Acetonedicarboxylic acid

Acetonedicarboxylic acid, 3-oxoglutaric acid or β-ketoglutaric acid is a simple dicarboxylic acid with the formula O=C(CH₂CO₂H)₂. β-Ketoglutarate does not have the biological activity exhibited by α-ketoglutarate.^[2]

Acetonedicarboxylic acid^[1]

Skeletal formula
Ball-and-stick model
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 Y
3D model (JSmol)	Interactive image Interactive image
ChEBI	CHEBI:88950
ChemSpider	61623 Y
ECHA InfoCard	100.007.999
EC Number	208-797-9
PubChem CID	68328
UNII	IH7P7WO21P Y
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) 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
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, 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). N verify (what is YN ?) Infobox references

Preparation

Acetonedicarboxylic acid can also be prepared by decarboxylation of citric acid in fuming sulfuric acid:^[3]

Applications

Acetonedicarboxylic acid and its esters such as dimethylacetonedicarboxylate are primarily used as building blocks in the synthesis of heterocyclic rings^[4] and in the Weiss–Cook reaction.^[5]

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

The presence of β-ketoglutaric acid in human urine is diagnostic for the harmful gut flora such as Candida albicans.^[6]

See also

• alpha-Ketoglutaric acid