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Available in 13 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-13" 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">13 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%81%D9%84%D8%A7%D9%81%D8%A7%D9%86%D9%88%D9%84%D8%A7%D8%AA" title="فلافانولات – Arabic" lang="ar" hreflang="ar" data-title="فلافانولات" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Flavanol" title="Flavanol – Catalan" lang="ca" hreflang="ca" data-title="Flavanol" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%A6%CE%BB%CE%B1%CE%B2%CE%B1%CE%BD-3-%CF%8C%CE%BB%CE%B5%CF%82" title="Φλαβαν-3-όλες – Greek" lang="el" hreflang="el" data-title="Φλαβαν-3-όλες" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target"><span>Ελληνικά</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Flavanol" title="Flavanol – Spanish" lang="es" hreflang="es" data-title="Flavanol" 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/Flavan-3-olo" title="Flavan-3-olo – Esperanto" lang="eo" hreflang="eo" data-title="Flavan-3-olo" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D9%81%D9%84%D8%A7%D9%88%D8%A7%D9%86-%DB%B3-%D8%A7%D9%84" title="فلاوان-۳-ال – Persian" lang="fa" hreflang="fa" data-title="فلاوان-۳-ال" 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/Flavan-3-ol" title="Flavan-3-ol – French" lang="fr" hreflang="fr" data-title="Flavan-3-ol" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%95%E3%83%A9%E3%83%90%E3%83%B3-3-%E3%82%AA%E3%83%BC%E3%83%AB" title="フラバン-3-オール – Japanese" lang="ja" hreflang="ja" data-title="フラバン-3-オール" 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/Flavan-3-ol" title="Flavan-3-ol – Portuguese" lang="pt" hreflang="pt" data-title="Flavan-3-ol" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Flavan-3-ol" title="Flavan-3-ol – Romanian" lang="ro" hreflang="ro" data-title="Flavan-3-ol" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Flavan-3-ol" title="Flavan-3-ol – Serbian" lang="sr" hreflang="sr" data-title="Flavan-3-ol" 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-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Flavanolit" title="Flavanolit – Finnish" lang="fi" hreflang="fi" data-title="Flavanolit" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E9%BB%84%E7%83%B7-3-%E9%86%87" title="黄烷-3-醇 – Chinese" lang="zh" hreflang="zh" data-title="黄烷-3-醇" 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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id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Category of polyphenol compound</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">Not to be confused with <a href="/wiki/Flavonol" class="mw-redirect" title="Flavonol">Flavonol</a>.</div> <p class="mw-empty-elt"> </p> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Flavan-3-ol.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6e/Flavan-3-ol.svg/250px-Flavan-3-ol.svg.png" decoding="async" width="250" height="155" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6e/Flavan-3-ol.svg/500px-Flavan-3-ol.svg.png 1.5x" data-file-width="512" data-file-height="318" /></a><figcaption>Chemical structure of flavan-3-ol</figcaption></figure> <p><b>Flavan-3-ols</b> (sometimes referred to as <b>flavanols</b>) are a subgroup of <a href="/wiki/Flavonoid" title="Flavonoid">flavonoids</a>. They are derivatives of <a href="/wiki/Flavan" title="Flavan">flavans</a> that possess a 2-phenyl-3,4-dihydro-2<i>H</i>-chromen-3-ol skeleton. Flavan-3-ols are structurally diverse and include a range of compounds, such as <a href="/wiki/Catechin" title="Catechin">catechin</a>, <a href="/wiki/Epicatechin_gallate" title="Epicatechin gallate">epicatechin gallate</a>, <a href="/wiki/Epigallocatechin" class="mw-redirect" title="Epigallocatechin">epigallocatechin</a>, <a href="/wiki/Epigallocatechin_gallate" title="Epigallocatechin gallate">epigallocatechin gallate</a>, <a href="/wiki/Proanthocyanidin" title="Proanthocyanidin">proanthocyanidins</a>, <a href="/wiki/Theaflavin" title="Theaflavin">theaflavins</a>, <a href="/wiki/Thearubigin" title="Thearubigin">thearubigins</a>. They play a part in plant defense and are present in the majority of plants.<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="Chemical_structure">Chemical structure</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Flavan-3-ol&action=edit&section=1" title="Edit section: Chemical structure"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The single-molecule (monomer) catechin, or isomer epicatechin (see diagram), adds four hydroxyls to flavan-3-ol, making building blocks for concatenated polymers (<a href="/wiki/Proanthocyanidin" title="Proanthocyanidin">proanthocyanidins</a>) and higher order polymers (<a href="/wiki/Anthocyanidin" title="Anthocyanidin">anthocyanidins</a>).<sup id="cite_ref-ReferenceA_2-0" class="reference"><a href="#cite_note-ReferenceA-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p><p>Flavan-3-ols possess two chiral carbons, meaning four <a href="/wiki/Diastereoisomer" class="mw-redirect" title="Diastereoisomer">diastereoisomers</a> occur for each of them. They are distinguished from the yellow, ketone-containing flavonoids such as <a href="/wiki/Quercitin" class="mw-redirect" title="Quercitin">quercitin</a> and <a href="/wiki/Rutin" title="Rutin">rutin</a>, which are called <a href="/wiki/Flavonol" class="mw-redirect" title="Flavonol">flav<b>o</b>nols</a>. Early use of the term <b>bioflavonoid</b> was imprecisely applied to include the flavanols, which are distinguished by the absence of ketonse. Catechin monomers, dimers, and trimers (oligomers) are colorless. Higher order polymers, anthocyanidins, exhibit deepening reds and become <a href="/wiki/Tannin" title="Tannin">tannins</a>.<sup id="cite_ref-ReferenceA_2-1" class="reference"><a href="#cite_note-ReferenceA-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p><p><a href="/wiki/Catechin" title="Catechin">Catechin</a> and <a href="/wiki/Epicatechin" class="mw-redirect" title="Epicatechin">epicatechin</a> are <a href="/wiki/Epimer" title="Epimer">epimers</a>, with (–)-epicatechin and (+)-catechin being the most common optical <a href="/wiki/Isomer" title="Isomer">isomers</a> found in nature. Catechin was first isolated from the plant extract <a href="/wiki/Catechu" title="Catechu">catechu</a>, from which it derives its name. Heating catechin past its point of decomposition releases <a href="/wiki/Pyrocatechol" class="mw-redirect" title="Pyrocatechol">pyrocatechol</a> (also called catechol), which explains the common origin of the names of these compounds. </p><p><a href="/wiki/Epigallocatechin" class="mw-redirect" title="Epigallocatechin">Epigallocatechin</a> and <a href="/wiki/Gallocatechin" class="mw-redirect" title="Gallocatechin">gallocatechin</a> contain an additional phenolic <a href="/wiki/Hydroxyl_group" class="mw-redirect" title="Hydroxyl group">hydroxyl group</a> when compared to <a href="/wiki/Epicatechin" class="mw-redirect" title="Epicatechin">epicatechin</a> and <a href="/wiki/Catechin" title="Catechin">catechin</a>, respectively, similar to the difference in <a href="/wiki/Pyrogallol" title="Pyrogallol">pyrogallol</a> compared to <a href="/wiki/Pyrocatechol" class="mw-redirect" title="Pyrocatechol">pyrocatechol</a>. </p><p>Catechin gallates are <a href="/wiki/Gallic_acid" title="Gallic acid">gallic acid</a> <a href="/wiki/Ester" title="Ester">esters</a> of the catechins; an example is <a href="/wiki/Epigallocatechin_gallate" title="Epigallocatechin gallate">epigallocatechin gallate</a>, which is commonly the most abundant catechin in tea. <a href="/wiki/Proanthocyanidin" title="Proanthocyanidin">Proanthocyanidins</a> and <a href="/wiki/Thearubigin" title="Thearubigin">thearubigins</a> are oligomeric flavan-3-ols. </p><p>In contrast to many other <a href="/wiki/Flavonoid" title="Flavonoid">flavonoids</a>, flavan-3-ols do not generally exist as <a href="/wiki/Glycoside" title="Glycoside">glycosides</a> in plants.