Cannabidiolic acid

{{Redirect|CBDA||Confederação Brasileira de Desportos Aquáticos}} {{Chembox |ImageFile=Cannabidiolic acid.svg | ImageClass = skin-invert-image |PIN=(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 |Section1={{Chembox Identifiers | CASNo = 1244-58-2 | PubChem = 160570 | ChemSpiderID = 141099 | KEGG = C10784 | ChEBI = 3359 | 3DMet = B04205 | ChEMBL = 498672 | UNII = FJX8O3OJCD | DTXSID = DTXSID80154318 | StdInChI=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 | StdInChIKey = WVOLTBSCXRRQFR-DLBZAZTESA-N | SMILES = CCCCCC1=CC(=C(C(=C1C(=O)O)O)[C@@H]2C=C(CC[C@H]2C(=C)C)C)O }} |Section2={{Chembox Properties |C=22|H=30|O=4 }} |Section7={{Chembox Hazards }} }} '''Cannabidiolic acid''' ('''CBDA'''), is a cannabinoid produced in cannabis plants.<ref>{{Cite journal|last=Takeda|first=Shuso|date=2013|title=[Medicinal chemistry and pharmacology focused on cannabidiol, a major component of the fiber-type cannabis]|journal=Yakugaku Zasshi: Journal of the Pharmaceutical Society of Japan|volume=133|issue=10|pages=1093–1101|doi=10.1248/yakushi.13-00196|issn=1347-5231|pmid=24088353|doi-access=free}}</ref> 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.<ref>{{Cite journal|last1=Livingston|first1=Samuel J.|last2=Quilichini|first2=Teagen D.|last3=Booth|first3=Judith K.|last4=Wong|first4=Darren C. J.|last5=Rensing|first5=Kim H.|last6=Laflamme‐Yonkman|first6=Jessica|last7=Castellarin|first7=Simone D.|last8=Bohlmann|first8=Joerg|last9=Page|first9=Jonathan E.|last10=Samuels|first10=A. Lacey|title=Cannabis glandular trichomes alter morphology and metabolite content during flower maturation|journal=The Plant Journal|year=2020|volume=101|issue=1 |language=en|pages=37–56|doi=10.1111/tpj.14516|pmid=31469934|issn=1365-313X|doi-access=free}}</ref>

==Biosynthesis==

Cannabidiolic acid is a natural product sesquiterpene biosynthesized in cannabis via Cannabidiolic acid synthase from the conjugation of olivetolic acid and cannabigerolic acid.<ref name=":0">{{Cite web|url=https://pubchem.ncbi.nlm.nih.gov/compound/160570|title=Cannabidiolic acid|last=PubChem|website=pubchem.ncbi.nlm.nih.gov|language=en|access-date=2019-12-23}}</ref>

==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== {{Reflist}}

{{Cannabinoids}}

Category:Benzoic acids Category:Cannabinoids Category:Resorcinols Category:Dihydroxybenzoic acids Category:Cyclohexenes