20408-52-0

Usage

InChI:InChI=1/C22H30O4/c1-5-6-7-10-16-14-18-17(20(23)19(16)21(24)25)11-13-22(4,26-18)12-8-9-15(2)3/h9,11,13-14,23H,5-8,10,12H2,1-4H3,(H,24,25)

Upstream product

• 25555-57-1 CBGA 
• 763-10-0 geranyl diphosphate 
• 112639-01-7 2-bromo-1,5-dimethoxy-3-pentyl-benzene 
• 855875-40-0 2,4-dihydroxyl-6-pentylbenzaldehyde 
• 20469-65-2 1-bromo-3,5-dimethoxybenzene 
• 110-53-2 1-Bromopentane 
• 22976-40-5 1,3-dimethoxy-5-pentylbenzene 

Downstream Products

• 20675-51-8 cannabichromene 

Relevant academic research and scientific papers

Purification and characterization of cannabichromenic acid synthase from Cannabis sativa

Cannabichromenic acid synthase was purified to apparent homogeneity by sequential column chromatography including DEAE-cellulose, phenyl-Sepharose CL-4B, and hydroxylapatite. The enzyme catalysed the oxidocyclization of cannabigerolic acid and cannabinerolic acid to cannabichromenic acid. The K(m) values for both substrates were in the same order of magnitude although the V(max) value for the former was higher than that for the latter. These results suggested that cannabichromenic acid is predominantly formed from cannabigerolic acid rather than cannabinerolic acid. The enzyme required neither molecular oxygen nor hydrogen peroxide, indicating that the cannabichromenic acid synthase reaction proceeds through direct dehydrogenation without hydroxylation.

Enzymological evidence for cannabichromenic acid biosynthesis

An enzyme involved in the biosynthesis of cannabichromenic acid was identified in young leaves of Cannabis sativa. The enzyme, named cannabichromenic acid synthase, catalyzed the oxidocyclization of cannabigerolic acid to cannabichromenic acid. The biosynthetic mechanism for the formation of cannabichromenic acid was similar to those of Δ1- tetrahydrocar nabinolic acid and cannabidiolic acid.

METHODS FOR SYNTHESIS OF CANNABINOID COMPOUNDS

The present invention provides simple synthetic routes for the preparation of cannabinoid compounds such as CBD, CBDV, THC, THCV, CBN, HU-308, CBG, CBC, and derivatives thereof, which are stereoselective and provide the desired cannabinoid compound in high yield.

CANNABICHROMENIC ACID SYNTHASE FROM CANNABIS SATIVA

Nucleic acid molecules from cannabis have been isolated and characterized and encode polypeptides having cannabichromenic acid synthase activity. Expression or over-expression of the nucleic acids alters levels of cannabinoid compounds. The polypeptides may be used in vivo or in vitro to produce cannabinoid compounds.