Chemical compound
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]
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
- ^ |ALDRICH&N5=SEARCH_CONCAT_PNO|BRAND_KEY&F=SPEC 1,3-Acetonedicarboxylic acid{{|bot=InternetArchiveBot |fix-attempted=yes }} at Sigma-Aldrich (safety data sheet)
- ^ Roger Adams; H. M. Chiles; C. F. Rassweiler (1925). "Acetonedicarboxylic Acid". Organic Syntheses. 5: 5. doi:10.15227/orgsyn.005.0005.
- ^ 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.
- ^ 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.
- ^ Schmidt, Michael A, Tired of Being Tired: Overcoming Chronic Fatigue and Low Energy
