MOLECULE

Cannabichromenic acid

Cannabichromenic acid (CBCA) is a biosynthetic derivative of cannabigerolic acid (CBGA). It is a non-psychoactive component of cannabis and is one of the more than 100 cannabinoids found in Cannabis sativa plants. As its precursor, cannabigerolic acid, CBCA is a phytocannabinoid that belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Cannabichromenic acid is characterized by the presence of a chromene moiety in the center of the structure. This chromene arrangement results from the cyclization of the isoprenoid sidechain on to the hydroxyl group in position four of cannabigerolic acid, yielding a pyrane type ring. Cannabichromenic acid is a molecule of mixed biosynthetic origin, in which its aromatic moiety (derived from olivetolic acid) occurs through the polyketide biosynthetic pathway while the prenylated sidechain derives from the MEP pathway of the terpenoids (DOI: 10.1016/B978-0-12-800756-3.00002-8). As such, cannabichromenic acid can be considered a polyketide, a monoterpenoid and a resorcinol, due to the meta arrangement of its two hydroxyl groups on the benzene ring. CBC is not active at the  cannabinoid-1 (CB1) and cannabinoid-2 (CB2) receptors, but is an agonist of  transient receptor potential ankyrin 1 TRPA1 and less potently, an agonist of  transient receptor potential cation channel, subfamily V, member 3 and 4 (TRPV3;  TRPV4;  PMID 28120231).