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<h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Flavonole</span></h1>
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<p>Die <b>Flavonole</b> sind eine Untergruppe <a href="Sekund%C3%A4re_Pflanzenstoffe" title="Sekundäre Pflanzenstoffe">sekundärer Pflanzenstoffe</a> innerhalb der Stoffgruppe der <a href="Flavonoide" title="Flavonoide">Flavonoide</a>. Die Flavonole besitzen im Unterschied zu den <a href="Flavone" title="Flavone">Flavonen</a>, einer weiteren Untergruppe der Flavonoide, eine zusätzliche <a href="Hydroxygruppe" title="Hydroxygruppe">Hydroxygruppe</a> in Position 3. Das Grundgerüst der Flavonole ist somit die Verbindung 3-Hydroxyflavon. Die einzelnen Flavonole unterscheiden sich voneinander durch das Substitutionsmuster des 3-Hydroxyflavon-Grundgerüsts mit Hydroxygruppen und durch die Art der weiteren Derivatisierung dieser hydroxylierten 3-Hydroxyflavone durch u. a. <i>O</i>-Alkylierung, meist in der Form von <i>O</i>-Methylierung und/oder durch die <i>O</i>-glycosidische Anbindung von Saccharid-Resten unter Bildung von <a href="Glycoside" title="Glycoside">Glycosiden</a>.<sup id="cite_ref-Nuhn_1-0" class="reference"><a href="#cite_note-Nuhn-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Herrmann_2-0" class="reference"><a href="#cite_note-Herrmann-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup>
</p>
<div class="mw-heading mw-heading2"><h2 id="Nicht-glycosylierte_Flavonole">Nicht-glycosylierte Flavonole</h2></div>
<p>Die häufigsten Flavonole sind <a href="Kaempferol" title="Kaempferol">Kaempferol</a>, <a href="Quercetin" title="Quercetin">Quercetin</a>, <a href="Isorhamnetin" title="Isorhamnetin">Isorhamnetin</a> und <a href="Myricetin" title="Myricetin">Myricetin</a>. Typisch für die gängigen Flavonole ist, dass neben der Position 3 auch die Positionen 5 und 7 am A-Ring Hydroxygruppen tragen. Bzgl. der Substitution des B-Rings ist die gleichzeitige Hydroxylierung der Positionen 3' und 4' am gängigsten gefolgt von der einfachen Hydroxylierung in Position 4'. Die typischsten Flavonole sind somit Quercetin und Kaempferol.<sup id="cite_ref-Herrmann_2-1" class="reference"><a href="#cite_note-Herrmann-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup>
</p>
<table class="wikitable">
<caption>Beispiele für Flavonole
</caption>
<tbody><tr>
<th>Name
</th>
<th>CAS
</th>
<th>3
</th>
<th>5
</th>
<th>6
</th>
<th>7
</th>
<th>8
</th>
<th>2′
</th>
<th>3′
</th>
<th>4′
</th>
<th>5′
</th>
<th>6′
</th></tr>
<tr>
<td>Azaleatin
</td>
<td><span title="Untervorlage eingebunden: CASRN"></span><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=529-51-1">529-51-1</a><span class="editoronly" style="display:none;"></span>
</td>
<td>OH
</td>
<td>OCH<sub>3</sub>
</td>
<td>H
</td>
<td>OH
</td>
<td>H
</td>
<td>H
</td>
<td>OH
</td>
<td>OH
</td>
<td>H
</td>
<td>H
</td></tr>
<tr>
<td><a href="Fisetin" title="Fisetin">Fisetin</a>
</td>
<td><span title="Untervorlage eingebunden: CASRN"></span><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=528-48-3">528-48-3</a><span class="editoronly" style="display:none;"></span>
</td>
<td>OH
</td>
<td>H
</td>
<td>H
</td>
<td>OH
</td>
<td>H
</td>
<td>H
