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Key Documents

E1271

Sigma-Aldrich

N-Ethylmaleimide

BioXtra, ≥98% (HPLC)

Synonym(s):

NEM

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About This Item

Empirical Formula (Hill Notation):
C6H7NO2
CAS Number:
Molecular Weight:
125.13
Beilstein:
112448
EC Number:
MDL number:
UNSPSC Code:
12352106
PubChem Substance ID:
NACRES:
NA.21

product line

BioXtra

Quality Level

Assay

≥98% (HPLC)

impurities

≤0.001% Phosphorus (P)
≤0.1% Insoluble matter

ign. residue

≤0.1%

bp

210 °C (lit.)

mp

43-46 °C (lit.)

solubility

95% ethanol: 50 mg/mL, clear to slightly hazy (colorless to faint yellow)

anion traces

chloride (Cl-): ≤0.05%
sulfate (SO42-): ≤0.05%

cation traces

Al: ≤0.0005%
Ca: ≤0.0005%
Cu: ≤0.0005%
Fe: ≤0.0005%
K: ≤0.005%
Mg: ≤0.0005%
Na: ≤0.005%
Pb: ≤0.001%
Zn: ≤0.0005%

storage temp.

2-8°C

SMILES string

CCN1C(=O)C=CC1=O

InChI

1S/C6H7NO2/c1-2-7-5(8)3-4-6(7)9/h3-4H,2H2,1H3

InChI key

HDFGOPSGAURCEO-UHFFFAOYSA-N

Gene Information

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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.

Pictograms

Skull and crossbonesCorrosion

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 2 Oral - Acute Tox. 3 Dermal - Eye Dam. 1 - Skin Corr. 1B - Skin Sens. 1

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

163.2 °F - closed cup

Flash Point(C)

72.9 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Tatsuki Kurokawa et al.
Biochimica et biophysica acta, 1838(1 Pt B), 382-387 (2013-10-22)
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Nicolas Matuszak et al.
Journal of medicinal chemistry, 52(23), 7410-7420 (2009-07-09)
The endocannabinoid 2-arachidonoylglycerol (2-AG) plays a major role in many physiological processes, and its action is quickly terminated via enzymatic hydrolysis catalyzed by monoglyceride lipase (MGL). Regulating its endogenous level could offer therapeutic opportunities; however, few selective MGL inhibitors have
Hannah E Boycott et al.
Proceedings of the National Academy of Sciences of the United States of America, 110(41), E3955-E3964 (2013-09-26)
Atrial myocytes are continuously exposed to mechanical forces including shear stress. However, in atrial myocytes, the effects of shear stress are poorly understood, particularly with respect to its effect on ion channel function. Here, we report that shear stress activated
Florian A Salomons et al.
Molecular and cellular biology, 29(7), 1774-1785 (2009-01-23)
Conditions causing an increase in misfolded or aberrant proteins can impair the activity of the ubiquitin/proteasome system (UPS). This observation is of particular interest, given the fact that proteotoxic stress is closely associated with a large variety of disorders. Although
Julia Kuligowski et al.
Talanta, 127, 181-190 (2014-06-11)
Liquid chromatography-mass spectrometry (LC-MS) has been increasingly used in biomedicine to study the dynamic metabolomic responses of biological systems under different physiological or pathological conditions. To obtain an integrated snapshot of the system, metabolomic methods in biomedicine typically analyze biofluids

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