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

• ChemBase ID: 68527
• Molecular Formular: C10H12O3
• Molecular Mass: 180.20048
• Monoisotopic Mass: 180.07864424
• SMILES: C(=O)([C@H](CCc1ccccc1)O)O
• Canonical SMILES: O[C@H](C(=O)O)CCc1ccccc1
• InChI: InChI=1S/C10H12O3/c11-9(10(12)13)7-6-8-4-2-1-3-5-8/h1-5,9,11H,6-7H2,(H,12,13)/t9-/m0/s1
• InChIKey: JNJCEALGCZSIGB-VIFPVBQESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-hydroxy-4-phenylbutanoic acid
• IUPAC Traditional name: (2S)-2-hydroxy-4-phenylbutanoic acid
• Synonyms: (S)-2-Hydroxy-4-phenylbutyric acid; (αS)-α-Hydroxybenzenebutanoic Acid; (S)-2-Hydroxy-4-phenylbutanoic Acid; (S)-2-Hydroxy-4-phenylbutyric Acid; (S)-α-Hydroxybenzenebutanoate; L-4-Phenyl-α-hydroxybutyric Acid

Database IDs

• CAS Number: 115016-95-0
• MDL Number: MFCD06656492
• PubChem SID: 162034258
• PubChem CID: 11159656

CALCULATED PROPERTIES

• Acid pKa: 4.1208735
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 0.23522814
• LogD (pH = 7.4): -1.4566362
• Log P: 1.6290655
• Molar Refractivity: 48.0598 cm^3
• Polarizability: 18.833664 Å^3
• Polar Surface Area: 57.53 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethanol; Methanol
• Apperance: White Solid
• Melting Point: 110-112°C

Safety Information

• Storage Condition: -20°C Freezer
• Storage Warning: IRRITANT
• TSCA Listed: false

Product Information

• Purity: 95+%

DETAILS

Toronto Research Chemicals - H949090

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

REFERENCES

• Chang, A., et al.: Diabetes, 32, 830 (1983)
• Goldstein, B. et al.: Cell Biochem., 48, 33 (1983)
• Sredy, J., et al.: Metabolism, 44, 1074 (1983)