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

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]

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]^: 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

^ "Cannabigerolic acid". PubChem. United States National Library of Medicine. Retrieved April 7, 2020.
^ ^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.
^ 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.

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

[1] "Cannabigerolic acid". PubChem. United States National Library of Medicine. Retrieved April 7, 2020.

[Thomas_2015-2] 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.

[Degenhardt_2016-3] 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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