<sup id="cite_ref-:1_3-0" class="reference"><a href="#cite_note-:1-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Catechin_molecule_file.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/08/Catechin_molecule_file.png/800px-Catechin_molecule_file.png" decoding="async" width="800" height="206" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/08/Catechin_molecule_file.png/1200px-Catechin_molecule_file.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/08/Catechin_molecule_file.png/1600px-Catechin_molecule_file.png 2x" data-file-width="4096" data-file-height="1057" /></a><figcaption>Structures of (epi)catechin, (epi)catechin gallate, (epi)gallocatechin and (epi)gallocatechin gallate.</figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="Biosynthesis_of_(–)-epicatechin"><span id="Biosynthesis_of_.28.E2.80.93.29-epicatechin"></span>Biosynthesis of (–)-epicatechin</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Flavan-3-ol&action=edit&section=2" title="Edit section: Biosynthesis of (–)-epicatechin"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The flavonoids are products from a <a href="/wiki/Cinnamoyl" class="mw-redirect" title="Cinnamoyl">cinnamoyl</a>-CoA starter unit, with chain extension using three molecules of <a href="/wiki/Malonyl" class="mw-redirect" title="Malonyl">malonyl</a>-CoA. Reactions are catalyzed by a type III <a href="/w/index.php?title=PKS_enzyme&action=edit&redlink=1" class="new" title="PKS enzyme (page does not exist)">PKS enzyme</a>. These enzymes do not use ACPSs, but instead employ <a href="/wiki/Coenzyme_A" title="Coenzyme A">coenzyme A</a> esters and have a single active site to perform the necessary series of reactions: chain extension, condensation, and cyclization. Chain extension of 4-hydroxycinnamoyl-CoA with three molecules of malonyl-CoA gives initially a polyketide (Figure 1), which can be folded. These allow <a href="/wiki/Claisen_condensation" title="Claisen condensation">Claisen-like reactions</a> to occur, generating <a href="/wiki/Aromaticity" title="Aromaticity">aromatic rings</a>.<sup id="cite_ref-Dewick2009p168_4-0" class="reference"><a href="#cite_note-Dewick2009p168-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Winkel-Shirley2001p485-493_5-0" class="reference"><a href="#cite_note-Winkel-Shirley2001p485-493-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Fluorescence-lifetime_imaging_microscopy" title="Fluorescence-lifetime imaging microscopy">Fluorescence-lifetime imaging microscopy</a> (FLIM) can be used to detect flavanols in plant cells.<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> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Epicatechin_Biosynthesis-2.png" class="mw-file-description" title="Figure 1"><img alt="Figure 1" src="//upload.wikimedia.org/wikipedia/commons/thumb/4/45/Epicatechin_Biosynthesis-2.png/960px-Epicatechin_Biosynthesis-2.png" decoding="async" width="800" height="638" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/45/Epicatechin_Biosynthesis-2.png/1200px-Epicatechin_Biosynthesis-2.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/45/Epicatechin_Biosynthesis-2.png/1600px-Epicatechin_Biosynthesis-2.png 2x" data-file-width="3375" data-file-height="2690" /></a><figcaption>Figure 1</figcaption></figure> <dl><dd><b>Figure 1</b>: Schematic overview of the flavan-3-ol (–)-epicatechin biosynthesis from <a href="/wiki/Tyrosine" title="Tyrosine">tyrosine</a> (Tyr) or <a href="/wiki/Phenylalanine" title="Phenylalanine">phenylalanine</a> (Phe) in plants. Enzymes are indicated in blue, abbreviated as follows: <dl><dd><style data-mw-deduplicate="TemplateStyles:r1184024115">.mw-parser-output .div-col{margin-top:0.3em;column-width:30em}.mw-parser-output .div-col-small{font-size:90%}.mw-parser-output .div-col-rules{column-rule:1px solid #aaa}.mw-parser-output .div-col dl,.mw-parser-output .div-col ol,.mw-parser-output .div-col ul{margin-top:0}.mw-parser-output .div-col li,.mw-parser-output .div-col dd{page-break-inside:avoid;break-inside:avoid-column}</style><div class="div-col" style="column-width: 30em;"><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>E1: <a href="/wiki/Phenylalanine_ammonia_lyase" class="mw-redirect" title="Phenylalanine ammonia lyase">phenylalanine ammonia lyase</a> (PAL)</li><li>E2: <a href="/wiki/Tyrosine_ammonia_lyase" class="mw-redirect" title="Tyrosine ammonia lyase">tyrosine ammonia lyase</a> (TAL)</li><li>E3: <a href="/wiki/Cinnamate_4-hydroxylase" class="mw-redirect" title="Cinnamate 4-hydroxylase">cinnamate 4-hydroxylase</a></li><li>E4: <a href="/wiki/4-Coumarate-CoA_ligase" title="4-Coumarate-CoA ligase">4-coumaroyl:CoA-ligase</a></li><li>E5: chalcone synthase (<a href="/wiki/Naringenin-chalcone_synthase" class="mw-redirect" title="Naringenin-chalcone synthase">naringenin-chalcone synthase</a>)</li><li>E6: <a href="/wiki/Chalcone_isomerase" title="Chalcone isomerase">chalcone isomerase</a></li><li>E7: <a href="/w/index.php?title=Flavonoid_3%E2%80%B2-hydroxylase&action=edit&redlink=1" class="new" title="Flavonoid 3′-hydroxylase (page does not exist)">flavonoid 3′-hydroxylase</a></li><li>E8: <a href="/w/index.php?title=Flavonone_3-hydroxylase&action=edit&redlink=1" class="new" title="Flavonone 3-hydroxylase (page does not exist)">flavonone 3-hydroxylase</a></li><li>E9: <a href="/wiki/Dihydroflavanol_4-reductase" class="mw-redirect" title="Dihydroflavanol 4-reductase">dihydroflavanol 4-reductase</a></li><li>E10: anthocyanidin synthase (<a href="/wiki/Leucoanthocyanidin_dioxygenase" class="mw-redirect" title="Leucoanthocyanidin dioxygenase">leucoanthocyanidin dioxygenase</a>)</li><li>E11: <a href="/wiki/Anthocyanidin_reductase" title="Anthocyanidin reductase">anthocyanidin reductase</a></li></ul></div></div></dd></dl></dd></dl> <div class="mw-heading mw-heading3"><h3 id="Aglycones">Aglycones</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Flavan-3-ol&action=edit&section=3" title="Edit section: Aglycones"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <table