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id="toc-Uses_as_a_medication-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Hazards" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Hazards"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Hazards</span> </div> </a> <ul id="toc-Hazards-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Crocodilian_coloration" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Crocodilian_coloration"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Crocodilian coloration</span> </div> </a> <ul id="toc-Crocodilian_coloration-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">5</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-General_references" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#General_references"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>General references</span> </div> </a> <ul id="toc-General_references-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 25 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-25" 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">25 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-af mw-list-item"><a href="https://af.wikipedia.org/wiki/Looisuur" title="Looisuur – Afrikaans" lang="af" hreflang="af" data-title="Looisuur" data-language-autonym="Afrikaans" data-language-local-name="Afrikaans" class="interlanguage-link-target"><span>Afrikaans</span></a></li><li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%AD%D9%85%D8%B6_%D8%A7%D9%84%D8%AA%D8%A7%D9%86%D9%8A%D9%83" title="حمض التانيك – Arabic" lang="ar" hreflang="ar" data-title="حمض التانيك" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-ast mw-list-item"><a href="https://ast.wikipedia.org/wiki/%C3%81cidu_t%C3%A1nico" title="Ácidu tánico – Asturian" lang="ast" hreflang="ast" data-title="Ácidu tánico" data-language-autonym="Asturianu" data-language-local-name="Asturian" class="interlanguage-link-target"><span>Asturianu</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D8%AA%D8%A7%D9%86%DB%8C%DA%A9_%D8%A7%D8%B3%DB%8C%D8%AF" title="تانیک اسید – South Azerbaijani" lang="azb" hreflang="azb" data-title="تانیک اسید" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/%C3%80cid_t%C3%A0nnic" title="Àcid tànnic – Catalan" lang="ca" hreflang="ca" data-title="Àcid tànnic" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Tannins%C3%A4ure" title="Tanninsäure – German" lang="de" hreflang="de" data-title="Tanninsäure" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/%C3%81cido_t%C3%A1nico" title="Ácido tánico – Spanish" lang="es" hreflang="es" data-title="Ácido tánico" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Azido_taniko" title="Azido taniko – Basque" lang="eu" hreflang="eu" data-title="Azido taniko" 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%D9%86%DB%8C%DA%A9_%D8%A7%D8%B3%DB%8C%D8%AF" title="تانیک اسید – Persian" lang="fa" hreflang="fa" data-title="تانیک 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_tannique" title="Acide tannique – French" lang="fr" hreflang="fr" data-title="Acide tannique" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Acido_tannico" title="Acido tannico – Italian" lang="it" hreflang="it" data-title="Acido tannico" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Looizuur" title="Looizuur – Dutch" lang="nl" hreflang="nl" data-title="Looizuur" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%BF%E3%83%B3%E3%83%8B%E3%83%B3%E9%85%B8" title="タンニン酸 – Japanese" lang="ja" hreflang="ja" data-title="タンニン酸" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Kwas_taninowy" title="Kwas taninowy – Polish" lang="pl" hreflang="pl" data-title="Kwas taninowy" 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_t%C3%A2nico" title="Ácido tânico – Portuguese" lang="pt" hreflang="pt" data-title="Ácido tânico" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Acid_tanic" title="Acid tanic – Romanian" lang="ro" hreflang="ro" data-title="Acid tanic" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%94%D1%83%D0%B1%D0%B8%D0%BB%D1%8C%D0%BD%D0%B0%D1%8F_%D0%BA%D0%B8%D1%81%D0%BB%D0%BE%D1%82%D0%B0" title="Дубильная кислота – Russian" lang="ru" hreflang="ru" data-title="Дубильная кислота" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Taninska_kiselina" title="Taninska kiselina – Serbian" lang="sr" hreflang="sr" data-title="Taninska kiselina" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Taninska_kiselina" title="Taninska kiselina – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Taninska kiselina" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%AA%E0%AE%A4%E0%AE%AE%E0%AE%BE%E0%AE%95%E0%AF%8D%E0%AE%95%E0%AE%BF_%E0%AE%85%E0%AE%AE%E0%AE%BF%E0%AE%B2%E0%AE%AE%E0%AF%8D(%E0%AE%9F%E0%AE%BE%E0%AE%A9%E0%AE%BF%E0%AE%95%E0%AF%8D_%E0%AE%85%E0%AE%AE%E0%AE%BF%E0%AE%B2%E0%AE%AE%E0%AF%8D)" title="பதமாக்கி அமிலம்(டானிக் அமிலம்) – Tamil" lang="ta" hreflang="ta" data-title="பதமாக்கி அமிலம்(டானிக் அமிலம்)" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%A2%D0%B0%D0%BD%D1%96%D0%BD%D0%BE%D0%B2%D0%B0_%D0%BA%D0%B8%D1%81%D0%BB%D0%BE%D1%82%D0%B0" title="Танінова кислота – Ukrainian" lang="uk" hreflang="uk" data-title="Танінова кислота" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Acid_tannic" title="Acid tannic – Vietnamese" lang="vi" hreflang="vi" data-title="Acid tannic" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target"><span>Tiếng Việt</span></a></li><li class="interlanguage-link interwiki-war mw-list-item"><a href="https://war.wikipedia.org/wiki/Aksido_Tanico" title="Aksido Tanico – Waray" lang="war" hreflang="war" data-title="Aksido Tanico" data-language-autonym="Winaray" data-language-local-name="Waray" class="interlanguage-link-target"><span>Winaray</span></a></li><li class="interlanguage-link interwiki-zh-yue mw-list-item"><a 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.