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class="vector-toc-link" href="#Grape_polyphenols"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>Grape polyphenols</span> </div> </a> <button aria-controls="toc-Grape_polyphenols-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 Grape polyphenols subsection</span> </button> <ul id="toc-Grape_polyphenols-sublist" class="vector-toc-list"> <li id="toc-Flavonoids" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Flavonoids"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.1</span> <span>Flavonoids</span> </div> </a> <ul id="toc-Flavonoids-sublist" class="vector-toc-list"> <li id="toc-Flavonols" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Flavonols"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.1.1</span> <span>Flavonols</span> </div> </a> <ul id="toc-Flavonols-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Anthocyanins" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Anthocyanins"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.1.2</span> <span>Anthocyanins</span> </div> </a> <ul id="toc-Anthocyanins-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Tannins" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Tannins"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.1.3</span> <span>Tannins</span> </div> </a> <ul id="toc-Tannins-sublist" class="vector-toc-list"> <li id="toc-Addition_of_enological_tannins" class="vector-toc-list-item vector-toc-level-4"> <a class="vector-toc-link" href="#Addition_of_enological_tannins"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.1.3.1</span> <span>Addition of enological tannins</span> </div> </a> <ul id="toc-Addition_of_enological_tannins-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Effects_of_tannins_on_the_drinkability_and_aging_potential_of_wine" class="vector-toc-list-item vector-toc-level-4"> <a class="vector-toc-link" href="#Effects_of_tannins_on_the_drinkability_and_aging_potential_of_wine"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.1.3.2</span> <span>Effects of tannins on the drinkability and aging potential of wine</span> </div> </a> <ul id="toc-Effects_of_tannins_on_the_drinkability_and_aging_potential_of_wine-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> </ul> </li> <li id="toc-Other_flavonoids" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Other_flavonoids"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.2</span> <span>Other flavonoids</span> </div> </a> <ul id="toc-Other_flavonoids-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Non-flavonoids" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Non-flavonoids"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.3</span> <span>Non-flavonoids</span> </div> </a> <ul id="toc-Non-flavonoids-sublist" class="vector-toc-list"> <li id="toc-Hydroxycinnamic_acids" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Hydroxycinnamic_acids"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.3.1</span> <span>Hydroxycinnamic acids</span> </div> </a> <ul id="toc-Hydroxycinnamic_acids-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Stilbenoids" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Stilbenoids"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.3.2</span> <span>Stilbenoids</span> </div> </a> <ul id="toc-Stilbenoids-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Phenolic_acids" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Phenolic_acids"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.3.3</span> <span>Phenolic acids</span> </div> </a> <ul id="toc-Phenolic_acids-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> </ul> </li> <li id="toc-Phenols_from_oak_ageing" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Phenols_from_oak_ageing"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Phenols from oak ageing</span> </div> </a> <ul id="toc-Phenols_from_oak_ageing-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Natural_phenols_and_polyphenols_from_cork_stoppers" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Natural_phenols_and_polyphenols_from_cork_stoppers"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Natural phenols and polyphenols from cork stoppers</span> </div> </a> <ul id="toc-Natural_phenols_and_polyphenols_from_cork_stoppers-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Phenolic_content_in_relation_with_wine_making_techniques" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Phenolic_content_in_relation_with_wine_making_techniques"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Phenolic content in relation with wine making techniques</span> </div> </a> <button aria-controls="toc-Phenolic_content_in_relation_with_wine_making_techniques-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 Phenolic content in relation with wine making techniques subsection</span> </button> <ul id="toc-Phenolic_content_in_relation_with_wine_making_techniques-sublist" class="vector-toc-list"> <li id="toc-Extraction_levels_in_relation_with_grape_pressing_techniques" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Extraction_levels_in_relation_with_grape_pressing_techniques"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1</span> <span>Extraction levels in relation with grape pressing techniques</span> </div> </a> <ul id="toc-Extraction_levels_in_relation_with_grape_pressing_techniques-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Microoxygeneation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Microoxygeneation"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.2</span> <span>Microoxygeneation</span> </div> </a> <ul id="toc-Microoxygeneation-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Phenolic_compounds_found_in_wine" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Phenolic_compounds_found_in_wine"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Phenolic compounds found in wine</span> </div> </a> <ul id="toc-Phenolic_compounds_found_in_wine-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Effects" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Effects"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Effects</span> </div> </a> <ul id="toc-Effects-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>See also</span> </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</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">10</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" 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href="https://de.wikipedia.org/wiki/Phenole_im_Wein" title="Phenole im Wein – German" lang="de" hreflang="de" data-title="Phenole im Wein" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Contenido_fen%C3%B3lico_del_vino" title="Contenido fenólico del vino – Spanish" lang="es" hreflang="es" data-title="Contenido fenólico del vino" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D9%85%D8%AD%D8%AA%D9%88%D8%A7%DB%8C_%D9%81%D9%86%D9%88%D9%84%DB%8C_%D8%AF%D8%B1_%D8%B4%D8%B1%D8%A7%D8%A8" title="محتوای فنولی در شراب – Persian" lang="fa" hreflang="fa" data-title="محتوای فنولی در شراب" 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/Contenu_ph%C3%A9nolique_du_vin" title="Contenu phénolique du vin – French" lang="fr" hreflang="fr" data-title="Contenu phénolique du vin" 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/%ED%8F%AC%EB%8F%84%EC%A3%BC%EC%9D%98_%ED%8E%98%EB%86%80_%EC%84%B1%EB%B6%84" title="포도주의 페놀 성분 – Korean" lang="ko" hreflang="ko" data-title="포도주의 페놀 성분" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%AF%E3%82%A4%E3%83%B3%E3%81%AE%E3%83%95%E3%82%A7%E3%83%8E%E3%83%BC%E3%83%AB" title="ワインのフェノール – Japanese" lang="ja" hreflang="ja" data-title="ワインのフェノール" 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/Conte%C3%BAdo_fen%C3%B3lico_do_vinho" title="Conteúdo fenólico do vinho – Portuguese" lang="pt" hreflang="pt" data-title="Conteúdo fenólico do vinho" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/%C3%9Cz%C3%BCmlerdeki_fenolik_bile%C5%9Fenler" title="Üzümlerdeki fenolik bileşenler – Turkish" lang="tr" hreflang="tr" data-title="Üzümlerdeki fenolik bileşenler" data-language-autonym="Türkçe" 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<div id="contentSub"><div id="mw-content-subtitle"><span class="mw-redirectedfrom">(Redirected from <a href="/w/index.php?title=Phenolic_compounds_in_wine&redirect=no" class="mw-redirect" title="Phenolic compounds in wine">Phenolic compounds in wine</a>)</span></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Wine chemistry</div> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Shiraz_Grapes.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/eb/Shiraz_Grapes.jpg/250px-Shiraz_Grapes.jpg" decoding="async" width="250" height="188" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/eb/Shiraz_Grapes.jpg/375px-Shiraz_Grapes.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/eb/Shiraz_Grapes.jpg/500px-Shiraz_Grapes.jpg 2x" data-file-width="2560" data-file-height="1920" /></a><figcaption>The phenolic compounds in grapes contribute to the taste, color and mouthfeel of wine. <a href="/wiki/Syrah" title="Syrah">Syrah</a> pictured here.</figcaption></figure> <p>Phenolic compounds—<a href="/wiki/Natural_phenol" class="mw-redirect" title="Natural phenol">natural phenol</a> and <a href="/wiki/Polyphenol" title="Polyphenol">polyphenols</a>—occur naturally in <a href="/wiki/Wine" title="Wine">wine</a>. These include a large group of several hundred <a href="/wiki/Chemical_compound" title="Chemical compound">chemical compounds</a> that affect the <a href="/wiki/Taste_(wine)" class="mw-redirect" title="Taste (wine)">taste</a>, <a href="/wiki/Color_(wine)" class="mw-redirect" title="Color (wine)">color</a> and <a href="/wiki/Mouthfeel_(wine)" class="mw-redirect" title="Mouthfeel (wine)">mouthfeel</a> of wine. These compounds include <a href="/wiki/Phenolic_acid" title="Phenolic acid">phenolic acids</a>, <a href="/wiki/Stilbenoid" title="Stilbenoid">stilbenoids</a>, <a href="/wiki/Flavonol" class="mw-redirect" title="Flavonol">flavonols</a>, <a href="/wiki/Dihydroflavonol" class="mw-redirect" title="Dihydroflavonol">dihydroflavonols</a>, <a href="/wiki/Anthocyanin" title="Anthocyanin">anthocyanins</a>, <a href="/wiki/Flavanol" class="mw-redirect" title="Flavanol">flavanol</a> monomers (<a href="/wiki/Catechin" title="Catechin">catechins</a>) and <a href="/wiki/Flavanol" class="mw-redirect" title="Flavanol">flavanol</a> polymers (<a href="/wiki/Proanthocyanidin" title="Proanthocyanidin">proanthocyanidins</a>). This large group of natural phenols can be broadly separated into two categories, <a href="/wiki/Flavonoid" title="Flavonoid">flavonoids</a> and non-flavonoids. Flavonoids include the <a href="/wiki/Anthocyanin" title="Anthocyanin">anthocyanins</a> and <a href="/wiki/Tannin" title="Tannin">tannins</a> which contribute to the color and mouthfeel of the wine.<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> The non-flavonoids include the <a href="/wiki/Stilbenoid" title="Stilbenoid">stilbenoids</a> such as <a href="/wiki/Resveratrol" title="Resveratrol">resveratrol</a> and <a href="/wiki/Phenolic_acid" title="Phenolic acid">phenolic acids</a> such as <a href="/wiki/Benzoic_(acid)" class="mw-redirect" title="Benzoic (acid)">benzoic</a>, <a href="/wiki/Caffeic_acid" title="Caffeic acid">caffeic</a> and <a href="/wiki/Cinnamic_acid" title="Cinnamic acid">cinnamic</a> acids. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Origin_of_the_phenolic_compounds">Origin of the phenolic compounds</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phenolic_content_in_wine&action=edit&section=1" title="Edit section: Origin of the phenolic compounds"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The natural phenols are not evenly distributed within the grape. Phenolic acids are largely present in the pulp, <a href="/wiki/Anthocyanin" title="Anthocyanin">anthocyanins</a> and <a href="/wiki/Stilbenoid" title="Stilbenoid">stilbenoids</a> in the skin, and other phenols (<a href="/wiki/Catechin" title="Catechin">catechins</a>, <a href="/wiki/Proanthocyanidin" title="Proanthocyanidin">proanthocyanidins</a> and <a href="/wiki/Flavonol" class="mw-redirect" title="Flavonol">flavonols</a>) in the skin and the seeds.<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> During the <a href="/wiki/Growth_cycle_of_the_grapevine" class="mw-redirect" title="Growth cycle of the grapevine">growth cycle of the grapevine</a>, sunlight will increase the concentration of phenolics in the grape berries, their development being an important component of <a href="/wiki/Canopy_management" class="mw-redirect" title="Canopy management">canopy management</a>. The proportion of the different phenols in any one wine will therefore vary according to the type of <a href="/wiki/Vinification" class="mw-redirect" title="Vinification">vinification</a>. <a href="/wiki/Red_wine" title="Red wine">Red wine</a> will be richer in phenols abundant in the skin and seeds, such as <a href="/wiki/Anthocyanin" title="Anthocyanin">anthocyanin</a>, <a href="/wiki/Proanthocyanidin" title="Proanthocyanidin">proanthocyanidins</a> and <a href="/wiki/Flavonol" class="mw-redirect" title="Flavonol">flavonols</a>, whereas the phenols in <a href="/wiki/White_wine" title="White wine">white wine</a> will essentially originate from the pulp, and these will be the phenolic acids together with lower amounts of <a href="/wiki/Catechin" title="Catechin">catechins</a> and <a href="/wiki/Stilbene" title="Stilbene">stilbenes</a>. Red wines will also have the phenols found in white wines. </p><p>Wine simple phenols are further transformed during <a href="/wiki/Aging_of_wine" title="Aging of wine">wine aging</a> into complex molecules formed notably by the condensation of proanthocyanidins and anthocyanins, which explains the modification in the color. Anthocyanins react with catechins, proanthocyanidins and other wine components during wine aging to form new polymeric pigments resulting in a modification of the wine color and a lower <a href="/wiki/Astringency" class="mw-redirect" title="Astringency">astringency</a>.<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><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> Average total polyphenol content measured by the <a href="/wiki/Folin-Ciocalteu_reagent" class="mw-redirect" title="Folin-Ciocalteu reagent">Folin</a> method is 216 mg/100 ml for red wine and 32 mg/100 ml for white wine. The content of phenols in rosé wine (82 mg/100 ml) is intermediate between that in red and white wines. </p><p>In <a href="/wiki/Winemaking" title="Winemaking">winemaking</a>, the process of <a href="/wiki/Maceration_(wine)" title="Maceration (wine)">maceration</a> or "skin contact" is used to increase the concentration of phenols in wine. Phenolic acids are found in the pulp or juice of the wine and can be commonly found in white wines which usually do not go through a maceration period. The process of <a href="/wiki/Oak_(wine)" title="Oak (wine)">oak aging</a> can also introduce phenolic compounds into wine, most notably <a href="/wiki/Vanillin" title="Vanillin">vanillin</a> which adds <a href="/wiki/Vanilla" title="Vanilla">vanilla</a> <a href="/wiki/Aroma_(wine)" class="mw-redirect" title="Aroma (wine)">aroma</a> to wines.<sup id="cite_ref-Oxford_pp_517-518_5-0" class="reference"><a href="#cite_note-Oxford_pp_517-518-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p><p>Most wine phenols are classified as <a href="/wiki/Secondary_metabolite" title="Secondary metabolite">secondary metabolites</a> and were not thought to be active in the primary <a href="/wiki/Metabolism" title="Metabolism">metabolism</a> and function of the grapevine. However, there is evidence that in some plants <a href="/wiki/Flavonoid" title="Flavonoid">flavonoids</a> play a role as endogenous regulators of <a href="/wiki/Auxin" title="Auxin">auxin</a> transport.<sup id="cite_ref-pmid11402184_6-0" class="reference"><a href="#cite_note-pmid11402184-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> They are <a href="/wiki/Water-soluble" class="mw-redirect" title="Water-soluble">water-soluble</a> and are usually secreted into the <a href="/wiki/Vacuole" title="Vacuole">vacuole</a> of the grapevine as <a href="/wiki/Glycosides" class="mw-redirect" title="Glycosides">glycosides</a>. </p> <div class="mw-heading mw-heading2"><h2 id="Grape_polyphenols">Grape polyphenols</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phenolic_content_in_wine&action=edit&section=2" title="Edit section: Grape polyphenols"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><i><a href="/wiki/Vitis_vinifera" title="Vitis vinifera">Vitis vinifera</a></i>, the common grape vine, from which European style wines are made the world over, produces many phenolic compounds. There is a varietal effect on the relative composition. </p> <div class="mw-heading mw-heading3"><h3 id="Flavonoids">Flavonoids</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phenolic_content_in_wine&action=edit&section=3" title="Edit section: Flavonoids"><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 article: <a href="/wiki/Flavonoids" class="mw-redirect" title="Flavonoids">Flavonoids</a></div> <figure class="mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:Red_wine_cap.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e1/Red_wine_cap.jpg/250px-Red_wine_cap.jpg" decoding="async" width="250" height="188" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e1/Red_wine_cap.jpg/375px-Red_wine_cap.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e1/Red_wine_cap.jpg/500px-Red_wine_cap.jpg 2x" data-file-width="800" data-file-height="600" /></a><figcaption>The process of <a href="/wiki/Maceration_(wine)" title="Maceration (wine)">maceration</a> or extended skin contact allows the extraction of phenolic compounds from the skins of the grape into the wine</figcaption></figure> <p>In red wine, up to 90% of the wine's phenolic content falls under the classification of <a href="/wiki/Flavonoid" title="Flavonoid">flavonoids</a>. These phenols, mainly derived from the stems, seeds and skins are often leached out of the grape during the maceration period of winemaking. The amount of phenols leached is known as <a href="/wiki/Extraction_(chemistry)" title="Extraction (chemistry)">extraction</a>. These compounds contribute to the <a href="/wiki/Astringency" class="mw-redirect" title="Astringency">astringency</a>, color and mouthfeel of the wine. In white wines the number of flavonoids is reduced due to the lesser contact with the skins that they receive during winemaking. There is on-going study into the <a href="/wiki/Health_benefits_of_wine" class="mw-redirect" title="Health benefits of wine">health benefits of wine</a> derived from the <a href="/wiki/Antioxidant" title="Antioxidant">antioxidant</a> and <a href="/wiki/Chemopreventive" class="mw-redirect" title="Chemopreventive">chemopreventive</a> properties of flavonoids.<sup id="cite_ref-Oxford_pp_273-274_7-0" class="reference"><a href="#cite_note-Oxford_pp_273-274-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Flavonols">Flavonols</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phenolic_content_in_wine&action=edit&section=4" title="Edit section: Flavonols"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Flavonols" title="Flavonols">Flavonols</a></div> <p>Within the flavonoid category is a subcategory known as <a href="/wiki/Flavonol" class="mw-redirect" title="Flavonol">flavonols</a>, which includes the yellow <a href="/wiki/Pigment" title="Pigment">pigment</a> - <a href="/wiki/Quercetin" title="Quercetin">quercetin</a>. Like other flavonoids, the concentration of flavonols in the grape berries increases as they are exposed to sunlight. Wine grapes facing too much sun exposure can see an accelerated ripening period, leading to a lessened ability for the synthesis of flavonols.<sup id="cite_ref-Gutiérrez-Gamboa_109946_8-0" class="reference"><a href="#cite_note-Gutiérrez-Gamboa_109946-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> Some <a href="/wiki/Viticulturalist" class="mw-redirect" title="Viticulturalist">viticulturalists</a> will use measurement of flavonols such as quercetin as an indication of a vineyard's sun exposure and the effectiveness of canopy management techniques. </p> <div class="mw-heading mw-heading4"><h4 id="Anthocyanins">Anthocyanins</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phenolic_content_in_wine&action=edit&section=5" title="Edit section: Anthocyanins"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Anthocyanin" title="Anthocyanin">Anthocyanin</a></div> <p>Anthocyanins are phenolic compounds found throughout the <a href="/wiki/Plant_kingdom" class="mw-redirect" title="Plant kingdom">plant kingdom</a>, being frequently responsible for the blue to red colors found in <a href="/wiki/Flower" title="Flower">flowers</a>, <a href="/wiki/Fruit" title="Fruit">fruits</a> and <a href="/wiki/Leaf" title="Leaf">leaves</a>. In wine grapes, they develop during the stage of <i><a href="/wiki/Veraison" title="Veraison">veraison</a>,</i> when the skin of red wine grapes changes color from green to red to black. As the <a href="/wiki/Sugar_in_wine" class="mw-redirect" title="Sugar in wine">sugars in the grape</a> increase during <a href="/wiki/Ripening_(wine)" class="mw-redirect" title="Ripening (wine)">ripening</a> so does the concentration of anthocyanins. An issue associated with climate change has been the accumulation of sugars within the grape accelerating rapidly and outpacing the accumulation of anthocyanins.<sup id="cite_ref-Gutiérrez-Gamboa_109946_8-1" class="reference"><a href="#cite_note-Gutiérrez-Gamboa_109946-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> This leaves viticulturists with the choice of harvesting grapes with too high sugar content or with too low anthocyanin content. In most grapes anthocyanins are found only in the outer cell layers of the skin, leaving the grape juice inside virtually colorless. Therefore, to get color pigmentation in the wine, the <a href="/wiki/Fermentation_(wine)" class="mw-redirect" title="Fermentation (wine)">fermenting</a> <a href="/wiki/Must" title="Must">must</a> needs to be in contact with the grape skins in order for the anthocyanins to be extracted. Hence, white wine can be made from red wine grapes in the same way that many white <a href="/wiki/Sparkling_wine" title="Sparkling wine">sparkling wines</a> are made from the red wine grapes of <a href="/wiki/Pinot_noir" title="Pinot noir">Pinot noir</a> and <a href="/wiki/Pinot_Meunier" title="Pinot Meunier">Pinot Meunier</a>. The exception to this is the small class of grapes known as <a href="/wiki/Teinturier" class="mw-redirect" title="Teinturier">teinturiers</a>, such as <a href="/wiki/Alicante_Bouschet" title="Alicante Bouschet">Alicante Bouschet</a>, which have a small amount of anthocyanins in the pulp that produces pigmented juice.