class="wikitable sortable"> <caption>Flavan-3-ols </caption> <tbody><tr> <th>Image</th> <th>Name</th> <th>Formula</th> <th>Oligomers </th></tr> <tr> <td><span typeof="mw:File"><a href="/wiki/File:(%2B)-Catechin.svg" class="mw-file-description" title="(+)-Catechin"><img alt="(+)-Catechin" src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b3/%28%2B%29-Catechin.svg/120px-%28%2B%29-Catechin.svg.png" decoding="async" width="100" height="56" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b3/%28%2B%29-Catechin.svg/250px-%28%2B%29-Catechin.svg.png 1.5x" data-file-width="369" data-file-height="206" /></a></span></td> <td><a href="/wiki/Catechin" title="Catechin">Catechin</a>, C, (+)-Catechin</td> <td>C<sub>15</sub>H<sub>14</sub>O<sub>6</sub></td> <td><a href="/wiki/Procyanidin" title="Procyanidin">Procyanidins</a> </td></tr> <tr> <td><span typeof="mw:File"><a href="/wiki/File:(%E2%80%93)-Epicatechin.svg" class="mw-file-description" title="Epicatechin"><img alt="Epicatechin" src="//upload.wikimedia.org/wikipedia/commons/thumb/0/07/%28%E2%80%93%29-Epicatechin.svg/100px-%28%E2%80%93%29-Epicatechin.svg.png" decoding="async" width="100" height="57" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/07/%28%E2%80%93%29-Epicatechin.svg/150px-%28%E2%80%93%29-Epicatechin.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/07/%28%E2%80%93%29-Epicatechin.svg/200px-%28%E2%80%93%29-Epicatechin.svg.png 2x" data-file-width="660" data-file-height="375" /></a></span></td> <td><a href="/wiki/Epicatechin" class="mw-redirect" title="Epicatechin">Epicatechin</a>, EC, (–)-Epicatechin (<i>cis</i>)</td> <td>C<sub>15</sub>H<sub>14</sub>O<sub>6</sub></td> <td><a href="/wiki/Procyanidin" title="Procyanidin">Procyanidins</a> </td></tr> <tr> <td><span typeof="mw:File"><a href="/wiki/File:Epigallocatechin.svg" class="mw-file-description" title="Epigallocatechin"><img alt="Epigallocatechin" src="//upload.wikimedia.org/wikipedia/commons/thumb/4/40/Epigallocatechin.svg/100px-Epigallocatechin.svg.png" decoding="async" width="100" height="65" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/40/Epigallocatechin.svg/150px-Epigallocatechin.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/40/Epigallocatechin.svg/200px-Epigallocatechin.svg.png 2x" data-file-width="495" data-file-height="324" /></a></span></td> <td><a href="/wiki/Epigallocatechin" class="mw-redirect" title="Epigallocatechin">Epigallocatechin</a>, EGC</td> <td>C<sub>15</sub>H<sub>14</sub>O<sub>7</sub></td> <td><a href="/wiki/Prodelphinidin" title="Prodelphinidin">Prodelphinidins</a> </td></tr> <tr> <td><span typeof="mw:File"><a href="/wiki/File:Epicatechin_gallate.svg" class="mw-file-description" title="Epicatechin gallate"><img alt="Epicatechin gallate" src="//upload.wikimedia.org/wikipedia/commons/thumb/5/5d/Epicatechin_gallate.svg/120px-Epicatechin_gallate.svg.png" decoding="async" width="100" height="91" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/5d/Epicatechin_gallate.svg/250px-Epicatechin_gallate.svg.png 1.5x" data-file-width="620" data-file-height="562" /></a></span></td> <td><a href="/wiki/Epicatechin_gallate" title="Epicatechin gallate">Epicatechin gallate</a>, ECG</td> <td>C<sub>22</sub>H<sub>18</sub>O<sub>10</sub></td> <td> </td></tr> <tr> <td><span typeof="mw:File"><a href="/wiki/File:Epigallocatechin_gallate_structure.svg" class="mw-file-description" title="Epigallocatechin gallate"><img alt="Epigallocatechin gallate" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/2f/Epigallocatechin_gallate_structure.svg/120px-Epigallocatechin_gallate_structure.svg.png" decoding="async" width="100" height="89" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/2f/Epigallocatechin_gallate_structure.svg/250px-Epigallocatechin_gallate_structure.svg.png 1.5x" data-file-width="540" data-file-height="480" /></a></span></td> <td><a href="/wiki/Epigallocatechin_gallate" title="Epigallocatechin gallate">Epigallocatechin gallate</a>, EGCG,<br />(–)-Epigallocatechin gallate</td> <td>C<sub>22</sub>H<sub>18</sub>O<sub>11</sub></td> <td> </td></tr> <tr> <td><span typeof="mw:File"><a href="/wiki/File:Epiafzelechin.svg" class="mw-file-description" title="Epiafzelechin"><img alt="Epiafzelechin" src="//upload.wikimedia.org/wikipedia/commons/thumb/3/3e/Epiafzelechin.svg/120px-Epiafzelechin.svg.png" decoding="async" width="100" height="56" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/3e/Epiafzelechin.svg/250px-Epiafzelechin.svg.png 1.5x" data-file-width="620" data-file-height="348" /></a></span></td> <td><a href="/wiki/Epiafzelechin" class="mw-redirect" title="Epiafzelechin">Epiafzelechin</a></td> <td>C<sub>15</sub>H<sub>14</sub>O<sub>5</sub></td> <td> </td></tr> <tr> <td><span typeof="mw:File"><a href="/wiki/File:Fisetinidol.svg" class="mw-file-description" title="Fisetinidol"><img alt="Fisetinidol" src="//upload.wikimedia.org/wikipedia/commons/thumb/f/ff/Fisetinidol.svg/100px-Fisetinidol.svg.png" decoding="async" width="100" height="45" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/ff/Fisetinidol.svg/150px-Fisetinidol.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/ff/Fisetinidol.svg/200px-Fisetinidol.svg.png 2x" data-file-width="620" data-file-height="282" /></a></span></td> <td><a href="/wiki/Fisetinidol" title="Fisetinidol">Fisetinidol</a></td> <td>C<sub>15</sub>H<sub>14</sub>O<sub>5</sub></td> <td> </td></tr> <tr> <td><span typeof="mw:File"><a href="/wiki/File:Guibourtinidol.svg" class="mw-file-description" title="Guibourtinidol"><img alt="Guibourtinidol" src="//upload.wikimedia.org/wikipedia/commons/thumb/f/fb/Guibourtinidol.svg/120px-Guibourtinidol.svg.png" decoding="async" width="100" height="45" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/fb/Guibourtinidol.svg/250px-Guibourtinidol.svg.png 1.5x" data-file-width="620" data-file-height="282" /></a></span></td> <td><a href="/wiki/Guibourtinidol" title="Guibourtinidol">Guibourtinidol</a></td> <td>C<sub>15</sub>H<sub>14</sub>O<sub>4</sub></td> <td><a href="/wiki/Proguibourtinidin" title="Proguibourtinidin">Proguibourtinidins</a> </td></tr> <tr> <td><span typeof="mw:File"><a href="/wiki/File:Mesquitol.svg" class="mw-file-description" title="Mesquitol"><img alt="Mesquitol" src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0c/Mesquitol.svg/100px-Mesquitol.svg.png" decoding="async" width="100" height="56" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0c/Mesquitol.svg/150px-Mesquitol.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/0c/Mesquitol.svg/200px-Mesquitol.svg.png 2x" data-file-width="620" data-file-height="348" /></a></span></td> <td><a href="/wiki/Mesquitol" title="Mesquitol">Mesquitol</a></td> <td>C<sub>15</sub>H<sub>14</sub>O<sub>6</sub></td> <td> </td></tr> <tr> <td><span typeof="mw:File"><a href="/wiki/File:Robinetinidol.svg" class="mw-file-description" title="Robinetinidol"><img alt="Robinetinidol" src="//upload.wikimedia.org/wikipedia/commons/thumb/0/06/Robinetinidol.svg/100px-Robinetinidol.svg.png" decoding="async" width="100" height="56" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/06/Robinetinidol.svg/150px-Robinetinidol.