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
Antifungal properties of 2-bromo-3-fluorosuccinic acid esters and related compounds.	1977 Apr	321785
Paradoxical effects of perturbation of intracellular levels of glutathione on halothane-induced hepatotoxicity in hyperthyroid rats.	1984 Apr	6724195
Regulation of hepatic nitric oxide synthase by reactive oxygen intermediates and glutathione.	1995 Feb 1	7532384
Thiol modulation of TNF alpha and IL-1 induced MnSOD gene expression and activation of NF-kappa B.	1995 Jul 5	7476933
Induction of metalloelastase mRNA in murine peritoneal macrophages by diethylmaleate.	1999 Apr 19	10216232
Expression of inducible nitric oxide synthase in endotoxemic rat hepatocytes is dependent on the cellular glutathione status.	1999 Feb	9918918
Reduced glutathione depletion causes necrosis and sensitization to tumor necrosis factor-alpha-induced apoptosis in cultured mouse hepatocytes.	2002 Jul	12085349
Mechanisms for sensitization to TNF-induced apoptosis by acute glutathione depletion in murine hepatocytes.	2003 Jun	12774022
Effect of acrolein and glutathione depleting agents on thioredoxin.	2004 Nov 15	15388247
Spatial activities and induction of glutamate-cysteine ligase (GCL) in the postimplantation rat embryo and visceral yolk sac.	2004 Oct	15115889
Increased expression of the MGMT repair protein mediated by cysteine prodrugs and chemopreventative natural products in human lymphocytes and tumor cell lines.	2007 Feb	16950796
Peroxiredoxin 2 and peroxidase enzymatic activity of mammalian spermatozoa.	2009 Jun	19208552
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	20541004
Nrf2 regulates ferroportin 1-mediated iron efflux and counteracts lipopolysaccharide-induced ferroportin 1 mRNA suppression in macrophages.	2011 Apr 1	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 Jan 14	21105742
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	22023385
Hepatic transcriptome and proteome responses against diethyl maleate-induced glutathione depletion in the rat.	2011 Sep	21161181
Isoeugenol destabilizes IL-8 mRNA expression in THP-1 cells through induction of the negative regulator of mRNA stability tristetraprolin.	2012 Feb	21969073
The ToxTracker assay: novel GFP reporter systems that provide mechanistic insight into the genotoxic properties of chemicals.	2012 Jan	22003191

Patents

Substance Class	Chemical Created by `admin` on `Sat Dec 16 03:27:59 GMT 2023` Edited by `admin` on `Sat Dec 16 03:27:59 GMT 2023`
Record UNII	G81WQB56OL
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DIETHYL MALEATE

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