Resolution of racemic 3-hydroxy-4,5-dimethyl-2(5H)-furanone (sotolon) by packed column supercritical fluid chromatography

Authors


Jianchun Xie, Beijing Key Laboratory of Flavor Chemistry, Beijing Technology and Business University, Beijing 100048, P.R. China. E-mail: xjchun@th.btbu.edu.cn

ABSTRACT

The resolution of racemic 3-hydroxy-4,5-dimethyl-2(5H)-furanone (sotolon) by packed column supercritical fluid chromatography was studied. On an analytical scale, the chiral stationary phases of Chiralpak AD-H, Chiralcel OB-H, Chiralcel OD-H, and Chiralcel OJ-H along with methanol, ethanol, isopropanol and acetonitrile as organic modifiers were tested. The effect on resolution of the modifier content in mobile phase, column temperature, column pressure, and flow rate of mobile phase was investigated through single-factor experiment and orthogonal experiment. The optimum conditions found were Chiralpak AD-H, column temperature 28°C, column pressure 8 MPa, 2.5% (v/v) methanol in the mobile phase, and a flow rate of 1.5 ml/min for the mobile phase, whereby the resolution achieved was 2.98. Several milligrams of enantiomers, with an optical purity of S-100% and R-93%, were obtained by scaling up the analytical method to preparative separation using Chiralpak AD (250 × 10 mm I.D. 10 µm ps). Copyright © 2012 John Wiley & Sons, Ltd.

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