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Acetonedicarboxylic acid

Acetonedicarboxylic acid (also known as 3-oxoglutaric acid or β-ketoglutaric acid) is a simple dicarboxylic acid with the formula . β-Ketoglutarate does not have the biological activity exhibited by α-ketoglutarate.

Preparation

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

:[[Image:Acetonedicarboxylic acid from citric acid.png|450px]]

Applications

Acetonedicarboxylic acid and its esters such as dimethylacetonedicarboxylate are primarily used as building blocks in the synthesis of heterocyclic rings{{Cite book | last1 = Stanovnik | first1 = Branko | last2 = Grošelj | first2 = Uroš

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.

References

References

  1. [http://www.sigmaaldrich.com/US/en/product/aldrich/165115
  2. (September 2023). "Organic Acids Derived from Saliva-amalgamated Betel Quid Filtrate Are Predicted as a Ten-eleven Translocation-2 Inhibitor". Journal of Cancer Prevention.
  3. Roger Adams. (1925). "Acetonedicarboxylic Acid".
  4. (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.
  5. Schmidt, Michael A, ''Tired of Being Tired: Overcoming Chronic Fatigue and Low Energy''
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dicarboxylic-acids beta-keto-acids
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