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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.
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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 with a slight odor. It is flammable, but requires some effort to ignite. It is soluble in water. It is used in the manufacture of other chemicals and in the dyeing and finishing of natural fibers. Maleic acid is a butenedioic acid with a cis (Z) configuration of its double bonds. It is a plant metabolite, an algal metabolite, and a mouse metabolite. It is the conjugate acid of maleate (1-) and maleate. Maleic acid has been reported to be found in European aspen (Populus tremula), spotted madder (Psychotria punctata), and several other organisms with relevant data. Maleic acid is an organic salt or ester of maleic acid that can be combined with free base compounds/drugs to improve its physicochemical properties, including stability, solubility, and dissolution rate. (NCI) Maleic acid is an industrial feedstock for the ozone decomposition process to produce glyoxylic acid. Maleic acid is an organic compound belonging to the dicarboxylic acid family (containing two carboxyl groups in the molecule). The molecule consists of one vinyl group and two carboxyl groups. Maleic acid is the cis isomer of butenic acid, while fumaric acid is its trans isomer. The cis isomer is less stable, and their heats of combustion differ by 22.7 kJ/mol. The physical properties of maleic acid are drastically different from those of fumaric acid. Maleic acid is soluble in water, while fumaric acid is insoluble; the melting point of maleic acid (130-131°C) is also much lower than that of fumaric acid (287°C). These properties of maleic acid can be attributed to the formation of intramolecular hydrogen bonds, which weaken intermolecular interactions. Maleic acid undergoes dehydration to produce maleic anhydride, hydration to produce malic acid, and hydrogenation to produce succinic acid. It reacts with thionyl chloride or phosphorus pentachloride to produce maleyl chloride (which cannot be isolated to obtain monoacyl chloride). Maleic acid is a reactant in many Diels-Alder reactions. See also: Surfactants (monomers); Iron polymers (monomers)... See more...
Mechanism of Action
Systemic toxicity of maleic acid has been observed to cause kidney damage. Intraperitoneal injection (100–350 mg/kg; rats, dogs) and inhalation of approximately 720 mg/mc (rat) both caused morphological and functional changes in the kidneys. Damage to distal and proximal tubular reabsorption caused by maleic acid is similar to known (congenital or acquired) Fanconi syndrome in humans. This damage appears to be caused by the interaction of maleic acid with glutathione in renal tubular cells, leading to excessive concentrations of free radicals and peroxides. In addition to the resulting cellular damage, maleic acid appears to affect Na+ and H+ ion transport in the proximal tubules [RE5]. In male rats, prolonged exposure to maleic acid (250, 500, 750 mg/kg/day for up to two years) resulted in increased mortality, kidney damage, and growth retardation in all dose groups. Liver and testicular damage were also observed in the highest dose group. No carcinogenic activity of maleic acid was found with long-term administration, but this study was not intended to conduct 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:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
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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:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • 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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