Cannabidiolic acid: Difference between revisions

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;
	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

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Cannabidiolic acid (CBDA), is a cannabinoid produced 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 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 a loss of one carbon and two oxygen atoms acetyl from the 1 position of the benzoic acid 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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[2]

[3]

@@ Line 1: / Line 1: @@
 {{Chembox
-|IUPACName=2,4-Dihydroxy-3-[(1''R'',6''R'')-3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-yl]-6-pentylbenzoic acid
 |ImageFile=Cannabidiolic acid.svg
+|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
@@ Line 22: / Line 22: @@
  }}
 }}
-'''Cannabidiolic acid''', also known as '''CBDA''', is a [[cannabinoid]] found 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 most abundant in the glandular [[Trichome|trichomes]] on the female seedless flowers or more accurately [[Infructescence| infructescence]] often colloquially refered to as buds.<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|language=en|volume=n/a|issue=n/a|pages=37–56|doi=10.1111/tpj.14516|pmid=31469934|issn=1365-313X|doi-access=free}}</ref> CBDA is the chemical precursor to [[cannabidiol]] (CBD). Through the process of [[decarboxylation]]  cannabidol is derived via a loss of a carbon and two oxygen atoms from the 1 positon of the benzoic acid ring.
+'''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 most abundant in the glandular [[trichome]]s 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==
-==Chemical composition==
-Cannabidiolic acid is biosynthesized by [[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>
+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 a loss of one carbon and two oxygen atoms [[acetyl]] from the 1 position of the benzoic acid ring.
 ==References==
 {{Reflist}}
+{{Cannabinoids}}
 [[Category:Benzoic acids]]
 [[Category:Cannabinoids]]
+[[Category:2,6-Dihydroxybiphenyls]]
+[[Category:Dihydroxybenzoic acids]]