Covalent adduct formation and chloroform production after free radical attack on fatty acids by carbon tetrachloride reactive intermediates.
The interactions of fatty acids and the trichloromethyl free radical generated anaerobically by the benzoyl peroxide model system were studied. Chloroform was produced due to the interaction of the trichloromethyl free radical with the unsaturated fatty acid ester methyl oleate, indicating the hydrogen in chloroform may result from abstraction from fatty acids. In addition, chloroform was detected in incubations containing the saturated fatty acid ester methyl stearate, indicating hydrogen abstraction is not limited to allylic hydrogens. Mass spectral analysis identified one adduct resulting from additional reactions to methyl oleate, and an adduct resulting initially from hydrogen abstraction on methyl stearate. These findings describe previously unreported reactions of the trichloromethyl free radical with saturated fatty acid, and inhibition of chloroform production by 3 free radical inhibitors.
D001585:Benzoyl Peroxide; D002251:Carbon Tetrachloride; D002725:Chloroform; D004347:Drug Interactions; D005227:Fatty Acids; D005609:Free Radicals; D008401:Gas Chromatography-Mass Spectrometry; D008956:Models, Chemical
D005227:Fatty Acids; D005609:Free Radicals; D002725:Chloroform; D002251:Carbon Tetrachloride; D001585:Benzoyl Peroxide