Resolution of chiral cannabinoids on amylose tris(3,5-dimethylphenylcarbamate) chiral stationary phase: effects of structural features and mobile phase additives.
The separation of six pairs of chiral cannabinoids was achieved using a dimethylphenylcarbamate derivative of amylose, immobilized on silica gel (ChiralPak AD, Daicel), using 2-propanol and ethanol as the modifiers of n-hexane in the mobile phase. Good separation was achieved for most of the solutes in both solvent systems under various conditions. The chromatographic parameters of various cannabinoids in the two solvent systems were determined. The pairs differ from each other in small structural features such as the degree of saturation, position of a double bond and closure of a pyran ring. Therefore, a comparative study could give some clues regarding the mechanism of discrimination between the enantiomeric pairs on the chiral stationary phase. Preliminary measurements of limit of determination showed that it was possible to assess 99.9% enantiomeric purity of the cannabinoids, owing to the high efficiency of the separation. Enantiomers of two monoterpenes, used as intermediates or as starting materials in the chiral synthesis of cannabinoids, were also separated, hence the described procedure is capable of assessing whether the chiral centres in the molecules were sustained throughout the synthetic procedures.
Levin
S
S
Pharmaceutical Chemistry Department, School of Pharmacy, Hebrew University of Jerusalem, Israel.
Abu-Lafi
S
S
Zahalka
J
J
Mechoulam
R
R
D000688:Amylose / Q000031:analogs & derivatives* / Q000737:chemistry; D002186:Cannabinoids / Q000302:isolation & purification*; D002219:Carbamates / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D008968:Molecular Conformation; D048448:Phenylcarbamates; D013237:Stereoisomerism
D002186:Cannabinoids; D002219:Carbamates; D048448:Phenylcarbamates; C080033:Chiralpak AD; D000688:Amylose