methyl-13-hydroperoxy-9-11-octadecadienoate and 6-hydroxy-2-5-7-8-tetramethylchroman-2-carboxylic-acid

To clarify the mechanisms of antioxidant action, the effect of alpha-tocopherol and its water-soluble carboxylic acid derivative, Trolox, was studied on the decomposition of methyl linoleate hydroperoxides (MeLoOOH). Decomposition rate and the distribution of autoxidation products formed from MeLoOOH were followed by analyzing the volatile and non-volatile products by static headspace gas chromatography and normal-phase high-performance liquid chromatography, respectively. Both alpha-tocopherol and Trolox markedly inhibited the decomposition of MeLoOOH in a concentration-dependent way. In the absence of antioxidants, MeLoOOH was completely decomposed after incubation for 48 h at 60 degrees C, and in the presence of equal molar concentration of antioxidants only 6-7% of initial MeLoOOH was decomposed even after 280 h of incubation. MeLoOOH produced 1.2% methyl linoleate hydroxy compounds (MeLoOOH) in the presence of alpha-tocopherol and 3.8% in the presence of Trolox. Both antioxidants inhibited the formation of volatile decomposition products and the formation of ketodiene compounds. The hydroxy compounds may be formed by the reaction of alkoxy radical and hydrogen donating antioxidants. Conversion of MeLoOOH into stable MeLoOH demonstrated that the antioxidants alpha-tocopherol and Trolox trap alkoxyl radicals by H-donation.

Topics: Antioxidants; Chromans; Chromatography, Gas; Chromatography, High Pressure Liquid; Kinetics; Lipid Peroxides; Structure-Activity Relationship; Time Factors; Vitamin E