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/06/Robinetinidol.svg/200px-Robinetinidol.svg.png 2x" data-file-width="620" data-file-height="348" /></a></span></td> <td><a href="/wiki/Robinetinidol" title="Robinetinidol">Robinetinidol</a></td> <td>C<sub>15</sub>H<sub>14</sub>O<sub>6</sub></td> <td><a href="/wiki/Prorobinetinidin" class="mw-redirect" title="Prorobinetinidin">Prorobinetinidins</a> </td></tr></tbody></table> <div class="mw-heading mw-heading2"><h2 id="Dietary_sources">Dietary sources</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Flavan-3-ol&action=edit&section=4" title="Edit section: Dietary sources"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951" /><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/Polyphenols_in_tea" class="mw-redirect" title="Polyphenols in tea">Polyphenols in tea</a>, <a href="/wiki/Polyphenols_in_wine" class="mw-redirect" title="Polyphenols in wine">Polyphenols in wine</a>, and <a href="/wiki/Cocoa_bean#Phytochemicals_and_research" title="Cocoa bean">Cocoa bean § Phytochemicals and research</a></div> <figure class="mw-default-size mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Variability_of_flavan-3-ol_content_in_foods.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/83/Variability_of_flavan-3-ol_content_in_foods.png/250px-Variability_of_flavan-3-ol_content_in_foods.png" decoding="async" width="220" height="220" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/83/Variability_of_flavan-3-ol_content_in_foods.png/330px-Variability_of_flavan-3-ol_content_in_foods.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/83/Variability_of_flavan-3-ol_content_in_foods.png/500px-Variability_of_flavan-3-ol_content_in_foods.png 2x" data-file-width="2099" data-file-height="2099" /></a><figcaption>Reported range of flavan-3-ol content in foods commonly consumed.<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></figcaption></figure> <p>Flavan-3-ols are abundant in <a href="/wiki/Tea" title="Tea">teas</a> derived from the tea plant <i><a href="/wiki/Camellia_sinensis" title="Camellia sinensis">Camellia sinensis</a></i>, as well as in some <a href="/wiki/Cocoa_solids" title="Cocoa solids">cocoas</a> (made from the seeds of <i><a href="/wiki/Theobroma_cacao" title="Theobroma cacao">Theobroma cacao</a></i>), although the content is affected considerably by processing, especially in <a href="/wiki/Chocolate" title="Chocolate">chocolate</a>.<sup id="cite_ref-Hammerstone_2000_8-0" class="reference"><a href="#cite_note-Hammerstone_2000-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Payne_2010_9-0" class="reference"><a href="#cite_note-Payne_2010-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> Flavan-3-ols are also present in the human diet in fruits, in particular <a href="/wiki/Pome" title="Pome">pome fruits</a>, <a href="/wiki/Berry" title="Berry">berries</a>, <a href="/wiki/Vegetable" title="Vegetable">vegetables</a>, and <a href="/wiki/Wine" title="Wine">wine</a>.<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> Their content in food is variable and affected by various factors, such as <a href="/wiki/Cultivar" title="Cultivar">cultivar</a>, <a href="/wiki/Food_processing" title="Food processing">processing</a>, and <a href="/wiki/Outline_of_food_preparation" title="Outline of food preparation">preparation</a>.<sup id="cite_ref-:2_11-0" class="reference"><a href="#cite_note-:2-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Bioavailability_and_metabolism">Bioavailability and metabolism</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Flavan-3-ol&action=edit&section=5" title="Edit section: Bioavailability and metabolism"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The <a href="/wiki/Bioavailability" title="Bioavailability">bioavailability</a> of flavan-3-ols depends on the <a href="/wiki/Human_nutrition" title="Human nutrition">food matrix</a>, type of compound and their <a href="/wiki/Stereochemistry" title="Stereochemistry">stereochemical</a> configuration.<sup id="cite_ref-:1_3-1" class="reference"><a href="#cite_note-:1-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> While monomeric flavan-3-ols are readily taken up, oligomeric forms are not absorbed.<sup id="cite_ref-:1_3-2" class="reference"><a href="#cite_note-:1-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> Most data for human metabolism of flavan-3-ols are available for monomeric compounds, especially <a href="/wiki/Catechin" title="Catechin">epiatechin</a>. These compounds are taken up and metabolized upon uptake in the <a href="/wiki/Jejunum" title="Jejunum">jejunum</a>,<sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> mainly by <i>O</i>-methylation and glucuronidation,<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> and then further <a href="/wiki/Drug_metabolism" title="Drug metabolism">metabolized</a> by the <a href="/wiki/Liver" title="Liver">liver</a>. The colonic <a href="/wiki/Human_microbiota" class="mw-redirect" title="Human microbiota">microbiome</a> has also an important role in the metabolism of flavan-3-ols and they are catabolized to smaller compounds such as 5-(3′/4′-dihydroxyphenyl)-γ-valerolactones and <a href="/wiki/Hippuric_acid" title="Hippuric acid">hippuric acid</a>.<sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-:0_16-0" class="reference"><a href="#cite_note-:0-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> Only flavan-3-ols with an intact (epi)catechin moiety can be metabolized into 5-(3′/4′-dihydroxyphenyl)-γ-valerolactones (image in Gallery).<sup id="cite_ref-Ottaviani_9859_17-0" class="reference"><a href="#cite_note-Ottaviani_9859-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Possible_adverse_effects">Possible adverse effects</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Flavan-3-ol&action=edit&section=6" title="Edit section: Possible adverse effects"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>As catechins in <a href="/wiki/Green_tea" title="Green tea">green tea</a> <a href="/wiki/Extract" title="Extract">extract</a> can be <a href="/wiki/Hepatotoxicity" title="Hepatotoxicity">hepatotoxic</a>, <a href="/wiki/Health_Canada" title="Health Canada">Health Canada</a> and EFSA have advised for caution,<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> recommending intake should not exceed 800 mg per day.<sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Research">Research</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Flavan-3-ol&action=edit&section=7" title="Edit section: Research"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951" /><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/Cocoa_bean#Phytochemicals_and_research" title="Cocoa bean">Cocoa bean § Phytochemicals and research</a></div> <p>Research has shown that flavan-3-ols may affect <a href="/wiki/Vascular_system" class="mw-redirect" title="Vascular system">vascular function</a>, <a href="/wiki/Blood_pressure" title="Blood pressure">blood pressure</a>, and <a href="/wiki/Blood_lipids" title="Blood lipids">blood lipids</a>, with only minor effects demonstrated, as of 2019.