Polysaccharide Chiral Stationary Phases for the Achiral and Chiral Separation of Cannabinoids

Abstract

Polysaccharide-based chiral stationary phases (CSPs) have been widely utilized in the pharmaceutical, agricultural, and natural product industries since their first-reported use and subsequent commercialization more than 50 years ago. Although they have been traditionally used for the separation of small drug molecules containing one or more chiral centers, their uses have recently grown to include achiral separations in emerging fields like the cannabis industry. The ability to separate and study individual cannabinoids is critical to understanding their impact in both medicinal and recreational applications. Furthermore, it is not difficult to envision a future where cannabinoids, particularly for medicinal use, are treated like pharmaceuticals—that is requiring rigorous purity testing, including the determination of chiral purity. While current methods of analysis are sufficient for the separation of achiral cannabinoid mixtures, some critical chiral pairs like cannabichromene cannot be separated fully. This is where the use of polysaccharide CSPs is and will continue to be important, as a chiral resolution will be needed to satisfy these potential requirements. This chapter will cover an introduction and evolution of polysaccharide CSPs, including a discussion on their unique separations mechanism, and review a number of the applications described in the literature of their uses for the achiral and chiral separation of cannabinoids.

Chiral Separation of Cannabichromene, Cannabicyclol, and Their Acidic Analogs on Polysaccharide Chiral Stationary Phases

“…This was followed by a considerable lull until the late 2000s and into the 2010s. More recently, the activity has picked up not only for chiral separations of cannabinoids but also for the achiral separation of cannabinoid mixtures on polysaccharide CSPs [ 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 , 38 , 39 ]. Unlike the many non-chiral methods on C18 or silica, chiral phases can achieve a mixed-mode separation of both chiral and non-chiral, making them a powerful tool for complex separations.…”