It may be present in fermented alcoholic beverages such as beer and wine. Malonic acid reacts as a typical carboxylic acid: forming amide, ester, anhydride, and chloride derivatives. [14], Carbon suboxide is prepared by warming a dry mixture of phosphorus pentoxide (P4O10) and malonic acid. [20], In food and drug applications, malonic acid can be used to control acidity, either as an excipient in pharmaceutical formulation or natural preservative additive for foods.[3]. Malonyl CoA is formed from acetyl CoA by the action of acetyl-CoA carboxylase, and the malonate is transferred to an acyl carrier protein to be added to a fatty acid chain. It is a useful precursor to various drugs. IDENTIFICATION: Maleic acid is a colorless, crystalline solid with a faint acidic odor and a strong astringent taste. 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. [13], Thus, for example, the reaction product of acrolein and malonic acid in pyridine is trans-2,4-Pentadienoic acid with one carboxylic acid group and not two. It is mainly used as a precursor to fumaric acid, and relative to its parent maleic anhydride, maleic acid has few applications. Maleic acid is more soluble in water than fumaric acid. 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. It is very soluble in water. In 2004, annual global production of malonic acid and related diesters was over 20,000 metric tons. Malonic acid[2] is a naturally occurring substance found in many fruits and vegetables. Malonic acid (IUPAC systematic name: propanedioic acid) is a dicarboxylic acid with structure CH2(COOH)2.
IDENTIFICATION: Malonic acid, which is also called propanedioic acid, is a colorless or white crystalline powder. It occurs naturally in the air, and occurs because of engine emissions, wood fires and from cigarettes. PCT/US2013/029441 2012. Äpfelsäure (2-Hydroxybernsteinsäure, seltener auch Apfelsäure) ist eine chemische Verbindung aus den Gruppen der Dicarbonsäuren und Hydroxycarbonsäuren, die als rechtsdrehende D- und als linksdrehende L-Äpfelsäure vorkommt.
14/418,940. Malonate or propanedioate compounds include salts and esters of malonic acid, such as, Carboxylic acid with chemical formula CH2(COOH)2, InChI=1S/C3H4O4/c4-2(5)1-3(6)7/h1H2,(H,4,5)(H,6,7), InChI=1/C3H4O4/c4-2(5)1-3(6)7/h1H2,(H,4,5)(H,6,7), Except where otherwise noted, data are given for materials in their. Malonic acid is used as a building block chemical to produce numerous valuable compounds,[21] including the flavor and fragrance compounds gamma-nonalactone, cinnamic acid, and the pharmaceutical compound valproate. [29], Malonic acid is diprotic; that is, it can donate two protons per molecule. The name originates from the Greek word μᾶλον (malon) meaning 'apple'. Ullmann's Encyclopedia of Industrial Chemistry. 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. This conversion, an isomerization, is catalysed by a variety of reagents, such as mineral acids and thiourea. [17] The global coatings market for automobiles was estimated to be $18.59 billion in 2014 with projected combined annual growth rate of 5.1% through 2022.[18]. 2013 US. K−1 bestimmt.
[11] Diese Eigenschaft wird beispielsweise im Tiermodell Farbratte genutzt, um die Symptome des De-Toni-Fanconi-Syndroms hervorzurufen. One application of malonic acid is in the coatings industry as a crosslinker for low-temperature cure powder coatings, which are becoming increasingly valuable for heat sensitive substrates and a desire to speed up the coatings process.
2004 International Waterborne, High-Solids, and Powder Coatings Symposium. Some bacteria produce the enzyme maleate isomerase, which is used by bacteria in nicotinate metabolism. It has a sour taste. Ihre Salze heißen Male(in)ate. [5], The structure has been determined by X-ray crystallography[6] and extensive property data including for condensed phase thermochemistry are available from the National Institute of Standards and Technology. Bei längerem Erhitzen auf 150 °C sowie bei UV-Bestrahlung isomerisiert die Maleinsäure zur stabileren Fumarsäure. Maleic acid and fumaric acid do not spontaneously interconvert because rotation around a carbon carbon double bond is not energetically favourable.
The maleate ion is the ionized form of maleic acid. In der Pharmakologie dienen Lösungen der Maleate von Antihistaminen als injizierbare Medikamente für den akuten Einsatz. Inhibition of this enzyme decreases cellular respiration. [26] It binds to the active site of the enzyme without reacting, competing with the usual substrate succinate but lacking the −CH2CH2− group required for dehydrogenation. [4], 22.7 kJ/mol higher than that of fumaric acid. [6], Maleic acid is an industrial raw material for the production of glyoxylic acid by ozonolysis.[7]. In der Natur ist L-Äpfelsäure meist in unreifen Früchten wie Äpfeln, Quitten, Weintrauben, Berberitzenbeeren, Vogelbeeren und Stachelbeeren, en… 3,591,676. [4], Malonic acid was first prepared in 1858 by the French chemist Victor Dessaignes via the oxidation of malic acid. [16], Malonic acid is a precursor to specialty polyesters. Diese Seite wurde zuletzt am 14.
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