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<span>Toggle Metabolism subsection</span> </button> <ul id="toc-Metabolism-sublist" class="vector-toc-list"> <li id="toc-Biosynthesis" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Biosynthesis"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.1</span> <span>Biosynthesis</span> </div> </a> <ul id="toc-Biosynthesis-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Biodegradation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Biodegradation"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.2</span> <span>Biodegradation</span> </div> </a> <ul id="toc-Biodegradation-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Metabolism_in_humans" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Metabolism_in_humans"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.3</span> <span>Metabolism in humans</span> </div> </a> <ul id="toc-Metabolism_in_humans-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Biotransformation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Biotransformation"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.4</span> <span>Biotransformation</span> </div> </a> <ul id="toc-Biotransformation-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Glycosides" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Glycosides"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.5</span> <span>Glycosides</span> </div> </a> <ul id="toc-Glycosides-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Research" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Research"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Research</span> </div> </a> <button aria-controls="toc-Research-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 Research subsection</span> </button> <ul id="toc-Research-sublist" class="vector-toc-list"> <li id="toc-Vascular_function" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Vascular_function"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.1</span> <span>Vascular function</span> </div> </a> <ul id="toc-Vascular_function-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Adverse_events" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Adverse_events"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.2</span> <span>Adverse events</span> </div> </a> <ul id="toc-Adverse_events-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Other" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Other"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.3</span> <span>Other</span> </div> </a> <ul id="toc-Other-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Botanical_effects" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Botanical_effects"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Botanical effects</span> </div> </a> <ul id="toc-Botanical_effects-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">6</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">7</span> <span>External links</span> </div> </a> <ul id="toc-External_links-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " 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Available in 19 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-19" 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">19 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/%D9%83%D8%A7%D8%AA%D9%8A%D8%B4%D9%8A%D9%86" title="كاتيشين – Arabic" lang="ar" hreflang="ar" data-title="كاتيشين" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%DA%A9%D8%A7%D8%AA%DA%86%DB%8C%D9%86" title="کاتچین – South Azerbaijani" lang="azb" hreflang="azb" data-title="کاتچین" 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/Catequina" title="Catequina – Catalan" lang="ca" hreflang="ca" data-title="Catequina" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Catequina" title="Catequina – Spanish" lang="es" hreflang="es" data-title="Catequina" 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/Katekino" title="Katekino – Esperanto" lang="eo" hreflang="eo" data-title="Katekino" 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/Katekina" title="Katekina – Basque" lang="eu" hreflang="eu" data-title="Katekina" 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/%DA%A9%D8%A7%D8%AA%DA%86%DB%8C%D9%86" title="کاتچین – Persian" lang="fa" hreflang="fa" data-title="کاتچین" 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/Cat%C3%A9chine" title="Catéchine – French" lang="fr" hreflang="fr" data-title="Catéchine" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EC%B9%B4%ED%85%8C%ED%82%A8" title="카테킨 – Korean" lang="ko" hreflang="ko" data-title="카테킨" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D4%BF%D5%A1%D5%BF%D5%A5%D5%AD%D5%AB%D5%B6%D5%B6%D5%A5%D6%80" title="Կատեխիններ – Armenian" lang="hy" hreflang="hy" data-title="Կատեխիններ" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Catechina" title="Catechina – Italian" lang="it" hreflang="it" data-title="Catechina" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%AB%E3%83%86%E3%82%AD%E3%83%B3" title="カテキン – Japanese" lang="ja" hreflang="ja" data-title="カテキン" 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-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Catequina" title="Catequina – Portuguese" lang="pt" hreflang="pt" data-title="Catequina" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Katehin" title="Katehin – Serbian" lang="sr" hreflang="sr" data-title="Katehin" 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/Katehin" title="Katehin – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Katehin" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Katekiini" title="Katekiini – Finnish" lang="fi" hreflang="fi" data-title="Katekiini" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%9A%D0%B0%D1%82%D0%B5%D1%85%D1%96%D0%BD%D0%B8" title="Катехіни – Ukrainian" lang="uk" hreflang="uk" data-title="Катехіни" 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/Catechin" title="Catechin – Vietnamese" lang="vi" hreflang="vi" data-title="Catechin" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target"><span>Tiếng Việt</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E5%84%BF%E8%8C%B6%E7%B4%A0" title="儿茶素 – Chinese" lang="zh" hreflang="zh" data-title="儿茶素" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target"><span>中文</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span 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dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Type of natural phenol as a plant secondary metabolite</div> <style data-mw-deduplicate="TemplateStyles:r1084375498">.mw-parser-output .ib-chembox{border-collapse:collapse;text-align:left}.mw-parser-output .ib-chembox td,.mw-parser-output .ib-chembox th{border:1px solid #a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}</style> <table class="infobox ib-chembox"> <caption>Catechin </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Catechin_structure.svg" class="mw-file-description" title="Chemical structure of (+)-Catechin"><img alt="Chemical structure of (+)-Catechin" src="//upload.wikimedia.org/wikipedia/commons/thumb/d/db/Catechin_structure.svg/220px-Catechin_structure.svg.png" decoding="async" width="220" height="117" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/db/Catechin_structure.svg/330px-Catechin_structure.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/db/Catechin_structure.svg/440px-Catechin_structure.svg.png 2x" data-file-width="490" data-file-height="260" /></a></span> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:(%2B)-catechin-from-xtal-3D-bs-17.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f3/%28%2B%29-catechin-from-xtal-3D-bs-17.png/220px-%28%2B%29-catechin-from-xtal-3D-bs-17.png" decoding="async" width="220" height="186" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f3/%28%2B%29-catechin-from-xtal-3D-bs-17.png/330px-%28%2B%29-catechin-from-xtal-3D-bs-17.