Anthocyanidin

<h2 id="classification">Classification</h2>
<p><a href="/facts/3-Deoxyanthocyanidin/YowwKQ8o">3-Deoxyanthocyanidins</a> such as <a href="/facts/Luteolinidin/L5R9FfUY">luteolinidin</a> are a class of anthocyanidins lacking an hydroxyl group on carbon 3.
</p>
Selected anthocyanidins and their substitutions<table><tbody><tr><th>Anthocyanidin</th><th>Basic structure (R3 & R4′ = −OH)</th><th>R3′</th><th>R5′</th><th>R5</th><th>R6</th><th>R7</th></tr><tr><td><a href="/facts/Aurantinidin/qyXo7HUI">Aurantinidin</a></td><td rowspan="12"></td><td>−H</td><td>−H</td><td>−OH</td><td>−OH</td><td>−OH</td></tr><tr><td><a href="/facts/Capensinidin/HBv3SPes">Capensinidin</a></td><td>−OCH3</td><td>−OCH3</td><td>−OCH3</td><td>−H</td><td>−OH</td></tr><tr><td><a href="/facts/Cyanidin/AhwFgtq1">Cyanidin</a></td><td>−OH</td><td>−H</td><td>−OH</td><td>−H</td><td>−OH</td></tr><tr><td><a href="/facts/Delphinidin/BS8sklyj">Delphinidin</a></td><td>−OH</td><td>−OH</td><td>−OH</td><td>−H</td><td>−OH</td></tr><tr><td><a href="/facts/Europinidin/IWtBA7X4">Europinidin</a></td><td>−OCH3</td><td>−OH</td><td>−OCH3</td><td>−H</td><td>−OH</td></tr><tr><td><a href="/facts/Hirsutidin/fXGVgdPt">Hirsutidin</a></td><td>−OCH3</td><td>−OCH3</td><td>−OH</td><td>−H</td><td>−OCH3</td></tr><tr><td><a href="/facts/Malvidin/az2VBexe">Malvidin</a></td><td>−OCH3</td><td>−OCH3</td><td>−OH</td><td>−H</td><td>−OH</td></tr><tr><td><a href="/facts/Pelargonidin/Fq22s9QQ">Pelargonidin</a></td><td>−H</td><td>−H</td><td>−OH</td><td>−H</td><td>−OH</td></tr><tr><td><a href="/facts/Peonidin/DPGtYGrd">Peonidin</a></td><td>−OCH3</td><td>−H</td><td>−OH</td><td>−H</td><td>−OH</td></tr><tr><td><a href="/facts/Petunidin/U6t2xlpN">Petunidin</a></td><td>−OH</td><td>−OCH3</td><td>−OH</td><td>−H</td><td>−OH</td></tr><tr><td><a href="/facts/Pulchellidin/R19YPIhI">Pulchellidin</a></td><td>−OH</td><td>−OH</td><td>−OCH3</td><td>−H</td><td>−OH</td></tr><tr><td><a href="/facts/Rosinidin/ySQyQ2nG">Rosinidin</a></td><td>−OCH3</td><td>−H</td><td>−OH</td><td>−H</td><td>−OCH3</td></tr></tbody></table>
<h2 id="natural-occurrence">Natural occurrence</h2>
<p>Most plant anthocyanins are based on cyanidin (30%), delphinidin (22%), and pelargonidin (18%), respectively. Altogether 20% of the anthocyanins are based on the three common anthocyanidins (peonidin, malvidin, and petunidin) that are methylated.
</p><p>Around 3%, 3%, and 2% of the anthocyanins or anthocyanidins are respectively labeled as 3-desoxyanthocyanidins, rare methylated anthocyanidins, and 6-hydroxyanthocyanidins, respectively.
</p><p>In bryophytes, anthocyanins are usually based on 3-desoxyanthocyanidins located in the cell wall. A new anthocyanidin, riccionidin A, has been isolated from the liverwort <i><a href="/facts/Ricciocarpos_natans/xbGHK3jv">Ricciocarpos natans</a></i>. It could be derived from 6,7,2′,4′,6′-pentahydroxyflavylium, having undergone ring closure of the 6’ -hydroxyl at the 3-position. Its visible spectrum in <a href="/facts/Methanol/EIfpoNCg">methanolic</a> HCl is at 494 nm. This pigment was accompanied by riccionidin B, which most probably is based on two molecules of riccionidin A linked via the 3′- or 5′-positions. Both pigments were also detected in the liverworts <i>Marchantia polymorpha</i>, <i>Riccia duplex</i>, and <i>Scapania undulata</i>.<a class="footnote-ref" id="fnref:2" href="#fn:2"><sup>2</sup></a>
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<h2 id="effect-of-ph">Effect of pH</h2>
<p>The stability of anthocyanidins is dependent on <a href="/facts/PH/RnSv8D7y">pH</a>. At a low pH (acidic conditions), colored anthocyanidins are present, whereas at a higher pH (basic conditions) the colorless <a href="/facts/Chalcones/UGo4KFQU">chalcones</a> forms are present.
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<h2 id="external-links">External links</h2>
<ul><li> Media related to Anthocyanidins at Wikimedia Commons</li></ul>

<h2 id="references">References</h2>

<ol>
<li id="fn:1"><p>IUPAC Goldbook <a href="http://goldbook.iupac.org/A00379.html" target="_blank">http://goldbook.iupac.org/A00379.html</a> <a href="#fnref:1" class="footnote-back-ref">↩</a></p></li>
<li id="fn:2"><p>Flavonoids : chemistry, biochemistry, and applications. Andersen, Øyvind M., Markham, Kenneth R. CRC, Taylor & Francis. 2006. ISBN 0849320216. OCLC 60454800.{{cite book}}:  CS1 maint: others (link) <a href="0849320216" target="_blank">0849320216</a> <a href="#fnref:2" class="footnote-back-ref">↩</a></p></li>
</ol>

Anthocyanidin open-in-new

Anthocyanidin