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
1,5-Pentanedioic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.003.471 Edit this at Wikidata
EC Number
  • 203-817-2
26809
KEGG
UNII
  • 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
  • C(CC(=O)O)CC(=O)O
Properties
C5H8O4
Molar mass 132.115 g·mol−1
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 checkYX markN ?)

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). [citation needed]

Biochemistry

Glutaric acid is naturally produced in the body during the metabolism of some amino acids, including lysine and tryptophan. It can also arise by chain extension of α-ketoglutarate to α-ketoadipate.

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. 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.

Uses

Safety

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

References

  1. ↑ Wang, Jian; Wu, Yifei; Sun, Xinxiao; Yuan, Qipeng; Yan, Yajun (2017). "De Novo Biosynthesis of Glutarate via α-Keto Acid Carbon Chain Extension and Decarboxylation Pathway in Escherichia coli". ACS Synthetic Biology. 6 (10): 1922–1930. doi:10.1021/acssynbio.7b00136. PMID 28618222.
  2. ↑ 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).
  3. ↑ 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
  4. ↑ Peter Werle and Marcus Morawietz "Alcohols, Polyhydric" in Ullmann's Encyclopedia of Industrial Chemistry: 2002, Wiley-VCH: Weinheim. DOI 10.1002/14356007.a01_305
  5. ↑ "Glutaric acid, Pentanedioic acid, 99%". Chemkits.eu. Retrieved 2020-09-29.
  6. ↑ US 4046817, Shipchandler, Mohammed T., "Method of synthesis of pyrogallol", published 1977-09-06, assigned to IMC Chemical Group
  7. 1 2 Glutaric acid, cameochemicals.com