1-Substituted pyrroles (1 and 2) and 1-substituted 2-(l'-hydroxypropyl)pyrroles (3)(4)(5) were produced in reactions between a lipid peroxidation product, 4,5(E)-epoxy-2(E)-heptenal, and the amino acid lysine. The antioxidative activity of compounds 1-5 was studied. Oxidative stability was evaluated in refined soybean oil containing compounds 1-5, buty[ated hydroxytoluene (BHT), n-propyl gallate or L-lysine, at concentrations of 50-200 ppm. Oils were either oxidized at 60°C and oxidation products determined by the thiobarbituric acid-reactive substances assay, or they were oxidized at 110°C by the Rancimat method. Although both methods gave similar results, greater differences were observed at 60°C than at 110°C. Addition of compounds 1-5, L-lysine, BHT, and propyl gaiiate significantly (P < 0.01) protected the oil against oxidation. The effectiveness order found was: L-lysine << compounds 3-4 < compounds 1-2 < compound 5 = BHT << propy [ gallate. JAOCS 72, 1571[ gallate. JAOCS 72, -1575[ gallate. JAOCS 72, (1995.