Chemical and enzymatic synthesis of a library of 2-phenethyl esters and their sensory attributes

Cheng Li; Jingcan Sun; Tianhu Li; Shao-Quan Liu; Dejian Huang

doi:10.1016/j.foodchem.2013.12.102

Chemical and enzymatic synthesis of a library of 2-phenethyl esters and their sensory attributes

Food Chem. 2014 Jul 1:154:205-10. doi: 10.1016/j.foodchem.2013.12.102. Epub 2014 Jan 8.

Authors

Cheng Li¹, Jingcan Sun², Tianhu Li¹, Shao-Quan Liu³, Dejian Huang⁴

Affiliations

¹ Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore.
² Food Science and Technology Program, Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543, Singapore.
³ Food Science and Technology Program, Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543, Singapore. Electronic address: chmlsq@nus.edu.sg.
⁴ Food Science and Technology Program, Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543, Singapore. Electronic address: chmhdj@nus.edu.sg.

PMID: 24518334
DOI: 10.1016/j.foodchem.2013.12.102

Abstract

We report a simple enzymatic approach to synthesise phenethyl esters as natural flavouring materials. Chemical and lipase-catalysed esterification reactions between fatty acids of C4-C18 and 2-phenethyl alcohol were studied. Both methods were compared qualitatively and quantitatively by GC-MS/FID. The acid and thermal stabilities of 2-phenethyl esters were excellent and can meet the requirements of food matrices under most processing conditions. Sensory evaluation showed that each 2-phenethyl ester with a different carbon-chain-length fatty acid had unique sensory notes. Moreover, through Lipozyme TL IM-mediated transesterification, valuable 2-phenethyl alcohol-derived esters were synthesised from butter oil and 2-phenethyl alcohol. The influence of several physicochemical parameters (temperature, substrate molar ratio, enzyme loading, shaking speed and time) on the transesterification reaction was investigated to give optimal reaction conditions, leading to a high yield of 80.0%.

Keywords: 2-Phenethyl ester; Esterification; Flavour esters; Lipase.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Adult
Biocatalysis
Fatty Acids / chemistry
Female
Flavoring Agents / chemical synthesis*
Flavoring Agents / chemistry
Gas Chromatography-Mass Spectrometry
Humans
Lipase / chemistry*
Male
Molecular Structure
Phenyl Ethers / chemical synthesis*
Phenyl Ethers / chemistry
Taste*
Temperature

Substances

Fatty Acids
Flavoring Agents
Phenyl Ethers
Lipase