Anthocyanidin

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Benzopyrylium (chromenylium) salts with chloride as the counterion
Benzopyrylium (chromenylium) salts with chloride as the counterion
Not to be confused with Anthocyanin, their sugar containing counterparts.

Anthocyanidins are sugar-free counterparts of anthocyanins, can be identified based on the structure of a large group of polymethine dye, the benzopyrylium (chromenylium) ion. 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 anthocyanins differ from other flavonoids.

Molecule in 3D of the Cyanidin(2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-1-Benzopyrylium)
Molecule in 3D of the Cyanidin
(2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-1-Benzopyrylium)


Anthocyanidin R1 R2 R3 R4 R5 R6 R7
Aurantinidin -H -OH -H -OH -OH -OH -OH
Cyanidin -OH -OH -H -OH -OH -H -OH
Delphinidin -OH -OH -OH -OH -OH -H -OH
Europinidin -OCH3 -OH -OH -OH -OCH3 -H -OH
Luteolinidin -OH -OH -H -H -OH -H -OH
Pelargonidin -H -OH -H -OH -OH -H -OH
Malvidin -OCH3 -OH -OCH3 -OH -OH -H -OH
Peonidin -OCH3 -OH -H -OH -OH -H -OH
Petunidin -OH -OH -OCH3 -OH -OH -H -OH
Rosinidin -OCH3 -OH -H -OH -OH -H -OCH3
Anthocyanidin scaffold: the flavylium (2-phenylchromenylium) cation.
Anthocyanidin scaffold: the flavylium (2-phenylchromenylium) cation.