2,5-dioxopyrrolidin-1-yl 4-[4-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)phenyl]butanoate

• ChemBase ID: 132552
• Molecular Formular: C18H16N2O6
• Molecular Mass: 356.32944
• Monoisotopic Mass: 356.10083624
• SMILES: c1cc(ccc1CCCC(=O)ON1C(=O)CCC1=O)N1C(=O)C=CC1=O
• Canonical SMILES: O=C(ON1C(=O)CCC1=O)CCCc1ccc(cc1)N1C(=O)C=CC1=O
• InChI: InChI=1S/C18H16N2O6/c21-14-8-9-15(22)19(14)13-6-4-12(5-7-13)2-1-3-18(25)26-20-16(23)10-11-17(20)24/h4-9H,1-3,10-11H2
• InChIKey: PMJWDPGOWBRILU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,5-dioxopyrrolidin-1-yl 4-[4-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)phenyl]butanoate
• IUPAC Traditional name: 2,5-dioxopyrrolidin-1-yl 4-[4-(2,5-dioxopyrrol-1-yl)phenyl]butanoate
• Synonyms: 4-(4-Maleimidophenyl)butyric acid N-succinimidyl ester; 4-(4-Maleimidophenyl)butyric acid NHS ester; N-Succinimidyl 4-(4-maleimidophenyl)butyrate; SMPB; 4-(4-Maleimidophenyl)butyric acid N-hydroxysuccinimide ester; 1-[4-[4-[(2,5-Dioxo-1-pyrrolidinyl)oxy]-4-oxobutyl]phenyl]-1H-pyrrole-2,5-dione 4-(p-Maleimidophenyl)butyric acid N-hydroxysuccinimide Ester; NSC 344484; N-Succinimidyl 4-(p-Maleimidophenyl)butyrate

Database IDs

• CAS Number: 79886-55-8
• MDL Number: MFCD00054961
• PubChem SID: 162226829
• PubChem CID: 100681

CALCULATED PROPERTIES

• Acid pKa: 17.709122
• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 1.1422018
• LogD (pH = 7.4): 1.1422026
• Log P: 1.1422026
• Molar Refractivity: 89.0891 cm^3
• Polarizability: 34.160084 Å^3
• Polar Surface Area: 101.06 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; DMSO
• Apperance: White Solid
• Melting Point: 123-126°C

Safety Information

• Storage Condition: Refrigerator, Under Inert Atmosphere
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥95% (HPLC)
• Empirical Formula (Hill Notation): C18H16N2O6

DETAILS

Sigma Aldrich - M6286

Application
Heterobifunctional cross-linking reagent.

Sigma Aldrich - 63182

Other Notes
Directional coupling of synthetic peptides to poly-L-lysine and ELISA application1

Toronto Research Chemicals - S690460

A sulfhydryl and amino reactive heterobifunctional protein crosslinking reagent. Spacer Arm: 11.6 Angstroms

REFERENCES

• Martin, F.J., et al.: J. Biol. Chem., 257, 286 (1982)
• Teale, J.M., et al.: J. Mol. Cell Immunol., 2, 283 (1986)