(1R)-1-hydroxy-1-phenylpropan-2-one

• ChemBase ID: 128923
• Molecular Formular: C9H10O2
• Molecular Mass: 150.1745
• Monoisotopic Mass: 150.06807956
• SMILES: CC(=O)[C@@H](c1ccccc1)O
• Canonical SMILES: O[C@H](c1ccccc1)C(=O)C
• InChI: InChI=1S/C9H10O2/c1-7(10)9(11)8-5-3-2-4-6-8/h2-6,9,11H,1H3/t9-/m0/s1
• InChIKey: ZBFFNPODXBJBPW-VIFPVBQESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R)-1-hydroxy-1-phenylpropan-2-one
• IUPAC Traditional name: phenylacetylcarbinol
• Synonyms: (1S)-1-Hydroxy-1-phenyl-2-propanone; (+)-Phenylacetyl Carbinol; (S)-1-Hydroxy-1-phenylpropanone; (S)-Phenylacetyl Carbinol; L-Phenylacetyl Carbinol (~80% ee); L-PAC; (R)-PAC; Phenylacetylcarbinol

Database IDs

• CAS Number: 53439-91-1
• PubChem SID: 162223225
• PubChem CID: 92733; 9920426
• Wikipedia Title: Phenylacetylcarbinol

CALCULATED PROPERTIES

• Acid pKa: 12.697953
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 1.2254611
• LogD (pH = 7.4): 1.225459
• Log P: 1.2254611
• Molar Refractivity: 42.2549 cm^3
• Polarizability: 16.535585 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Powder
• Melting Point: 172°C
• Boiling Point: 253°C
• Density: 1.119 g/cm^3

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - P306300

L-Phenylacetylcarbinol ( (L-PAC) obtained by biotransformation of benzaldehyde; it is a key intermediate for L-Ephedrine.

REFERENCES

• Ellaiah, P., et al.: Ind. Drugs, 24, 192 (1987)
• Nikolova, P., et al.: Biotechnol. Bioeng., 38, 493 (1987)
• Shin, H., et al.: Biotechnol. Bioeng., 49, 52 (1987)