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Maleic acid

Alias: Maleic acid Kyselina maleinova 2-Butenedioic acidcis-Butenedioic acid
Cat No.:V10128 Purity: ≥98%
Maleic Acid inhibits glutamate decarboxylase (GAD) in Escherichia coli (E.
Maleic acid
Maleic acid Chemical Structure CAS No.: 110-16-7
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
5g
Other Sizes

Other Forms of Maleic acid:

  • Maleic Acid-d2 (Maleic-2,3-d2 acid)
Official Supplier of:
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Top Publications Citing lnvivochem Products
Product Description
Maleic Acid inhibits glutamate decarboxylase (GAD) in Escherichia coli (E. coli) and Listeria (L. monocytogenes).
Biological Activity I Assay Protocols (From Reference)
ln Vitro
WT 10403S has MICs of 34 mM, 25 mM, 31 mM, and 30 mM against acids (such maleic acid), which translate to pre-growth pH values of 4.84, 5.14, 5.32, and 5.02, in that order. Maleic acid, which functions at a lower pH (4.84), exhibited the least inhibitory effect of all the chemicals examined. At pH 3, 8.6 mM and 4.3 mM of each organic acid were given to the strains that were the least acid-tolerant (EGD-e) and the most acid-tolerant (10403S), respectively. Maleic acid had the greatest bactericidal effect on these two strains [2].
References

[1]. Glutamate decarboxylase. Substrate specificity and inhibition by carboxylic acids. Biochemistry. 1972 Mar 28;11(7):1304-9.

[2]. A novel approach in acidic disinfection through inhibition of acid resistance mechanisms; Maleic acid-mediated inhibition of glutamate decarboxylase activity enhances acid sensitivity of Listeria monocytogenes. Food Microbiol. 2018 Feb;69:96-104.

Additional Infomation
Maleic acid is a colorless crystalline solid having a faint odor. It is combustible though it may take some effort to ignite. It is soluble in water. It is used to make other chemicals and for dyeing and finishing naturally occurring fibers.
Maleic acid is a butenedioic acid in which the double bond has cis- (Z)-configuration. It has a role as a plant metabolite, an algal metabolite and a mouse metabolite. It is a conjugate acid of a maleate(1-) and a maleate.
Maleic acid has been reported in Populus tremula, Psychotria punctata, and other organisms with data available.
Maleic Acid is an organic salt or ester of maleic acid that could be conjugated to free base compounds/drugs to improve the physiochemical properties including stability, solubility and dissolution rate. (NCI)
Maleic acid is an industrial raw material for the production of glyoxylic acid by ozonolysis. Maleic acid is an organic compound which is a dicarboxylic acid (molecule with two carboxyl groups). The molecule consists of an ethylene group flanked by two carboxylic acid groups. Maleic acid is the cis isomer of butenedioic acid, whereas fumaric acid is the trans isomer. The cis isomer is the less stable one of the two; the difference in heat of combustion is 22.7 kJ/mol. The physical properties of maleic acid are very different from that of fumaric acid. Maleic acid is soluble in water whereas fumaric acid is not and the melting point of maleic acid (130 - 131 degree centigrade) is also much lower than that of fumaric acid (287 degree centigrade). Both properties of maleic acid can be explained on account of the intramolecular hydrogen bonding that takes place at the expense of intermolecular interactions. Maleic acid is converted into maleic anhydride by dehydration, to malic acid by hydration, and to succinic acid by hydrogenation. It reacts with thionyl chloride or phosphorus pentachloride to give the maleic acid chloride (it is not possible to isolate the mono acid chloride). Maleic acid is a reactant in many Diels-Alder reactions.
See also: Surfomer (monomer of); Ferropolimaler (monomer of) ... View More ...
Mechanism of Action
Kidney damage has been observed as a systemic toxic action of maleic acid. Morphological-functional changes in the kidneys were produced by intraperitoneal injection (100-350 mg/kg; rats, dogs) and also by inhalation exposure to ca. 720 mg/mc (rats). The damage to distal and proximal tubular resorption produced by maleic acid is reminiscent of the known (congenital or acquired) Fanconi syndrome in humans. This damage seems to be caused by the interaction of maleic acid with glutathione in tubular renal cells, leading to intolerable concentration of free radicals and peroxides. In addition to the resultant cellular damage, maleic acid appears to affect Na+ and H+ ion transport in the proximal tubes [RE5]. After chronic exposure of male rats (250, 500, 750 mg/kg /per/ day for up to two years), an increased mortality as well as kidney damage and delayed growth was observed in all dosage groups. Liver and testicular damage has also been found in highest dosage group. No signs of carcinogenic activity of maleic acid were discovered with long-term dosage, which however was not designed as a carcinogenicity study.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C4H4O4
Molecular Weight
116.07
Exact Mass
116.01
CAS #
110-16-7
Related CAS #
Maleic Acid-d2;24461-33-4
PubChem CID
444266
Appearance
Monoclinic prisms from water
White crystals from water, alcohol and benzene
Colorless crystals
Density
1.5±0.1 g/cm3
Boiling Point
355.5±25.0 °C at 760 mmHg
Melting Point
134-138ºC
Flash Point
183.0±19.7 °C
Vapour Pressure
0.0±1.7 mmHg at 25°C
Index of Refraction
1.526
LogP
-0.01
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
2
Heavy Atom Count
8
Complexity
119
Defined Atom Stereocenter Count
0
SMILES
O([H])C(/C(/[H])=C(/[H])\C(=O)O[H])=O
InChi Key
VZCYOOQTPOCHFL-UPHRSURJSA-N
InChi Code
InChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1-
Chemical Name
2-Butenedioic acid (2Z)-
Synonyms
Maleic acid Kyselina maleinova 2-Butenedioic acidcis-Butenedioic acid
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
H2O : ~100 mg/mL (~861.55 mM)
Solubility (In Vivo)
Solubility in Formulation 1: 100 mg/mL (861.55 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 8.6155 mL 43.0775 mL 86.1549 mL
5 mM 1.7231 mL 8.6155 mL 17.2310 mL
10 mM 0.8615 mL 4.3077 mL 8.6155 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

Calculator

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

Clinical Trial Information
NCT Number Recruitment interventions Conditions Sponsor/Collaborators Start Date Phases
NCT04293081 Completed Drug: Preemptive chlorepheniramine
maleate intravenous injection
Agitated; State, Acute Reaction to
Stress
Ain Shams University January 16, 2019 Not Applicable
NCT03667131 Completed Drug: Enalapril Maleate
Drug: Placebo
Rheumatoid Arthritis University of Guadalajara February 13, 2017 Phase 2
NCT04486911 Active, not recruiting Drug: Pyrotinib maleate, SHR6390,
letrozole
Breast Cancer Shengjing Hospital July 27, 2020 Phase 2
NCT05228951 Recruiting Drug: Pyrotinib maleate, dalpiciclib,
Trastuzumab, letrozole
Breast Cancer Shengjing Hospital February 10, 2022 Phase 2
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