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;
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;
	SMILES 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

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]

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

^ 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.
^ 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.
^ PubChem. "Cannabidiolic acid". pubchem.ncbi.nlm.nih.gov. Retrieved 2019-12-23.

[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.

[:0-3] PubChem. "Cannabidiolic acid". pubchem.ncbi.nlm.nih.gov. Retrieved 2019-12-23.

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