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<span>Stereochemistry</span> </div> </a> <ul id="toc-Stereochemistry-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Production" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Production"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Production</span> </div> </a> <button aria-controls="toc-Production-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Production subsection</span> </button> <ul id="toc-Production-sublist" class="vector-toc-list"> <li id="toc-L-(+)-Tartaric_acid" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#L-(+)-Tartaric_acid"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.1</span> <span>L-(+)-Tartaric acid</span> </div> </a> <ul id="toc-L-(+)-Tartaric_acid-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Racemic_tartaric_acid" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Racemic_tartaric_acid"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.2</span> <span>Racemic tartaric acid</span> </div> </a> <ul id="toc-Racemic_tartaric_acid-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-meso-Tartaric_acid" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#meso-Tartaric_acid"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.3</span> <span><i>meso</i>-Tartaric acid</span> </div> </a> <ul id="toc-meso-Tartaric_acid-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Reactivity" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Reactivity"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Reactivity</span> </div> </a> <ul id="toc-Reactivity-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Derivatives" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Derivatives"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Derivatives</span> </div> </a> <ul id="toc-Derivatives-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Tartaric_acid_in_wine" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Tartaric_acid_in_wine"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Tartaric acid in wine</span> </div> </a> <ul id="toc-Tartaric_acid_in_wine-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Tartaric_acid_in_fruits" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Tartaric_acid_in_fruits"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Tartaric acid in fruits</span> </div> </a> <ul id="toc-Tartaric_acid_in_fruits-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Applications" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Applications"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>Applications</span> </div> </a> <ul id="toc-Applications-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Toxicity_in_canines" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Toxicity_in_canines"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>Toxicity in canines</span> </div> </a> <ul id="toc-Toxicity_in_canines-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">10</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">11</span> <span>External links</span> </div> </a> <ul id="toc-External_links-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" title="Table of Contents" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" 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Available in 53 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-53" 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">53 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%D8%B7%D8%B1%D8%B7%D8%B1%D9%8A%D9%83" title="حمض الطرطريك – Arabic" lang="ar" hreflang="ar" data-title="حمض الطرطريك" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-az mw-list-item"><a href="https://az.wikipedia.org/wiki/%C3%87ax%C4%B1r_tur%C5%9Fusu" title="Çaxır turşusu – Azerbaijani" lang="az" hreflang="az" data-title="Çaxır turşusu" data-language-autonym="Azərbaycanca" data-language-local-name="Azerbaijani" class="interlanguage-link-target"><span>Azərbaycanca</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D8%A7%D8%B3%DB%8C%D8%AF_%D8%AA%D8%A7%D8%B1%D8%AA%D8%A7%D8%B1%DB%8C%DA%A9" title="اسید تارتاریک – South Azerbaijani" lang="azb" hreflang="azb" data-title="اسید تارتاریک" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%92%D0%B8%D0%BD%D0%B5%D0%BD%D0%B0_%D0%BA%D0%B8%D1%81%D0%B5%D0%BB%D0%B8%D0%BD%D0%B0" title="Винена киселина – Bulgarian" lang="bg" hreflang="bg" data-title="Винена 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/Vinska_kiselina" title="Vinska kiselina – Bosnian" lang="bs" hreflang="bs" data-title="Vinska 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_t%C3%A0rtric" title="Àcid tàrtric – Catalan" lang="ca" hreflang="ca" data-title="Àcid tàrtric" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Kyselina_vinn%C3%A1" title="Kyselina vinná – Czech" lang="cs" hreflang="cs" data-title="Kyselina vinná" 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_tartarig" title="Asid tartarig – Welsh" lang="cy" hreflang="cy" data-title="Asid tartarig" 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/Vinsyre" title="Vinsyre – Danish" lang="da" hreflang="da" data-title="Vinsyre" 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/Weins%C3%A4ure" title="Weinsäure – German" lang="de" hreflang="de" data-title="Weinsäure" 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/Viinhape" title="Viinhape – Estonian" lang="et" hreflang="et" data-title="Viinhape" 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%A4%CF%81%CF%85%CE%B3%CE%B9%CE%BA%CF%8C_%CE%BF%CE%BE%CF%8D" title="Τρυγικό οξύ – Greek" lang="el" hreflang="el" data-title="Τρυγικό 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_tart%C3%A1rico" title="Ácido tartárico – Spanish" lang="es" hreflang="es" data-title="Ácido tartárico" 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/Tartrata_acido" title="Tartrata acido – Esperanto" lang="eo" hreflang="eo" data-title="Tartrata 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_tartariko" title="Azido tartariko – Basque" lang="eu" hreflang="eu" data-title="Azido tartariko" 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%AA%D8%A7%D8%B1%D8%AA%D8%A7%D8%B1%DB%8C%DA%A9_%D8%A7%D8%B3%DB%8C%D8%AF" title="تارتاریک اسید – Persian" lang="fa" hreflang="fa" data-title="تارتاریک اسید" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Acide_tartrique" title="Acide tartrique – French" lang="fr" hreflang="fr" data-title="Acide tartrique" 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_tartarach" title="Aigéad tartarach – Irish" lang="ga" hreflang="ga" data-title="Aigéad tartarach" 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_tart%C3%A1rico" title="Ácido tartárico – Galician" lang="gl" hreflang="gl" data-title="Ácido tartárico" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%ED%83%80%ED%83%80%EB%A5%B4%EC%82%B0" title="타타르산 – Korean" lang="ko" hreflang="ko" data-title="타타르산" 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%B3%D5%AB%D5%B6%D5%A5%D5%A9%D5%A9%D5%B8%D6%82" title="Գինեթթու – Armenian" lang="hy" hreflang="hy" data-title="Գինեթթու" 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%9F%E0%A4%BE%E0%A4%B0%E0%A5%8D%E0%A4%9F%E0%A4%B0%E0%A4%BF%E0%A4%95_%E0%A4%85%E0%A4%AE%E0%A5%8D%E0%A4%B2" title="टार्टरिक अम्ल – Hindi" lang="hi" hreflang="hi" data-title="टार्टरिक 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/Vinska_kiselina" title="Vinska kiselina – Croatian" lang="hr" hreflang="hr" data-title="Vinska 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_tartrat" title="Asam tartrat – Indonesian" lang="id" hreflang="id" data-title="Asam tartrat" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target"><span>Bahasa Indonesia</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Acido_tartarico" title="Acido tartarico – Italian" lang="it" hreflang="it" data-title="Acido tartarico" 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%98%D7%A8%D7%98%D7%A8%D7%99%D7%AA" title="חומצה טרטרית – Hebrew" lang="he" hreflang="he" data-title="חומצה טרטרית" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-kk mw-list-item"><a href="https://kk.wikipedia.org/wiki/%D0%A2%D0%B0%D1%80%D1%82%D0%B0%D1%80_%D2%9B%D1%8B%D1%88%D2%9B%D1%8B%D0%BB%D1%8B" title="Тартар