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
SMILES
CCOC(=O)\C=C\C(=O)OCC
InChI
InChIKey=IEPRKVQEAMIZSS-AATRIKPKSA-N
InChI=1S/C8H12O4/c1-3-11-7(9)5-6-8(10)12-4-2/h5-6H,3-4H2,1-2H3/b6-5+
| 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 |
|
| Lipid peroxidation: a possible mechanism of cephaloridine-induced nephrotoxicity. | 1983 Jan |
|
| Paradoxical effects of perturbation of intracellular levels of glutathione on halothane-induced hepatotoxicity in hyperthyroid rats. | 1984 Apr |
|
| Cytotoxicity of halogenated alkanes in primary cultures of rat hepatocytes from normal, partial hepatectomized, and preneoplastic/neoplastic liver. | 1985 Sep 15 |
|
| The radiosensitizing effects of misonidazole (MISO) in combination with diethyl maleate (DEM) in mouse mammary tumors. | 1986 Oct |
|
| Detoxifying activities in alveolar macrophages of rats treated with acetylcysteine, diethyl maleate and/or aroclor. | 1986 Sep-Oct |
|
| Regulation of hepatic nitric oxide synthase by reactive oxygen intermediates and glutathione. | 1995 Feb 1 |
|
| Thiol modulation of TNF alpha and IL-1 induced MnSOD gene expression and activation of NF-kappa B. | 1995 Jul 5 |
|
| Expression of inducible nitric oxide synthase in endotoxemic rat hepatocytes is dependent on the cellular glutathione status. | 1999 Feb |
|
| Glutathione depletion induces apoptosis of rat hepatocytes through activation of protein kinase C novel isoforms and dependent increase in AP-1 nuclear binding. | 2000 Dec 15 |
|
| Electrophile response element-mediated induction of the cystine/glutamate exchange transporter gene expression. | 2002 Nov 22 |
|
| Mechanisms for sensitization to TNF-induced apoptosis by acute glutathione depletion in murine hepatocytes. | 2003 Jun |
|
| Effect of acrolein and glutathione depleting agents on thioredoxin. | 2004 Nov 15 |
|
| Spatial activities and induction of glutamate-cysteine ligase (GCL) in the postimplantation rat embryo and visceral yolk sac. | 2004 Oct |
|
| Transcriptional regulation of thioredoxin reductase 1 expression by cadmium in vascular endothelial cells: role of NF-E2-related factor-2. | 2005 Jun |
|
| Increased expression of the MGMT repair protein mediated by cysteine prodrugs and chemopreventative natural products in human lymphocytes and tumor cell lines. | 2007 Feb |
|
| The dietary antioxidant resveratrol affects redox changes of PPARalpha activity. | 2007 May |
|
| Tumor necrosis factor-associated protein 1 (TRAP-1) protects cells from oxidative stress and apoptosis. | 2007 Nov |
|
| The effect of insecticide synergists on the response of scabies mites to pyrethroid acaricides. | 2009 |
|
| 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 |
|
| Dual mechanisms of NF-kappaB inhibition in carnosol-treated endothelial cells. | 2010 May 15 |
|
| Regulation of human carbonyl reductase 3 (CBR3; SDR21C2) expression by Nrf2 in cultured cancer cells. | 2010 Oct 5 |
|
| 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 |
|
| A new in vitro method for identifying chemical sensitizers combining peptide binding with ARE/EpRE-mediated gene expression in human skin cells. | 2010 Sep |
|
| Protein thiol oxidation in murine airway epithelial cells in response to naphthalene or diethyl maleate. | 2010 Sep |
|
| Nrf2 regulates ferroportin 1-mediated iron efflux and counteracts lipopolysaccharide-induced ferroportin 1 mRNA suppression in macrophages. | 2011 Apr 1 |
|
| 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 |
|
| Isoeugenol destabilizes IL-8 mRNA expression in THP-1 cells through induction of the negative regulator of mRNA stability tristetraprolin. | 2012 Feb |
|
| 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 |
|
| NCTC 2544 and IL-18 production: a tool for the identification of contact allergens. | 2013 Apr |
|
| Role of PKC-β in chemical allergen-induced CD86 expression and IL-8 release in THP-1 cells. | 2014 Feb |
|
| A novel toxicogenomics-based approach to categorize (non-)genotoxic carcinogens. | 2015 Dec |
|
| Genes specifically modulated in sensitized skins allow the detection of sensitizers in a reconstructed human skin model. Development of the SENS-IS assay. | 2015 Jun |
Patents
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 17:39:35 GMT 2023
by
admin
on
Fri Dec 15 17:39:35 GMT 2023
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| Record UNII |
5WBU5A3E8A
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| Record Status |
Validated (UNII)
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| Record Version |
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638144
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623-91-6
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5722
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5WBU5A3E8A
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20954
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C035088
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210-819-7
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DTXSID7027253
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