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f3/%28%2B%29-catechin-from-xtal-3D-bs-17.png/440px-%28%2B%29-catechin-from-xtal-3D-bs-17.png 2x" data-file-width="2779" data-file-height="2347" /></a></span> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Chemical_nomenclature" title="Chemical nomenclature">IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">(2<i>R</i>,3<i>S</i>)-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-2<i>H</i>-chromene-3,5,7-triol</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;">Cianidanol<br />Cyanidanol<br />(+)-catechin<br />D-Catechin<br />Catechinic acid<br />Catechuic acid<br />Cianidol<br />Dexcyanidanol<br />(2<i>R</i>,3<i>S</i>)-Catechin<br />2,3-<i>trans</i>-Catechin<br /> (2<i>R</i>,3<i>S</i>)-Flavan-3,3′,4′,5,7-pentol</div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=7295-85-4">7295-85-4</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><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=154-23-4">154-23-4</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><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=18829-70-4">18829-70-4</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><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=88191-48-4">88191-48-4</a></span> (+), hydrate<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;">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=Oc1ccc%28cc1O%29%5BC%40H%5D3Oc2cc%28O%29cc%28O%29c2C%5BC%40%40H%5D3O">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td>3DMet </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.3dmet.dna.affrc.go.jp"><a rel="nofollow" class="external text" href="http://www.3dmet.dna.affrc.go.jp/cgi/show_data.php?acc=B02102">B02102</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=15600">CHEBI:15600</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/ChEMBL206452">ChEMBL206452</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.8711.html">8711</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a> </td> <td><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.005.297">100.005.297</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q415007#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span> </td></tr> <tr> <td><a href="/wiki/European_Community_number" title="European Community number"><span title="European Community number (chemical identifier)">EC Number</span></a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>205-825-1</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/C06562">C06562</a></span></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/9064">9064</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/5J4Y243W61">5J4Y243W61</a></span> (±)<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/8R1V1STN48">8R1V1STN48</a></span> (+)<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/FHB0GX3D44">FHB0GX3D44</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/DTXSID3022322">DTXSID3022322</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q415007#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></span></li></ul></div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15+/m0/s1<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: PFTAWBLQPZVEMU-DZGCQCFKSA-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/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15+/m0/s1</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: PFTAWBLQPZVEMU-DZGCQCFKBX</div></div></li></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">Oc1ccc(cc1O)[C@H]3Oc2cc(O)cc(O)c2C[C@@H]3O</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td><span title="Carbon">C</span><sub>15</sub><span title="Hydrogen">H</span><sub>14</sub><span title="Oxygen">O</span><sub>6</sub> </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td><span class="nowrap"><span data-sort-value="7002290271000000000♠"></span>290.271</span> g·mol<sup>−1</sup>   </td></tr> <tr> <td>Appearance </td> <td>Colorless solid </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>175 to 177 °C (347 to 351 °F; 448 to 450 K) </td></tr> <tr> <td><a href="/wiki/Ultraviolet%E2%80%93visible_spectroscopy" title="Ultraviolet–visible spectroscopy">UV-vis</a> (λ<sub>max</sub>) </td> <td>276 nm </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Specific_rotation" title="Specific rotation">Chiral rotation</a> ([α]<sub>D</sub>)</div> </td> <td>+14.0° </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Hazards </th></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;"><b><a href="/wiki/Occupational_safety_and_health" title="Occupational safety and health">Occupational safety and health</a></b> (OHS/OSH): </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Main hazards</div> </td> <td>Mutagenic for mammalian somatic cells, mutagenic for bacteria and yeast </td></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;"><a href="/wiki/Globally_Harmonized_System_of_Classification_and_Labelling_of_Chemicals" title="Globally Harmonized System of Classification and Labelling of Chemicals"><b>GHS</b> labelling</a>: </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_hazard_pictograms" title="GHS hazard pictograms">Pictograms</a></div> </td> <td><span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-exclam.svg" class="mw-file-description" title="GHS07: Exclamation mark"><img alt="GHS07: Exclamation mark" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/50px-GHS-pictogram-exclam.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/75px-GHS-pictogram-exclam.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/100px-GHS-pictogram-exclam.svg.png 2x" data-file-width="512" data-file-height="512" /></a></span> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Globally_Harmonized_System_of_Classification_and_Labelling_of_Chemicals#Signal_word" title="Globally Harmonized System of Classification and Labelling of Chemicals">Signal word</a></div> </td> <td><b>Warning</b> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_hazard_statements" title="GHS hazard statements">Hazard statements</a></div> </td> <td><abbr class="abbr" title="H315: Causes skin irritation">H315</abbr>, <abbr class="abbr" title="H319: Causes serious eye irritation">H319</abbr>, <abbr class="abbr" title="H335: May cause respiratory irritation">H335</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="P261: Avoid breathing dust/fume/gas/mist/vapours/spray.">P261</abbr>, <abbr class="abbr" title="P264: Wash ... thoroughly after handling.">P264</abbr>, <abbr class="abbr" title="P271: Use only outdoors or in a well-ventilated area.">P271</abbr>, <abbr class="abbr" title="P280: Wear protective gloves/protective clothing/eye protection/face protection.">P280</abbr>, <abbr class="abbr" title="P302+P352: IF ON SKIN: Wash with soap and water.">P302+P352</abbr>, <abbr class="abbr" title="P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing.">P304+P340</abbr>, <abbr class="abbr" title="P305+P351+P338: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do. Continue rinsing.">P305+P351+P338</abbr>, <abbr class="abbr" title="P312: Call a POISON CENTER or doctor/physician if you feel unwell.">P312</abbr>, <abbr class="abbr" title="P321: Specific treatment (see ... on this label).">P321</abbr>, <abbr class="abbr" title="P332+P313: If skin irritation occurs: Get medical advice/attention.">P332+P313</abbr>, <abbr class="abbr" title="P337+P313: If eye irritation persists: Get medical advice/attention.">P337+P313</abbr>, <abbr class="abbr" title="P362: Take off contaminated clothing.">P362</abbr>, <abbr class="abbr" title="P403+P233: Store in a well ventilated place. Keep container tightly closed.">P403+P233</abbr>, <abbr class="abbr" title="P405: Store locked up.">P405</abbr>, <abbr class="abbr" title="P501: Dispose of contents/container to ...">P501</abbr> </td></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;"><b>Lethal dose</b> or concentration (LD, LC): </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">LD<sub>50</sub> (<a href="/wiki/Lethal_dose#LD50" title="Lethal dose">median dose</a>)</div> </td> <td>(+)-catechin : 10,000 mg/kg in rat (RTECS)<br />10,000 mg/kg in mouse<br />3,890 mg/kg in rat (other source) </td></tr> <tr> <td><a href="/wiki/Safety_data_sheet" title="Safety data sheet">Safety data sheet</a> (SDS) </td> <td><a rel="nofollow" class="external text" href="https://web.archive.org/web/20131007063424/http://www.sciencelab.com/msds.php?msdsId=9923337">sciencelab</a> <a rel="nofollow" class="external text" href="http://www.applichem.com/fileadmin/datenblaetter/A4325_GB.pdf">AppliChem</a><sup class="noprint Inline-Template"><span style="white-space: nowrap;">[<i><a href="/wiki/Wikipedia:Link_rot" title="Wikipedia:Link rot"><span title=" Dead link tagged August 2017">permanent dead link</span></a></i><span