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Lipozyme TL IM as Catalyst for the Synthesis of Eugenyl Acetate in Solvent-Free Acetylation

Applied Biochemistry and Biotechnology volume 176, pages 782–795 (2015)Cite this article

Abstract

The ability of commercial immobilized lipase from Thermomyces lanuginosus (Lipozyme TL IM) to catalyze the acetylation of essential clove oil with acetic anhydride in a solvent-free system was studied, and the antimicrobial activity of the ester formed was evaluated as well. Experimental design based on two variables (eugenol to acetic anhydride molar ratio and temperature) was employed to evaluate the experimental conditions of eugenyl acetate ester production. The maximum conversion yield (92.86 %) was obtained using Lipozyme TL IM (5 wt%, based on the total amount of substrates), with eugenol to acetic anhydride molar ratio of 1:5 at 70 °C. The chemical structure of the eugenyl acetate ester obtained at the optimized condition, and purified, was confirmed by the proton nuclear magnetic resonance (1H-NMR) analysis. The antimicrobial activity of eugenyl acetate ester was proven effective on Gram-positive and Gram-negative bacteria, with means of 16.62 and 17.55 mm of inhibition halo.

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Affiliations

  1. Universidade Federal de Santa Catarina, UFSC, Campus Universitário Reitor João David Ferreira Lima, Trindade, 88040-900, Florianópolis, SC, Brazil

    María José A. Silva, Raquel A. Loss, Denise A. Laroque, Lindomar A. Lerin, Gabriela N. Pereira, J. Vladimir Oliveira, Jorge L. Ninow, Haiko Hense & Débora Oliveira

  2. Universidade Estadual do Estado de Mato Grosso, UNEMAT, Campus Universitário Deputado Estadual Renê Bardour, São Raimundo, 78390-000, Barra do Bugres, MT, Brazil

    Raquel A. Loss

  3. Oniris Nantes. École Nationale Vétérinaire, Agroalimentaire et de l’Alimentation, Rue de la Géraudière, BP 82225, 44322, Nantes cedex 3, , Nantes, France

    Élise Thon

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  1. María José A. Silva
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  2. Raquel A. Loss
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  3. Denise A. Laroque
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  4. Lindomar A. Lerin
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  5. Gabriela N. Pereira
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  6. Élise Thon
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  7. J. Vladimir Oliveira
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  9. Haiko Hense
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  10. Débora Oliveira
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Correspondence to Débora Oliveira.

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Silva, M.J.A., Loss, R.A., Laroque, D.A. et al. Lipozyme TL IM as Catalyst for the Synthesis of Eugenyl Acetate in Solvent-Free Acetylation. Appl Biochem Biotechnol 176, 782–795 (2015). https://doi.org/10.1007/s12010-015-1611-5

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  • DOI: https://doi.org/10.1007/s12010-015-1611-5

Keywords

  • Lipozyme TL IM
  • Antimicrobial activity
  • Eugenyl acetate
  • Acetylation