Cannabigerolic acid

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 diterpenoid, a polyketide, a member of resorcinols and a phytocannabinoid. It derives from an olivetolic acid. It is a conjugate acid of a cannabigerolate.[1]

Cannabigerolic acid
Names
Preferred IUPAC name
3-[(2E)-3,7-Dimethylocta-2,6-dien-1-yl]-2,4-dihydroxy-6-pentylbenzoic acid
Identifiers
CAS Number
ChEBI
ChEMBL
ChemSpider
KEGG
PubChem CID
UNII
Properties
Chemical formula
 C22H32O4
Molar mass 360.494 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
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.

In the Cannabis plant, olivetolic acid and geranyl diphosphate are synthesized into CBGA.[2][3] CBGA is converted in the plant by CBCA synthase, CBDA synthase and THCA synthase into CBCA, CBDA and THCA respectively.[4] 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.[5]

References
  1. PubChem 2020.
  2. Thomas & ElSohly 2015, p. 6.
  3. Degenhardt, Stehle & Kayser 2016, p. 17.
  4. Thomas & ElSohly 2015, pp. 6–7.
  5. Anderson, LL; Heblinski, M; Absalom, NL; Hawkins, NA; Bowen, MT; Benson, MJ; Zhang, F; Bahceci, D; Doohan, PT; Chebib, M; McGregor, IS; Kearney, JA; Arnold, JC (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. ISSN 0007-1188. PMID 34384142. S2CID 236997090.

Sources

Further reading
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