digplanet beta 1: Athena
Share digplanet:


Applied sciences






















Not to be confused with malic acid or maleic acid.
Malonic acid
Malonic acid
CAS number 141-82-2 YesY
PubChem 867
ChemSpider 844 YesY
DrugBank DB02175
ChEBI CHEBI:30794 YesY
Jmol-3D images Image 1
Image 3
Molecular formula C3H4O4
Molar mass 104.06 g mol−1
Density 1.619 g/cm3
Melting point 135 to 137 °C (275 to 279 °F; 408 to 410 K) (decomposes)
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
dimethyl malonate
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'.


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.


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.


  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.
486 videos foundNext > 

Malonic Ester Synthesis

This video describes the malonic ester synthesis. This is a companion video to the acetoacetic ester synthesis video. Please watch the acetoacetic ester synt...

B/Z Oscillating reaction.

16cm3 of Malonic Acid, 16cm3 of Cerium (IV) Ammonium Sulphate Dihydrate. 16cm3 of Potassium Bromate, 0.8cm3 of Ferroin Indicator. = Awesomeness.

Kenshirohwang (Aku/Jin) VS Malonic Acid (Juri/Nina) STREET FIGHTER X TEKKEN

Sorry forgot to edit this video! sorry my viewers! Much More Replays from this channel! - Subscribe to get more! Street Fighter x Tekken Replay SFxT Kenshiro...

Chlorite-Iodide-Malonic Acid (CIMA) Reaction

http://demonstrations.wolfram.com/ChloriteIodideMalonicAcidCIMAReaction The Wolfram Demonstrations Project contains thousands of free interactive visualizati...

Malonic acid

3D model of Malonic acid.

Malonic Ester Synthesis

Describes the use in organic synthesis and reaction mechanism of the malonic ester synthesis to make carboxylic acids.

Bellevue College Chemistry Club Experiment: Belousov-Zhabotinsky Reaction

Week One Chem-Club Experiment. BZ-Reaction; An Oscillating Reduction-Oxidation Reaction. Steps: 1) Dissolve 9.5g Potassium Bromate in 250mL distilled water t...

Amino Acid 20: Malonic Ester Synthesis

Amino Acid 21: Malonic Ester Example


The decarboxylation (loss of carbon dioxide) of malonic acid and a beta-keto acid More free lessons at: http://www.khanacademy.org/video?v=8G0RkfeKfBg.

486 videos foundNext > 

26 news items

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

Although Lygos cannot share specifics on the awarded phase one project, the phase two project receiving $450,000 will develop new purification techniques for organic acids, specifically looking at malonic acid, which is Lygos's first product. “Lygos ...
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 ...

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 ...
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 ...
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 ...
Chemistry World
Wed, 16 May 2012 07:25:04 -0700

The phenomenon is driven by redox swings in the reaction mixture, as ruthenium(II) is first oxidised to ruthenium(III) by bromate and reduced back again by malonic acid. Because ruthenium(III) increases the polymer's hydrophobicity, the gel swells at ...
Chemistry World
Tue, 29 May 2012 08:41:15 -0700

He was investigating an oscillating reaction called the chlorite–iodide–malonic acid (CIMA) reaction, which shares some ingredients with the Belousov–Zhabotinsky reaction, and in 1985 he and his colleagues had begun to look at spatial patterns in this ...

Oops, we seem to be having trouble contacting Twitter

Support Wikipedia

A portion of the proceeds from advertising on Digplanet goes to supporting Wikipedia. Please add your support for Wikipedia!

Searchlight Group

Digplanet also receives support from Searchlight Group. Visit Searchlight