Conjugation Length Dependence of Free Radical Scavenging Efficiency of Retinal and Retinylisoflavonoid Homologues.

Retinal (C20) and the C25 and C30 homologues were compared as radical scavengers together with their C22, C27, and C32 homologues linked with daidzein through a B'3 (isoflavonoid) to oxo-carbon (aldehyde) covalent bond. Oxidation potential in acetonitrile determined by cyclic voltammetry and ionization potential calculated by density functional theory for the aldehydes and dyads (conjugates), of which the two longer are new, decreased linearly with the wavenumber for absorption maximum. The logarithm of the second-order rate constant for scavenging of the ABTS increased linearly with decreasing oxidation potential suggesting that longer conjugation in the antioxidant increases the rate of electron transfer.