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Not to be confused with malic acid or maleic acid.
Malonic acid
Malonic acid
Malonic-acid-3D-balls.png
Identifiers
CAS number 141-82-2 YesY
PubChem 867
ChemSpider 844 YesY
DrugBank DB02175
ChEBI CHEBI:30794 YesY
ChEMBL CHEMBL7942 YesY
Jmol-3D images Image 1
Properties
Molecular formula C3H4O4
Molar mass 104.06 g mol−1
Density 1.619 g/cm3
Melting point 135–136 °C
Boiling point decomposes
Solubility in water Miscible
Acidity (pKa) pKa1 = 2.83[1]
pKa2 = 5.69[1]
Related compounds
Other anions malonate
Related carboxylic acids acetic acid
oxalic acid
propionic acid
tartronic acid
acrylic acid
butyric acid
succinic acid
fumaric acid
Related compounds propanone
propionaldehyde
propanedial
dimethyl malonate
Hazards
MSDS External MSDS
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY (verify) (what is: YesY/N?)
Infobox references

Malonic acid (IUPAC systematic name: propanedioic acid) is a dicarboxylic acid with structure CH2(COOH)2. The ionized form of malonic acid, as well as its esters and salts, are known as malonates. For example, diethyl malonate is malonic acid's diethyl ester. The name originates from the Greek word μᾶλον (malon) meaning 'apple'.

Biochemistry[edit]

The calcium salt of malonic acid occurs in high concentrations in beetroot. It exists in its normal state as white crystals. Malonic acid is the classic example of a competitive inhibitor: It acts against succinate dehydrogenase (complex II) in the respiratory electron transport chain.

Preparation[edit]

A classical preparation of malonic acid starts from chloroacetic acid:[2]

Preparation of malonic acid from chloroacetic acid.

Sodium carbonate generates the sodium salt, which is then reacted with sodium cyanide to provide the cyano acetic acid salt via a nucleophilic substitution. The nitrile group can be hydrolyzed with sodium hydroxide to sodium malonate, and acidification affords malonic acid.

Malonic acid was first prepared in 1858 by the French chemist Victor Dessaignes (1800-1885) via the oxidation of malic acid.[3]

Organic reactions[edit]

In a well-known reaction, malonic acid condenses with urea to form barbituric acid. Malonic acid is also frequently used as an enolate in Knoevenagel condensations or condensed with acetone to form Meldrum's acid. The esters of malonic acid are also used as a CH2COOH synthon in the malonic ester synthesis.

Additionally, the coenzyme A derivative of malonate, malonyl-CoA, is an important precursor in fatty acid biosynthesis along with acetyl CoA. 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.

References[edit]

  1. ^ a b pKa Data Compiled by R. Williams (pdf; 77 kB)
  2. ^ Nathan Weiner, Malonic acid, Org. Synth. ; Coll. Vol. 2: 376 
  3. ^ See:

External links[edit]


Original courtesy of Wikipedia: http://en.wikipedia.org/wiki/Malonic_acid — Please support Wikipedia.
This page uses Creative Commons Licensed content from Wikipedia. A portion of the proceeds from advertising on Digplanet goes to supporting Wikipedia.

33 news items

 
DigitalJournal.com
Fri, 24 Oct 2014 00:30:00 -0700

Market Research Report on Global and Chinese Malonic Acid Industry, 2009-2019 is a professional and in-depth market survey on Global and Chinese Malonic Acid industry. The report firstly reviews the basic information of Malonic Acid including its ...
 
Nature.com
Thu, 20 Nov 2014 05:43:24 -0800

Previous work by the Schulz laboratory has demonstrated that a single point mutation in an acyltransferase domain facilitated the incorporation of a propargylated malonic acid building block into the antibiotic erythromycin3. To translate this result ...
 
Business Wire (press release)
Tue, 26 Aug 2014 09:07:30 -0700

Global Market Report of Malonic acid (CAS 141-82-2) aims at providing comprehensive data on Malonic acid globally and regionally (Europe, Asia, North America, Latin America etc.). It captures Malonic acid market trends, pays close attention to Malonic ...
 
Biomass Magazine
Tue, 28 Oct 2014 16:03:45 -0700

“That grant is really focused on how you get malonic acid out of the fermentation process at a low cost and high efficiency,” Dietrich said. “I would say, that the techniques for developing for that process would ideally then be useful for other ...
 
Chemistry World
Mon, 21 Nov 2011 07:31:58 -0800

Hitomi Onuma and colleagues have now looked at a Belousov-Zhabotinsky reaction that involves the oscillation of ferroin ([Fe(phen)3]2+) and ferrin ([Fe(phen)3]3+) ions with sodium bromate and malonic acid components. The reaction mixture oscillates ...
 
Geek
Fri, 23 Aug 2013 07:41:58 -0700

This is one of several reactions that serve as an example of non-equilibrium thermodynamics. The expanding rings are a “chemical oscillator.” The malonic acid and potassium bromate react to produce carbon dioxide, water, and bromine. The rings expand ...

University of Texas at Dallas (press release)

University of Texas at Dallas (press release)
Mon, 20 May 2013 14:49:59 -0700

Synthesis and Hyperpolarization of 13C-Labeled Malonic Acid Derivatives as Potential Ph-Sensitive Probes for Metabolic Imaging of Cancer. Dr. Dean Sherry. Advanced Imaging Research Center. Lee, Hyo Min. Rapid Magnetic Resonance Spectroscopic ...
 
io9
Mon, 20 Feb 2012 11:00:34 -0800

... but researchers are still trying to understand how this reaction — which involves an impressive cocktail requiring various quantities of water, hydrogen peroxide, soluble starch, potassium iodate, sulfuric acid, malonic acid and manganese sulfate ...
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