PMID: 9433903Jan 20, 1998Paper

Oxidative decarboxylation of benzoic acid by peroxyl radicals

Free Radical Biology & Medicine
R LamriniJ L Brazier

Abstract

A chemical model based on the thermal decomposition of AAPH (2,2'-azobis(2-amidinopropane) dihydrochloride is used for the production of peroxyl radicals. Peroxyl radicals induces the decarboxylation of [7-13C]benzoic acid and the production of 13CO2, which is measured by gas chromatography-isotope ratio mass spectrometry (GC-IRMS). The decarboxylation depends on temperature, AAPH, and benzoic acid concentrations. The decarboxylation also depends on the presence of oxygen. Electron spin resonance studies are performed to confirm the presence of peroxyl radicals under oxygen and of carbon-centered radicals in the absence of oxygen. Decarboxylation rates are measured in the presence of various antioxidants: ascorbate, dimethylsulfoxide, mannitol, and uric acid. It turns out that the decarboxylation is inhibited by each of these antioxidants. The ratio of decarboxylation rates, with and without the antioxidant, varies linearly with the antioxidant concentration. HPLC and GC-MS analyses of reaction products between benzoic acid and AAPH-derived radicals do not detect the presence of radical substitution products on the aromatic ring or the products derived from benzoic acid. There is no doubt that GC-IRMS is a powerful technique to...Continue Reading

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Citations

Mar 8, 2000·Proceedings of the National Academy of Sciences of the United States of America·S A BennerD H Powell
Dec 11, 2008·Photochemistry and Photobiology·Pedro M David GaraDaniel O Mártire
Aug 26, 2004·Redox Report : Communications in Free Radical Research·Aneta BalcerczykGrzegorz Bartosz
Nov 10, 2010·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Yan GongShijie Liu
Mar 29, 2011·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Yan Gong, Lu Lin
Nov 21, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Marion L ChevallierGregory Chatel

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