(2R)-2-hydroxy-3-phenylpropanoic acid

• ChemBase ID: 69466
• Molecular Formular: C9H10O3
• Molecular Mass: 166.1739
• Monoisotopic Mass: 166.06299418
• SMILES: C(=O)([C@@H](Cc1ccccc1)O)O
• Canonical SMILES: O[C@@H](C(=O)O)Cc1ccccc1
• InChI: InChI=1S/C9H10O3/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5,8,10H,6H2,(H,11,12)/t8-/m1/s1
• InChIKey: VOXXWSYKYCBWHO-MRVPVSSYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-hydroxy-3-phenylpropanoic acid
• IUPAC Traditional name: (R)-phenyllactate
• Synonyms: (R)-2-Hydroxy-3-phenylpropanoic acid; (R)-3-Phenyllactic acid; (R)-2-Hydroxy-3-phenylpropionic acid; D-(+)-3-Phenyllactic acid; (R)-2-Hydroxy-3-phenylpropionic acid; (R)-2-羟基-3-苯丙酸; (R)-3-苯基乳酸; D-(+)-3-苯基乳酸

Database IDs

• CAS Number: 7326-19-4
• EC Number: 230-803-3
• MDL Number: MFCD00078062
• Beilstein Number: 2209793
• PubChem SID: 162035192; 24887376; 24863476
• PubChem CID: 643327

CALCULATED PROPERTIES

• Acid pKa: 4.020981
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -0.30485204
• LogD (pH = 7.4): -1.9624155
• Log P: 1.1844969
• Molar Refractivity: 43.4588 cm^3
• Polarizability: 16.998539 Å^3
• Polar Surface Area: 57.53 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 122-124 °C(lit.); 122-124°C; 123-125 °C
• Optical Rotation: [α]20/D +19°, c = 1 in ethanol; [α]20/D +22.0±1°, c = 1% in H2O; +22 (c=1 in water)

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: ≥97.0% (T); 95+%; 98%
• Grade: purum
• Linear Formula: C6H5CH2CH(OH)CO2H

DETAILS

Sigma Aldrich - 376906

Packaging
5 g in glass bottle
Application
Chiral building block employed in the preparation of statine.1 Starting material in the preparation of the hypoglycemic agent enlitazone and of 15N-labeled phenylalanine.2,3
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 376906.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.