Kinetic study of the radical scavenging of capsaicin in homogeneous solutions and aqueous Triton X-100 micellar suspensions.

Abstract

A kinetic study of capsaicin (CAP) toward radicals has been performed using stopped-flow spectrophotometry in detail. The second-order rate constants (k2) for the reaction of CAP toward 2,2-diphenyl-1-picrylhydrazyl (DPPH) and galvinoxyl have been measured in methanol, ethanol, 2-propanol/water (5:1, v/v), and aqueous micellar suspensions containing 5% Triton X-100 (pH 4.0 to 10.0), respectively. The decay rates of DPPH and galvinoxyl for the reaction with CAP increased linearly in a concentration-dependent manner in homogeneous solutions and aqueous micellar suspensions. However, the k2 for CAP obtained in an aqueous micellar suspension showed notable pH dependence; that is, the reactivity of CAP increased with an increasing pH value from 4 to 10. In addition, a good correlation between the k2 value and the molar fraction of CAP (phenolate anion (CAP-O(-))/undeprotonated form (CAP-OH)) was observed. These properties are associated with the pKa of CAP. Furthermore, it was found that the CAP-O(-) reacts with galvinoxyl about 6 times as fast as the CAP-OH. These results indicate that sequential proton loss electron transfer from the phenolic hydrogen of CAP may be responsible for the scavenging of radicals in an aqueous micellar suspensions.