</td>
<td>OH
</td>
<td>OH
</td>
<td>H
</td>
<td>H
</td></tr>
<tr>
<td>Galangin
</td>
<td><span title="Untervorlage eingebunden: CASRN"></span><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=548-83-4">548-83-4</a><span class="editoronly" style="display:none;"></span>
</td>
<td>OH
</td>
<td>OH
</td>
<td>H
</td>
<td>OH
</td>
<td>H
</td>
<td>H
</td>
<td>H
</td>
<td>H
</td>
<td>H
</td>
<td>H
</td></tr>
<tr>
<td>Gossypetin
</td>
<td><span title="Untervorlage eingebunden: CASRN"></span><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=489-35-0">489-35-0</a><span class="editoronly" style="display:none;"></span>
</td>
<td>OH
</td>
<td>OH
</td>
<td>H
</td>
<td>OH
</td>
<td>OH
</td>
<td>H
</td>
<td>OH
</td>
<td>OH
</td>
<td>H
</td>
<td>H
</td></tr>
<tr>
<td><a href="Isorhamnetin" title="Isorhamnetin">Isorhamnetin</a>
</td>
<td><span title="Untervorlage eingebunden: CASRN"></span><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=480-19-3">480-19-3</a><span class="editoronly" style="display:none;"></span>
</td>
<td>OH
</td>
<td>OH
</td>
<td>H
</td>
<td>OH
</td>
<td>H
</td>
<td>H
</td>
<td>OCH<sub>3</sub>
</td>
<td>OH
</td>
<td>H
</td>
<td>H
</td></tr>
<tr>
<td>Kaempferid
</td>
<td><span title="Untervorlage eingebunden: CASRN"></span><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=491-54-3">491-54-3</a><span class="editoronly" style="display:none;"></span>
</td>
<td>OH
</td>
<td>OH
</td>
<td>H
</td>
<td>OH
</td>
<td>H
</td>
<td>H
</td>
<td>H
</td>
<td>OCH<sub>3</sub>
</td>
<td>H
</td>
<td>H
</td></tr>
<tr>
<td><b><a href="Kaempferol" title="Kaempferol">Kaempferol</a></b>
</td>
<td><span title="Untervorlage eingebunden: CASRN"></span><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=520-18-3">520-18-3</a><span class="editoronly" style="display:none;"></span>
</td>
<td>OH
</td>
<td>OH
</td>
<td>H
</td>
<td>OH
</td>
<td>H
</td>
<td>H
</td>
<td>H
</td>
<td>OH
</td>
<td>H
</td>
<td>H
</td></tr>
<tr>
<td><a href="Morin_(Farbstoff)" title="Morin (Farbstoff)">Morin</a>
</td>
<td><span title="Untervorlage eingebunden: CASRN"></span><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=480-16-0">480-16-0</a><span class="editoronly" style="display:none;"></span>
</td>
<td>OH
</td>
<td>OH
</td>
<td>H
</td>
<td>OH
</td>
<td>H
</td>
<td>OH
</td>
<td>H
</td>
<td>OH
</td>
<td>H
</td>
<td>H
</td></tr>
<tr>
<td><b><a href="Myricetin" title="Myricetin">Myricetin</a></b>
</td>
<td><span title="Untervorlage eingebunden: CASRN"></span><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=529-44-2">529-44-2</a><span class="editoronly" style="display:none;"></span>
</td>
<td>OH
</td>
<td>OH
</td>
<td>H
</td>
<td>OH
</td>
<td>H
</td>
<td>H
</td>
<td>OH
</td>
<td>OH
</td>
<td>OH
</td>
<td>H
</td></tr>
<tr>
<td>Natsudaidain
</td>
<td><span title="Untervorlage eingebunden: CASRN"></span><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=35154-55-3">35154-55-3</a><span class="editoronly" style="display:none;"></span>
</td>
<td>OH
</td>
<td>OCH<sub>3</sub>
</td>
<td>OCH<sub>3</sub>
</td>
<td>OCH<sub>3</sub>
</td>
<td>OCH<sub>3</sub>
</td>
<td>H
</td>
<td>OCH<sub>3</sub>
</td>
<td>OCH<sub>3</sub>
</td>
<td>H
</td>
<td>H
</td></tr>
<tr>
<td>Pachypodol
</td>
