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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

Maleic acid monosodium salt. Used in water soluble polymers preparation.

Approval Year

TargetsConditions

Conditions

PubMed

PubMed

TitleDatePubMed
Microperfusion study of proximal tubule bicarbonate transport in maleic acid-induced renal tubular acidosis.
1986 Mar
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
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
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
The comparison of plasma deproteinization methods for the detection of low-molecular-weight metabolites by (1)H nuclear magnetic resonance spectroscopy.
2002 May 15
Aqueous humour flow after a single oral dose of isosorbide-5-mononitrate in healthy volunteers.
2003 Aug
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
Patents

Sample Use Guides

In Vivo Use Guide
in cow: The aim of this study was to determine the influence of fumaric acid (FA) on ruminal fermentation and its effects on the acid-base balance of seven ruminally and duodenally fistulated multiparous German Holstein cows. The experiment was conducted in a change-over design with three periods in which the animals were randomly arranged in one of three treatments: Control (C; without FA), 300 or 600 g FA per day. The diets consisted of 7.4 kg DM grass silage, 4.2 kg concentrate mixture and 0, 300 or 600 g FA or wheat starch as isocaloric compensation per day and cow. FA supplementation decreased the rumen pH, acetic acid and butyric acid and increased propionic acid in rumen fluid. The results of the single-strand conformation polymorphism analysis (SSCP) did not show an influence of FA on the microbial population in the rumen
Route of Administration: Oral
In Vitro Use Guide
It was evaluated the effects of fumaric acid (FA) on tyrosinase activity and structure via enzyme kinetics and computational simulations. FA was found to be a reversible inhibitor of tyrosinase and its induced mechanism was the parabolic non-competitive inhibition type with IC50=13.7±0.25mM and Kislope=12.64±0.75mM. Kinetic measurements and spectrofluorimetry studies showed that FA induced regional changes in the active site of tyrosinase. One possible binding site for FA was identified under the condition without L-DOPA. The computational docking simulations further revealed that FA can interact with HIS263 and HIS85 at the active site. Furthermore, four important hydrogen bonds were found to be involved with the docking of FA on tyrosinase. By inhibiting tyrosinase and its central role in pigment production, FA is a potential natural antipigmentation agent.
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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