title: Synthesis of aliphatic esters of cinnamic acid as potential lipophilic antioxidants catalyzed by lipase B from Candida antarctica.
abstract: Immobilized lipase from Candida antarctica (Novozyme 435) was tested for the synthesis of various phenolic acid esters (ethyl and n-butyl cinnamate, ethyl p-coumarate and n-butyl p-methoxycinnamate). The second-order kinetic model was used to mathematically describe the reaction kinetics and to compare present processes quantitatively. It was found that the model agreed well with the experimental data. Further, the effect of alcohol type on the esterification of cinnamic acid was investigated. The immobilized lipase showed more ability to catalyze the synthesis of butyl cinnamate. Therefore, the process was optimized for the synthesis of butyl cinnamate as a function of solvent polarity (logP) and amount of biocatalyst. The highest ester yield of 60.7 % was obtained for the highest enzyme concentration tested (3 % w/w), but the productivity was for 34 % lower than the corresponding value obtained for the enzyme concentration of 1 % (w/w). The synthesized esters were purified, identified, and screened for antioxidant activities. Both DPPH assay and cyclic voltammetry measurement have shown that cinnamic acid esters have better antioxidant properties than cinnamic acid itself.
authors.affiliation: Faculty of Technology and Metallurgy, University of Belgrade, Karnegijeva 4, 11001 Belgrade, Serbia.
authors.forename: Sonja M
authors.initials: SM
authors.lastname: Jakovetić
authors.forename: Branimir Z
authors.initials: BZ
authors.lastname: Jugović
authors.forename: Milica M
authors.initials: MM
authors.lastname: Gvozdenović
authors.forename: Dejan I
authors.initials: DI
authors.lastname: Bezbradica
authors.forename: Mirjana G
authors.initials: MG
authors.lastname: Antov
authors.forename: Dušan Z
authors.initials: DZ
authors.lastname: Mijin
authors.forename: Zorica D
authors.initials: ZD
authors.lastname: Knežević-Jugović
mesh_terms: D000975:Antioxidants / Q000138:chemical synthesis*; D002934:Cinnamates / Q000737:chemistry*; D003198:Computer Simulation; D004800:Enzymes, Immobilized / Q000737:chemistry; D005227:Fatty Acids / Q000138:chemical synthesis*; D005240:Feasibility Studies; D005656:Fungal Proteins / Q000737:chemistry*; D008049:Lipase / Q000737:chemistry*; D008055:Lipids / Q000138:chemical synthesis*; D008956:Models, Chemical
chemical_list: D000975:Antioxidants; D002934:Cinnamates; D004800:Enzymes, Immobilized; D005227:Fatty Acids; D005656:Fungal Proteins; D008055:Lipids; C029010:cinnamic acid; D008049:Lipase; C431349:lipase B, Candida antarctica