style="visibility:hidden; color:transparent; padding-left:2px">‍</span>]</span></sup> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Pharmacology </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Route_of_administration" title="Route of administration">Routes of<br />administration</a></div> </td> <td>Oral </td></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;"><a href="/wiki/Pharmacokinetics" title="Pharmacokinetics">Pharmacokinetics</a>: </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Excretion" title="Excretion">Excretion</a></div> </td> <td>Urines </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"><div style="text-align:center;"><span typeof="mw:File"><span><img alt="☒" 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=455522430&page2=Catechin">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>Catechin</b> <span class="rt-commentedText nowrap"><span class="IPA nopopups noexcerpt" lang="en-fonipa"><a href="/wiki/Help:IPA/English" title="Help:IPA/English">/<span style="border-bottom:1px dotted"><span title="/ˈ/: primary stress follows">ˈ</span><span title="'k' in 'kind'">k</span><span title="/æ/: 'a' in 'bad'">æ</span><span title="'t' in 'tie'">t</span><span title="/ɪ/: 'i' in 'kit'">ɪ</span><span title="'k' in 'kind'">k</span><span title="/ɪ/: 'i' in 'kit'">ɪ</span><span title="'n' in 'nigh'">n</span></span>/</a></span></span> is a <a href="/wiki/Flavan-3-ol" title="Flavan-3-ol">flavan-3-ol</a>, a type of <a href="/wiki/Secondary_metabolite" title="Secondary metabolite">secondary metabolite</a> providing <a href="/wiki/Antioxidant" title="Antioxidant">antioxidant</a> roles in <a href="/wiki/Plant" title="Plant">plants</a>. It belongs to the subgroup of <a href="/wiki/Polyphenol" title="Polyphenol">polyphenols</a> called <a href="/wiki/Flavonoids" class="mw-redirect" title="Flavonoids">flavonoids</a>. </p><p>The name of the catechin chemical family derives from <i><a href="/wiki/Catechu" title="Catechu">catechu</a></i>, which is the tannic juice or boiled extract of <i>Mimosa catechu</i> (<i><a href="/wiki/Acacia_catechu" class="mw-redirect" title="Acacia catechu">Acacia catechu</a></i> L.f).<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> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Chemistry">Chemistry</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Catechin&action=edit&section=1" title="Edit section: Chemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:Catechin_numbered.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/16/Catechin_numbered.svg/220px-Catechin_numbered.svg.png" decoding="async" width="220" height="127" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/16/Catechin_numbered.svg/330px-Catechin_numbered.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/16/Catechin_numbered.svg/440px-Catechin_numbered.svg.png 2x" data-file-width="665" data-file-height="385" /></a><figcaption>Catechin numbered</figcaption></figure> <p>Catechin possesses two <a href="/wiki/Benzene_ring" class="mw-redirect" title="Benzene ring">benzene rings</a> (called the A and B rings) and a <a href="/wiki/Dihydropyran" title="Dihydropyran">dihydropyran</a> heterocycle (the C ring) with a <a href="/wiki/Hydroxyl_group" class="mw-redirect" title="Hydroxyl group">hydroxyl group</a> on carbon 3. The A ring is similar to a <a href="/wiki/Resorcinol" title="Resorcinol">resorcinol</a> moiety while the B ring is similar to a <a href="/wiki/Catechol" title="Catechol">catechol</a> moiety. There are two <a href="/wiki/Chirality_(chemistry)" title="Chirality (chemistry)">chiral</a> centers on the molecule on carbons 2 and 3. Therefore, it has four <a href="/wiki/Diastereoisomer" class="mw-redirect" title="Diastereoisomer">diastereoisomers</a>. Two of the isomers are in <a href="/wiki/Trans_configuration" class="mw-redirect" title="Trans configuration"><i>trans</i> configuration</a> and are called <i>catechin</i> and the other two are in <a href="/wiki/Cis_configuration" class="mw-redirect" title="Cis configuration"><i>cis</i> configuration</a> and are called <i>epicatechin</i>. </p><p>The most common catechin isomer is (+)-catechin. The other <a href="/wiki/Stereoisomer" class="mw-redirect" title="Stereoisomer">stereoisomer</a> is (−)-catechin or <i>ent</i>-catechin. The most common epicatechin isomer is (−)-epicatechin (also known under the names <small>L</small>-epicatechin, epicatechol, (−)-epicatechol, <small>L</small>-acacatechin, <small>L</small>-epicatechol, epicatechin, 2,3-<i>cis</i>-epicatechin or (2<i>R</i>,3<i>R</i>)-(−)-epicatechin). </p><p>The different epimers can be separated using <a href="/wiki/Chiral_column_chromatography" title="Chiral column chromatography">chiral column chromatography</a>.<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> </p><p>Making reference to no particular isomer, the molecule can just be called catechin. Mixtures of the different enantiomers can be called (±)-catechin or <small>DL</small>-catechin and (±)-epicatechin or <small>DL</small>-epicatechin. </p><p>Catechin and epicatechin are the building blocks of the <a href="/wiki/Proanthocyanidin" title="Proanthocyanidin">proanthocyanidins</a>, a type of condensed tannin. </p> <ul class="gallery mw-gallery-traditional" style="max-width: 486px;"> <li class="gallerycaption">Diastereoisomers gallery</li> <li class="gallerybox" style="width: 235px"> <div class="thumb" style="width: 230px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:(%2B)-Catechin.png" class="mw-file-description" title="(+)-catechin (2R,3S)"><img alt="(+)-catechin (2R,3S)" src="//upload.wikimedia.org/wikipedia/commons/thumb/4/44/%28%2B%29-Catechin.png/200px-%28%2B%29-Catechin.png" decoding="async" width="200" height="109" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/44/%28%2B%29-Catechin.png/300px-%28%2B%29-Catechin.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/44/%28%2B%29-Catechin.png/400px-%28%2B%29-Catechin.png 2x" data-file-width="1071" data-file-height="582" /></a></span></div> <div class="gallerytext">(+)-catechin (2<i>R</i>,3<i>S</i>)</div> </li> <li class="gallerybox" style="width: 235px"> <div class="thumb" style="width: 230px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Catechin.png" class="mw-file-description" title="(−)-catechin (2S,3R)"><img alt="(−)-catechin (2S,3R)" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Catechin.png/200px-Catechin.png" decoding="async" width="200" height="109" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Catechin.png/300px-Catechin.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Catechin.png/400px-Catechin.png 2x" data-file-width="1071" data-file-height="582" /></a></span></div> <div class="gallerytext">(−)-catechin (2<i>S</i>,3<i>R</i>)</div> </li> <li class="gallerybox" style="width: 235px"> <div class="thumb" style="width: 230px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:(-)-Epicatechin.svg" class="mw-file-description" title="(−)-epicatechin (2R,3R)"><img alt="(−)-epicatechin (2R,3R)" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/2b/%28-%29-Epicatechin.svg/200px-%28-%29-Epicatechin.svg.png" decoding="async" width="200" height="112" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/2b/%28-%29-Epicatechin.svg/300px-%28-%29-Epicatechin.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/2b/%28-%29-Epicatechin.svg/400px-%28-%29-Epicatechin.svg.png 2x" data-file-width="369" data-file-height="206" /></a></span></div> <div class="gallerytext">(−)-epicatechin (2<i>R</i>,3<i>R</i>)</div> </li> <li class="gallerybox" style="width: 235px"> <div class="thumb" style="width: 230px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:(%2B)-epicatechin.svg" class="mw-file-description" title="(+)-epicatechin (2S,3S)"><img alt="(+)-epicatechin (2S,3S)" src="//upload.wikimedia.org/wikipedia/commons/thumb/8/82/%28%2B%29-epicatechin.svg/200px-%28%2B%29-epicatechin.svg.png" decoding="async" width="200" height="114" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/82/%28%2B%29-epicatechin.svg/300px-%28%2B%29-epicatechin.