Cannabichromene (CBC) is unusual among cannabinoids in having been described as both a racemic and scalemic compound from natural Cannabis sources. Several explanations are available for this circumstance, including facile racemization. Using modern synthetic biology, cannabichromene was obtained in scalemic form and the enantiomer matching the major Cannabis-derived CBC was identified. To preclude racemization, it was converted to cannabicyclol for stereochemical analysis. This permitted the (R) absolute stereochemistry to be assigned to natural CBC based on chiroptical data for related natural products and the absolute configuration of a cannabicyclol analog determined by x-ray crystallography. The racemization of CBC was found to be rather slow in the laboratory, but handling practices for natural cannabis products do seem able to promote the process.

Cannabichromene and congeners via synthetic biology

ACS Spring Meeting 2021

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.