ethyl (2R)-2-hydroxy-4-phenylbutanoate

• ChemBase ID: 143229
• Molecular Formular: C12H16O3
• Molecular Mass: 208.25364
• Monoisotopic Mass: 208.10994437
• SMILES: CCOC(=O)[C@@H](CCc1ccccc1)O
• Canonical SMILES: CCOC(=O)[C@@H](CCc1ccccc1)O
• InChI: InChI=1S/C12H16O3/c1-2-15-12(14)11(13)9-8-10-6-4-3-5-7-10/h3-7,11,13H,2,8-9H2,1H3/t11-/m1/s1
• InChIKey: ZJYKSSGYDPNKQS-LLVKDONJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl (2R)-2-hydroxy-4-phenylbutanoate
• IUPAC Traditional name: ethyl (2R)-2-hydroxy-4-phenylbutanoate
• Synonyms: (αR)-α-Hydroxybenzenebutanoic Acid Ethyl Ester; (R)-Ethyl 2-Hydroxy-4-phenylbutanoate; Ethyl (R)-α-Hydroxybenzenebutanoate; Ethyl 2(R)-hydroxy-4-phenylbutyrate; (R)-2-Hydroxy-4-phenylbutyric Acid Ethyl Ester; Ethyl (R)-(-)-2-hydroxy-4-phenylbutyrate; (R)-Ethyl 2-hydroxy-4-phenylbutanoate; (R)-(-)-2-羟基-4-苯基丁酸乙酯

Database IDs

• CAS Number: 90315-82-5
• MDL Number: MFCD00077794
• Beilstein Number: 3590943
• PubChem SID: 24879916; 162237450; 24869747
• PubChem CID: 2733848

CALCULATED PROPERTIES

• Acid pKa: 12.695693
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 2.1317675
• LogD (pH = 7.4): 2.1317654
• Log P: 2.1317675
• Molar Refractivity: 57.5775 cm^3
• Polarizability: 22.760132 Å^3
• Polar Surface Area: 46.53 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: Colorless Oil
• Boiling Point: 212 °C(lit.)
• Flash Point: 150 °C; 302 °F
• Density: 1.075 g/mL at 20 °C(lit.)
• Refractive Index: n20/D 1.504(lit.); n20/D 1.505
• Optical Rotation: [α]20/D -21±1°, c = 1% in chloroform; [α]21/D -10°, neat

Safety Information

• Storage Condition: Refrigerator
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves; Eyeshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US)
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97.5% (GC); ≥99.0% (sum of enantiomers, GC); 98%
• Grade: produced by BASF; puriss.
• Optical Purity: enantiomeric excess: ≥97.5%; enantiomeric ratio: ≥99:1 (HPLC)
• Linear Formula: C6H5CH2CH2CH(OH)CO2C2H5

DETAILS

Sigma Aldrich - 727210

Packaging
5, 25 g in glass bottle
Legal Information
ChiPros is a registered trademark of BASF SE

Sigma Aldrich - 460826

Packaging
5 g in glass bottle

Sigma Aldrich - 56114

Other Notes
Synthesis of ACE inhibitors by reaction of the corresponding triflate or other sulfonates with amines to give derivatives of (S)-homophenylalanine1,2,3

Toronto Research Chemicals - H949096

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)