Glutaric acid, also termed pentanedioic acid or n-pyrotartaric acid, is an alpha, omega-dicarboxylic acid with the formula C3H6(COOH)2. The body naturally produces glutaric acid as a by-product during the metabolism of some amino acids, such as lysine and tryptophan. It is an organic compound that appears as colorless crystals or white solids. It decomposes slightly at a temperature of 302-304 °C. At room temperature, the solubility of the related "linear" dicarboxylic acids adipic and succinic acids in water is only a few percent, whereas glutaric acid has a water-solubility of approximately 50% (w/w). Its conjugate bases are glutarate (1-) and glutarate. It functions as both a human and a Daphnia Magna metabolite. Glutaric acid is used as a precursor in organic synthesis.
Structure of Glutaric Acid
Glutaric acid is a linear five-carbon dicarboxylic acid that has a chemical formula of C5H8O4 or C3H6(COOH)2 or COOH(CH2)3COOH. It is composed of 5 carbon atoms, 8 hydrogen atoms, and 4 oxygen atoms. C(CC(=O)O)CC(=O)O is its canonical SMILES structure.
It can be prepared by the oxidative ring fission of cyclopentane with 50% of nitric acid in the presence of vanadium cyanide.
It is produced as a by-product in the production of adipic acid from cyclohexane by oxidation with air and nitric acid.
We can also prepare glutaric acid by reacting 1,3-dibromopropane with sodium or potassium cyanide to produce the dinitrile, followed by hydrolysis.
Properties of Glutaric Acid
Chemical formula
C5H8O4
IUPAC Name
Pentanedioic acid
Molecular weight
132.12 g/mol
Appearance
Colorless crystals or white solid
Density
1.4 g/cm³
Melting point
95 to 98 °C
Boiling point
200 °C at 20 mmHg
Solubility
Soluble in water, freely soluble in absolute alcohol, ether, soluble in benzene, chloroform, and slightly soluble in petroleum ether.
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
4
Uses of Glutaric Acid
Glutaric acid is used as a precursor in organic synthesis. For example, uvitonic acid is produced by the action of ammonia on glutaric acid. It is also used in the preparation of its anhydride and esters.
Glutaric diester can be used for the production of pyrogallol.
It is also used in the manufacture of various polymers such as polyamides and polyesters.
Through the hydrogenation of glutaric acid and its derivatives, 1,5-Pentanediol is produced, which is a common plasticizer and precursor to polyesters.
Health Hazards
Glutaric acid may irritate the skin and eyes.
Some chronic hazards of this compound are that it might be harmful when inhaled, ingested, or absorbed through the skin.
On heating for decomposition, it may emit acrid smoke, irritating fumes, and toxic fumes of carbon dioxide and carbon monoxide.