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/82/%28%2B%29-epicatechin.svg/400px-%28%2B%29-epicatechin.svg.png 2x" data-file-width="660" data-file-height="375" /></a></span></div> <div class="gallerytext">(+)-epicatechin (2<i>S</i>,3<i>S</i>)</div> </li> </ul> <figure class="mw-default-size mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:Catechin_above.PNG" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b5/Catechin_above.PNG/220px-Catechin_above.PNG" decoding="async" width="220" height="70" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b5/Catechin_above.PNG/330px-Catechin_above.PNG 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b5/Catechin_above.PNG/440px-Catechin_above.PNG 2x" data-file-width="939" data-file-height="297" /></a><figcaption>3D view of "pseudoequatorial" (<i>E</i>) conformation of (+)-catechin</figcaption></figure> <p>Moreover, the flexibility of the C-ring allows for two <a href="/wiki/Conformational_isomerism" title="Conformational isomerism">conformation isomers</a>, putting the B-ring either in a pseudoequatorial position (E conformer) or in a pseudoaxial position (A conformer). Studies confirmed that (+)-catechin adopts a mixture of A- and E-conformers in aqueous solution and their conformational equilibrium has been evaluated to be 33:67.<sup id="cite_ref-Kriz_3-0" class="reference"><a href="#cite_note-Kriz-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p><p>As flavonoids, catechins can act as <a href="/wiki/Antioxidants" class="mw-redirect" title="Antioxidants">antioxidants</a> when in high concentration <i>in vitro</i>, but compared with other flavonoids, their antioxidant potential is low.<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> The ability to quench singlet oxygen seems to be in relation with the chemical structure of catechin, with the presence of the catechol moiety on ring B and the presence of a hydroxyl group activating the double bond on ring C.<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> <div class="mw-heading mw-heading3"><h3 id="Oxidation">Oxidation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Catechin&action=edit&section=2" title="Edit section: Oxidation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Electrochemical experiments show that (+)-catechin oxidation mechanism proceeds in sequential steps, related with the <a href="/wiki/Catechol" title="Catechol">catechol</a> and <a href="/wiki/Resorcinol" title="Resorcinol">resorcinol</a> groups and the oxidation is pH-dependent. The oxidation of the catechol 3′,4′-dihydroxyl electron-donating groups occurs first, at very low positive potentials, and is a reversible reaction. The hydroxyl groups of the resorcinol moiety oxidised afterwards were shown to undergo an irreversible oxidation reaction.<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>The <a href="/wiki/Laccase" title="Laccase">laccase</a>/<a href="/wiki/ABTS" title="ABTS">ABTS</a> system oxidizes (+)-catechin to oligomeric products<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> of which <a href="/wiki/Proanthocyanidin_A2" class="mw-redirect" title="Proanthocyanidin A2">proanthocyanidin A2</a> is a dimer. </p> <div class="mw-heading mw-heading3"><h3 id="Spectral_data">Spectral data</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Catechin&action=edit&section=3" title="Edit section: Spectral data"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Spectre_UV-vis_catechine.PNG" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/9d/Spectre_UV-vis_catechine.PNG/220px-Spectre_UV-vis_catechine.PNG" decoding="async" width="220" height="130" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/9d/Spectre_UV-vis_catechine.PNG/330px-Spectre_UV-vis_catechine.PNG 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/9d/Spectre_UV-vis_catechine.PNG/440px-Spectre_UV-vis_catechine.PNG 2x" data-file-width="1054" data-file-height="624" /></a><figcaption>UV spectrum of catechin.</figcaption></figure> <table border="1" cellspacing="0" cellpadding="3" style="margin: 0 0 0 0.5em; background: #FFFFFF; border-collapse: collapse; border-color: #C0C090;"> <tbody><tr> <th style="background: #F8EABA; text-align: center;" colspan="2"><a href="/wiki/UV/VIS_spectroscopy" class="mw-redirect" title="UV/VIS spectroscopy">UV-Vis</a> </th></tr> <tr> <td><a href="/wiki/Lambda-max" class="mw-redirect" title="Lambda-max">Lambda-max</a>: </td> <td>276 <a href="/wiki/Nanometre" title="Nanometre">nm</a> </td></tr> <tr> <td><a href="/wiki/Molar_absorptivity" class="mw-redirect" title="Molar absorptivity">Extinction coefficient</a> (log <i>ε</i>) </td> <td>4.01 </td></tr> <tr> <th style="background: #F8EABA; text-align: center;" colspan="2"><a href="/wiki/Infrared" title="Infrared">IR</a> </th></tr> <tr> <td>Major absorption bands </td> <td>1600 cm<sup>−1</sup>(benzene rings) </td></tr> <tr> <th style="background: #F8EABA; text-align: center;" colspan="2"><a href="/wiki/NMR_Spectroscopy" class="mw-redirect" title="NMR Spectroscopy">NMR</a> </th></tr> <tr> <td><a href="/wiki/Proton_NMR" class="mw-redirect" title="Proton NMR">Proton NMR</a> <p><br />(500 MHz, CD3OD): <br />Reference<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> <br />d : doublet, dd : doublet of doublets, <br />m : multiplet, s : singlet </p> </td> <td><a href="/wiki/Chemical_shift" title="Chemical shift">δ</a> :<br /> <p>2.49 (1H, dd, J = 16.0, 8.6 Hz, H-4a),<br /> 2.82 (1H, dd, J = 16.0, 1.6 Hz, H-4b), <br /> 3.97 (1H, m, H-3), <br /> 4.56 (1H, d, J = 7.8 Hz, H-2),<br /> 5.86 (1H, d, J = 2.1 Hz, H-6), <br /> 5.92 (1H, d, J = 2.1 Hz, H-8), <br /> 6.70 (1H, dd, J = 8.1, 1.8 Hz, H-6'), <br /> 6.75 (1H, d, J = 8.1 Hz, H-5'), <br /> 6.83 (1H, d, J = 1.8 Hz, H-2')<br /> </p> </td></tr> <tr> <td><a href="/wiki/Carbon-13_NMR" class="mw-redirect" title="Carbon-13 NMR">Carbon-13 NMR</a> </td></tr> <tr> <td>Other NMR data </td></tr> <tr> <th style="background: #F8EABA; text-align: center;" colspan="2"><a href="/wiki/Mass_Spectrometry" class="mw-redirect" title="Mass Spectrometry">MS</a> </th></tr> <tr> <td>Masses of <br />main fragments </td> <td>ESI-MS [M+H]<sup>+</sup> <i>m</i>/<i>z</i> : 291.0 <p><br />273 water loss <br />139 retro Diels–Alder <br />123 <br />165 <br />147 </p> </td></tr> </tbody></table> <div class="mw-heading mw-heading2"><h2 id="Natural_occurrences">Natural occurrences</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Catechin&action=edit&section=4" title="Edit section: Natural occurrences"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>(+)-Catechin and (−)-epicatechin as well as their <a href="/wiki/Gallic_acid" title="Gallic acid">gallic acid</a> conjugates are ubiquitous constituents of <a href="/wiki/Vascular_plant" title="Vascular plant">vascular plants</a>, and frequent components of <a href="/wiki/Traditional_medicine" title="Traditional medicine">traditional herbal remedies</a>, such as <i><a href="/wiki/Uncaria_rhynchophylla" title="Uncaria rhynchophylla">Uncaria rhynchophylla</a></i>. The two <a href="/wiki/Isomers" class="mw-redirect" title="Isomers">isomers</a> are mostly found as <a href="/wiki/Theobroma_cacao" title="Theobroma cacao">cacao</a> and <a href="/wiki/Tea" title="Tea">tea</a> constituents, as well as in <i><a href="/wiki/Vitis_vinifera" title="Vitis vinifera">Vitis vinifera</a></i> grapes.<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><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> </p> <div class="mw-heading mw-heading3"><h3 id="In_food">In food</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Catechin&action=edit&section=5" title="Edit section: In food"><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">Main articles: <a href="/wiki/Phenolic_content_in_tea" title="Phenolic content in tea">Phenolic content in tea</a> and <a href="/wiki/Phenolic_content_in_wine" title="Phenolic content in wine">Phenolic content in wine</a></div> <p>The main dietary sources of catechins in Europe and the United States are <a href="/wiki/Tea" title="Tea">tea</a> and <a href="/wiki/Pome" title="Pome">pome</a> fruits.<sup id="cite_ref-Chun_2007_12-0" class="reference"><a href="#cite_note-Chun_2007-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Vogiatzoglou_2015_13-0" class="reference"><a href="#cite_note-Vogiatzoglou_2015-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> </p><p>Catechins and epicatechins are found in <a href="/wiki/Cocoa_bean" title="Cocoa bean">cocoa</a>,<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> which, according to one database, has the highest content (108 mg/100 g) of catechins among foods analyzed, followed by <a href="/wiki/Prune_juice" title="Prune juice">prune juice</a> (25 mg/100 ml) and <a href="/wiki/Broad_bean" class="mw-redirect" title="Broad bean">broad bean</a> pod (16 mg/100 g).