Glutaric acid

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).

Not to be confused with Glutamic 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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.003.471
EC Number
  • 203-817-2
KEGG
PubChem CID
UNII
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
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).
Y verify (what is YN ?)
Infobox references

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]
  • 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
  1. G. Paris, L. Berlinguet, R. Gaudry, J. English, Jr. and J. E. Dayan (1963). "Glutaric Acid and Glutaramide". Organic Syntheses.{{cite journal}}: CS1 maint: multiple names: authors list (link); Collective Volume, vol. 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. US 4046817, Shipchandler, Mohammed T., "Method of synthesis of pyrogallol", published 1977-09-06, assigned to IMC Chemical Group
  5. Glutaric acid, cameochemicals.com
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