(3-amino-3-carboxypropyl)dimethylsulfanium chloride

• ChemBase ID: 156003
• Molecular Formular: C6H14ClNO2S
• Molecular Mass: 199.69886
• Monoisotopic Mass: 199.04337737
• SMILES: C[S+](C)CCC(C(=O)O)N.[Cl-]
• Canonical SMILES: NC(C(=O)O)CC[S+](C)C.[Cl-]
• InChI: InChI=1S/C6H13NO2S.ClH/c1-10(2)4-3-5(7)6(8)9;/h5H,3-4,7H2,1-2H3;1H
• InChIKey: MYGVPKMVGSXPCQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3-amino-3-carboxypropyl)dimethylsulfanium chloride
• IUPAC Traditional name: S-methylmethionine chloride
• Synonyms: (3-Amino-3-carboxypropyl)dimethyl sulfonium chloride; MMS; Methyl-methionine sulphonium chloride; Vitamin U; DL-Methionine methylsulfonium chloride

Database IDs

• CAS Number: 3493-12-7
• EC Number: 222-484-4
• MDL Number: MFCD00031700
• Beilstein Number: 4163617
• PubChem SID: 162250141; 24883297
• PubChem CID: 14220

CALCULATED PROPERTIES

• Acid pKa: 2.2369895
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -3.0985818
• LogD (pH = 7.4): -3.4862044
• Log P: -3.3250556
• Molar Refractivity: 41.0974 cm^3
• Polarizability: 17.25681 Å^3
• Polar Surface Area: 63.32 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble100 mg/mL, clear, colorless
• pH: 4.0-5.5

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥99.0% (AT)
• Ignition Residue: ≤0.1%
• Impurities: ≤0.002% heavy metals
• Loss on Drying: ≤1% loss on drying
• Empirical Formula (Hill Notation): C6H14ClNO2S

DETAILS

Sigma Aldrich - 64382

Biochem/physiol Actions
DL-Methionine methylsulfonium (DL-MMSC), a racemic mixture, is used to study its mechanism of protection against gastric ulceration. DL-MMSC may also be used as a methionine analogue.
S-Methionine methylsulfonium (SMMS) chloride is a derivative of methionine metabolism in some plants. SMMS has potent therapeutic effects on gastrointestinal ulceration potentially via its ability to promote dermal fibroblast migration and growth.