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>Tannic acid </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Tannic_acid.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/65/Tannic_acid.svg/200px-Tannic_acid.svg.png" decoding="async" width="200" height="200" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/65/Tannic_acid.svg/300px-Tannic_acid.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/65/Tannic_acid.svg/400px-Tannic_acid.svg.png 2x" data-file-width="375" data-file-height="375" /></a><figcaption></figcaption></figure><div style="text-align:center;">Chemical structure of penta(digalloyl)glucose, a representative component of tannic acid</div> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Tannic_acid_STICK_model_decagalloyl.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/5a/Tannic_acid_STICK_model_decagalloyl.png/200px-Tannic_acid_STICK_model_decagalloyl.png" decoding="async" width="200" height="189" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/5a/Tannic_acid_STICK_model_decagalloyl.png/300px-Tannic_acid_STICK_model_decagalloyl.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/5a/Tannic_acid_STICK_model_decagalloyl.png/400px-Tannic_acid_STICK_model_decagalloyl.png 2x" data-file-width="873" data-file-height="824" /></a><figcaption></figcaption></figure> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Chemical_nomenclature" title="Chemical nomenclature">IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">1,2,3,4,6-penta-<i>O</i>-{3,4-dihydroxy-5-[(3,4,5-trihydroxybenzoyl)oxy]benzoyl}-<small>D</small>-glucopyranose</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;">2,3-dihydroxy-5-({[(2R,3R,4S,5R,6R)-3,4,5,6-tetrakis({3,4-dihydroxy-5-[(3,4,5-trihydroxyphenyl)carbonyloxy]phenyl}carbonyloxy)oxan-2-yl]methoxy}carbonyl)phenyl 3,4,5-trihydroxybenzoate</div></div> </td></tr> <tr> <td colspan="2" style="text-align:left;">Other names <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li>Acidum tannicum</li><li>Gallotannic acid</li><li>Digallic acid</li><li>Gallotannin</li><li>Tannimum</li><li>Quercitannin</li><li>Oak bark tannin</li><li>Quercotannic acid</li><li>Querci-tannic acid</li><li>Querco-tannic acid</li></ul></div></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><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=1401-55-4">1401-55-4</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=Oc1cc%28cc%28O%29c1O%29C%28%3DO%29Oc1cc%28cc%28O%29c1O%29C%28%3DO%29OC%5BC%40H%5D1O%5BC%40H%5D%28OC%28%3DO%29c2cc%28O%29c%28O%29c%28OC%28%3DO%29c3cc%28O%29c%28O%29c%28O%29c3%29c2%29%5BC%40H%5D%28OC%28%3DO%29c2cc%28O%29c%28O%29c%28OC%28%3DO%29c3cc%28O%29c%28O%29c%28O%29c3%29c2%29%5BC%40%40H%5D%28OC%28%3DO%29c2cc%28O%29c%28O%29c%28OC%28%3DO%29c3cc%28O%29c%28O%29c%28O%29c3%29c2%29%5BC%40%40H%5D1OC%28%3DO%29c1cc%28O%29c%28O%29c%28OC%28%3DO%29c2cc%28O%29c%28O%29c%28O%29c2%29c1">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Beilstein_database" title="Beilstein database">Beilstein Reference</a></div> </td> <td>8186386 </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=75211">CHEBI:75211</a></span><sup> <span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/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/ChEMBL506247">ChEMBL506247</a></span><sup> <span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/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.17286569.html">17286569</a></span><sup> <span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/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/100.014.321">100.014.321</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q427956#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><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/IUPHAR/BPS" class="mw-redirect" title="IUPHAR/BPS">IUPHAR/BPS</a></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.guidetopharmacology.org"><a rel="nofollow" class="external text" href="http://www.guidetopharmacology.org/GRAC/LigandDisplayForward?tab=summary&ligandId=4319">4319</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/KEGG" title="KEGG">KEGG</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.kegg.jp"><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/C13452">C13452</a></span><sup> <span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup></li></ul></div> </td></tr> <tr> <td><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/16129878">16129878</a></span></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/28F9E0DJY6">28F9E0DJY6</a></span><sup> <span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup></li></ul></div> </td></tr> <tr> <td><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/DTXSID2026076,">DTXSID00892987 DTXSID2026076, DTXSID00892987</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q427956#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/C76H52O46/c77-32-1-22(2-33(78)53(32)92)67(103)113-47-16-27(11-42(87)58(47)97)66(102)112-21-52-63(119-72(108)28-12-43(88)59(98)48(17-28)114-68(104)23-3-34(79)54(93)35(80)4-23)64(120-73(109)29-13-44(89)60(99)49(18-29)115-69(105)24-5-36(81)55(94)37(82)6-24)65(121-74(110)30-14-45(90)61(100)50(19-30)116-70(106)25-7-38(83)56(95)39(84)8-25)76(118-52)122-75(111)31-15-46(91)62(101)51(20-31)117-71(107)26-9-40(85)57(96)41(86)10-26/h1-20,52,63-65,76-101H,21H2/t52-,63-,64+,65-,76+/m1/s1<sup> <span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup></div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: LRBQNJMCXXYXIU-PPKXGCFTSA-N<sup> <span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup></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/C76H52O46/c77-32-1-22(2-33(78)53(32)92)67(103)113-47-16-27(11-42(87)58(47)97)66(102)112-21-52-63(119-72(108)28-12-43(88)59(98)48(17-28)114-68(104)23-3-34(79)54(93)35(80)4-23)64(120-73(109)29-13-44(89)60(99)49(18-29)115-69(105)24-5-36(81)55(94)37(82)6-24)65(121-74(110)30-14-45(90)61(100)50(19-30)116-70(106)25-7-38(83)56(95)39(84)8-25)76(118-52)122-75(111)31-15-46(91)62(101)51(20-31)117-71(107)26-9-40(85)57(96)41(86)10-26/h1-20,52,63-65,76-101H,21H2/t52-,63-,64+,65-,76+/m1/s1</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: