Synthesis of Aliphatic Esters of Cinnamic Acid as Potential Lipophilic Antioxidants Catalyzed by Lipase B from Candida antarctica
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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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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 / catalysisSource:
Applied Biochemistry and Biotechnology, 2013, 170, 7, 1560-1573Publisher:
- Springer
Funding / projects:
DOI: 10.1007/s12010-013-0294-z
ISSN: 0273-2289 (Print); 1559-0291
WoS: 000322542900002
Scopus: 2-s2.0-84881231766
Institution/Community
Институт техничких наука САНУ / Institute of Technical Sciences of SASATY - 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 - https://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 UR - https://hdl.handle.net/21.15107/rcub_dais_355 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", 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", url = "https://hdl.handle.net/21.15107/rcub_dais_355" }
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. in Applied Biochemistry and Biotechnology Springer., 170(7), 1560-1573. https://doi.org/10.1007/s12010-013-0294-z https://hdl.handle.net/21.15107/rcub_dais_355
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. in Applied Biochemistry and Biotechnology. 2013;170(7):1560-1573. doi:10.1007/s12010-013-0294-z https://hdl.handle.net/21.15107/rcub_dais_355 .
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" in Applied Biochemistry and Biotechnology, 170, no. 7 (2013):1560-1573, https://doi.org/10.1007/s12010-013-0294-z ., https://hdl.handle.net/21.15107/rcub_dais_355 .