Anthocyanidin

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Not to be confused with anthocyanins, the sugar-containing counterparts of anthocyanidins.
Molecule in 3D of the anthocyanidin cyanidin

Anthocyanidins are common plant pigments. They are the sugar-free counterparts of anthocyanins based on the flavylium ion or 2-phenylchromenylium, which is a type of oxonium ion (chromenylium is referred also to as benzopyrylium).[1] They form a large group of polymethine dye. In particular anthocyanidins are salt derivatives of the 2-phenylchromenylium cation, also known as flavylium cation. As shown in the figure below, the phenyl group at the 2-position can carry different substituents. The counterion of the flavylium cation is mostly chloride. With this positive charge, the anthocyanidins differ from other flavonoids.

pH[edit]

The stability of anthocyanidins is dependent on pH. At a low pH (acidic conditions), colored anthocyanidins are present, whereas at a higher pH (basic conditions) the colorless chalcones forms are present.

Stability of anthocyanidins is dependent on pH.

Classification[edit]

3-Deoxyanthocyanidins such as luteolinidin are a class of anthocyanidins lacking an hydroxyl group on carbon 3.

Selected anthocyanidins and their substitutions
Anthocyanidin Basic structure (R4' = −OH) R3' R5' R3 R5 R6 R7
Aurantinidin Basic structure of Anthocyans: The flavio-cation −H −H −OH −OH −OH −OH
Capensinidin −OCH3 −OCH3 −OH −OCH3 −H −OH
Cyanidin −OH −H −OH −OH −H −OH
Delphinidin −OH −OH −OH −OH −H −OH
Europinidin −OCH3 −OH −OH −OCH3 −H −OH
Hirsutidin −OCH3 −OCH3 −OH −OH −H −OCH3
Malvidin −OCH3 −OCH3 −OH −OH −H −OH
Pelargonidin −H −H −OH −OH −H −OH
Peonidin −OCH3 −H −OH −OH −H −OH
Petunidin −OH −OCH3 −OH −OH −H −OH
Pulchellidin −OH −OH −OH −OCH3 −H −OH
Rosinidin −OCH3 −H −OH −OH −H −OCH3

References[edit]

External links[edit]

Media related to Anthocyanidins at Wikimedia Commons