<td><span title="Untervorlage eingebunden: CASRN"></span><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=33708-72-4">33708-72-4</a><span class="editoronly" style="display:none;"></span>
</td>
<td>OCH<sub>3</sub>
</td>
<td>OH
</td>
<td>H
</td>
<td>OCH<sub>3</sub>
</td>
<td>H
</td>
<td>H
</td>
<td>OCH<sub>3</sub>
</td>
<td>OH
</td>
<td>H
</td>
<td>H
</td></tr>
<tr>
<td><b><a href="Quercetin" title="Quercetin">Quercetin</a></b>
</td>
<td><span title="Untervorlage eingebunden: CASRN"></span><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=117-39-5">117-39-5</a><span class="editoronly" style="display:none;"></span>
</td>
<td>OH
</td>
<td>OH
</td>
<td>H
</td>
<td>OH
</td>
<td>H
</td>
<td>H
</td>
<td>OH
</td>
<td>OH
</td>
<td>H
</td>
<td>H
</td></tr>
<tr>
<td>Rhamnazin
</td>
<td><span title="Untervorlage eingebunden: CASRN"></span><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=552-54-5">552-54-5</a><span class="editoronly" style="display:none;"></span>
</td>
<td>OH
</td>
<td>OH
</td>
<td>H
</td>
<td>OCH<sub>3</sub>
</td>
<td>H
</td>
<td>H
</td>
<td>OCH<sub>3</sub>
</td>
<td>OH
</td>
<td>H
</td>
<td>H
</td></tr>
<tr>
<td><a href="Rhamnetin" title="Rhamnetin">Rhamnetin</a>
</td>
<td><span title="Untervorlage eingebunden: CASRN"></span><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=90-19-7">90-19-7</a><span class="editoronly" style="display:none;"></span>
</td>
<td>OH
</td>
<td>OH
</td>
<td>H
</td>
<td>OCH<sub>3</sub>
</td>
<td>H
</td>
<td>H
</td>
<td>OH
</td>
<td>OH
</td>
<td>H
</td>
<td>H
</td></tr>
<tr>
<td>Robinetin
</td>
<td><span title="Untervorlage eingebunden: CASRN"></span><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=490-31-3">490-31-3</a><span class="editoronly" style="display:none;"></span>
</td>
<td>OH
</td>
<td>H
</td>
<td>H
</td>
<td>OH
</td>
<td>H
</td>
<td>H
</td>
<td>OH
</td>
<td>OH
</td>
<td>OH
</td>
<td>H
</td></tr></tbody></table>
<div class="mw-heading mw-heading2"><h2 id="Glycosylierte_Flavonole">Glycosylierte Flavonole</h2></div>
<p>Häufig kommen die Flavonole nicht in freier Form, sondern als <a href="Glycoside" title="Glycoside">Glycoside</a> vor. Die Anbindung der Zucker erfolgt hauptsächlich über die Hydroxygruppe in der 3-Position. Deutlich weniger häufig ist die Anbindung von Zuckern über die Position 7 und selten über die Positionen 4', 3' oder 5.<sup id="cite_ref-Herrmann_2-2" class="reference"><a href="#cite_note-Herrmann-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> Bei der Anbindung von zwei Zuckereinheiten ist die Anbindung eines Disaccharids über die Position 3 am häufigsten (vgl. z. B. <a href="Rutin" title="Rutin">Rutin</a>) gefolgt von der Anbindung von zwei Monosacchariden über die Positionen 3 und 7.<sup id="cite_ref-Herrmann_2-3" class="reference"><a href="#cite_note-Herrmann-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup>
</p>
<table class="wikitable">
<caption>Beispiele für Glycoside der Flavonole
</caption>
<tbody><tr>
<th>Glycosid</th>
<th>Aglycon</th>
<th>3</th>
<th>5</th>
<th>6</th>
<th>7</th>
<th>8</th>
<th>2′</th>
<th>3′</th>
<th>4′</th>
<th>5′</th>
<th>6′</th>
<th>CAS
</th></tr>
<tr>
<td><a href="Astragalin" title="Astragalin">Astragalin</a></td>
