Acetonedicarboxylic acid

Acetonedicarboxylic acid^[1]

Names
IUPAC name 3-Oxopentanedioic acid
Other names 1,3-Acetonedicarboxylic acid 3-oxoglutaric acid 3-ketoglutaric acid β-ketoglutaric acid
Identifiers
CAS Number	542-05-2
ChemSpider	61623
EC Number	208-797-9
Jmol 3D model	Interactive image Interactive image
PubChem	68328
InChI InChI=1S/C5H6O5/c6-3(1-4(7)8)2-5(9)10/h1-2H2,(H,7,8)(H,9,10) Key: OXTNCQMOKLOUAM-UHFFFAOYSA-N InChI=1/C5H6O5/c6-3(1-4(7)8)2-5(9)10/h1-2H2,(H,7,8)(H,9,10) Key: OXTNCQMOKLOUAM-UHFFFAOYAR
SMILES C(C(=O)CC(=O)O)C(=O)O O=C(O)CC(=O)CC(=O)O
Properties
Chemical formula	C5H6O5
Molar mass	146.09814 g/mol
Density	1,499 g/cm^3
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:^[2]

Acetonedicarboxylic acid and its derivatives are primarily used as a building blocks in organic chemistry, particularly 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

• alpha-Ketoglutaric acid

References

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