CopyCopied, VZCYOOQTPOCHFL-UPHRSURJSA-N
Maleic acid and fumaric acid do not spontaneously interconvert because rotation around a carbon carbon double bond is not energetically favourable.
Both properties of maleic acid can be explained on account of the intramolecular hydrogen bonding[5] that takes place in maleic acid at the expense of intermolecular interactions, and that are not possible in fumaric acid for geometric reasons. Maleic acid, being electrophilic, participates as a dienophile in many Diels-Alder reactions. [4], 22.7 kJ/mol higher than that of fumaric acid.
Again, the large difference in water solubility makes fumaric acid purification easy. Incompatible with strong oxidizingagents, bases. [8] Light converts elemental bromine into a bromine radical, which attacks the alkene in a radical addition reaction to a bromo-alkane radical; and now single bond rotation is possible. Its chemical formula is HO2CCH=CHCO2H. Kurt Lohbeck, Herbert Haferkorn, Werner Fuhrmann and Norbert Fedtke "Maleic and Fumaric Acids" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2000. However, conversion of the cis isomer into the trans isomer is possible by photolysis in the presence of a small amount of bromine. Molecular Formula: C 4 H 4 O 4. The melting point of maleic acid (135 °C) is also much lower than that of fumaric acid (287 °C). Molecular Weight: 116.073 g/mol. This enzyme catalyses isomerization between fumarate and maleate. A butenedioic acid in which the double bond has cis- (Z)-configuration. Maleic acid is the cis-isomer of butenedioic acid, whereas fumaric acid is the trans-isomer. In industry, maleic acid is derived by hydrolysis of maleic anhydride, the latter being produced by oxidation of benzene or butane. Get … carfenazine, chlorpheniramine, pyrilamine, methylergonovine, and thiethylperazine.
In another method (used as a classroom demonstration), maleic acid is transformed into fumaric acid through the process of heating the maleic acid in hydrochloric acid solution. Cas Number: 110-16-7.
EINECS Number: 203-742-5. MDL Number: MFCD00002700. This conversion, an isomerization, is catalysed by a variety of reagents, such as mineral acids and thiourea.
Combustible. Some bacteria produce the enzyme maleate isomerase, which is used by bacteria in nicotinate metabolism. ; CRC Press: Boca Raton, Florida., 1993. Maleic acid is more soluble in water than fumaric acid. Many drugs that contain amines are provided as the maleate acid salt, e.g. CopyCopied, InChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1-
ORL-RAT LD50 708 mg kg-1, ORL-MUS LD50 2400 mg kg-1, P261-P280-P305+P351+P338-P304+P340-P405-P501a, WARNING: Irritates skin and eyes, harmful if swallowed. The isomerization is a popular topic in schools. The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals, Institute for Occupational Safety and Health, Maleic Anhydride, Maleic Acid, and Fumaric Acid, "A Refinement of the Crystal Structure of Maleic Acid", Calculator: Water and solute activities in aqueous maleic acid, https://en.wikipedia.org/w/index.php?title=Maleic_acid&oldid=952583370, Pages using collapsible list with both background and text-align in titlestyle, Articles containing unverified chemical infoboxes, Creative Commons Attribution-ShareAlike License, This page was last edited on 23 April 2020, at 00:37. Maleic acid. Maleic acid has a heat of combustion of -1,355 kJ/mol. Maleic acid esters are also called maleates, for instance dimethyl maleate.
Its chemical formula is HO2CCH=CHCO2H.
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Although not practised commercially, maleic acid can be converted into maleic anhydride by dehydration, to malic acid by hydration, and to succinic acid by hydrogenation (ethanol / palladium on carbon).
COVID-19 is an emerging, rapidly evolving situation. Reversible addition (of H+) leads to free rotation about the central C-C bond and formation of the more stable and less soluble fumaric acid. The bromine radicals recombine and fumaric acid is formed. C(=C\C(=O)O)\C(=O)O
N,N,2,2-tetramethyl-1-propanamine (10076-31-0), diethyl 4-methoxybenzoylphosphonate (16703-95-0), 1-fluoro-4-(2,3,3-trichloro-1-cyclopropen-1-yl)benzene, chloromethylsulfanyl-cyclohexane (68483-71-6), 1-methyl-8-phenyl-3,9-dihydro-1H-purine-2,6-dione (2850-37-5), 6-bromo-3,3-dimethyl-2,3,7,8-tetrahydrocyclopenta[ij]isoquinoline, 8-methoxy-8-methylbicyclo[4.2.0]octan-2-one, 7,9,9-trimethyl-2-oxabicyclo[5.2.0]nonan-3-one, 1a,9b-dihydrophenanthro[9,10-b]oxirene (585-08-0), (5Z)-3-acetyl-5-(benzylsulfanylmethylidene)-4-hydroxypyrrol-2-one (731-57-7), N-(5-oxo-4,5-dihydro[1,2]dithiolo[4,3-b]pyrrol-6-yl)acetamide (488-04-0), 3-hydroxy-2,4,6-cycloheptatrien-1-one (3324-76-3), 3-hydroxy-1,1,4,4-tetramethyl-tetralin-2-one, 1,1,5,5-tetramethyl-1,5-dihydro-3-benzoxepine-2,4-dione, Journal of the American Chemical Society, 86, p. 4603, 1964. Maleic acid is the cis-isomer of butenedioic acid, whereas fumaric acid is the trans-isomer. CopyCopied, CSID:392248, http://www.chemspider.com/Chemical-Structure.392248.html (accessed 11:24, Nov 12, 2020)
InChIKey: VZCYOOQTPOCHFL-KHGLRPAFDO. Maleic acid may be used to form acid addition salts with drugs to make them more stable, such as indacaterol maleate. InChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1-, InChI=1/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1-, Except where otherwise noted, data are given for materials in their, CRC Handbook of Chemistry and Physics, 73rd ed. Molecular Formula C 4 H 4 O 4; Average mass 116.072 Da; Monoisotopic mass 116.010956 Da; ChemSpider ID 392248 The maleate ion is useful in biochemistry as an inhibitor of transaminase reactions.
The maleate ion is the ionized form of maleic acid. [6], Maleic acid is an industrial raw material for the production of glyoxylic acid by ozonolysis.[7]. Stable. It is mainly used as a precursor to fumaric acid, and relative to its parent maleic anhydride, maleic acid has few applications.
[9] It reacts with thionyl chloride or phosphorus pentachloride to give the maleic acid chloride (it is not possible to isolate the mono acid chloride). Smiles: OC (=O)\C=C\C (O)=O. It is mainly used as a precursor to fumaric acid, and relative to its parent maleic anhydride, maleic acid has few applications.
Maleic acid or cis-butenedioic acid is an organic compound that is a dicarboxylic acid, a molecule with two carboxyl groups. A butenedioic acid in which the double bond has cis- (Z)-configuration. Maleic acid | C4H4O4 | CID 444266 - structure, chemical names, physical and chemical properties, classification, patents, literature, biological activities, safety/hazards/toxicity information, supplier lists, and more. Maleic acid is also used as an adhesion promoter for different substrates, such as nylon and zinc coated metals e.g galvanized steel, in methyl methacrylate based adhesives. The major industrial use of maleic acid is its conversion to fumaric acid. Maleic acid or cis-butenedioic acid is an organic compound that is a dicarboxylic acid, a molecule with two carboxyl groups.