<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><sup id="cite_ref-raman_21-0" class="reference"><a href="#cite_note-raman-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> In 2015, the <a href="/wiki/European_Commission" title="European Commission">European Commission</a> approved a <a href="/wiki/Health_claim" title="Health claim">health claim</a> for <a href="/wiki/Cocoa_solid" class="mw-redirect" title="Cocoa solid">cocoa solids</a> containing 200 mg of flavanols, stating that such intake "may contribute to maintenance of vascular elasticity and normal blood flow".<sup id="cite_ref-EC-cocoa_22-0" class="reference"><a href="#cite_note-EC-cocoa-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-efsa2014_23-0" class="reference"><a href="#cite_note-efsa2014-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> As of 2022, food-based evidence indicates that intake of 400–600 mg per day of flavan-3-ols could have a small positive effect on cardiovascular <a href="/wiki/Biomarker" title="Biomarker">biomarkers</a>.<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> </p> <div class="mw-heading mw-heading2"><h2 id="Gallery">Gallery</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Flavan-3-ol&action=edit&section=8" title="Edit section: Gallery"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul class="gallery mw-gallery-traditional"> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><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" title="Schematic representation of the flavan-3-ol (−)-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.[16]"><img alt="Schematic representation of the flavan-3-ol (−)-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.[16]" 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/120px-Schematic_representation_of_%28%E2%88%92%29-epicatechin_metabolism_in_humans_as_a_function_of_time_post-oral_intake.jpg" decoding="async" width="112" height="120" 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/250px-Schematic_representation_of_%28%E2%88%92%29-epicatechin_metabolism_in_humans_as_a_function_of_time_post-oral_intake.jpg 1.5x" data-file-width="926" data-file-height="989" /></a></span></div> <div class="gallerytext">Schematic representation of the flavan-3-ol (−)-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-:0_16-1" class="reference"><a href="#cite_note-:0-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup></div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Flavan-3-ol_precursors_of_the_microbial_metabolite_5-(3%E2%80%B2-4%E2%80%B2-dihydroxyphenyl)-%CE%B3-valerolactone.jpg" class="mw-file-description" title="Flavan-3-ol precursors of the microbial metabolite 5-(3′/4′-dihydroxyphenyl)-γ-valerolactone (γVL). Only compounds with intact (epi)catechin moiety result in the formation of γVL by the intestinal microbiome. ECG, (−)-epicatechin-3-O-gallate; EGCG, Epigallocatechin gallate; EGC, Epigallocatechin.[17]"><img alt="Flavan-3-ol precursors of the microbial metabolite 5-(3′/4′-dihydroxyphenyl)-γ-valerolactone (γVL). Only compounds with intact (epi)catechin moiety result in the formation of γVL by the intestinal microbiome. ECG, (−)-epicatechin-3-O-gallate; EGCG, Epigallocatechin gallate; EGC, Epigallocatechin.[17]" src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f6/Flavan-3-ol_precursors_of_the_microbial_metabolite_5-%283%E2%80%B2-4%E2%80%B2-dihydroxyphenyl%29-%CE%B3-valerolactone.jpg/120px-Flavan-3-ol_precursors_of_the_microbial_metabolite_5-%283%E2%80%B2-4%E2%80%B2-dihydroxyphenyl%29-%CE%B3-valerolactone.jpg" decoding="async" width="120" height="93" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f6/Flavan-3-ol_precursors_of_the_microbial_metabolite_5-%283%E2%80%B2-4%E2%80%B2-dihydroxyphenyl%29-%CE%B3-valerolactone.jpg/250px-Flavan-3-ol_precursors_of_the_microbial_metabolite_5-%283%E2%80%B2-4%E2%80%B2-dihydroxyphenyl%29-%CE%B3-valerolactone.jpg 1.5x" data-file-width="900" data-file-height="701" /></a></span></div> <div class="gallerytext">Flavan-3-ol precursors of the microbial metabolite 5-(3′/4′-dihydroxyphenyl)-γ-valerolactone (γVL). Only compounds with intact (epi)catechin moiety result in the formation of γVL by the intestinal microbiome. ECG, (−)-epicatechin-3-<i>O</i>-gallate; EGCG, <a href="/wiki/Epigallocatechin_gallate" title="Epigallocatechin gallate">Epigallocatechin gallate</a>; EGC, <a href="/wiki/Epigallocatechin" class="mw-redirect" title="Epigallocatechin">Epigallocatechin</a>.<sup id="cite_ref-Ottaviani_9859_17-1" class="reference"><a href="#cite_note-Ottaviani_9859-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup></div> </li> </ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Flavan-3-ol&action=edit&section=9" 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"> <div class="mw-references-wrap mw-references-columns"><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 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Retrieved <span class="nowrap">8 September</span> 2022</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Article+13%285%29%3A+Cocoa+flavanols%3B+Search+filters%3A+Claim+status+-+authorised%3B+search+-+flavanols&rft.pub=European+Commission%2C+EU+Register&rft.date=2015-03-31&rft_id=https%3A%2F%2Fec.europa.eu%2Ffood%2Fsafety%2Flabelling_nutrition%2Fclaims%2Fregister%2Fpublic%2F%3Fevent%3Dsearch&rfr_id=info%3Asid%2Fen.wikipedia.org%3AFlavan-3-ol" class="Z3988"></span></span> </li> <li id="cite_note-efsa2014-23"><span class="mw-cite-backlink"><b><a href="#cite_ref-efsa2014_23-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation journal cs1"><a rel="nofollow" class="external text" href="https://doi.org/10.2903%2Fj.efsa.2014.3654">"Scientific Opinion on the modification of the authorisation of a health claim related to cocoa flavanols and maintenance of normal endothelium-dependent vasodilation pursuant to Article 13(5) of Regulation (EC) No 1924/20061 following a request in accordance with Article 19 of Regulation (EC) No 1924/2006"</a>. <i>EFSA Journal</i>. <b>12</b> (5). 2014. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.2903%2Fj.efsa.2014.3654">10.2903/j.efsa.2014.3654</a></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=EFSA+Journal&rft.atitle=Scientific+Opinion+on+the+modification+of+the+authorisation+of+a+health+claim+related+to+cocoa+flavanols+and+maintenance+of+normal+endothelium-dependent+vasodilation+pursuant+to+Article+13%285%29+of+Regulation+%28EC%29+No+1924%2F20061+following+a+request+in+accordance+with+Article+19+of+Regulation+%28EC%29+No+1924%2F2006&rft.volume=12&rft.issue=5&rft.date=2014&rft_id=info%3Adoi%2F10.2903%2Fj.efsa.2014.3654&rft_id=https%3A%2F%2Fdoi.org%2F10.2903%252Fj.efsa.2014.3654&rfr_id=info%3Asid%2Fen.wikipedia.org%3AFlavan-3-ol" class="Z3988"></span></span> </li> <li id="cite_note-24"><span class="mw-cite-backlink"><b><a href="#cite_ref-24">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFCrowe-WhiteEvansKuhnleMilenkovic2022" class="citation journal cs1">Crowe-White KM, Evans LW, Kuhnle GG, Milenkovic D, Stote K, Wallace T, Handu D, Senkus KE (3 October 2022). <a rel="nofollow" class="external text" href="https://academic.oup.com/advances/article/13/6/2070/6747118">"Flavan-3-ols and cardiometabolic health: First ever dietary bioactive guideline"</a>. <i>Advances in Nutrition</i>. <b>13</b> (6): <span class="nowrap">2070–</span>2083. