(1R,4R)-4-(2-hydroxypropan-2-yl)-1-methylcyclohex-2-en-1-ol

• ChemBase ID: 172650
• Molecular Formular: C10H18O2
• Molecular Mass: 170.24872
• Monoisotopic Mass: 170.13067982
• SMILES: C1=C[C@@](CC[C@H]1C(O)(C)C)(O)C
• Canonical SMILES: C[C@@]1(O)CC[C@H](C=C1)C(O)(C)C
• InChI: InChI=1S/C10H18O2/c1-9(2,11)8-4-6-10(3,12)7-5-8/h4,6,8,11-12H,5,7H2,1-3H3/t8-,10-/m0/s1
• InChIKey: XWFVRMWMBYDDFY-WPRPVWTQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,4R)-4-(2-hydroxypropan-2-yl)-1-methylcyclohex-2-en-1-ol
• IUPAC Traditional name: (1R,4R)-4-(2-hydroxypropan-2-yl)-1-methylcyclohex-2-en-1-ol
• Synonyms: (R,R)-(+)-p-Menth-2-ene-1,8-diol; (+)-p-Menth-2-ene-1,8-diol; (1R,4R)-4-Hydroxy-α,α,4-trimethyl-2-cyclohexene-1-methanol; (1R,4R)-2-Menthene-1,8-diol

Database IDs

• CAS Number: 20053-40-1
• PubChem SID: 164228560
• PubChem CID: 6431170

CALCULATED PROPERTIES

• Acid pKa: 18.171066
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 0.9807016
• LogD (pH = 7.4): 0.98070186
• Log P: 0.98070186
• Molar Refractivity: 50.3336 cm^3
• Polarizability: 19.414877 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate; Methanol
• Apperance: White Solid
• Melting Point: 102-105°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - M218870

Intermediate in the preparation of Δ9-Tetrahydro Cannabinol.

REFERENCES

• Singer, M., et al.: Eur. J. Med. Chem., 32, 165 (1997)
• Krishnamurthy, M., et al.: Bioorg. Med. Chem. Lett., 13, 3487 (1997)