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Malonic acid - C3H4O4

Malonic acid is a dicarboxylic acid with a chemical formula C3H4O4. Dicarboxylic acids are organic compounds containing two carboxylic acid functional groups. Dicarboxylic acids generally show the same chemical behaviour and reactivity as monocarboxylic acids. Malonic acid is a substance found in some fruits that occurs naturally. Fruits generated in organic farming contain greater concentrations of malonic acid in citrus compared to fruits generated in conventional farming.

The systematic name for malonic acid IUPAC is propanedioic acid. Malonic acid is the archetypal instance of a competitive inhibitor: it functions in the respiratory electron transport chain against succinate dehydrogenase. Malonic acid is correlated with deficiency of malonyl-CoA decarboxylase, an inborn metabolism mistake.

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What is Malonic acid?

Malonic acid is also known as Propanedioic Acid or Dicarboxymethane. The name is derived from a Greek word Malon which means apple. Malonates are the ionized form of malonic acid, along with its esters and salts. It appears as a white crystal or crystalline powder. It dissolves in alcohol, pyridine, and ether.

Malonic acid was first prepared in the year, 1858 by the French chemist Victor Dessaignes by the oxidation of malic acid. Malonic acid is found in some fruit’s viz citrus fruits. The amount of malonic acid produced from fruits through organic farming is greater than the fruits grown through conventional agriculture. Malonic acid can be produced through the fermentation of glucose.

Malonic acid Structure – C3H4O4

Structure of Malonic acid

Properties of Malonic acid – C3H4O4

C3H4O4 Malonic acid
Molecular Weight/ Molar Mass 104.061 g/mol
Density 1.619 g/cm³
Boiling Point Decomposes
Melting Point 135 to 137°C

Malonic acid Synthesis – C3H4O4

Preparation of malonic acid starts with chloroacetic acid which is also known as MCA (monochloroacetic acid).

Step 1: Sodium carbonate produces sodium salt.

Step 2: It is made to react with sodium cyanide.

Step 3: cyanoacetic acid salt is generated through nucleophilic substitution.

Step 4: The nitrile group is hydrolyzed with sodium hydroxide to produce sodium malonate.

Step 5: The acidification results in malonic acid.

Industrially, malonic acid is produced by the hydrolysis of diethyl malonate or dimethyl malonate. Never give anything by mouth to an unconscious person. Rinse the mouth with water. Malonic acid is a forerunner to polyester specialities. Malonic acid is used to generate countless useful compounds as a construction block chemical.

Uses of Malonic acid – (C3H4O4)

The uses of malonic acid are listed below.

  • Malonic acid is used as a precursor in polymers and polyester.
  • It is used in flavours as well as the fragrance industry.
  • It is used to control the acidity.
  • It is used in pharmaceutical products.
  • It is used as a cross-linking agent between potato starch and cornstarch to enhance its mechanical properties.
  • It is used in the preparation of barbituric salt.
  • It is used in electroplating.
  • It is used to produce vitamin B1, vitamin B6, vitamin B2, and amino acids.
  • It is used in chemical synthesis as a building block.

Malonic acid Health Risks

  • It is a strong irritant and is harmful when harmful by inhaled, ingested or absorbed by the skin leading to skin damage and damage to mucous membranes.
  • A few laboratory animal toxicity studies of malonic acid, but the studies are insufficient to define extra health impacts.
  • If inhaled, it may be dangerous. Causes irritation of the respiratory tract. If absorbed through the skin, it may be dangerous. It causes irritation of the skin.
  • When breathed in, move fresh air into the individual. Give artificial respiration if you don’t breathe. Consult a doctor.

Frequently Asked Questions- FAQs

What happens when malonic acid is heated?

On heating malonic acid produces acetic acid and carbon dioxide.

Is malonic acid strong?

Malonic acid is a diprotic acid. pKa value of first loss of proton is 2.83, and second loss proton is 5.69 . Higher the pka value, the less acidic strength. So that the malonic acid is a medium strong acid.

What is the source of malonic acid?

Malonic acid is found in many fruits and vegetables. The calcium salt of malonic acid occurs in high concentrations in beetroot.

What is malonic acid soluble in?

Malonic acid is soluble in water, It is a polar molecule, form H+ ion in aqueous solution , it is also soluble in methyl alcohol but insoluble in hexane.

Is maleic acid optically active?

Maleic acid does not have any chiral centre, so it does not exhibit optical isomerism.

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