Enzymatic Synthesis of Aliphatic Esters of Phenolic Acids and Evaluation of Their Antioxidant Properties
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...
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Tatranské Matliare : Slovak Society of Chemical Engineering
2012
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ftunivbelgradftm:oai:TechnoRep.tmf.bg.ac.rs:123456789/2019 2023-12-24T10:10:10+01:00 Enzymatic Synthesis of Aliphatic Esters of Phenolic Acids and Evaluation of Their Antioxidant Properties Knežević-Jugović, Zorica Jakovetić, Sonja Jugović, Branimir Gvozdenović, Milica Grbavčić, Sanja Bezbradica, Dejan Antov, Mirjana 2012 http://TechnoRep.tmf.bg.ac.rs/handle/123456789/2019 http://TechnoRep.tmf.bg.ac.rs/bitstream/id/469/2016.pdf https://hdl.handle.net/21.15107/rcub_technorep_2019 unknown Tatranské Matliare : Slovak Society of Chemical Engineering info:eu-repo/grantAgreement/MESTD/Integrated and Interdisciplinary Research (IIR or III)/46010/RS// 978-80-89475-04-9 http://TechnoRep.tmf.bg.ac.rs/handle/123456789/2019 http://TechnoRep.tmf.bg.ac.rs/bitstream/id/469/2016.pdf https://hdl.handle.net/21.15107/rcub_technorep_2019 openAccess https://creativecommons.org/licenses/by-nc-nd/4.0/ BY-NC-ND Proceedings of the 39th International Conference of Slovak Society of Chemical Engineering phenolic acid esters enzymatic esterification ethyl cinnamate Candida antarctica lipase radical-scavenging activity antioxidant activity cyclic voltammetry conferenceObject publishedVersion 2012 ftunivbelgradftm 2023-11-28T17:19:52Z 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. Conference Object Antarc* Antarctica TechnoRep - Faculty of Technology and Metallurgy Repository |
institution |
Open Polar |
collection |
TechnoRep - Faculty of Technology and Metallurgy Repository |
op_collection_id |
ftunivbelgradftm |
language |
unknown |
topic |
phenolic acid esters enzymatic esterification ethyl cinnamate Candida antarctica lipase radical-scavenging activity antioxidant activity cyclic voltammetry |
spellingShingle |
phenolic acid esters enzymatic esterification ethyl cinnamate Candida antarctica lipase radical-scavenging activity antioxidant activity cyclic voltammetry Knežević-Jugović, Zorica Jakovetić, Sonja Jugović, Branimir Gvozdenović, Milica Grbavčić, Sanja Bezbradica, Dejan Antov, Mirjana Enzymatic Synthesis of Aliphatic Esters of Phenolic Acids and Evaluation of Their Antioxidant Properties |
topic_facet |
phenolic acid esters enzymatic esterification ethyl cinnamate Candida antarctica lipase radical-scavenging activity antioxidant activity cyclic voltammetry |
description |
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. |
format |
Conference Object |
author |
Knežević-Jugović, Zorica Jakovetić, Sonja Jugović, Branimir Gvozdenović, Milica Grbavčić, Sanja Bezbradica, Dejan Antov, Mirjana |
author_facet |
Knežević-Jugović, Zorica Jakovetić, Sonja Jugović, Branimir Gvozdenović, Milica Grbavčić, Sanja Bezbradica, Dejan Antov, Mirjana |
author_sort |
Knežević-Jugović, Zorica |
title |
Enzymatic Synthesis of Aliphatic Esters of Phenolic Acids and Evaluation of Their Antioxidant Properties |
title_short |
Enzymatic Synthesis of Aliphatic Esters of Phenolic Acids and Evaluation of Their Antioxidant Properties |
title_full |
Enzymatic Synthesis of Aliphatic Esters of Phenolic Acids and Evaluation of Their Antioxidant Properties |
title_fullStr |
Enzymatic Synthesis of Aliphatic Esters of Phenolic Acids and Evaluation of Their Antioxidant Properties |
title_full_unstemmed |
Enzymatic Synthesis of Aliphatic Esters of Phenolic Acids and Evaluation of Their Antioxidant Properties |
title_sort |
enzymatic synthesis of aliphatic esters of phenolic acids and evaluation of their antioxidant properties |
publisher |
Tatranské Matliare : Slovak Society of Chemical Engineering |
publishDate |
2012 |
url |
http://TechnoRep.tmf.bg.ac.rs/handle/123456789/2019 http://TechnoRep.tmf.bg.ac.rs/bitstream/id/469/2016.pdf https://hdl.handle.net/21.15107/rcub_technorep_2019 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
Proceedings of the 39th International Conference of Slovak Society of Chemical Engineering |
op_relation |
info:eu-repo/grantAgreement/MESTD/Integrated and Interdisciplinary Research (IIR or III)/46010/RS// 978-80-89475-04-9 http://TechnoRep.tmf.bg.ac.rs/handle/123456789/2019 http://TechnoRep.tmf.bg.ac.rs/bitstream/id/469/2016.pdf https://hdl.handle.net/21.15107/rcub_technorep_2019 |
op_rights |
openAccess https://creativecommons.org/licenses/by-nc-nd/4.0/ BY-NC-ND |
_version_ |
1786213760176750592 |