Abstract
1-Substituted pyrroles (1 and2) and1-substituted 2-(1′-hydroxypropyl)pyrroles (3–5) 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 compounds1–5 was studied. Oxidative stability was evaluated in refined soybean oil containing compounds1–5, butylated hydroxytoluene (BHT),n-propyl gallate orl-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 compounds1–5,l-lysine, BHT, and propyl gallate significantly (P<0.01) protected the oil against oxidation. The effectiveness order found was:l-lysine << compounds3–4 < compounds1–2 < compound5 ≈ BHT << propyl gallate.
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Alaiz, M., Zamora, R. & Hidalgo, F.J. Natural antioxidants produced in oxidized lipid/amino acid browning reactions. J Am Oil Chem Soc 72, 1571–1575 (1995). https://doi.org/10.1007/BF02577856
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DOI: https://doi.org/10.1007/BF02577856