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Anthocyanidin - Wikipedia, the free encyclopedia

Anthocyanidin

From Wikipedia, the free encyclopedia

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.

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