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1093%2Fadvances%2Fnmac105">10.1093/advances/nmac105</a></span>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9776652">9776652</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/36190328">36190328</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Advances+in+Nutrition&rft.atitle=Flavan-3-ols+and+cardiometabolic+health%3A+First+ever+dietary+bioactive+guideline&rft.volume=13&rft.issue=6&rft.pages=%3Cspan+class%3D%22nowrap%22%3E2070-%3C%2Fspan%3E2083&rft.date=2022-10-03&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC9776652%23id-name%3DPMC&rft_id=info%3Apmid%2F36190328&rft_id=info%3Adoi%2F10.1093%2Fadvances%2Fnmac105&rft.aulast=Crowe-White&rft.aufirst=Kristi+M&rft.au=Evans%2C+Levi+W&rft.au=Kuhnle%2C+Gunter+G+C&rft.au=Milenkovic%2C+Dragan&rft.au=Stote%2C+Kim&rft.au=Wallace%2C+Taylor&rft.au=Handu%2C+Deepa&rft.au=Senkus%2C+Katelyn+E&rft_id=https%3A%2F%2Facademic.oup.com%2Fadvances%2Farticle%2F13%2F6%2F2070%2F6747118&rfr_id=info%3Asid%2Fen.wikipedia.org%3AFlavan-3-ol" class="Z3988"></span></span> </li> </ol></div></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=Flavan-3-ol&action=edit&section=10" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><span class="noviewer" typeof="mw:File"><a href="/wiki/File:Commons-logo.svg" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/20px-Commons-logo.svg.png" decoding="async" width="12" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/40px-Commons-logo.svg.png 2x" data-file-width="1024" data-file-height="1376" /></a></span> Media related to <a href="https://commons.wikimedia.org/wiki/Category:Flavan-3-ols" class="extiw" title="commons:Category:Flavan-3-ols">Flavan-3-ols</a> at Wikimedia Commons</li></ul> <div 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title="Flavonoid">Flavonoids</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Anthoxanthin" title="Anthoxanthin">Anthoxanthins</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Flavone" title="Flavone">Flavones</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Apigenin" title="Apigenin">Apigenin</a>, <a href="/wiki/Chrysin" title="Chrysin">Chrysin</a>, et.c.</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Flavonols" title="Flavonols">Flavonols</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Quercetin" title="Quercetin">Quercetin</a>, <a href="/wiki/Kaempferol" title="Kaempferol">Kaempferol</a>, et.c.</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Isoflavones" class="mw-redirect" title="Isoflavones">Isoflavones</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Daidzein" title="Daidzein">Daidzein</a>, <a href="/wiki/Genistein" title="Genistein">Genistein</a>, <a href="/wiki/Orobol" title="Orobol">Orobol</a> et.c.</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Neoflavonoid" title="Neoflavonoid">Neoflavonoids</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Dalbergichromene" title="Dalbergichromene">Dalbergichromene</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Flavan" title="Flavan">Flavans</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">Flavan</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=Luteoliflavan&action=edit&redlink=1" class="new" title="Luteoliflavan (page does not exist)">Luteoliflavan</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a class="mw-selflink selflink">Flavan-3-ols</a><br />(<a href="/wiki/Flavanol" class="mw-redirect" title="Flavanol">flavanols</a>)</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Catechin" title="Catechin">Catechin</a>, <a href="/wiki/Gallocatechol" title="Gallocatechol">Gallocatechol</a>, et.c.</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Flavan-4-ol" title="Flavan-4-ol">Flavan-4-ols</a><br />(<a href="/wiki/Flavanol" class="mw-redirect" title="Flavanol">flavanols</a>)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Apiforol" title="Apiforol">Apiforol</a>, <a href="/wiki/Luteoforol" title="Luteoforol">Luteoforol</a>, et.c.</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Leucoanthocyanidin" title="Leucoanthocyanidin">Flavan-3,4-diols</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Leucocyanidin" title="Leucocyanidin">Leucocyanidin</a>, <a href="/wiki/Leucodelphinidin" title="Leucodelphinidin">Leucodelphinidin</a>, et.c.</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Flavanone" title="Flavanone">Flavanones</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Hesperidin" title="Hesperidin">Hesperidin</a></li> <li><a href="/wiki/Naringenin" title="Naringenin">Naringenin</a></li> <li><a href="/wiki/Eriodictyol" title="Eriodictyol">Eriodictyol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Flavanonol" title="Flavanonol">Flavanonols</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Taxifolin" title="Taxifolin">Taxifolin</a></li> <li><a href="/wiki/Aromadendrin" title="Aromadendrin">Aromadendrin</a>, et.c.</li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Anthocyanidins" class="mw-redirect" title="Anthocyanidins">Anthocyanidins</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/3-deoxyanthocyanidin" class="mw-redirect" title="3-deoxyanthocyanidin">3-deoxyanthocyanidins</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cyanidin" title="Cyanidin">Cyanidin</a>, <a href="/wiki/Delphinidin" title="Delphinidin">Delphinidin</a>, et.c.</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/w/index.php?title=3-hydroxyanthocyanidin&action=edit&redlink=1" class="new" title="3-hydroxyanthocyanidin (page does not exist)">3-hydroxyanthocyanidin</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Apigeninidin" title="Apigeninidin">Apigeninidin</a>, <a href="/wiki/Guibourtinidin" title="Guibourtinidin">Guibourtinidin</a>, et.c.</li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Aurones" class="mw-redirect" title="Aurones">Aurones</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Aureusidin" title="Aureusidin">Aureusidin</a></li> <li><a href="/wiki/Leptosidin" title="Leptosidin">Leptosidin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Chalcones" class="mw-redirect" title="Chalcones">Chalcones</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Chalcone" title="Chalcone">Chalcones</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Butein" title="Butein">Butein</a>, <a href="/wiki/Isoliquiritigenin" title="Isoliquiritigenin">Isoliquiritigenin</a>, et.c.