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

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|Section7={{Chembox Hazards

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Cannabidiolic acid (CBDA), is a cannabinoid produced in cannabis plants.{{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}} 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.{{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}}

Biosynthesis

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

Decarboxylation

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

References