(1R,2R,5R)-2-hydroxy-2,6,6-trimethylbicyclo[3.1.1]heptan-3-one

• ChemBase ID: 171127
• Molecular Formular: C10H16O2
• Molecular Mass: 168.23284
• Monoisotopic Mass: 168.11502975
• SMILES: C1([C@@H]2CC(=O)[C@@]([C@H]1C2)(O)C)(C)C
• Canonical SMILES: O=C1C[C@@H]2C[C@H]([C@@]1(C)O)C2(C)C
• InChI: InChI=1S/C10H16O2/c1-9(2)6-4-7(9)10(3,12)8(11)5-6/h6-7,12H,4-5H2,1-3H3/t6-,7-,10-/m1/s1
• InChIKey: VZRRCQOUNSHSGB-BRDIYROLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2R,5R)-2-hydroxy-2,6,6-trimethylbicyclo[3.1.1]heptan-3-one
• IUPAC Traditional name: (1R,2R,5R)-2-hydroxy-2,6,6-trimethylbicyclo[3.1.1]heptan-3-one
• Synonyms: (1R,2R,5R)-2-Hydroxy-2,6,6-trimethylbicyclo[3.1.1]heptan-3-one; [1R-(1α,2α.,5α)]- (+)-2-Hydroxy-3-pinanone; (+)-2-Hydroxypinocamphone; (+)-2α-Hydroxy-10β-pinan-3-one; (+)-2α-Hydroxy-3-pinanone; (+)-(1R,2R,5R)-2-Hydroxy-3-pinanone

Database IDs

• CAS Number: 24047-72-1
• PubChem SID: 164227037
• PubChem CID: 6553882

CALCULATED PROPERTIES

• Acid pKa: 13.036358
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 1.3806578
• LogD (pH = 7.4): 1.3806568
• Log P: 1.3806578
• Molar Refractivity: 46.0936 cm^3
• Polarizability: 18.386003 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Ethyl Acetate; Methanol
• Apperance: White Low Melting Solid
• Melting Point: <30°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - H952000

An essential oil from Hyssopus officinalis L. and Cymbopogon jwarancusa (Jones) Schult. It is used in cosmetics.

REFERENCES

• Papini, A., et al.: J. Med. Chem., 44, 3504 (2001)
• Plietker, B., et al.: Org. Biomol. Chem., 2, 1116 (2001)