(6aR,10aR)-1-hydroxy-6,6-dimethyl-3-pentyl-6H,6aH,7H,10H,10aH-benzo[c]isochromene-9-carboxylic acid

• ChemBase ID: 131225
• Molecular Formular: C21H28O4
• Molecular Mass: 344.44462
• Monoisotopic Mass: 344.19875938
• SMILES: CCCCCc1cc(c2c(c1)OC([C@H]1[C@H]2CC(=CC1)C(=O)O)(C)C)O
• Canonical SMILES: CCCCCc1cc(O)c2c(c1)OC([C@H]1[C@H]2CC(=CC1)C(=O)O)(C)C
• InChI: InChI=1S/C21H28O4/c1-4-5-6-7-13-10-17(22)19-15-12-14(20(23)24)8-9-16(15)21(2,3)25-18(19)11-13/h8,10-11,15-16,22H,4-7,9,12H2,1-3H3,(H,23,24)/t15-,16-/m1/s1
• InChIKey: OGXXAQFMAFTSRU-HZPDHXFCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6aR,10aR)-1-hydroxy-6,6-dimethyl-3-pentyl-6H,6aH,7H,10H,10aH-benzo[c]isochromene-9-carboxylic acid
• IUPAC Traditional name: (6aR,10aR)-1-hydroxy-6,6-dimethyl-3-pentyl-6aH,7H,10H,10aH-benzo[c]isochromene-9-carboxylic acid
• Synonyms: 11-Nor-Δ8-tetrahydrocannabinol-9-carboxylic acid; 9-Carboxy-11-nor-Δ8-tetrahydrocannabinol; Δ1(6)-Tetrahydrocannabinol-7-oic Acid; Δ6-Tetrahydrocannabinol-7-oic Acid; Δ8-THC-11-oic Acid; Δ8-Tetrahydro Cannabinol-11-oic Acid; (6aR,10aR)-6a,7,10,10a-Tetrahydro-1-hydroxy-6,6-dimethyl-3-pentyl-6H-dibenzo[b,d]pyran-9-carboxylic Acid; (6aR-trans)-6a,7,10,10a-Tetrahydro-1-hydroxy-6,6-dimethyl-3-pentyl-6H-dibenzo[b,d]pyran-9-carboxylic Acid; (-)-9-Nor-9-carboxy-Δ8-tetrahydrocannabinol; 11-Nor-Δ8-Tetrahydrocannabinol-8-carboxylic Acid; Δ6-四氢大麻酚-7-酸; 9-羧基-11-去甲基-Δ8-四氢大麻酚; 11-去甲基-Δ8-四氢大麻酚-9-羧酸

Database IDs

• CAS Number: 39690-06-7
• MDL Number: MFCD00135975
• PubChem SID: 162225503
• PubChem CID: 162389

CALCULATED PROPERTIES

• Acid pKa: 4.2535286
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 3.867675
• LogD (pH = 7.4): 2.1385074
• Log P: 5.1358495
• Molar Refractivity: 98.4507 cm^3
• Polarizability: 37.888184 Å^3
• Polar Surface Area: 66.76 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Drug Control: USDEA Schedule I; regulated under CDSA - not available from Sigma-Aldrich Canada
• Storage Temperature: -20°C

DETAILS

Sigma Aldrich - N4641

Application
用于鉴定 THC 代谢物的标准品。

Toronto Research Chemicals - T293245

Δ8-Tetrahydro Cannabinol-11-oic acid is a derivative of Δ8-Tetrahydrocannabinol (T293240) used for decreasing cell proliferation in a mammal (cancer treatment).

REFERENCES

• Hammett-Stabler, C., et al.: Clin. Chim. Acta, 315, 125 (2002)
• Wu, A., et al.: J. Anal. Toxicol., 17, 241 (2002)
• Ferrara, S., et al.: J. Anal. Toxicol., 18, 278 (2002)