title: Influence of fatty acid on lipase-catalyzed synthesis of ascorbyl esters and their free radical scavenging capacity.
abstract: Fatty acid (FA) ascorbyl esters are recently emerging food, cosmetic, and pharmaceutical additives, which can be prepared in an eco-friendly way by using lipases as catalysts. Because they are amphiphilic molecules, which possess high free radical scavenging capacity, they can be applied as liposoluble antioxidants as well as emulsifiers and biosurfactants. In this study, the influence of a wide range of acyl donors on ester yield in lipase-catalyzed synthesis and ester antioxidant activity was examined. Among saturated acyl donors, higher yields and antioxidant activities of esters were achieved when short-chain FAs were used. Oleic acid gave the highest yield overall and its ester exhibited a high antioxidant activity. Optimization of experimental factors showed that the highest conversion (60.5%) in acetone was achieved with 5 g L(-1) of lipase, 50 mM of vitamin C, 10-fold molar excess of oleic acid, and 0.7 mL L(-1) of initial water. Obtained results showed that even short- and medium-chain ascorbyl esters could be synthesized with high yields and retained (or even exceeded) free radical scavenging capacity of l-ascorbic acid, indicating prospects of broadening their application in emulsions and liposomes.
authors.affiliation: Department of Biochemical Engineering and Biotechnology, Faculty of Technology and Metallurgy, University of Belgrade, Belgrade, Serbia.
authors.forename: Marija
authors.initials: M
authors.lastname: Stojanović
authors.affiliation: Department of Biochemical Engineering and Biotechnology, Faculty of Technology and Metallurgy, University of Belgrade, Belgrade, Serbia.
authors.forename: Milica
authors.initials: M
authors.lastname: Carević
authors.affiliation: Department of Biochemical Engineering and Biotechnology, Faculty of Technology and Metallurgy, University of Belgrade, Belgrade, Serbia.
authors.forename: Mladen
authors.initials: M
authors.lastname: Mihailović
authors.affiliation: Department of Biochemistry, Faculty of Chemistry, University of Belgrade, Belgrade, Serbia.
authors.forename: Dušan
authors.initials: D
authors.lastname: Veličković
authors.affiliation: Department of Biochemistry, Faculty of Chemistry, University of Belgrade, Belgrade, Serbia.
authors.forename: Aleksandra
authors.initials: A
authors.lastname: Dimitrijević
authors.affiliation: Department of Biochemistry, Faculty of Chemistry, University of Belgrade, Belgrade, Serbia.
authors.forename: Nenad
authors.initials: N
authors.lastname: Milosavić
authors.affiliation: Department of Biochemical Engineering and Biotechnology, Faculty of Technology and Metallurgy, University of Belgrade, Belgrade, Serbia.
authors.forename: Dejan
authors.initials: D
authors.lastname: Bezbradica
mesh_terms: D001205:Ascorbic Acid / Q000737:chemistry*; D002175:Candida / Q000201:enzymology*; D004800:Enzymes, Immobilized; D004952:Esters; D005227:Fatty Acids / Q000737:chemistry*; D016166:Free Radical Scavengers / Q000138:chemical synthesis* / Q000737:chemistry; D005656:Fungal Proteins / Q000737:chemistry*; D008049:Lipase / Q000737:chemistry*
chemical_list: D004800:Enzymes, Immobilized; D004952:Esters; D005227:Fatty Acids; D016166:Free Radical Scavengers; D005656:Fungal Proteins; C093667:Novozyme 435; D008049:Lipase; C431349:lipase B, Candida antarctica; D001205:Ascorbic Acid
keywords: Candida antarctica lipase B; antioxidant; ascorbyl ester; fatty acid; vitamin C