填充柱超临界流体色谱手性拆分5-羟基-8-十一碳烯酸-δ-内酯（茉莉内酯）

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

摘要:

研究了填充柱超临界CO2流体色谱手性拆分外消旋5-羟基-8-十一碳烯酸-δ-内酯(茉莉内酯)的方法。在筛选固定相种类及改性剂种类基础上，通过单因素及正交实验较为系统地考察了柱温、柱压、改性剂含量、流速等因素的影响，优化出较佳的分析型分离条件：固定相 Chiralcel OD-H，柱温31 ℃，柱压12 Mpa，改性剂乙腈-甲醇(7:3, v/v)，在流动相中含量2.0 % (v/v)，流速1.0 mL/min，分离度2.00。利用较佳条件，在流速8 mL/min下进行制备规模放大，320 min内进样10 mg得6.6 mg两对映体产品，回收率66 %，光学纯度(e.e %)均为100 %，表明超临界流体色谱分离效率高，可作为茉莉内酯mg级对映体纯品快速制备的手段。

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.