Kinetic study of the mechanism of free-radical scavenging action in curcumin: Effects of solvent and pH

A kinetic study was performed for the free-radical scavenging actions of curcumin and half-curcumin, which has a half-structure of curcumin, in order to clarify the mechanism of free-radical-scavenging in curcumin. The second-order rate constants for radical-scavenging reactions of curcumin and half-curcumin were measured by a stopped-flow spectrophotometer in several organic solvents (methanol, ethanol, acetonitrile, chloroform, and benzene) and in aqueous Triton X-100 (5.0 wt %) micelle solutions at various pH. The difference in the rate constant and solvent dependence between curcumin and half-curcumin suggests that the enol structure with the intramolecular hydrogen-bond of curcumin strongly enhances the radical-scavenging activity. Furthermore, notable pH dependences were observed for the rate constants of curcumin and half-curcumin in micelle solutions, suggesting that the acid-base dissociation equilibrium of phenol-protons in curcumin and half-curcumin affects their radical-scavenging activities. © 2005 The Chemical Society of Japan.