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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
SDS External MSDS
Except where noted otherwise, data is 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 (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.

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.[4]

References[edit]

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

External links[edit]


Original courtesy of Wikipedia: http://en.wikipedia.org/wiki/Malonic_acid — Please support Wikipedia.
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