N-(2-{[2-(prop-2-enamido)ethyl]disulfanyl}ethyl)prop-2-enamide

• ChemBase ID: 105512
• Molecular Formular: C10H16N2O2S2
• Molecular Mass: 260.37624
• Monoisotopic Mass: 260.06531976
• SMILES: C=CC(=O)NCCSSCCNC(=O)C=C
• Canonical SMILES: C=CC(=O)NCCSSCCNC(=O)C=C
• InChI: InChI=1S/C10H16N2O2S2/c1-3-9(13)11-5-7-15-16-8-6-12-10(14)4-2/h3-4H,1-2,5-8H2,(H,11,13)(H,12,14)
• InChIKey: DJVKJGIZQFBFGS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-(2-{[2-(prop-2-enamido)ethyl]disulfanyl}ethyl)prop-2-enamide
• IUPAC Traditional name: N-(2-{[2-(prop-2-enamido)ethyl]disulfanyl}ethyl)prop-2-enamide
• Synonyms: 2,2′-(Bisacrylamino)diethyl disulfide; BAC; Bis(2-acrylamidoethyl) disulfide; N,N′-Bis(acryloyl)cystamine; N,N'-Bis(acryloyl)cystamine; N,N'-bis-Acrylylcystamine; N,N'-bis(Acryloyl)cystamine; bis-Acrylylcystamine: BAC; N,N'-CYSTAMINE-bis-ACRYLAMIDE; N,N'-双(丙稀酰)胱胺

Database IDs

• CAS Number: 60984-57-8
• EC Number: 262-546-8
• MDL Number: MFCD00036225
• PubChem SID: 24890926; 162092355
• PubChem CID: 100602

CALCULATED PROPERTIES

• Acid pKa: 15.30914
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 0.39751455
• LogD (pH = 7.4): 0.39751583
• Log P: 0.39751586
• Molar Refractivity: 71.395 cm^3
• Polarizability: 27.262354 Å^3
• Polar Surface Area: 58.2 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Powder, Packaged under argon
• Melting Point: 121-125 °C; 123-124°C

Safety Information

• Storage Condition: 0°C, Desiccate
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: ≥97.0% (HPLC); 98%
• Suitability: in accordance for electrophoresis test; suitable for electrophoresis
• Cation Traces: Ca: ≤1000 mg/kg; Cd: ≤5 mg/kg; Co: ≤5 mg/kg; Cr: ≤5 mg/kg; Cu: ≤5 mg/kg; Fe: ≤5 mg/kg; K: ≤50 mg/kg; Mg: ≤50 mg/kg; Mn: ≤5 mg/kg; Na: ≤2000 mg/kg; Ni: ≤5 mg/kg; Pb: ≤5 mg/kg; Zn: ≤5 mg/kg
• Product Line: BioReagent; BioXtra
• Empirical Formula (Hill Notation): C10H16N2O2S2

DETAILS

MP Biomedicals - 02190555

Disulfide containing cross-linker. After electrophoresis, BAC cross-linked gel may be dissolved by addition of a reducing agent such as dithiothreitol or 2-mercaptoethanol. Excellent cross-linker for recovery of material from the gel under physiological conditions.

Sigma Aldrich - A4929

Application
BAC is used as a reversible cross-linker for polyacrylamide gels, to simplify isolation of macromolecules separated on the gels. The disulfide linkage can be broken with a suitable reducing agent. A 1-g slice of a 4% (12:1) gel will dissolve in 5 mL of 100 mM DTT in TBE (pH 8.3) in less than 30 min.
BAC is used as a reversible cross-linker for polyacrylamide gels. The disulfide linkage can be broken with a suitable reducing agent. A 12:1 ratio of acrylamide:BAC is recommended for DNA purification. A one gram slice of a 4% gel will dissolve in 5 mL of 100 mM DTT, TBE solution (pH 8.3) in less than 30 min. The pH of 8.3 is optimum for rapid dissolution of the gel.

Sigma Aldrich - 14460

Application
BAC is used as a reversible cross-linker for polyacrylamide gels, to simplify isolation of macromolecules separated on the gels. The disulfide linkage can be broken with a suitable reducing agent. A 1-g slice of a 4% (12:1) gel will dissolve in 5 mL of 100 mM DTT in TBE (pH 8.3) in less than 30 min.
BAC is used as a reversible cross-linker for polyacrylamide gels. The disulfide linkage can be broken with a suitable reducing agent. A 12:1 ratio of acrylamide:BAC is recommended for DNA purification. A one gram slice of a 4% gel will dissolve in 5 mL of 100 mM DTT, TBE solution (pH 8.3) in less than 30 min. The pH of 8.3 is optimum for rapid dissolution of the gel.

REFERENCES

• Anal. Biochem. , 76 : 37-44 (1976).