Glutaric acid

Glutaric acid
Names
	Preferred IUPAC name Pentanedioic acid
	Other names Glutaric acid; Propane-1,3-dicarboxylic acid; 1,3-Propanedicarboxylic acid; Pentanedioic acid; n-Pyrotartaric acid
Identifiers
CAS Number	110-94-1 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:17859 ;
ChEMBL	ChEMBL1162495 ;
ChemSpider	723 ;
DrugBank	DB03553 ;
ECHA InfoCard	100.003.471
EC Number	203-817-2;
KEGG	C00489 ;
PubChem CID	743;
UNII	H849F7N00B ;
CompTox Dashboard (EPA)	DTXSID2021654 ;
	InChI InChI=1S/C5H8O4/c6-4(7)2-1-3-5(8)9/h1-3H2,(H,6,7)(H,8,9) Key: JFCQEDHGNNZCLN-UHFFFAOYSA-N ; InChI=1/C5H8O4/c6-4(7)2-1-3-5(8)9/h1-3H2,(H,6,7)(H,8,9) Key: JFCQEDHGNNZCLN-UHFFFAOYAU;
	SMILES C(CC(=O)O)CC(=O)O;
Properties
Chemical formula	C5H8O4
Molar mass	132.12 g/mol
Melting point	95 to 98 °C (203 to 208 °F; 368 to 371 K)
Boiling point	200 °C (392 °F; 473 K) /20 mmHg
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	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% (w/w).

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.
Uvitonic acid is obtained by the action of ammonia on glutaric acid.

Safety

Glutaric acid may cause irritation to the skin and eyes.[3] Acute hazards include the fact that this compound may be harmful by ingestion, inhalation or skin absorption.[3]

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References

G. Paris, L. Berlinguet, R. Gaudry, J. English, Jr. and J. E. Dayan (1963). "Glutaric Acid and Glutaramide". Organic Syntheses.CS1 maint: multiple names: authors list (link); Collective Volume, 4, p. 496
Peter Werle and Marcus Morawietz "Alcohols, Polyhydric" in Ullmann's Encyclopedia of Industrial Chemistry: 2002, Wiley-VCH: Weinheim. DOI 10.1002/14356007.a01_305
Glutaric acid, cameochemicals.com

External links

Calculator: Water and solute activities in aqueous glutaric acid

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[1] G. Paris, L. Berlinguet, R. Gaudry, J. English, Jr. and J. E. Dayan (1963). "Glutaric Acid and Glutaramide". Organic Syntheses.CS1 maint: multiple names: authors list (link); Collective Volume, 4, p. 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

[cameochemicals-3] Glutaric acid, cameochemicals.com