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
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.
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.
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 |
