Lipase-Catalyzed Esterification of Geraniol and Citronellol for the Synthesis of Terpenic Esters
This article describes the synthesis of terpenic esters derived from geraniol and citronellol (geranyl and citronellyl alkanoates) through esterification reactions catalyzed by the immobilized lipases from Thermomyces lanuginosus (Lipozyme TL IM®) and Candida antarctica (Novozym 435®). Geraniol was...
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Online Access: | http://hdl.handle.net/11392/2464219 https://doi.org/10.1007/s12010-019-03102-1 https://link.springer.com/article/10.1007/s12010-019-03102-1 |
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ftunivferrarair:oai:sfera.unife.it:11392/2464219 2024-09-09T19:07:13+00:00 Lipase-Catalyzed Esterification of Geraniol and Citronellol for the Synthesis of Terpenic Esters da Silva Correa L. Henriques R. O. Rios J. V. Lerin L. A. de Oliveira D. Furigo A. da Silva Correa, L. Henriques, R. O. Rios, J. V. Lerin, L. A. de Oliveira, D. Furigo, A. 2020 ELETTRONICO http://hdl.handle.net/11392/2464219 https://doi.org/10.1007/s12010-019-03102-1 https://link.springer.com/article/10.1007/s12010-019-03102-1 eng eng info:eu-repo/semantics/altIdentifier/pmid/31396887 info:eu-repo/semantics/altIdentifier/wos/WOS:000520099700016 volume:190 issue:2 firstpage:574 lastpage:583 numberofpages:10 journal:APPLIED BIOCHEMISTRY AND BIOTECHNOLOGY http://hdl.handle.net/11392/2464219 doi:10.1007/s12010-019-03102-1 info:eu-repo/semantics/altIdentifier/scopus/2-s2.0-85070301300 https://link.springer.com/article/10.1007/s12010-019-03102-1 info:eu-repo/semantics/closedAccess Citronellol Flavor Geraniol Lipase Terpenic esters info:eu-repo/semantics/article 2020 ftunivferrarair https://doi.org/10.1007/s12010-019-03102-1 2024-06-19T13:52:33Z This article describes the synthesis of terpenic esters derived from geraniol and citronellol (geranyl and citronellyl alkanoates) through esterification reactions catalyzed by the immobilized lipases from Thermomyces lanuginosus (Lipozyme TL IM®) and Candida antarctica (Novozym 435®). Geraniol was esterified with oleic, lauric, and stearic acids; and citronellol was esterified with oleic and stearic acids. For all the synthesized flavor esters, the best conditions were 35 °C, and the molar ratio between acid and alcohol was 1:1. Geranyl and citronellyl alkanoates reached yields between 80-100% within 4 h of reaction. For the synthesis of the citronellyl and geranyl oleate, higher yields were obtained in the absence of organic solvents. For the esters from lauric and stearic acids, using solvent was indispensable to improve the miscibility between the substrates. The reuse of Novozym 435® and Lipozyme TL IM® was performed for two more cycles after the first use, with yields higher than 60%. The results demonstrated the efficiency of the reaction catalyzed by these two commercial enzymes and the feasibility of the methodology for the production of synthetic flavor esters through enzymatic catalysis. The flavor esters synthesized were not described in the literature up to the date, giving this research an innovative feature. Article in Journal/Newspaper Antarc* Antarctica Università degli Studi di Ferrara: CINECA IRIS Applied Biochemistry and Biotechnology 190 2 574 583 |
institution |
Open Polar |
collection |
Università degli Studi di Ferrara: CINECA IRIS |
op_collection_id |
ftunivferrarair |
language |
English |
topic |
Citronellol Flavor Geraniol Lipase Terpenic esters |
spellingShingle |
Citronellol Flavor Geraniol Lipase Terpenic esters da Silva Correa L. Henriques R. O. Rios J. V. Lerin L. A. de Oliveira D. Furigo A. Lipase-Catalyzed Esterification of Geraniol and Citronellol for the Synthesis of Terpenic Esters |
topic_facet |
Citronellol Flavor Geraniol Lipase Terpenic esters |
description |
This article describes the synthesis of terpenic esters derived from geraniol and citronellol (geranyl and citronellyl alkanoates) through esterification reactions catalyzed by the immobilized lipases from Thermomyces lanuginosus (Lipozyme TL IM®) and Candida antarctica (Novozym 435®). Geraniol was esterified with oleic, lauric, and stearic acids; and citronellol was esterified with oleic and stearic acids. For all the synthesized flavor esters, the best conditions were 35 °C, and the molar ratio between acid and alcohol was 1:1. Geranyl and citronellyl alkanoates reached yields between 80-100% within 4 h of reaction. For the synthesis of the citronellyl and geranyl oleate, higher yields were obtained in the absence of organic solvents. For the esters from lauric and stearic acids, using solvent was indispensable to improve the miscibility between the substrates. The reuse of Novozym 435® and Lipozyme TL IM® was performed for two more cycles after the first use, with yields higher than 60%. The results demonstrated the efficiency of the reaction catalyzed by these two commercial enzymes and the feasibility of the methodology for the production of synthetic flavor esters through enzymatic catalysis. The flavor esters synthesized were not described in the literature up to the date, giving this research an innovative feature. |
author2 |
da Silva Correa, L. Henriques, R. O. Rios, J. V. Lerin, L. A. de Oliveira, D. Furigo, A. |
format |
Article in Journal/Newspaper |
author |
da Silva Correa L. Henriques R. O. Rios J. V. Lerin L. A. de Oliveira D. Furigo A. |
author_facet |
da Silva Correa L. Henriques R. O. Rios J. V. Lerin L. A. de Oliveira D. Furigo A. |
author_sort |
da Silva Correa L. |
title |
Lipase-Catalyzed Esterification of Geraniol and Citronellol for the Synthesis of Terpenic Esters |
title_short |
Lipase-Catalyzed Esterification of Geraniol and Citronellol for the Synthesis of Terpenic Esters |
title_full |
Lipase-Catalyzed Esterification of Geraniol and Citronellol for the Synthesis of Terpenic Esters |
title_fullStr |
Lipase-Catalyzed Esterification of Geraniol and Citronellol for the Synthesis of Terpenic Esters |
title_full_unstemmed |
Lipase-Catalyzed Esterification of Geraniol and Citronellol for the Synthesis of Terpenic Esters |
title_sort |
lipase-catalyzed esterification of geraniol and citronellol for the synthesis of terpenic esters |
publishDate |
2020 |
url |
http://hdl.handle.net/11392/2464219 https://doi.org/10.1007/s12010-019-03102-1 https://link.springer.com/article/10.1007/s12010-019-03102-1 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_relation |
info:eu-repo/semantics/altIdentifier/pmid/31396887 info:eu-repo/semantics/altIdentifier/wos/WOS:000520099700016 volume:190 issue:2 firstpage:574 lastpage:583 numberofpages:10 journal:APPLIED BIOCHEMISTRY AND BIOTECHNOLOGY http://hdl.handle.net/11392/2464219 doi:10.1007/s12010-019-03102-1 info:eu-repo/semantics/altIdentifier/scopus/2-s2.0-85070301300 https://link.springer.com/article/10.1007/s12010-019-03102-1 |
op_rights |
info:eu-repo/semantics/closedAccess |
op_doi |
https://doi.org/10.1007/s12010-019-03102-1 |
container_title |
Applied Biochemistry and Biotechnology |
container_volume |
190 |
container_issue |
2 |
container_start_page |
574 |
op_container_end_page |
583 |
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1809821290100424704 |