Cannabichromenic acid

Among THCA and CBDA, cannabichromene (CBC, 2.15) and the acidic form cannabichromenic acid (CBCA, 2.16) are formed from their common precursor CBGA. Besides CBC, its homologous compoimd cannabiverol (CBCV, 2.17) with a propyl side chain is also present in plants. 

Morimoto S, Komatsu K, Taura F, Shoyama Y, Enzymological evidence for cannabichromenic acid biosynthesis,60 854—857, 1997. 

CS073 Morimoto, S., K. Komatsu, F. Taura and Y. Shoyama. Enzymological evidence for cannabichromenic acid biosynthesis. J Nat Prod 1997 60(8) ... 

In the 1970s the biosynthesis of cannabinoids was investigated with radiolabeling experiments. 14C-labeled mevalonate and malonate were shown to be incorporated into tetrahydrocannabinolic acid and cannabichromenic acid at very low rates (< 0.02%). Until 1990 the precursors of all terpenoids, isopentenyl diphosphate and dimethyl-allyl diphosphate were believed to be biosynthesized via the mevalonate pathway. Subsequent studies, however, proved that many plant terpenoids are biosynthesized via the recently discovered deoxyxylulose phosphate pathway (Eisenreich et al., 1998 Rohmer, 1999). It was shown that the Cio-terpenoid moiety of cannabinoids is biosynthesized entirely or predominantly (>98%) via this pathway (Fellermeister et al., 2001). The phenolic moiety is generated by a polyketide-type reaction sequence. 

Most of the natural 2,2-dialkylchromenes arc derived from a single C5 isoprenoid chain (3, R = R = Me). Recently, however, some poly-isoprenoid cliromencs have been isolated gambogic acid (13),74 flemingins (14,)75 cannabichromene (15) and cannabichromenic acid... 

Canadensolide H NMR, 4, 578 Cannabichromanone synthesis, 3, 726 Cannabichromene, 3, 675 photochemistry, 3, 721 synthesis, 3, 721, 746, 748, 782 Cannabichromenic acid thermolysis, 3, 721 Cannabifuran synthesis, 4, 698 Cannabinoids biosynthesis, 3, 877 structure, 4, 548 thermolysis, 3, 721 Cannabinol occurrence, 3, 665 as pharmaceutical, 1, 151 synthesis, 3, 721, 786 Cannabinol, hexahydro-synthesis, 3, 787 Cannabinol, A -tetrahydro-occurrence, 3, 718 thermolysis, 3, 721 Cannabinol, All6-tetrahydro-metabolism, 1, 239 Cannabinol, 3,4-cis-A1,2-tetrahydro-synthesis, 3, 782... 

The formation of cannabidiolic acid and cannabichromenic acid takes place independently on other oxidoreductases. Cannabidiolic acid is the main can-nabinoid in fibre hemp. Cannabichromenic acid is also produced in drug hemp. In contrast to other cannabinoids, it is produced as a 5 1 mixture of enantiomers. Therefore, seen from the genetic standpoint, the expression of the cannabidiolic acid synthase or of the tetrahydrocannabinolic acid synthase determines if the phenotype correlates with drug or fibre hemp. 

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