<sup id="cite_ref-pe_15-0" class="reference"><a href="#cite_note-pe-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> <a href="/wiki/A%C3%A7a%C3%AD_oil" title="Açaí oil">Açaí oil</a>, obtained from the fruit of the açaí palm (<i>Euterpe oleracea</i>), contains (+)-catechins (67 mg/kg).<sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p><p>Catechins are diverse among foods,<sup id="cite_ref-pe_15-1" class="reference"><a href="#cite_note-pe-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> from <a href="/wiki/Peach" title="Peach">peaches</a><sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> to <a href="/wiki/Green_tea" title="Green tea">green tea</a> and <a href="/wiki/Vinegar" title="Vinegar">vinegar</a>.<sup id="cite_ref-pe_15-2" class="reference"><a href="#cite_note-pe-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup><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> Catechins are found in <a href="/wiki/Barley" title="Barley">barley</a> grain, where they are the main phenolic compound responsible for <a href="/wiki/Dough" title="Dough">dough</a> discoloration.<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> The taste associated with monomeric (+)-catechin or (−)-epicatechin is described as slightly <a href="/wiki/Astringent" title="Astringent">astringent</a>, but not bitter.<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="Metabolism">Metabolism</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Catechin&action=edit&section=6" title="Edit section: Metabolism"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Biosynthesis">Biosynthesis</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Catechin&action=edit&section=7" title="Edit section: Biosynthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><span class="mw-default-size" typeof="mw:File"><a href="/wiki/File:Biosynthesis_of_4-hydroxycinnamoyl-CoA.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/8/8c/Biosynthesis_of_4-hydroxycinnamoyl-CoA.png" decoding="async" width="659" height="296" class="mw-file-element" data-file-width="659" data-file-height="296" /></a></span> </p><p>The biosynthesis of catechin begins with ma <a href="/wiki/Coumaroyl-CoA" title="Coumaroyl-CoA">4-hydroxycinnamoyl CoA</a> starter unit which undergoes chain extension by the addition of three <a href="/wiki/Malonyl-CoA" title="Malonyl-CoA">malonyl-CoAs</a> through a PKSIII pathway. 4-Hydroxycinnamoyl CoA is biosynthesized from <a href="/wiki/Phenylalanine" title="Phenylalanine"><small>L</small>-phenylalanine</a> through the Shikimate pathway. <small>L</small>-Phenylalanine is first deaminated by <a href="/wiki/Phenylalanine_ammonia-lyase" title="Phenylalanine ammonia-lyase">phenylalanine ammonia lyase (PAL)</a> forming cinnamic acid which is then oxidized to <a href="/wiki/4-Coumaric_acid" class="mw-redirect" title="4-Coumaric acid">4-hydroxycinnamic acid</a> by cinnamate 4-hydroxylase. Chalcone synthase then catalyzes the condensation of 4-hydroxycinnamoyl CoA and three molecules of malonyl-CoA to form <a href="/wiki/Chalconoid" title="Chalconoid">chalcone</a>. Chalcone is then isomerized to <a href="/wiki/Naringenin" title="Naringenin">naringenin</a> by chalcone isomerase which is oxidized to <a href="/wiki/Eriodictyol" title="Eriodictyol">eriodictyol</a> by flavonoid 3′-hydroxylase and further oxidized to <a href="/wiki/Taxifolin" title="Taxifolin">taxifolin</a> by flavanone 3-hydroxylase. Taxifolin is then reduced by dihydroflavanol 4-reductase and <a href="/wiki/Leucoanthocyanidin_reductase" title="Leucoanthocyanidin reductase">leucoanthocyanidin reductase</a> to yield catechin. The biosynthesis of catechin is shown below<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><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><sup id="cite_ref-23" class="reference"><a href="#cite_note-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> </p><p><a href="/wiki/Leucocyanidin_reductase" class="mw-redirect" title="Leucocyanidin reductase">Leucocyanidin reductase</a> (LCR) uses 2,3-<i>trans</i>-3,4-<i>cis</i>-<a href="/wiki/Leucocyanidin" title="Leucocyanidin">leucocyanidin</a> to produce (+)-catechin and is the first enzyme in the <a href="/wiki/Proanthocyanidin" title="Proanthocyanidin">proanthocyanidin</a> (PA) specific pathway. Its activity has been measured in leaves, flowers, and seeds of the legumes <i><a href="/wiki/Medicago_sativa" class="mw-redirect" title="Medicago sativa">Medicago sativa</a></i>, <i><a href="/wiki/Lotus_japonicus" title="Lotus japonicus">Lotus japonicus</a></i>, <i><a href="/wiki/Lotus_uliginosus" class="mw-redirect" title="Lotus uliginosus">Lotus uliginosus</a></i>, <i><a href="/wiki/Hedysarum_sulfurescens" class="mw-redirect" title="Hedysarum sulfurescens">Hedysarum sulfurescens</a></i>, and <i><a href="/wiki/Robinia_pseudoacacia" title="Robinia pseudoacacia">Robinia pseudoacacia</a></i>.<sup id="cite_ref-24" class="reference"><a href="#cite_note-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> The enzyme is also present in <i><a href="/wiki/Vitis_vinifera" title="Vitis vinifera">Vitis vinifera</a></i> (grape).<sup id="cite_ref-25" class="reference"><a href="#cite_note-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> </p><p><span class="mw-default-size" typeof="mw:File"><a href="/wiki/File:Biosynthesis_of_catechin.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/4/40/Biosynthesis_of_catechin.png" decoding="async" width="720" height="925" class="mw-file-element" data-file-width="720" data-file-height="925" /></a></span> </p> <div class="mw-heading mw-heading3"><h3 id="Biodegradation">Biodegradation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Catechin&action=edit&section=8" title="Edit section: Biodegradation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Catechin oxygenase, a key enzyme in the degradation of catechin, is present in fungi and bacteria.<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> </p><p>Among bacteria, degradation of (+)-catechin can be achieved by <i><a href="/wiki/Acinetobacter_calcoaceticus" title="Acinetobacter calcoaceticus">Acinetobacter calcoaceticus</a></i>. Catechin is metabolized to <a href="/wiki/Protocatechuic_acid" title="Protocatechuic acid">protocatechuic acid</a> (PCA) and <a href="/wiki/Phloroglucinol_carboxylic_acid" title="Phloroglucinol carboxylic acid">phloroglucinol carboxylic acid</a> (PGCA).<sup id="cite_ref-27" class="reference"><a href="#cite_note-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> It is also degraded by <i><a href="/wiki/Bradyrhizobium_japonicum" title="Bradyrhizobium japonicum">Bradyrhizobium japonicum</a></i>. Phloroglucinol carboxylic acid is further <a href="/wiki/Decarboxylated" class="mw-redirect" title="Decarboxylated">decarboxylated</a> to <a href="/wiki/Phloroglucinol" title="Phloroglucinol">phloroglucinol</a>, which is <a href="/wiki/Dehydroxylation" class="mw-redirect" title="Dehydroxylation">dehydroxylated</a> to <a href="/wiki/Resorcinol" title="Resorcinol">resorcinol</a>. Resorcinol is hydroxylated to <a href="/wiki/Hydroxyquinol" title="Hydroxyquinol">hydroxyquinol</a>. Protocatechuic acid and hydroxyquinol undergo <a href="/wiki/Diol" title="Diol">intradiol</a> cleavage through <a href="/wiki/Protocatechuate_3,4-dioxygenase" title="Protocatechuate 3,4-dioxygenase">protocatechuate 3,4-dioxygenase</a> and <a href="/wiki/Hydroxyquinol_1,2-dioxygenase" title="Hydroxyquinol 1,2-dioxygenase">hydroxyquinol 1,2-dioxygenase</a> to form <a href="/wiki/3-Carboxy-cis,cis-muconic_acid" title="3-Carboxy-cis,cis-muconic acid">β-carboxy-<i>cis</i>,<i>cis</i>-muconic acid </a> and <a href="/wiki/Maleyl_acetate" class="mw-redirect" title="Maleyl acetate">maleyl acetate</a>.<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> </p><p>Among fungi, degradation of catechin can be achieved by <i><a href="/wiki/Chaetomium_cupreum" title="Chaetomium cupreum">Chaetomium cupreum</a></i>.<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> </p> <div class="mw-heading mw-heading3"><h3 id="Metabolism_in_humans">Metabolism in humans</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Catechin&action=edit&section=9" title="Edit section: Metabolism in humans"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:Epicatechin_metabolites.