Glutaric acid

Glutaric acid
IUPAC name pentanedioic acid
Other names Propane-1,3-dicarboxylic acid; 1,3-propanedicarboxylic acid; pentanedioic acid; n-Pyrotartaric acid
Identifiers
CAS number	110-94-1 Y
PubChem	743
ChemSpider	723 Y
EC number	203-817-2
DrugBank	DB03553
KEGG	C00489 Y
ChEBI	CHEBI:17859 Y
ChEMBL	CHEMBL1162495 Y
Jmol-3D images	Image 1
SMILES C(CC(=O)O)CC(=O)O
InChI InChI=1S/C5H8O4/c6-4(7)2-1-3-5(8)9/h1-3H2,(H,6,7)(H,8,9) Y Key: JFCQEDHGNNZCLN-UHFFFAOYSA-N Y InChI=1/C5H8O4/c6-4(7)2-1-3-5(8)9/h1-3H2,(H,6,7)(H,8,9) Key: JFCQEDHGNNZCLN-UHFFFAOYAU
Properties
Molecular formula	C5H8O4
Molar mass	132.12 g/mol
Melting point	95 to 98 °C
Boiling point	200 °C/20 mmHg
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Glutaric acid is the organic compound with the formula C₃H₆(COOH)₂ . Although the related "linear" dicarboxylic acids adipic and succinic acids are water-soluble only to a few percent at room temperature, the water-solubility of glutaric acid is over 50%. The term glutaric is derived from glu[ten] + [tar]taric acid.

Biochemistry

Glutaric acid is naturally produced in the body during the metabolism of some amino acids, including lysine and tryptophan. Defects in this metabolic pathway can lead to a disorder called glutaric aciduria, where toxic byproducts build up and can cause severe encephalopathy.

Production

Glutaric acid can be prepared by the ring-opening of butyrolactone with potassium cyanide to give the mixed potassium carboxylate-nitrile that is hydrolyzed to the diacid.^[1] Alternatively hydrolysis, followed by oxidation of dihydropyran gives glutaric acid. It can also be prepared from reacting 1,3-dibromopropane with sodium or potassium cyanide to obtain the dinitrile, followed by hydrolysis.

Uses

1,5-Pentanediol, a common plasticizer and precursor to polyesters is manufactured by hydrogenation of glutaric acid and its derivatives.^[2]

Glutaric acid itself has been used in the production of polymers such as polyester polyols, polyamides. The odd number of carbon atoms (i.e. 5) is useful in decreasing polymer elasticity.^{[citation needed]}

References

1. ↑ G. Paris, L. Berlinguet, R. Gaudry, J. English, Jr. and J. E. Dayan (1963), "Glutaric Acid and Glutaramide", Org. Synth. ; Coll. Vol. 4: 496 
2. ↑ Peter Werle and Marcus Morawietz "Alcohols, Polyhydric" in Ullmann's Encyclopedia of Industrial Chemistry: 2002, Wiley-VCH: Weinheim. DOI 10.1002/14356007.a01_305

External links

• Calculator: Water and solute activities in aqueous glutaric acid