Cannabigerolic acid

Cannabigerolic acid
Names
Preferred IUPAC name
3-[(2E)-3,7-Dimethylocta-2,6-dien-1-yl]-2,4-dihydroxy-6-pentylbenzoic acid
Identifiers
ChEBI
ChEMBL
ChemSpider
KEGG
UNII
Properties
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).
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]

  1. ^ "Cannabigerolic acid". PubChem. United States National Library of Medicine. Retrieved April 7, 2020.
  2. ^ a b Thomas 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.
  3. ^ 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.
  4. ^ 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.