Acetonedicarboxylic acid

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

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
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
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 verify (what is checkY☒N ?)
Infobox references

Preparation

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

Applications

Acetonedicarboxylic acid and its esters such as dimethylacetonedicarboxylate are primarily used as building blocks in the synthesis of heterocyclic rings[3] and in the Weiss–Cook reaction.[4]

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.[5]

See also

References
  1. |ALDRICH&N5=SEARCH_CONCAT_PNO|BRAND_KEY&F=SPEC 1,3-Acetonedicarboxylic acid{{|bot=InternetArchiveBot |fix-attempted=yes }} 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. Vol. 100. pp. 145–174. doi:10.1016/S0065-2725(10)10005-1. ISBN 9780123809360.
  4. Korman, Matthew; Paz, Eric; Franklin, Tylor; Lewandowski, Nicholas R.; Sullivan, Bethany; Imhoff, Andrea M.; Fisher, Luke; Bichler, Katherine A.; Van Ornum, Scott G. (2020). "Process Development of the Weiss–Cook Reaction for the Preparation of cis-1,5-Dimethylbicyclo[3.3.0]octane-3,7-dione in the Undergraduate Organic Laboratory". Journal of Chemical Education. 97 (10): 3835–3838. Bibcode:2020JChEd..97.3835K. doi:10.1021/acs.jchemed.9b00653. S2CID 225248640.
  5. Schmidt, Michael A, Tired of Being Tired: Overcoming Chronic Fatigue and Low Energy
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