қышқылы – Kazakh" lang="kk" hreflang="kk" data-title="Тартар қышқылы" data-language-autonym="Қазақша" data-language-local-name="Kazakh" class="interlanguage-link-target"><span>Қазақша</span></a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/V%C4%ABnsk%C4%81be" title="Vīnskābe – Latvian" lang="lv" hreflang="lv" data-title="Vīnskābe" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target"><span>Latviešu</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Bork%C5%91sav" title="Borkősav – Hungarian" lang="hu" hreflang="hu" data-title="Borkősav" 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%92%D0%B8%D0%BD%D1%81%D0%BA%D0%B0_%D0%BA%D0%B8%D1%81%D0%B5%D0%BB%D0%B8%D0%BD%D0%B0" title="Винска киселина – Macedonian" lang="mk" hreflang="mk" data-title="Винска 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%9F%E0%B4%BE%E0%B5%BC%E0%B4%9F%E0%B5%8D%E0%B4%9F%E0%B4%BE%E0%B4%B1%E0%B4%BF%E0%B4%95%E0%B5%8D_%E0%B4%85%E0%B4%AE%E0%B5%8D%E0%B4%B2%E0%B4%82" title="ടാർട്ടാറിക് അമ്ലം – Malayalam" lang="ml" hreflang="ml" data-title="ടാർട്ടാറിക് അമ്ലം" 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_tartarik" title="Asid tartarik – Malay" lang="ms" hreflang="ms" data-title="Asid tartarik" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" class="interlanguage-link-target"><span>Bahasa Melayu</span></a></li><li class="interlanguage-link interwiki-my mw-list-item"><a href="https://my.wikipedia.org/wiki/%E1%80%90%E1%80%AC%E1%80%90%E1%80%AC%E1%80%9B%E1%80%85%E1%80%BA_%E1%80%A1%E1%80%80%E1%80%BA%E1%80%86%E1%80%85%E1%80%BA" title="တာတာရစ် အက်ဆစ် – Burmese" lang="my" hreflang="my" data-title="တာတာရစ် အက်ဆစ်" data-language-autonym="မြန်မာဘာသာ" data-language-local-name="Burmese" class="interlanguage-link-target"><span>မြန်မာဘာသာ</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Wijnsteenzuur" title="Wijnsteenzuur – Dutch" lang="nl" hreflang="nl" data-title="Wijnsteenzuur" 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/%E9%85%92%E7%9F%B3%E9%85%B8" title="酒石酸 – Japanese" lang="ja" hreflang="ja" data-title="酒石酸" 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-uz mw-list-item"><a href="https://uz.wikipedia.org/wiki/Vino_kislota" title="Vino kislota – Uzbek" lang="uz" hreflang="uz" data-title="Vino 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_winowy" title="Kwas winowy – Polish" lang="pl" hreflang="pl" data-title="Kwas winowy" 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_tart%C3%A1rico" title="Ácido tartárico – Portuguese" lang="pt" hreflang="pt" 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</nav> </div> </div> </div> <div class="vector-column-end"> <div class="vector-sticky-pinned-container"> <nav class="vector-page-tools-landmark" aria-label="Page tools"> <div id="vector-page-tools-pinned-container" class="vector-pinned-container"> </div> </nav> <nav class="vector-appearance-landmark" aria-label="Appearance"> <div id="vector-appearance-pinned-container" class="vector-pinned-container"> <div id="vector-appearance" class="vector-appearance vector-pinnable-element"> <div class="vector-pinnable-header vector-appearance-pinnable-header 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" 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.ib-chembox td,.mw-parser-output .ib-chembox th{border:1px solid #a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}</style> <table class="infobox ib-chembox"> <caption>Tartaric acid<sup id="cite_ref-pubchem_1-0" class="reference"><a href="#cite_note-pubchem-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><figure class="mw-halign-center skin-invert-image" typeof="mw:File"><a href="/wiki/File:Tartaric_acid.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/05/Tartaric_acid.svg/220px-Tartaric_acid.svg.png" decoding="async" width="220" height="129" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/05/Tartaric_acid.svg/330px-Tartaric_acid.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/05/Tartaric_acid.svg/440px-Tartaric_acid.svg.png 2x" data-file-width="625" data-file-height="366" /></a><figcaption></figcaption></figure> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Tartaric-acid-3D-balls.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/72/Tartaric-acid-3D-balls.png/220px-Tartaric-acid-3D-balls.png" decoding="async" width="220" height="130" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/72/Tartaric-acid-3D-balls.png/330px-Tartaric-acid-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/72/Tartaric-acid-3D-balls.png/440px-Tartaric-acid-3D-balls.png 2x" data-file-width="1100" data-file-height="650" /></a><figcaption></figcaption></figure><div style="text-align:center;">Ball-and-stick model of <small>L</small>-(+)-tartaric acid</div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Chemical_nomenclature" title="Chemical nomenclature">IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">Tartaric acid<sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup></div> </td></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Preferred_IUPAC_name" title="Preferred IUPAC name">Preferred IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;">2,3-Dihydroxybutanedioic acid</div></div> </td></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Chemical_nomenclature#Systematic_name" title="Chemical nomenclature">Systematic IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;">(2<i>R</i>, 3<i>R</i>)-Threaric acid (+)<br />(2<i>S</i>, 3<i>S</i>)-Threaric acid (-)<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><br /><i>meso</i>-Erythraric acid<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></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;">Tartaric acid<br />2,3-Dihydroxysuccinic acid<br />Threaric acid<br />Racemic acid<br />Uvic acid<br />Paratartaric acid<br />Winestone</div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li>R,R-isomer: <span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=87-69-4">87-69-4</a></span></li><li>S,S-isomer: <span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=147-71-7">147-71-7</a></span></li><li>racemic: <span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=133-37-9">133-37-9</a></span></li><li>meso-isomer: <span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=147-73-9">147-73-9</a></span></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=O%3DC%28O%29C%28O%29C%28O%29C%28%3DO%29O">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=15674">CHEBI:15674</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembl/explore/compound/ChEMBL333714">ChEMBL333714</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="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembl/explore/compound/ChEMBL1200861">ChEMBL1200861</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.852.html">852</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/DrugBank" title="DrugBank">DrugBank</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.drugbank.ca"><a rel="nofollow" class="external text" href="https://www.drugbank.ca/drugs/DB01694">DB01694</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/100.121.903">100.121.903</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q194322#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/E_number" title="E number"><span title="E number (food additive code)">E number</span></a> </td> <td>E334 <a href="/wiki/E_number#E300–E399" title="E number">(antioxidants, ...)</a> </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/C00898">C00898</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/Medical_Subject_Headings" title="Medical Subject Headings">MeSH</a> </td> <td><span title="www.