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Not to be confused with malic acid or maleic acid.
Malonic acid
Skeletal formula of malonic acid
Ball-and-stick model of the malonic acid molecule
Names
IUPAC name
propanedioic acid
Other names
methanedicarboxylic acid
Identifiers
141-82-2 YesY
ChEBI CHEBI:30794 YesY
ChEMBL ChEMBL7942 YesY
ChemSpider 844 YesY
DrugBank DB02175 YesY
Jmol-3D images Image
Image
PubChem 867
Properties
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
Miscible
Acidity (pKa) pKa1 = 2.83[1]
pKa2 = 5.69[1]
Related compounds
Other anions
malonate
acetic acid
oxalic acid
propionic acid
tartronic acid
acrylic acid
butyric acid
succinic acid
fumaric acid
Related compounds
propanone
propionaldehyde
propanedial
dimethyl malonate
Hazards
Safety data sheet External MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 YesY verify (what isYesY/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[2] (complex II) in the respiratory electron transport chain.

Preparation[edit]

A classical preparation of malonic acid starts from chloroacetic acid:[3]

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.[4]

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.

Malonic acid is also known to be a competitive inhibitor of succinic dehydrogenase, the enzyme responsible for the dehydrogenation of succinate within Krebs cycle.

Applications[edit]

Malonic acid is a precursor to specialty polyesters. It can also be a component in alkyd resins. It is used in a number of manufacturing processes including the electronics industry.

Malonic acid is used as a building block chemical to produce numerous valuable compounds.[5]

References[edit]

  1. ^ a b pKa Data Compiled by R. Williams (pdf; 77 kB)
  2. ^ Pardee, Arthur B.; Potter, Van R. (26 October 1948). "Malonate Inhibition of Oxidations in the Krebs Tricarboxylic Acid Cycle" (PDF). Journal of Biological Chemistry (178): 241–250. Retrieved 5 June 2015. 
  3. ^ Nathan Weiner. "Malonic acid". Org. Synth. ; Coll. Vol. 2, p. 376 
  4. ^ See:
  5. ^ Malonic Acid & Derivatives

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.
452 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 ...

Malonic acid

3D model of Malonic acid.

Decarboxylation

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.

Malonic Ester Synthesis

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

Malic acid Meaning

Video shows what malic acid means. A colourless crystalline dicarboxylic acid, hydroxy-malonic acid, found in wine, apples and other fruit; it is converted to ...

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 ...

Malonic acid Meaning

Video shows what malonic acid means. a white crystalline dicarboxylic acid, CH2(COOH)2, used in making barbiturates. Malonic acid Meaning. How to ...

Chlorite-Iodide-Malonic Acid (CIMA) Reaction

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

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 ...

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.

452 videos foundNext > 

32 news items

Biomass Magazine

Biomass Magazine
Tue, 10 Mar 2015 15:52:30 -0700

Lygos Inc., an industrial biotechnology company, recently announced that it has successfully achieved pilot-scale production of malonic acid from sugar. Malonic acid is a high-value specialty chemical useful for production of a variety of ...

Chemicals Technology

Chemicals Technology
Thu, 05 Mar 2015 04:00:00 -0800

Lygos has completed the pilot-scale production of malonic acid using renewable resources at Lawrence Berkeley National Laboratory's advanced bio-fuels process demonstration unit (ABPDU). The new manufacturing technology is said to replace the ...
 
Biobased Digest
Sun, 08 Mar 2015 22:03:45 -0700

In California, Lygos has successfully achieved pilot scale production of malonic acid from sugar. A versatile compound, malonic acid was identified by the U.S. Department of Energy as one of the “Top 30 Value Added Chemicals” to be produced from ...
 
Biomass Magazine
Tue, 28 Oct 2014 16:03:45 -0700

Biomass Magazine reported in 2012 that the company could not disclose specifically which molecules they were targeting, but now the company is speaking publically about their first product, malonic acid. “That grant is really focused on how you get ...

Biobased Digest

Biobased Digest
Tue, 23 Jun 2015 19:37:30 -0700

But that technology has pathways to a collection of target molecules, which include acrylonitrile, as well as butanol, BDO, 3-HP, acetyl-CoA, malonyl-CoA, malonate semialdehyde, 3-HP, acrylic acid, PDO, malonic acid, ethyl 3-HP, propiolactone ...

Biobased Digest

Biobased Digest
Wed, 29 Apr 2015 13:15:12 -0700

But the company had pathways to a multi-billion dollar market, via a collection of target molecules, including: butanol, BDO, 3-HP, acetyl-CoA, malonyl-CoA, malonate semialdehyde, 3-HP, acrylic acid, PDO, malonic acid, ethyl 3-HP, propiolactone ...

Biomass Magazine

Biomass Magazine
Mon, 27 Apr 2015 15:07:30 -0700

BioAmber Inc. has been chosen by Bayer MaterialScience as the supplier of bio-succinic acid used to produce a new range of innovative, biobased polyurethanes for textile applications that Bayer MaterialScience has begun commercializing.
 
Biobased Digest
Mon, 02 Mar 2015 22:56:15 -0800

As a first step in its pioneering journey to manufacture bio-sourced isobutene, Global Bioenergies has been using first generation feedstock, such as wheat-derived glucose, to set-up and optimize its bio-isobutene process. However, the process was ...
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