LRBQNJMCXXYXIU-PPKXGCFTBB</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%;">Oc1cc(cc(O)c1O)C(=O)Oc1cc(cc(O)c1O)C(=O)OC[C@H]1O[C@H](OC(=O)c2cc(O)c(O)c(OC(=O)c3cc(O)c(O)c(O)c3)c2)[C@H](OC(=O)c2cc(O)c(O)c(OC(=O)c3cc(O)c(O)c(O)c3)c2)[C@@H](OC(=O)c2cc(O)c(O)c(OC(=O)c3cc(O)c(O)c(O)c3)c2)[C@@H]1OC(=O)c1cc(O)c(O)c(OC(=O)c2cc(O)c(O)c(O)c2)c1</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td><span title="Carbon">C</span><sub>76</sub><span title="Hydrogen">H</span><sub>52</sub><span title="Oxygen">O</span><sub>46</sub> </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td>1701.19 g/mol    </td></tr> <tr> <td><a href="/wiki/Density" title="Density">Density</a> </td> <td>2.12g/cm<sup>3</sup> </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>decomposes above 200 °C </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>2850 g/L or 250 g/L<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Solubility" title="Solubility">Solubility</a> </td> <td>100 g/L in ethanol<br /> 1 g/L in glycerol and acetone<br /> insoluble in benzene, chloroform, diethyl ether, petroleum, carbon disulfide, carbon tetrachloride. </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>ca. 6 </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; color:inherit; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"><div style="text-align:center;"><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/12px-X_mark.svg.png" decoding="async" width="12" height="14" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/18px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/24px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span> <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=408795684&page2=Tannic+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> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Bottle_of_tannic_acid.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d0/Bottle_of_tannic_acid.jpg/220px-Bottle_of_tannic_acid.jpg" decoding="async" width="220" height="293" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d0/Bottle_of_tannic_acid.jpg/330px-Bottle_of_tannic_acid.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d0/Bottle_of_tannic_acid.jpg/440px-Bottle_of_tannic_acid.jpg 2x" data-file-width="1944" data-file-height="2592" /></a><figcaption>A bottle of tannic acid (water solution) from the <a href="/wiki/Redwood_tree" class="mw-redirect" title="Redwood tree">redwood tree</a>.</figcaption></figure> <p><b>Tannic acid</b> is a specific form of <a href="/wiki/Tannin" title="Tannin">tannin</a>, a type of <a href="/wiki/Polyphenol" title="Polyphenol">polyphenol</a>. Its weak <a href="/wiki/Acidity" class="mw-redirect" title="Acidity">acidity</a> (<a href="/wiki/Acid_dissociation_constant" title="Acid dissociation constant">pK<sub>a</sub></a> around 6) is due to the numerous <a href="/wiki/Phenol" title="Phenol">phenol</a> groups in the structure. The <a href="/wiki/Chemical_formula" title="Chemical formula">chemical formula</a> for commercial tannic acid is often given as C<sub>76</sub>H<sub>52</sub>O<sub>46</sub>, which corresponds with decagalloyl glucose, but in fact it is a mixture of polygalloyl glucoses or polygalloyl quinic acid esters with the number of <a href="/wiki/Gallic_acid" title="Gallic acid">galloyl</a> moieties per molecule ranging from 2 up to 12 depending on the plant source used to extract the tannic acid. Commercial tannic acid is usually extracted from any of the following plant parts: Tara pods (<i><a href="/wiki/Caesalpinia_spinosa" class="mw-redirect" title="Caesalpinia spinosa">Caesalpinia spinosa</a></i>), gallnuts from <i><a href="/wiki/Rhus_semialata" class="mw-redirect" title="Rhus semialata">Rhus semialata</a></i> or <i><a href="/wiki/Quercus_infectoria" title="Quercus infectoria">Quercus infectoria</a></i> or Sicilian sumac leaves (<i><a href="/wiki/Rhus_coriaria" title="Rhus coriaria">Rhus coriaria</a></i>). </p><p>According to the definitions provided in external references such as international pharmacopoeia, <a href="/wiki/Food_Chemicals_Codex" title="Food Chemicals Codex">Food Chemicals Codex</a> and FAO-WHO tannic acid monograph only tannins obtained from the above-mentioned plants can be considered as tannic acid. Sometimes extracts from <a href="/wiki/Chestnut" title="Chestnut">chestnut</a> or <a href="/wiki/Oak" title="Oak">oak</a> wood are also described as tannic acid but this is an incorrect use of the term. It is a yellow to light brown <a href="/wiki/Amorphous" class="mw-redirect" title="Amorphous">amorphous</a> powder. </p><p>While tannic acid is a specific type of tannin (plant polyphenol), the two terms are sometimes (incorrectly) used interchangeably. The long-standing misuse of the terms, and its inclusion in scholarly articles has compounded the confusion. This is particularly widespread in relation to green tea and black tea, both of which contain many different types of tannins not just exclusively tannic 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> </p><p>Tannic acid is not an appropriate standard for any type of tannin analysis because of its poorly defined composition. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Quercitannic_and_gallotannic_acids">Quercitannic and gallotannic acids</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tannic_acid&action=edit&section=1" title="Edit section: Quercitannic and gallotannic acids"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Quercitannic_acid" title="Quercitannic acid">Quercitannic acid</a> is one of the two forms of tannic 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> found in <a href="/wiki/Oak_bark" class="mw-redirect" title="Oak bark">oak bark</a> and leaves.