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
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.

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 

References

  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.
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