</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Dihydrochalcone" title="Dihydrochalcone">Dihydrochalcone</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Phloretin" title="Phloretin">Phloretin</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><i>Miscellaneous</i></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/List_of_phytochemicals_in_food" title="List of phytochemicals in food">List of phytochemicals in food</a></li> <li><a href="/wiki/C-methylated_flavonoid" title="C-methylated flavonoid">C-methylated flavonoids</a></li> <li><a href="/wiki/O-methylated_flavonoid" title="O-methylated flavonoid">O-methylated flavonoids</a></li> <li><a href="/wiki/Furanoflavonoid" title="Furanoflavonoid">Furanoflavonoids</a></li> <li><a href="/wiki/Pyranoflavonoid" title="Pyranoflavonoid">Pyranoflavonoids</a></li> <li><a href="/wiki/Prenylflavonoid" title="Prenylflavonoid">Prenylflavonoids</a></li> <li><a href="/wiki/Methylenedioxy" title="Methylenedioxy">Methylenedioxy</a></li> <li><a href="/wiki/Castavinol" title="Castavinol">Castavinols</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div><a href="/wiki/Flavonoid_biosynthesis" title="Flavonoid biosynthesis">Flavonoid biosynthesis</a></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /></div><div role="navigation" class="navbox" aria-labelledby="Flavan-3-ols_and_their_glycosides116" 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" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231" /><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template: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_glycosides116" 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 class="mw-selflink selflink">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 href="/wiki/Catechin" title="Catechin">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%27-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 class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /></div><div role="navigation" class="navbox" aria-labelledby="Chocolate749" 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" style="background: #7B3F00; color: white;"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231" /><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Chocolate" title="Template:Chocolate"><abbr title="View this template" style="color: white">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Chocolate" title="Template talk:Chocolate"><abbr title="Discuss this template" style="color: white">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Chocolate" title="Special:EditPage/Template:Chocolate"><abbr title="Edit this template" style="color: white">e</abbr></a></li></ul></div><div id="Chocolate749" style="font-size:114%;margin:0 4em"><a href="/wiki/Chocolate" title="Chocolate"><span style="color:white">Chocolate</span></a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;background: #7B3F00; color: white;"><a href="/wiki/Cocoa_bean" title="Cocoa bean"><span style="color:white">Cocoa bean</span></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/Chocolate_liquor" title="Chocolate liquor">Chocolate liquor</a></li> <li><a href="/wiki/Cocoa_butter" title="Cocoa butter">Cocoa butter</a></li> <li><a href="/wiki/Cocoa_solids" title="Cocoa solids">Cocoa solids</a></li> <li><i><a href="/wiki/Theobroma_cacao" title="Theobroma cacao">Theobroma cacao</a></i></li> <li><a href="/wiki/Types_of_cocoa_beans" title="Types of cocoa beans">Types</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background: #7B3F00; color: white;">Components</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/Anandamide" title="Anandamide">Anandamide</a></li> <li><a href="/wiki/Caffeine" title="Caffeine">Caffeine</a></li> <li><a href="/wiki/Endorphins" title="Endorphins">Endorphins</a></li> <li><a href="/wiki/Enkephalin" title="Enkephalin">Enkephalin</a></li> <li><a class="mw-selflink selflink">Flavan-3-ol</a></li> <li><a href="/wiki/Lecithin" title="Lecithin">Lecithin</a></li> <li><a href="/wiki/Phenethylamine" title="Phenethylamine">Phenethylamine</a></li> <li><a href="/wiki/Phenylalanine" title="Phenylalanine">Phenylalanine</a></li> <li><a href="/wiki/Salsolinol" title="Salsolinol">Salsolinol</a></li> <li><a href="/wiki/Tetramethylpyrazine" title="Tetramethylpyrazine">Tetramethylpyrazine</a></li> <li><a href="/wiki/Theobromine" title="Theobromine">Theobromine</a></li> <li><a href="/wiki/Theophylline" title="Theophylline">Theophylline</a></li> <li><a href="/wiki/Tryptamine" title="Tryptamine">Tryptamine</a></li> <li><a href="/wiki/Tryptophan" title="Tryptophan">Tryptophan</a></li> <li><a href="/wiki/Tyramine" title="Tyramine">Tyramine</a></li> <li><a href="/wiki/Tyrosine" title="Tyrosine">Tyrosine</a></li> <li><a href="/wiki/Valeric_acid" title="Valeric acid">Valeric acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background: #7B3F00; color: white;"><a href="/wiki/Types_of_chocolate" title="Types of chocolate"><span style="color:white">Types</span></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/Baking_chocolate" title="Baking chocolate">Baking</a></li> <li><a href="/wiki/Compound_chocolate" title="Compound chocolate">Compound</a></li> <li><a href="/wiki/Couverture_chocolate" title="Couverture chocolate">Couverture</a></li> <li><a href="/wiki/Dark_chocolate" title="Dark chocolate">Dark</a></li> <li><a href="/wiki/Gianduja_(chocolate)" title="Gianduja (chocolate)">Gianduja</a></li> <li><a href="/wiki/Milk_chocolate" title="Milk chocolate">Milk</a></li> <li><a href="/wiki/Organic_chocolate" title="Organic chocolate">Organic</a></li> <li><a href="/wiki/Raw_chocolate" title="Raw chocolate">Raw</a></li> <li><a href="/wiki/Ruby_chocolate" title="Ruby chocolate">Ruby</a></li> <li><a href="/wiki/White_chocolate" title="White chocolate">White</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background: #7B3F00; color: white;">Products</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/List_of_chocolate_drinks" title="List of chocolate drinks">Beverages</a> <ul><li><a href="/wiki/Caff%C3%A8_mocha" title="Caffè mocha">Caffè mocha</a></li> <li><a href="/wiki/Chocolate_milk" title="Chocolate milk">Milk</a></li> <li><a href="/wiki/Hot_chocolate" title="Hot chocolate">Hot chocolate</a></li> <li><a href="/wiki/Chocolate_liqueur" title="Chocolate liqueur">Liqueur</a></li></ul></li> <li><a href="/wiki/Chocolate_biscuit" title="Chocolate biscuit">Biscuit</a></li> <li><a href="/wiki/Chocolate_brownie" title="Chocolate brownie">Brownie</a></li> <li><a href="/wiki/Chocolate_cake" title="Chocolate cake">Cake</a></li> <li><a href="/wiki/Chocolate_bar" title="Chocolate bar">Chocolate bar</a> <ul><li><a href="/wiki/List_of_chocolate_bar_brands" title="List of chocolate bar brands">Brands</a></li></ul></li> <li><a href="/wiki/Chocolate_chip" title="Chocolate chip">Chocolate chip</a></li> <li><a href="/wiki/Chocolate_chip_cookie" title="Chocolate chip cookie">Chocolate chip cookie</a></li> <li><a href="/wiki/List_of_chocolate-covered_foods" title="List