Enzymatic lipophilization of vitamin C with linoleic acid: Determination of antioxidant and diffusion properties of L-ascorbyl linoleate

Abstract

Lipophilic derivatives of vitamin C are additives with antioxidant properties, attractive for application in food, cosmetics and pharmaceutics. They could be synthesized in lipase-catalyzed processes by using various acyl donors. Hereby, we present application of linoleic acid, which is polyunsaturated fatty acid essential in human nutrition, for esterification of vitamin C catalyzed by immobilized enzyme preparation Novozym ® 435 in acetone. Highest specific ester yield, 9.7 mmol/g of immobilized lipase, was accomplished with 0.15 M of vitamin C, 0.6 M of linoleic acid, 3 g/l of enzyme and 0.07% (v/v) of water, at 60 °C. NMR analyses of purified product proved that synthesized molecule was identical to 6-O-ascorbyl linoleate. Capacity of ester for scavenging 2,2-diphenyl-1-picrylhydrazyl radicals was two times higher comparing to parent molecule, vitamin C. Its diffusion coefficient, determined using Franz cell and cellulose acetate membrane, was 40% higher than palmitate and 62% higher than oleate. Obtained results showed that L-ascorbyl linoleate could be successfully synthesized in biocatalyzed processes. Furthermore, it was demonstrated that it possess high potential for application in different lipophilic products due to its liposolubility, high antioxidant efficiency and good diffusion properties.