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://www.nlm.nih.gov/cgi/mesh/2014/MB_cgi?mode=&term=tartaric+acid">tartaric+acid</a></span> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/875">875</a></span> unspecified isomer</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/W4888I119H">W4888I119H</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID5046986,">DTXSID501031477 DTXSID5046986, DTXSID501031477</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q194322#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></span></li></ul></div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/C4H6O6/c5-1(3(7)8)2(6)4(9)10/h1-2,5-6H,(H,7,8)(H,9,10)<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: FEWJPZIEWOKRBE-UHFFFAOYSA-N<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div></div></li><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1/C4H6O6/c5-1(3(7)8)2(6)4(9)10/h1-2,5-6H,(H,7,8)(H,9,10)</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: FEWJPZIEWOKRBE-UHFFFAOYAZ</div></div></li></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">O=C(O)C(O)C(O)C(=O)O</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td>C<sub>4</sub>H<sub>6</sub>O<sub>6</sub> (basic formula)<br />HO<sub>2</sub>CCH(OH)CH(OH)CO<sub>2</sub>H (structural formula)  </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td>150.087<span class="nowrap"> </span>g/mol    </td></tr> <tr> <td>Appearance </td> <td>White powder </td></tr> <tr> <td><a href="/wiki/Density" title="Density">Density</a> </td> <td>1.737 g/cm<sup>3</sup> (R,R- and S,S-)<br />1.79 g/cm<sup>3</sup> (racemate)<br />1.886 g/cm<sup>3</sup> (meso) </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>169, 172 °C (R,R- and S,S-)<br />206 °C (racemate)<br />165-6 °C (meso) </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Aqueous_solution" title="Aqueous solution">Solubility in water</a></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>1.33<span class="nowrap"> </span>kg/L (<i>L or D</i>-tartaric)</li><li>0.21<span class="nowrap"> </span>kg/L (<i>DL</i>, racemic)</li><li>1.25<span class="nowrap"> </span>kg/L ("meso")</li></ul></div> </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>L(+) 25<span class="nowrap"> </span>°C :<br />pK<sub>a1</sub>= 2.89, pK<sub>a2</sub>= 4.40<br />meso 25<span class="nowrap"> </span>°C:<br />pK<sub>a1</sub>= 3.22, pK<sub>a2</sub>= 4.85 <p><sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> </td></tr> <tr> <td><a href="/wiki/Conjugate_base" class="mw-redirect" title="Conjugate base">Conjugate base</a> </td> <td><a href="/wiki/Bitartrate" title="Bitartrate">Bitartrate</a> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Magnetic_susceptibility" title="Magnetic susceptibility">Magnetic susceptibility</a> (χ)</div> </td> <td>−67.5·10<sup>−6</sup> cm<sup>3</sup>/mol </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Hazards </th></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;color:inherit;"><a href="/wiki/Globally_Harmonized_System_of_Classification_and_Labelling_of_Chemicals" title="Globally Harmonized System of Classification and Labelling of Chemicals"><b>GHS</b> labelling</a>:<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td 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> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Globally_Harmonized_System_of_Classification_and_Labelling_of_Chemicals#Signal_word" title="Globally Harmonized System of Classification and Labelling of Chemicals">Signal word</a></div> </td> <td><b>Danger</b> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_hazard_statements" title="GHS hazard statements">Hazard statements</a></div> </td> <td><abbr class="abbr" title="H318: Causes serious eye damage">H318</abbr> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_precautionary_statements" title="GHS precautionary statements">Precautionary statements</a></div> </td> <td><abbr class="abbr" title="P280: Wear protective gloves/protective clothing/eye protection/face protection.">P280</abbr>, <abbr class="abbr" title="P305+P351+P338+P310: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do. Continue rinsing. Immediately call a POISON CENTER or doctor/physician.">P305+P351+P338+P310</abbr> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Related compounds </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Other <a href="/wiki/Ion" title="Ion">cations</a></div> </td> <td><a href="/wiki/Monosodium_tartrate" title="Monosodium tartrate">Monosodium tartrate</a><br /><a href="/wiki/Sodium_tartrate" title="Sodium tartrate">Disodium tartrate</a><br /><a href="/wiki/Potassium_bitartrate" title="Potassium bitartrate">Monopotassium tartrate</a><br /><a href="/wiki/Potassium_tartrate" title="Potassium tartrate">Dipotassium tartrate</a> </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><a href="/wiki/Butyric_acid" title="Butyric acid">Butyric acid</a><br /><a href="/wiki/Succinic_acid" title="Succinic acid">Succinic acid</a><br /><a href="/wiki/Dimercaptosuccinic_acid" class="mw-redirect" title="Dimercaptosuccinic acid">Dimercaptosuccinic acid</a><br /><a href="/wiki/Malic_acid" title="Malic acid">Malic acid</a><br /><a href="/wiki/Maleic_acid" title="Maleic acid">Maleic acid</a><br /><a href="/wiki/Fumaric_acid" title="Fumaric acid">Fumaric acid</a> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Related compounds</div> </td> <td><a href="/wiki/2,3-Butanediol" title="2,3-Butanediol">2,3-Butanediol</a><br /><a href="/wiki/Cichoric_acid" class="mw-redirect" title="Cichoric acid">Cichoric acid</a> </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; color:inherit; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"><div style="text-align:center;"><span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/12px-Yes_check.svg.png" decoding="async" width="12" height="12" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/18px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/24px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span> <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=476994374&page2=Tartaric+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>Tartaric acid</b> is a white, crystalline <a href="/wiki/Organic_acid" title="Organic acid">organic acid</a> that occurs naturally in many fruits, most notably in <a href="/wiki/Grape" title="Grape">grapes</a> but also in <a href="/wiki/Tamarind" title="Tamarind">tamarinds</a>, <a href="/wiki/Banana" title="Banana">bananas</a>, <a href="/wiki/Avocado" title="Avocado">avocados</a>, and <a href="/wiki/Citrus" title="Citrus">citrus</a>.<sup id="cite_ref-pubchem_1-1" class="reference"><a href="#cite_note-pubchem-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Its <a href="/wiki/Salt_(chemistry)" title="Salt (chemistry)">salt</a>, <a href="/wiki/Potassium_bitartrate" title="Potassium bitartrate">potassium bitartrate</a>, commonly known as cream of tartar, develops naturally in the process of <a href="/wiki/Winemaking" title="Winemaking">fermentation</a>. Potassium bitartrate is commonly mixed with <a href="/wiki/Sodium_bicarbonate" title="Sodium bicarbonate">sodium bicarbonate</a> and is sold as <a href="/wiki/Baking_powder" title="Baking powder">baking powder</a> used as a <a href="/wiki/Leavening_agent" title="Leavening agent">leavening agent</a> in food preparation. The acid itself is added to foods as an <a href="/wiki/Antioxidant" title="Antioxidant">antioxidant</a> <a href="/wiki/E-numbers" class="mw-redirect" title="E-numbers">E334</a> and to impart its distinctive sour taste. <a href="/wiki/Naturally_occurring" class="mw-redirect" title="Naturally occurring">Naturally occurring</a> tartaric acid is a useful raw material in <a href="/wiki/Organic_synthesis" title="Organic synthesis">organic synthesis</a>. Tartaric acid, an alpha-hydroxy-<a href="/wiki/Carboxylic_acid" title="Carboxylic acid">carboxylic acid</a>, is <a href="/wiki/Diprotic_acid" class="mw-redirect" title="Diprotic acid">diprotic</a> and <a href="/wiki/Aldaric_acid" title="Aldaric acid">aldaric</a> in acid characteristics and is a dihydroxyl derivative of <a href="/wiki/Succinic_acid" title="Succinic acid">succinic acid</a>. </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=Tartaric_acid&action=edit&section=1" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Tartaric acid has been known to <a href="/wiki/Winemakers" class="mw-redirect" title="Winemakers">winemakers</a> for centuries. However, the chemical process for extraction was developed in 1769 by the <a href="/wiki/Sweden" title="Sweden">Swedish</a> chemist <a href="/wiki/Carl_Wilhelm_Scheele" title="Carl Wilhelm Scheele">Carl Wilhelm Scheele</a>.