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.[3]
Uvitonic acid is obtained by the action of ammonia on glutaric acid.
Pyrogallol can be produced from glutaric diester.[4]

Safety

Glutaric acid may cause irritation to the skin and eyes.[5] Acute hazards include the fact that this compound may be harmful by ingestion, inhalation or skin absorption.[5]

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, Pentanedioic acid, 99%". Chemkits.eu. Retrieved 2020-09-29.
, "Method of synthesis of pyrogallol", issued 1976-02-17
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

[3] "Glutaric acid, Pentanedioic acid, 99%". Chemkits.eu. Retrieved 2020-09-29.

[4] , "Method of synthesis of pyrogallol", issued 1976-02-17

[cameochemicals-5] Glutaric acid, cameochemicals.com