<td><a href="Kaempferol" title="Kaempferol">Kaempferol</a></td>
<td><b>Glc</b></td>
<td>OH</td>
<td></td>
<td>OH</td>
<td></td>
<td></td>
<td></td>
<td>OH</td>
<td></td>
<td></td>
<td><span title="Untervorlage eingebunden: CASRN"></span><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=480-10-4">480-10-4</a><span class="editoronly" style="display:none;"></span>
</td></tr>
<tr>
<td><a href="Azalein_(Flavonoid)" title="Azalein (Flavonoid)">Azalein</a></td>
<td>Azaleatin</td>
<td><b>Rha</b></td>
<td>OCH<sub>3</sub></td>
<td></td>
<td>OH</td>
<td></td>
<td></td>
<td>OH</td>
<td>OH</td>
<td></td>
<td></td>
<td><span title="Untervorlage eingebunden: CASRN"></span><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=29028-02-2">29028-02-2</a><span class="editoronly" style="display:none;"></span>
</td></tr>
<tr>
<td><a href="Hyperosid" title="Hyperosid">Hyperosid</a></td>
<td><a href="Quercetin" title="Quercetin">Quercetin</a></td>
<td><b>Gal</b></td>
<td>OH</td>
<td></td>
<td>OH</td>
<td></td>
<td></td>
<td>OH</td>
<td>OH</td>
<td></td>
<td></td>
<td><span title="Untervorlage eingebunden: CASRN"></span><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=482-36-0">482-36-0</a><span class="editoronly" style="display:none;"></span>
</td></tr>
<tr>
<td>Isoquercetin</td>
<td><a href="Quercetin" title="Quercetin">Quercetin</a></td>
<td><b>Glc</b></td>
<td>OH</td>
<td></td>
<td>OH</td>
<td></td>
<td></td>
<td>OH</td>
<td>OH</td>
<td></td>
<td></td>
<td><span title="Untervorlage eingebunden: CASRN"></span><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=482-35-9">482-35-9</a><span class="editoronly" style="display:none;"></span>
</td></tr>
<tr>
<td>Kaempferitrin</td>
<td><a href="Kaempferol" title="Kaempferol">Kaempferol</a></td>
<td><b>Rha</b></td>
<td>OH</td>
<td></td>
<td><b>Rha</b></td>
<td></td>
<td></td>
<td></td>
<td>OH</td>
<td></td>
<td></td>
<td><span title="Untervorlage eingebunden: CASRN"></span><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=482-38-2">482-38-2</a><span class="editoronly" style="display:none;"></span>
</td></tr>
<tr>
<td>Myricitrin</td>
<td><a href="Myricetin" title="Myricetin">Myricetin</a></td>
<td><b>Rha</b></td>
<td>OH</td>
<td></td>
<td>OH</td>
<td></td>
<td></td>
<td>OH</td>
<td>OH</td>
<td>OH</td>
<td></td>
<td><span title="Untervorlage eingebunden: CASRN"></span><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=17912-87-7">17912-87-7</a><span class="editoronly" style="display:none;"></span>
</td></tr>
<tr>
<td>Quercitrin</td>
<td><a href="Quercetin" title="Quercetin">Quercetin</a></td>
<td><b>Rha</b></td>
<td>OH</td>
<td></td>
<td>OH</td>
<td></td>
<td></td>
<td>OH</td>
<td>OH</td>
<td></td>
<td></td>
<td><span title="Untervorlage eingebunden: CASRN"></span><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=522-12-3">522-12-3</a><span class="editoronly" style="display:none;"></span>
</td></tr>
<tr>
<td>Robinin</td>
<td><a href="Kaempferol" title="Kaempferol">Kaempferol</a></td>
<td><b>Robinosyl</b></td>
<td>OH</td>
<td></td>
<td><b>Rha</b></td>
<td></td>
<td></td>
<td></td>
<td>OH</td>
<td></td>
<td></td>
<td><span title="Untervorlage eingebunden: CASRN"></span><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=301-19-9">301-19-9</a><span class="editoronly" style="display:none;"></span>