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d9/Epicatechin_metabolites.png/220px-Epicatechin_metabolites.png" decoding="async" width="220" height="143" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d9/Epicatechin_metabolites.png/330px-Epicatechin_metabolites.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d9/Epicatechin_metabolites.png/440px-Epicatechin_metabolites.png 2x" data-file-width="2038" data-file-height="1325" /></a><figcaption>Human metabolites of epicatechin (excluding colonic metabolites)<sup id="cite_ref-Ottaviani_2016_30-0" class="reference"><a href="#cite_note-Ottaviani_2016-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup></figcaption></figure> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Schematic_representation_of_(%E2%88%92)-epicatechin_metabolism_in_humans_as_a_function_of_time_post-oral_intake.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/Schematic_representation_of_%28%E2%88%92%29-epicatechin_metabolism_in_humans_as_a_function_of_time_post-oral_intake.jpg/220px-Schematic_representation_of_%28%E2%88%92%29-epicatechin_metabolism_in_humans_as_a_function_of_time_post-oral_intake.jpg" decoding="async" width="220" height="235" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/Schematic_representation_of_%28%E2%88%92%29-epicatechin_metabolism_in_humans_as_a_function_of_time_post-oral_intake.jpg/330px-Schematic_representation_of_%28%E2%88%92%29-epicatechin_metabolism_in_humans_as_a_function_of_time_post-oral_intake.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/21/Schematic_representation_of_%28%E2%88%92%29-epicatechin_metabolism_in_humans_as_a_function_of_time_post-oral_intake.jpg/440px-Schematic_representation_of_%28%E2%88%92%29-epicatechin_metabolism_in_humans_as_a_function_of_time_post-oral_intake.jpg 2x" data-file-width="926" data-file-height="989" /></a><figcaption>Schematic representation of (−)-epicatechin metabolism in humans as a function of time post-oral intake. SREM: structurally related (−)-epicatechin metabolites. 5C-RFM: 5-carbon ring fission metabolites. 3/1C-RFM: 3- and 1-carbon-side chain ring fission metabolites. The structures of the most abundant (−)-epicatechin metabolites present in the systemic circulation and in urine are depicted.<sup id="cite_ref-Ottaviani_2016_30-1" class="reference"><a href="#cite_note-Ottaviani_2016-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup></figcaption></figure> <p>Catechins are metabolised upon uptake from the <a href="/wiki/Gastrointestinal_tract" title="Gastrointestinal tract">gastrointestinal tract</a>, in particular the <a href="/wiki/Jejunum" title="Jejunum">jejunum</a>,<sup id="cite_ref-31" class="reference"><a href="#cite_note-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> and in the <a href="/wiki/Liver" title="Liver">liver</a>, resulting in so-called structurally related epicatechin metabolites (SREM).<sup id="cite_ref-Ottaviani_SREM_32-0" class="reference"><a href="#cite_note-Ottaviani_SREM-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> The main metabolic pathways for SREMs are <a href="/wiki/Glucuronidation" title="Glucuronidation">glucuronidation</a>, <a href="/wiki/Sulfation" title="Sulfation">sulfation</a> and <a href="/wiki/Methylation" title="Methylation">methylation</a> of the <a href="/wiki/Catechol" title="Catechol">catechol</a> group by <a href="/wiki/Catechol-O-methyl_transferase" class="mw-redirect" title="Catechol-O-methyl transferase">catechol-O-methyl transferase</a>, with only small amounts detected in plasma.<sup id="cite_ref-lpi_33-0" class="reference"><a href="#cite_note-lpi-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Ottaviani_2016_30-2" class="reference"><a href="#cite_note-Ottaviani_2016-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> The majority of dietary catechins are however metabolised by the <a href="/wiki/Gut_flora" class="mw-redirect" title="Gut flora">colonic microbiome</a> to <a href="/wiki/Gamma-Valerolactone" class="mw-redirect" title="Gamma-Valerolactone">gamma-valerolactones</a> and <a href="/wiki/Hippuric_acid" title="Hippuric acid">hippuric acids</a> which undergo further <a href="/wiki/Biotransformation" title="Biotransformation">biotransformation</a>, <a href="/wiki/Glucuronidation" title="Glucuronidation">glucuronidation</a>, <a href="/wiki/Sulfation" title="Sulfation">sulfation</a> and <a href="/wiki/Methylation" title="Methylation">methylation</a> in the <a href="/wiki/Liver" title="Liver">liver</a>.<sup id="cite_ref-lpi_33-1" class="reference"><a href="#cite_note-lpi-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> </p><p>The stereochemical configuration of catechins has a strong impact on their uptake and metabolism as uptake is highest for (−)-epicatechin and lowest for (−)-catechin.<sup id="cite_ref-Ottaviani_stereo_34-0" class="reference"><a href="#cite_note-Ottaviani_stereo-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Biotransformation">Biotransformation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Catechin&action=edit&section=10" title="Edit section: Biotransformation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Biotransformation of (+)-catechin into <a href="/wiki/Taxifolin" title="Taxifolin">taxifolin</a> by a two-step oxidation can be achieved by <i><a href="/wiki/Burkholderia" title="Burkholderia">Burkholderia</a></i> sp.<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>(+)-Catechin and (−)-epicatechin are transformed by the endophytic filamentous fungus <i><a href="/wiki/Diaporthe" title="Diaporthe">Diaporthe</a></i> sp. into the 3,4-cis-dihydroxyflavan derivatives, <a href="/wiki/(2R,3S,4S)-3,4,5,7,3%27,4%27-hexahydroxyflavan" class="mw-redirect" title="(2R,3S,4S)-3,4,5,7,3',4'-hexahydroxyflavan">(+)-(2<i>R</i>,3<i>S</i>,4<i>S</i>)-3,4,5,7,3′,4′-hexahydroxyflavan</a> (leucocyanidin) and <a href="/w/index.php?title=(2R,3R,4R)-3,4,5,7,3%27,4%27-hexahydroxyflavan&action=edit&redlink=1" class="new" title="(2R,3R,4R)-3,4,5,7,3',4'-hexahydroxyflavan (page does not exist)">(−)-(2<i>R</i>,3<i>R</i>,4<i>R</i>)-3,4,5,7,3′,4′-hexahydroxyflavan</a>, respectively, whereas (−)-catechin and (+)-epicatechin with a (2<i>S</i>)-phenyl group resisted the biooxidation.<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 href="/wiki/Leucoanthocyanidin_reductase" title="Leucoanthocyanidin reductase">Leucoanthocyanidin reductase</a> (LAR) uses (2<i>R</i>,3<i>S</i>)-catechin, NADP<sup>+</sup> and H<sub>2</sub>O to produce 2,3-<i>trans</i>-3,4-<i>cis</i>-<a href="/wiki/Leucocyanidin" title="Leucocyanidin">leucocyanidin</a>, NADPH, and H<sup>+</sup>. Its gene expression has been studied in developing grape berries and grapevine leaves.<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-heading3"><h3 id="Glycosides">Glycosides</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Catechin&action=edit&section=11" title="Edit section: Glycosides"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Catechin-7-O-glucoside" title="Catechin-7-O-glucoside">(2<i>R</i>,3<i>S</i>)-Catechin-7-<i>O</i>-β-<small>D</small>-glucopyranoside</a> can be isolated from <a href="/wiki/Barley" title="Barley">barley</a> (<i>Hordeum vulgare</i> L.) and malt.<sup id="cite_ref-38" class="reference"><a href="#cite_note-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup></li> <li><a href="/w/index.php?title=Epigeoside&action=edit&redlink=1" class="new" title="Epigeoside (page does not exist)">Epigeoside</a> (catechin-3-<i>O</i>-α-<small>L</small>-rhamnopyranosyl-(1–4)-β-<small>D</small>-glucopyranosyl-(1–6)-β-<small>D</small>-glucopyranoside) can be isolated from the rhizomes of <i><a href="/wiki/Epigynum_auritum" title="Epigynum auritum">Epigynum auritum</a></i>.<sup id="cite_ref-39" class="reference"><a href="#cite_note-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup></li></ul> <div class="mw-heading mw-heading2"><h2 id="Research">Research</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Catechin&action=edit&section=12" title="Edit section: Research"><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:Inter-species_differences_in_(-)-epicatechin_metabolism.pdf" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e1/Inter-species_differences_in_%28-%29-epicatechin_metabolism.pdf/page1-220px-Inter-species_differences_in_%28-%29-epicatechin_metabolism.pdf.jpg" decoding="async" width="220" height="59" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e1/Inter-species_differences_in_%28-%29-epicatechin_metabolism.pdf/page1-330px-Inter-species_differences_in_%28-%29-epicatechin_metabolism.pdf.