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Arunachalam, Selva Sudha; Chandrasekar, Vaisali; Belur, Prasanna D.
Food chemistry, 05/2024, Letnik: 441Journal Article
Display omitted •Three esters of 3,4-dihydroxyphenylacetic acid (DHPA) were synthesized.•Binary solvent system with Amberlyst-15 was used to synthesize esters.•Esters were subjected to In vitro antioxidant assays and oil storage study.•Methyl ester showed higher efficacy relative to butyl and hexyl esters in bulk oil.•Esters performance in bulk oil system was compliant with polar paradox theory. Lipophilization of natural antioxidants is a proven strategy to enhance the solubility in bulk oil systems, thereby increasing their efficacy against oxidative degradation. This study aims to synthesize esters of 3,4-dihydroxyphenylacetic acid (3,4-DHPA) using Amberlyst-15 and to study the application of these esters in refined fish oil. Lipophilic esters were synthesized by esterification and transesterification of 3,4-DHPA in various solvent systems. Esters of methanol, butanol and hexanol were obtained with percent conversion of 81.1, 69.3 and 78.8 respectively, and were subjected to molecular characterization and in vitro oxidant assays. The 3,4-DHPA and its methyl ester showed 36% reduction in the TOTOX value over 30 days of storage. The length of the acyl chain in the ester was found to exert a high influence on its efficacy and lipophilicity. This is the first report of 3,4-DHPA and its lipophilic esters studied for enhancing the oxidative stability of fish oil.
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