Cannabidiolic acid

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
CAS Number
  • 1244-58-2
3D model (JSmol)
  • Interactive image
3DMet
  • B04205
ChEBI
  • CHEBI:3359
ChEMBL
  • ChEMBL498672
ChemSpider
  • 141099
KEGG
  • C10784
PubChem CID
  • 160570
UNII
  • FJX8O3OJCD
CompTox Dashboard (EPA)
  • DTXSID80154318
InChI
  • 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
Chemical formula
 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).
Infobox references
Chemical compound

Cannabidiolic acid (CBDA), is a cannabinoid found in cannabis plants.[1] It is most abundant in the glandular trichomes on the female seedless flowers or more accurately infructescence often colloquially referred to as buds.[2] CBDA is the chemical precursor to cannabidiol (CBD). Through the process of decarboxylation cannabidiol is derived via a loss of a carbon and two oxygen atoms from the 1 position of the benzoic acid ring. Cannabinoids are a class of compounds that are essentially unique to the cannabis genus.  Both marijuana and hemp belong to this genus.

Chemical composition

Cannabidiolic acid is biosynthesized by Cannabidiolic acid synthase from the conjugation of olivetolic acid and cannabigerolic acid.[3] CBDA is not produced by man but is naturally occurring in hemp.  It is a raw compound which is found in the flowering buds of the female cannabis plant.[4]

References

  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. Retrieved 2019-12-23.
  4. ^ Nadel, David (2020-10-02). "Hemp Compound Spotlight: CBDA". Pure CBD Now. Retrieved 2022-12-18.