Chiral Technologies, Inc., 1475 Dunwoody Drive, Suite 310, West Chester, PA 19380, USA.
Molecules. 2023 Jan 24;28(3):1164. doi: 10.3390/molecules28031164.
Until recently, chirality has not been a major focus in the study of cannabinoids, as most cannabinoids of interest, such as cannabidiol and tetrahydrocannabinol, exist as a single isomer from natural sources. However, this is changing as more cannabinoids are identified, and compounds such as cannabichromene and cannabicyclol are emerging as potential investigatory candidates for varying indications. Because these molecules are chiral, the separation and study of the individual enantiomers' biological and physiological effects should therefore be of interest. The purpose of this study was to identify analytical separation conditions and then adapt those conditions to preparative separation. This was accomplished with a column-screening approach on Daicel's immobilized polysaccharide chiral stationary phases using non-traditional mobile phases, which included dichloromethane, ethyl acetate, and methyl tert-butyl ether under high-performance liquid chromatography conditions. CHIRALPAK IK was found to separate all four compounds well with mobile phases containing hexane-dichloromethane (with or without an acidic additive). From these methods, the separation productivities were calculated to better visualize the separation scalability, which shows that the kilogram-scale separations of each are feasible.
直到最近，手性在大麻素研究中还不是一个主要关注点，因为大多数具有研究价值的大麻素，如大麻二酚和四氢大麻酚，从天然来源中存在的都是单一异构体。然而，随着更多大麻素被发现，一些化合物如大麻色烯和大麻环醇作为不同适应症的潜在研究候选物正在出现。由于这些分子是手性的，因此应该对手性对映体的生物和生理效应进行分离和研究。本研究的目的是确定分析分离条件，然后将这些条件适应于制备分离。这是通过在 Daicel 的固定化多糖手性固定相上进行柱筛选方法，使用非传统的流动相来实现的，这些流动相包括在高效液相色谱条件下的二氯甲烷、乙酸乙酯和甲基叔丁基醚。CHIRALPAK IK 被发现可以很好地分离所有四种化合物，使用含有正己烷-二氯甲烷（有或没有酸性添加剂）的流动相。从这些方法中，计算了分离的生产率，以便更好地可视化分离的可扩展性，这表明每个化合物的公斤级分离是可行的。
