3-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)propanoic acid

• ChemBase ID: 66729
• Molecular Formular: C7H7NO4
• Molecular Mass: 169.13478
• Monoisotopic Mass: 169.03750771
• SMILES: C(=O)(CCN1C(=O)C=CC1=O)O
• Canonical SMILES: OC(=O)CCN1C(=O)C=CC1=O
• InChI: InChI=1S/C7H7NO4/c9-5-1-2-6(10)8(5)4-3-7(11)12/h1-2H,3-4H2,(H,11,12)
• InChIKey: IUTPJBLLJJNPAJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)propanoic acid
• IUPAC Traditional name: 3-(2,5-dioxopyrrol-1-yl)propanoic acid
• Synonyms: 2,5-Dihydro-2,5-dioxo-1H-pyrrole-1-propanoic Acid; 3-(2,5-Dioxo-2,5-dihydro-pyrrol-1-yl)-propionic Acid; N-Maleoyl-β-alanine; 3-Maleimidopropionic acid; N-(2-Carboxyethyl)maleimide; N-Maleoyl-β-alanine; 3-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)propanoic acid; 3-Maleimidopropionic acid; N-Maleoyl-β-alanine; β-MALEIMIDOPROPIONIC ACID; 3-马来酰亚胺丙酸; N-(2-羧乙基)马来酰亚胺; 3-马来酰亚胺基丙酸

Database IDs

• CAS Number: 7423-55-4
• MDL Number: MFCD00043030
• Beilstein Number: 1528952
• PubChem SID: 162032465; 24882518; 24864618
• PubChem CID: 573621

CALCULATED PROPERTIES

• Acid pKa: 3.914413
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -2.2890368
• LogD (pH = 7.4): -3.903316
• Log P: -0.6972308
• Molar Refractivity: 39.0321 cm^3
• Polarizability: 14.635779 Å^3
• Polar Surface Area: 74.68 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMF; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 103-106 °C(lit.); 104-107°C; 108-111 °C

Safety Information

• Storage Condition: -20°C Freezer; 2-8°C
• Storage Warning: IRRITANT
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• TSCA Listed: false
• 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: ≥98.0% (HPLC); 95+%; 97%
• Empirical Formula (Hill Notation): C7H7NO4

DETAILS

MP Biomedicals - 02155311

(N-Maleoyl-β-alanine) Modification reagent for thiol groups in proteins.

Sigma Aldrich - 394815

Packaging
1 g in glass bottle
250 mg in glass bottle

Sigma Aldrich - 63285

Other Notes
Reagent for the modification of peptides, proteins with an SH-label, probe for membrane SH-groups,1 Used for the preparation of peptide-protein conjugates 2,3

Toronto Research Chemicals - M140750

A sulfhydryl reactive heterobifunctional crosslinking reagent.

REFERENCES

• Rich, D., et al., J. Med. Chem., 18: 1004, (1975).
• Rich, D., et al.: J. Med. Chem., 18, 1004 (1975)
• Moroder, L., et al.: BioPolymers, 22, 481 (1983)