(2S)-3-(acetylsulfanyl)-2-methylpropanoic acid

• ChemBase ID: 103000
• Molecular Formular: C6H10O3S
• Molecular Mass: 162.2068
• Monoisotopic Mass: 162.03506518
• SMILES: O=C(SC[C@H](C(=O)O)C)C
• Canonical SMILES: CC(=O)SC[C@H](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)/t4-/m1/s1
• InChIKey: VFVHNRJEYQGRGE-SCSAIBSYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-3-(acetylsulfanyl)-2-methylpropanoic acid
• IUPAC Traditional name: (2S)-3-(acetylsulfanyl)-2-methylpropanoic acid
• Synonyms: D-(-)-S-ACETYL-β-MERCAPTO-ISOBUTYRIC ACID; (S)-β-(Acetylmercapto)isobutyric acid; D-(-)-S-Acetyl-β-mercaptoisobutyric acid; (S)-(-)-3-(Acetylthio)-2-methylpropionic acid; (2S)-3-(Acetylthio)-2-methylpropanoic Acid; (S)-3-(Acetylthio)-2-methylpropanoic acid; (S)-3-Acetylsulfanyl-2-methylpropionic Acid; (S)-3-Acetylthio-2-methylpropionic acid; D-(-)-3-Acetylthio-2-methylpropionic Acid; D-3-Acetylthio-2-methylpropionic Acid; D-β-Acetylthioisobutyric Acid; (S)-(-)-3-Acetylthio-2-methylpropionic Acid; (S)-β-(乙酰巯基)异丁酸; D-(-)-S-乙酰-β-巯基异丁酸; (S)-(-)-3-硫代乙酰-2-甲基丙酸

Database IDs

• CAS Number: 74431-52-0; 76497-39-7
• EC Number: 278-480-8; 277-868-4
• MDL Number: MFCD00038563
• Beilstein Number: 1764649
• PubChem SID: 24870806; 162090784
• PubChem CID: 2724506

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

• Flash Point: >112 °C; >233.6 °F
• Density: 1.178 g/mL at 20 °C(lit.); 1.1827 g/mL at 25 °C
• Refractive Index: n20/D 1.490
• Optical Rotation: [α]20/D -39°, c = 0.1 N in methanol

Safety Information

• Storage Condition: 0°C
• European Hazard Symbols: Corrosive (C)
• UN Number: 3265
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 2
• Risk Statements: 34
• Safety Statements: 26-36/37/39-45
• GHS Pictograms: GHS05
• GHS Signal Word: Danger
• GHS Hazard statements: H314
• GHS Precautionary statements: P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 3265 8/PG 2

Product Information

• Purity: 97%
• Empirical Formula (Hill Notation): C6H10O3S

DETAILS

MP Biomedicals - 02150236

Optically active pharmaceutical intermediate, particularly for antihypertensives

Sigma Aldrich - 472522

Packaging
1 g in glass bottle

Toronto Research Chemicals - A188770

S-Acetylthio-2-methylpropionic acid (S-AMPA) is a key chiral 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)