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

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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.

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Acknowledgments

This work was supported by grant numbers E!6750 and III 46010 from the Ministry of Education, Science and Technological Development, Republic of Serbia.

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Authors and Affiliations

  1. Faculty of Technology and Metallurgy, University of Belgrade, Karnegijeva 4, 11001, Belgrade, Serbia

    Sonja M. Jakovetić, Milica M. Gvozdenović, Dejan I. Bezbradica, Dušan Ž. Mijin & Zorica D. Knežević-Jugović

  2. Institute of Technical Science, Serbian Academy of Science and Arts, Knez Mihajlova 35, 11000, Belgrade, Serbia

    Branimir Z. Jugović

  3. Faculty of Technology, University of Novi Sad, Blvd Cara Lazara 1, Novi Sad, Serbia

    Mirjana G. Antov

  4. Department of Biochemical Engineering and Biotechnology, Faculty of Technology and Metallurgy, University of Belgrade, Karnegijeva 4, 11001, Belgrade, Serbia

    Zorica D. Knežević-Jugović

Authors
  1. Sonja M. Jakovetić
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  2. Branimir Z. Jugović
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  3. Milica M. Gvozdenović
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  4. Dejan I. Bezbradica
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  5. Mirjana G. Antov
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  6. Dušan Ž. Mijin
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  7. Zorica D. Knežević-Jugović
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Correspondence to Zorica D. Knežević-Jugović.

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Jakovetić, S.M., Jugović, B.Z., Gvozdenović, M.M. et al. Synthesis of Aliphatic Esters of Cinnamic Acid as Potential Lipophilic Antioxidants Catalyzed by Lipase B from Candida antarctica . Appl Biochem Biotechnol 170, 1560–1573 (2013). https://doi.org/10.1007/s12010-013-0294-z

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  • DOI: https://doi.org/10.1007/s12010-013-0294-z

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