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

• ChemBase ID: 68708
• 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-/m1/s1
• InChIKey: JNJCEALGCZSIGB-SECBINFHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-hydroxy-4-phenylbutanoic acid
• IUPAC Traditional name: (2R)-2-hydroxy-4-phenylbutanoic acid
• Synonyms: (R)-2-Hydroxy-4-phenylbutyric acid; (R)-2-Hydroxy-4-phenylbutyric acid; (R)-(-)-2-Hydroxy-4-phenylbutyric acid; (R)-2-羟基-4-苯基丁酸; (R)-(-)-2-羟基-4-苯基丁酸

Database IDs

• CAS Number: 29678-81-7
• MDL Number: MFCD00192219
• Beilstein Number: 3201296
• PubChem SID: 162034438; 24866310
• PubChem CID: 2759328

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

• Melting Point: 114-117 °C; 114-117 °C(lit.); 114-117°C
• Optical Rotation: [α]20/D -9.5±1°, c = 2.8% in ethanol; [α]20/D -9.5°, c = 2.8 in ethanol; -9.5 (c=2.8 in ethanol)

Safety Information

• Storage Warning: IRRITANT
• German water hazard class: 3
• TSCA Listed: false; 否
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥99.0% (sum of enantiomers, HPLC); 95+%; 97%; 99%
• Grade: puriss.
• Linear Formula: C6H5CH2CH2CH(OH)CO2H

DETAILS

Sigma Aldrich - 420085

Packaging
100 mg in glass bottle

Sigma Aldrich - 56112

Other Notes
Chiral building block; the triflate of the corresponding ester is used for preparing ACE inhibitors1,2,3