3-(acetylsulfanyl)-2-methylpropanoic acid

• ChemBase ID: 80613
• Molecular Formular: C6H10O3S
• Molecular Mass: 162.2068
• Monoisotopic Mass: 162.03506518
• SMILES: S(CC(C(=O)O)C)C(=O)C
• Canonical SMILES: CC(=O)SCC(C(=O)O)C
• InChI: InChI=1S/C6H10O3S/c1-4(6(8)9)3-10-5(2)7/h4H,3H2,1-2H3,(H,8,9)
• InChIKey: VFVHNRJEYQGRGE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(acetylsulfanyl)-2-methylpropanoic acid
• IUPAC Traditional name: 3-(acetylsulfanyl)-2-methylpropanoic acid
• Synonyms: beta-Acetylmercaptoisobutyric acid; 3-(Acetylthio)-2-methylpropanoic acid; 3-(Acetylthio)-2-methylpropanoic Acid; 3-Mercapto-2-methylpropionic Acid Acetate (RS)-3-Acetylthio-2-methylpropionic Acid; (±)-3-Acetylthio-2-methylpropionic Acid; 2-(Acetylthiomethyl)propanoic Acid; 3-Acetylsulfanyl-2-methylpropionic Acid; 3-Mercapto-2-methylpropionic Acid Acetate; 3-Acetylthio-2-methylpropionic Acid

Database IDs

• CAS Number: 33325-40-5
• MDL Number: MFCD00066543
• PubChem SID: 162067733
• PubChem CID: 118073

CALCULATED PROPERTIES

• Acid pKa: 4.1436687
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -0.54075325
• LogD (pH = 7.4): -2.2396
• Log P: 0.8313822
• Molar Refractivity: 39.1162 cm^3
• Polarizability: 15.540257 Å^3
• Polar Surface Area: 54.37 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: White to Off-White Solid
• Melting Point: 40-41°C; 55-57°C

Safety Information

• Storage Condition: -20°C Freezer
• Storage Warning: Irritant

DETAILS

Toronto Research Chemicals - A188775

3-Acetylthio-2-methylpropionic acid is a key intermediate for Captopril (C175750) and other hypertension drugs.

REFERENCES

• Cushman, D., et al.: Biochem., 16, 5484 (1977)
• Ondetti, M., et al.: J. Med. Chem., 24, 355 (1977)
• Tseng, T., et al.: Cancer Lett., 62, 233 (1977)