Resolution of 5-hydroxy-8-undecenoic acid δ-lactone (Jasmolactone) by packed column supercritical fluid chromatography
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TQ65

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    Abstract:

    The resolution of racemic 5-hydroxy-8-undecenoic acid δ-lactone (Jasmolactone) by packed column supercritical fluid chromatography (pSFC) was studied. First method development was carried out in an analytical scale. The chiral stationary phases (CSPs) of Chiralpak AD-H, Chiralcel OB-H, Chiralcel OD-H, and Chiralcel OJ-H, and the modifier solvents of methanol, ethanol, isopropanol and acetonitrile were screened. The parameters of column temperature, column pressure, content of modifier solvent in mobile phase, and flow rate of mobile phase were systematically investigated by single-factor and orthogonal experiments. The optimum conditions found were the CSP of Chiralcel OD-H, column temperature 31 ℃, column pressure 12 MPa, 2 % v/v modifier solvent of acetronile-methanol (7:3, v/v) in the mobile phase, and the flow rate of mobile phase in 1.0 mL/min, whereby resolution factor (Rs) achieved is 2.00. Then preparative separation was performed in the optimum conditions at a flow rate of 8 mL/min, total of 6.6 mg enantiomers were obtained from 10 mg racemers in 320 min in the recovery of 66 % and an optical purity of 100 % e. e. The present work demonstrated that resolution by pSFC was a good choice due to high efficiency when some micrograms of enantiomeric 5-hydroxy-8-undecenoic acid δ-lactone are to be prepared.

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History
  • Received:April 08,2013
  • Revised:May 04,2013
  • Adopted:May 14,2013
  • Online: July 29,2013
  • Published:
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