Chromatographic behaviour of some stereochemically interrelated flavonoid compounds in aqueous medium

Abstract

Factors affecting the chromatographic behaviour of some flavonoid compounds in aqueous medium may be evaluated more accurately now that their stereochemical interrelationships have been established. The effect of the following factors on R F have been examined: (a) the separation of enantiomorphous flavan-3-ols, flavan-3,4-diols and 2,3-dihydroflavonols; (b) the cis- trans relationship of substituents in the heterocyclic ring of flavan-3-ols, (c) the introduction of a carbonyl group in the 4-position, hydroxyl groups in the 4, 5 and 5′-positions, and a galloyl group in the 3-position. The zero R F of flavonoid compounds of planar structure is likely to be due to their low solubility in water. Solubility appears to be one of the predominant factors affecting the R F of flavonoid compounds in aqueous medium.