<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p><p>Tartaric acid played an important role in the discovery of <a href="/wiki/Chirality_(chemistry)" title="Chirality (chemistry)">chemical chirality</a>. This property of tartaric acid was first observed in 1832 by <a href="/wiki/Jean_Baptiste_Biot" class="mw-redirect" title="Jean Baptiste Biot">Jean Baptiste Biot</a>, who observed its ability to rotate <a href="/wiki/Polarization_(waves)" title="Polarization (waves)">polarized light</a>.<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup><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> <a href="/wiki/Louis_Pasteur" title="Louis Pasteur">Louis Pasteur</a> continued this research in 1847 by investigating the shapes of <a href="/wiki/Sodium_ammonium_tartrate" title="Sodium ammonium tartrate">sodium ammonium tartrate</a> crystals, which he found to be chiral. By manually sorting the differently shaped crystals, Pasteur was the first to produce a pure sample of levotartaric acid.<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup><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-Flack_14-0" class="reference"><a href="#cite_note-Flack-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Stereochemistry">Stereochemistry</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tartaric_acid&action=edit&section=2" title="Edit section: Stereochemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size mw-halign-left skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:TartrateCrystal.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/24/TartrateCrystal.svg/220px-TartrateCrystal.svg.png" decoding="async" width="220" height="220" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/24/TartrateCrystal.svg/330px-TartrateCrystal.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/24/TartrateCrystal.svg/440px-TartrateCrystal.svg.png 2x" data-file-width="700" data-file-height="700" /></a><figcaption>Tartaric acid crystals drawn as if seen through an <a href="/wiki/Optical_microscope" title="Optical microscope">optical microscope</a></figcaption></figure> <p>Naturally occurring form of the acid is <b>dextro tartaric acid </b> or <b><small>L</small>-(+)-tartaric acid</b> (obsolete name <a href="/wiki/Descriptor_(Chemistry)#dl" class="mw-redirect" title="Descriptor (Chemistry)"><i>d</i></a>-tartaric acid). Because it is available naturally, it is cheaper than its <a href="/wiki/Enantiomer" title="Enantiomer">enantiomer</a> and the <a href="/wiki/Meso_isomer" class="mw-redirect" title="Meso isomer">meso isomer</a>. The <i>dextro</i> and <i>levo</i> prefixes are archaic terms.<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> Modern textbooks refer to the natural form as (2<i>R</i>,3<i>R</i>)-tartaric acid <b>(</b><small>L</small><b>-(+)-tartaric acid)</b>, and its enantiomer as (2<i>S</i>,3<i>S</i>)-tartaric acid <b>(</b>D<b>-(-)-tartaric acid)</b>. The <i>meso</i> diastereomer is referred to as (2<i>R</i>,3<i>S</i>)-tartaric acid or (2<i>S</i>,3<i>R</i>)-tartaric acid. </p> <ul><li>Dextro and levo form <a href="/wiki/Crystal_structure" title="Crystal structure">monoclinic sphenoidal</a> crystals<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> and <a href="/wiki/Orthorhombic" class="mw-redirect" title="Orthorhombic">orthorhombic</a> crystals.</li> <li>Racemic tartaric acid forms <a href="/wiki/Monoclinic" class="mw-redirect" title="Monoclinic">monoclinic</a><sup id="cite_ref-CRC49_17-0" class="reference"><a href="#cite_note-CRC49-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> and <a href="/wiki/Triclinic" class="mw-redirect" title="Triclinic">triclinic</a> crystals (<a href="/wiki/Space_group" title="Space group">space group</a> P<span style="text-decoration:overline;">1</span>).<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><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></li> <li>Anhydrous meso tartaric acid form two anhydrous <a href="/wiki/Polymorphism_(materials_science)" class="mw-redirect" title="Polymorphism (materials science)">polymorphs</a>: triclinic and orthorhombic.</li> <li>Monohydrated meso tartaric acid crystallizes as monoclinic and triclinic polymorphys depending on the temperature at which crystallization from aqueous solution occurs.<sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup></li></ul> <p>Tartaric acid in <a href="/wiki/Fehling%27s_solution" title="Fehling's solution">Fehling's solution</a> binds to copper(II) ions, preventing the formation of insoluble hydroxide salts. </p> <table class="wikitable" style="text-align:center;"> <tbody><tr> <th colspan="2"><small>DL</small>-tartaric acid (<a href="/wiki/Racemic_acid" title="Racemic acid">racemic acid</a>) <small>(when in 1:1 ratio)</small> </th> <th rowspan="2">mesotartaric acid </th></tr> <tr> <th>dextrotartaric acid<br /><small>(L-(+)-tartaric acid)</small> </th> <th>levotartaric acid<br /><small>(D-(−)-tartaric acid)</small> </th></tr> <tr> <td width="150"><span class="mw-default-size skin-invert-image" typeof="mw:File"><a href="/wiki/File:L-tartaric_acid.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/8/89/L-tartaric_acid.png" decoding="async" width="94" height="144" class="mw-file-element" data-file-width="94" data-file-height="144" /></a></span> </td> <td width="150"><span class="mw-default-size skin-invert-image" typeof="mw:File"><a href="/wiki/File:D-tartaric_acid.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/b/b8/D-tartaric_acid.png" decoding="async" width="97" height="144" class="mw-file-element" data-file-width="97" data-file-height="144" /></a></span> </td> <td width="270"><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:Meso-Weins%C3%A4ure_Spiegel.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/64/Meso-Weins%C3%A4ure_Spiegel.svg/150px-Meso-Weins%C3%A4ure_Spiegel.svg.png" decoding="async" width="150" height="150" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/64/Meso-Weins%C3%A4ure_Spiegel.svg/225px-Meso-Weins%C3%A4ure_Spiegel.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/64/Meso-Weins%C3%A4ure_Spiegel.svg/300px-Meso-Weins%C3%A4ure_Spiegel.svg.png 2x" data-file-width="137" data-file-height="137" /></a></span> </td></tr></tbody></table> <div style="clear:both;" class=""></div> <table class="wikitable"> <caption>Forms of tartaric acid </caption> <tbody><tr> <th><a href="/wiki/Common_name" title="Common name">Common name</a> </th> <th>Tartaric acid </th> <th>Levotartaric acid </th> <th>Dextrotartaric acid </th> <th>Mesotartaric acid </th> <th>Racemic acid </th></tr> <tr align="center"> <th>Synonyms </th> <td> </td> <td style="vertical-align:top">(2<i>S</i>,3<i>S</i>)-tartaric acid <br /> (<i>S</i>,<i>S</i>)-tartaric acid <br /> (−)-tartaric acid <br /> <i>l</i>-tartaric acid <small><i>(obsolete)</i></small> <br /> levotartaric acid <br /> <small>D</small>-tartaric acid <br /> <small>D</small>-threaric acid <br />('unnatural isomer')<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> </td> <td style="vertical-align:top">(2<i>R</i>,3<i>R</i>)-tartaric acid <br /> (<i>R</i>,<i>R</i>)-tartaric acid <br /> (+)-tartaric acid <br /> <i>d</i>-tartaric acid <small><i>(obsolete)</i></small> <br /> <small>L</small>-tartaric acid <br /> <small>L</small>-threaric acid <br />(‘natural isomer’)<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> </td> <td style="vertical-align:top">(2<i>R</i>,3<i>S</i>)-tartaric acid <br /> <i>meso</i>-tartaric acid <br /> erythraric acid </td> <td style="vertical-align:top"><i>rac</i>-(2<i>R</i>,3<i>S</i>)-tartaric acid <br /> (2<i>RS</i>,3<i>SR</i>)-tartaric acid <br /> (±)-tartaric acid <br /> <small>DL</small>-tartaric acid <br /> <i>dl</i>-tartaric acid <small><i>(obsolete)</i></small> <br /> paratartaric acid <br /> uvic acid </td></tr> <tr align="center"> <th><a href="/wiki/PubChem" title="PubChem">PubChem</a> </th> <td><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/875">CID 875</a> from <a