DIETHYL MALEATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C8H12O4
Molecular Weight	172.1785
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=IEPRKVQEAMIZSS-WAYWQWQTSA-N

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

HIDE SMILES / InChI

Molecular Formula	C8H12O4
Molecular Weight	172.1785
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

Approval Year

PubMed

Title	Date	PubMed
A novel toxicogenomics-based approach to categorize (non-)genotoxic carcinogens.	2015-12	25270620
Genes specifically modulated in sensitized skins allow the detection of sensitizers in a reconstructed human skin model. Development of the SENS-IS assay.	2015-06	25724174
Role of PKC-β in chemical allergen-induced CD86 expression and IL-8 release in THP-1 cells.	2014-02	24136171
NCTC 2544 and IL-18 production: a tool for the identification of contact allergens.	2013-04	23063874
Genetic damage, but limited evidence of oxidative stress markers in diethyl maleate-induced glutathione depleted mouse lymphoma L5178Y (TK(+/-)) cell cultures.	2012-09	22564015
Isoeugenol destabilizes IL-8 mRNA expression in THP-1 cells through induction of the negative regulator of mRNA stability tristetraprolin.	2012-02	21969073
The ToxTracker assay: novel GFP reporter systems that provide mechanistic insight into the genotoxic properties of chemicals.	2012-01	22003191
An in vitro test to screen skin sensitizers using a stable THP-1-derived IL-8 reporter cell line, THP-G8.	2011-12	21920952
Rat H9c2 cardiac myocytes are sensitive to arsenite due to a modest activation of transcription factor Nrf2.	2011-12	21465251
Relating skin sensitizing potency to chemical reactivity: reactive Michael acceptors inhibit NF-κB signaling and are less sensitizing than S(N)Ar- and S(N)2- reactive chemicals.	2011-11-21	22023385
Hepatic transcriptome and proteome responses against diethyl maleate-induced glutathione depletion in the rat.	2011-09	21161181
Nrf2 regulates ferroportin 1-mediated iron efflux and counteracts lipopolysaccharide-induced ferroportin 1 mRNA suppression in macrophages.	2011-04-01	21303654
Structure-activity comparison of the cytotoxic properties of diethyl maleate and related molecules: identification of diethyl acetylenedicarboxylate as a thiol cross-linking agent.	2011-01-14	21105742
Regulation of human carbonyl reductase 3 (CBR3; SDR21C2) expression by Nrf2 in cultured cancer cells.	2010-10-05	20806931
Use of IL-8 release and p38 MAPK activation in THP-1 cells to identify allergens and to assess their potency in vitro.	2010-09	20541004
A new in vitro method for identifying chemical sensitizers combining peptide binding with ARE/EpRE-mediated gene expression in human skin cells.	2010-09	20491607
Protein thiol oxidation in murine airway epithelial cells in response to naphthalene or diethyl maleate.	2010-09	19843705
Dual mechanisms of NF-kappaB inhibition in carnosol-treated endothelial cells.	2010-05-15	20116392
Dissecting the signaling events that impact classical nuclear import and target nuclear transport factors.	2009-12-24	20041180
Peroxiredoxin 2 and peroxidase enzymatic activity of mammalian spermatozoa.	2009-06	19208552
The effect of insecticide synergists on the response of scabies mites to pyrethroid acaricides.	2009	19125173
Tumor necrosis factor-associated protein 1 (TRAP-1) protects cells from oxidative stress and apoptosis.	2007-11	17853063
The dietary antioxidant resveratrol affects redox changes of PPARalpha activity.	2007-05	17134953
Increased expression of the MGMT repair protein mediated by cysteine prodrugs and chemopreventative natural products in human lymphocytes and tumor cell lines.	2007-02	16950796
Transcriptional regulation of thioredoxin reductase 1 expression by cadmium in vascular endothelial cells: role of NF-E2-related factor-2.	2005-06	15521073
Effect of acrolein and glutathione depleting agents on thioredoxin.	2004-11-15	15388247
Spatial activities and induction of glutamate-cysteine ligase (GCL) in the postimplantation rat embryo and visceral yolk sac.	2004-10	15115889
Mechanisms for sensitization to TNF-induced apoptosis by acute glutathione depletion in murine hepatocytes.	2003-06	12774022
Native tesmin is a 60-kilodalton protein that undergoes dynamic changes in its localization during spermatogenesis in mice.	2003-05	12606435
Electrophile response element-mediated induction of the cystine/glutamate exchange transporter gene expression.	2002-11-22	12235164
Reduced glutathione depletion causes necrosis and sensitization to tumor necrosis factor-alpha-induced apoptosis in cultured mouse hepatocytes.	2002-07	12085349
Transcriptional and physiological responses of HepG2 cells exposed to diethyl maleate: time course analysis.	2002-02-28	11875189
Glutathione depletion induces apoptosis of rat hepatocytes through activation of protein kinase C novel isoforms and dependent increase in AP-1 nuclear binding.	2000-12-15	11118818
Inducers of gamma-glutamylcysteine synthetase and their effects on glutathione synthetase expression.	2000-09-07	10978506
Hepatocellular response to chemical stress in CD-1 mice: induction of early genes and gamma-glutamylcysteine synthetase.	2000-08	10915739
Induction of metalloelastase mRNA in murine peritoneal macrophages by diethylmaleate.	1999-04-19	10216232
Expression of inducible nitric oxide synthase in endotoxemic rat hepatocytes is dependent on the cellular glutathione status.	1999-02	9918918
Thiol modulation of TNF alpha and IL-1 induced MnSOD gene expression and activation of NF-kappa B.	1995-07-05	7476933
Regulation of hepatic nitric oxide synthase by reactive oxygen intermediates and glutathione.	1995-02-01	7532384
The radiosensitizing effects of misonidazole (MISO) in combination with diethyl maleate (DEM) in mouse mammary tumors.	1986-10	3759535
Detoxifying activities in alveolar macrophages of rats treated with acetylcysteine, diethyl maleate and/or aroclor.	1986-09-01	3099627
Cytotoxicity of halogenated alkanes in primary cultures of rat hepatocytes from normal, partial hepatectomized, and preneoplastic/neoplastic liver.	1985-09-15	2862719
Paradoxical effects of perturbation of intracellular levels of glutathione on halothane-induced hepatotoxicity in hyperthyroid rats.	1984-04	6724195
Lipid peroxidation: a possible mechanism of cephaloridine-induced nephrotoxicity.	1983-01	6845359
Antifungal properties of 2-bromo-3-fluorosuccinic acid esters and related compounds.	1977-04	321785

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 21:18:43 GMT 2025` Edited by `admin` on `Mon Mar 31 21:18:43 GMT 2025`
Record UNII	G81WQB56OL
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DIETHYL MALEATE

Systematic Name

English

STAFLEX DEM

Preferred Name

English

(2Z)-2-BUTENEDIOIC ACID, 1,4-DIETHYL ESTER

Common Name

English

NSC-8394

Code

English

MALEIC ACID, DIETHYL ESTER

Common Name

English

DIETHYL MALEATE [MI]

Common Name

English

DIETHYL (Z)-2-BUTENEDIOATE

Systematic Name

English

Code System Code Type Description

MERCK INDEX

m4409