<sup id="cite_ref-Oxford_p_24_9-0" class="reference"><a href="#cite_note-Oxford_p_24-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p><p>There are several types of anthocyanins (as the <a href="/wiki/Glycoside" title="Glycoside">glycoside</a>) found in wine grapes which are responsible for the vast range of coloring from ruby red through to dark black found in wine grapes. <a href="/wiki/Ampelographer" class="mw-redirect" title="Ampelographer">Ampelographers</a> can use this observation to assist in the identification of different <a href="/wiki/Grape_varieties" class="mw-redirect" title="Grape varieties">grape varieties</a>. The European vine family <i><a href="/wiki/Vitis_vinifera" title="Vitis vinifera">Vitis vinifera</a></i> is characterized by anthocyanins that are composed of only one molecule of <a href="/wiki/Glucose" title="Glucose">glucose</a> while non-<i>vinifera</i> vines such as <a href="/wiki/Hybrids_(grape)" class="mw-redirect" title="Hybrids (grape)">hybrids</a> and the American <i><a href="/wiki/Vitis_labrusca" title="Vitis labrusca">Vitis labrusca</a></i> will have anthocyanins with two molecules. This phenomenon is due to a double mutation in the <a href="/wiki/Anthocyanin_5-O-glucosyltransferase" title="Anthocyanin 5-O-glucosyltransferase">anthocyanin 5-O-glucosyltransferase</a> gene of <i>V. vinifera</i>.<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> In the mid-20th century, French ampelographers used this knowledge to test the various vine varieties throughout France to identify which vineyards still contained non-<i>vinifera</i> plantings.<sup id="cite_ref-Oxford_p_24_9-1" class="reference"><a href="#cite_note-Oxford_p_24-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p><p>Red-berried <a href="/wiki/Pinot_(grape)" title="Pinot (grape)">Pinot grape</a> varieties are also known to not synthesize <a href="/wiki/Para-coumaroylated_anthocyanin" class="mw-redirect" title="Para-coumaroylated anthocyanin">para-coumaroylated</a> or <a href="/w/index.php?title=Acetylated_anthocyanin&action=edit&redlink=1" class="new" title="Acetylated anthocyanin (page does not exist)">acetylated anthocyanins</a> as other varieties do.<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> <figure class="mw-default-size mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Tempranillowine.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a0/Tempranillowine.jpg/220px-Tempranillowine.jpg" decoding="async" width="220" height="158" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a0/Tempranillowine.jpg/330px-Tempranillowine.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a0/Tempranillowine.jpg/440px-Tempranillowine.jpg 2x" data-file-width="1364" data-file-height="980" /></a><figcaption><a href="/wiki/Tempranillo" title="Tempranillo">Tempranillo</a> wine has a high pH level which means that there is a higher concentration of blue and colorless <a href="/wiki/Anthocyanin" title="Anthocyanin">anthocyanin</a> pigments in the wine. The resulting wine's coloring will have more blue hues than bright ruby red hues.</figcaption></figure> <p>The color variation in the finished red wine is partly derived from the <a href="/wiki/Ionization" title="Ionization">ionization</a> of anthocyanin pigments caused by the <a href="/wiki/Acidity_(wine)" class="mw-redirect" title="Acidity (wine)">acidity</a> of the wine. In this case, the three types of anthocyanin pigments are red, blue and colorless with the concentration of those various pigments dictating the color of the wine. A wine with low <a href="/wiki/PH" title="PH">pH</a> (and such greater acidity) will have a higher occurrence of ionized anthocyanins which will increase the amount of bright red pigments. Wines with a higher pH will have a higher concentration of blue and colorless pigments. As the <a href="/wiki/Aging_of_wine" title="Aging of wine">wine ages</a>, anthocyanins will react with other acids and compounds in wines such as tannins, <a href="/wiki/Pyruvic_acid" title="Pyruvic acid">pyruvic acid</a> and <a href="/wiki/Acetaldehyde" title="Acetaldehyde">acetaldehyde</a> which will change the color of the wine, causing it to develop more "brick red" hues. These molecules will link up to create <a href="/wiki/Polymer" title="Polymer">polymers</a> that eventually exceed their <a href="/wiki/Solubility" title="Solubility">solubility</a> and become sediment at the bottom of wine bottles.<sup id="cite_ref-Oxford_p_24_9-2" class="reference"><a href="#cite_note-Oxford_p_24-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Pyranoanthocyanins" class="mw-redirect" title="Pyranoanthocyanins">Pyranoanthocyanins</a> are chemical compounds formed in red <a href="/wiki/Wine" title="Wine">wines</a> by <a href="/wiki/Yeast_(wine)" class="mw-redirect" title="Yeast (wine)">yeast</a> during <a href="/wiki/Fermentation_(wine)" class="mw-redirect" title="Fermentation (wine)">fermentation</a> processes<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> or during <a href="/wiki/Microoxygenation" title="Microoxygenation">controlled oxygenation</a> processes<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> during the <a href="/wiki/Aging_of_wine" title="Aging of wine">aging of wine</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> </p> <div class="mw-heading mw-heading4"><h4 id="Tannins">Tannins</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phenolic_content_in_wine&action=edit&section=6" title="Edit section: Tannins"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Tannin" title="Tannin">Tannin</a></div> <p>Tannins refer to the diverse group of chemical compounds in wine that can affect the color, aging ability and texture of the wine. While tannins cannot be smelled or tasted, they can be perceived during <a href="/wiki/Wine_tasting" title="Wine tasting">wine tasting</a> by the <a href="/wiki/Touch" class="mw-redirect" title="Touch">tactile</a> sensation of <a href="/wiki/Astringency" class="mw-redirect" title="Astringency">astringency</a> and sense of bitterness that they can leave in the mouth. This is due to the tendency of tannins to react with <a href="/wiki/Protein" title="Protein">proteins</a>, such as the ones found in <a href="/wiki/Saliva" title="Saliva">saliva</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> In <a href="/wiki/Food_and_wine_pairing" class="mw-redirect" title="Food and wine pairing">food and wine pairing</a>, foods that are high in proteins (such as <a href="/wiki/Red_meat" title="Red meat">red meat</a>) are often paired with tannic wines to minimize the astringency of tannins. However, many wine drinkers find the perception of tannins to be a positive trait—especially as it relates to mouthfeel. The management of tannins in the winemaking process is a key component in the resulting quality.<sup id="cite_ref-Oxford_p_680_16-0" class="reference"><a href="#cite_note-Oxford_p_680-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p><p>Tannins are found in the skin, stems, and seeds of wine grapes but can also be introduced to the wine through the use of oak barrels and chips or with the addition of tannin powder. The natural tannins found in grapes are known as <a href="/wiki/Proanthocyanidin" title="Proanthocyanidin">proanthocyanidins</a> due to their ability to release red anthocyanin pigments when they are heated in an acidic solution. Grape extracts are mainly rich in monomers and small oligomers (mean degree of polymerization < 8). Grape seed extracts contain three monomers (catechin, epicatechin and epicatechin gallate) and procyanidin oligomers. Grape skin extracts contain four monomers (catechin, epicatechin, gallocatechin and epigallocatechin), as well as <a href="/wiki/Procyanidin" title="Procyanidin">procyanidins</a> and <a href="/wiki/Prodelphinidin" title="Prodelphinidin">prodelphinidins</a> oligomers.<sup id="cite_ref-M2009_17-0" class="reference"><a href="#cite_note-M2009-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> The tannins are formed by <a href="/wiki/Enzymes" class="mw-redirect" title="Enzymes">enzymes</a> during metabolic processes of the grapevine. The amount of tannins found naturally in grapes varies depending on the variety with <a href="/wiki/Cabernet_Sauvignon" title="Cabernet Sauvignon">Cabernet Sauvignon</a>, <a href="/wiki/Nebbiolo" title="Nebbiolo">Nebbiolo</a>, <a href="/wiki/Syrah" title="Syrah">Syrah</a> and <a href="/wiki/Tannat" title="Tannat">Tannat</a> being 4 of the most tannic grape varieties. The reaction of tannins and anthocyanins with the phenolic compound <a href="/wiki/Catechin" title="Catechin">catechins</a> creates another class of tannins known as <b>pigmented tannins</b> which influence the color of red wine.<sup id="cite_ref-cat.inist.fr_18-0" class="reference"><a href="#cite_note-cat.inist.fr-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> Commercial preparations of tannins, known as <i>enological tannins</i>, made from <a href="/wiki/Oak_wood" class="mw-redirect" title="Oak wood">oak wood</a>, <a href="/wiki/Grape" title="Grape">grape</a> seed and skin, plant <a href="/wiki/Gall" title="Gall">gall</a>, <a href="/wiki/Chestnut" title="Chestnut">chestnut</a>, <a href="/wiki/Quebracho_tannin" class="mw-redirect" title="Quebracho tannin">quebracho</a>, <a href="/wiki/Uncaria_gambir" title="Uncaria gambir">gambier</a><sup id="cite_ref-Luz_Sanz_M._2008,_pp._778-783_19-0" class="reference"><a href="#cite_note-Luz_Sanz_M._2008,_pp._778-783-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> and <a href="/wiki/Myrobalan" title="Myrobalan">myrobalan</a> fruits,<sup id="cite_ref-ajevonline.org_20-0" class="reference"><a href="#cite_note-ajevonline.org-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> can be added at different stages of the wine production to improve color durability. The tannins derived from oak influence are known as "hydrolysable tannins" being created from the <a href="/wiki/Ellagic_(acid)" class="mw-redirect" title="Ellagic (acid)">ellagic</a> and <a href="/wiki/Gallic_acid" title="Gallic acid">gallic acid</a> found in the wood.