<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> The other form is called <a href="/wiki/Gallotannic_acid" class="mw-redirect" title="Gallotannic acid">gallotannic acid</a> and is found in oak galls. </p><p>The quercitannic acid molecule is also present in <a href="/wiki/Quercitron" title="Quercitron">quercitron</a>, a yellow dye obtained from the bark of the Eastern black oak (<i>Quercus velutina</i>), a forest tree indigenous in North America. It is described as a yellowish-brown amorphous powder. </p><p>In 1838, <a href="/wiki/J%C3%B6ns_Jacob_Berzelius" title="Jöns Jacob Berzelius">Jöns Jacob Berzelius</a> wrote that quercitannate is used to dissolve morphine.<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> </p><p>In 1865 in the fifth volume of "A dictionary of chemistry", <a href="/wiki/Henry_Watts_(chemist)" title="Henry Watts (chemist)">Henry Watts</a> wrote : </p> <blockquote><p>It exhibits with ferric salts the same reactions as gallotannic acid. It differs however from the latter in not being convertible into <a href="/wiki/Gallic_acid" title="Gallic acid">gallic acid</a>, and not yielding <a href="/wiki/Pyrogallic_acid" class="mw-redirect" title="Pyrogallic acid">pyrogallic acid</a> by dry distillation. It is precipitated by <a href="/wiki/Sulfuric_acid" title="Sulfuric acid">sulfuric acid</a> in red flocks. (<a href="/wiki/John_Stenhouse" title="John Stenhouse">Stenhouse</a>, Ann. Ch. Pharm. xlv. 16.) <br />According to Rochleder (ibid lxiii. 202), the tannic acid of black tea is the same as that of oak-bark.<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></blockquote> <p>In 1880, Etti gave for it the molecular formula C<sub>17</sub>H<sub>16</sub>O<sub>9</sub>. He described it as an unstable substance, having a tendency to give off water to form <a href="/wiki/Anhydride" class="mw-redirect" title="Anhydride">anhydrides</a> (called <a href="/wiki/Phlobaphene" title="Phlobaphene">phlobaphenes</a>), one of which is called <i>oak-red</i> (C<sub>34</sub>H<sub>30</sub>O<sub>17</sub>). For him, it was not a glycoside.<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> </p> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Tannic_acid_ESP.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/02/Tannic_acid_ESP.png/220px-Tannic_acid_ESP.png" decoding="async" width="220" height="210" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/02/Tannic_acid_ESP.png/330px-Tannic_acid_ESP.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/02/Tannic_acid_ESP.png/440px-Tannic_acid_ESP.png 2x" data-file-width="790" data-file-height="754" /></a><figcaption>An electrostatic potential map (blue is positive and red is negative charge) of decagalloyl tannic acid, i.e. a tannic acid derived from ten molecules of gallic acid</figcaption></figure> <p>In Allen's "Commercial Organic Analysis", published in 1912, the formula given was C<sub>19</sub>H<sub>16</sub>O<sub>10</sub>.<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> </p><p>Other authors gave other molecular formulas like C<sub>28</sub>H<sub>26</sub>O<sub>15</sub>, while another formula found is C<sub>28</sub>H<sub>24</sub>O<sub>11</sub>.<sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p><p>According to Lowe, two forms of the principle exist – "one soluble in water, of the formula C<sub>28</sub>H<sub>28</sub>O<sub>14</sub>, and the other scarcely soluble, C<sub>28</sub>H<sub>24</sub>O<sub>12</sub>. Both are changed by the loss of water into oak red, C<sub>28</sub>H<sub>22</sub>O<sub>11</sub>."<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> </p><p>Quercitannic acid was for a time a standard used to assess the phenolic content in <a href="/wiki/Spice" title="Spice">spices</a>, given as <i>quercitannic acid equivalent</i>.<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> </p><p>In an interesting historical note, the inventor of <a href="/wiki/Carborundum" class="mw-redirect" title="Carborundum">carborundum</a>, <a href="/wiki/Edward_G._Acheson" class="mw-redirect" title="Edward G. Acheson">Edward G. Acheson</a>, discovered that gallotannic acid greatly improved the plasticity of clay. In his report of this discovery in 1904 he noted that the only known historical reference to the use of organic material added to clay is the use of straw mixed with clay described in the Bible, Exodus 1:11 and that the Egyptians must have been aware of his (re-)discovery. He stated "This explains why the straw was used and why the children of Israel were successful in substituting stubble for straw, a course that would hardly be possible, were the fibre of the straw depended upon as a bond feasible for the clay, but quite reasonable where the extract of the plant was used."<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Uses">Uses</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tannic_acid&action=edit&section=2" title="Edit section: Uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1251242444">.mw-parser-output .ambox{border:1px solid #a2a9b1;border-left:10px solid #36c;background-color:#fbfbfb;box-sizing:border-box}.mw-parser-output .ambox+link+.ambox,.mw-parser-output .ambox+link+style+.ambox,.mw-parser-output .ambox+link+link+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+style+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+link+.ambox{margin-top:-1px}html body.mediawiki .mw-parser-output .ambox.mbox-small-left{margin:4px 1em 4px 0;overflow:hidden;width:238px;border-collapse:collapse;font-size:88%;line-height:1.25em}.mw-parser-output .ambox-speedy{border-left:10px solid #b32424;background-color:#fee7e6}.mw-parser-output .ambox-delete{border-left:10px