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Issue 23, 2011
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Mechanism and kinetics studies on the antioxidant activity of sinapinic acid

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Abstract

The OOH radical scavenging activity of sinapinic acid (HSA) has been studied in aqueous and lipid solutions, using the Density Functional Theory. HSA is predicted to react about 32.6 times faster in aqueous solution than in lipid media. The overall rate coefficients are predicted to be 5.39 × 105 and 1.66 × 104 M−1 s−1, respectively. Branching ratios for the different channels of reaction are also reported for the first time, as well as the UV-Vis spectra of the main products of reaction. It was found that the reactivity of sinapinic acid towards OOH radicals takes place almost exclusively by H atom transfer from its phenolic moiety. However it was found to react via SET, at diffusion-limit controlled rate constants, with ˙OH, ˙OCCl3 and ˙OOCCl3 radicals. It was found that the polarity of the environment and the deprotonation of HSA in aqueous solution, both increase the reactivity of this compound towards peroxyl radicals.

Graphical abstract: Mechanism and kinetics studies on the antioxidant activity of sinapinic acid

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Article information


Submitted
11 Mar 2011
Accepted
12 Apr 2011
First published
13 May 2011

Phys. Chem. Chem. Phys., 2011,13, 11199-11205
Article type
Paper

Mechanism and kinetics studies on the antioxidant activity of sinapinic acid

A. Galano, M. Francisco-Márquez and J. R. Alvarez-Idaboy, Phys. Chem. Chem. Phys., 2011, 13, 11199
DOI: 10.1039/C1CP20722A

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