<sup id="cite_ref-Oxford_p_680_16-1" class="reference"><a href="#cite_note-Oxford_p_680-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:Mthomebrew_maceration.JPG" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/01/Mthomebrew_maceration.JPG/250px-Mthomebrew_maceration.JPG" decoding="async" width="250" height="77" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/01/Mthomebrew_maceration.JPG/375px-Mthomebrew_maceration.JPG 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/01/Mthomebrew_maceration.JPG/500px-Mthomebrew_maceration.JPG 2x" data-file-width="1202" data-file-height="372" /></a><figcaption>Fermenting with the stem, seeds and skin will increase the <a href="/wiki/Tannin" title="Tannin">tannin</a> content of the wine</figcaption></figure> <p>In the vineyards, there is also a growing distinction being made between "ripe" and "unripe" tannins present in the grape. This "<a href="/wiki/Physiological_ripeness" class="mw-redirect" title="Physiological ripeness">physiological ripeness</a>", which is roughly determined by tasting the grapes off the vines, is being used along with sugar levels as a determination of when to <a href="/wiki/Harvest_(wine)" title="Harvest (wine)">harvest</a>. The idea is that "riper" tannins will taste softer but still impart some of the texture components found favorable in wine. In winemaking, the amount of the time that the must spends in contact with the grape skins, stems and seeds will influence the amount of tannins that are present in the wine with wines subjected to longer maceration period having more tannin extract. Following harvest, stems are normally picked out and discarded prior to fermentation but some winemakers may intentionally leave in a few stems for varieties low in tannins (like Pinot noir) in order to increase the tannic extract in the wine. If there is an excess in the amount of tannins in the wine, winemakers can use various <a href="/wiki/Fining_(wine)" class="mw-redirect" title="Fining (wine)">fining</a> agents like <a href="/wiki/Albumin" title="Albumin">albumin</a>, <a href="/wiki/Casein" title="Casein">casein</a> and <a href="/wiki/Gelatin" title="Gelatin">gelatin</a> that can bind to tannins molecule and <a href="/wiki/Precipitate" class="mw-redirect" title="Precipitate">precipitate</a> them out as sediments. As a wine ages, tannins will form long polymerized chains which come across to a taster as "softer" and less tannic. This process can be accelerated by exposing the wine to <a href="/wiki/Oxygen" title="Oxygen">oxygen</a>, which oxidize tannins to quinone-like compounds that are polymerization-prone. The winemaking technique of <a href="/wiki/Micro-oxygenation" class="mw-redirect" title="Micro-oxygenation">micro-oxygenation</a> and <a href="/wiki/Decanting_wine" class="mw-redirect" title="Decanting wine">decanting wine</a> use oxygen to partially mimic the effect of aging on tannins.<sup id="cite_ref-Oxford_p_680_16-2" class="reference"><a href="#cite_note-Oxford_p_680-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p><p>A study in wine production and consumption has shown that tannins, in the form of <a href="/wiki/Proanthocyanidin" title="Proanthocyanidin">proanthocyanidins</a>, have a beneficial effect on vascular health. The study showed that tannins suppressed production of the peptide responsible for hardening arteries. To support their findings, the study also points out that wines from the regions of southwest France and Sardinia are particularly rich in proanthocyanidins, and that these regions also produce populations with longer life spans.<sup id="cite_ref-21" class="reference"><a href="#cite_note-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> </p><p>Reactions of tannins with the phenolic compound <a href="/wiki/Anthocyanidin" title="Anthocyanidin">anthocyanidins</a> creates another class of tannins known as <i>pigmented tannins</i> which influences the color of red wine.<sup id="cite_ref-cat.inist.fr_18-1" class="reference"><a href="#cite_note-cat.inist.fr-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading5"><h5 id="Addition_of_enological_tannins">Addition of enological tannins</h5><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phenolic_content_in_wine&action=edit&section=7" title="Edit section: Addition of enological tannins"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Commercial preparations of tannins, known as <i>enological tannins</i>, made from <a href="/wiki/Oak_wood" class="mw-redirect" title="Oak wood">oak wood</a>, <a href="/wiki/Grape" title="Grape">grape</a> seed and skin, plant <a href="/wiki/Gall" title="Gall">gall</a>, <a href="/wiki/Chestnut" title="Chestnut">chestnut</a>, <a href="/wiki/Quebracho_tannin" class="mw-redirect" title="Quebracho tannin">quebracho</a>, <a href="/wiki/Uncaria_gambir" title="Uncaria gambir">gambier</a><sup id="cite_ref-Luz_Sanz_M._2008,_pp._778-783_19-1" class="reference"><a href="#cite_note-Luz_Sanz_M._2008,_pp._778-783-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> and <a href="/wiki/Myrobalan" title="Myrobalan">myrobalan</a> fruits,<sup id="cite_ref-ajevonline.org_20-1" class="reference"><a href="#cite_note-ajevonline.org-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> can be added at different stages of the wine production to improve color durability. </p> <div class="mw-heading mw-heading5"><h5 id="Effects_of_tannins_on_the_drinkability_and_aging_potential_of_wine">Effects of tannins on the drinkability and aging potential of wine</h5><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phenolic_content_in_wine&action=edit&section=8" title="Edit section: Effects of tannins on the drinkability and aging potential of wine"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Tannins are a natural preservative in wine. Un-aged wines with high tannin content can be less palatable than wines with a lower level of tannins. Tannins can be described as leaving a dry and puckered feeling with a "furriness" in the mouth that can be compared to a stewed tea, which is also very tannic. This effect is particularly profound when drinking tannic wines without the benefit of food. </p><p>Many <a href="/wiki/Oenophile" class="mw-redirect" title="Oenophile">wine lovers</a> see natural tannins (found particularly in varietals such as <a href="/wiki/Cabernet_Sauvignon" title="Cabernet Sauvignon">Cabernet Sauvignon</a> and often accentuated by heavy <a href="/wiki/Oak" title="Oak">oak</a> barrel aging) as a sign of potential longevity and <a href="/wiki/Ageability_(wine)" class="mw-redirect" title="Ageability (wine)">ageability</a>. Tannins impart a mouth-puckering astringency when the wine is young but "resolve" (through a chemical process called <a href="/wiki/Polymerization" title="Polymerization">polymerization</a>) into delicious and complex elements of "bottle <a href="/wiki/Bouquet_(wine)" class="mw-redirect" title="Bouquet (wine)">bouquet</a>" when the wine is cellared under appropriate temperature conditions, preferably in the range of a constant 55 to 60 °F (13 to 16 °C).<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> Such wines mellow and improve with age with the tannic "backbone" helping the wine survive for as long as 40 years or more.<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> In many regions (such as in <a href="/wiki/Bordeaux" title="Bordeaux">Bordeaux</a>), tannic grapes such as <a href="/wiki/Cabernet_Sauvignon" title="Cabernet Sauvignon">Cabernet Sauvignon</a> are blended with lower-tannin grapes such as <a href="/wiki/Merlot" title="Merlot">Merlot</a> or <a href="/wiki/Cabernet_Franc" title="Cabernet Franc">Cabernet Franc</a>, diluting the tannic characteristics. White wines and wines that are vinified to be drunk young (for examples, see <a href="/wiki/Nouveau_wine" class="mw-redirect" title="Nouveau wine">nouveau wines</a>) typically have lower tannin levels. </p> <div class="mw-heading mw-heading3"><h3 id="Other_flavonoids">Other flavonoids</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phenolic_content_in_wine&action=edit&section=9" title="Edit section: Other flavonoids"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Flavan-3-ol" title="Flavan-3-ol">Flavan-3-ols</a> (catechins) are flavonoids that contribute to the construction of various tannins and contribute to the perception of bitterness in wine. They are found in highest concentrations in grape seeds but are also in the skin and stems. Catechins play a role in the <a href="/wiki/Microbial" class="mw-redirect" title="Microbial">microbial</a> defense of the grape berry, being produced in higher concentrations by the grape vines when it is being attacked by <a href="/wiki/Grape_disease" class="mw-redirect" title="Grape disease">grape diseases</a> such as <a href="/wiki/Downy_mildew" title="Downy mildew">downy mildew</a>. Because of that grape vines in cool, damp climates produce catechins at high levels than vines in dry, hot climates. Together with anthocyanins and tannins they increase the stability of a wines color-meaning that a wine will be able to maintain its coloring for a longer period of time. The amount of catechins present varies among grape varieties with varietals like Pinot noir having high concentrations while <a href="/wiki/Merlot" title="Merlot">Merlot</a> and especially Syrah have very low levels.<sup id="cite_ref-M2009_17-1" class="reference"><a href="#cite_note-M2009-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> As an antioxidant, there are some studies into the health benefits of moderate consumption of wines high in catechins.<sup id="cite_ref-Oxford_p_144_24-0" class="reference"><a href="#cite_note-Oxford_p_144-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> </p><p>In red grapes, the main flavonol is on average <a href="/wiki/Quercetin" title="Quercetin">quercetin</a>, followed by <a href="/wiki/Myricetin" title="Myricetin">myricetin</a>, <a href="/wiki/Kaempferol" title="Kaempferol">kaempferol</a>, <a href="/wiki/Laricitrin" title="Laricitrin">laricitrin</a>, <a href="/wiki/Isorhamnetin" title="Isorhamnetin">isorhamnetin</a>, and <a href="/wiki/Syringetin" title="Syringetin">syringetin</a>.<sup id="cite_ref-M2006_25-0" class="reference"><a href="#cite_note-M2006-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> In white grapes, the main flavonol is quercetin, followed by kaempferol and isorhamnetin. The delphinidin-like flavonols myricetin, laricitrin, and syringetin are missing in all white varieties, indicating that the enzyme flavonoid 3',5'-hydroxylase is not expressed in white grape varieties.<sup id="cite_ref-M2006_25-1" class="reference"><a href="#cite_note-M2006-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> </p><p><a href="/wiki/Myricetin" title="Myricetin">Myricetin</a>, <a href="/wiki/Laricitrin" title="Laricitrin">laricitrin</a><sup id="cite_ref-26" class="reference"><a href="#cite_note-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> and <a href="/wiki/Syringetin" title="Syringetin">syringetin</a>,<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> flavonols which are present in red grape varieties only, can be found in red wine.<sup id="cite_ref-act_28-0" class="reference"><a href="#cite_note-act-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Non-flavonoids">Non-flavonoids</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phenolic_content_in_wine&action=edit&section=10" title="Edit section: Non-flavonoids"><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/Wine_and_health" class="mw-redirect" title="Wine and health">Wine and health</a></div> <div class="mw-heading mw-heading4"><h4 id="Hydroxycinnamic_acids">Hydroxycinnamic acids</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phenolic_content_in_wine&action=edit&section=11" title="Edit section: Hydroxycinnamic acids"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Hydroxycinnamic_acid" title="Hydroxycinnamic acid">Hydroxycinnamic acids</a> are the most important group of nonflavonoid phenols in wine. The four most abundant ones are the <a href="/wiki/Tartaric_acid" title="Tartaric acid">tartaric acid</a> esters <a href="/wiki/Caftaric_acid" title="Caftaric acid"><i>trans</i>-caftaric</a>, <i>cis</i>- and <i>trans</i>-<a href="/wiki/Coutaric_acid" title="Coutaric acid">coutaric</a>, and <i>trans</i>-<a href="/wiki/Fertaric_acid" title="Fertaric acid">fertaric acids</a>. In wine they are present also in the free form (<i>trans</i>-<a href="/wiki/Caffeic_acid" title="Caffeic acid">caffeic</a>, <i>trans</i>-<a href="/wiki/P-coumaric_acid" class="mw-redirect" title="P-coumaric acid">p-coumaric</a>, and <i>trans</i>-<a href="/wiki/Ferulic_acid" title="Ferulic acid">ferulic acids</a>).