4-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)butanoic acid

• ChemBase ID: 104273
• Molecular Formular: C8H9NO4
• Molecular Mass: 183.16136
• Monoisotopic Mass: 183.05315777
• SMILES: OC(=O)CCCN1C(=O)C=CC1=O
• Canonical SMILES: OC(=O)CCCN1C(=O)C=CC1=O
• InChI: InChI=1S/C8H9NO4/c10-6-3-4-7(11)9(6)5-1-2-8(12)13/h3-4H,1-2,5H2,(H,12,13)
• InChIKey: NCPQROHLJFARLL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)butanoic acid
• IUPAC Traditional name: N-maleoyl-4-aminobutyric acid
• Synonyms: 4-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)butanoic acid; 2,5-Dihydro-2,5-dioxo-1H-pyrrole-1-butanoic Acid; 4-Maleimidobutyric Acid; γ-Maleimidobutyric acid; 4-Maleimidobutanoic acid; N-(3-Carboxypropyl)maleimide; N-Maleoyl-4-aminobutyric acid; 4-Maleimidobutyric acid; N-Maleoyl-GABA; γ-MALEIMIDOBUTYRIC ACID

Database IDs

• CAS Number: 57078-98-5
• MDL Number: MFCD00043139
• Beilstein Number: 1455876
• PubChem SID: 162091725; 24882439
• PubChem CID: 3404904

CALCULATED PROPERTIES

• Acid pKa: 4.0619745
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -1.8586489
• LogD (pH = 7.4): -3.531021
• Log P: -0.4085696
• Molar Refractivity: 43.7871 cm^3
• Polarizability: 16.444082 Å^3
• Polar Surface Area: 74.68 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate
• Apperance: White Solid
• Melting Point: 87-89°C; 95-98 °C

Safety Information

• Storage Condition: 0°C, Desiccate; Refrigerator
• 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: ≥98% (titration); ≥98.0% (T)
• Empirical Formula (Hill Notation): C8H9NO4

DETAILS

MP Biomedicals - 02155307

(N-Maleoyl-GABA) Modification reagent for thiol groups in proteins

Sigma Aldrich - M8779

Application
Modification reagent for thiol groups in proteins

Sigma Aldrich - 63174

Application
Modification reagent for thiol groups in proteins
Other Notes
SH-label for the modification of peptides and proteins1; Used for the preparation of a new bleomycin analog for enzyme immunoassay (EIA)2; probe for membrane SH-groups3,4

Toronto Research Chemicals - M135960

A short crosslinking reagent.

REFERENCES

• Rich, D.H., et al., J. Med. Chem., 18: 1004, (1975).