N-ethylmaleimide

Base Information

• Chemical Name: N-ethylmaleimide
• CAS No.: 128-53-0
• Molecular Formula: C6H7NO2
• Molecular Weight: 125.127
• Hs Code.: 29251900
• European Community (EC) Number: 204-892-4
• NSC Number: 92547,7638
• UNII: O3C74ACM9V
• DSSTox Substance ID: DTXSID1059573
• Nikkaji Number: J21.254G
• Wikipedia: N-Ethylmaleimide
• Wikidata: Q292393
• Metabolomics Workbench ID: 49817
• ChEMBL ID: CHEMBL8211
• Mol file: 128-53-0.mol

Synonyms:Ethylmaleimide;N Ethylmaleimide;N-Ethylmaleimide

Chemical Property of N-ethylmaleimide

Chemical Property:

• Appearance/Colour: White solid
• Vapor Pressure: 0.197mmHg at 25°C
• Melting Point: 43-46 °C(lit.)
• Refractive Index: 1.514
• Boiling Point: 210 °C at 760 mmHg
• PKA: -2.18±0.20(Predicted)
• Flash Point: 73.3 °C
• PSA: 37.38000
• Density: 1.207 g/cm³
• LogP: -0.13080
• Storage Temp.: 2-8°C
• Sensitive.: Light Sensitive
• Solubility.: methanol: 1 M at 20 °C, clear, colorless
• Water Solubility.: 1 g/L (20 ºC)
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 125.047678466
• Heavy Atom Count: 9
• Complexity: 166

Purity/Quality:

98%, ^*data from raw suppliers

N-Ethylmaleimide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+
• Hazard Codes: T+
• Statements: 21-28-34-43-20/21
• Safety Statements: 26-28-36/37/39-45-28A

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Uses -> Biochemical Research
• Canonical SMILES: CCN1C(=O)C=CC1=O
• Recent ClinicalTrials: NEM? Versus Placebo on Exercise-induced Joint Pain, Stiffness, & Cartilage Turnover In Healthy, Post-Menopausal Women
• Uses: 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 significantly dependent on pH. In cancer research (possible antimitotic activity.) N-Ethylmaleimide is a protein thiol modifier which inhibits apoptotic DNA fragmentation. It is a sulfhydryl reagent and finds application in experimental biochemical studies as well as in enzymology. It is involved in the modification of cysteine residues in proteins and peptides. It acts as a Michael acceptor and reacts with nucelophiles like thiols. It is employed in the inhibition of Mg2+ dependent internucleosomal DNA fragmentation.

Technology Process of N-ethylmaleimide

There total 13 articles about N-ethylmaleimide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 85.0%

maleic anhydride (108-31-6) + ethylamine (75-04-7,85404-22-4) → N-Ethylmaleimide (128-53-0)

Guidance literature:

With sulfuric acid; copper(II) sulfate; sodium sulfate; In 5,5-dimethyl-1,3-cyclohexadiene; at 140 ℃; for 2h;

DOI:10.1002/ardp.201600047

Reference yield: 52.0%

3-Pyrroline (109-96-6,760178-50-5) + ethyl bromide (74-96-4) → N-Ethylmaleimide (128-53-0)

Guidance literature:

With DBN; oxygen; rose bengal; In N,N-dimethyl-formamide; at 20 ℃; for 48h; Irradiation;

DOI:10.1021/acscatal.8b01897

Reference yield:

C11H15NO3 → 2-methylfuran (534-22-5) + N-Ethylmaleimide (128-53-0)

Guidance literature:

In [D₃]acetonitrile; at 60 ℃; Kinetics;

DOI:10.1002/anie.200805303

upstream raw materials:

N-ethyl maleamic acid

2-ethyl-4-methyl-hexahydro-4,7-epioxido-isoindole-1,3-dione

maleic anhydride

ethanamine hydrochloride

Downstream raw materials:

3-(4-chloro-phenyl)-1-ethyl-pyrrole-2,5-dione

2-(1-ethyl-2,5-dioxo-pyrrolidin-3-ylmercapto)-benzoic acid

2-ethyl-3a,4,7,7a-tetrahydroisoindole-1,3-dione

Refernces

Synthesis and characterization of cis-4-decenoyl-CoA, 3-phenylpropionyl-CoA, and 2,6-dimethylheptanoyl-CoA

10.1016/j.ab.2010.02.026

The research focuses on the development of a method for synthesizing three medium-chain acyl-CoAs from unsaturated and less common fatty acids that are not commercially available. The key chemicals involved in this research include cis-4-decen-1-al, hydrocinnamic acid (3-phenylpropionic acid), anhydrous ethylchloroformate, ammonium formate, silver nitrate, thionyl chloride, 6-methyl-2-heptanol, p-toluenesulfonyl chloride, potassium phosphate, cytochrome c, potassium cyanide, phenazine ethosulfate, N-ethylmaleimide, rotenone, and CoASH (coenzyme A trilithium salt). These chemicals play crucial roles in the synthesis of the fatty acids and the subsequent formation of the acyl-CoAs. For instance, ethylchloroformate is used to form mixed anhydrides of the fatty acids, which are then reacted with CoASH to produce the desired acyl-CoAs. The study also employs various solvents such as methanol, acetonitrile, and tetrahydrofuran, as well as reagents for purification and characterization processes like 2-(2-pyridyl)ethyl-functionalized silica gel for solid-phase extraction and ammonium formate for HPLC elution. The synthesized acyl-CoAs are characterized using techniques such as gas chromatography/mass spectrometry (GC/MS), nuclear magnetic resonance (NMR), and high-performance liquid chromatography with ultraviolet detection and tandem mass spectrometry (HPLC–UV–MS–MS/MS). The purified acyl-CoAs are then used as substrates for measuring acyl-CoA dehydrogenase activities in rat skeletal muscle mitochondria, providing valuable insights into the enzymatic activities related to fatty acid oxidation.