Synthesis and characterization of 3,4-dihydroxyphenyl acetic acid esters and study of their efficacy in bulk fish oil

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dc.contributor.authorArunachalam, S.S.
dc.contributor.authorChandrasekar, V.
dc.contributor.authorBelur, P.D.
dc.date.accessioned2026-02-04T12:24:49Z
dc.date.issued2024
dc.description.abstractLipophilization 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
dc.identifier.citationFood Chemistry, 2024, 441, , pp. -
dc.identifier.issn3088146
dc.identifier.urihttps://doi.org/10.1016/j.foodchem.2024.138380
dc.identifier.urihttps://idr.nitk.ac.in/handle/123456789/21124
dc.publisherElsevier Ltd
dc.subjectAcetic acid
dc.subjectFish
dc.subjectPetroleum refining
dc.subjectpH
dc.subject3,4-dihydroxyphenyl acetic acid
dc.subjectAcid ester
dc.subjectAmberlyst-15
dc.subjectBulk oil systems
dc.subjectFish oil
dc.subjectLipophilization
dc.subjectNatural antioxidants
dc.subjectOxidative degradation
dc.subjectOxidative stability
dc.subjectSynthesis and characterizations
dc.subjectEsters
dc.subject3,4 dihydroxyphenylacetic acid
dc.subjectbutanol
dc.subjectfish oil
dc.subjecthexanol
dc.subjectmethanol
dc.subject3,4-dihydroxyphthalic acid
dc.subjectantioxidant
dc.subjectester
dc.subjectphthalic acid derivative
dc.subjectantioxidant activity
dc.subjectArticle
dc.subjectcontrolled study
dc.subjectesterification
dc.subjectferric reducing antioxidant power assay
dc.subjectin vitro study
dc.subjectlipophilicity
dc.subjectsynthesis
dc.subjecttransesterification
dc.subjectAntioxidants
dc.subjectEsterification
dc.subjectFish Oils
dc.subjectPhthalic Acids
dc.titleSynthesis and characterization of 3,4-dihydroxyphenyl acetic acid esters and study of their efficacy in bulk fish oil

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