Cannabidiolic acid

Chemical compound From Wikipedia, the free encyclopedia

Cannabidiolic acid (CBDA), is a cannabinoid produced in cannabis plants.[1] It is the precursor to cannabidiol (CBD). It is most abundant in the glandular trichomes on the female seedless flowers or more accurately infructescence often colloquially referred to as buds or flowers.[2]

Quick facts Names, Identifiers ...
Cannabidiolic acid
Names
Preferred IUPAC name
(1′R,2′R)-2,6-Dihydroxy-5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro[1,1′-biphenyl]-3-carboxylic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
UNII
  • InChI=1S/C22H30O4/c1-5-6-7-8-15-12-18(23)20(21(24)19(15)22(25)26)17-11-14(4)9-10-16(17)13(2)3/h11-12,16-17,23-24H,2,5-10H2,1,3-4H3,(H,25,26)/t16-,17+/m0/s1
    Key: WVOLTBSCXRRQFR-DLBZAZTESA-N
  • CCCCCC1=CC(=C(C(=C1C(=O)O)O)[C@@H]2C=C(CC[C@H]2C(=C)C)C)O
Properties
C22H30O4
Molar mass 358.478 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Biosynthesis

Cannabidiolic acid is a natural product sesquiterpene biosynthesized in cannabis via Cannabidiolic acid synthase from the conjugation of olivetolic acid and cannabigerolic acid.[3]

Decarboxylation

CBDA is the chemical precursor to cannabidiol (CBD). Through the process of decarboxylation, cannabidiol is derived through loss of the carbon and two oxygen atoms that make up the carboxylic acid moeity on the aromatic ring.

References

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