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Details

Stereochemistry ACHIRAL
Molecular Formula C4H4O4
Molecular Weight 116.0722
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of MALEIC ACID

SMILES

OC(=O)\C=C/C(O)=O

InChI

InChIKey=VZCYOOQTPOCHFL-UPHRSURJSA-N
InChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1-

HIDE SMILES / InChI

Molecular Formula C4H4O4
Molecular Weight 116.0722
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description

Fumaric acid (FA), naturally found in organisms, is a well-known intermediate of the citric acid cycle. Fumaric acid has been identified as an oncometabolite or an endogenous, cancer causing metabolite. High levels of this organic acid can be found in tumors or biofluids surrounding tumors. The major regulator of the response to hypoxia is the HIF transcription factor (HIF-alpha). Under normal oxygen levels, protein levels of HIF-alpha are very low due to constant degradation, mediated by a series of post-translational modification events catalyzed by the prolyl hydroxylase domain-containing enzymes PHD1, 2 and 3, (also known as EglN2, 1 and 3). Oncogenic action of fumarate appears to due to its ability to inhibit prolyl hydroxylase-containing enzymes.

Approval Year

TargetsConditions

Conditions

PubMed

PubMed

TitleDatePubMed
The influence of long-term treatment with timolol on human tear lysozyme albumin content.
1982
Urinary loss of glucose, phosphate, and protein by diffusion into proximal straight tubules injured by D-serine and maleic acid.
1985 Jun
Microperfusion study of proximal tubule bicarbonate transport in maleic acid-induced renal tubular acidosis.
1986 Mar
Do contrast media aggravate Fanconi's syndrome in rats? A comparison of diatrizoate, iohexol, and ioxilan.
1988 Sep
Menstrual migraine and intermittent ergonovine therapy.
1989 Jun
Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease.
1991 Jan 2
Antifungal activity of fumaric acid in mice infected with Candida albicans.
1991 Nov
Ocular surface alteration after long-term treatment with an antiglaucomatous drug.
1992 Jul
Physiology and pathophysiology of organic acids in cerebrospinal fluid.
1993
Disposition of [14C]velnacrine maleate in rats, dogs, and humans.
1993 Nov-Dec
Age-related reference values for urinary organic acids in a healthy Turkish pediatric population.
1994 Jun
[Studies on the mechanisms of renal damages induced by nephrotoxic compounds].
1995 Dec
Efficacy of 101 antimicrobials and other agents on the development of Cryptosporidium parvum in vitro.
1996 Dec
Glycine attenuates Fanconi syndrome induced by maleate or ifosfamide in rats.
1996 Mar
Morphological effect of the type, concentration and etching time of acid solutions on enamel and dentin surfaces.
1998
A synthetic polycation, a copolymer of 1-vinyl-3-methylimidazole iodide with maleic acid diethyl ester, increases passive ionic permeability in erythrocyte membranes modified by fatty acids.
1998
Abnormal substrate levels that depend upon mitochondrial function in cerebrospinal fluid from Alzheimer patients.
1998
Hepatic infarction following percutaneous ethanol injection therapy for hepatocellular carcinoma.
1998 Nov
In vitro shear bond strength of adhesive to normal and fluoridated enamel under various contaminated conditions.
1999 Aug
Experience with intraarterial infusion of styrene maleic acid neocarzinostatin (SMANCS)-lipiodol in pancreatic cancer.
1999 Jul-Aug
Determination of trimebutine and desmethyl-trimebutine in human plasma by HPLC.
2000 Jul
Subcritical mineralization of sodium salt of dodecyl benzene sulfonate using sonication-wet oxidation (SONIWO) technique.
2001 Jun
Molecular mechanism for the regulation of human mitochondrial NAD(P)+-dependent malic enzyme by ATP and fumarate.
2002 Jul
An in vitro study on restoring bond strength of a GIC to saliva contaminated enamel under unrinse condition.
2002 Jul-Aug
The comparison of plasma deproteinization methods for the detection of low-molecular-weight metabolites by (1)H nuclear magnetic resonance spectroscopy.
2002 May 15
Neocortical neurons cultured from mice with expanded CAG repeats in the huntingtin gene: unaltered vulnerability to excitotoxins and other insults.
2003
Aqueous humour flow after a single oral dose of isosorbide-5-mononitrate in healthy volunteers.
2003 Aug
Molecular machinery for non-vesicular trafficking of ceramide.
2003 Dec 18
Dynamic alterations of fibronectin layers on copolymer substrates with graded physicochemical characteristics.
2004 Mar 30
Determination of ergometrine maleate by fluorescence detection.
2005 May-Jun
Tumor-necrosis-factor-related apoptosis-inducing-ligand (TRAIL)-mediated death of neurons in living human brain tissue is inhibited by flupirtine-maleate.
2005 Oct
Protein adsorption from flowing solutions on pure and maleic acid copolymer modified glass particles.
2006 Aug 1
Effects of antiglaucoma drugs on collagen gel contraction mediated by human corneal fibroblasts.
2006 Jun
Probing carboxylate Gibbs transfer energies via liquid|liquid transfer at triple phase boundary electrodes: ion-transfer voltammetry versus COSMO-RS predictions.
2008 Jul 14
Quantitative morphometry of respiratory tract epithelial cells as a tool for testing chemopreventive agent efficacy.
2010 Mar
Integration of metabolomics and transcriptomics data to aid biomarker discovery in type 2 diabetes.
2010 May
Fumaric acid attenuates the eotaxin-1 expression in TNF-α-stimulated fibroblasts by suppressing p38 MAPK-dependent NF-κB signaling.
2013 Aug
Evaluation of aggregating brain cell cultures for the detection of acute organ-specific toxicity.
2013 Jun
Curcumin prevents maleate-induced nephrotoxicity: relation to hemodynamic alterations, oxidative stress, mitochondrial oxygen consumption and activity of respiratory complex I.
2014 Nov
Patents

