U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of DIETHYL MALEATE

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

Approval Year

Unknown
139594
PubMed

PubMed

TitleDatePubMed
Antifungal properties of 2-bromo-3-fluorosuccinic acid esters and related compounds.
1977 Apr
Paradoxical effects of perturbation of intracellular levels of glutathione on halothane-induced hepatotoxicity in hyperthyroid rats.
1984 Apr
Regulation of hepatic nitric oxide synthase by reactive oxygen intermediates and glutathione.
1995 Feb 1
Induction of metalloelastase mRNA in murine peritoneal macrophages by diethylmaleate.
1999 Apr 19
Hepatocellular response to chemical stress in CD-1 mice: induction of early genes and gamma-glutamylcysteine synthetase.
2000 Aug
Inducers of gamma-glutamylcysteine synthetase and their effects on glutathione synthetase expression.
2000 Sep 7
Transcriptional and physiological responses of HepG2 cells exposed to diethyl maleate: time course analysis.
2002 Feb 28
Spatial activities and induction of glutamate-cysteine ligase (GCL) in the postimplantation rat embryo and visceral yolk sac.
2004 Oct
Dissecting the signaling events that impact classical nuclear import and target nuclear transport factors.
2009 Dec 24
Peroxiredoxin 2 and peroxidase enzymatic activity of mammalian spermatozoa.
2009 Jun
Use of IL-8 release and p38 MAPK activation in THP-1 cells to identify allergens and to assess their potency in vitro.
2010 Sep
An in vitro test to screen skin sensitizers using a stable THP-1-derived IL-8 reporter cell line, THP-G8.
2011 Dec
Rat H9c2 cardiac myocytes are sensitive to arsenite due to a modest activation of transcription factor Nrf2.
2011 Dec
Structure-activity comparison of the cytotoxic properties of diethyl maleate and related molecules: identification of diethyl acetylenedicarboxylate as a thiol cross-linking agent.
2011 Jan 14
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 Nov 21
Hepatic transcriptome and proteome responses against diethyl maleate-induced glutathione depletion in the rat.
2011 Sep
The ToxTracker assay: novel GFP reporter systems that provide mechanistic insight into the genotoxic properties of chemicals.
2012 Jan
Genetic damage, but limited evidence of oxidative stress markers in diethyl maleate-induced glutathione depleted mouse lymphoma L5178Y (TK(+/-)) cell cultures.
2012 Sep
Role of PKC-β in chemical allergen-induced CD86 expression and IL-8 release in THP-1 cells.
2014 Feb
Patents

Patents

04221776
14
04457982
3
04464352
2
04546110
2
04595521
8
04663319
3
04795824
2
04919765
2
05030328
7
05163995
2
05322948
2
05364955
3
05405987
4
05536856
2
05798054
2
05808067
2
06063863
3
06077901
2
06111010
3
06444325
2
06942966
2
07211270
2
07241767
2
JP2001520247A
4
JP2003517028A
14
JP2003532556A
4
JP2004513913A
5
JP2004520474A
17
JP2006502290A
2
JP2006525402A
4
JP2007502893A
4
JP2007511658A
17
JP2008520815A
23
JP2009500422A
2
JP4290994B2
17
JPH02101089A
14
JPH02173051A
2
JPH04110310A
2
JPH04327565A
2
JPH07285898A
2
JPH0827063A
2
JPH08311146A
2
JPH09124553A
2
JPH0959216A
2
JPH10251208A
3
JPH1087828A
2
JPH11279007A
2
JPS5447882A
2
JPS5490338A
2
JPS5543168A
2
JPS5789751A
2
JPS61169287A
2
JPS6163616A
3
JPS6272709A
4
Name Type Language
DIETHYL MALEATE
MI  
Systematic Name English
(2Z)-2-BUTENEDIOIC ACID, 1,4-DIETHYL ESTER
Common Name English
NSC-8394
Code English
STAFLEX DEM
Brand Name 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
Created by admin on Sat Dec 16 03:27:59 GMT 2023 , Edited by admin on Sat Dec 16 03:27:59 GMT 2023
PRIMARY Merck Index
PUBCHEM
5271566
Created by admin on Sat Dec 16 03:27:59 GMT 2023 , Edited by admin on Sat Dec 16 03:27:59 GMT 2023
PRIMARY
CAS
141-05-9
Created by admin on Sat Dec 16 03:27:59 GMT 2023 , Edited by admin on Sat Dec 16 03:27:59 GMT 2023
PRIMARY
CHEBI
68508
Created by admin on Sat Dec 16 03:27:59 GMT 2023 , Edited by admin on Sat Dec 16 03:27:59 GMT 2023
PRIMARY
ECHA (EC/EINECS)
205-451-9
Created by admin on Sat Dec 16 03:27:59 GMT 2023 , Edited by admin on Sat Dec 16 03:27:59 GMT 2023
PRIMARY
EVMPD
SUB177369
Created by admin on Sat Dec 16 03:27:59 GMT 2023 , Edited by admin on Sat Dec 16 03:27:59 GMT 2023
PRIMARY
EPA CompTox
DTXSID8020464
Created by admin on Sat Dec 16 03:27:59 GMT 2023 , Edited by admin on Sat Dec 16 03:27:59 GMT 2023
PRIMARY
MESH
C014476
Created by admin on Sat Dec 16 03:27:59 GMT 2023 , Edited by admin on Sat Dec 16 03:27:59 GMT 2023
PRIMARY
WIKIPEDIA
Diethyl maleate
Created by admin on Sat Dec 16 03:27:59 GMT 2023 , Edited by admin on Sat Dec 16 03:27:59 GMT 2023
PRIMARY
FDA UNII
G81WQB56OL
Created by admin on Sat Dec 16 03:27:59 GMT 2023 , Edited by admin on Sat Dec 16 03:27:59 GMT 2023
PRIMARY
SMS_ID
100000163227
Created by admin on Sat Dec 16 03:27:59 GMT 2023 , Edited by admin on Sat Dec 16 03:27:59 GMT 2023
PRIMARY
NSC
8394
Created by admin on Sat Dec 16 03:27:59 GMT 2023 , Edited by admin on Sat Dec 16 03:27:59 GMT 2023
PRIMARY
SUBSTANCE RECORD
Structure of DIETHYL MALEATE
NIH
NCATS
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