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Cannabigerolic acid

From Wikipedia, the free encyclopedia
Chemical compound
Cannabigerolic acid
Names
Preferred IUPAC name
3-[(2E)-3,7-Dimethylocta-2,6-dien-1-yl]-2,4-dihydroxy-6-pentylbenzoic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
UNII
  • InChI=1S/C22H32O4/c1-5-6-7-11-17-14-19(23)18(21(24)20(17)22(25)26)13-12-16(4)10-8-9-15(2)3/h9,12,14,23-24H,5-8,10-11,13H2,1-4H3,(H,25,26)/b16-12+
    Key: SEEZIOZEUUMJME-FOWTUZBSSA-N
  • CCCCCC1=CC(=C(C(=C1C(=O)O)O)C/C=C(\C)/CCC=C(C)C)O
Properties
C22H32O4
Molar mass360.494 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
Biosynthesis oftetrahydrocannabinolic 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 ofcannabigerol (CBG). It is adihydroxybenzoic acid andolivetolic acid in which the hydrogen at position 3 is substituted by a geranyl group. It is a biosynthetic precursor toDelta-9-tetrahydrocannabinol, which is the principal psychoactive constituent of theCannabis plant. It is also ameroterpenoid (i.e. apolyketide and aterpenoid), a member of resorcinols and aphytocannabinoid. It derives from an olivetolic acid. It is a conjugate acid of a cannabigerolate.[1]

In theCannabis plant, olivetolic acid andgeranyl diphosphate are synthesized into CBGA.[2]: 6 [3]: 17  CBGA is converted in the plant by CBCA synthase,CBDA synthase andTHCA synthase intoCBCA,CBDA andTHCA respectively.[2]: 6–7 

References

[edit]
  1. ^"Cannabigerolic acid".PubChem.United States National Library of Medicine. RetrievedApril 7, 2020.
  2. ^abThomas 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.
Public Domain This article incorporatespublic domain material from websites or documents of theNational Institutes of Health.
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