href="/wiki/PubChem" title="PubChem">PubChem</a> </td> <td><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/439655">CID 439655</a> from <a href="/wiki/PubChem" title="PubChem">PubChem</a> </td> <td><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/444305">CID 444305</a> from <a href="/wiki/PubChem" title="PubChem">PubChem</a> </td> <td><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/78956">CID 78956</a> from <a href="/wiki/PubChem" title="PubChem">PubChem</a> </td> <td><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/5851">CID 5851</a> from <a href="/wiki/PubChem" title="PubChem">PubChem</a> </td></tr> <tr align="center"> <th><a href="/wiki/EINECS_number" class="mw-redirect" title="EINECS number">EINECS number</a> </th> <td> </td> <td><span class="plainlinks noexpand"><a rel="nofollow" class="external text" href="http://www.dereferer.org/?http://esis.jrc.ec.europa.eu/index.php?GENRE=ECNO&ENTREE=205-695-6">205-695-6</a></span> </td> <td><span class="plainlinks noexpand"><a rel="nofollow" class="external text" href="http://www.dereferer.org/?http://esis.jrc.ec.europa.eu/index.php?GENRE=ECNO&ENTREE=201-766-0">201-766-0</a></span> </td> <td><span class="plainlinks noexpand"><a rel="nofollow" class="external text" href="http://www.dereferer.org/?http://esis.jrc.ec.europa.eu/index.php?GENRE=ECNO&ENTREE=205-696-1">205-696-1</a></span> </td> <td><span class="plainlinks noexpand"><a rel="nofollow" class="external text" href="http://www.dereferer.org/?http://esis.jrc.ec.europa.eu/index.php?GENRE=ECNO&ENTREE=205-105-7">205-105-7</a></span> </td></tr> <tr align="center"> <th><a href="/wiki/CAS_number" class="mw-redirect" title="CAS number">CAS number</a> </th> <td>526-83-0 </td> <td>147-71-7 </td> <td>87-69-4 </td> <td>147-73-9 </td> <td>133-37-9 </td></tr></tbody></table> <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=Tartaric_acid&action=edit&section=3" title="Edit section: Production"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="L-(+)-Tartaric_acid"><span id="L-.28.2B.29-Tartaric_acid"></span><small>L</small>-(+)-Tartaric acid</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tartaric_acid&action=edit&section=4" title="Edit section: L-(+)-Tartaric acid"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The <small>L</small>-(+)-tartaric acid isomer of tartaric acid is industrially produced in the largest amounts. It is obtained from <a href="/wiki/Lees_(fermentation)" title="Lees (fermentation)">lees</a>, a solid byproduct of fermentations. The former byproducts mostly consist of potassium bitartrate (<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">KHC<sub class="template-chem2-sub">4</sub>H<sub class="template-chem2-sub">4</sub>O<sub class="template-chem2-sub">6</sub></span>). This potassium salt is converted to <a href="/wiki/Calcium_tartrate" title="Calcium tartrate">calcium tartrate</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CaC<sub class="template-chem2-sub">4</sub>H<sub class="template-chem2-sub">4</sub>O<sub class="template-chem2-sub">6</sub></span>) upon treatment with <a href="/wiki/Calcium_hydroxide" title="Calcium hydroxide">calcium hydroxide</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Ca(OH)<sub class="template-chem2-sub">2</sub></span>):<sup id="cite_ref-Ullman_23-0" class="reference"><a href="#cite_note-Ullman-23"><span class="cite-bracket">[</span>23<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">KH(C<sub class="template-chem2-sub">4</sub>H<sub class="template-chem2-sub">4</sub>O<sub class="template-chem2-sub">6</sub>) + Ca(OH)<sub class="template-chem2-sub">2</sub> → Ca(C<sub class="template-chem2-sub">4</sub>H<sub class="template-chem2-sub">4</sub>O<sub class="template-chem2-sub">6</sub>) + KOH + H<sub class="template-chem2-sub">2</sub>O</span></dd></dl> <p>In practice, higher yields of calcium tartrate are obtained with the addition of <a href="/wiki/Calcium_sulfate" title="Calcium sulfate">calcium sulfate</a>. Calcium tartrate is then converted to tartaric acid by treating the salt with aqueous sulfuric acid: </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Ca(C<sub class="template-chem2-sub">4</sub>H<sub class="template-chem2-sub">4</sub>O<sub class="template-chem2-sub">6</sub>) + H<sub class="template-chem2-sub">2</sub>SO<sub class="template-chem2-sub">4</sub> → H<sub class="template-chem2-sub">2</sub>(C<sub class="template-chem2-sub">4</sub>H<sub class="template-chem2-sub">4</sub>O<sub class="template-chem2-sub">6</sub>) + CaSO<sub class="template-chem2-sub">4</sub></span></dd></dl> <div class="mw-heading mw-heading3"><h3 id="Racemic_tartaric_acid">Racemic tartaric acid</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tartaric_acid&action=edit&section=5" title="Edit section: Racemic tartaric acid"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Racemic tartaric acid can be prepared in a multistep reaction from <a href="/wiki/Maleic_acid" title="Maleic acid">maleic acid</a>. In the first step, the maleic acid is <a href="/wiki/Epoxide" title="Epoxide">epoxidized</a> by <a href="/wiki/Hydrogen_peroxide" title="Hydrogen peroxide">hydrogen peroxide</a> using <a href="/w/index.php?title=Potassium_tungstate&action=edit&redlink=1" class="new" title="Potassium tungstate (page does not exist)">potassium tungstate</a><span class="noprint" style="font-size:85%; font-style: normal;"> [<a href="https://de.wikipedia.org/wiki/Kaliumwolframat" class="extiw" title="de:Kaliumwolframat">de</a>]</span> as a catalyst.<sup id="cite_ref-Ullman_23-1" class="reference"><a href="#cite_note-Ullman-23"><span class="cite-bracket">[</span>23<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">HO<sub class="template-chem2-sub">2</sub>CCH=CHCO<sub class="template-chem2-sub">2</sub>H + H<sub class="template-chem2-sub">2</sub>O<sub class="template-chem2-sub">2</sub> → HO<sub class="template-chem2-sub">2</sub>C(CHCH)(O)CO<sub class="template-chem2-sub">2</sub>H + H<sub class="template-chem2-sub">2</sub>O</span></dd></dl> <p>In the next step, the epoxide is hydrolyzed. </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">HO<sub class="template-chem2-sub">2</sub>C(CHCH)(O)CO<sub class="template-chem2-sub">2</sub>H + H<sub class="template-chem2-sub">2</sub>O → HO<sub class="template-chem2-sub">2</sub>CCH(OH)CH(OH)CO<sub class="template-chem2-sub">2</sub>H</span></dd></dl> <div class="mw-heading mw-heading3"><h3 id="meso-Tartaric_acid"><i>meso</i>-Tartaric acid</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tartaric_acid&action=edit&section=6" title="Edit section: meso-Tartaric acid"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>A mixture of racemic acid and <i>meso</i>-tartaric acid is formed when <i>dextro</i>-Tartaric acid is heated in water at 165 °C for about 2 days. <i>meso</i>-Tartaric acid can also be prepared from dibromosuccinic acid using silver hydroxide:<sup id="cite_ref-Aug_24-0" class="reference"><a href="#cite_note-Aug-24"><span class="cite-bracket">[</span>24<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">HO<sub class="template-chem2-sub">2</sub>CCHBrCHBrCO<sub class="template-chem2-sub">2</sub>H + 2 AgOH → HO<sub class="template-chem2-sub">2</sub>CCH(OH)CH(OH)CO<sub class="template-chem2-sub">2</sub>H + 2 AgBr</span></dd></dl> <p><i>meso</i>-Tartaric acid can be separated from residual racemic acid by crystallization, the racemate being less soluble. </p> <div class="mw-heading mw-heading2"><h2 id="Reactivity">Reactivity</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tartaric_acid&action=edit&section=7" title="Edit section: Reactivity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>L-(+)-tartaric acid, can participate in several reactions. As shown the reaction scheme below, dihydroxymaleic acid is produced upon treatment of L-(+)-tartaric acid with hydrogen peroxide in the presence of a <a href="/wiki/Ferrous" title="Ferrous">ferrous</a> salt. </p> <dl><dd>HO<sub>2</sub>CCH(OH)CH(OH)CO<sub>2</sub>H + H<sub>2</sub>O<sub>2</sub> → HO<sub>2</sub>CC(OH)C(OH)CO<sub>2</sub>H + 2 H<sub>2</sub>O</dd></dl> <p><a href="/w/index.php?title=Dihydroxymaleic_acid&action=edit&redlink=1" class="new" title="Dihydroxymaleic acid (page does not exist)">Dihydroxymaleic acid</a> can then be oxidized to <a href="/wiki/Tartronic_acid" title="Tartronic acid">tartronic acid</a> with nitric acid.