2-(methanesulfonylsulfanyl)acetic acid

• ChemBase ID: 163705
• Molecular Formular: C3H6O4S2
• Molecular Mass: 170.20734
• Monoisotopic Mass: 169.97075067
• SMILES: CS(=O)(=O)SCC(=O)O
• Canonical SMILES: OC(=O)CSS(=O)(=O)C
• InChI: InChI=1S/C3H6O4S2/c1-9(6,7)8-2-3(4)5/h2H2,1H3,(H,4,5)
• InChIKey: ASUZQXBECRATCB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(methanesulfonylsulfanyl)acetic acid
• IUPAC Traditional name: (methanesulfonylsulfanyl)acetic acid
• Synonyms: [(Methylsulfonyl)thio]acetic Acid; Thio-methanesulfonic Acid; Mercapto-acetic Acid methanesulfonate; MTSCM; Carboxymethyl Methanethiosulfonate

Database IDs

• CAS Number: 13700-15-7
• PubChem SID: 162257840
• PubChem CID: 4215938

CALCULATED PROPERTIES

• Acid pKa: 2.9391067
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -3.178874
• LogD (pH = 7.4): -4.142523
• Log P: -0.66113394
• Molar Refractivity: 33.5417 cm^3
• Polarizability: 14.304689 Å^3
• Polar Surface Area: 71.44 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Methanol
• Apperance: White Solid
• Melting Point: 172-174°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - C180500

Reacts specifically and rapidly with thiols to form mixed disulfides. Used to probe the structures of the ACh receptor channel of the GABA receptor channel and of lactose permease.

REFERENCES

• Xu, M. & Akabus, M.H.: J. Biol. Chem., 268, 21505 (1993)
• Duhten, R.L., et al.: Biochemistry, 32, 3139 (1993)
• Yang, N. et al.: Neuron, 16, 113 (1993)
• Kuner, T. et al.: Neuron, 17, 343 (1996)