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e1/Inter-species_differences_in_%28-%29-epicatechin_metabolism.pdf/page1-440px-Inter-species_differences_in_%28-%29-epicatechin_metabolism.pdf.jpg 2x" data-file-width="1447" data-file-height="389" /></a><figcaption>Interspecies differences in (−)-epicatechin metabolism.<sup id="cite_ref-Ottaviani_2016_30-3" class="reference"><a href="#cite_note-Ottaviani_2016-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup></figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="Vascular_function">Vascular function</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Catechin&action=edit&section=13" title="Edit section: Vascular function"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Only limited evidence from dietary studies indicates that catechins may affect <a href="/wiki/Endothelium" title="Endothelium">endothelium</a>-dependent <a href="/wiki/Vasodilation" title="Vasodilation">vasodilation</a> which could contribute to normal <a href="/wiki/Blood_flow" class="mw-redirect" title="Blood flow">blood flow</a> regulation in humans.<sup id="cite_ref-40" class="reference"><a href="#cite_note-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-41" class="reference"><a href="#cite_note-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> Green tea catechins may improve blood pressure, especially when systolic blood pressure is above 130 mmHg.<sup id="cite_ref-ejn_42-0" class="reference"><a href="#cite_note-ejn-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-43" class="reference"><a href="#cite_note-43"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup> </p><p>Due to extensive metabolism during digestion, the fate and activity of catechin metabolites responsible for this effect on blood vessels, as well as the actual mode of action, are unknown.<sup id="cite_ref-lpi_33-2" class="reference"><a href="#cite_note-lpi-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pnas_44-0" class="reference"><a href="#cite_note-pnas-44"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Adverse_events">Adverse events</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Catechin&action=edit&section=14" title="Edit section: Adverse events"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Catechin and its metabolites can bind tightly to red blood cells and thereby induce the development of <a href="/wiki/Autoantibody" title="Autoantibody">autoantibodies</a>, resulting in <a href="/wiki/Haemolytic_anaemia" class="mw-redirect" title="Haemolytic anaemia">haemolytic anaemia</a> and <a href="/wiki/Renal_failure" class="mw-redirect" title="Renal failure">renal failure</a>.<sup id="cite_ref-45" class="reference"><a href="#cite_note-45"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup> This resulted in the withdrawal of the catechin-containing drug Catergen, used to treat <a href="/wiki/Viral_hepatitis" title="Viral hepatitis">viral hepatitis</a>,<sup id="cite_ref-46" class="reference"><a href="#cite_note-46"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup> from market in 1985.<sup id="cite_ref-47" class="reference"><a href="#cite_note-47"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup> </p><p>Catechins from <a href="/wiki/Green_tea" title="Green tea">green tea</a> can be <a href="/wiki/Hepatotoxicity" title="Hepatotoxicity">hepatotoxic</a><sup id="cite_ref-48" class="reference"><a href="#cite_note-48"><span class="cite-bracket">[</span>48<span class="cite-bracket">]</span></a></sup> and the <a href="/wiki/European_Food_Safety_Authority" title="European Food Safety Authority">European Food Safety Authority</a> has recommended not to exceed 800 mg per day.<sup id="cite_ref-49" class="reference"><a href="#cite_note-49"><span class="cite-bracket">[</span>49<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Other">Other</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Catechin&action=edit&section=15" title="Edit section: Other"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>One limited meta-analysis showed that increasing consumption of green tea and its catechins to seven cups per day provided a small reduction in <a href="/wiki/Prostate_cancer" title="Prostate cancer">prostate cancer</a>.<sup id="cite_ref-50" class="reference"><a href="#cite_note-50"><span class="cite-bracket">[</span>50<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Nanoparticle" title="Nanoparticle">Nanoparticle</a> methods are under preliminary research as potential delivery systems of catechins.<sup id="cite_ref-51" class="reference"><a href="#cite_note-51"><span class="cite-bracket">[</span>51<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Botanical_effects">Botanical effects</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Catechin&action=edit&section=16" title="Edit section: Botanical effects"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Catechins released into the ground by some plants may hinder the growth of their neighbors, a form of <a href="/wiki/Allelopathy" title="Allelopathy">allelopathy</a>.<sup id="cite_ref-broz_52-0" class="reference"><a href="#cite_note-broz-52"><span class="cite-bracket">[</span>52<span class="cite-bracket">]</span></a></sup> <i><a href="/wiki/Centaurea_maculosa" class="mw-redirect" title="Centaurea maculosa">Centaurea maculosa</a></i>, the spotted knapweed often studied for this behavior, releases catechin <a href="/wiki/Isomers" class="mw-redirect" title="Isomers">isomers</a> into the ground through its roots, potentially having effects as an <a href="/wiki/Antibiotic" title="Antibiotic">antibiotic</a> or <a href="/wiki/Herbicide" title="Herbicide">herbicide</a>. One hypothesis is that it causes a <a href="/wiki/Reactive_oxygen_species" title="Reactive oxygen species">reactive oxygen species</a> wave through the target plant's root to kill root cells by <a href="/wiki/Apoptosis" title="Apoptosis">apoptosis</a>.<sup id="cite_ref-pmid12958360_53-0" class="reference"><a href="#cite_note-pmid12958360-53"><span class="cite-bracket">[</span>53<span class="cite-bracket">]</span></a></sup> Most plants in the European ecosystem have defenses against catechin, but few plants are protected against it in the North American ecosystem where <i><a href="/wiki/Centaurea_maculosa" class="mw-redirect" title="Centaurea maculosa">Centaurea maculosa</a></i> is an invasive, uncontrolled weed.<sup id="cite_ref-broz_52-1" class="reference"><a href="#cite_note-broz-52"><span class="cite-bracket">[</span>52<span class="cite-bracket">]</span></a></sup> </p><p>Catechin acts as an infection-inhibiting factor in strawberry leaves.<sup id="cite_ref-54" class="reference"><a href="#cite_note-54"><span class="cite-bracket">[</span>54<span class="cite-bracket">]</span></a></sup> Epicatechin and catechin may prevent coffee berry disease by inhibiting <a href="/wiki/Appressorium" title="Appressorium">appressorial</a> melanization of <i><a href="/wiki/Colletotrichum_kahawae" title="Colletotrichum kahawae">Colletotrichum kahawae</a></i>.