Acetonedicarboxylic acid

Acetonedicarboxylic acid[1]
Names
	Preferred 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 ;
3D model (JSmol)	Interactive image; Interactive image;
ChEBI	CHEBI:88950;
ChemSpider	61623 ;
ECHA InfoCard	100.007.999
EC Number	208-797-9;
PubChem CID	68328;
UNII	IH7P7WO21P ;
CompTox Dashboard (EPA)	DTXSID2060252 ;
	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/cm3
Melting point	122 °C (252 °F; 395 K) (decomposes)
Boiling point	408.4 °C (767.1 °F; 681.5 K) (760mm Hg)
Hazards
GHS pictograms
GHS Signal word	Warning
GHS hazard statements	H315, H319, H335
GHS precautionary statements	P261, P264, P271, P280, P302+352, P304+340, P305+351+338, P312, P321, P332+313, P337+313, P362, P403+233, P405, P501
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.

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.

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]

References

1,3-Acetonedicarboxylic acid at Sigma-Aldrich (safety data sheet)
Roger Adams; H. M. Chiles; C. F. Rassweiler (1941). "Acetonedicarboxylic Acid". Organic Syntheses.; Collective Volume, 1, p. 10
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. Advances in Heterocyclic Chemistry. 100: 145–174. doi:10.1016/S0065-2725(10)10005-1. ISBN 9780123809360.
Schmidt, Michael A, Tired of Being Tired: Overcoming Chronic Fatigue and Low Energy

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[1] 1,3-Acetonedicarboxylic acid at Sigma-Aldrich (safety data sheet)

[2] Roger Adams; H. M. Chiles; C. F. Rassweiler (1941). "Acetonedicarboxylic Acid". Organic Syntheses.; Collective Volume, 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. Advances in Heterocyclic Chemistry. 100: 145–174. doi:10.1016/S0065-2725(10)10005-1. ISBN 9780123809360.

[4] Schmidt, Michael A, Tired of Being Tired: Overcoming Chronic Fatigue and Low Energy

Acetonedicarboxylic acid

Preparation

Applications

See also

References