</td></tr>
<tr>
<td><a href="Rutin" title="Rutin">Rutin</a></td>
<td><a href="Quercetin" title="Quercetin">Quercetin</a></td>
<td><b>Rutinosyl</b></td>
<td>OH</td>
<td></td>
<td>OH</td>
<td></td>
<td></td>
<td>OH</td>
<td>OH</td>
<td></td>
<td></td>
<td><span title="Untervorlage eingebunden: CASRN"></span><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=153-18-4">153-18-4</a><span class="editoronly" style="display:none;"></span>
</td></tr>
<tr>
<td>Spiraeosid</td>
<td><a href="Quercetin" title="Quercetin">Quercetin</a></td>
<td>OH</td>
<td>OH</td>
<td></td>
<td>OH</td>
<td></td>
<td></td>
<td>OH</td>
<td><b>Glc</b></td>
<td></td>
<td></td>
<td><span title="Untervorlage eingebunden: CASRN"></span><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=20229-56-5">20229-56-5</a><span class="editoronly" style="display:none;"></span>
</td></tr>
<tr>
<th colspan="13" style="text-align:left; font-size: 90%; font-weight:normal">
<dl><dt>Legende zur Tabelle</dt></dl>
<p><a href="Glucose" title="Glucose">Glc</a> = β-D-Glucopyranosyloxy,<br><a href="Rhamnose" title="Rhamnose">Rha</a> = α-L-Rhamnopyranosyloxy,<br><a href="Galactose" title="Galactose">Gal</a> = β-D-Galactopyranosyloxy,<br>Robinosyl = α-L-Rhamnopyranosyl-(1→6)-β-D-galactopyranosyloxy,<br><a href="Rutinose" title="Rutinose">Rutinosyl</a> = α-L-Rhamnopyranosyl-(1→6)-β-D-glucopyranosyloxy
</p>
</th></tr></tbody></table>
<div class="mw-heading mw-heading2"><h2 id="Eigenschaften">Eigenschaften</h2></div>
<p>Die Flavonole besitzen zum Teil stark antioxidative Eigenschaften. Besonders Flavonole mit benachbarten Hydroxygruppen am B-Ring wirken antioxidativ. So besitzt Quercetin mit benachbarten OH-Gruppen in Position 3' und 4' eine <a href="Catechol" class="mw-redirect" title="Catechol">Catechol</a>-Struktureinheit und Myrecitin mit benachbarten OH-Gruppen in Position 3', 4' und 5' eine <a href="Pyrogallol" class="mw-redirect" title="Pyrogallol">Pyrogallol</a>-Struktureinheit, die jeweils leicht oxidierbar sind. Kaempferol mit einer einzelnen Hydroxygruppe in Position 4' des B-Rings wirkt dagegen weniger antioxidativ.<sup id="cite_ref-Terao_3-0" class="reference"><a href="#cite_note-Terao-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup>
</p>
<div class="mw-heading mw-heading2"><h2 id="Biosynthese">Biosynthese</h2></div>
<p>Die Biosynthese der Flavonole erfolgt durch Dehydrierung der entsprechenden Flavanole (Dihydroflavonole) unter Bildung der CC-Doppelbindung zwischen den Kohlenstoffatomen C2 und C3. Die Reaktion wird durch Enzyme aus der Gruppe der Flavonol-Synthasen katalysiert.<sup id="cite_ref-Nuhn_1-1" class="reference"><a href="#cite_note-Nuhn-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>
</p>
<div class="mw-heading mw-heading2"><h2 id="Synthese">Synthese</h2></div>
<p>Bereits 1908 entdeckte <a href="Karl_Friedrich_von_Auwers" class="mw-redirect" title="Karl Friedrich von Auwers">Karl von Auwers</a> durch Zufall die später nach ihm benannte <a href="Auwers-Synthese" title="Auwers-Synthese">Auwers-Synthese</a> mit der sich ausgehend von 3-Cumaranonen in einer Ringerweiterungsreaktion Flavonole herstellen lassen.
