Cannabidiorcol

Cannabidiorcol
Identifiers
	IUPAC name 5-methyl-2-[(1R,6R)-3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-yl]benzene-1,3-diol;
CAS Number	35482-50-9;
PubChem CID	16657068;
ChemSpider	17590348;
UNII	259WR5E2RF;
Chemical and physical data
Formula	C17H22O2
Molar mass	258.361 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC1=C[C@H]([C@@H](CC1)C(=C)C)C2=C(C=C(C=C2O)C)O;
	InChI InChI=1S/C17H22O2/c1-10(2)13-6-5-11(3)7-14(13)17-15(18)8-12(4)9-16(17)19/h7-9,13-14,18-19H,1,5-6H2,2-4H3/t13-,14+/m0/s1; Key:GKVOVXWEBSQJPA-UONOGXRCSA-N;

Cannabidiorcol (CBDO, CBD-C1, O-1821) is a phytocannabinoid found naturally in Cannabis in trace concentrations. It is related to cannabidiol, with the pentyl side chain shortened to a methyl group. Cannabidiorcol has low affinity for cannabinoid receptors and is mainly active as an agonist of the TRPV2 cation channel, through which it produces antiinflammatory effects,^[1] but can also promote tumorigenesis at high concentrations.^[2]

References

^ Laragione T, Harris C, Gulko PS (March 2023). "Combination therapy of a TRPV2 agonist with a TNF inhibitor achieves sustained suppression of disease severity and reduced joint damage". Clinical and Experimental Immunology. 211 (3): 233–238. doi:10.1093/cei/uxac124. PMC 10038320. PMID 36571199.
^ Huang R, Li S, Tian C, Zhou P, Zhao H, Xie W, et al. (November 2022). "Thermal stress involved in TRPV2 promotes tumorigenesis through the pathways of HSP70/27 and PI3K/Akt/mTOR in esophageal squamous cell carcinoma". British Journal of Cancer. 127 (8): 1424–1439. doi:10.1038/s41416-022-01896-2. PMC 9553907. PMID 35896815.

[pmid36571199-1] Laragione T, Harris C, Gulko PS (March 2023). "Combination therapy of a TRPV2 agonist with a TNF inhibitor achieves sustained suppression of disease severity and reduced joint damage". Clinical and Experimental Immunology. 211 (3): 233–238. doi:10.1093/cei/uxac124. PMC 10038320. PMID 36571199.

[pmid35896815-2] Huang R, Li S, Tian C, Zhou P, Zhao H, Xie W, et al. (November 2022). "Thermal stress involved in TRPV2 promotes tumorigenesis through the pathways of HSP70/27 and PI3K/Akt/mTOR in esophageal squamous cell carcinoma". British Journal of Cancer. 127 (8): 1424–1439. doi:10.1038/s41416-022-01896-2. PMC 9553907. PMID 35896815.

[1]

[2]

Identifiers

IUPAC name 5-methyl-2-[(1R,6R)-3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-yl]benzene-1,3-diol
CAS Number	35482-50-9
PubChem CID	16657068
ChemSpider	17590348
UNII	259WR5E2RF
Chemical and physical data
Formula	C₁₇H₂₂O₂
Molar mass	258.361 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CC1=C[C@H]([C@@H](CC1)C(=C)C)C2=C(C=C(C=C2O)C)O
InChI InChI=1S/C17H22O2/c1-10(2)13-6-5-11(3)7-14(13)17-15(18)8-12(4)9-16(17)19/h7-9,13-14,18-19H,1,5-6H2,2-4H3/t13-,14+/m0/s1 Key:GKVOVXWEBSQJPA-UONOGXRCSA-N

Cannabidiorcol

See also

References