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Cannabidiolic acid

From Wikipedia, the free encyclopedia
"CBDA" redirects here. For other uses, seeConfederação Brasileira de Desportos Aquáticos.
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 mass358.478 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

Cannabidiolic acid (CBDA), is acannabinoid produced incannabis plants.[1] It is theprecursor tocannabidiol (CBD). It is most abundant in the glandulartrichomes on the female seedless flowers or more accuratelyinfructescence often colloquially referred to as buds or flowers.[2]

Biosynthesis

[edit]

Cannabidiolic acid is a natural productsesquiterpene biosynthesized incannabis viaCannabidiolic acid synthase from the conjugation ofolivetolic acid andcannabigerolic acid.[3]

Decarboxylation

[edit]

CBDA is the chemical precursor tocannabidiol (CBD). Through the process ofdecarboxylation cannabidiol is derived through a loss of one carbon and two oxygen atomsacetyl from the 1 position of the benzoic acid ring.

References

[edit]
  1. ^Takeda, Shuso (2013)."[Medicinal chemistry and pharmacology focused on cannabidiol, a major component of the fiber-type cannabis]".Yakugaku Zasshi: Journal of the Pharmaceutical Society of Japan.133 (10):1093–1101.doi:10.1248/yakushi.13-00196.ISSN 1347-5231.PMID 24088353.
  2. ^Livingston, Samuel J.; Quilichini, Teagen D.; Booth, Judith K.; Wong, Darren C. J.; Rensing, Kim H.; Laflamme‐Yonkman, Jessica; Castellarin, Simone D.; Bohlmann, Joerg; Page, Jonathan E.; Samuels, A. Lacey (2020)."Cannabis glandular trichomes alter morphology and metabolite content during flower maturation".The Plant Journal.101 (1):37–56.doi:10.1111/tpj.14516.ISSN 1365-313X.PMID 31469934.
  3. ^PubChem."Cannabidiolic acid".pubchem.ncbi.nlm.nih.gov. Retrieved2019-12-23.
Phytocannabinoids
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Cannabibutols
Cannabichromenes
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Retrieved from "https://en.wikipedia.org/w/index.php?title=Cannabidiolic_acid&oldid=1271215941"
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