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

Authorized Users Only
2013
Authors
Jakovetić, Sonja
Jugović, Branimir
Gvozdenović, Milica M.
Bezbradica, Dejan
Antov, Mirjana
Mijin, Dušan
Knežević Jugović, Zorica
Article (Published version)
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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, identifie...d, 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:
aliphatic esters / cinnamic acid / lipophilic antioxidants / Candida antarctica / lipase B / catalysis
Source:
Applied Biochemistry and Biotechnology, 2013, 170, 7, 1560-1573
Publisher:
  • Springer
Projects:
  • Novel encapsulation and enzyme technologies for designing of new biocatalysts and biologically active compounds targeting enhancement of food quality, safety and competitiveness (RS-46010)

DOI: 10.1007/s12010-013-0294-z

ISSN: 0273-2289 (Print); 1559-0291 (Online)

WoS: 000322542900002

Scopus: 2-s2.0-84881231766
[ Google Scholar ]
34
30
URI
http://dais.sanu.ac.rs/123456789/355
Collections
  • ITN SANU - Opšta kolekcija / ITS SASA - General collection
Institution
Институт техничких наука САНУ / Institute of Technical Sciences of SASA
TY  - JOUR
AU  - Jakovetić, Sonja
AU  - Jugović, Branimir
AU  - Gvozdenović, Milica M.
AU  - Bezbradica, Dejan
AU  - Antov, Mirjana
AU  - Mijin, Dušan
AU  - Knežević Jugović, Zorica
PY  - 2013
UR  - http://dais.sanu.ac.rs/123456789/355
AB  - 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.
PB  - Springer
T2  - Applied Biochemistry and Biotechnology
T1  - Synthesis of Aliphatic Esters of Cinnamic Acid as Potential Lipophilic Antioxidants Catalyzed by Lipase B from Candida antarctica
SP  - 1560
EP  - 1573
VL  - 170
IS  - 7
DO  - 10.1007/s12010-013-0294-z
ER  - 
@article{
author = "Jakovetić, Sonja and Jugović, Branimir and Gvozdenović, Milica M. and Bezbradica, Dejan and Antov, Mirjana and Mijin, Dušan and Knežević Jugović, Zorica",
year = "2013",
url = "http://dais.sanu.ac.rs/123456789/355",
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.",
publisher = "Springer",
journal = "Applied Biochemistry and Biotechnology",
title = "Synthesis of Aliphatic Esters of Cinnamic Acid as Potential Lipophilic Antioxidants Catalyzed by Lipase B from Candida antarctica",
pages = "1560-1573",
volume = "170",
number = "7",
doi = "10.1007/s12010-013-0294-z"
}
Jakovetić S, Jugović B, Gvozdenović MM, Bezbradica D, Antov M, Mijin D, Knežević Jugović Z. Synthesis of Aliphatic Esters of Cinnamic Acid as Potential Lipophilic Antioxidants Catalyzed by Lipase B from Candida antarctica. Applied Biochemistry and Biotechnology. 2013;170(7):1560-1573
Jakovetić, S., Jugović, B., Gvozdenović, M. M., Bezbradica, D., Antov, M., Mijin, D.,& Knežević Jugović, Z. (2013). Synthesis of Aliphatic Esters of Cinnamic Acid as Potential Lipophilic Antioxidants Catalyzed by Lipase B from Candida antarctica.
Applied Biochemistry and BiotechnologySpringer., 170(7), 1560-1573. 
https://doi.org/10.1007/s12010-013-0294-z
Jakovetić Sonja, Jugović Branimir, Gvozdenović Milica M., Bezbradica Dejan, Antov Mirjana, Mijin Dušan, Knežević Jugović Zorica, "Synthesis of Aliphatic Esters of Cinnamic Acid as Potential Lipophilic Antioxidants Catalyzed by Lipase B from Candida antarctica" 170, no. 7 (2013):1560-1573,
https://doi.org/10.1007/s12010-013-0294-z .

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