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.
TY - 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 .
