Abstract
Benzyl propionate is an aromatic ester that possesses a fruity odor and is usually found in nature in the composition of some fruits such as plums and melons. This work aimed for the benzyl propionate synthesis by esterification using a new immobilized enzyme preparation with low-cost material from Candida antarctica (NS 88011) and three commercial immobilized lipases (Novozym 435, Lipozyme TL-IM and Lipozyme RM-IM). Novozym 435 had the best performance even when the solvent tert-butanol was absent of the reaction medium. Results from a 22 factorial design showed that an increase in the enzyme amount led to a higher conversion, even when the temperature was kept at the low value. Currently, no research had synthesized successfully benzyl propionate via esterification mediated by lipases; and we reached an ester conversion of ~ 44% after 24 h indicating that it is a promising route for benzyl propionate biotechnological production.
Graphical abstract
Similar content being viewed by others
References
Berger RG (2009) Biotechnology of flavours—the next generation. Biotechnol Lett 31:1651–1659. https://doi.org/10.1007/s10529-009-0083-5
Dhake KP, Deshmukh KM, Wagh YS, Singhal RS (2012) Investigation of steapsin lipase for kinetic resolution of secondary alcohols and synthesis of valuable acetates in non-aqueous reaction medium. J Mol Catal B Enzym 77:15–23. https://doi.org/10.1016/j.molcatb.2012.01.009
Gao W, Wu K, Chen L, Fan H (2016) A novel esterase from a marine mud metagenomic library for biocatalytic synthesis of short-chain flavor esters. Microb Cell Fact 15:41. https://doi.org/10.1186/s12934-016-0435-5
Yadav GD, Dhoot SB (2009) Immobilized lipase-catalysed synthesis of cinnamyl laurate in non-aqueous media. J Mol Catal B Enzym 57:34–39. https://doi.org/10.1016/j.molcatb.2008.06.013
SÁ AGA, Meneses AC de, Araújo PHH de, Oliveira D de (2017) A review on enzymatic synthesis of aromatic esters used as flavor ingredients for food, cosmetics and pharmaceuticals industries. Trends Food Sci Technol 69:95–105. https://doi.org/10.1016/j.tifs.2017.09.004
Todero LM, Bassi JJ, Lage FAP, Corradini MCC (2015) Enzymatic synthesis of isoamyl butyrate catalyzed by immobilized lipase on poly-methacrylate particles: optimization, reusability and mass transfer studies. Bioprocess Biosyst Eng 38:1601–1613. https://doi.org/10.1007/s00449-015-1402-y
Silva NCA, Miranda JS, Bolina ICA, Silva WC (2014) Immobilization of porcine pancreatic lipase on poly-hydroxybutyrate particles for the production of ethyl esters from macaw palm oils and pineapple flavor. Biochem Eng J 82:1139–1149. https://doi.org/10.1016/j.bej.2013.11.015
Ferraz LIR, Possebom G, Alvez EV, Cansian RL (2015) Application of home-made lipase in the production of geranyl propionate by esterification of geraniol and propionic acid in solvent-free system. Biocatal Agric Biotechnol 4:44–48. https://doi.org/10.1016/j.bcab.2014.07.003
Białecka-Florjańczyk E, Krzyczkowska J, Stolarzewicz I, Kapturowska A (2012) Synthesis of 2-phenylethyl acetate in the presence of Yarrowia lipolytica KKP 379 biomass. J Mol Catal B Enzym 74:241–245. https://doi.org/10.1016/j.molcatb.2011.10.010
Khan NR, Rathod VK (2015) Enzyme catalyzed synthesis of cosmetic esters and its intensification: A review. Process Biochem 50:1793–1806. https://doi.org/10.1016/j.procbio.2015.07.014
Wang Y, Zhang D, Chen N, Zhi G (2015) Synthesis of benzyl cinnamate by enzymatic esterification of cinnamic acid. Bioresour Technol 198:256–261. https://doi.org/10.1016/j.biortech.2015.09.028