solid #b32424}.mw-parser-output .ambox-content{border-left:10px solid #f28500}.mw-parser-output .ambox-style{border-left:10px solid #fc3}.mw-parser-output .ambox-move{border-left:10px solid #9932cc}.mw-parser-output .ambox-protection{border-left:10px solid #a2a9b1}.mw-parser-output .ambox .mbox-text{border:none;padding:0.25em 0.5em;width:100%}.mw-parser-output .ambox .mbox-image{border:none;padding:2px 0 2px 0.5em;text-align:center}.mw-parser-output .ambox .mbox-imageright{border:none;padding:2px 0.5em 2px 0;text-align:center}.mw-parser-output .ambox .mbox-empty-cell{border:none;padding:0;width:1px}.mw-parser-output .ambox .mbox-image-div{width:52px}@media(min-width:720px){.mw-parser-output .ambox{margin:0 10%}}@media print{body.ns-0 .mw-parser-output .ambox{display:none!important}}</style><table class="box-More_citations_needed_section plainlinks metadata ambox ambox-content ambox-Refimprove" role="presentation"><tbody><tr><td class="mbox-image"><div class="mbox-image-div"><span typeof="mw:File"><a href="/wiki/File:Question_book-new.svg" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/9/99/Question_book-new.svg/50px-Question_book-new.svg.png" decoding="async" width="50" height="39" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/9/99/Question_book-new.svg/75px-Question_book-new.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/9/99/Question_book-new.svg/100px-Question_book-new.svg.png 2x" data-file-width="512" data-file-height="399" /></a></span></div></td><td class="mbox-text"><div class="mbox-text-span">This section <b>needs additional citations for <a href="/wiki/Wikipedia:Verifiability" title="Wikipedia:Verifiability">verification</a></b>.<span class="hide-when-compact"> Please help <a href="/wiki/Special:EditPage/Tannic_acid" title="Special:EditPage/Tannic acid">improve this article</a> by <a href="/wiki/Help:Referencing_for_beginners" title="Help:Referencing for beginners">adding citations to reliable sources</a> in this section. Unsourced material may be challenged and removed.</span> <span class="date-container"><i>(<span class="date">July 2016</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> <p>Tannins are a basic ingredient in the chemical staining of <a href="/wiki/Wood" title="Wood">wood</a>, and are already present in woods like <a href="/wiki/Oak" title="Oak">oak</a>, <a href="/wiki/Walnut" title="Walnut">walnut</a>, and <a href="/wiki/Mahogany" title="Mahogany">mahogany</a>. Tannic acid can be applied to woods low in tannin so chemical stains that require tannin content will react. The presence of tannins in the bark of <a href="/wiki/Sequoia_sempervirens" title="Sequoia sempervirens">redwood (<i>Sequoia)</i></a> is a strong natural defense against <a href="/wiki/Wildfire" title="Wildfire">wildfire</a>, <a href="/wiki/Decomposition" title="Decomposition">decomposition</a> and infestation by certain insects such as <a href="/wiki/Termite" title="Termite">termites</a>. It is found in the <a href="/wiki/Seeds" class="mw-redirect" title="Seeds">seeds</a>, <a href="/wiki/Bark_(botany)" title="Bark (botany)">bark</a>, <a href="/wiki/Conifer_cone" title="Conifer cone">cones</a>, and <a href="/wiki/Heartwood" class="mw-redirect" title="Heartwood">heartwood</a>. </p><p>Tannic acid is a common <a href="/wiki/Mordant" title="Mordant">mordant</a> used in the dyeing process for <a href="/wiki/Cellulose" title="Cellulose">cellulose</a> fibers such as <a href="/wiki/Cotton" title="Cotton">cotton</a>, often combined with <a href="/wiki/Alum" title="Alum">alum</a> and/or <a href="/wiki/Iron" title="Iron">iron</a>. The tannin mordant should be done first as metal mordants combine well with the fiber-tannin complex. However this use has lost considerable interest. </p><p>Similarly tannic acid can also be used as an aftertreatment to improve wash fastness properties of acid dyed <a href="/wiki/Polyamide" title="Polyamide">polyamide</a>. It is also an alternative for <a href="/wiki/Fluorocarbon" title="Fluorocarbon">fluorocarbon</a> aftertreatments to impart anti-staining properties to polyamide yarn or carpets. However, due to economic considerations currently the only widespread use as textile auxiliary is the use as an agent to improve chlorine fastness, i.e. resistance against dye bleaching due to cleaning with hypochlorite solutions in high-end polyamide 6,6-based carpets and swimwear. It is, however, used in relatively small quantities for the activation of <a href="/wiki/Upholstery" title="Upholstery">upholstery</a> flock; this serves as an anti-<a href="/wiki/Static_electricity" title="Static electricity">static</a> treatment. </p><p>Tannic acid is used in the conservation of ferrous (iron based) metal objects to passivate and inhibit corrosion. Tannic acid reacts with the corrosion products to form a more stable compound, thus preventing further corrosion from taking place. After treatment the tannic acid residue is generally left on the object so that if moisture reaches the surface the tannic acid will be rehydrated and prevent or slow any corrosion. Tannic acid treatment for conservation is very effective and widely used but it does have a significant visual effect on the object, turning the corrosion products black and any exposed metal dark blue. It should also be used with care on objects with copper alloy components as the tannic acid can have a slight etching effect on these metals. </p><p>Tannic acid is also found in commercially available iron/steel <a href="/wiki/Rust_converter" title="Rust converter">corrosion treatments</a>, such as Hammerite Kurust. </p> <div class="mw-heading mw-heading3"><h3 id="Use_in_food">Use in food</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tannic_acid&action=edit&section=3" title="Edit section: Use in food"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In many parts of the world, its uses in food are permitted. In the <a href="/wiki/United_States" title="United States">United States</a>, tannic acid is <a href="/wiki/Generally_recognized_as_safe" title="Generally recognized as safe">generally recognized as safe</a> by the <a href="/wiki/Food_and_Drug_Administration" title="Food and Drug Administration">Food and Drug Administration</a> for use in baked goods and baking mixes, alcoholic and non-alcoholic beverages, frozen dairy products, soft and hard candy, meat products, and <a href="/wiki/Rendering_(animal_products)" title="Rendering (animal products)">rendered</a> animal fat.