1-ethyl-2,5-dihydro-1H-pyrrole-2,5-dione

• ChemBase ID: 2676
• Molecular Formular: C6H7NO2
• Molecular Mass: 125.12528
• Monoisotopic Mass: 125.04767847
• SMILES: CCN1C(=O)C=CC1=O
• Canonical SMILES: CCN1C(=O)C=CC1=O
• InChI: InChI=1S/C6H7NO2/c1-2-7-5(8)3-4-6(7)9/h3-4H,2H2,1H3
• InChIKey: HDFGOPSGAURCEO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-ethyl-2,5-dihydro-1H-pyrrole-2,5-dione
• IUPAC Traditional name: N-ethylmaleimide
• Synonyms: 1-Ethyl-1H-pyrrole-2,5-dione; Maleic Acid N-Ethylimide; NSC 7638; N-Ethyl Maleimide; N-Ethylmaleimide; NEM; Maleic Acid-N-Ethylimide; USAF B-121; N-Ethylmaleimide; Ethylmaleimide; N-乙基马来酰亚胺

Database IDs

• CAS Number: 128-53-0
• EC Number: 204-892-4
• MDL Number: MFCD00005509
• Beilstein Number: 112448
• Merck Index: 143822
• PubChem SID: 24894398; 24278420; 46509138; 24845706; 160966125
• PubChem CID: 4362
• CHEBI ID: 44485
• CHEMBL: 8211
• Chemspider ID: 4209
• DrugBank ID: DB02967
• KEGG ID: C02441
• Unique Ingredient Identifier: O3C74ACM9V
• Wikipedia Title: N-Ethylmaleimide

CALCULATED PROPERTIES

JChem

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): -0.055418905
• LogD (pH = 7.4): -0.055418905
• Log P: -0.055418905
• Molar Refractivity: 32.9967 cm^3
• Polarizability: 12.134697 Å^3
• Polar Surface Area: 37.38 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.02
• LOG S: 0.31
• Solubility (Water): 2.54e+02 g/l

PROPERTIES

Physical Property

• Solubility: 95% ethanol: soluble50 mg/mL, clear to slightly hazy (colorless to faint yellow)
• Apperance: crystalline; Crystalline
• Melting Point: 43-46 °C; 43-46 °C(lit.); 43-46°C; 43-46°C
• Boiling Point: 209-211°C; 210 °C(lit.); 210°C
• Flash Point: 163.4 °F; 73 °C; 73.3°C; 73°C(163°F)

Safety Information

• Storage Condition: 2-8°C, Store Under Nitrogen
• RTECS: UX9625000
• European Hazard Symbols: Corrosive (C); Flammable (F); Highly toxic (T+)
• UN Number: 2923; 2928; UN2928
• German water hazard class: 3
• Hazard Class: 6.1; 8
• Packing Group: 2; II
• Australian Hazchem: 2X
• Risk Statements: 21-28-34-43; R:10-28-34
• Safety Statements: 20-26-28-36/37/39-45; 26-28-36/37/39-45; S:16-20-26-27/28-36/37/39-46
• EU Classification: CT2
• EU Hazard Identification Number: 8A
• Emergency Response Guidebook(ERG) Number: 154
• TSCA Listed: 是
• GHS Pictograms: GHS05; GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300-H311-H314-H317; H300-H311-H317-H314-H318
• GHS Precautionary statements: P260-P301+P310-P303+P361+P353-P305+P351+P338-P361-P405-P501A; P264-P280-P301 + P310-P305 + P351 + P338-P310; P280-P305+P351+P338-P302+P352-P309-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 2928 6.1/PG 2
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... KCNQ2(3785), KCNQ4(9132), KCNQ5(56479), SLC6A3(6531), SLC6A4(6532); human ... SLC6A3(6531), SLC6A4(6532)

