Enzymatic synthesis of rose aromatic ester (2-phenylethyl acetate) by lipase

J Sci Food Agric. 2012 Aug 15;92(10):2141-7. doi: 10.1002/jsfa.5599. Epub 2012 Mar 6.

Abstract

Background: 2-Phenylethyl acetate (2-PEAc) is a highly valued natural volatile ester with a rose-like odour that is widely used to add scent or flavour to cosmetics, soaps, foods and drinks. In this study, 2-PEAc was synthesised enzymatically by transesterification of vinyl acetate with 2-phenethyl alcohol catalysed by immobilised lipase (Novozym(®) 435) from Candida antarctic

Results: Response surface methodology and a three-level/three-factor Box-Behnken design were used to evaluate the effects of time, temperature and enzyme amount on the molar conversion % of 2-PEAc. The results showed that temperature was the most important variable. Based on the ridge max analysis results, optimum enzymatic synthesis conditions were predicted as a reaction time of 79 min, a temperature of 57.8 °C and an enzyme amount of 122.5 mg. The predicted and experimental yields were 86.4 and 85.4% respectively.

Conclusion: Three immobilised lipases were screened and 15 reaction conditions were tested in order to find the combination for maximum yield. The optimisation of 2-PEAc synthesis catalysed by Novozym(®) 435 was successfully developed. The kinetic study of this transesterification reaction showed that it followed an ordered ping-pong bi-bi mechanism without any inhibition by reactants.

MeSH terms

  • Acetates / chemical synthesis*
  • Candida / enzymology*
  • Enzymes, Immobilized / metabolism*
  • Esterification
  • Kinetics
  • Lipase / metabolism*
  • Odorants*
  • Phenylethyl Alcohol / analogs & derivatives*
  • Phenylethyl Alcohol / chemical synthesis
  • Rosa / chemistry*
  • Temperature*

Substances

  • Acetates
  • Enzymes, Immobilized
  • 2-phenylethyl acetate
  • Lipase
  • Phenylethyl Alcohol