Enzymatic Synthesis of Aliphatic Esters of Phenolic Acids and Evaluation of Their Antioxidant Properties

2012
Authors
Knežević Jugović, Zorica
Jakovetić, Sonja

Jugović, Branimir

Gvozdenović, Milica M.

Grbavčić, Sanja
Bezbradica, Dejan

Antov, Mirjana

Contributors
Markoš, JozefConference object (Published version)
Metadata
Show full item recordAbstract
The esterification activity of the commercial immobilized lipase CALB towards cinnamic acids and its derivative has been studied. Using cinnamic acid as substrate, the reaction rate constants (1.95 h-1 mM-1 for ethanol and 3.07 h-1 mM-1 for butanol) were more than four and nine times higher compared to those obtained with p-coumaric (0.47 h-1 mM-1) and p-methoxycinnamic acids (0.32 h-1 mM-1), respectively. Thus, esterification of cinnamic acid with ethanol by using C. antarctica lipase has selected as a model reaction for further study. Isooctane is shown to be the best solvent for this reaction even though solubility of cinnamic acid in this a polar solvent is very low. Highest esterification yield of ethyl cinnamate is obtained when initial molar ratio of substrates 1:3 (cinnamic acid is limiting substrate) is used. Esterification of cinnamic acid appeared to result in increasing radical-scavenging ability. The effect of esterification of cinnamic acid was also confirmed by electroch...emical method using ethyl cinnamate which appeared to enhance the antioxidant activity. These findings should stimulate the application of such lipase-catalyzed reactions for the preparation of food acceptable esters of cinnamic acid as potential lipophilic antioxidants.
Keywords:
phenolic acid esters / enzymatic esterification / ethyl cinnamate / Candida antarctica lipase / radical-scavenging activity / antioxidant activity / cyclic voltammetrySource:
Proceedings of the 39th International Conference of Slovak Society of Chemical Engineering, 2012, 1426-1432Publisher:
- Tatranské Matliare : Slovak Society of Chemical Engineering
Funding / projects:
Institution/Community
Институт техничких наука САНУ / Institute of Technical Sciences of SASATY - CONF AU - Knežević Jugović, Zorica AU - Jakovetić, Sonja AU - Jugović, Branimir AU - Gvozdenović, Milica M. AU - Grbavčić, Sanja AU - Bezbradica, Dejan AU - Antov, Mirjana PY - 2012 UR - https://dais.sanu.ac.rs/123456789/493 AB - The esterification activity of the commercial immobilized lipase CALB towards cinnamic acids and its derivative has been studied. Using cinnamic acid as substrate, the reaction rate constants (1.95 h-1 mM-1 for ethanol and 3.07 h-1 mM-1 for butanol) were more than four and nine times higher compared to those obtained with p-coumaric (0.47 h-1 mM-1) and p-methoxycinnamic acids (0.32 h-1 mM-1), respectively. Thus, esterification of cinnamic acid with ethanol by using C. antarctica lipase has selected as a model reaction for further study. Isooctane is shown to be the best solvent for this reaction even though solubility of cinnamic acid in this a polar solvent is very low. Highest esterification yield of ethyl cinnamate is obtained when initial molar ratio of substrates 1:3 (cinnamic acid is limiting substrate) is used. Esterification of cinnamic acid appeared to result in increasing radical-scavenging ability. The effect of esterification of cinnamic acid was also confirmed by electrochemical method using ethyl cinnamate which appeared to enhance the antioxidant activity. These findings should stimulate the application of such lipase-catalyzed reactions for the preparation of food acceptable esters of cinnamic acid as potential lipophilic antioxidants. PB - Tatranské Matliare : Slovak Society of Chemical Engineering C3 - Proceedings of the 39th International Conference of Slovak Society of Chemical Engineering T1 - Enzymatic Synthesis of Aliphatic Esters of Phenolic Acids and Evaluation of Their Antioxidant Properties SP - 1426 EP - 1432 UR - https://hdl.handle.net/21.15107/rcub_dais_493 ER -
@conference{ author = "Knežević Jugović, Zorica and Jakovetić, Sonja and Jugović, Branimir and Gvozdenović, Milica M. and Grbavčić, Sanja and Bezbradica, Dejan and Antov, Mirjana", year = "2012", abstract = "The esterification activity of the commercial immobilized lipase CALB towards cinnamic acids and its derivative has been studied. Using cinnamic acid as substrate, the reaction rate constants (1.95 h-1 mM-1 for ethanol and 3.07 h-1 mM-1 for butanol) were more than four and nine times higher compared to those obtained with p-coumaric (0.47 h-1 mM-1) and p-methoxycinnamic acids (0.32 h-1 mM-1), respectively. Thus, esterification of cinnamic acid with ethanol by using C. antarctica lipase has selected as a model reaction for further study. Isooctane is shown to be the best solvent for this reaction even though solubility of cinnamic acid in this a polar solvent is very low. Highest esterification yield of ethyl cinnamate is obtained when initial molar ratio of substrates 1:3 (cinnamic acid is limiting substrate) is used. Esterification of cinnamic acid appeared to result in increasing radical-scavenging ability. The effect of esterification of cinnamic acid was also confirmed by electrochemical method using ethyl cinnamate which appeared to enhance the antioxidant activity. These findings should stimulate the application of such lipase-catalyzed reactions for the preparation of food acceptable esters of cinnamic acid as potential lipophilic antioxidants.", publisher = "Tatranské Matliare : Slovak Society of Chemical Engineering", journal = "Proceedings of the 39th International Conference of Slovak Society of Chemical Engineering", title = "Enzymatic Synthesis of Aliphatic Esters of Phenolic Acids and Evaluation of Their Antioxidant Properties", pages = "1426-1432", url = "https://hdl.handle.net/21.15107/rcub_dais_493" }
Knežević Jugović, Z., Jakovetić, S., Jugović, B., Gvozdenović, M. M., Grbavčić, S., Bezbradica, D.,& Antov, M.. (2012). Enzymatic Synthesis of Aliphatic Esters of Phenolic Acids and Evaluation of Their Antioxidant Properties. in Proceedings of the 39th International Conference of Slovak Society of Chemical Engineering Tatranské Matliare : Slovak Society of Chemical Engineering., 1426-1432. https://hdl.handle.net/21.15107/rcub_dais_493
Knežević Jugović Z, Jakovetić S, Jugović B, Gvozdenović MM, Grbavčić S, Bezbradica D, Antov M. Enzymatic Synthesis of Aliphatic Esters of Phenolic Acids and Evaluation of Their Antioxidant Properties. in Proceedings of the 39th International Conference of Slovak Society of Chemical Engineering. 2012;:1426-1432. https://hdl.handle.net/21.15107/rcub_dais_493 .
Knežević Jugović, Zorica, Jakovetić, Sonja, Jugović, Branimir, Gvozdenović, Milica M., Grbavčić, Sanja, Bezbradica, Dejan, Antov, Mirjana, "Enzymatic Synthesis of Aliphatic Esters of Phenolic Acids and Evaluation of Their Antioxidant Properties" in Proceedings of the 39th International Conference of Slovak Society of Chemical Engineering (2012):1426-1432, https://hdl.handle.net/21.15107/rcub_dais_493 .