Product Information

• Purity: ≥99%; ≥98% (HPLC); ≥99.0% (HPLC); 97-98%; 98+%; 99+%
• Grade: purum p.a.
• Ignition Residue: ≤0.05%; ≤0.1%
• Impurities: ≤0.001% Phosphorus (P); ≤0.1% Insoluble matter
• Cation Traces: Al: ≤0.0005%; Ca: ≤0.0005%; Ca: ≤50 mg/kg; Cd: ≤50 mg/kg; Co: ≤50 mg/kg; Cu: ≤0.0005%; Cu: ≤50 mg/kg; Fe: ≤0.0005%; Fe: ≤50 mg/kg; K: ≤0.005%; K: ≤100 mg/kg; Mg: ≤0.0005%; Na: ≤0.005%; Na: ≤100 mg/kg; Ni: ≤50 mg/kg; Pb: ≤0.001%; Pb: ≤50 mg/kg; Zn: ≤0.0005%; Zn: ≤50 mg/kg
• Antion Traces: chloride (Cl-): ≤0.05%; chloride (Cl-): ≤50 mg/kg; sulfate (SO42-): ≤0.05%; sulfate (SO42-): ≤100 mg/kg
• Quality Level: PREMIUM
• Empirical Formula (Hill Notation): C6H7NO2

DETAILS

MP Biomedicals - 02195176

Crystalline
Purity: 99+%
N-Protecting reagent. Also reacts specifically with sulfhydryl groups and can be used to determine such groups in peptides and proteins.

MP Biomedicals - 02190204

Crystalline
Purity: 97-98%

DrugBank - DB02967

• Drug Groups: experimental
• Description: A sulfhydryl reagent that is widely used in experimental biochemical studies. [PubChem]

Sigma Aldrich - 04260

Application
Reagent for the covalent modification of cysteine residues in proteins.
Biochem/physiol Actions
Augments currents from native M-channels in sympathetic neurons and acts as an opener for KCNQ2, KCNQ4 and KCNQ5 channels.
Sulfhydryl alkylating agent that inactivates NADP-dependent isocitrate dehydrogenase and many endonucleases.

Sigma Aldrich - E3876

Application
用于共价修饰蛋白质的半胱氨酸残基的试剂。
Biochem/physiol Actions
使 NADP 依赖性异柠檬酸脱氢酶和许多核酸内切酶失活的巯基烷化剂。
增强来自交感神经元的原生 M 通道的电流，并作为 KCNQ2、KCNQ4 和 KCNQ5 通道的开放剂。
Preparation Note
NEM 以 50mg/ml 的浓度溶于乙醇可得到透明的溶液。NEM 可溶于水（在 4ml 水中的溶解量 >50mg）；然而，水溶液却不稳定。水解速率为假一级，并显著依赖于 pH 值。

Sigma Aldrich - E1271

Application
用于共价修饰蛋白质的半胱氨酸残基的试剂。
Biochem/physiol Actions
使 NADP 依赖性异柠檬酸脱氢酶和许多核酸内切酶失活的巯基烷化剂。
增强来自交感神经元的原生 M 通道的电流，并作为 KCNQ2、KCNQ4 和 KCNQ5 通道的开放剂。

Toronto Research Chemicals - E817900

Reagent for the covalent modification of cysteine residues in proteins.NEM gives a clear solution in ethanol at 50 mg/ml. NEM dissolves in water (>50 mg in 4 ml); however, aqueous solutions are unstable. The rate of hydrolysis is pseudo-first order and si

REFERENCES

• Sheehan, M., et al.: J. Cell Biol., 106, 1 (1988)
• Vogel, K., et al.: J. Biol. Chem., 275, 2959 (1988)
• Ramos, C., et al.: Biochem. J., 400, 393 (1988)
• Reactive dienophile and dipolarophile. Reagent for modification of sulfhydryl groups of cysteine residues in proteins: Methods Enzymol., 25, 449 (1972); Eur. J. Biochem., 145, 245 (1984).