Synthesis and characterization of 3,4-dihydroxyphenyl acetic acid esters and study of their efficacy in bulk fish oil
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Date
2024
Journal Title
Journal ISSN
Volume Title
Publisher
Elsevier Ltd
Abstract
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. © 2024 Elsevier Ltd
Description
Keywords
Acetic acid, Fish, Petroleum refining, pH, 3,4-dihydroxyphenyl acetic acid, Acid ester, Amberlyst-15, Bulk oil systems, Fish oil, Lipophilization, Natural antioxidants, Oxidative degradation, Oxidative stability, Synthesis and characterizations, Esters, 3,4 dihydroxyphenylacetic acid, butanol, fish oil, hexanol, methanol, 3,4-dihydroxyphthalic acid, antioxidant, ester, phthalic acid derivative, antioxidant activity, Article, controlled study, esterification, ferric reducing antioxidant power assay, in vitro study, lipophilicity, synthesis, transesterification, Antioxidants, Esterification, Fish Oils, Phthalic Acids
Citation
Food Chemistry, 2024, 441, , pp. -