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, SonjaJugović, Branimir
Gvozdenović, Milica
Bezbradica, Dejan
Antov, Mirjana
Mijin, Dušan
Knežević-Jugović, Zorica
Article (Published version)
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Show full item recordAbstract
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:
Phenolic acid esters / Enzymatic esterification / Lipase B / Kinetics / Radical-scavenging activity / Antioxidant activity / Cyclic voltammetrySource:
Applied Biochemistry and Biotechnology, 2013, 170, 7, 1560-1573Publisher:
- Springer, New York
Funding / projects:
- E!6750
- Novel encapsulation and enzyme technologies for designing of new biocatalysts and biologically active compounds targeting enhancement of food quality, safety and competitiveness (RS-MESTD-Integrated and Interdisciplinary Research (IIR or III)-46010)
DOI: 10.1007/s12010-013-0294-z
ISSN: 0273-2289
PubMed: 23703579
WoS: 000322542900002
Scopus: 2-s2.0-84881231766
Institution/Community
Tehnološko-metalurški fakultetTY - JOUR AU - Jakovetić, Sonja AU - Jugović, Branimir AU - Gvozdenović, Milica AU - Bezbradica, Dejan AU - Antov, Mirjana AU - Mijin, Dušan AU - Knežević-Jugović, Zorica PY - 2013 UR - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/2420 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, New York T2 - Applied Biochemistry and Biotechnology T1 - Synthesis of Aliphatic Esters of Cinnamic Acid as Potential Lipophilic Antioxidants Catalyzed by Lipase B from Candida antarctica EP - 1573 IS - 7 SP - 1560 VL - 170 DO - 10.1007/s12010-013-0294-z ER -
@article{ author = "Jakovetić, Sonja and Jugović, Branimir and Gvozdenović, Milica 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, New York", 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 = "1573-1560", number = "7", volume = "170", doi = "10.1007/s12010-013-0294-z" }
Jakovetić, S., Jugović, B., Gvozdenović, 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, New York., 170(7), 1560-1573. https://doi.org/10.1007/s12010-013-0294-z
Jakovetić S, Jugović B, Gvozdenović M, 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 .
Jakovetić, Sonja, Jugović, Branimir, Gvozdenović, Milica, 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 . .