Sample Use Guides

In Vivo Use Guide
Rats: intravenous administration of 200 mg/kg maleic acid
Route of Administration: Intravenous
In Vitro Use Guide
The effects of 6 M maleic acid on transport processes differ for amino acids and sugars and become manifest at distinct points during development.
Substance Class Chemical
Created
by admin
on Mon Oct 21 22:21:52 UTC 2019
Edited
by admin
on Mon Oct 21 22:21:52 UTC 2019
Record UNII
91XW058U2C
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MALEIC ACID
EP   HSDB   II   INCI   MART.   MI   USP-RS   WHO-DD  
INCI  
Official Name English
MALEIC ACID [MART.]
Common Name English
MALEIC ACID [MI]
Common Name English
MALEIC ACID [INCI]
Common Name English
MALEIC ACID [EP]
Common Name English
MALEIC ACID [HSDB]
Common Name English
NSC-25940
Code English
(Z)-BUTENEDIOIC ACID
Systematic Name English
MALEIC ACID [II]
Common Name English
MALEIC ACID [USP-RS]
Common Name English
MALEIC ACID [WHO-DD]
Common Name English
CIS-BUTENEDIOIC ACID
Systematic Name English
MALEIC ACID [USP]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C718
Created by admin on Mon Oct 21 22:21:52 UTC 2019 , Edited by admin on Mon Oct 21 22:21:52 UTC 2019
Code System Code Type Description
ECHA (EC/EINECS)
203-742-5
Created by admin on Mon Oct 21 22:21:52 UTC 2019 , Edited by admin on Mon Oct 21 22:21:52 UTC 2019
PRIMARY
RXCUI
1426330
Created by admin on Mon Oct 21 22:21:52 UTC 2019 , Edited by admin on Mon Oct 21 22:21:52 UTC 2019
PRIMARY RxNorm
EVMPD
SUB12134MIG
Created by admin on Mon Oct 21 22:21:52 UTC 2019 , Edited by admin on Mon Oct 21 22:21:52 UTC 2019
PRIMARY
PUBCHEM
444266
Created by admin on Mon Oct 21 22:21:52 UTC 2019 , Edited by admin on Mon Oct 21 22:21:52 UTC 2019
PRIMARY
MERCK INDEX
M7037
Created by admin on Mon Oct 21 22:21:52 UTC 2019 , Edited by admin on Mon Oct 21 22:21:52 UTC 2019
PRIMARY Merck Index
RXCUI
1426331
Created by admin on Mon Oct 21 22:21:52 UTC 2019 , Edited by admin on Mon Oct 21 22:21:52 UTC 2019
PRIMARY
NCI_THESAURUS
C25951
Created by admin on Mon Oct 21 22:21:52 UTC 2019 , Edited by admin on Mon Oct 21 22:21:52 UTC 2019
PRIMARY
CAS
110-16-7
Created by admin on Mon Oct 21 22:21:52 UTC 2019 , Edited by admin on Mon Oct 21 22:21:52 UTC 2019
PRIMARY
HSDB
110-16-7
Created by admin on Mon Oct 21 22:21:52 UTC 2019 , Edited by admin on Mon Oct 21 22:21:52 UTC 2019
PRIMARY
MESH
C030272
Created by admin on Mon Oct 21 22:21:52 UTC 2019 , Edited by admin on Mon Oct 21 22:21:52 UTC 2019
PRIMARY
EPA CompTox
110-16-7
Created by admin on Mon Oct 21 22:21:52 UTC 2019 , Edited by admin on Mon Oct 21 22:21:52 UTC 2019
PRIMARY
WIKIPEDIA
MALEIC ACID
Created by admin on Mon Oct 21 22:21:52 UTC 2019 , Edited by admin on Mon Oct 21 22:21:52 UTC 2019
PRIMARY
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