(2R)-2-hydroxy-4-(2H5)phenylbutanoic acid

• ChemBase ID: 171061
• Molecular Formular: C10H12O3
• Molecular Mass: 180.20048
• Monoisotopic Mass: 180.07864424
• SMILES: c1(CC[C@H](C(=O)O)O)ccccc1
• 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-/m1/s1
• InChIKey: JNJCEALGCZSIGB-SECBINFHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-hydroxy-4-(^2H₅)phenylbutanoic acid
• IUPAC Traditional name: (2R)-2-hydroxy-4-(^2H₅)phenylbutanoic acid
• Synonyms: (αR)-α-Hydroxybenzenebutanoic Acid-d5; (R)-2-Hydroxy-4-phenylbutanoic Acid-d5; (R)-2-Hydroxy-4-phenylbutyric Acid-d5; (R)-α-Hydroxybenzenebutanoate-d5; L-4-Phenyl-α-hydroxybutyric Acid-d5; D-(-)-Benzyllactic Acid-d5; (R)-2-Hydroxy-4-phenylbutyric Acid-d5

Database IDs

• CAS Number: 1286987-57-2
• PubChem SID: 164226971
• PubChem CID: 71749243

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: 18.855007 Å^3
• Polar Surface Area: 57.53 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane

DETAILS

Toronto Research Chemicals - H949093

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

REFERENCES

• Schmidt, E., et al.: J. Biotechnol., 31, 233 (1993)
• Palomo, J., et al.: Biomacromol., 4, 1 (1993)
• Verissimo, E., et al.: Bioorg. Med. Chem. Lett., 18, 4210 (1993)