3-(acetylsulfanyl)-2-benzylpropanoic acid

• ChemBase ID: 78149
• Molecular Formular: C12H14O3S
• Molecular Mass: 238.30276
• Monoisotopic Mass: 238.06636531
• SMILES: OC(=O)C(Cc1ccccc1)CSC(=O)C
• Canonical SMILES: OC(=O)C(Cc1ccccc1)CSC(=O)C
• InChI: InChI=1S/C12H14O3S/c1-9(13)16-8-11(12(14)15)7-10-5-3-2-4-6-10/h2-6,11H,7-8H2,1H3,(H,14,15)
• InChIKey: BCAAXVOKLXDSPD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(acetylsulfanyl)-2-benzylpropanoic acid
• IUPAC Traditional name: 3-(acetylsulfanyl)-2-benzylpropanoic acid
• Synonyms: 3-(Acetylsulphanyl)-2-benzylpropanoic acid; 2-[(Acetylthio)methyl]-3-phenylpropanoic acid 96%; α-[(Acetylthio)methyl]benzenepropanoic Acid; 2-(Acetylthiomethyl)-3-phenylpropionic Acid; 2-[(Acetylsulfanyl)methyl]-3-phenylpropionic Acid; 3-(Acetylthio)-2-benzylpropionic Acid

Database IDs

• CAS Number: 91702-98-6
• MDL Number: MFCD00236751
• PubChem SID: 162042964
• PubChem CID: 9991796

CALCULATED PROPERTIES

• Acid pKa: 4.3114796
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.1959482
• LogD (pH = 7.4): -0.5448512
• Log P: 2.4097548
• Molar Refractivity: 63.8122 cm^3
• Polarizability: 25.069221 Å^3
• Polar Surface Area: 54.37 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Methanol
• Apperance: Brownish Liquid

Safety Information

• Storage Warning: Irritant

DETAILS

Toronto Research Chemicals - A188690

Racecadotril intermediate. A β-thiopropionyl-amino acid derivative used as β-lactamase inhibitor.

REFERENCES

• Sanger, F., et al.: Biochem. J., 39, 507 (1945)
• Dawson, P., et al.: Science, 266, 776 (1945)