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D97703

Sigma-Aldrich

Diethyl maleate

97%

Synonym(s):

Maleic acid diethyl ester

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About This Item

Linear Formula:
C2H5OCOCH=CHCOOC2H5
CAS Number:
141-05-9
Molecular Weight:
172.18
Beilstein/REAXYS Number:
1100825
EC Number:
205-451-9
MDL number:
MFCD00009191
UNSPSC Code:
12352100
PubChem Substance ID:
24894328
NACRES:
NA.22

vapor density

5.93 (vs air)

vapor pressure

1 mmHg ( 14 °C)

assay

97%

form

liquid

autoignition temp.

662 °F

refractive index

n20/D 1.441 (lit.)

bp

225 °C (lit.)

mp

−10 °C (lit.)

density

1.064 g/mL at 25 °C (lit.)

SMILES string

CCOC(=O)\C=C/C(=O)OCC

InChI

1S/C8H12O4/c1-3-11-7(9)5-6-8(10)12-4-2/h5-6H,3-4H2,1-2H3/b6-5-

InChI key

IEPRKVQEAMIZSS-WAYWQWQTSA-N

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General description

Diethyl maleate is an ester derived from maleic anhydride, used as a building block in the synthesis of pyromellitic acid.

Application


  • Retrospective analysis of pesticide metabolites in urine using liquid chromatography coupled to high-resolution mass spectrometry.: This study highlights the use of diethyl maleate in the analysis of pesticide metabolites, demonstrating its application in high-resolution mass spectrometry for detecting urinary pesticide metabolites (Lapez et al., 2016).

  • Diethyl maleate inhibits MCA+TPA transformed cell growth via modulation of GSH, MAPK, and cancer pathways.: Research on the inhibition of cancer cell growth by diethyl maleate, focusing on its effects on glutathione, MAPK pathways, and its potential therapeutic applications in cancer treatment (Priya et al., 2014).

  • Hepatic transcriptome and proteome responses against diethyl maleate-induced glutathione depletion in the rat.: This study explores the effects of diethyl maleate on liver cells, emphasizing its role in depleting glutathione and its implications for oxidative stress and liver toxicity (Yamauchi et al., 2011).

  • Application of the BIRD sandwich for the rapid and accurate determination of (1)H-(1)H NMR coupling constants in higher order spin systems.: This paper discusses the innovative application of diethyl maleate in NMR spectroscopy for accurate determination of coupling constants, enhancing the analysis of complex spin systems (Williamson et al., 2000).

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Aquatic Chronic 3 - Eye Irrit. 2 - Skin Sens. 1

Storage Class

10 - Combustible liquids

wgk_germany

WGK 2

flash_point_f

200.1 °F - closed cup

flash_point_c

93.4 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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Sustainable production of pyromellitic acid with pinacol and diethyl maleate
Yancheng H et al.
Green Chemistry, 19, 1663-1667 (2017)
David Guerrero-Gómez et al.
Cell death and differentiation, 26(9), 1545-1565 (2019-02-17)
In the presence of aggregation-prone proteins, the cytosol and endoplasmic reticulum (ER) undergo a dramatic shift in their respective redox status, with the cytosol becoming more oxidized and the ER more reducing. However, whether and how changes in the cellular
R Faraonio et al.
Cell death and differentiation, 19(4), 713-721 (2011-11-05)
Here we show that replicative senescence in normal human diploid IMR90 fibroblasts is accompanied by altered expression of a set of microRNAs (miRNAs) (senescence-associated miRNAs), with 14 and 10 miRNAs being either up or downregulated (>2-fold), respectively, in senescent with
Lauren Drowley et al.
Molecular therapy : the journal of the American Society of Gene Therapy, 18(10), 1865-1873 (2010-07-29)
Although cellular transplantation has been shown to promote improvements in cardiac function following injury, poor cell survival following transplantation continues to limit the efficacy of this therapy. We have previously observed that transplantation of muscle-derived stem cells (MDSCs) improves cardiac
Nazir M Khan et al.
Free radical biology & medicine, 51(1), 115-128 (2011-05-03)
There are no reports describing the ability of pro-oxidants to protect against radiation-induced apoptosis. Activation of the redox-sensitive transcription factor Nrf2 by low levels of ROS is known to protect against oxidative stress-induced cell death. In this study, hydrogen peroxide
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