Oxidation reactions of 1,3-diphenylpropane-1,3-dione

摘要

The free radical scavenging properties and possible antioxidant activity of 1,3-diphenylpropane-1,3-dione (1) are reported. Pulse radiolysis technique was employed to study the one-electron oxidation of 1 with various radicals viz. CCl3O$_{2}^{ullet}$, N$_{3}^{ullet}$ and ${}^{ullet}$OH in homogeneous aqueous solution. All these radicals reacted with 1 under ambient conditions at almost diffusion controlled rates producing transient species with an absorption maximum around 420 nm that decayed at first order rates. The transient absorption peak was shifted in the case of CCl3OO$^{ullet}$ radical reaction with 1 due to change in the polarity of the medium. Formation of a stable product with a broad absorption band starting from 400 nm and cut off at 230 nm was observed in the oxidation of 1 with ${}^{ullet}$OH and ${}^{ullet}$N3 radicals. In a biological system also, 1 showed significant inhibitory activity against Fe2+-mediated lipid peroxidation. Based on these observations, a suitable mechanism for the oxidation of 1 has been proposed.