[CH:1]1([CH3:11])[CH2:6][CH2:5][CH:4]([CH:7]([CH3:9])[CH3:8])[CH:3]([OH:10])[CH2:2]1.[CH3:12][CH:13]1[CH2:18][C@H:17]([OH:19])[C@@H:16]([CH:20]([CH3:22])[CH3:21])[CH2:15][CH2:14]1.C(OC=C)(=O)C>CCCCCCC>[C:17]([O:10][CH:3]1[CH:4]([CH:7]([CH3:8])[CH3:9])[CH2:5][CH2:6][CH:1]([CH3:11])[CH2:2]1)(=[O:19])[CH3:16].[CH:13]1([CH3:12])[CH2:14][CH2:15][CH:16]([CH:20]([CH3:21])[CH3:22])[CH:17]([OH:19])[CH2:18]1Lyophilised “AMANO AK” (a Pseudomonas fluorescens lipase enzyme) was obtained from Amano Pharmaceutical Co. (Japan). Concentrated liquid menthol was produced by the hydrogenation of thymol. The menthol contained four diastereomeric pairs of menthols, namely (+)-menthol (51%), (±)-isomenthol (14%), (±)-neomenthol (29%) and (±)-neoisomenthol (2%). A volume of 1 ml was added to sealed batch reactors. Vinyl acetate (54 μl) was added at a 2:1 molar ratio to (−)-menthol. Heptane was added as solvent to a final reaction volume of 5 ml. These reactors were incubated in silicon oil baths at 50° C. and stirred on a stirring hot plate. Batch times, unless otherwise stated were 24 hours. The reaction mixture was then centrifuged to separate the products from the enzyme. The supernatant was analysed by GC (% m/m analysis). Of the available (−)-menthol, 100% was converted to (−)-menthyl acetate, at an ee of 98%. The enzyme was recycled a total of 150 times by washing with heptane and adding fresh substrate (liquid menthol, vinyl acetate and heptane) after every recycle. An amount of menthyl acetate equivalent to 185 g of (−)-menthol was produced by this process.
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