<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-heading4"><h4 id="Stilbenoids">Stilbenoids</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phenolic_content_in_wine&action=edit&section=12" title="Edit section: Stilbenoids"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><i>V. vinifera</i> also produces <a href="/wiki/Stilbenoid" title="Stilbenoid">stilbenoids</a>. </p><p><a href="/wiki/Resveratrol" title="Resveratrol">Resveratrol</a> is found in highest concentration in the skins of wine grapes. The accumulation in ripe berries of different concentrations of both bound and free resveratrols depends on the maturity level and is highly variable according to the genotype.<sup id="cite_ref-30" class="reference"><a href="#cite_note-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> Both red and white wine grape varieties contain resveratrol, but more frequent skin contact and maceration leads to red wines normally having ten times more resveratrol than white wines.<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> Resveratrol produced by grape vines provides defense against microbes, and production can be further artificially stimulated by <a href="/wiki/Ultraviolet_radiation" class="mw-redirect" title="Ultraviolet radiation">ultraviolet radiation</a>. Grapevines in cool, damp regions with higher risk of grape diseases, such as <a href="/wiki/Bordeaux_(wine)" class="mw-redirect" title="Bordeaux (wine)">Bordeaux</a> and <a href="/wiki/Burgundy_(wine)" class="mw-redirect" title="Burgundy (wine)">Burgundy</a>, tend to produce grapes with higher levels of resveratrol than warmer, drier wine regions such as <a href="/wiki/California_(wine)" class="mw-redirect" title="California (wine)">California</a> and <a href="/wiki/Australia_(wine)" class="mw-redirect" title="Australia (wine)">Australia</a>. Different grape varieties tend to have differing levels, with <a href="/wiki/Muscadine" class="mw-redirect" title="Muscadine">Muscadines</a> and the Pinot family having high levels while the <a href="/wiki/Cabernet_Sauvignon" title="Cabernet Sauvignon">Cabernet</a> family has lower levels of resveratrol. In the late 20th century interest in the possible health benefits of resveratrol in wine was spurred by discussion of the <a href="/wiki/French_paradox" title="French paradox">French paradox</a> involving the health of wine drinkers in France.<sup id="cite_ref-Oxford_p_569_32-0" class="reference"><a href="#cite_note-Oxford_p_569-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> </p><p><a href="/wiki/Piceatannol" title="Piceatannol">Piceatannol</a> is also present in grape <sup id="cite_ref-B2002_33-0" class="reference"><a href="#cite_note-B2002-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> from where it can be extracted and found in red wine.<sup id="cite_ref-act_28-1" class="reference"><a href="#cite_note-act-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Phenolic_acids">Phenolic acids</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phenolic_content_in_wine&action=edit&section=13" title="Edit section: Phenolic acids"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Vanillin" title="Vanillin">Vanillin</a> is a phenolic <a href="/wiki/Aldehyde" title="Aldehyde">aldehyde</a> most commonly associated with the vanilla notes in wines that have been aged in oak. Trace amounts of vanillin are found naturally in grapes, but they are most prominent in the <a href="/wiki/Lignin" title="Lignin">lignin</a> structure of oak barrels. Newer barrels will impart more vanillin, with the concentration present decreasing with each subsequent usage.<sup id="cite_ref-Oxford_p_727_34-0" class="reference"><a href="#cite_note-Oxford_p_727-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Phenols_from_oak_ageing">Phenols from oak ageing</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phenolic_content_in_wine&action=edit&section=14" title="Edit section: Phenols from oak ageing"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:WineBarrels_2005_SeanMcClean.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/af/WineBarrels_2005_SeanMcClean.jpg/250px-WineBarrels_2005_SeanMcClean.jpg" decoding="async" width="250" height="184" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/af/WineBarrels_2005_SeanMcClean.jpg/375px-WineBarrels_2005_SeanMcClean.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/af/WineBarrels_2005_SeanMcClean.jpg/500px-WineBarrels_2005_SeanMcClean.jpg 2x" data-file-width="720" data-file-height="529" /></a><figcaption>Phenolic compounds like tannins and <a href="/wiki/Vanillin" title="Vanillin">vanillin</a> can be extracted from aging in <a href="/wiki/Oak_(wine)" title="Oak (wine)">oak wine barrels</a></figcaption></figure> <p>Oak barrel will add compounds such as <a href="/wiki/Vanillin" title="Vanillin">vanillin</a> and hydrolysable tannins (<a href="/wiki/Ellagitannin" title="Ellagitannin">ellagitannins</a>). The <a href="/wiki/Hydrolyzable_tannin" class="mw-redirect" title="Hydrolyzable tannin">hydrolyzable tannins</a> present in oak are derived from <a href="/wiki/Lignin" title="Lignin">lignin</a> structures in the wood. They help protect the wine from oxidation and <a href="/wiki/Redox" title="Redox">reduction</a>.<sup id="cite_ref-Oxford_p_492_35-0" class="reference"><a href="#cite_note-Oxford_p_492-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> </p><p><a href="/wiki/4-Ethylphenol" title="4-Ethylphenol">4-Ethylphenol</a> and <a href="/wiki/4-ethylguaiacol" class="mw-redirect" title="4-ethylguaiacol">4-ethylguaiacol</a> are produced during ageing of red wine in oak barrels that are infected by <a href="/wiki/Brettanomyces" title="Brettanomyces">brettanomyces</a> .<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> <div class="mw-heading mw-heading2"><h2 id="Natural_phenols_and_polyphenols_from_cork_stoppers">Natural phenols and polyphenols from cork stoppers</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phenolic_content_in_wine&action=edit&section=15" title="Edit section: Natural phenols and polyphenols from cork stoppers"><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:EmbotelladoDeOrigen.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/af/EmbotelladoDeOrigen.jpg/220px-EmbotelladoDeOrigen.jpg" decoding="async" width="220" height="136" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/af/EmbotelladoDeOrigen.jpg/330px-EmbotelladoDeOrigen.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/af/EmbotelladoDeOrigen.jpg/440px-EmbotelladoDeOrigen.jpg 2x" data-file-width="1200" data-file-height="740" /></a><figcaption>Extracted cork inscribed with "Bottled at origin" in Spanish</figcaption></figure> <p>Low molecular weight polyphenols, as well as ellagitannins, are susceptible to be extracted from <a href="/wiki/Cork_(material)" title="Cork (material)">cork stoppers</a> into the wine.<sup id="cite_ref-37" class="reference"><a href="#cite_note-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup> The identified polyphenols are gallic, <a href="/wiki/Protocatechuic_acid" title="Protocatechuic acid">protocatechuic</a>, <a href="/wiki/Vanillic_acid" title="Vanillic acid">vanillic</a>, caffeic, <a href="/wiki/Ferulic_acid" title="Ferulic acid">ferulic</a>, and ellagic acids; <a href="/wiki/Protocatechuic_aldehyde" title="Protocatechuic aldehyde">protocatechuic</a>, <a href="/wiki/Vanillic_acid" title="Vanillic acid">vanillic</a>, <a href="/wiki/Coniferyl_aldehyde" title="Coniferyl aldehyde">coniferyl</a>, and <a href="/wiki/Sinapic_aldehyde" class="mw-redirect" title="Sinapic aldehyde">sinapic</a> aldehydes; the coumarins <a href="/wiki/Aesculetin" title="Aesculetin">aesculetin</a> and <a href="/wiki/Scopoletin" title="Scopoletin">scopoletin</a>; the ellagitannins are roburins <a href="/wiki/Roburin_A" title="Roburin A">A</a> and <a href="/w/index.php?title=Roburin_E&action=edit&redlink=1" class="new" title="Roburin E (page does not exist)">E</a>, <a href="/wiki/Grandinin" title="Grandinin">grandinin</a>, <a href="/wiki/Vescalagin" class="mw-redirect" title="Vescalagin">vescalagin</a> and <a href="/wiki/Castalagin" title="Castalagin">castalagin</a>.<sup id="cite_ref-38" class="reference"><a href="#cite_note-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup> </p><p><a href="/wiki/Guaiacol" title="Guaiacol">Guaiacol</a> is one of the molecules responsible for the <a href="/wiki/Cork_taint" title="Cork taint">cork taint</a> wine fault.<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> </p> <div class="mw-heading mw-heading2"><h2 id="Phenolic_content_in_relation_with_wine_making_techniques">Phenolic content in relation with wine making techniques</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phenolic_content_in_wine&action=edit&section=16" title="Edit section: Phenolic content in relation with wine making techniques"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Extraction_levels_in_relation_with_grape_pressing_techniques">Extraction levels in relation with grape pressing techniques</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phenolic_content_in_wine&action=edit&section=17" title="Edit section: Extraction levels in relation with grape pressing techniques"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Flash_release_(oenology)" class="mw-redirect" title="Flash release (oenology)">Flash release</a> is a technique used in wine <a href="/wiki/Pressing_(wine)" title="Pressing (wine)">pressing</a>.<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> The technique allows for a better extraction of phenolic compounds.<sup id="cite_ref-41" class="reference"><a href="#cite_note-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Microoxygeneation">Microoxygeneation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phenolic_content_in_wine&action=edit&section=18" title="Edit section: Microoxygeneation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The exposure of wine to <a href="/wiki/Microoxygenation" title="Microoxygenation">oxygen in limited quantities</a> affects phenolic content.<sup id="cite_ref-42" class="reference"><a href="#cite_note-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Phenolic_compounds_found_in_wine">Phenolic compounds found in wine</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phenolic_content_in_wine&action=edit&section=19" title="Edit section: Phenolic compounds found in wine"><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:Comp_LC_pinot_vs_rose_vs_white_wine_280_nm.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/7a/Comp_LC_pinot_vs_rose_vs_white_wine_280_nm.png/220px-Comp_LC_pinot_vs_rose_vs_white_wine_280_nm.png" decoding="async" width="220" height="123" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/7a/Comp_LC_pinot_vs_rose_vs_white_wine_280_nm.png/330px-Comp_LC_pinot_vs_rose_vs_white_wine_280_nm.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/7a/Comp_LC_pinot_vs_rose_vs_white_wine_280_nm.png/440px-Comp_LC_pinot_vs_rose_vs_white_wine_280_nm.png 2x" data-file-width="1226" data-file-height="688" /></a><figcaption>LC chromatograms at 280 nm of a <a href="/wiki/Pinot_(grape)" title="Pinot (grape)">pinot</a> <a href="/wiki/Red_wine" title="Red wine">red wine</a> (top), a <a href="/wiki/Beaujolais" title="Beaujolais">Beaujolais</a> <a href="/wiki/Ros%C3%A9" title="Rosé">rosé</a> (middle) and a <a href="/wiki/White_wine" title="White wine">white wine</a> (bottom). The picture shows peaks corresponding to the different phenolic compounds. The hump between 9 and 15 minutes corresponds to the presence of <a href="/wiki/Tannin" title="Tannin">tannins</a>, mostly present in the red wine.