Acetonedicarboxylic acid

From Wikipedia, the free encyclopedia
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
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.007.999 Edit this at Wikidata
EC Number
  • 208-797-9
UNII
  • InChI=1S/C5H6O5/c6-3(1-4(7)8)2-5(9)10/h1-2H2,(H,7,8)(H,9,10) checkY
    Key: OXTNCQMOKLOUAM-UHFFFAOYSA-N checkY
  • InChI=1/C5H6O5/c6-3(1-4(7)8)2-5(9)10/h1-2H2,(H,7,8)(H,9,10)
    Key: OXTNCQMOKLOUAM-UHFFFAOYAR
  • C(C(=O)CC(=O)O)C(=O)O
  • O=C(O)CC(=O)CC(=O)O
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
GHS labelling:
GHS07: Exclamation mark
Signal word
 Warning
H315, H319, H335
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  (what is checkY☒N ?)
Infobox references

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

Preparation[]

Acetonedicarboxylic acid can also be prepared by decarboxylation of citric acid in fuming sulfuric acid:[2]

Acetonedicarboxylic acid from citric acid.png

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]

See also[]

  • alpha-Ketoglutaric acid

References[]

  1. ^ 1,3-Acetonedicarboxylic acid[permanent dead link] at Sigma-Aldrich (safety data sheet)
  2. ^ Roger Adams; H. M. Chiles; C. F. Rassweiler (1925). "Acetonedicarboxylic Acid". Organic Syntheses. 5: 5. doi:10.15227/orgsyn.005.0005.
  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
Retrieved from ""