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 N
3D model (Jmol)	Interactive image Interactive image
ChemSpider	61623 Y
ECHA InfoCard	100.007.999
EC Number	208-797-9
PubChem	68328
InChI InChI=1S/C5H6O5/c6-3(1-4(7)8)2-5(9)10/h1-2H2,(H,7,8)(H,9,10) Y Key: OXTNCQMOKLOUAM-UHFFFAOYSA-N Y 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/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).
N verify (what is YN ?)
Infobox references

Acetonedicarboxylic acid, 3-oxoglutaric acid or β-ketoglutaric acid is a simple dicarboxylic acid.

Preparation

It is commercially available but may also be prepared by decarbonylation of citric acid in fuming sulfuric acid:^[2]

Applications

Acetonedicarboxylic acid and its derivatives are primarily used as building blocks in organic chemistry, particularly in the synthesis of heterocyclic rings^[3] 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.^[4]

See also

• alpha-Ketoglutaric acid

References

1. ↑ 1,3-Acetonedicarboxylic acid at Sigma-Aldrich (safety data sheet)
2. ↑ Roger Adams; H. M. Chiles; 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