(2S)-2-hydroxy-2-phenylacetic acid

• ChemBase ID: 2028
• Molecular Formular: C8H8O3
• Molecular Mass: 152.14732
• Monoisotopic Mass: 152.04734412
• SMILES: O[C@H](C(=O)O)c1ccccc1
• Canonical SMILES: O[C@@H](c1ccccc1)C(=O)O
• InChI: InChI=1S/C8H8O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,7,9H,(H,10,11)/t7-/m0/s1
• InChIKey: IWYDHOAUDWTVEP-ZETCQYMHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-hydroxy-2-phenylacetic acid
• IUPAC Traditional name: (S)-mandelic acid
• Synonyms: (αS)-α-Hydroxybenzeneacetic Acid; L-Mandelic Acid; (+)-(S)-Mandelic Acid; (+)-L-Mandelic Acid; (+)-Mandelic Acid; (+)-α-Hydroxyphenylacetic Acid; (2S)-2-Hydroxy-2-(phenyl)ethanoic Acid; L-2-Phenylglycolic Acid; (S)-2-hydroxy-2-phenylacetic acid; L-MANDELIC ACID; (S)-Mandelic Acid; (S)-(+)-alpha-Hydroxyphenylacetic acid; (2S)-2-hydroxy-2-phenylacetic acid; (S)-α-Hydroxyphenylacetic acid; (S)-(+)-Mandelic acid; L-(+)-Mandelic acid; (R)-Mandelic Acid; (R)-(-)-alpha-Hydroxyphenylacetic acid; (2R)-(-)-Hydroxy(phenyl)ethanoic acid; D-(-)-Phenylglycolic acid; D-(-)-Mandelic acid 98%; (S)-(+)-Mandelic acid; (S)-α-羟基苯乙酸; (S)-(+)-扁桃酸; L-(+)-扁桃酸

Database IDs

• CAS Number: 17199-29-0; 90-64-2; 611-71-2
• EC Number: 241-240-8
• MDL Number: MFCD00064251; MFCD00004495
• Beilstein Number: 2208678
• PubChem SID: 24896592; 24882634; 46507928; 24882637; 160965483; 46506374
• PubChem CID: 439616

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.7512336
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -0.85347056
• LogD (pH = 7.4): -2.3882656
• Log P: 0.89583564
• Molar Refractivity: 38.7038 cm^3
• Polarizability: 15.161119 Å^3
• Polar Surface Area: 57.53 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.66
• LOG S: -0.96
• Solubility (Water): 1.68e+01 g/l

PROPERTIES

Physical Property

• Solubility: 110 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]; Methanol; Water
• Apperance: Off-White Solid
• Melting Point: 130-133 °C; 131 - 134°C; 131-133°C; 131-134 °C(lit.); 131-135°C; 131-135°C
• Flash Point: >110°C
• Optical Rotation: [α]20/D +153±5°, c = 5% in H2O; [α]20/D +154°, c = 2.8 in H2O; [α]20/D +155±5°, c = 5% in H2O; +155 (c=5 in water)
• Hydrophobicity(logP): 0.502

Safety Information

• Storage Condition: Refrigerator
• Storage Warning: IRRITANT; Irritant/Light Sensitive; Light Sensitive
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 41
• Safety Statements: 26-39
• TSCA Listed: false; 是
• GHS Pictograms: GHS05
• GHS Hazard statements: H318
• GHS Precautionary statements: P280-P305+P351+P338-P310
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98.0% (T); ≥99%; ≥99.0% (T); 95%; 95+%; 97%; 98%; 99+%
• Grade: puriss.; purum; ReagentPlus®
• Optical Purity: ee: 99% (GLC); enantiomeric ratio: ≥98:1 (HPLC); enantiomeric ratio: ≥99:1 (HPLC)
• Linear Formula: C6H5CH(OH)CO2H
• Empirical Formula (Hill Notation): C8H8O3
• Classification: Genuine Natural Compounds

DETAILS

MP Biomedicals - 05208166

MP Biomedicals Rare Chemical collection

DrugBank - DB02280

Drug information: experimental

DrugBank - DB03357

Drug information: experimental

Sigma Aldrich - M2004

Packaging
25, 100 g in poly bottle
Application
A versatile reagent1 used in the resolution of racemates2 and the preparation of amides.3,4,5
Legal Information
ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

Toronto Research Chemicals - M162535

Antiseptic (urinary).

REFERENCES

• Pessela, B., et al.: Enzyme Microb. Technol., 40, 310 (2007)
• Carrasco-Lopez, C., et al.: J. Biol. Chem., 284, 4365 (2007)