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Cannabigerolic acid

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Cannabigerolic acid
Names
IUPAC name
3-[(2E)-3,7-dimethylocta-2,6-dienyl]-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 that is olivetolic acid in which the hydrogen at position 3 is substituted by a geranyl group. A biosynthetic precursor to Delta(9)-tetrahydrocannabinol, the principal psychoactive constituent of the Cannabis plant. It is a dihydroxybenzoic acid, 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]

In the Cannabis plant, olivetolic acid and geranyl diphosphate are synthesized into CBGA.[2][3] CBGA is converted in the plant by CBCA synthase, cannabidiolic acid synthase (CBDA synthase) and tetrahydrocannabinolic acid synthase (THCA synthase) into CBCA, CBDA and tetrahydrocannabinolic acid (THCA).[4] THCA can be decarboxylated into THC by drying and heating plant material.

References

  1. ^ PubChem 2020.
  2. ^ Thomas & ElSohly 2015, p. 6.
  3. ^ Degenhardt, Stehle & Kayser 2016, p. 17.
  4. ^ Thomas & ElSohly 2015, pp. 6–7.

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


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