Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Chemical compound
Biosynthesis of tetrahydrocannabinolic acid (THCA). In the first step, geranyl pyrophosphate and olivetolic acid form cannabigerolic acid, which is then enzymatically rearranged to THCA in the second step.
Cannabigerolic acid (CBGA) is the acidic form of cannabigerol (CBG). It is a dihydroxybenzoic acid and olivetolic acid in which the hydrogen at position 3 is substituted by a geranyl group. It is a biosynthetic precursor to Delta-9-tetrahydrocannabinol, which is the principal psychoactive constituent of the Cannabis plant. It is also a meroterpenoid (i.e. a polyketide and a terpenoid), a member of resorcinols and a phytocannabinoid. It derives from an olivetolic acid. It is a conjugate acid of a cannabigerolate.[1]
In the Cannabis plant, olivetolic acid and geranyl diphosphate are synthesized into CBGA.[2]: 6 [3]: 17 CBGA is converted in the plant by CBCA synthase, CBDA synthase and THCA synthase into CBCA, CBDA and THCA respectively.[2]: 6–7 Afterwards, THCA and CBDA can be decarboxylated into THC and CBD by drying and heating plant material. CBGA has emerging pharmacological properties; for example, it had anticonvulsant effects in a mouse model of Dravet syndrome, a form of epilepsy.[4]
^"Cannabigerolic acid". PubChem. United States National Library of Medicine. Retrieved April 7, 2020.
^ abThomas BF, ElSohly MA (2015). The Analytical Chemistry of Cannabis: Quality Assessment, Assurance, and Regulation of Medicinal Marijuana and Cannabinoid Preparations. Emerging Issues in Analytical Chemistry. Elsevier Science. ISBN 978-0-12-804670-8.
^Degenhardt VF, Stehle F, Kayser O (2016). "The biosynthesis of cannabinoids". In Preedy VR (ed.). Handbook of Cannabis and Related Pathologies: Biology, Pharmacology, Diagnosis, and Treatment. Academic Press. pp. 13–23. ISBN 978-0128008270.
^Anderson LL, Heblinski M, Absalom NL, Hawkins NA, Bowen MT, Benson MJ, et al. (December 2021). "Cannabigerolic acid, a major biosynthetic precursor molecule in cannabis, exhibits divergent effects on seizures in mouse models of epilepsy". British Journal of Pharmacology. 178 (24): 4826–4841. doi:10.1111/bph.15661. PMC 9292928. PMID 34384142. S2CID 236997090.
and 30 Related for: Cannabigerolic acid information
Cannabigerolicacid (CBGA) is the acidic form of cannabigerol (CBG). It is a dihydroxybenzoic acid and olivetolic acid in which the hydrogen at position...
cyclization of cannabidiolic acid but due to studies in the late 1990s it became apparent that its precursor is cannabigerolicacid, which goes through oxidocyclization...
an enzyme responsible for catalyzing the formation of THCA from cannabigerolicacid (CBGA). THCA is the direct precursor of tetrahydrocannabinol (THC)...
plant genus Cannabis. Cannabigerol is the decarboxylated form of cannabigerolicacid, the parent molecule from which other cannabinoids are synthesized...
the amino acid tyrosine. L-tyrosine is converted to p-coumaric acid by the enzyme tyrosine ammonia lyase (TAL). From here, p-coumaric acid is converted...
by stereospecific oxidative cyclization of the geranyl group of cannabigerolicacid according to the following chemical reaction: cannabigerolate + O2...
acid (CBCA) is minor cannabinoid and precursor of cannabichromene. Geranyl pyrophosphate and olivetolic acid combine to produce cannabigerolicacid (CBGA;...
reactive compounds. It is typically stored with a stabilizer in a weakly acidic solution in an opaque bottle. Hydrogen peroxide is found in biological systems...
1998). "Prenylation of olivetolate by a hemp transferase yields cannabigerolicacid, the precursor of tetrahydrocannabinol". FEBS Letters. 427 (2): 283–85...
liquid that gives garlic its distinctive odor. It is a thioester of sulfenic acid. It is also known as allyl thiosulfinate. Its biological activity can be...
tetrahydrocannabinol (THC) is a terpenoid. Hops lack the enzyme that could convert cannabigerolicacid into THC or CBD, but it could be inserted using genetic engineering...
Arachidonic acid (AA, sometimes ARA) is a polyunsaturated omega-6 fatty acid 20:4(ω-6), or 20:4(5,8,11,14). It is formed by biosynthesis from linoleic acid in...
begin as cannabigerolicacid (CBGA). Instead of combining with olivetolic acid to create CBGA, geranyl pyrophosphate joins with divarinolic acid, which...
alcoholic solution of the base in the presence of a little hydrochloric acid gives a characteristic periodide, B2·HI·I2, crystallizing in steel-blue needles...
routes. The fusion of cymol sulfonic acid with caustic potash results in desulfonation. By the action of nitrous acid on 1-methyl-2-amino-4-propyl benzene...
Cannabidiolic acid is biosynthesized by Cannabidiolic acid synthase from the conjugation of olivetolic acid and cannabigerolicacid. CBDA is not produced...
cannabichromenic acid (CBCA, 2-COOH-CBC, CBC-COOH). Geranyl pyrophosphate and olivetolic acid combine to produce cannabigerolicacid (CBGA; the sole intermediate...
called pelargonic acid vanillylamide or PAVA, is an organic compound and a capsaicinoid. It is an amide of pelargonic acid (n-nonanoic acid) and vanillyl...
TRPV group of transient receptor potential family of ion channels. Fatty acid metabolites with affinity for this receptor are produced by cyanobacteria...
CoA to afford caffeic acid. Caffeic acid then undergoes methylation by caffeic acid O-methyltransferase (COMT) to give ferulic acid. Finally, vanillin synthase...
the branched-chain fatty acid pathway. To produce capsaicin, 8-methyl-6-nonenoyl-CoA is produced by the branched-chain fatty acid pathway and condensed with...
hydrolysis with hydrochloric acid, 4-aminophenol reacts in ammonia solution with a phenol derivate, e.g. salicylic acid, to form an indophenol dye under...
tetrahydrocannabinolic acid (THCA, 2-COOH-THC). Geranyl pyrophosphate and olivetolic acid react, catalysed by an enzyme to produce cannabigerolicacid, which is cyclized...
1998). "Prenylation of olivetolate by a hemp transferase yields cannabigerolicacid, the precursor of tetrahydrocannabinol". FEBS Letters. 427 (2): 283–285...
organic compound with the formula C8H8O3. It is the methyl ester of salicylic acid. It is a colorless, viscous liquid with a sweet, fruity odor reminiscent...
rise to trans-cinnamic acid. In the second step, 4-coumarate–CoA ligase (4CL) converts cinnamic acid to cinnamoyl-CoA by an acid–thiol ligation. 4CL uses...
canister, in a liquid stream. It contains a 0.3% solution of pelargonic acid vanillylamide (PAVA), also called nonivamide, a synthetic capsaicinoid (analogue...
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