<sup id="cite_ref-fda-gras_15-0" class="reference"><a href="#cite_note-fda-gras-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> </p><p>According to <a href="/wiki/Directive_(European_Union)" title="Directive (European Union)">EU directive</a> 89/107/EEC, tannic acid cannot be considered as a <a href="/wiki/Food_additive" title="Food additive">food additive</a> and consequently does not hold an <a href="/wiki/E_number" title="E number">E number</a>.<sup id="cite_ref-efsa_16-0" class="reference"><a href="#cite_note-efsa-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> Under directive 89/107/EEC, tannic acid can be referred to as a food ingredient. The E-number E181 is sometimes incorrectly used to refer to tannic acid; this in fact refers to the <a href="/wiki/INS_number" class="mw-redirect" title="INS number">INS number</a> assigned to tannic acid under the FAO-WHO Codex Alimentarius system.<sup id="cite_ref-efsa_16-1" class="reference"><a href="#cite_note-efsa-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Uses_as_a_medication">Uses as a medication</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tannic_acid&action=edit&section=4" title="Edit section: Uses as a medication"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In conjunction with magnesium and sometimes activated charcoal, tannic acid was once used as a treatment for many toxic substances, such as <a href="/wiki/Strychnine" title="Strychnine">strychnine</a>, mushroom, and ptomaine poisonings in the late 19th and early 20th centuries.<sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </p><p>The introduction of tannic acid treatment of severe burn injuries in the 1920s significantly reduced mortality rates.<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> During <a href="/wiki/World_War_I" title="World War I">World War I</a>, tannic acid dressings were prescribed to treat "burns, whether caused by incendiary bombs, <a href="/wiki/Mustard_gas" title="Mustard gas">mustard gas</a>, or <a href="/wiki/Lewisite" title="Lewisite">lewisite</a>".<sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> After the war this use was abandoned due to the development of more modern treatment regimens. </p> <div class="mw-heading mw-heading2"><h2 id="Hazards">Hazards</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tannic_acid&action=edit&section=5" title="Edit section: Hazards"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Tannic acid could cause potential health hazards such as damage to the eye, skin, respiratory tract, and gastrointestinal tract. It may cause irritation, redness, pain, blurred vision, and possible eye damage. When tannic acid is absorbed through the skin in harmful amounts, it may cause irritation, redness, and pain. Nausea, vomiting and diarrhoea are symptoms of tannic acid ingestion and prolonged exposure may cause liver damage. Upon inhalation, tannic acid may cause respiratory tract irritation.<sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Crocodilian_coloration">Crocodilian coloration</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tannic_acid&action=edit&section=6" title="Edit section: Crocodilian coloration"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Skin color in <a href="/wiki/Crocodilia" title="Crocodilia">Crocodilia</a> (crocodiles and alligators) is very dependent on water quality. Algae-laden waters produce greener skin, while tannic acid in the water from decay of leaves from overhanging trees (which produces some types of <a href="/wiki/Blackwater_river" title="Blackwater river">blackwater rivers</a>) often produce darker skin in these animals.<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> </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=Tannic_acid&action=edit&section=7" 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-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</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 class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.acs.org/content/acs/en/molecule-of-the-week/archive/t/tannic-acid.html">"Tannic acid"</a>. <i>American Chemical Society</i>. 15 January 2018.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=American+Chemical+Society&rft.atitle=Tannic+acid&rft.date=2018-01-15&rft_id=https%3A%2F%2Fwww.acs.org%2Fcontent%2Facs%2Fen%2Fmolecule-of-the-week%2Farchive%2Ft%2Ftannic-acid.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATannic+acid" class="Z3988"></span></span> </li> <li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text"><link 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(December 2013)">page needed</span></a></i>]</sup></span> </li> <li id="cite_note-7"><span class="mw-cite-backlink"><b><a href="#cite_ref-7">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWatts1868" class="citation book cs1">Watts, Henry (1868). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=J9fokzIF4NMC&pg=PA6"><i>A Dictionary of chemistry and the allied branches of other sciences</i></a>. Vol. 5. 