N-Ethylmaleimide

Product Information

Molecular Formula:
C6H7NO2
Molecular Weight:
125.13
Description
N-Ethylmaleimide (NEM) is a derivative of maleic acid and is used as a reagent for alkylation and covalent modification of nucleophilic thiol residues on proteins. It acts as an irreversible inhibitor of all cysteine peptidases that alkylates the active site thiol group of the enzymes.
Synonyms
NEM; 1-Ethyl-1H-pyrrole-2,5-dione; ethylmaleimide
IUPAC Name
1-ethylpyrrole-2,5-dione
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
InChI Key
HDFGOPSGAURCEO-UHFFFAOYSA-N
Boiling Point
210 °C(lit.)
Melting Point
45-46°C
Flash Point
73 °C
Purity
>98.0%(HPLC)(N)
Density
1.2500 (rough estimate)
Appearance
White Solid
Application
Used in cancer research; A sulfhydryl reagent that is widely used in experimental biochemical studies.
Storage
0-10°C
Refractive Index
1.4430 (estimate)

Safety Information

Hazards
H300:
Fatal if swallowed.
H311:
Toxic in contact with skin.
H314:
Causes severe skin burns and eye damage.
H317:
May cause an allergic skin reaction.
Precautionary Statement
P260:
Do not breathe dust, fumes, gas, mist, vapours, spray.
P280:
Wear protective gloves/protective clothing/eye protection/face protection.
P301+P310+P330:
IF SWALLOWED:
Immediately call a POISON CENTER or doctor/physician.
Rinse mouth.
P303+P361+P353:
IF ON SKIN (or hair):
Take off immediately all contaminated clothing. [As modified by IV ATP].
Rinse skin with water/shower.
P304+P340+P310:
IF INHALED:
Remove person to fresh air and keep comfortable for breathing.
Immediately call a POISON CENTER or doctor/physician.
P305+P351+P338+P310:
IF IN EYES:
Rinse cautiously with water for several minutes.
Remove contact lenses if present and easy to do. Continue rinsing.
Immediately call a POISON CENTER or doctor/physician.

Computed Properties

XLogP3
0.9
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
1
Exact Mass
125.047678466 g/mol
Monoisotopic Mass
125.047678466 g/mol
Topological Polar Surface Area
37.4Ų
Heavy Atom Count
9
Formal Charge
0
Complexity
166
Isotope Atom Count
0
Defined Atom Stereocenter Count
0
Undefined Atom Stereocenter Count
0
Defined Bond Stereocenter Count
0
Undefined Bond Stereocenter Count
0
Covalently-Bonded Unit Count
1
Compound Is Canonicalized
Yes

Patents

Publication Number Title Priority Date
WO-2021122185-A1 Reversible cell detection via mhc with conjugates having an enzymatically cleavable detection moiety 2019-12-20
WO-2021123186-A1 Multi-specific antibody with binding specificity for human il-13 and il-17 2019-12-20
WO-2021123202-A1 Formulations of anti-pd1 antibodies 2019-12-20
WO-2021123244-A1 Multi-specific antibodies 2019-12-20
WO-2021125866-A1 Method for safely producing botulinum neurotoxin 2019-12-18
EP-3835378-A1 Two component (2k) curable adhesive composition 2019-12-13
EP-3835381-A1 Two component (2k) curable adhesive composition 2019-12-13
WO-2021115772-A1 Two component (2k) curable adhesive composition 2019-12-13
WO-2021115773-A1 Two component (2k) curable adhesive composition 2019-12-13
WO-2021118796-A1 Biomarkers for the diagnosis of atrial fibrillation cause of stroke 2019-12-13

Literatures

PMID Publication Date Title Journal
32006539 2020-04-25 Gastroprotective properties of Lupeol-derived ester: Pre-clinical evidences of Lupeol-stearate as a potent antiulcer agent Chemico-biological interactions
26060329 2015-06-09 SUMO deconjugation is required for arsenic-triggered ubiquitylation of PML Science signaling
25569083 2015-01-05 Elucidating mechanisms of toxicity using phenotypic data from primary human cell systems--a chemical biology approach for thrombosis-related side effects International journal of molecular sciences
25451594 2014-12-05 Gastroprotective effects of goniothalamin against ethanol and indomethacin-induced gastric lesions in rats: Role of prostaglandins, nitric oxide and sulfhydryl compounds Chemico-biological interactions
24337826 2014-04-01 Geraniol-a flavoring agent with multifunctional effects in protecting the gastric and duodenal mucosa Naunyn-Schmiedeberg's archives of pharmacology
23370007 2013-03-08 APE1/Ref-1 prevents oxidative inactivation of ERK for G1-to-S progression following lead acetate exposure Toxicology
24213000 2013-01-01 Knockdown of the gene for homeobox protein HOXB13 reduces toxicity of oxidative-stress inducers in HEK293 cells The Journal of toxicological sciences
22796344 2012-11-15 Species-specific differences in the inhibition of human and zebrafish 11β-hydroxysteroid dehydrogenase 2 by thiram and organotins Toxicology
22076955 2012-11-01 Pathways for plasmalemmal repair mediated by PKA, Epac, and cytosolic oxidation in rat B104 cells in vitro and rat sciatic axons ex vivo Developmental neurobiology
22747884 2012-11-01 Nitric oxide potentiation of the homomeric ρ1 GABA(C) receptor function British journal of pharmacology
The molarity calculator equation

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

The dilution calculator equation

Concentration (start) × Volume (start) = Concentration (final) × Volume (final)

This equation is commonly abbreviated as: C1V1 = C2V2

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