Vanin AB, Orlando T, Piazza SP, Puton BMS (2014) Antimicrobial and antioxidant activities of clove essential oil and eugenyl acetate produced by enzymatic esterification. Appl Biochem Biotechnol 174:1286–1298. https://doi.org/10.1007/s12010-014-1113-x
Santos P, Zabot GL, Meireles MAA, Mazutti MA (2016) Synthesis of eugenyl acetate by enzymatic reactions in supercritical carbon dioxide. Biochem Eng J 114:1–9. https://doi.org/10.1016/j.bej.2016.06.018
Silva MJA, Loss RA, Laroque DA, Lerin LA (2015) Lipozyme TL IM as catalyst for the synthesis of eugenyl acetate in solvent-free acetylation. Appl Biochem Biotechnol 176:782–795. https://doi.org/10.1007/s12010-015-1611-5
Chiaradia V, Paroul N, Cansian RL, Júnior CV (2012) Synthesis of eugenol esters by lipase-catalyzed reaction in solvent-free system. Appl Biochem Biotechnol 168:742–751. https://doi.org/10.1007/s12010-012-9814-5
Badgujar KC, Sasaki T, Bhanage BM (2015) Synthesis of lipase nano-bio-conjugates as an efficient biocatalyst: characterization and activity—stability studies with potential biocatalytic applications. RSC Adv 5:55238–55251. https://doi.org/10.1039/C5RA10032A
Singh M, Singh S, Singh RS, Chisti Y (2008) Transesterification of primary and secondary alcohols using Pseudomonas aeruginosa lipase. Bioresour Technol 99:2116–2120. https://doi.org/10.1016/j.biortech.2007.05.041
Badgujar KC, Pai PA, Bhanage BM (2016) Enhanced biocatalytic activity of immobilized Pseudomonas cepacia lipase under sonicated condition. Bioprocess Biosyst Eng 39:211–221. https://doi.org/10.1007/s00449-015-1505-5
FDA (2013) Code of Federal Regulations, 21 CFR 172.515, Department of Health and Human Services. Food additives permitted for direct addition to food for human consumption, flavoring agents and related substances. Food drug ADM, 3
Adams TB, Cohen SM, Doull J, Feron VJ (2005) The FEMA GRAS assessment of benzyl derivatives used as flavor ingredients. Food Chem Toxicol 43:1207–1240. https://doi.org/10.1016/j.fct.2004.11.014
FEMA (1965) Flavour and extract manufacturers association. Food Technol 19:151–197
Api AM, Belsito D, Bhatia S, Bruze M (2015) RIFM fragrance ingredient safety assessment, benzyl propionate, CAS Registry Number 122-63-4. Food Chem Toxicol 1–11. https://doi.org/10.1016/j.fct.2015.12.010
McGinty D, Letizia CS, Api AM (2012) Fragrance material review on benzyl propionate. Food Chem Toxicol 50:S486–S490. https://doi.org/10.1016/j.fct.2013.08.067
Badgujar KC, Bhanage BM (2014) Enhanced biocatalytic activity of lipase immobilized on biodegradable copolymer of chitosan and polyvinyl alcohol support for synthesis of propionate ester: kinetic approach. Ind Eng Chem Res 53:18806–18815. https://doi.org/10.1021/ie501304e
Ceni G, Lerin LA, Conto JF, Brancher CV (2010) Optimization of 1-glyceryl benzoate production by enzymatic transesterification in organic solvents. Enzyme Microb Technol 46:107–112. https://doi.org/10.1016/j.enzmictec.2009.09.011
Acknowledgements
The authors thank the financial support from CAPES (Coordenação de Aperfeiçoamento de Pessoal de Nível Superior) and CNPq (Conselho Nacional de Desenvolvimento Científico e Tecnológico).
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
Conflict of interest
The authors declare that they have no conflict of interest.
Additional information
Amanda Gomes Almeida Sá and Alessandra Cristina de Meneses contributed equally to this work.
Rights and permissions
About this article
Cite this article
Sá, A.G.A., de Meneses, A.C., Lerin, L.A. et al. Biocatalysis of aromatic benzyl-propionate ester by different immobilized lipases. Bioprocess Biosyst Eng 41, 585–591 (2018). https://doi.org/10.1007/s00449-018-1893-4
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00449-018-1893-4