2,5-dioxopyrrolidin-1-yl 3-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)propanoate

• ChemBase ID: 66715
• Molecular Formular: C11H10N2O6
• Molecular Mass: 266.2069
• Monoisotopic Mass: 266.05388605
• SMILES: C(=O)(CCN1C(=O)C=CC1=O)ON1C(=O)CCC1=O
• Canonical SMILES: O=C(ON1C(=O)CCC1=O)CCN1C(=O)C=CC1=O
• InChI: InChI=1S/C11H10N2O6/c14-7-1-2-8(15)12(7)6-5-11(18)19-13-9(16)3-4-10(13)17/h1-2H,3-6H2
• InChIKey: JKHVDAUOODACDU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,5-dioxopyrrolidin-1-yl 3-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)propanoate
• IUPAC Traditional name: 2,5-dioxopyrrolidin-1-yl 3-(2,5-dioxopyrrol-1-yl)propanoate
• Synonyms: N-(3-Maleimidopropionyloxy)succinimide; N-Maleoyl-β-alanine N′-hydroxysuccinimide ester; N-Maleoyl-β-alanine N-hydroxysuccinimide ester; N-Succinimidyl 3-maleimidopropionate; BMPS; 3-Maleimidopropionic acid N-hydroxysuccinimide ester; 3-(Maleimido)propionic acid N-succinimidyl ester; 3-(Maleimido)propionic acid N-hydroxysuccinimide ester; 2,5-Dihydro-2,5-dioxo-1H-pyrrole-1-propanoic Acid 2,5-Dioxo-1-pyrrolidinyl Ester; 3-Maleimidopropionic Acid N-Hydroxysuccinimide Ester; N-Succinimidyl 3-(N-Maleimido)propionate; 3-Maleimidopropionic Acid N-Succinimidyl Ester; 3-(Maleimido)propionic acid N-hydroxysuccinimide ester; 3-马来酰亚胺丙酸 N-羟基琥珀酰亚胺酯

Database IDs

• CAS Number: 55750-62-4
• MDL Number: MFCD00043141
• Beilstein Number: 1492578
• PubChem SID: 24861980; 162032451; 24882447
• PubChem CID: 4620597

CALCULATED PROPERTIES

• Acid pKa: 17.708893
• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): -1.3276454
• LogD (pH = 7.4): -1.3276454
• Log P: -1.3276454
• Molar Refractivity: 59.5859 cm^3
• Polarizability: 22.923098 Å^3
• Polar Surface Area: 101.06 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 167-171 °C; 168-170 °C(lit.); 168-170°C; 171°C

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere
• Storage Warning: IRRITANT; Moisture Sensitive
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38; 37
• Safety Statements: 26-37-60
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335; H335
• GHS Precautionary statements: P261; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.5% (HPLC); 95+%; 98%; 99%
• Empirical Formula (Hill Notation): C11H10N2O6

DETAILS

Sigma Aldrich - 358657

Packaging
25 mg in glass bottle

Sigma Aldrich - 63179

Other Notes
Aliphatic cross-linking reagent of hetero-bifunctional type. Acylation at pH 8 proceeds most selectively whereas the stability of the maleimido group is much better compared to aromatic derivative 1 Used for the cross-linking of haptens to enzymes prior to enzyme immunoassays or fluorogenic substrates to peptidic antigens for use in fluorescence immunoassays 2

Toronto Research Chemicals - M141000

A short, sulfhydryl and amino reactive heterobifunctional crosslinking reagent. Also used in immunodiagnostics.Spacer Arm: 6.9 Angstroms

REFERENCES

• Kitagawa, T., el al.: Enz. Immunoassay, 81, (1981)
• Sulfhydryl- (SH) and amino-reactive heterobifunctional cross-linking agent: Enzym. Immunoassay, 81 (1981); J. Immunol. Meth., 62, 123 (1983). Applications in immunodiagnostics: Biopolymers, 22, 481 (1983).