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Acetonedicarboxylic acid

From Wikipedia, the free encyclopedia
Acetonedicarboxylic acid[1]
Skeletal formula
Skeletal formula
Ball-and-stick model
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 InfoCard100.007.999Edit 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 mass146.09814 g/mol
Density1.499 g/cm3
Melting point122 °C (252 °F; 395 K) (decomposes)
Boiling point408.4 °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 point214.9 °C (418.8 °F; 488.0 K)
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

Acetonedicarboxylic acid,3-oxoglutaric acid orβ-ketoglutaric acid is a simpledicarboxylic acid with the formulaO=C(CH2CO2H)2. β-Ketoglutarate does not have the biological activity exhibited byα-ketoglutarate.[2]

Preparation

[edit]

Acetonedicarboxylic acid can also be prepared bydecarboxylation ofcitric acid in fumingsulfuric acid:[3]

Applications

[edit]

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

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

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

See also

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References

[edit]
  1. ^|ALDRICH&N5=SEARCH_CONCAT_PNO|BRAND_KEY&F=SPEC 1,3-Acetonedicarboxylic acid{{|bot=InternetArchiveBot |fix-attempted=yes }} atSigma-Aldrich (safety data sheet)
  2. ^Bhatkar D, Ananda N, Lokhande KB, Khunteta K, Jain P, Hebale A, Sarode SC, Sharma NK (September 2023)."Organic Acids Derived from Saliva-amalgamated Betel Quid Filtrate Are Predicted as a Ten-eleven Translocation-2 Inhibitor".Journal of Cancer Prevention.28 (3):115–130.doi:10.15430/JCP.2023.28.3.115.PMC 10564634.PMID 37830116.
  3. ^Roger Adams; H. M. Chiles; C. F. Rassweiler (1925). "Acetonedicarboxylic Acid".Organic Syntheses.5: 5.doi:10.15227/orgsyn.005.0005.
  4. ^Stanovnik, Branko; Grošelj, Uroš (2010). "Dialkyl Acetone-1,3-Dicarboxylates and their Mono- and bis(Dimethylamino)methylidene Derivatives in the Synthesis of Heterocyclic Systems".Advances in Heterocyclic Chemistry Volume 100. Vol. 100. pp. 145–174.doi:10.1016/S0065-2725(10)10005-1.ISBN 9780123809360.
  5. ^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.
  6. ^Schmidt, Michael A,Tired of Being Tired: Overcoming Chronic Fatigue and Low Energy
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