</figcaption></figure> <p>Depending on the methods of production, wine type, grape varieties, ageing processes, the following phenolics can be found in wine. The list, sorted in alphabetical order of common names, is not exhaustive. </p> <ul><li><a href="/wiki/Acutissimin_A" title="Acutissimin A">Acutissimin A</a></li> <li><a href="/wiki/Aesculetin" title="Aesculetin">aesculetin</a></li> <li><a href="/w/index.php?title=Anthocyanidin-caftaric_acid_adduct&action=edit&redlink=1" class="new" title="Anthocyanidin-caftaric acid adduct (page does not exist)">Anthocyanidin-caftaric acid adducts</a><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><sup id="cite_ref-44" class="reference"><a href="#cite_note-44"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup></li> <li><a href="/wiki/Astilbin" title="Astilbin">Astilbin</a></li> <li><a href="/wiki/Astringin" title="Astringin">Astringin</a></li> <li><a href="/wiki/B_type_proanthocyanidin_dimer" class="mw-redirect" title="B type proanthocyanidin dimer">B type proanthocyanidin dimers</a></li> <li><a href="/wiki/B_type_proanthocyanidin_trimer" class="mw-redirect" title="B type proanthocyanidin trimer">B type proanthocyanidin trimers</a></li> <li><a href="/wiki/Caffeic_acid" title="Caffeic acid">Caffeic acid</a></li> <li><a href="/wiki/Caftaric_acid" title="Caftaric acid">Caftaric acid</a></li> <li><a href="/wiki/Castalagin" title="Castalagin">Castalagin</a></li> <li><a href="/w/index.php?title=Castavinol_C1&action=edit&redlink=1" class="new" title="Castavinol C1 (page does not exist)">Castavinol C1</a></li> <li><a href="/w/index.php?title=Castavinol_C2&action=edit&redlink=1" class="new" title="Castavinol C2 (page does not exist)">Castavinol C2</a></li> <li><a href="/wiki/Castavinol_C3" title="Castavinol C3">Castavinol C3</a></li> <li><a href="/w/index.php?title=Castavinol_C4&action=edit&redlink=1" class="new" title="Castavinol C4 (page does not exist)">Castavinol C4</a></li> <li><a href="/wiki/Catechin" title="Catechin">Catechin</a><sup id="cite_ref-:0_45-0" class="reference"><a href="#cite_note-:0-45"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup></li> <li><a href="/w/index.php?title=Catechin-(4,8)-malvidin-3-O-glucoside&action=edit&redlink=1" class="new" title="Catechin-(4,8)-malvidin-3-O-glucoside (page does not exist)">Catechin-(4,8)-malvidin-3-O-glucoside</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></li> <li><a href="/wiki/Compound_NJ2" title="Compound NJ2">Compound NJ2</a></li> <li><a href="/wiki/Coniferyl_aldehyde" title="Coniferyl aldehyde">Coniferyl aldehyde</a></li> <li><a href="/wiki/Coumaric_acid" title="Coumaric acid">Coumaric acid</a><sup id="cite_ref-:0_45-1" class="reference"><a href="#cite_note-:0-45"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup></li> <li><a href="/wiki/Coutaric_acid" title="Coutaric acid">Coutaric acid</a></li> <li><a href="/wiki/Cyanidin" title="Cyanidin">Cyanidin</a></li> <li><a href="/wiki/Cyanin_(anthocyanin)" class="mw-redirect" title="Cyanin (anthocyanin)">Cyanin</a> (Cyanidin-3,5-O-diglucoside)</li> <li><a href="/wiki/Cyanidin_3O-glucoside" class="mw-redirect" title="Cyanidin 3O-glucoside">Cyanidin 3O-glucoside</a></li> <li><a href="/w/index.php?title=Cyanidin_acetyl_3O_glucoside&action=edit&redlink=1" class="new" title="Cyanidin acetyl 3O glucoside (page does not exist)">Cyanidin acetyl 3O glucoside</a></li> <li><a href="/w/index.php?title=Cyanidin_coumaroyl_3O_glucoside&action=edit&redlink=1" class="new" title="Cyanidin coumaroyl 3O glucoside (page does not exist)">Cyanidin coumaroyl 3O glucoside</a></li> <li><a href="/w/index.php?title=Cyanidin-3-O-glucoside-pyruvic_acid&action=edit&redlink=1" class="new" title="Cyanidin-3-O-glucoside-pyruvic acid (page does not exist)">Cyanidin-3-O-glucoside-pyruvic acid</a></li> <li><a href="/w/index.php?title=Cyanidin-3-O-acetylglucoside-pyruvic_acid&action=edit&redlink=1" class="new" title="Cyanidin-3-O-acetylglucoside-pyruvic acid (page does not exist)">Cyanidin-3-O-acetylglucoside-pyruvic acid</a></li> <li><a href="/w/index.php?title=Cyanidin-coumaroylglucoside-pyruvic_acid&action=edit&redlink=1" class="new" title="Cyanidin-coumaroylglucoside-pyruvic acid (page does not exist)">Cyanidin-coumaroylglucoside-pyruvic acid</a></li> <li><a href="/wiki/Delphinidin" title="Delphinidin">Delphinidin</a></li> <li><a href="/wiki/Delphinidin_3O_glucoside" class="mw-redirect" title="Delphinidin 3O glucoside">Delphinidin 3O glucoside</a></li> <li><a href="/w/index.php?title=Delphinidin_acetyl-3O_glucoside&action=edit&redlink=1" class="new" title="Delphinidin acetyl-3O glucoside (page does not exist)">Delphinidin acetyl-3O glucoside</a></li> <li><a href="/wiki/Delphinidin_coumaroyl_3O_glucoside" class="mw-redirect" title="Delphinidin coumaroyl 3O glucoside">Delphinidin coumaroyl 3O glucoside</a></li> <li><a href="/w/index.php?title=Delphinidin-3-O-glucoside-pyruvic_acid&action=edit&redlink=1" class="new" title="Delphinidin-3-O-glucoside-pyruvic acid (page does not exist)">Delphinidin-3-O-glucoside-pyruvic acid</a></li> <li><a href="/w/index.php?title=Delphinidin-3-O-acetylglucoside-pyruvic_acid&action=edit&redlink=1" class="new" title="Delphinidin-3-O-acetylglucoside-pyruvic acid (page does not exist)">Delphinidin-3-O-acetylglucoside-pyruvic acid</a></li> <li><a href="/w/index.php?title=Delphinidin-3-O-coumaroylglucoside-pyruvic_acid&action=edit&redlink=1" class="new" title="Delphinidin-3-O-coumaroylglucoside-pyruvic acid (page does not exist)">Delphinidin-3-O-coumaroylglucoside-pyruvic acid</a></li> <li><a href="/w/index.php?title=Delphinidin-3-O-glucoside-4-vinylcatechol&action=edit&redlink=1" class="new" title="Delphinidin-3-O-glucoside-4-vinylcatechol (page does not exist)">Delphinidin-3-O-glucoside-4-vinylcatechol</a></li> <li><a href="/w/index.php?title=Delphinidin-3-O-acetylglucoside-4-vinylcatechol&action=edit&redlink=1" class="new" title="Delphinidin-3-O-acetylglucoside-4-vinylcatechol (page does not exist)">Delphinidin-3-O-acetylglucoside-4-vinylcatechol</a></li> <li><a href="/w/index.php?title=Delphinidin-3-O-coumaroylglucoside-4-vinylcatechol&action=edit&redlink=1" class="new" title="Delphinidin-3-O-coumaroylglucoside-4-vinylcatechol (page does not exist)">Delphinidin-3-O-coumaroylglucoside-4-vinylcatechol</a></li> <li><a href="/w/index.php?title=Delphinidin-3-O-glucoside-4-vinylphenol&action=edit&redlink=1" class="new" title="Delphinidin-3-O-glucoside-4-vinylphenol (page does not exist)">Delphinidin-3-O-glucoside-4-vinylphenol</a></li> <li><a href="/w/index.php?title=Delphinidin-3-O-acetylglucoside-4-vinylphenol&action=edit&redlink=1" class="new" title="Delphinidin-3-O-acetylglucoside-4-vinylphenol (page does not exist)">Delphinidin-3-O-acetylglucoside-4-vinylphenol</a></li> <li><a href="/w/index.php?title=Delphinidin-3-O-coumaroylglucoside-4-vinylphenol&action=edit&redlink=1" class="new" title="Delphinidin-3-O-coumaroylglucoside-4-vinylphenol (page does not exist)">Delphinidin-3-O-coumaroylglucoside-4-vinylphenol</a></li> <li><a href="/w/index.php?title=Delphinidin-3-O-glucoside-4-vinylguaiacol&action=edit&redlink=1" class="new" title="Delphinidin-3-O-glucoside-4-vinylguaiacol (page does not exist)">Delphinidin-3-O-glucoside-4-vinylguaiacol</a></li> <li><a href="/w/index.php?title=Delphinidin-3-O-glucoside-4-vinyl(epi)catechin&action=edit&redlink=1" class="new" title="Delphinidin-3-O-glucoside-4-vinyl(epi)catechin (page does not exist)">Delphinidin-3-O-glucoside-4-vinyl(epi)catechin</a></li> <li><a href="/w/index.php?title=Delphinidin-3-O-acetylglucoside-4-vinyl(epi)catechin&action=edit&redlink=1" class="new" title="Delphinidin-3-O-acetylglucoside-4-vinyl(epi)catechin (page does not exist)">Delphinidin-3-O-acetylglucoside-4-vinyl(epi)catechin</a></li> <li><a href="/wiki/Delta-viniferin" class="mw-redirect" title="Delta-viniferin">Delta-viniferin</a></li> <li><a href="/wiki/Dihydro-resveratrol" title="Dihydro-resveratrol">Dihydro-resveratrol</a><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></li> <li><a href="/wiki/Ellagic_acid" title="Ellagic acid">Ellagic acid</a></li> <li><a href="/wiki/Engeletin" title="Engeletin">Engeletin</a></li> <li><a href="/wiki/Epicatechin_gallate" title="Epicatechin gallate">Epicatechin gallate</a></li> <li><a href="/wiki/Epigallocatechin" class="mw-redirect" title="Epigallocatechin">Epigallocatechin</a></li> <li><a href="/wiki/Epsilon-viniferin" class="mw-redirect" title="Epsilon-viniferin">Epsilon-viniferin</a></li> <li><a href="/wiki/Ethyl_caffeate" title="Ethyl caffeate">Ethyl caffeate</a></li> <li><a href="/wiki/Ethyl_gallate" title="Ethyl gallate">Ethyl gallate</a></li> <li><a href="/wiki/Ethyl_protocatechuate" title="Ethyl protocatechuate">Ethyl protocatechuate</a></li> <li><a href="/wiki/4-Ethylguaiacol" title="4-Ethylguaiacol">4-Ethylguaiacol</a></li> <li><a href="/wiki/4-Ethylphenol" title="4-Ethylphenol">4-Ethylphenol</a></li> <li><a href="/wiki/Fertaric_acid" title="Fertaric acid">Fertaric acid</a></li> <li><a href="/wiki/Ferulic_acid" title="Ferulic acid">Ferulic acid</a></li> <li><a href="/wiki/Gallic_acid" title="Gallic acid">Gallic acid</a><sup id="cite_ref-:0_45-2" class="reference"><a href="#cite_note-:0-45"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup></li> <li><a href="/wiki/Gentisic_acid" title="Gentisic acid">Gentisic acid</a></li> <li><a href="/wiki/Grandinin" title="Grandinin">Grandinin</a></li> <li><a href="/wiki/Grape_reaction_product" title="Grape reaction product">Grape reaction product</a> (GRP)</li> <li><a href="/wiki/Guaiacol" title="Guaiacol">Guaiacol</a></li> <li><a href="/wiki/Hopeaphenol" title="Hopeaphenol">Hopeaphenol</a></li> <li><a href="/wiki/P-Hydroxybenzoic_acid" class="mw-redirect" title="P-Hydroxybenzoic acid">p-Hydroxybenzoic acid</a></li> <li><a href="/w/index.php?title=Isorhamnetol_3-glucoside&action=edit&redlink=1" class="new" title="Isorhamnetol 3-glucoside (page does not exist)">Isorhamnetol 3-glucoside</a></li> <li><a href="/wiki/Kaempferol" title="Kaempferol">Kaempferol</a></li> <li><a href="/wiki/Kaempferol_glucoside" class="mw-redirect" title="Kaempferol glucoside">Kaempferol glucoside</a> (astragalin)</li> <li><a href="/w/index.php?title=Kaempferol_glucuronide&action=edit&redlink=1" class="new" title="Kaempferol glucuronide (page does not exist)">Kaempferol glucuronide</a></li> <li><a href="/wiki/Malvidin" title="Malvidin">Malvidin</a></li> <li><a href="/wiki/Malvidin_3O-glucoside" class="mw-redirect" title="Malvidin 3O-glucoside">Malvidin 3O-glucoside</a> (oenin)</li> <li><a href="/w/index.php?title=Malvidin_acetyl-3O-glucoside&action=edit&redlink=1" class="new" title="Malvidin acetyl-3O-glucoside (page does not exist)">Malvidin acetyl-3O-glucoside</a></li> <li><a href="/w/index.php?title=Malvidin_cafeoyl-3O-glucoside&action=edit&redlink=1" class="new" title="Malvidin cafeoyl-3O-glucoside (page does not exist)">Malvidin cafeoyl-3O-glucoside</a></li> <li><a href="/wiki/Malvidin_coumaroyl-3Oglucoside" class="mw-redirect" title="Malvidin coumaroyl-3Oglucoside">Malvidin coumaroyl-3Oglucoside</a></li> <li><a href="/wiki/Malvidin_glucoside-ethyl-catechin" title="Malvidin glucoside-ethyl-catechin">Malvidin glucoside-ethyl-catechin</a></li> <li><a href="/w/index.php?title=Malvidin-3-O-glucoside-pyruvic_acid&action=edit&redlink=1" class="new" title="Malvidin-3-O-glucoside-pyruvic acid (page does not exist)">Malvidin-3-O-glucoside-pyruvic acid</a></li> <li><a href="/w/index.php?title=Malvidin-3-O-acetylglucoside-pyruvic_acid&action=edit&redlink=1" class="new" title="Malvidin-3-O-acetylglucoside-pyruvic