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Acetonedicarboxylic acid

Acetonedicarboxylic acid
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
3D model (Jmol)
ChemSpider
ECHA InfoCard 100.007.999
EC Number 208-797-9
PubChem CID
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) (760mm Hg)
Hazards
Flash point 214.9 °C (418.8 °F; 488.0 K)
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

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:

Acetonedicarboxylic acid and its derivatives are primarily used as building blocks in organic chemistry, particularly in the synthesis of heterocyclic rings and in the Weiss–Cook reaction.

Acetonedicarboxylic acid is well-known to be used in the Robinson tropinone synthesis.

Acetonedicarboxylic acid also finds use in the synthesis of Timcodar & dezaguanine (3-deazaguanine, 3-DG).

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.


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