(2S)-2-hydroxy-4-oxo-4-phenylbutanoic acid

• ChemBase ID: 171022
• Molecular Formular: C10H10O4
• Molecular Mass: 194.184
• Monoisotopic Mass: 194.0579088
• SMILES: c1cccc(c1)C(=O)C[C@H](O)C(=O)O
• Canonical SMILES: O[C@H](C(=O)O)CC(=O)c1ccccc1
• InChI: InChI=1S/C10H10O4/c11-8(6-9(12)10(13)14)7-4-2-1-3-5-7/h1-5,9,12H,6H2,(H,13,14)/t9-/m0/s1
• InChIKey: COFAOIWBTJSSPD-VIFPVBQESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-hydroxy-4-oxo-4-phenylbutanoic acid
• IUPAC Traditional name: (2S)-2-hydroxy-4-oxo-4-phenylbutanoic acid
• Synonyms: (αS)-α-Hydroxy-γ-oxo-benzenebutanoic Acid; 2-(S)-Hydroxy-4-oxo-4-phenylbutyric Acid

Database IDs

• CAS Number: 146912-63-2
• PubChem SID: 164226932
• PubChem CID: 9942381

CALCULATED PROPERTIES

• Acid pKa: 3.5034244
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -1.3477845
• LogD (pH = 7.4): -2.7337623
• Log P: 0.64059764
• Molar Refractivity: 48.6923 cm^3
• Polarizability: 18.931038 Å^3
• Polar Surface Area: 74.6 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Methanol
• Apperance: White Solid
• Melting Point: 136-139°C

DETAILS

Toronto Research Chemicals - H948875

Used in the preparation of benzothiophenes, benzofurans, and indoles useful in the treatment of insulin resistance and hyperglycemia.

REFERENCES

• Liese, A., et al.: Enzyme Microbiol. Technol., 30, 673 (2002)