title: Lipozyme TL IM as Catalyst for the Synthesis of Eugenyl Acetate in Solvent-Free Acetylation.
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 ((1)H-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.
authors: Universidade Federal de Santa Catarina, UFSC, Campus Universitário Reitor João David Ferreira Lima, Trindade, 88040-900, Florianópolis, SC, Brazil.
authors: María José A
authors: MJ
authors: Silva
authors: Raquel A
authors: RA
authors: Loss
authors: Denise A
authors: DA
authors: Laroque
authors: Lindomar A
authors: LA
authors: Lerin
authors: Gabriela N
authors: GN
authors: Pereira
authors: Élise
authors: É
authors: Thon
authors: J Vladimir
authors: JV
authors: Oliveira
authors: Jorge L
authors: JL
authors: Ninow
authors: Haiko
authors: H
authors: Hense
authors: Débora
authors: D
authors: Oliveira
mesh_terms: D000089:Acetic Anhydrides / Q000378:metabolism; D000107:Acetylation; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects; D055162:Biocatalysis; D060326:Chemistry Techniques, Synthetic; D045783:Clove Oil / Q000378:metabolism; D004800:Enzymes, Immobilized / Q000737:chemistry / Q000378:metabolism; D005054:Eugenol / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000494:pharmacology; D032641:Eurotiales / Q000201:enzymology; D007700:Kinetics; D008049:Lipase / Q000737:chemistry / Q000378:metabolism*
chemical_list: D000089:Acetic Anhydrides; D000900:Anti-Bacterial Agents; D045783:Clove Oil; D004800:Enzymes, Immobilized; C031800:acetic anhydride; D005054:Eugenol; C081939:acetyleugenol; C093666:Lipozyme; D008049:Lipase