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Synthesis of flavor and fragrance esters using Candida antarctica lipase.

Applied microbiology and biotechnology (2004-07-13)
Araceli Larios, Hugo S García, Rosa María Oliart, Gerardo Valerio-Alfaro
RÉSUMÉ

Candida antarctica lipase fraction B (CAL-B) showed substrate specificity in the synthesis of esters in hexane involving reactions of short-chain acids having linear (acetic and butyric acids) and branched chain (isovaleric acid) structures, an unsaturated (tiglic acid) fatty acid, and phenylacetic acid with n-butanol and geraniol. The variation in the conversion to the esters was ca. 10%. Similar results were observed in a study of the alcohol specificity of the enzyme for esterification of acetic and butyric acids with four alcohols: n-butyl, isopentyl, 2-phenylethyl, and geraniol. Enantioselectivity of CAL-B in hexane with a range of chiral alpha-substituted or beta-substituted carboxylic acids and n-butyl alcohol was analyzed. The results show that CAL-B can be employed as a robust biocatalyst in esterification reactions due to the high conversions obtained in the synthesis of short-chain flavor esters in an organic solvent, although this enzyme exhibited modest enantioselectivity with chiral short-chain carboxylic acids.

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Sigma-Aldrich
trans-2-Methyl-2-butenoic acid, ≥99%, FG
Sigma-Aldrich
trans-2,3-Dimethylacrylic acid, 98%