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
Lipid peroxidation: a possible mechanism of cephaloridine-induced nephrotoxicity.	1983 Jan	6845359
Paradoxical effects of perturbation of intracellular levels of glutathione on halothane-induced hepatotoxicity in hyperthyroid rats.	1984 Apr	6724195
The radiosensitizing effects of misonidazole (MISO) in combination with diethyl maleate (DEM) in mouse mammary tumors.	1986 Oct	3759535
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
Hepatocellular response to chemical stress in CD-1 mice: induction of early genes and gamma-glutamylcysteine synthetase.	2000 Aug	10915739
Electrophile response element-mediated induction of the cystine/glutamate exchange transporter gene expression.	2002 Nov 22	12235164
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
The dietary antioxidant resveratrol affects redox changes of PPARalpha activity.	2007 May	17134953
Dissecting the signaling events that impact classical nuclear import and target nuclear transport factors.	2009 Dec 24	20041180
Dual mechanisms of NF-kappaB inhibition in carnosol-treated endothelial cells.	2010 May 15	20116392
Regulation of human carbonyl reductase 3 (CBR3; SDR21C2) expression by Nrf2 in cultured cancer cells.	2010 Oct 5	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 Sep	20541004
A new in vitro method for identifying chemical sensitizers combining peptide binding with ARE/EpRE-mediated gene expression in human skin cells.	2010 Sep	20491607
Nrf2 regulates ferroportin 1-mediated iron efflux and counteracts lipopolysaccharide-induced ferroportin 1 mRNA suppression in macrophages.	2011 Apr 1	21303654
An in vitro test to screen skin sensitizers using a stable THP-1-derived IL-8 reporter cell line, THP-G8.	2011 Dec	21920952
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

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