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	25555-57-1
ChEBI	CHEBI:67081
ChEMBL	ChEMBL463843
ChemSpider	4952655
KEGG	C20406
PubChem CID	6449999
UNII	80I4ZM847Y
CompTox Dashboard (EPA)	DTXSID401315426
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 diterpenoid, a polyketide, a member of resorcinols and a phytocannabinoid. It derives from an olivetolic acid. It is a conjugate acid of a cannabigerolate.

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

References

Sources

• "Compound Summary – cannabigerolic acid". PubChem. United States National Library of Medicine. Retrieved April 7, 2020.
• Thomas, Brian F.; ElSohly, Mahmoud A. (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, F.; Stehle, F.; Kayser, O. (2016). "The biosynthesis of cannabinoids". In Preedy, Victor R. (ed.). Handbook of Cannabis and Related Pathologies: Biology, Pharmacology, Diagnosis, and Treatment. Academic Press. pp. 13–23. ISBN 978-0128008270.

Further reading

• Havelka, Jacqueline (September 9, 2019). "What is CBGA (Cannabigerolic Acid) & what does this cannabinoid do?". Leafly.

 This article incorporates public domain material from websites or documents of the National Institutes of Health.