(2S)-2-(acetyloxy)-2-phenylacetic acid

• ChemBase ID: 148655
• Molecular Formular: C10H10O4
• Molecular Mass: 194.184
• Monoisotopic Mass: 194.0579088
• SMILES: CC(=O)O[C@@H](c1ccccc1)C(=O)O
• Canonical SMILES: OC(=O)[C@H](c1ccccc1)OC(=O)C
• InChI: InChI=1S/C10H10O4/c1-7(11)14-9(10(12)13)8-5-3-2-4-6-8/h2-6,9H,1H3,(H,12,13)/t9-/m0/s1
• InChIKey: OBCUSTCTKLTMBX-VIFPVBQESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-(acetyloxy)-2-phenylacetic acid
• IUPAC Traditional name: (S)-(acetyloxy)(phenyl)acetic acid
• Synonyms: (S)-(+)-α-Acetoxyphenylacetic acid; (S)-(+)-O-Acetylmandelic acid; (S)-(+)-α-Acetoxyphenylacetic acid; (+)-O-Acetyl-L-mandelic acid; (αS)-α-(Acetyloxy)benzeneacetic Acid; L-Mandelic Acid Acetate; (2S)-2-Acetyloxy-2-phenylacetic Acid; (S)-(+)-O-Acetyl-L-mandelic Acid; (S)-2-Acetoxy-2-phenylacetic Acid; (S)-O-Acetylmandelic Acid; L-(+)-O-Acetylmandelic Acid; L-O-Acetylmandelic Acid; S-Acetylmandelic Acid; (S)-O-Acetylmandelic Acid; (S)-(+)-α-乙酰氧基苯乙酸; (S)-(+)-O-乙酰基扁桃酸; (+)-O-乙酰基-L-扁桃酸; (S)-(+)-α-乙酰氧基苯乙酸

Database IDs

• CAS Number: 7322-88-5
• MDL Number: MFCD00064215
• Beilstein Number: 2694109
• PubChem SID: 24855255; 162242830
• PubChem CID: 6923379

CALCULATED PROPERTIES

• Acid pKa: 3.6172729
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -0.5417314
• LogD (pH = 7.4): -1.9999727
• Log P: 1.336961
• Molar Refractivity: 47.8553 cm^3
• Polarizability: 19.013554 Å^3
• Polar Surface Area: 63.6 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Chloroform
• Apperance: White Solid
• Melting Point: 100-102°C; 97-99 °C(lit.); 98-101 °C
• Optical Rotation: [α]20/D +155±3°, c = 2% in acetone; [α]28/D +153°, c = 2 in acetone

Safety Information

• Storage Condition: Refrigerator
• German water hazard class: 3
• Safety Statements: 22-24/25
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98.0% (T); 99%
• Grade: purum
• Optical Purity: ee: 98% (GLC)
• Linear Formula: CH3CO2CH(C6H5)CO2H
• Empirical Formula (Hill Notation): C10H10O4

DETAILS

Sigma Aldrich - 253022

Packaging
5 g in glass bottle
Application
The (R)- and (S)-isomers are chiral derivatizing agents for NMR determination of enantiomeric purity of α-deuterated carboxylic acids, alcohols, and amines.1

Toronto Research Chemicals - A185960

Protected Mandelic Acid, an antibacterial used particularly in the treatment of urinary tract infections.

REFERENCES

• Noguchi, T., et al.: Chem. Pharm. Bull., 55, 393 (2007)
• Ju, X., et al.: App. Microbiol. Biotechnol., 86, 83 (2007)