Cannabigerolic acid

Cannabigerolic acid
Names
	Preferred IUPAC name 3-[(2E)-3,7-Dimethylocta-2,6-dien-1-yl]-2,4-dihydroxy-6-pentylbenzoic acid
Identifiers
CAS Number	25555-57-1;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:67081;
ChEMBL	ChEMBL463843;
ChemSpider	4952655;
KEGG	C20406;
PubChem CID	6449999;
UNII	80I4ZM847Y;
CompTox Dashboard (EPA)	DTXSID401315426 ;
	InChI InChI=1S/C22H32O4/c1-5-6-7-11-17-14-19(23)18(21(24)20(17)22(25)26)13-12-16(4)10-8-9-15(2)3/h9,12,14,23-24H,5-8,10-11,13H2,1-4H3,(H,25,26)/b16-12+ Key: SEEZIOZEUUMJME-FOWTUZBSSA-N;
	SMILES CCCCCC1=CC(=C(C(=C1C(=O)O)O)C/C=C(\C)/CCC=C(C)C)O;
Properties
Chemical formula	C22H32O4
Molar mass	360.494 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

Biosynthesis of tetrahydrocannabinolic acid (THCA). In the first step, geranyl pyrophosphate and olivetolic acid form cannabigerolic acid, which is then enzymatically rearranged to THCA in the second step.

Cannabigerolic acid (CBGA) is the acidic form of cannabigerol (CBG). It is a dihydroxybenzoic acid and olivetolic acid in which the hydrogen at position 3 is substituted by a geranyl group. It is a biosynthetic precursor to Delta-9-tetrahydrocannabinol, which is the principal psychoactive constituent of the Cannabis plant. It is also a meroterpenoid (i.e. a polyketide and a terpenoid), a member of resorcinols and a phytocannabinoid. It derives from an olivetolic acid. It is a conjugate acid of a cannabigerolate.^[1]

In the Cannabis plant, olivetolic acid and geranyl diphosphate are synthesized into CBGA.^[2]^: 6^[3]^: 17 CBGA is converted in the plant by CBCA synthase, CBDA synthase and THCA synthase into CBCA, CBDA and THCA respectively.^[2]^: 6–7

[1]

[2]

[3]

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