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 produce radicals when in contact with oxidized methyl oleate in the absence of air above 50 degrees C. Two radical species are formed: the first one, stable up to approximately 110 degrees C, is an hydroxy-phenoxy radical whose ESR spectrum was analyzed by studying its temperature dependence and its sensitivity to deuterium/proton exchange. The second species 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.
Geoffroy
M
M
Department of Physical Chemistry, University of Geneva, Switzerland.
Lambelet
P
P
Richert
P
P
D045784:Abietanes; D000975:Antioxidants / Q000737:chemistry*; D004224:Diterpenes / Q000737:chemistry*; D004578:Electron Spin Resonance Spectroscopy; D005609:Free Radicals; D008055:Lipids / Q000737:chemistry; D009829:Oleic Acids / Q000737:chemistry*; D010616:Phenanthrenes / Q000737:chemistry; D010936:Plant Extracts / Q000737:chemistry*; D017365:Spices
D045784:Abietanes; D000975:Antioxidants; D004224:Diterpenes; D005609:Free Radicals; D008055:Lipids; D009829:Oleic Acids; D010616:Phenanthrenes; D010936:Plant Extracts; C005576:methyl oleate; C068623:carnosol; C018381:salvin