acid (page does not exist)">Malvidin-3-O-acetylglucoside-pyruvic acid</a></li> <li><a href="/w/index.php?title=Malvidin-3-O-coumaroylglucoside-pyruvic_acid&action=edit&redlink=1" class="new" title="Malvidin-3-O-coumaroylglucoside-pyruvic acid (page does not exist)">Malvidin-3-O-coumaroylglucoside-pyruvic acid</a></li> <li><a href="/w/index.php?title=Malvidin-3-O-glucoside-acetaldehyde&action=edit&redlink=1" class="new" title="Malvidin-3-O-glucoside-acetaldehyde (page does not exist)">Malvidin-3-O-glucoside-acetaldehyde</a></li> <li><a href="/w/index.php?title=Malvidin-3-O-acetylglucoside-acetaldehyde&action=edit&redlink=1" class="new" title="Malvidin-3-O-acetylglucoside-acetaldehyde (page does not exist)">Malvidin-3-O-acetylglucoside-acetaldehyde</a></li> <li><a href="/w/index.php?title=Malvidin-3-O-coumaroylglucoside-acetaldehyde&action=edit&redlink=1" class="new" title="Malvidin-3-O-coumaroylglucoside-acetaldehyde (page does not exist)">Malvidin-3-O-coumaroylglucoside-acetaldehyde</a></li> <li><a href="/w/index.php?title=Malvidin-3-O-glucoside-4-vinylcatechol&action=edit&redlink=1" class="new" title="Malvidin-3-O-glucoside-4-vinylcatechol (page does not exist)">Malvidin-3-O-glucoside-4-vinylcatechol</a></li> <li><a href="/w/index.php?title=Malvidin-3-O-acetylglucoside-4-vinylcatechol&action=edit&redlink=1" class="new" title="Malvidin-3-O-acetylglucoside-4-vinylcatechol (page does not exist)">Malvidin-3-O-acetylglucoside-4-vinylcatechol</a></li> <li><a href="/w/index.php?title=Malvidin-3-O-coumaroylglucoside-4-vinylcatechol&action=edit&redlink=1" class="new" title="Malvidin-3-O-coumaroylglucoside-4-vinylcatechol (page does not exist)">Malvidin-3-O-coumaroylglucoside-4-vinylcatechol</a></li> <li><a href="/w/index.php?title=Malvidin-3-O-glucoside-4-vinylphenol&action=edit&redlink=1" class="new" title="Malvidin-3-O-glucoside-4-vinylphenol (page does not exist)">Malvidin-3-O-glucoside-4-vinylphenol</a></li> <li><a href="/w/index.php?title=Malvidin-3-O-acetylglucoside-4-vinylphenol&action=edit&redlink=1" class="new" title="Malvidin-3-O-acetylglucoside-4-vinylphenol (page does not exist)">Malvidin-3-O-acetylglucoside-4-vinylphenol</a></li> <li><a href="/w/index.php?title=Malvidin-3-O-coumaroylglucoside-4-vinylphenol&action=edit&redlink=1" class="new" title="Malvidin-3-O-coumaroylglucoside-4-vinylphenol (page does not exist)">Malvidin-3-O-coumaroylglucoside-4-vinylphenol</a></li> <li><a href="/w/index.php?title=Malvidin-3-O-caffeoylglucoside-4-vinylphenol&action=edit&redlink=1" class="new" title="Malvidin-3-O-caffeoylglucoside-4-vinylphenol (page does not exist)">Malvidin-3-O-caffeoylglucoside-4-vinylphenol</a></li> <li><a href="/w/index.php?title=Malvidin-3-O-glucoside-4-vinylguaiacol&action=edit&redlink=1" class="new" title="Malvidin-3-O-glucoside-4-vinylguaiacol (page does not exist)">Malvidin-3-O-glucoside-4-vinylguaiacol</a></li> <li><a href="/w/index.php?title=Malvidin-3-O-acetylglucoside-4-vinylguaiacol&action=edit&redlink=1" class="new" title="Malvidin-3-O-acetylglucoside-4-vinylguaiacol (page does not exist)">Malvidin-3-O-acetylglucoside-4-vinylguaiacol</a></li> <li><a href="/w/index.php?title=Malvidin-3-O-coumaroylglucoside-vinylguaiacol&action=edit&redlink=1" class="new" title="Malvidin-3-O-coumaroylglucoside-vinylguaiacol (page does not exist)">Malvidin-3-O-coumaroylglucoside-vinylguaiacol</a></li> <li><a href="/w/index.php?title=Malvidin-3-O-glucoside-4-vinyl(epi)catechin&action=edit&redlink=1" class="new" title="Malvidin-3-O-glucoside-4-vinyl(epi)catechin (page does not exist)">Malvidin-3-O-glucoside-4-vinyl(epi)catechin</a></li> <li><a href="/w/index.php?title=Malvidin-3-O-acetylglucoside-4-vinyl(epi)catechin&action=edit&redlink=1" class="new" title="Malvidin-3-O-acetylglucoside-4-vinyl(epi)catechin (page does not exist)">Malvidin-3-O-acetylglucoside-4-vinyl(epi)catechin</a></li> <li><a href="/w/index.php?title=Malvidin-3-O-coumaroylglucoside-4-vinyl(epi)catechin&action=edit&redlink=1" class="new" title="Malvidin-3-O-coumaroylglucoside-4-vinyl(epi)catechin (page does not exist)">Malvidin-3-O-coumaroylglucoside-4-vinyl(epi)catechin</a></li> <li><a href="/wiki/Methyl_gallate" title="Methyl gallate">Methyl gallate</a></li> <li><a href="/wiki/Myricetol" class="mw-redirect" title="Myricetol">Myricetol</a></li> <li><a href="/w/index.php?title=Myricetol_3-glucoside&action=edit&redlink=1" class="new" title="Myricetol 3-glucoside (page does not exist)">Myricetol 3-glucoside</a></li> <li><a href="/w/index.php?title=Myricetol_3-glucuronide&action=edit&redlink=1" class="new" title="Myricetol 3-glucuronide (page does not exist)">Myricetol 3-glucuronide</a></li> <li><a href="/wiki/Oxovitisin_A" title="Oxovitisin A">Oxovitisin A</a></li> <li><a href="/wiki/Pallidol" title="Pallidol">Pallidol</a></li> <li><a href="/wiki/Pelargonin" title="Pelargonin">Pelargonin</a> (Pelargonidin 3,5-O-diglucoside)</li> <li><a href="/wiki/Peonidin_3O-glucoside" class="mw-redirect" title="Peonidin 3O-glucoside">Peonidin 3O-glucoside</a></li> <li><a href="/w/index.php?title=Peonidin_acetyl-3O-glucoside&action=edit&redlink=1" class="new" title="Peonidin acetyl-3O-glucoside (page does not exist)">Peonidin acetyl-3O-glucoside</a></li> <li><a href="/w/index.php?title=Peonidin-3-(6-p-caffeoyl)-glucoside&action=edit&redlink=1" class="new" title="Peonidin-3-(6-p-caffeoyl)-glucoside (page does not exist)">Peonidin-3-(6-p-caffeoyl)-glucoside</a></li> <li><a href="/w/index.php?title=Peonidin_coumaroyl_3O-glucoside&action=edit&redlink=1" class="new" title="Peonidin coumaroyl 3O-glucoside (page does not exist)">Peonidin coumaroyl 3O-glucoside</a></li> <li><a href="/w/index.php?title=Peonidin-3-O-glucoside-pyruvic_acid&action=edit&redlink=1" class="new" title="Peonidin-3-O-glucoside-pyruvic acid (page does not exist)">Peonidin-3-O-glucoside-pyruvic acid</a></li> <li><a href="/w/index.php?title=Peonidin-3-O-acetylglucoside-pyruvic_acid&action=edit&redlink=1" class="new" title="Peonidin-3-O-acetylglucoside-pyruvic acid (page does not exist)">Peonidin-3-O-acetylglucoside-pyruvic acid</a></li> <li><a href="/w/index.php?title=Peonidin-3-O-coumaroylglucoside-pyruvic_acid&action=edit&redlink=1" class="new" title="Peonidin-3-O-coumaroylglucoside-pyruvic acid (page does not exist)">Peonidin-3-O-coumaroylglucoside-pyruvic acid</a></li> <li><a href="/w/index.php?title=Peonidin-3-O-glucoside-4-vinylcatechol&action=edit&redlink=1" class="new" title="Peonidin-3-O-glucoside-4-vinylcatechol (page does not exist)">Peonidin-3-O-glucoside-4-vinylcatechol</a></li> <li><a href="/w/index.php?title=Peonidin-3-O-acetylglucoside-4-vinylcatechol&action=edit&redlink=1" class="new" title="Peonidin-3-O-acetylglucoside-4-vinylcatechol (page does not exist)">Peonidin-3-O-acetylglucoside-4-vinylcatechol</a></li> <li><a href="/w/index.php?title=Peonidin-3-O-coumaroylglucoside-4-vinylcatechol&action=edit&redlink=1" class="new" title="Peonidin-3-O-coumaroylglucoside-4-vinylcatechol (page does not exist)">Peonidin-3-O-coumaroylglucoside-4-vinylcatechol</a></li> <li><a href="/w/index.php?title=Peonidin-3-O-glucoside-4-vinylphenol&action=edit&redlink=1" class="new" title="Peonidin-3-O-glucoside-4-vinylphenol (page does not exist)">Peonidin-3-O-glucoside-4-vinylphenol</a></li> <li><a href="/w/index.php?title=Peonidin-3-O-acetylglucoside-4-vinylphenol&action=edit&redlink=1" class="new" title="Peonidin-3-O-acetylglucoside-4-vinylphenol (page does not exist)">Peonidin-3-O-acetylglucoside-4-vinylphenol</a></li> <li><a href="/w/index.php?title=Peonidin-3-O-coumaroylglucoside-4-vinylphenol&action=edit&redlink=1" class="new" title="Peonidin-3-O-coumaroylglucoside-4-vinylphenol (page does not exist)">Peonidin-3-O-coumaroylglucoside-4-vinylphenol</a></li> <li><a href="/w/index.php?title=Peonidin-3-O-glucoside-4-vinylguaiacol&action=edit&redlink=1" class="new" title="Peonidin-3-O-glucoside-4-vinylguaiacol (page does not exist)">Peonidin-3-O-glucoside-4-vinylguaiacol</a></li> <li><a href="/w/index.php?title=Peonidin-3-O-glucoside-4-vinyl(epi)catechin&action=edit&redlink=1" class="new" title="Peonidin-3-O-glucoside-4-vinyl(epi)catechin (page does not exist)">Peonidin-3-O-glucoside-4-vinyl(epi)catechin</a></li> <li><a href="/w/index.php?title=Peonidin-3-O-acetylglucoside-4-vinyl(epi)catechin&action=edit&redlink=1" class="new" title="Peonidin-3-O-acetylglucoside-4-vinyl(epi)catechin (page does not exist)">Peonidin-3-O-acetylglucoside-4-vinyl(epi)catechin</a></li> <li><a href="/wiki/Petunidin" title="Petunidin">Petunidin</a></li> <li><a href="/w/index.php?title=Petunidin_3O_glucoside&action=edit&redlink=1" class="new" title="Petunidin 3O glucoside (page does not exist)">Petunidin 3O glucoside</a></li> <li><a href="/w/index.php?title=Petunidin_acetyl-3O-glucoside&action=edit&redlink=1" class="new" title="Petunidin acetyl-3O-glucoside (page does not exist)">Petunidin acetyl-3O-glucoside</a></li> <li><a href="/w/index.php?title=Petunidin_coumaroyl-3O_glucoside&action=edit&redlink=1" class="new" title="Petunidin coumaroyl-3O glucoside (page does not exist)">Petunidin coumaroyl-3O glucoside</a></li> <li><a href="/w/index.php?title=Petunidin-3-O-glucoside-pyruvic_acid&action=edit&redlink=1" class="new" title="Petunidin-3-O-glucoside-pyruvic acid (page does not exist)">Petunidin-3-O-glucoside-pyruvic acid</a></li> <li><a href="/w/index.php?title=Petunidin-3-O-acetylglucoside-pyruvic_acid&action=edit&redlink=1" class="new" title="Petunidin-3-O-acetylglucoside-pyruvic acid (page does not exist)">Petunidin-3-O-acetylglucoside-pyruvic acid</a></li> <li><a href="/w/index.php?title=Petunidin-3-O-coumaroylglucoside-pyruvic_acid&action=edit&redlink=1" class="new" title="Petunidin-3-O-coumaroylglucoside-pyruvic acid (page does not exist)">Petunidin-3-O-coumaroylglucoside-pyruvic acid</a></li> <li><a href="/w/index.php?title=Petunidin-3-O-glucoside-4-vinylcatechol&action=edit&redlink=1" class="new" title="Petunidin-3-O-glucoside-4-vinylcatechol (page does not exist)">Petunidin-3-O-glucoside-4-vinylcatechol</a></li> <li><a href="/w/index.php?title=Petunidin-3-O-acetylglucoside-4-vinylcatechol&action=edit&redlink=1" class="new" title="Petunidin-3-O-acetylglucoside-4-vinylcatechol (page does not exist)">Petunidin-3-O-acetylglucoside-4-vinylcatechol</a></li> <li><a href="/w/index.php?title=Petunidin-3-O-coumaroylglucoside-4-vinylcatechol&action=edit&redlink=1" class="new" title="Petunidin-3-O-coumaroylglucoside-4-vinylcatechol (page does not exist)">Petunidin-3-O-coumaroylglucoside-4-vinylcatechol</a></li> <li><a href="/w/index.php?title=Petunidin-3-O-glucoside-4-vinylphenol&action=edit&redlink=1" class="new" title="Petunidin-3-O-glucoside-4-vinylphenol (page does not exist)">Petunidin-3-O-glucoside-4-vinylphenol</a></li> <li><a href="/w/index.php?title=Petunidin-3-O-acetylglucoside-4-vinylphenol&action=edit&redlink=1" class="new" title="Petunidin-3-O-acetylglucoside-4-vinylphenol (page does not exist)">Petunidin-3-O-acetylglucoside-4-vinylphenol</a></li> <li><a href="/w/index.php?title=Petunidin-3-O-coumaroylglucoside-4-vinylphenol&action=edit&redlink=1" class="new" title="Petunidin-3-O-coumaroylglucoside-4-vinylphenol (page does not exist)">Petunidin-3-O-coumaroylglucoside-4-vinylphenol</a></li> <li><a href="/w/index.php?title=Petunidin-3-O-glucoside-4-vinylguaiacol&action=edit&redlink=1" class="new" title="Petunidin-3-O-glucoside-4-vinylguaiacol (page does not exist)">Petunidin-3-O-glucoside-4-vinylguaiacol</a></li> <li><a