(1R,2R,3S,5R)-2,6,6-trimethylbicyclo[3.1.1]heptane-2,3-diol

• ChemBase ID: 176732
• Molecular Formular: C10H18O2
• Molecular Mass: 170.24872
• Monoisotopic Mass: 170.13067982
• SMILES: C1([C@@H]2C[C@@H]([C@@]([C@H]1C2)(O)C)O)(C)C
• Canonical SMILES: O[C@H]1C[C@@H]2C[C@H]([C@@]1(C)O)C2(C)C
• InChI: InChI=1S/C10H18O2/c1-9(2)6-4-7(9)10(3,12)8(11)5-6/h6-8,11-12H,4-5H2,1-3H3/t6-,7-,8+,10-/m1/s1
• InChIKey: MOILFCKRQFQVFS-BDNRQGISSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2R,3S,5R)-2,6,6-trimethylbicyclo[3.1.1]heptane-2,3-diol
• IUPAC Traditional name: (1R,2R,3S,5R)-2,6,6-trimethylbicyclo[3.1.1]heptane-2,3-diol
• Synonyms: (1R,2R,3S,5R)-2,6,6-Trimethylbicyclo[3.1.1]heptane-2,3-diol; (-)-2-Hydroxyisopinocampheol; (1R,2R,3S,5R)-2,3-Pinanediol; (-)-(1R:2R:3S:5R)-cis-α-Pineneglycol; cis-α-Pinene Glycol; [1R-(1α,2α,3α,5α)]-2,6,6-Trimethylbicyclo[3.1.1]heptane-2,3-diol; (-)-2,3-Pinanediol; (-)-cis-Pinane-cis-2,3-diol; (1R,2R,3S,5R)-(-)-2,3-Pinanediol; (1R,2R,3S,5R)-(-)-2,3-Pinanediol

Database IDs

• CAS Number: 22422-34-0
• PubChem SID: 164232642
• PubChem CID: 6553875

CALCULATED PROPERTIES

• Acid pKa: 13.601064
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 0.8171301
• LogD (pH = 7.4): 0.81712985
• Log P: 0.8171301
• Molar Refractivity: 46.9159 cm^3
• Polarizability: 18.930742 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol; Toluene
• Apperance: Off-White Solid
• Melting Point: 55-57°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - P458400

(1R,2R,3S,5R)-(-)-2,3-Pinanediol is a bicyclic monoterpene diols that has been shown to induce differentiation of S91 melanoma and PC12 pheochromocytoma cells and thus provide possible therapeutic and sunless tanning use. (1R,2R,3S,5R)-(-)-2,3-Pinanediol

REFERENCES

• Farooq, A. et al.: Zeitsch. Naturforsch. C J. Biosci., 57, 686 (2002)
• Brown, D.A. et al.: Pigment Cell Res., 12, 36 (2002)