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.hlist td ol,.mw-parser-output .navbox .hlist td ul,.mw-parser-output .navbox td.hlist dl,.mw-parser-output .navbox td.hlist ol,.mw-parser-output .navbox td.hlist ul{padding:0.125em 0}.mw-parser-output .navbox .navbar{display:block;font-size:100%}.mw-parser-output .navbox-title .navbar{float:left;text-align:left;margin-right:0.5em}body.skin--responsive .mw-parser-output .navbox-image img{max-width:none!important}@media print{body.ns-0 .mw-parser-output .navbox{display:none!important}}</style><style data-mw-deduplicate="TemplateStyles:r886047488">.mw-parser-output .nobold{font-weight:normal}</style><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r886047488"></div><div role="navigation" class="navbox" aria-labelledby="Types_of_gallotannins245" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><style data-mw-deduplicate="TemplateStyles:r1239400231">.mw-parser-output .navbar{display:inline;font-size:88%;font-weight:normal}.mw-parser-output .navbar-collapse{float:left;text-align:left}.mw-parser-output .navbar-boxtext{word-spacing:0}.mw-parser-output .navbar ul{display:inline-block;white-space:nowrap;line-height:inherit}.mw-parser-output .navbar-brackets::before{margin-right:-0.125em;content:"[ "}.mw-parser-output .navbar-brackets::after{margin-left:-0.125em;content:" ]"}.mw-parser-output .navbar li{word-spacing:-0.125em}.mw-parser-output .navbar a>span,.mw-parser-output .navbar a>abbr{text-decoration:inherit}.mw-parser-output .navbar-mini abbr{font-variant:small-caps;border-bottom:none;text-decoration:none;cursor:inherit}.mw-parser-output .navbar-ct-full{font-size:114%;margin:0 7em}.mw-parser-output .navbar-ct-mini{font-size:114%;margin:0 4em}html.skin-theme-clientpref-night .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}@media(prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}}@media print{.mw-parser-output .navbar{display:none!important}}</style><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Gallotannin" title="Template:Gallotannin"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Gallotannin" title="Template talk:Gallotannin"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Gallotannin" title="Special:EditPage/Template:Gallotannin"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Types_of_gallotannins245" style="font-size:114%;margin:0 4em">Types of <a href="/wiki/Gallotannin" title="Gallotannin">gallotannins</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">Aglycones</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Digallic_acid" title="Digallic acid">Digallic acid</a></li> <li><a href="/wiki/Gallic_acid" title="Gallic acid">Gallic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Galloylglucoses</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><span class="nobold"><a href="/w/index.php?title=Monogalloylglucose&action=edit&redlink=1" class="new" title="Monogalloylglucose (page does not exist)">Monogalloylglucoses</a>:</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/1-Galloylglucose" class="mw-redirect" title="1-Galloylglucose">1-Galloylglucose</a> <ul><li>Glucogallin</li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><span class="nobold"><a href="/wiki/Digalloylglucose" title="Digalloylglucose">Digalloylglucoses</a>:</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/1,6-Digalloylglucose" title="1,6-Digalloylglucose">1,6-Digalloylglucose</a></li> <li><a href="/w/index.php?title=2,6-Digalloylglucose&action=edit&redlink=1" class="new" title="2,6-Digalloylglucose (page does not exist)">2,6-Digalloylglucose</a></li> <li><a href="/w/index.php?title=3,6-Digalloylglucose&action=edit&redlink=1" class="new" title="3,6-Digalloylglucose (page does not exist)">3,6-Digalloylglucose</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><span class="nobold"><a href="/wiki/Trigalloylglucose" title="Trigalloylglucose">Trigalloylglucoses</a>:</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=1,2,3-Trigalloylglucose&action=edit&redlink=1" class="new" title="1,2,3-Trigalloylglucose (page does not exist)">1,2,3-Trigalloylglucose</a> <ul><li><a href="/w/index.php?title=1,2,3-Tri-O-galloyl-%CE%B2-D-glucose&action=edit&redlink=1" class="new" title="1,2,3-Tri-O-galloyl-β-D-glucose (page does not exist)">1,2,3-Tri-O-galloyl-β-D-glucose</a></li></ul></li> <li><a href="/wiki/1,2,6-Trigalloylglucose" title="1,2,6-Trigalloylglucose">1,2,6-Trigalloylglucose</a></li> <li><a href="/wiki/1,3,6-Trigalloylglucose" title="1,3,6-Trigalloylglucose">1,3,6-Trigalloylglucose</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><span class="nobold"><a href="/w/index.php?title=Tetragalloylglucose&action=edit&redlink=1" class="new" title="Tetragalloylglucose (page does not exist)">Tetragalloylglucoses</a>:</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=1,2,3,6-Tetragalloylglucose&action=edit&redlink=1" class="new" title="1,2,3,6-Tetragalloylglucose (page does not exist)">1,2,3,6-Tetragalloylglucose</a> <ul><li><a href="/w/index.php?title=1,2,3,6-Tetrakis-O-galloyl-%CE%B2-D-glucose&action=edit&redlink=1" class="new" title="1,2,3,6-Tetrakis-O-galloyl-β-D-glucose (page does not exist)">1,2,3,6-Tetrakis-O-galloyl-β-D-glucose</a></li></ul></li> <li><a href="/w/index.php?title=1,2,4,6-Tetragalloylglucose&action=edit&redlink=1" class="new" title="1,2,4,6-Tetragalloylglucose (page does not exist)">1,2,4,6-Tetragalloylglucose</a> <ul><li><a href="/w/index.php?title=1,2,4,6-Tetrakis-O-galloyl-%CE%B2-D-glucose&action=edit&redlink=1" class="new" title="1,2,4,6-Tetrakis-O-galloyl-β-D-glucose (page does not exist)">1,2,4,6-Tetrakis-O-galloyl-β-D-glucose</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><span class="nobold"><a href="/wiki/Pentagalloylglucose" title="Pentagalloylglucose">Pentagalloylglucoses</a>:</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/1,2,3,4,6-Pentagalloylglucose" class="mw-redirect" title="1,2,3,4,6-Pentagalloylglucose">1,2,3,4,6-Pentagalloylglucose</a></li> <li><a