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.
Subject(s)
Esters , Fish Oils , Phthalic Acids , Esterification , AntioxidantsABSTRACT
Multicomponent antioxidant mixture is proved to be highly effective in imparting oxidative stability to the edible oil. It is believed that the high efficacy of those mixtures is due to the synergistic effect exhibited by two or more components. The current study aims to analyse the synergistic effect of a flavonoid and its corresponding ester in improving the oxidative stability of n-3 PUFA rich sardine oil. The oxidative stability of rutin, esterified rutin and their combinations at three different concentrations was studied in sardine oil stored at 37 ºC for 12 days in contact with air under darkness. The combination of rutin and rutin ester showed maximum reduction of 54.2% in oxidation at 100 mg/kg and 150 mg/kg. Perhaps this is the first report on the synergistic effect of a flavonoid and its lipophilized ester for improving the oxidative stability of n-3 PUFA rich oil.
