Acetonedicarboxylic acid

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Acetonedicarboxylic acid[1]
Skeletal formula
Ball-and-stick model
Names
IUPAC name
3-Oxopentanedioic acid
Other names
  • 1,3-Acetonedicarboxylic acid
  • 3-oxoglutaric acid
  • 3-ketoglutaric acid
  • β-ketoglutaric acid
Identifiers
542-05-2 N
ChemSpider 61623 YesY
EC number 208-797-9
Jmol-3D images Image
Image
PubChem 68328
Properties
C5H6O5
Molar mass 146.09814 g/mol
Density 1,499 g/cm3
Melting point 122 °C (252 °F; 395 K) (decomposes)
Boiling point 408.4 °C (767.1 °F; 681.5 K)
Hazards
Flash point 214.9 °C (418.8 °F; 488.0 K)
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N verify (what isYesY/N?)
Infobox references

Acetonedicarboxylic acid, 3-oxoglutaric acid or β-ketoglutaric acid is a simple dicarboxylic acid. It is commercially available but may also be prepared by decarbonylation of citric acid in fuming sulfuric acid:[2]

Acetonedicarboxylic acid from citric acid.png

Acetonedicarboxylic acid and its derivatives are primarily used as a building blocks in organic chemistry, particuarly in the synthesis of hetrocyclic rings[3] and in the Weiss–Cook reaction.

The presence of β-ketoglutaric acid in human urine can be used as a diagnostic test for the overgrowth of harmful gut flora such as Candida albicans.[4]

See Also[edit]

References[edit]

  1. ^ 1,3-Acetonedicarboxylic acid at Sigma-Aldrich (safety data sheet)
  2. ^ Roger Adams, H. M. Chiles, and C. F. Rassweiler (1941). "Acetonedicarboxylic Acid". Org. Synth. ; Coll. Vol. 1, p. 10 
  3. ^ Stanovnik, Branko; Grošelj, Uroš (2010). "CHAPTER 5 – Dialkyl Acetone-1,3-Dicarboxylates and their Mono- and bis(Dimethylamino)methylidene Derivatives in the Synthesis of Heterocyclic Systems". Advances in Heterocyclic Chemistry 100: 145–174. doi:10.1016/S0065-2725(10)10005-1. 
  4. ^ Schmidt, Michael A, Tired of Being Tired: Overcoming Chronic Fatigue and Low Energy