href="/w/index.php?title=6-Digalloyl-1,2,3-trigalloylglucose&action=edit&redlink=1" class="new" title="6-Digalloyl-1,2,3-trigalloylglucose (page does not exist)">6-Digalloyl-1,2,3-trigalloylglucose</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">other</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=Hexagalloylglucose&action=edit&redlink=1" class="new" title="Hexagalloylglucose (page does not exist)">Hexagalloylglucose</a></li> <li><a href="/w/index.php?title=Heptagalloylglucose&action=edit&redlink=1" class="new" title="Heptagalloylglucose (page does not exist)">Heptagalloylglucose</a></li> <li><a href="/w/index.php?title=Octagalloylglucose&action=edit&redlink=1" class="new" title="Octagalloylglucose (page does not exist)">Octagalloylglucose</a></li> <li><a href="/w/index.php?title=Nonagalloylglucose&action=edit&redlink=1" class="new" title="Nonagalloylglucose (page does not exist)">Nonagalloylglucose</a></li> <li><a class="mw-selflink selflink">Decagalloylglucose</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><span class="nobold"><a href="/w/index.php?title=Galloylquinic_acid&action=edit&redlink=1" class="new" title="Galloylquinic acid (page does not exist)">Galloylquinic acids</a>:</span></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><span class="nobold"><a href="/w/index.php?title=Monogalloylquinic_acid&action=edit&redlink=1" class="new" title="Monogalloylquinic acid (page does not exist)">Monogalloylquinic acids</a>:</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/3-O-Galloylquinic_acid" class="mw-redirect" title="3-O-Galloylquinic acid">3-O-Galloylquinic acid</a> <ul><li>Theogallin</li></ul></li> <li><a href="/w/index.php?title=4-O-Galloylquinic_acid&action=edit&redlink=1" class="new" title="4-O-Galloylquinic acid (page does not exist)">4-O-Galloylquinic acid</a></li> <li><a href="/w/index.php?title=5-O-Galloylquinic_acid&action=edit&redlink=1" class="new" title="5-O-Galloylquinic acid (page does not exist)">5-O-Galloylquinic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><span class="nobold"><a href="/w/index.php?title=Digalloylquinic_acid&action=edit&redlink=1" class="new" title="Digalloylquinic acid (page does not exist)">Digalloylquinic acids</a>:</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=1,4-Di-O-galloylquinic_acid&action=edit&redlink=1" class="new" title="1,4-Di-O-galloylquinic acid (page does not exist)">1,4-Di-O-galloylquinic acid</a></li> <li><a href="/w/index.php?title=3,4-Di-O-Galloylquinic_acid&action=edit&redlink=1" class="new" title="3,4-Di-O-Galloylquinic acid (page does not exist)">3,4-Di-O-Galloylquinic acid</a></li> <li><a href="/w/index.php?title=3,5-Di-O-Galloylquinic_acid&action=edit&redlink=1" class="new" title="3,5-Di-O-Galloylquinic acid (page does not exist)">3,5-Di-O-Galloylquinic acid</a></li> <li><a href="/w/index.php?title=4,5-Di-O-Galloylquinic_acid&action=edit&redlink=1" class="new" title="4,5-Di-O-Galloylquinic acid (page does not exist)">4,5-Di-O-Galloylquinic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><span class="nobold"><a href="/w/index.php?title=Trigalloylquinic_acid&action=edit&redlink=1" class="new" title="Trigalloylquinic acid (page does not exist)">Trigalloylquinic acids</a>:</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=1,3,4-Tri-O-galloylquinic_acid&action=edit&redlink=1" class="new" title="1,3,4-Tri-O-galloylquinic acid (page does not exist)">1,3,4-Tri-O-galloylquinic acid</a></li> <li><a href="/wiki/3,4,5-Tri-O-galloylquinic_acid" title="3,4,5-Tri-O-galloylquinic acid">3,4,5-Tri-O-galloylquinic acid</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><span class="nobold"><a href="/w/index.php?title=Galloylshikimic_acid&action=edit&redlink=1" class="new" title="Galloylshikimic acid (page does not exist)">Galloylshikimic acids</a>:</span></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=4-O-Galloylshikimic_acid&action=edit&redlink=1" class="new" title="4-O-Galloylshikimic acid (page does not exist)">4-O-Galloylshikimic acid</a></li> <li><a href="/w/index.php?title=5-O-Galloylshikimic_acid&action=edit&redlink=1" class="new" title="5-O-Galloylshikimic acid (page does not exist)">5-O-Galloylshikimic acid</a></li> <li><a href="/w/index.php?title=3,5-Di-O-galloylshikimic_acid&action=edit&redlink=1" class="new" title="3,5-Di-O-galloylshikimic acid (page does not exist)">3,5-Di-O-galloylshikimic acid</a></li> <li><a href="/w/index.php?title=3,4,5-Tri-O-galloylshikimic_acid&action=edit&redlink=1" class="new" title="3,4,5-Tri-O-galloylshikimic acid (page does not exist)">3,4,5-Tri-O-galloylshikimic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">others</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=1,2,6-Trigalloylalloside&action=edit&redlink=1" class="new" title="1,2,6-Trigalloylalloside (page does not exist)">1,2,6-Trigalloylalloside</a></li> <li><a href="/w/index.php?title=1,3,6-Trigalloylalloside&action=edit&redlink=1" class="new" title="1,3,6-Trigalloylalloside (page does not exist)">1,3,6-Trigalloylalloside</a></li> <li><a href="/w/index.php?title=1,2,3,6-Tetragalloylalloside&action=edit&redlink=1" class="new" title="1,2,3,6-Tetragalloylalloside (page does not exist)">1,2,3,6-Tetragalloylalloside</a></li> <li><a href="/w/index.php?title=1-O-Galloylquercitol&action=edit&redlink=1" class="new" title="1-O-Galloylquercitol (page does not exist)">1-O-Galloylquercitol</a></li> <li><a href="/w/index.php?title=1,4-Di-O-galloylquercitol&action=edit&redlink=1" class="new" title="1,4-Di-O-galloylquercitol (page does not exist)">1,4-Di-O-galloylquercitol</a></li></ul> </div></td></tr></tbody></table></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?useformat=desktop&type=1x1&usesul3=0" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Retrieved from "<a dir="ltr" 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