Effect of Benzoic Acid and Some of Its Derivatives on the Rate of Dl-Dopa Oxidation by Mushroom Tyrosinase

This is the authors' abstract. We don't add key points for this paper.

Vanillic acid and salicylic acid inhibited the rate of dihydroxyphenylalanine (DL-DOPA) oxidation to dopachrome (γmax=475 nm) by tyrosinase at all concentrations tested. Benzoic acid and p-hydroxybenzoic acid (PHBA), at relatively low concentrations, slightly stimulated the rate of DL-DOPA oxidation, whereas at higher concentrations each inhibited the reaction. p-Hydroxybenzoic acid methyl ester (PHBAME), at relatively low concentrations, had a pronounced synergistic effect on the reaction, whereas at relatively high concentrations it inhibited the rate of DL-DOPA oxidation. The synergistic effect of 1.6–6.6 mM PHBAME on the rate of DL-DOPA oxidation to dopachrome was found to be only an apparent effect due to the ability of PHBAME to be hydroxylated very slowly by tyrosinase to a yellow pigmented product(s) with DL-DOPA serving as a reductant (AH2) for the hydroxylation reaction, thus hastening the conversion of PHBAME to pigmented product(s). Vanillic acid, salicylic acid, benzoic acid and PHBA could not be hydroxylated by tyrosinase.