<sup id="cite_ref-Blair_25-0" class="reference"><a href="#cite_note-Blair-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Derivatives">Derivatives</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tartaric_acid&action=edit&section=8" title="Edit section: Derivatives"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Brechweinstein.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/fc/Brechweinstein.jpg/220px-Brechweinstein.jpg" decoding="async" width="220" height="292" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/fc/Brechweinstein.jpg/330px-Brechweinstein.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/fc/Brechweinstein.jpg/440px-Brechweinstein.jpg 2x" data-file-width="552" data-file-height="733" /></a><figcaption>Tartar emetic</figcaption></figure> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:CommercialTartaric.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/CommercialTartaric.jpg/220px-CommercialTartaric.jpg" decoding="async" width="220" height="165" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/CommercialTartaric.jpg/330px-CommercialTartaric.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6f/CommercialTartaric.jpg/440px-CommercialTartaric.jpg 2x" data-file-width="2816" data-file-height="2112" /></a><figcaption>Commercially produced tartaric acid</figcaption></figure> <p>Important derivatives of tartaric acid include: </p> <ul><li><a href="/wiki/Sodium_ammonium_tartrate" title="Sodium ammonium tartrate">Sodium ammonium tartrate</a>, the first material separated into its <a href="/wiki/Enantiomer" title="Enantiomer">enantiomers</a></li> <li>cream of tartar (<a href="/wiki/Potassium_bitartrate" title="Potassium bitartrate">potassium bitartrate</a>), used in <a href="/wiki/Cooking" title="Cooking">cooking</a></li> <li><a href="/wiki/Potassium_sodium_tartrate" title="Potassium sodium tartrate">Rochelle salt</a> (potassium sodium tartrate), which has unusual piezoelectric properties</li> <li><a href="/wiki/Antimony_potassium_tartrate" title="Antimony potassium tartrate">tartar emetic</a> (antimony potassium tartrate), a <a href="/wiki/Resolving_agent" class="mw-redirect" title="Resolving agent">resolving agent</a>.<sup id="cite_ref-26" class="reference"><a href="#cite_note-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-McCallum_27-0" class="reference"><a href="#cite_note-McCallum-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-28" class="reference"><a href="#cite_note-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Diisopropyl_tartrate" title="Diisopropyl tartrate">Diisopropyl tartrate</a> is used as a <a href="/wiki/Catalysis" title="Catalysis">co-catalyst</a> in asymmetric synthesis.</li></ul> <p>Tartaric acid is a <a href="/wiki/Muscle" title="Muscle">muscle</a> <a href="/wiki/Toxin" title="Toxin">toxin</a>, which works by inhibiting the production of <a href="/wiki/Malic_acid" title="Malic acid">malic acid</a>, and in high doses causes paralysis and death.<sup id="cite_ref-29" class="reference"><a href="#cite_note-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> The <a href="/wiki/Median_lethal_dose" title="Median lethal dose">median lethal dose</a> (LD<sub>50</sub>) is about 7.5 grams/kg for a human, 5.3 grams/kg for rabbits, and 4.4 grams/kg for mice.<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> Given this figure, it would take over 500 g (18 oz) to kill a person weighing 70 kg (150 lb) with 50% probability, so it may be safely included in many foods, especially sour-tasting <a href="/wiki/Sweetness" title="Sweetness">sweets</a>. As a <a href="/wiki/Food_additive" title="Food additive">food additive</a>, tartaric acid is used as an <a href="/wiki/Antioxidant" title="Antioxidant">antioxidant</a> with <a href="/wiki/E_number" title="E number">E number</a> <b>E334</b>; <a href="/wiki/Tartrate" title="Tartrate">tartrates</a> are other additives serving as antioxidants or <a href="/wiki/Emulsion" title="Emulsion">emulsifiers</a>. </p><p>When cream of tartar is added to water, a suspension results which serves to clean copper <a href="/wiki/Coin" title="Coin">coins</a> very well, as the tartrate solution can dissolve the layer of copper(II) oxide present on the surface of the coin. The resulting copper(II)-tartrate complex is easily soluble in water. </p> <div class="mw-heading mw-heading2"><h2 id="Tartaric_acid_in_wine">Tartaric acid in wine</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tartaric_acid&action=edit&section=9" title="Edit section: Tartaric acid in wine"><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/Acids_in_wine" title="Acids in wine">Acids in wine</a> and <a href="/wiki/Tartrate" title="Tartrate">Tartrate</a></div><style data-mw-deduplicate="TemplateStyles:r1251242444">.mw-parser-output .ambox{border:1px solid #a2a9b1;border-left:10px solid #36c;background-color:#fbfbfb;box-sizing:border-box}.mw-parser-output .ambox+link+.ambox,.mw-parser-output .ambox+link+style+.ambox,.mw-parser-output .ambox+link+link+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+style+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+link+.ambox{margin-top:-1px}html body.mediawiki .mw-parser-output .ambox.mbox-small-left{margin:4px 1em 4px 0;overflow:hidden;width:238px;border-collapse:collapse;font-size:88%;line-height:1.25em}.mw-parser-output .ambox-speedy{border-left:10px solid #b32424;background-color:#fee7e6}.mw-parser-output .ambox-delete{border-left:10px solid #b32424}.mw-parser-output .ambox-content{border-left:10px solid #f28500}.mw-parser-output .ambox-style{border-left:10px solid #fc3}.mw-parser-output .ambox-move{border-left:10px solid #9932cc}.mw-parser-output .ambox-protection{border-left:10px solid #a2a9b1}.mw-parser-output .ambox .mbox-text{border:none;padding:0.25em 0.5em;width:100%}.mw-parser-output .ambox .mbox-image{border:none;padding:2px 0 2px 0.5em;text-align:center}.mw-parser-output .ambox .mbox-imageright{border:none;padding:2px 0.5em 2px 0;text-align:center}.mw-parser-output .ambox .mbox-empty-cell{border:none;padding:0;width:1px}.mw-parser-output .ambox .mbox-image-div{width:52px}@media(min-width:720px){.mw-parser-output .ambox{margin:0 10%}}@media print{body.ns-0 .mw-parser-output .ambox{display:none!important}}</style><table class="box-More_citations_needed plainlinks metadata ambox ambox-content ambox-Refimprove" role="presentation"><tbody><tr><td class="mbox-image"><div class="mbox-image-div"><span typeof="mw:File"><a href="/wiki/File:Question_book-new.svg" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/9/99/Question_book-new.svg/50px-Question_book-new.svg.png" decoding="async" width="50" height="39" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/9/99/Question_book-new.svg/75px-Question_book-new.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/9/99/Question_book-new.svg/100px-Question_book-new.svg.png 2x" data-file-width="512" data-file-height="399" /></a></span></div></td><td class="mbox-text"><div class="mbox-text-span">This article <b>needs additional citations for <a href="/wiki/Wikipedia:Verifiability" title="Wikipedia:Verifiability">verification</a></b>.<span class="hide-when-compact"> Please help <a href="/wiki/Special:EditPage/Tartaric_acid" title="Special:EditPage/Tartaric acid">improve this article</a> by <a href="/wiki/Help:Referencing_for_beginners" title="Help:Referencing for beginners">adding citations to reliable sources</a>. Unsourced material may be challenged and removed.<br /><small><span class="plainlinks"><i>Find sources:</i> <a rel="nofollow" class="external text" href="https://www.google.com/search?as_eq=wikipedia&q=%22Tartaric+acid%22">"Tartaric acid"</a> – <a rel="nofollow" class="external text" href="https://www.google.com/search?tbm=nws&q=%22Tartaric+acid%22+-wikipedia&tbs=ar:1">news</a> <b>·</b> <a rel="nofollow" class="external text" href="https://www.google.com/search?