Applied Biochemistry and Biotechnology

, Volume 170, Issue 7, pp 1560–1573

Synthesis of Aliphatic Esters of Cinnamic Acid as Potential Lipophilic Antioxidants Catalyzed by Lipase B from Candida antarctica

  • Sonja M. Jakovetić
  • Branimir Z. Jugović
  • Milica M. Gvozdenović
  • Dejan I. Bezbradica
  • Mirjana G. Antov
  • Dušan Ž. Mijin
  • Zorica D. Knežević-Jugović
Article

DOI: 10.1007/s12010-013-0294-z

Cite this article as:
Jakovetić, S.M., Jugović, B.Z., Gvozdenović, M.M. et al. Appl Biochem Biotechnol (2013) 170: 1560. doi:10.1007/s12010-013-0294-z

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.

Keywords

Phenolic acid esters Enzymatic esterification Lipase B Kinetics Radical-scavenging activity Antioxidant activity Cyclic voltammetry 

Copyright information

© Springer Science+Business Media New York 2013

Authors and Affiliations

  • Sonja M. Jakovetić
    • 1
  • Branimir Z. Jugović
    • 2
  • Milica M. Gvozdenović
    • 1
  • Dejan I. Bezbradica
    • 1
  • Mirjana G. Antov
    • 3
  • Dušan Ž. Mijin
    • 1
  • Zorica D. Knežević-Jugović
    • 1
    • 4
  1. 1.Faculty of Technology and MetallurgyUniversity of BelgradeBelgradeSerbia
  2. 2.Institute of Technical ScienceSerbian Academy of Science and ArtsBelgradeSerbia
  3. 3.Faculty of TechnologyUniversity of Novi SadNovi SadSerbia
  4. 4.Department of Biochemical Engineering and Biotechnology, Faculty of Technology and MetallurgyUniversity of BelgradeBelgradeSerbia

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