1981•Journal of the American Oil Chemists SocietyRequires access

Antioxidant activity of amino acids bound to trolox‐C

Matthew Joseph Taylor, T. Richardson, Ronald D. Jasensky

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Abstract

Abstract Various amino acids, selected for their potential antioxidant activity, were, covalently attached to 6‐hydroxy‐2,5,7,8‐tetramethylchroman‐2‐carboxylic acid (Trolox‐C), a lower homolog of vitamin E that has great antioxidant effectiveness. The resulting Troloxylamino acids (T‐AA) had greater antioxidant effectiveness than Trolox‐C in a linoleate emulsion system oxidized by hemoglobin. Troloxyl‐tryptophan‐methyl ester and Troloxyl‐methionine‐methyl ester were the most effective T‐AA evaluated in the linoleate emulsion. However, butylated hydroxyanisole (BHA), butylated hydroxyanisole (BHA), butylated hydroxytoluene (BHT) and α‐tocopherol were more antioxidant than any T‐AA in the emulsion system. In a Schaal oven test at 45 C. Trolox‐C was by by far the most effective antioxidant evaluated in corn oil. BHT and Troloxylcysteine had significant antioxidant activity in corn oil, but no other T‐AA was antioxidant in corn oil. In butter oil, Trolox‐C again had the highest antioxidant activity, and BHA and BHT were also highly antioxidant. All t‐AA had antioxidant activity in butter oil, with Troloxyl‐methioninc and Troloxyl‐cysteine having the grcatest antioxidant effectiveness. The T‐AA of highest antioxidant activity were hydrolyzed by chymotrypsin and/or trypsin, in vitro.

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Abstract Various amino acids, selected for their potential antioxidant activity, were, covalently attached to 6‐hydroxy‐2,5,7,8‐tetramethylchroman‐2‐carboxylic acid (Trolox‐C), a lower homolog of vitamin E that has great antioxidant effectiveness. The resulting Troloxylamino acids (T‐AA) had greater antioxidant effectiveness than Trolox‐C in a linoleate emulsion system oxidized by hemoglobin. Troloxyl‐tryptophan‐methyl ester and Troloxyl‐methionine‐methyl ester were the most effective T‐AA evaluated in the linoleate emulsion. However, butylated hydroxyanisole (BHA), butylated hydroxyanisole (BHA), butylated hydroxytoluene (BHT) and α‐tocopherol were more antioxidant than any T‐AA in the emulsion system. In a Schaal oven test at 45 C. Trolox‐C was by by far the most effective antioxidant evaluated in corn oil. BHT and Troloxylcysteine had significant antioxidant activity in corn oil, but no other T‐AA was antioxidant in corn oil. In butter oil, Trolox‐C again had the highest antioxidant activity, and BHA and BHT were also highly antioxidant. All t‐AA had antioxidant activity in butter oil, with Troloxyl‐methioninc and Troloxyl‐cysteine having the grcatest antioxidant effectiveness. The T‐AA of highest antioxidant activity were hydrolyzed by chymotrypsin and/or trypsin, in vitro.

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Available abstract

Abstract Various amino acids, selected for their potential antioxidant activity, were, covalently attached to 6‐hydroxy‐2,5,7,8‐tetramethylchroman‐2‐carboxylic acid (Trolox‐C), a lower homolog of vitamin E that has great antioxidant effectiveness. The resulting Troloxylamino acids (T‐AA) had greater antioxidant effectiveness than Trolox‐C in a linoleate emulsion system oxidized by hemoglobin. Troloxyl‐tryptophan‐methyl ester and Troloxyl‐methionine‐methyl ester were the most effective T‐AA evaluated in the linoleate emulsion. However, butylated hydroxyanisole (BHA), butylated hydroxyanisole (BHA), butylated hydroxytoluene (BHT) and α‐tocopherol were more antioxidant than any T‐AA in the emulsion system. In a Schaal oven test at 45 C. Trolox‐C was by by far the most effective antioxidant evaluated in corn oil. BHT and Troloxylcysteine had significant antioxidant activity in corn oil, but no other T‐AA was antioxidant in corn oil. In butter oil, Trolox‐C again had the highest antioxidant activity, and BHA and BHT were also highly antioxidant. All t‐AA had antioxidant activity in butter oil, with Troloxyl‐methioninc and Troloxyl‐cysteine having the grcatest antioxidant effectiveness. The T‐AA of highest antioxidant activity were hydrolyzed by chymotrypsin and/or trypsin, in vitro.

Key concepts: Butylated hydroxyanisole, Trolox, Butylated hydroxytoluene, Antioxidant, Chemistry, Food science, Ethoxyquin, Organic chemistry

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