&q=%22Tartaric+acid%22&tbs=bkt:s&tbm=bks">newspapers</a> <b>·</b> <a rel="nofollow" class="external text" href="https://www.google.com/search?tbs=bks:1&q=%22Tartaric+acid%22+-wikipedia">books</a> <b>·</b> <a rel="nofollow" class="external text" href="https://scholar.google.com/scholar?q=%22Tartaric+acid%22">scholar</a> <b>·</b> <a rel="nofollow" class="external text" href="https://www.jstor.org/action/doBasicSearch?Query=%22Tartaric+acid%22&acc=on&wc=on">JSTOR</a></span></small></span> <span class="date-container"><i>(<span class="date">November 2023</span>)</i></span><span class="hide-when-compact"><i> (<small><a href="/wiki/Help:Maintenance_template_removal" title="Help:Maintenance template removal">Learn how and when to remove this message</a></small>)</i></span></div></td></tr></tbody></table><figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:HomemadeTartaric.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/2c/HomemadeTartaric.jpg/220px-HomemadeTartaric.jpg" decoding="async" width="220" height="165" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/2c/HomemadeTartaric.jpg/330px-HomemadeTartaric.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/2c/HomemadeTartaric.jpg/440px-HomemadeTartaric.jpg 2x" data-file-width="2816" data-file-height="2112" /></a><figcaption>Unpurified potassium bitartrate can take on the color of the grape juice from which it was separated.</figcaption></figure> <p>Tartaric acid may be most immediately recognizable to wine drinkers as the source of "wine diamonds", the small <a href="/wiki/Potassium_bitartrate" title="Potassium bitartrate">potassium bitartrate</a> crystals that sometimes form spontaneously on the <a href="/wiki/Cork_(material)" title="Cork (material)">cork</a> or bottom of the bottle. These "tartrates" are harmless, despite sometimes being mistaken for broken glass, and are prevented in many wines through <a href="/wiki/Cold_stabilization" class="mw-redirect" title="Cold stabilization">cold stabilization</a> (which is not always preferred since it can change the wine's profile). The tartrates remaining on the inside of <a href="/wiki/Aging_barrel" class="mw-redirect" title="Aging barrel">aging barrels</a> were at one time a major industrial source of potassium bitartrate. </p><p>Tartaric acid plays an important role chemically, lowering the pH of fermenting "must" to a level where many undesirable spoilage bacteria cannot live, and acting as a preservative after <a href="/wiki/Fermentation_(wine)" class="mw-redirect" title="Fermentation (wine)">fermentation</a>. In the mouth, tartaric acid provides some of the tartness in the wine, although <a href="/wiki/Citric_acid" title="Citric acid">citric</a> and <a href="/wiki/Malic_acid" title="Malic acid">malic acids</a> also play a role. </p> <div class="mw-heading mw-heading2"><h2 id="Tartaric_acid_in_fruits">Tartaric acid in fruits</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tartaric_acid&action=edit&section=10" title="Edit section: Tartaric acid in fruits"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Grapes and tamarinds have the highest levels of tartaric acid concentration. Other fruits with tartaric acid are <a href="/wiki/Banana" title="Banana">bananas</a>, <a href="/wiki/Avocado" title="Avocado">avocados</a>, <a href="/wiki/Opuntia_ficus-indica" title="Opuntia ficus-indica">prickly pear</a> fruit, <a href="/wiki/Apple" title="Apple">apples</a>, <a href="/wiki/Cherry" title="Cherry">cherries</a>, <a href="/wiki/Papaya" title="Papaya">papayas</a>, <a href="/wiki/Peach" title="Peach">peaches</a>, <a href="/wiki/Pear" title="Pear">pears</a>, <a href="/wiki/Pineapple" title="Pineapple">pineapples</a>, <a href="/wiki/Strawberry" title="Strawberry">strawberries</a>, <a href="/wiki/Mango" title="Mango">mangoes</a> and <a href="/wiki/Citrus" title="Citrus">citrus fruits</a>.<sup id="cite_ref-pubchem_1-2" class="reference"><a href="#cite_note-pubchem-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-31" class="reference"><a href="#cite_note-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> </p><p>Trace amounts of tartaric acid have been found in <a href="/wiki/Cranberry" title="Cranberry">cranberries</a> and other <a href="/wiki/Berry" title="Berry">berries</a>.<sup id="cite_ref-32" class="reference"><a href="#cite_note-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> </p><p>Tartaric acid is also present in the leaves and pods of <a href="/wiki/Pelargonium" title="Pelargonium">Pelargonium</a> plants and <a href="/wiki/Phaseolus_vulgaris" title="Phaseolus vulgaris">beans</a>. </p> <div class="mw-heading mw-heading2"><h2 id="Applications">Applications</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tartaric_acid&action=edit&section=11" title="Edit section: Applications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Tartaric acid and its derivatives have a plethora of uses in the field of pharmaceuticals. For example, it has been used in the production of effervescent salts, in combination with citric acid, to improve the taste of oral medications.<sup id="cite_ref-Blair_25-1" class="reference"><a href="#cite_note-Blair-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> The potassium antimonyl derivative of the acid known as tartar emetic is included, in small doses, in <a href="/wiki/Cough_syrup" class="mw-redirect" title="Cough syrup">cough syrup</a> as an <a href="/wiki/Expectorant" class="mw-redirect" title="Expectorant">expectorant</a>. </p><p>Tartaric acid also has several applications for industrial use. The acid has been observed to <a href="/wiki/Chelation" title="Chelation">chelate</a> metal ions such as calcium and magnesium. Therefore, the acid has served in the farming and metal industries as a chelating agent for complexing micronutrients in soil <a href="/wiki/Fertilizer" title="Fertilizer">fertilizer</a> and for cleaning metal surfaces consisting of aluminium, copper, iron, and alloys of these metals, respectively.<sup id="cite_ref-Ullman_23-2" class="reference"><a href="#cite_note-Ullman-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Toxicity_in_canines">Toxicity in canines</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tartaric_acid&action=edit&section=12" title="Edit section: Toxicity in canines"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>While tartaric acid is well-tolerated by humans and lab animals, an April 2021 letter to the editor of <i><a href="/wiki/Journal_of_the_American_Veterinary_Medical_Association" class="mw-redirect" title="Journal of the American Veterinary Medical Association">JAVMA</a></i> hypothesized that the tartaric acid in grapes could be the cause of <a href="/wiki/Grape_and_raisin_toxicity_in_dogs" class="mw-redirect" title="Grape and raisin toxicity in dogs">grape and raisin toxicity in dogs</a>.<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><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> Other studies have observed tartaric acid toxicity in kidney cells of dogs, but not in human kidney cells.<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> </p><p>In dogs, the tartaric acid of <a href="/wiki/Tamarind" title="Tamarind">tamarind</a> causes <a href="/wiki/Acute_kidney_injury" title="Acute kidney injury">acute kidney injury</a>, which can often be fatal.<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>A review identified a relationship between grape ingestion and illness, though the specific type or quantity of grapes that cause toxicity remains unclear. Grape ingestion commonly leads to gastrointestinal and/or renal issues, with treatment depending on the symptoms; outcomes can vary.<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> </p> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tartaric_acid&action=edit&section=13" 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-pubchem-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-pubchem_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-pubchem_1-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-pubchem_1-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=875&loc=ec_rcs">Tartaric Acid – Compound Summary</a>, <a href="/wiki/PubChem" title="PubChem">PubChem</a>.