RADICAL INTERMEDIATES AND ANTIOXIDANTS - AN ESR STUDY OF RADICALS FORMED ON CARNOSIC ACID IN THE PRESENCE OF OXIDIZED LIPIDS

Carnosic acid, an antioxidant extracted from rosemary, is shown to pro duce radicals when in contact with oxidized methyl oleate in the absen ce of air above 50 degrees C. Two radical species are formed: the firs t one, stable up to similar to 110 degrees C, is an hydroxy-phenoxy ra dical whose ESR spectrum was analyzed by studying its temperature depe ndence and its sensitivity to deuterium/proton exchange. The second sp ecies was observed above 110 degrees C, its ESR spectrum was identical to the spectrum obtained when carnosol, another antioxidant extracted from rosemary, was heated at the same temperature in the presence of oxidized lipid. This observation is probably due to the transformation of carnosic acid into carnosol; the analysis of the corresponding ESR spectrum suggests the formation of a keto phenoxy radical exhibiting a great delocalization of the unpaired electron.