<sup id="cite_ref-55" class="reference"><a href="#cite_note-55"><span class="cite-bracket">[</span>55<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Catechin&action=edit&section=17" 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 reflist-columns-2"> <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://web.archive.org/web/20190210133448/http://www.fao.org/docrep/V8879e/V8879e05.htm">"Cutch and catechu plant origin"</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=Biotechnology+Letters&rft.atitle=Epicatechin+and+catechin+may+prevent+coffee+berry+disease+by+inhibition+of+appressorial+melanization+of+Colletotrichum+kahawae&rft.volume=28&rft.issue=20&rft.pages=1637-1640&rft.date=2006-10&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A30593181%23id-name%3DS2CID&rft_id=info%3Apmid%2F16955359&rft_id=info%3Adoi%2F10.1007%2Fs10529-006-9135-2&rft.aulast=Chen&rft.aufirst=Z&rft.au=Liang%2C+J&rft.au=Zhang%2C+C&rft.au=Rodrigues%2C+CJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACatechin" 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=Catechin&action=edit&section=18" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1235681985">.mw-parser-output .side-box{margin:4px 0;box-sizing:border-box;border:1px solid #aaa;font-size:88%;line-height:1.25em;background-color:var(--background-color-interactive-subtle,#f8f9fa);display:flow-root}.mw-parser-output .side-box-abovebelow,.mw-parser-output .side-box-text{padding:0.25em 0.9em}.mw-parser-output .side-box-image{padding:2px 0 2px 0.9em;text-align:center}.mw-parser-output .side-box-imageright{padding:2px 0.9em 2px 0;text-align:center}@media(min-width:500px){.mw-parser-output .side-box-flex{display:flex;align-items:center}.mw-parser-output .side-box-text{flex:1;min-width:0}}@media(min-width:720px){.mw-parser-output .side-box{width:238px}.mw-parser-output .side-box-right{clear:right;float:right;margin-left:1em}.mw-parser-output .side-box-left{margin-right:1em}}</style><style data-mw-deduplicate="TemplateStyles:r1237033735">@media print{body.ns-0 .mw-parser-output .sistersitebox{display:none!important}}@media screen{html.skin-theme-clientpref-night .mw-parser-output .sistersitebox img[src*="Wiktionary-logo-en-v2.svg"]{background-color:white}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .sistersitebox img[src*="Wiktionary-logo-en-v2.svg"]{background-color:white}}</style><div class="side-box side-box-right plainlinks sistersitebox"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"> <div class="side-box-flex"> <div class="side-box-image"><span class="noviewer" typeof="mw:File"><span><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/9/99/Wiktionary-logo-en-v2.svg/40px-Wiktionary-logo-en-v2.svg.png" decoding="async" width="40" height="40" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/99/Wiktionary-logo-en-v2.svg/60px-Wiktionary-logo-en-v2.svg.png 1.5x, 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aria-labelledby="Flavan-3-ols_and_their_glycosides" 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:Flavanol" title="Template:Flavanol"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Flavanol" title="Template talk:Flavanol"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Flavanol" title="Special:EditPage/Template:Flavanol"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Flavan-3-ols_and_their_glycosides" style="font-size:114%;margin:0 4em">Flavan-3-ols and their <a href="/wiki/Glycoside" title="Glycoside">glycosides</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Flavan-3-ol" title="Flavan-3-ol">Flavan-3-ols</a></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/Afzelechin" title="Afzelechin">Afzelechin</a></li> <li><a class="mw-selflink selflink">Catechin</a> (Epicatechin)</li> <li><a href="/wiki/Epicatechin_gallate" title="Epicatechin gallate">Epicatechin gallate</a></li> <li><a href="/wiki/Gallocatechol" title="Gallocatechol">Epigallocatechin</a></li> <li><a href="/wiki/Fisetinidol" title="Fisetinidol">Fisetinidol</a></li> <li><a href="/wiki/Gallocatechol" title="Gallocatechol">Gallocatechin</a></li> <li><a href="/wiki/Guibourtinidol" title="Guibourtinidol">Guibourtinidol</a></li> <li><a href="/wiki/Mesquitol" title="Mesquitol">Mesquitol</a></li> <li><a href="/wiki/Oritin" title="Oritin">Oritin</a></li> <li><a href="/wiki/Robinetinidol" title="Robinetinidol">Robinetinidol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">O-methylated flavan-3ols</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="/wiki/Meciadanol" title="Meciadanol">Meciadanol</a> (3-O-methylcatechin)</li> <li><a href="/w/index.php?title=Ourateacatechin&action=edit&redlink=1" class="new" title="Ourateacatechin (page does not exist)">Ourateacatechin</a> (<a href="/w/index.php?title=4%E2%80%B2-O-methyl-(%E2%88%92)-epigallocatechin&action=edit&redlink=1" class="new" title="4′-O-methyl-(−)-epigallocatechin (page does not exist)">4′-O-methyl-(−)-epigallocatechin</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Glycosides</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=Arthromerin_A&action=edit&redlink=1" class="new" title="Arthromerin A (page does not exist)">Arthromerin A</a> (Afzelechin-3-O-β-D-xylopyranoside)</li> <li><a href="/w/index.php?title=Arthromerin_B&action=edit&redlink=1" class="new" title="Arthromerin B (page does not exist)">Arthromerin B</a> (Afzelechin-3-O-β-D-glucopyranoside)</li> <li><a href="/w/index.php?title=Catechin-3-O-glucoside&action=edit&redlink=1" class="new" title="Catechin-3-O-glucoside (page does not exist)">Catechin-3-O-glucoside</a></li> <li><a href="/w/index.php?title=Catechin-3%27-O-glucoside&action=edit&redlink=1" class="new" title="Catechin-3'-O-glucoside (page does not exist)">Catechin-3'-O-glucoside</a></li> <li><a href="/w/index.php?title=Catechin-4%27-O-glucoside&action=edit&redlink=1" class="new" title="Catechin-4'-O-glucoside (page does not exist)">Catechin-4'-O-glucoside</a></li> <li><a href="/wiki/Catechin-5-O-glucoside" title="Catechin-5-O-glucoside">Catechin-5-O-glucoside</a></li> <li><a href="/wiki/Catechin-7-O-glucoside" title="Catechin-7-O-glucoside">Catechin-7-O-glucoside</a></li> <li><a href="/w/index.php?title=(%2B)-Catechin_7-O-%CE%B2-D-xylopyranoside&action=edit&redlink=1" class="new" title="(+)-Catechin 7-O-β-D-xylopyranoside (page does not exist)">(+)-Catechin 7-O-β-D-xylopyranoside</a></li> <li><a href="/w/index.php?title=Epicatechin-3%E2%80%B2-O-glucoside&action=edit&redlink=1" class="new" title="Epicatechin-3′-O-glucoside (page does not exist)">Epicatechin-3′-O-glucoside</a></li> <li><a href="/w/index.php?title=Glochiflavanoside_A&action=edit&redlink=1" class="new" title="Glochiflavanoside A (page does not exist)">Glochiflavanoside A</a>, <a href="/w/index.php?title=Glochiflavanoside_B&action=edit&redlink=1" class="new" title="Glochiflavanoside B (page does not exist)">B</a>, <a href="/w/index.php?title=Glochiflavanoside_C&action=edit&redlink=1" class="new" title="Glochiflavanoside C (page does not exist)">C</a> <a href="/w/index.php?title=Glochiflavanoside_D&action=edit&redlink=1" class="new" title="Glochiflavanoside D (page does not exist)">D</a></li> <li><a href="/w/index.php?title=Polydine&action=edit&redlink=1" class="new" title="Polydine (page does not exist)">Polydine</a> (<a href="/w/index.php?title=(%2B)-catechin_7-O-%CE%B1-L-arabinoside&action=edit&redlink=1" class="new" title="(+)-catechin 7-O-α-L-arabinoside (page does not exist)">(+)-catechin 7-O-α-L-arabinoside</a>)</li> <li><a href="/w/index.php?title=Symplocoside&action=edit&redlink=1" class="new" title="Symplocoside (page does not exist)">Symplocoside</a> (<a href="/w/index.php?title=3%E2%80%99-O-methyl-(-)-epicatechin_7-O-%CE%B2-D-glucopyranoside&action=edit&redlink=1" class="new" title="3’-O-methyl-(-)-epicatechin 7-O-β-D-glucopyranoside (page does not exist)">3’-O-methyl-(-)-epicatechin 7-O-β-D-glucopyranoside</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Acetylated</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"><a href="/wiki/Phylloflavan" title="Phylloflavan">Phylloflavan</a></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Gallate esters</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/Epigallocatechin_gallate" title="Epigallocatechin gallate">Epigallocatechin gallate</a></li> <li><a href="/wiki/Gallocatechin_gallate" title="Gallocatechin gallate">Gallocatechin gallate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Misc.</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="/wiki/Thearubigin" title="Thearubigin">Thearubigins</a></li></ul> </div></td></tr></tbody></table></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?type=1x1" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Retrieved from "<a dir="ltr" href="https://en.wikipedia.org/w/index.php?title=Catechin&oldid=1256680561">https://en.wikipedia.org/w/index.php?title=Catechin&oldid=1256680561</a>"</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div id="mw-normal-catlinks" class="mw-normal-catlinks"><a href="/wiki/Help:Category" title="Help:Category">Categories</a>: <ul><li><a href="/wiki/Category:Flavanols" title="Category:Flavanols">Flavanols</a></li><li><a href="/wiki/Category:Catechols" title="Category:Catechols">Catechols</a></li><li><a href="/wiki/Category:Nutrition" 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