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.
Preparation of Glutaric Acid
- Glutaric acid can be synthesized from malonic ester synthesis, where diiodomethane reacts with the two-molar equivalent of diethyl malonate.
- 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.