顺式和反式氯氰菊酯对映体的制备及其纯度鉴定

Preparation and purity identification of cis-cypermethrin and trans-cypermethrin enantiomers

中文关键词:  手性拆分  顺式氯氰菊酯  反式氯氰菊酯  对映体制备  纯度鉴定  手性气相色谱-质谱联用法

英文关键词:chiral resolution  cis-cypermethrin  trans-cypermethrin  enantiomers preparation  purity identification  chiral gas chromatography mass spectrometry

中文摘要:

      目的 制备顺式和反式氯氰菊酯对映体, 并进行纯度鉴定。方法 采用定制涂敷型β-环糊精填料的手性制备柱, 通过高压制备色谱分别对顺式、反式氯氰菊酯工业品进行手性拆分, 收集各对映体馏分, 减压蒸馏、冻干, 制备重量为10 g以上的4个对映体; 采用正相手性高效液相色谱、气相色谱质谱、手性气相色谱质谱联用等技术分别对制备的4个对映体进行定性鉴定和纯度测定。结果 该方法制备的顺式氯氰菊酯2个对映体构型分别为1R-cis-αS和1S-cis-αR, 纯度分别为98.4%和99.0%; 反式氯氰菊酯2个对映体构型分别为1R-trans-αS和1S-trans-αR, 纯度分别为98.6%和99.0%。所制备的4个对映体重量均超过了10 g。结论 该方法可成功分离顺式和反式氯氰菊酯对映体, 所制备的对映体重量为10 g以上且纯度均在98%以上, 达到了标准品的要求, 能满足后续体内代谢试验和体外细胞实验的需求。

英文摘要:

      Objective To prepare cis-and trans-cypermethrin enantiomers and to carry out purity identification. Methods The chiral resolution and enantiomers preparation of cis-cypermethrin and trans-cypermethrin were carried out by preparation high performance liquid chromatography coupled with the preparation of β-cyclodextrin coated chiral column, respectively. The 4 enantiomer products were gained by vacuum distilled and lyophilized separately, until their weight were more than 10 g. Their qualitative and quantitative analysis were carried by normal phase high performance liquid chromatography, gas chromatography-mass spectrometry, and chiral gas chromatography-mass spectrometry techniques, respectively. Results The configurations of cis-cypermethrin were found to be 1R-cis-αS and 1S-cis-αR with purities of 98.4% and 99.0%, and the configurations of trans-cypermethrin were found to be 1R-trans-αS and 1S-trans-αR with purities of 98.6% and 99.0%, respectively. The weight of all enantiomers was much more than 10 g. Conclusion The enantiomers of cis- and trans-cypermethrin could be separated successfully with a weight of more than 10 g and a purity of more than 98%, which could meet the standard reference material requirement, as well as the demand of metabolism tests in vivo and cytotoxicity tests in vitro.