Electrochemistry of Flavonoids

This review presents a description of the available data from the literature on the electrochemical properties of flavonoids. The emphasis has been placed on the mechanism of oxidation processes and an attempt was made to find a general relation between the observed reaction paths and the structure of flavonoids. Regardless of the solvent used, three potential regions related to flavonoid structures are characteristic of the occurrence of their electrochemical oxidation. The potential values depend on the solvent used. In the less positive potential region, flavonoids, which have an ortho dihydroxy moiety, are reversibly oxidized to corresponding o-quinones. The o-quinones, if they possess a C3 hydroxyl group, react with water to form a benzofuranone derivative (II). In the second potential region, (II) is irreversibly oxidized. In this potential region, some flavonoids without an ortho dihydroxy moiety can also be oxidized to the corresponding p-quinone methides. The oxidation of the hydroxyl groups located in ring A, which are not in the ortho position, occurs in the third potential region at the most positive values. Some discrepancies in the reported reaction mechanisms have been indicated, and this is a good starting point for further investigations.