Glutaric acid

Glutaric acid
Skeletal formula of glutaric acid
Ball-and-stick model of the glutaric acid molecule
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) checkY
    Key: JFCQEDHGNNZCLN-UHFFFAOYSA-N checkY
  • 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).
checkY verify (what is checkY☒N ?)
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 potassium salt of the 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. Using periodate, it is obtained from oxidation of 1,3-cyclohexanedione, which proceeds with decarboxylation.[2]

Uses

  • 1,5-Pentanediol, a common plasticizer and precursor to polyesters is manufactured by hydrogenation of glutaric acid and its derivatives.[3]
  • 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.[4]
  • Pyrogallol can be produced from glutaric diester.[5]

Safety

Glutaric acid may cause irritation to the skin and eyes.[6] Acute hazards include the fact that this compound may be harmful by ingestion, inhalation or skin absorption.[6]

References

  1. ↑ G. Paris, L. Berlinguet, R. Gaudry, J. English, Jr. and J. E. Dayan (1957). "Glutaric Acid and Glutaramide". Organic Syntheses: 47. doi:10.15227/orgsyn.037.0047{{cite journal}}: CS1 maint: multiple names: authors list (link).
  2. ↑ Smith, Michael B.; March, Jerry (2007), Advanced Organic Chemistry: Reactions, Mechanisms, and Structure (6th ed.), New York: Wiley-Interscience, p. 1736, ISBN 978-0-471-72091-1
  3. ↑ Peter Werle and Marcus Morawietz "Alcohols, Polyhydric" in Ullmann's Encyclopedia of Industrial Chemistry: 2002, Wiley-VCH: Weinheim. DOI 10.1002/14356007.a01_305
  4. ↑ "Glutaric acid, Pentanedioic acid, 99%". Chemkits.eu. Retrieved 2020-09-29.
  5. ↑ US 4046817, Shipchandler, Mohammed T., "Method of synthesis of pyrogallol", published 1977-09-06, assigned to IMC Chemical Group
  6. 1 2 Glutaric acid, cameochemicals.com
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