</span> </li> <li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text"><a rel="nofollow" class="external free" href="https://iupac.qmul.ac.uk/2carb/23.html">https://iupac.qmul.ac.uk/2carb/23.html</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">In the older literature, there is confusion about the use of D and L in the case of tartaric acids. It is therefore recommended to use the R,S system in this case.</span> </li> <li id="cite_note-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-4">^</a></b></span> <span class="reference-text"><a rel="nofollow" class="external free" href="https://iupac.qmul.ac.uk/2carb/23.html">https://iupac.qmul.ac.uk/2carb/23.html</a></span> </li> <li id="cite_note-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-5">^</a></b></span> <span class="reference-text">Dawson, R.M.C. et al., <i>Data for Biochemical Research</i>, Oxford, Clarendon Press, 1959.</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">GHS: <a rel="nofollow" class="external text" href="https://gestis.dguv.de/data?name=033480&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-7"><span class="mw-cite-backlink"><b><a href="#cite_ref-7">^</a></b></span> <span class="reference-text">Retzius, Anders Jahan (1770) <a rel="nofollow" class="external text" href="https://babel.hathitrust.org/cgi/pt?id=mdp.39015039452886;view=1up;seq=605">"Försök med vinsten och dess syra"</a> (Experiments with cream of tartar and its acid), <i>Kungliga Vetenskapsakademiens Handlingar</i> (Proceedings of the Royal Academy of Sciences), <b>31</b> : 207–213. <a rel="nofollow" class="external text" href="https://babel.hathitrust.org/cgi/pt?id=mdp.39015039452886;view=1up;seq=607">From p. 209:</a> <i>"§. 6. Dessa försök omtalte jag för Hr. Carl Wilhelm Scheele (en snabb och lårgirug Pharmaciæ Studiosus) … "</i> (§. 6. I mention these experiments on behalf of Mr. Carl Wilhelm Scheele (a quick and studious student of pharmacology) … )</span> </li> <li id="cite_note-8"><span class="mw-cite-backlink"><b><a href="#cite_ref-8">^</a></b></span> <span class="reference-text">Biot (1835) <a rel="nofollow" class="external text" href="http://gallica.bnf.fr/ark:/12148/bpt6k32283/f149.image">"Mémoire sur la polarization circulaire et sur ses applications à la chimie organique"</a> (Memoir on circular polarization and on its applications to organic chemistry), <i>Mémoires de l'Académie des sciences de l'Institut</i>, 2nd series, <b>13</b> : 39–175. That tartaric acid (<i>acide tartarique cristallisé</i>) rotates plane-polarized light is shown in <a rel="nofollow" class="external text" href="http://gallica.bnf.fr/ark:/12148/bpt6k32283/f285.image">Table G following p. 168.</a> (Note: This article was read to the French Royal Academy of Sciences on 1832 November 5.)</span> </li> <li id="cite_note-9"><span class="mw-cite-backlink"><b><a href="#cite_ref-9">^</a></b></span> <span class="reference-text">Biot (1838) <a rel="nofollow" class="external text" href="https://babel.hathitrust.org/cgi/pt?id=mdp.39015077785536;view=1up;seq=145">"Pour discerner les mélanges et les combinaisons chimiques définies ou non définies, qui agissent sur la lumière polarisée; suivies d'applications aux combinaisons de l'acide tartarique avec l'eau, l'alcool et l'esprit de bois"</a> (In order to discern mixtures and chemical combinations, defined or undefined, which act on polarized light; followed by applications to combinations of tartaric acid with water, alcohol [i.e., ethanol], and spirit of wood [i.e., methanol]), <i>Mémoires de l'Académie des sciences de l'Institut</i>, 2nd series, <b>15</b> : 93–279.</span> </li> <li id="cite_note-10"><span class="mw-cite-backlink"><b><a href="#cite_ref-10">^</a></b></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFPasteur1848" class="citation journal cs1 cs1-prop-foreign-lang-source">Pasteur, L. (1848). <a rel="nofollow" class="external text" href="https://www.biodiversitylibrary.org/item/21163#page/545/mode/1up">"Mémoire sur la relation qui peut exister entre la forme cristalline et la composition chimique, et sur la cause de la polarisation rotatoire"</a> [Memoir on the relationship which can exist between crystalline form and chemical composition, and on the cause of rotary polarization]. <i>Comptes rendus de l'Académie des sciences de Paris</i> (in French). <b>26</b>: <span class="nowrap">535–</span>538.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Comptes+rendus+de+l%27Acad%C3%A9mie+des+sciences+de+Paris&rft.atitle=M%C3%A9moire+sur+la+relation+qui+peut+exister+entre+la+forme+cristalline+et+la+composition+chimique%2C+et+sur+la+cause+de+la+polarisation+rotatoire&rft.volume=26&rft.pages=%3Cspan+class%3D%22nowrap%22%3E535-%3C%2Fspan%3E538&rft.date=1848&rft.aulast=Pasteur&rft.aufirst=L.&rft_id=https%3A%2F%2Fwww.biodiversitylibrary.org%2Fitem%2F21163%23page%2F545%2Fmode%2F1up&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATartaric+acid" class="Z3988"></span></span> </li> <li id="cite_note-11"><span class="mw-cite-backlink"><b><a href="#cite_ref-11">^</a></b></span> <span class="reference-text">L. Pasteur (1848) <a rel="nofollow" class="external text" href="https://books.google.com/books?id=gJ45AAAAcAAJ&pg=PA442">"Sur les relations qui peuvent exister entre la forme cristalline, la composition chimique et le sens de la polarisation rotatoire"</a> (On the relations that can exist between crystalline form, and chemical composition, and the sense of rotary polarization), <i>Annales de Chimie et de Physique</i>, 3rd series, <b>24</b> : 442–459.</span> </li> <li id="cite_note-12"><span class="mw-cite-backlink"><b><a href="#cite_ref-12">^</a></b></span> <span class="reference-text">Pasteur, Louis (1850) <a rel="nofollow" class="external text" href="https://babel.hathitrust.org/cgi/pt?id=hvd.hx3dy7;view=1up;seq=66">"Recherches sur les propriétés spécifiques des deux acides qui composent l'acide racémique"</a> [Investigations into the specific properties of the two acids that compose racemic acid], <i>Annales de Chimie et de Physique</i>, 3rd series, <b>28</b> (3) : 56–99. See also <a rel="nofollow" class="external text" href="https://babel.hathitrust.org/cgi/pt?id=hvd.hx3dy7;view=1up;seq=519">Plate II.</a> (See also the report of the commission that was appointed to verify Pasteur's findings, pp. 99–117.) [in French]</span> </li> <li id="cite_note-13"><span class="mw-cite-backlink"><b><a href="#cite_ref-13">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGeorge_B._KauffmanRobin_D._Myers1998" class="citation journal cs1">George B. Kauffman; Robin D. Myers (1998). <a rel="nofollow" class="external text" href="https://web.archive.org/web/20060117144722/http://192.129.24.144/licensed_materials/00897/papers/0003006/36kau897.pdf">"Pasteur's resolution of racemic acid: A sesquicentennial retrospect and a new translation"</a> <span class="cs1-format">(PDF)</span>. <i>The Chemical Educator</i>. <b>3</b> (6): <span class="nowrap">1–</span>4. <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%2Fs00897980257a">10.1007/s00897980257a</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:95862598">95862598</a>. 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title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Veterinary+Record&rft.atitle=Scoping+review+exploring+the+evidence+base+on+Vitis+vinifera+toxicity+in+dogs+after+ingestion%3A+Clinical+effects%2C+treatments+and+types+of+V.+vinifera&rft.volume=195&rft.issue=7&rft.date=2024-10-05&rft.issn=0042-4900&rft_id=info%3Apmid%2F39183495&rft_id=info%3Adoi%2F10.1002%2Fvetr.4536&rft.aulast=Downs&rft.aufirst=Joshua&rft.au=Zoltowska%2C+Agnieszka&rft.au=Hackney%2C+Thomas&rft.au=Gardner%2C+David+S.&rft.au=Ashmore%2C+Alison&rft.au=Brennan%2C+Marnie+L.&rft_id=https%3A%2F%2Fdoi.org%2F10.1002%252Fvetr.4536&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATartaric+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=Tartaric_acid&action=edit&section=14" title="Edit section: External 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