href="/w/index.php?title=Petunidin-3-O-glucoside-4-vinyl(epi)catechin&action=edit&redlink=1" class="new" title="Petunidin-3-O-glucoside-4-vinyl(epi)catechin (page does not exist)">Petunidin-3-O-glucoside-4-vinyl(epi)catechin</a></li> <li><a href="/w/index.php?title=Petunidin-3-O-acetylglucoside-4-vinyl(epi)catechin&action=edit&redlink=1" class="new" title="Petunidin-3-O-acetylglucoside-4-vinyl(epi)catechin (page does not exist)">Petunidin-3-O-acetylglucoside-4-vinyl(epi)catechin</a></li> <li><a href="/wiki/Phloroglucinol_carboxylic_acid" title="Phloroglucinol carboxylic acid">Phloroglucinol carboxylic acid</a></li> <li><a href="/wiki/Piceatannol" title="Piceatannol">Piceatannol</a></li> <li><a href="/wiki/Piceid" title="Piceid">Piceids</a></li> <li><a href="/wiki/Pinotin_A" title="Pinotin A">Pinotin A</a></li> <li>Oligomeric procyanidins : <ul><li><a href="/wiki/Procyanidin_B1" title="Procyanidin B1">Procyanidin B1</a></li> <li><a href="/wiki/Procyanidin_B2" title="Procyanidin B2">Procyanidin B2</a></li> <li><a href="/wiki/Procyanidin_B3" title="Procyanidin B3">Procyanidin B3</a></li> <li><a href="/wiki/Procyanidin_B4" title="Procyanidin B4">Procyanidin B4</a></li> <li><a href="/w/index.php?title=B1-3-O-gallate&action=edit&redlink=1" class="new" title="B1-3-O-gallate (page does not exist)">B1-3-O-gallate</a></li> <li><a href="/w/index.php?title=B2-3-O-gallate&action=edit&redlink=1" class="new" title="B2-3-O-gallate (page does not exist)">B2-3-O-gallate</a></li> <li><a href="/w/index.php?title=B2-3%27-O-gallate&action=edit&redlink=1" class="new" title="B2-3'-O-gallate (page does not exist)">B2-3'-O-gallate</a></li> <li><a href="/wiki/Procyanidin_C1" title="Procyanidin C1">procyanidin C1</a> (epicatechin-(4β→8)-epicatechin-(4β→8)-epicatechin)</li> <li><a href="/wiki/Procyanidin_C2" title="Procyanidin C2">Procyanidin C2</a> (catechin-(4α→8)-catechin-(4α→8)-catechin)</li> <li><a href="/w/index.php?title=Procyanidin_T2&action=edit&redlink=1" class="new" title="Procyanidin T2 (page does not exist)">procyanidin T2</a> (trimer)<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></li></ul></li> <li><a href="/wiki/Protocatechuic_acid" title="Protocatechuic acid">Protocatechuic acid</a></li> <li><a href="/wiki/Protocatechuic_aldehyde" title="Protocatechuic aldehyde">protocatechuic aldehyde</a></li> <li><a href="/wiki/Quercetin" title="Quercetin">Quercetin</a></li> <li><a href="/wiki/Quercetol_glucoside" class="mw-redirect" title="Quercetol glucoside">Quercetol glucoside</a></li> <li><a href="/wiki/Quercetin_3-O-glucuronide" class="mw-redirect" title="Quercetin 3-O-glucuronide">Quercetol glucuronide</a></li> <li><a href="/wiki/Resveratrol" title="Resveratrol">Resveratrol</a></li> <li><a href="/wiki/Roburin_A" title="Roburin A">Roburin A</a></li> <li><a href="/w/index.php?title=Roburin_E&action=edit&redlink=1" class="new" title="Roburin E (page does not exist)">Roburin E</a></li> <li><a href="/wiki/Scopoletin" title="Scopoletin">Scopoletin</a></li> <li><a href="/wiki/Sinapic_aldehyde" class="mw-redirect" title="Sinapic aldehyde">Sinapic aldehyde</a></li> <li><a href="/wiki/Sinapinic_acid" title="Sinapinic acid">Sinapinic acid</a></li> <li><a href="/wiki/Syringic_acid" title="Syringic acid">Syringic acid</a></li> <li><a href="/wiki/Tyrosol" title="Tyrosol">Tyrosol</a></li> <li><a href="/wiki/Vanillic_acid" title="Vanillic acid">Vanillic acid</a></li> <li><a href="/wiki/Vanillin" title="Vanillin">vanillin</a></li> <li><a href="/wiki/Vescalagin" class="mw-redirect" title="Vescalagin">Vescalagin</a></li> <li><a href="/wiki/4-Vinylphenol" title="4-Vinylphenol">4-Vinylphenol</a></li> <li><a href="/wiki/Vitisin_A_(pyranoanthocyanin)" title="Vitisin A (pyranoanthocyanin)">Vitisin A</a></li> <li><a href="/wiki/Vitisin_B_(pyranoanthocyanin)" title="Vitisin B (pyranoanthocyanin)">Vitisin B</a></li> <li><a href="/w/index.php?title=Vinylpyranomalvidin-3O-glucoside-procyanidin_dimer&action=edit&redlink=1" class="new" title="Vinylpyranomalvidin-3O-glucoside-procyanidin dimer (page does not exist)">Vinylpyranomalvidin-3O-glucoside-procyanidin dimer</a></li> <li><a href="/w/index.php?title=VinylpyranoMv-3-coumaroylglucoside-procyanidin_dimer&action=edit&redlink=1" class="new" title="VinylpyranoMv-3-coumaroylglucoside-procyanidin dimer (page does not exist)">VinylpyranoMv-3-coumaroylglucoside-procyanidin dimer</a></li> <li><a href="/w/index.php?title=Vinylpyranomalvidin-3O-glucoside-catechin&action=edit&redlink=1" class="new" title="Vinylpyranomalvidin-3O-glucoside-catechin (page does not exist)">Vinylpyranomalvidin-3O-glucoside-catechin</a></li> <li><a href="/w/index.php?title=Vinylpyranomalvidin-3O-coumaroylglucoside-catechin&action=edit&redlink=1" class="new" title="Vinylpyranomalvidin-3O-coumaroylglucoside-catechin (page does not exist)">Vinylpyranomalvidin-3O-coumaroylglucoside-catechin</a></li> <li><a href="/w/index.php?title=Vinylpyranomalvidin-3O-phenol&action=edit&redlink=1" class="new" title="Vinylpyranomalvidin-3O-phenol (page does not exist)">Vinylpyranomalvidin-3O-phenol</a></li> <li><a href="/w/index.php?title=Vinylpyranopetunidin-3O-glucoside-catechin&action=edit&redlink=1" class="new" title="Vinylpyranopetunidin-3O-glucoside-catechin (page does not exist)">Vinylpyranopetunidin-3O-glucoside-catechin</a></li> <li><a href="/w/index.php?title=Vinylpyranopeonidin-3O-glucoside-catechin&action=edit&redlink=1" class="new" title="Vinylpyranopeonidin-3O-glucoside-catechin (page does not exist)">Vinylpyranopeonidin-3O-glucoside-catechin</a></li> <li><a href="/w/index.php?title=Vinylpyranomalvidin-3O-acetylglucoside-catechin&action=edit&redlink=1" class="new" title="Vinylpyranomalvidin-3O-acetylglucoside-catechin (page does not exist)">Vinylpyranomalvidin-3O-acetylglucoside-catechin</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="Effects">Effects</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phenolic_content_in_wine&action=edit&section=20" title="Edit section: Effects"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Polyphenol compounds may interact with <a href="/wiki/Volatile_organic_compounds" class="mw-redirect" title="Volatile organic compounds">volatiles</a> and contribute to the aromas in wine.<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> Although wine polyphenols are speculated to provide <a href="/wiki/Antioxidant" title="Antioxidant">antioxidant</a> or other benefits, there is little evidence that wine polyphenols actually have any effect in humans.<sup id="cite_ref-Haseeb_50-0" class="reference"><a href="#cite_note-Haseeb-50"><span class="cite-bracket">[</span>50<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-lpi_51-0" class="reference"><a href="#cite_note-lpi-51"><span class="cite-bracket">[</span>51<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-EFSA_52-0" class="reference"><a href="#cite_note-EFSA-52"><span class="cite-bracket">[</span>52<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-53" class="reference"><a href="#cite_note-53"><span class="cite-bracket">[</span>53<span class="cite-bracket">]</span></a></sup> Limited preliminary research indicates that wine polyphenols may decrease <a href="/wiki/Platelet_aggregation" class="mw-redirect" title="Platelet aggregation">platelet aggregation</a>, enhance <a href="/wiki/Fibrinolysis" title="Fibrinolysis">fibrinolysis</a>, and increase <a href="/wiki/HDL_cholesterol" class="mw-redirect" title="HDL cholesterol">HDL cholesterol</a>, but high-quality <a href="/wiki/Clinical_trial" title="Clinical trial">clinical trials</a> have not confirmed such effects, as of 2017.<sup id="cite_ref-Haseeb_50-1" class="reference"><a href="#cite_note-Haseeb-50"><span class="cite-bracket">[</span>50<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phenolic_content_in_wine&action=edit&section=21" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Aging_of_wine" title="Aging of wine">Aging of wine</a></li> <li><a href="/wiki/Clarification_and_stabilization_of_wine" title="Clarification and stabilization of wine">Clarification and stabilization of wine</a></li> <li><a href="/wiki/Grape_seed_extract" title="Grape seed extract">Grape seed extract</a></li> <li><a href="/wiki/Phenolic_content_in_tea" title="Phenolic content in tea">Phenolic content in tea</a></li> <li><a href="/wiki/Wine_chemistry" title="Wine chemistry">Wine chemistry</a></li> <li><a href="/wiki/Wine_preservatives" title="Wine preservatives">Wine preservatives</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phenolic_content_in_wine&action=edit&section=22" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist reflist-columns references-column-width" style="column-width: 30em;"> <ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFKennedyMatthewsWaterhouse2002" class="citation journal cs1">Kennedy JA, Matthews MA, Waterhouse AL (2002). <a rel="nofollow" class="external text" href="http://www.ajevonline.org/cgi/content/abstract/53/4/268">"Effect of Maturity and Vine Water Status on Grape Skin 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Vitic</i>. <b>53</b> (4): 268–74. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.5344%2Fajev.2002.53.4.268">10.5344/ajev.2002.53.4.268</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:10545757">10545757</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Am.+J.+Enol.+Vitic.&rft.atitle=Effect+of+Maturity+and+Vine+Water+Status+on+Grape+Skin+and+Wine+Flavonoids&rft.volume=53&rft.issue=4&rft.pages=268-74&rft.date=2002&rft_id=info%3Adoi%2F10.5344%2Fajev.2002.53.4.268&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A10545757%23id-name%3DS2CID&rft.aulast=Kennedy&rft.aufirst=JA&rft.au=Matthews%2C+MA&rft.au=Waterhouse%2C+AL&rft_id=http%3A%2F%2Fwww.ajevonline.org%2Fcgi%2Fcontent%2Fabstract%2F53%2F4%2F268&rfr_id=info%3Asid%2Fen.wikipedia.org%3APhenolic+content+in+wine" class="Z3988"></span></span> </li> <li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCosta_de_CamargoBismara_Regitano-d'ArceCamarão_Telles_BiasotoShahidi2014" class="citation journal cs1">Costa de Camargo, Adriano; Bismara Regitano-d'Arce, Marisa Aparecida; Camarão Telles Biasoto, Aline; Shahidi, Fereidoon (2014). 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title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Cardiovasc+Res&rft.atitle=Dietary+polyphenols%3A+Good%2C+bad%2C+or+indifferent+for+your+health%3F&rft.volume=73&rft.issue=2&rft.pages=341-347&rft.date=2007&rft_id=info%3Adoi%2F10.1016%2Fj.cardiores.2006.10.004&rft_id=info%3Apmid%2F17141749&rft.au=Halliwell+B&rft_id=https%3A%2F%2Fdoi.org%2F10.1016%252Fj.cardiores.2006.10.004&rfr_id=info%3Asid%2Fen.wikipedia.org%3APhenolic+content+in+wine" 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=Phenolic_content_in_wine&action=edit&section=23" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a rel="nofollow" class="external text" href="http://www.guideduvin.com/polyphenols">Wine polyphenols vary with age and variety (Polyphenols on www.guideduvin.com)</a> <span class="languageicon">(in French)</span></li> <li><a rel="nofollow" class="external text" href="http://www.phenol-explorer.eu/contents?options%5Blist_by%5D=compounds&options%5Blist_format%5D=crosstab">Polyphenol concentrations in red, white and rosé wines at www.phenol-explorer.eu</a></li></ul>    </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=Phenolic_content_in_wine&oldid=1244201645">https://en.wikipedia.org/w/index.php?title=Phenolic_content_in_wine&oldid=1244201645</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" 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