Cannabidiol diacetate

Cannabidiol diacetate
Identifiers
	IUPAC name [3-acetyloxy-2-[(1R,6R)-3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-yl]-5-pentylphenyl] acetate;
PubChem CID	15139512;
Chemical and physical data
Formula	C25H34O4
Molar mass	398.543 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCCCCC1=CC(=C(C(=C1)OC(=O)C)[C@@H]2C=C(CC[C@H]2C(=C)C)C)OC(=O)C;
	InChI InChI=1S/C25H34O4/c1-7-8-9-10-20-14-23(28-18(5)26)25(24(15-20)29-19(6)27)22-13-17(4)11-12-21(22)16(2)3/h13-15,21-22H,2,7-12H2,1,3-6H3/t21-,22+/m0/s1; Key:UCYSPYOYJNVCAI-FCHUYYIVSA-N;

Cannabidiol diacetate (CBD-di-O-Acetate, CBD-DO) is a semi-synthetic derivative of cannabidiol derived by acetylation of the OH groups,^[1] which presumably acts as a prodrug for CBD. It has been found as a component of grey-market cannabis products such as e-cigarette liquids and edible gummy lollies.^[2]

References

^ Appendino G, Gibbons S, Giana A, Pagani A, Grassi G, Stavri M, Smith E, Rahman MM (August 2008). "Antibacterial cannabinoids from Cannabis sativa: a structure-activity study". Journal of Natural Products. 71 (8): 1427–30. doi:10.1021/np8002673. PMID 18681481.
^ Holt AK, Poklis JL, Peace MR (October 2022). "∆8-THC, THC-O Acetates and CBD-di-O Acetate: Emerging Synthetic Cannabinoids Found in Commercially Sold Plant Material and Gummy Edibles". Journal of Analytical Toxicology. 46 (8): 940–948. doi:10.1093/jat/bkac036. PMC 9564187. PMID 35674405.

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[pmid18681481-1] Appendino G, Gibbons S, Giana A, Pagani A, Grassi G, Stavri M, Smith E, Rahman MM (August 2008). "Antibacterial cannabinoids from Cannabis sativa: a structure-activity study". Journal of Natural Products. 71 (8): 1427–30. doi:10.1021/np8002673. PMID 18681481.

[pmid35674405-2] Holt AK, Poklis JL, Peace MR (October 2022). "∆8-THC, THC-O Acetates and CBD-di-O Acetate: Emerging Synthetic Cannabinoids Found in Commercially Sold Plant Material and Gummy Edibles". Journal of Analytical Toxicology. 46 (8): 940–948. doi:10.1093/jat/bkac036. PMC 9564187. PMID 35674405.

[1]

[2]

Cannabidiol diacetate

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Identifiers

IUPAC name [3-acetyloxy-2-[(1R,6R)-3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-yl]-5-pentylphenyl] acetate
PubChem CID	15139512
Chemical and physical data
Formula	C₂₅H₃₄O₄
Molar mass	398.543 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CCCCCC1=CC(=C(C(=C1)OC(=O)C)[C@@H]2C=C(CC[C@H]2C(=C)C)C)OC(=O)C
InChI InChI=1S/C25H34O4/c1-7-8-9-10-20-14-23(28-18(5)26)25(24(15-20)29-19(6)27)22-13-17(4)11-12-21(22)16(2)3/h13-15,21-22H,2,7-12H2,1,3-6H3/t21-,22+/m0/s1 Key:UCYSPYOYJNVCAI-FCHUYYIVSA-N

Cannabidiol diacetate

See also

References

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