Lipase-catalyzed synthesis of lipophilic phenolic antioxidants was carried out with a concentrate of n-3 polyunsaturated fatty acids (PUFAs), recovered from oil extracted from salmon ( Salmon salar ) byproduct. Vanillyl alcohol and rutin were selected for the esterification reaction, and obtained esters yields were 60 and 30%, respectively. The antioxidant activities of the esters were compared with those of commercial butylated hydroxytoluene (BHT) and α-tocopherol using DPPH radical scavenging and thiobarbituric acid assays. In the DPPH assay, rutin esters showed better activity than vanillyl esters, and on the contrary in lipophilic medium, vanillyl esters were found to be superior to rutin esters. In bulk oil system, the antioxidant activities of rutin and vanillyl derivatives were lower than that of BHT and α-tocopherol, but in emulsion, they showed better activity than α-tocopherol. By attaching to natural phenolics, the PUFAs are protected against oxidation, and PUFA improves the hydrophobicity of the phenolic, which could enhance its function in lipid systems.
An efficient synthetic method was developed for the preparation of 1-octacosanol (C 28 -alcohol) from commercially available lipid-based intermediates namely sebacic acid (decanedioic acid) and stearyl alcohol. The key step in the synthesis is the preparation of tert-butyl dimethyl octacos-10-enyloxy silane from 10-tert-butyl dimethyl silanyloxy decanal and octadecyl triphenylphosphonium bromide salt employing Witting reaction. This product on simultaneous hydrogenation of double bond and deprotection of tert-butyldimethylsilyl protecting group in a single step on treatment with Pd/C and H 2 in methanol at ambient temperature resulted octacosanol in 95% yields. The products were characterised by IR, 1 H NMR, and GC-MS analysis.
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