(II) lactate (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Sn(C<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">5</sub>O<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">2</sub></span></a> </td> <td> </td> <td> </td> <td> </td> <td> </td></tr> <tr style="background-color:mistyrose"> <td><a href="/w/index.php?title=Caesium_lactate&action=edit&redlink=1" class="new" title="Caesium lactate (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CsC<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">5</sub>O<sub class="template-chem2-sub">3</sub></span></a> </td> <td><a href="/w/index.php?title=Barium_lactate&action=edit&redlink=1" class="new" title="Barium lactate (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Ba(C<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">5</sub>O<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">2</sub></span></a> </td> <td style="background-color:white;border:none">* </td> <td><a href="/w/index.php?title=Lutetium(III)_lactate&action=edit&redlink=1" class="new" title="Lutetium(III) lactate (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Lu(C<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">5</sub>O<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">3</sub></span></a> </td> <td><a href="/w/index.php?title=Hafnium_tetralactate&action=edit&redlink=1" class="new" title="Hafnium tetralactate (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Hf(C<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">5</sub>O<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">4</sub></span></a> </td> <td> </td> <td> </td> <td> </td> <td> </td> <td> </td> <td><a href="/w/index.php?title=Platinum(II)_lactate&action=edit&redlink=1" class="new" title="Platinum(II) lactate (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Pt(C<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">5</sub>O<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">2</sub></span></a> </td> <td> </td> <td><a href="/w/index.php?title=Mercury(I)_lactate&action=edit&redlink=1" class="new" title="Mercury(I) lactate (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Hg<sub class="template-chem2-sub">2</sub>(C<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">5</sub>O<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">2</sub></span></a><br /> <a href="/w/index.php?title=Mercury(II)_lactate&action=edit&redlink=1" class="new" title="Mercury(II) lactate (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Hg(C<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">5</sub>O<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">2</sub></span></a> </td> <td><a href="/w/index.php?title=Thallium(I)_lactate&action=edit&redlink=1" class="new" title="Thallium(I) lactate (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">TlC<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">5</sub>O<sub class="template-chem2-sub">3</sub></span></a> </td> <td><a href="/w/index.php?title=Lead(II)_lactate&action=edit&redlink=1" class="new" title="Lead(II) lactate (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Pb(C<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">5</sub>O<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">2</sub></span></a> </td> <td> </td> <td> </td> <td> </td> <td>Rn </td></tr> <tr style="background-color:mistyrose"> <td>Fr </td> <td><a href="/w/index.php?title=Radium_lactate&action=edit&redlink=1" class="new" title="Radium lactate (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Ra(C<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">5</sub>O<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">2</sub></span></a> </td> <td style="background-color:white;border:none">** </td> <td>Lr </td> <td>Rf </td> <td>Db </td> <td>Sg </td> <td>Bh </td> <td>Hs </td> <td>Mt </td> <td>Ds </td> <td>Rg </td> <td>Cn </td> <td>Nh </td> <td>Fl </td> <td>Mc </td> <td>Lv </td> <td>Ts </td> <td>Og </td></tr> <tr> <td style="background-color:white;border:none" colspan="2" rowspan="3"> </td> <td style="background-color:white;border:none" colspan="20">  </td></tr> <tr style="background-color:mistyrose"> <td style="background-color:white;border:none">* </td> <td><a href="/w/index.php?title=Lanthanum(III)_lactate&action=edit&redlink=1" class="new" title="Lanthanum(III) lactate (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">La(C<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">5</sub>O<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">3</sub></span></a> </td> <td><a href="/w/index.php?title=Cerium(III)_lactate&action=edit&redlink=1" class="new" title="Cerium(III) lactate (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Ce(C<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">5</sub>O<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">3</sub></span></a> </td> <td><a href="/w/index.php?title=Praseodymium(III)_lactate&action=edit&redlink=1" class="new" title="Praseodymium(III) lactate (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Pr(C<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">5</sub>O<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">3</sub></span></a> </td> <td><a href="/w/index.php?title=Neodymium(III)_lactate&action=edit&redlink=1" class="new" title="Neodymium(III) lactate (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Nd(C<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">5</sub>O<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">3</sub></span></a> </td> <td>Pm </td> <td><a href="/w/index.php?title=Samarium(III)_lactate&action=edit&redlink=1" class="new" title="Samarium(III) lactate (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Sm(C<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">5</sub>O<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">3</sub></span></a> </td> <td><a href="/w/index.php?title=Europium(III)_lactate&action=edit&redlink=1" class="new" title="Europium(III) lactate (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Eu(C<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">5</sub>O<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">3</sub></span></a> </td> <td><a href="/w/index.php?title=Gadolinium(III)_lactate&action=edit&redlink=1" class="new" title="Gadolinium(III) lactate (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Gd(C<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">5</sub>O<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">3</sub></span></a> </td> <td><a href="/w/index.php?title=Terbium(III)_lactate&action=edit&redlink=1" class="new" title="Terbium(III) lactate (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Tb(C<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">5</sub>O<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">3</sub></span></a> </td> <td><a href="/w/index.php?title=Dyprosmium(III)_lactate&action=edit&redlink=1" class="new" title="Dyprosmium(III) lactate (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Dy(C<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">5</sub>O<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">3</sub></span></a> </td> <td><a href="/w/index.php?title=Holmium(III)_lactate&action=edit&redlink=1" class="new" title="Holmium(III) lactate (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Ho(C<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">5</sub>O<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">3</sub></span></a> </td> <td><a href="/w/index.php?title=Erbium(III)_lactate&action=edit&redlink=1" class="new" title="Erbium(III) lactate (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Er(C<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">5</sub>O<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">3</sub></span></a> </td> <td><a href="/w/index.php?title=Thulium(III)_lactate&action=edit&redlink=1" class="new" title="Thulium(III) lactate (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Tm(C<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">5</sub>O<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">3</sub></span></a> </td> <td><a href="/w/index.php?title=Ytterbium(III)_lactate&action=edit&redlink=1" class="new" title="Ytterbium(III) lactate (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Yb(C<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">5</sub>O<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">3</sub></span></a> </td></tr> <tr style="background-color:mistyrose"> <td style="background-color:white;border:none">** </td> <td><a href="/w/index.php?title=Actinium(III)_lactate&action=edit&redlink=1" class="new" title="Actinium(III) lactate (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Ac(C<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">5</sub>O<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">3</sub></span></a> </td> <td><a href="/w/index.php?title=Thorium(IV)_lactate&action=edit&redlink=1" class="new" title="Thorium(IV) lactate (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Th(C<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">5</sub>O<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">4</sub></span></a> </td> <td><a href="/w/index.php?title=Protactinium(V)_lactate&action=edit&redlink=1" class="new" title="Protactinium(V) lactate (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Pa(C<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">5</sub>O<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">5</sub></span></a> </td> <td><a href="/w/index.php?title=Uranium_tetralactate&action=edit&redlink=1" class="new" title="Uranium tetralactate (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">U(C<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">5</sub>O<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">4</sub></span></a><br /><a href="/w/index.php?title=Uranium_pentalactate&action=edit&redlink=1" class="new" title="Uranium pentalactate (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">U(C<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">5</sub>O<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">5</sub></span></a> </td> <td><a href="/w/index.php?title=Neptunium(IV)_lactate&action=edit&redlink=1" class="new" title="Neptunium(IV) lactate (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Np(C<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">5</sub>O<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">4</sub></span></a> </td> <td><a href="/w/index.php?title=Plutonium(III)_lactate&action=edit&redlink=1" class="new" title="Plutonium(III) lactate (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Pu(C<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">5</sub>O<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">3</sub></span></a> </td> <td> </td> <td> </td> <td>Bk </td> <td> </td> <td> </td> <td>Fm </td> <td>Md </td> <td>No </td></tr></tbody></table></div> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"><style data-mw-deduplicate="TemplateStyles:r1038841319">.mw-parser-output .tooltip-dotted{border-bottom:1px dotted;cursor:help}</style><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1038841319"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1038841319"></div><div role="navigation" class="navbox authority-control" aria-label="Navbox" 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