ethyl (6aR,10aR)-1-hydroxy-6,6-dimethyl-3-pentyl-6H,6aH,7H,8H,10aH-benzo[c]isochromene-9-carboxylate

• ChemBase ID: 175717
• Molecular Formular: C23H32O4
• Molecular Mass: 372.49778
• Monoisotopic Mass: 372.2300595
• SMILES: C1(=C[C@@H]2[C@@H](CC1)C(Oc1c2c(cc(c1)CCCCC)O)(C)C)C(=O)OCC
• Canonical SMILES: CCCCCc1cc(O)c2c(c1)OC([C@H]1[C@H]2C=C(CC1)C(=O)OCC)(C)C
• InChI: InChI=1S/C23H32O4/c1-5-7-8-9-15-12-19(24)21-17-14-16(22(25)26-6-2)10-11-18(17)23(3,4)27-20(21)13-15/h12-14,17-18,24H,5-11H2,1-4H3/t17-,18-/m1/s1
• InChIKey: SOCHNPHPKBRBTC-QZTJIDSGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl (6aR,10aR)-1-hydroxy-6,6-dimethyl-3-pentyl-6H,6aH,7H,8H,10aH-benzo[c]isochromene-9-carboxylate
• IUPAC Traditional name: ethyl (6aR,10aR)-1-hydroxy-6,6-dimethyl-3-pentyl-6aH,7H,8H,10aH-benzo[c]isochromene-9-carboxylate
• Synonyms: (6aR,10aR)-6a,7,8,10a-Tetrahydro-1-hydroxy-6,6-dimethyl-3-pentyl-6H-dibenzo[b,d]pyran-9-carboxylic Acid Ethyl Ester; (-)-11-Nor-Δ9-Tetrahydro Cannabinol-9-carboxylic Acid Ethyl Ester

Database IDs

• CAS Number: 1262438-64-1
• PubChem SID: 164231627
• PubChem CID: 71751246

CALCULATED PROPERTIES

• Acid pKa: 9.342289
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 5.871823
• LogD (pH = 7.4): 5.866984
• Log P: 5.871885
• Molar Refractivity: 107.9684 cm^3
• Polarizability: 41.899002 Å^3
• Polar Surface Area: 55.76 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ether

DETAILS

Toronto Research Chemicals - N826260

A protected metabolite of Tetrahydrocannabinol (T293200).

REFERENCES

• Fellermeier, M., et al.: Eur. J. Biochem., 268, 1596 (2001)
• Rohrich, J., et al.: J. Anal. Toxicol., 34, 196 (2010)