of chocolate-covered foods">Chocolate-covered foods</a></li> <li><a href="/wiki/Chocolate_crackles" title="Chocolate crackles">Chocolate crackles</a></li> <li><a href="/wiki/Cioccolato_di_Modica" title="Cioccolato di Modica">Cioccolato di Modica</a></li> <li><a href="/wiki/Chocolate_coin" title="Chocolate coin">Coins</a></li> <li><a href="/wiki/Fudge" title="Fudge">Fudge</a></li> <li><a href="/wiki/Ganache" title="Ganache">Ganache</a></li> <li><a href="/wiki/Chocolate_gravy" title="Chocolate gravy">Gravy</a></li> <li><a href="/wiki/Chocolate_ice_cream" title="Chocolate ice cream">Ice cream</a></li> <li><a href="/wiki/Mole_(sauce)" title="Mole (sauce)">Mole</a></li> <li><a href="/wiki/Chocolate_pudding" title="Chocolate pudding">Pudding</a></li> <li><a href="/wiki/Chocolate_spread" title="Chocolate spread">Spread</a></li> <li><a href="/wiki/Chocolate_syrup" title="Chocolate syrup">Syrup</a></li> <li><a href="/wiki/Chocolate_truffle" title="Chocolate truffle">Truffle</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background: #7B3F00; color: white;">Processes</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/Aerated_chocolate" title="Aerated chocolate">Aeration</a></li> <li><a href="/wiki/Broma_process" title="Broma process">Broma process</a></li> <li><a href="/wiki/Conching" title="Conching">Conching</a></li> <li><a href="/wiki/Dutch_process_cocoa" title="Dutch process cocoa">Dutch process</a></li> <li><a href="/wiki/Enrober" title="Enrober">Enrober</a></li> <li><a href="/wiki/Sugar_crust" title="Sugar crust">Sugar crust</a></li> <li><a href="/wiki/Tempered_chocolate" title="Tempered chocolate">Tempering</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background: #7B3F00; color: white;">Industry</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/Bean-to-bar" title="Bean-to-bar">Bean-to-bar</a> <ul><li><a href="/wiki/List_of_bean-to-bar_chocolate_manufacturers" title="List of bean-to-bar chocolate manufacturers">Manufacturers</a></li></ul></li> <li><a href="/wiki/Big_Chocolate" title="Big Chocolate">Big Chocolate</a></li> <li><a href="/wiki/Chocolaterie" title="Chocolaterie">Chocolaterie</a></li> <li><a href="/wiki/Chocolatier" title="Chocolatier">Chocolatier</a></li> <li><a href="/wiki/C%C3%B4te_d%27Ivoire%E2%80%93Ghana_Cocoa_Initiative" title="Côte d'Ivoire–Ghana Cocoa Initiative">Côte d'Ivoire–Ghana Cocoa Initiative</a></li> <li><a href="/wiki/Environmental_impact_of_cocoa_production" title="Environmental impact of cocoa production">Environmental impact</a></li> <li><a href="/wiki/Fair_trade_cocoa" title="Fair trade cocoa">Fair trade cocoa</a> <ul><li><a href="/wiki/Child_labour_in_cocoa_production" title="Child labour in cocoa production">Child labour in cocoa production</a></li></ul></li> <li><a href="/wiki/Harkin%E2%80%93Engel_Protocol" title="Harkin–Engel Protocol">Harkin–Engel Protocol</a></li> <li><a href="/wiki/International_Cocoa_Organization" title="International Cocoa Organization">International Cocoa Organization</a></li> <li><a href="/wiki/International_Cocoa_Quarantine_Centre" title="International Cocoa Quarantine Centre">International Cocoa Quarantine Centre</a></li> <li><a href="/wiki/Cocoa_production_in_Ghana" title="Cocoa production in Ghana">Production in Ghana</a> <ul><li><a href="/wiki/Ghana_Cocoa_Board" title="Ghana Cocoa Board">Ghana Cocoa Board</a></li></ul></li> <li><a href="/wiki/Cocoa_production_in_Ivory_Coast" title="Cocoa production in Ivory Coast">Production in Ivory Coast</a></li> <li><a href="/wiki/Cocoa_production_in_Nigeria" title="Cocoa production in Nigeria">Production in Nigeria</a></li> <li><a href="/wiki/Cocoa_production_in_S%C3%A3o_Tom%C3%A9_and_Pr%C3%ADncipe" title="Cocoa production in São Tomé and Príncipe">Production in São Tomé and Príncipe</a></li> <li><a href="/wiki/World_Cocoa_Foundation" title="World Cocoa Foundation">World Cocoa Foundation</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background: #7B3F00; color: white;">By country</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/Belgian_chocolate" title="Belgian chocolate">Belgium</a></li> <li><a href="/wiki/French_chocolate" title="French chocolate">France</a></li> <li><a href="/wiki/Swiss_chocolate" title="Swiss chocolate">Switzerland</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background: #7B3F00; color: white;">Other topics</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/Chocolate_bloom" title="Chocolate bloom">Chocolate bloom</a></li> <li><a href="/wiki/Chocolate_fountain" title="Chocolate fountain">Chocolate fountain</a></li> <li><a href="/wiki/List_of_chocolate_museums" title="List of chocolate museums">Chocolate museums</a></li> <li><a href="/wiki/List_of_chocolatiers" title="List of chocolatiers">Chocolatiers</a></li> <li><a href="/wiki/Cocoa_smuggling" title="Cocoa smuggling">Cocoa smuggling</a></li> <li><a href="/wiki/History_of_chocolate" title="History of chocolate">History</a></li> <li><a href="/wiki/Chocolate_in_savory_cooking" title="Chocolate in savory cooking">In savory cooking</a></li> <li>Military chocolate <ul><li><a href="/wiki/Military_chocolate_(Switzerland)" title="Military chocolate (Switzerland)">Switzerland</a></li> <li><a href="/wiki/Military_chocolate_(United_States)" title="Military chocolate (United States)">United States</a></li></ul></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2" style="background: #7B3F00; color: white;"><div><div class="plainlist"> <ul><li><span class="noviewer" typeof="mw:File"><span title="Category"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/16px-Symbol_category_class.svg.png" decoding="async" width="16" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/23px-Symbol_category_class.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/31px-Symbol_category_class.svg.png 2x" data-file-width="180" data-file-height="185" /></span></span> <b><a href="/wiki/Category:Chocolate" title="Category:Chocolate"><span style="color:white">Category</span></a></b></li> <li><span class="noviewer" typeof="mw:File"><span title="Outline"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/4/41/Global_thinking.svg/20px-Global_thinking.svg.png" decoding="async" width="10" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/41/Global_thinking.svg/40px-Global_thinking.svg.png 2x" data-file-width="130" data-file-height="200" /></span></span> <b><a href="/wiki/Outline_of_chocolate" title="Outline of chocolate"><span style="color:white">Outline</span></a></b></li> <li><span class="noviewer" typeof="mw:File"><span><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/e/e0/Symbol_question.svg/20px-Symbol_question.svg.png" decoding="async" width="16" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/e/e0/Symbol_question.svg/40px-Symbol_question.svg.png 1.5x" data-file-width="180" data-file-height="185" /></span></span> <b><a href="/wiki/Glossary_of_chocolate_terms" title="Glossary of chocolate terms"><span 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