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Key Documents

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:
Molecular Weight:
172.18
Beilstein:
1100825
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

vapor density

5.93 (vs air)

Quality Level

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

Signal Word

Warning

Hazard Statements

Hazard Classifications

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

Storage Class Code

10 - Combustible liquids

WGK

WGK 2

Flash Point(F)

200.1 °F - closed cup

Flash Point(C)

93.4 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
Yosuke Hirotsu et al.
Nucleic acids research, 40(20), 10228-10239 (2012-09-12)
NF-E2-related factor 2 (Nrf2) is a key transcription factor that is critical for cellular defense against oxidative and xenobiotic insults. Nrf2 heterodimerizes with small Maf (sMaf) proteins and binds to antioxidant response elements (AREs) to activate a battery of cytoprotective
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
Nobuhiko Harada et al.
Archives of biochemistry and biophysics, 508(1), 101-109 (2011-02-10)
Iron is an essential element of hemoglobin, and efficient iron recycling from senescent erythrocytes by splenic macrophages is required for erythrocyte hemoglobin synthesis during erythropoiesis. Ferroportin 1 (Fpn1) is the sole iron exporter in mammals, and it also regulates iron

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