</p>
<p>Die <a href="Algar-Flynn-Oyamada-Reaktion" title="Algar-Flynn-Oyamada-Reaktion">Algar-Flynn-Oyamada-Reaktion</a> ist eine basenkatalysierte Ringschlussreaktion mit Wasserstoffperoxid, mit der ebenfalls Flavonole hergestellt werden können.
</p>
<div class="mw-heading mw-heading2"><h2 id="Einzelnachweise">Einzelnachweise</h2></div>
<ol class="references">
<li id="cite_note-Nuhn-1"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-Nuhn_1-0">a</a></sup> <sup><a href="#cite_ref-Nuhn_1-1">b</a></sup></span> <span class="reference-text">Peter Nuhn: <cite style="font-style:italic">Naturstoffchemie</cite>. 3. Auflage. S. Hirzel, Stuttgart/Leipzig 1997, ISBN 3-7776-0613-8, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>602–605</span>.<span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rfr_id=info:sid/de.wikipedia.org:Flavonole&rft.au=Peter+Nuhn&rft.btitle=Naturstoffchemie&rft.date=1997&rft.edition=3&rft.genre=book&rft.isbn=3777606138&rft.pages=602-605&rft.place=Stuttgart%2FLeipzig&rft.pub=S.+Hirzel" style="display:none"> </span></span>
</li>
<li id="cite_note-Herrmann-2"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-Herrmann_2-0">a</a></sup> <sup><a href="#cite_ref-Herrmann_2-1">b</a></sup> <sup><a href="#cite_ref-Herrmann_2-2">c</a></sup> <sup><a href="#cite_ref-Herrmann_2-3">d</a></sup></span> <span class="reference-text">Herrmann, K.: <i>Flavonols and flavones in food plants: a review</i>, International Journal of Food Science & Technology, 1976, 11(5), S. 433–448, <a href="Digital_Object_Identifier" title="Digital Object Identifier">doi</a>:<span class="uri-handle" style="white-space:nowrap"><a rel="nofollow" class="external text" href="https://doi.org/10.1111/j.1365-2621.1976.tb00743.x">10.1111/j.1365-2621.1976.tb00743.x</a></span> </span>
</li>
<li id="cite_note-Terao-3"><span class="mw-cite-backlink"><a href="#cite_ref-Terao_3-0">↑</a></span> <span class="reference-text">Terao, J.: <i>Flavonols: Metabolism, Bioavailability, and Health Impacts</i>, Chapter 8 in <i>Plant Phenolics and Human Health: Biochemistry, Nutrition, and Pharmacology</i>, Wiley-Online Library, 2009, S. 185–196, <a href="Digital_Object_Identifier" title="Digital Object Identifier">doi</a>:<span class="uri-handle" style="white-space:nowrap"><a rel="nofollow" class="external text" href="https://doi.org/10.1002/9780470531792.ch8">10.1002/9780470531792.ch8</a></span> </span>
</li>
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