Cannabigerolic acid

The lUPAC name of cannabidiol is 2-[(lS, 6iI)-3-methyl-6-prop-l-en-2-yl-l-cyclohex-2-enyl]-5-pentyl-benzene-1,3-diol. Cannabidiol (CBD, 2.9) in its acidic form cannabidiolic acid (CBDA, 2.10) is the second major cannabinoid in C. sativa besides A9-THC. As already mentioned for A9-THC, variations in the length of the side chain are also possible for CBD. Important in this context are the propyl side chain-substituted CBD, named cannabidivarin (CBDV, 2.11), and CBD-C4 (2.12), the homologous compound with a butyl side chain. Related to the synthesis starting from CBD to A9-THC as described in Sect. 3.1, it was accepted that CBDA serves as a precursor for THCA in the biosynthesis. Recent publications indicate that CBDA and THCA are formed from the same precursor, cannabigerolic acid (CBGA), and that it is unlikely that the biosynthesis of THCA from CBDA takes place in C. sativa. 

Several additional, non-psychotropic cannabinoids were also identified at that time. The best known are cannabigerol (CBG), cannabichromene (CBC) and cannabicyclol. Cannabinolic acid (CBNA) and cannabigerolic acid (CBGA) were also identified,followed by two... 

Mechoulam R, Gaoni Y, The isolation and structure of cannabinolic, cannabid-iolic and cannabigerolic acids. Tetrahedron 21 1223-1229, 1965. 

Shoyama Y, Yamauchi T, Nishioka I, Cannabis. 5. Cannabigerolic acid monomethyl ether and cannabinoHc acid, Chem Pharm Bull 18 1327—1332, 1970. 

Taura F, Morimoto S, Shoyama Y, Purification and characterization of cannabidiolic-acid synthase from Cannabis sativa L. Biochemical analysis of a novel enzyme that catalyzes the oxidocyclization of cannabigerolic acid to cannabidiolic 2lcsA, J Biol Chem 271 17411—17416, 1996. 

Cannabielsoin, C-3 Resin Cannabielsoin P1CS172 Cannabifuran, dehydro Resin , Pl snz Cannabifuran Pl snz Resin Cannabigerol monomethyl ether Pl siZZ Cannabigerol Resin ° , Pl s i i Cannabigerolic acid monoethyl ether ... 

The oxidocyclization of cannabigerolic acid to tetrahydrocannabinolic acid is catalyzed by tetrahydrocannabinolic... 

Fellermeier, M. and Zenk, M.H. (1998) Prenylation of olivetolateby a hemp transferase yields cannabigerolic acid, the precursor of tetrahydrocannabinol. FEES Lett., 427, 283-85. 

THC is made in the leaves of the cannabis plant, the first step being the biosynthesis of A-9-tetrahydrocannabinolic acid (THCA) from cannabigerolic acid (GBGA). A living plant contains very little A -THG, but THGA readily eliminates carbon dioxide to form A -THG, even by just drying the plant. 

The latter alternative was applied to the syntheses of [l- C]cannabigerolic acid and A -6a,10a-tranr-tetrahydro[2,4- Cj]cannabinol (3721 (Figure 6.111). In the first case, oxidation of367 = H, = C5H11) was achieved in a two-step process by treatment... 

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