Acetonedicarboxylic acid, 3-oxoglutaric acid or β-ketoglutaric acid is a simple
dicarboxylic acid
In organic chemistry, a dicarboxylic acid is an organic compound containing two carboxyl groups (). The general molecular formula for dicarboxylic acids can be written as , where R can be aliphatic or aromatic. In general, dicarboxylic acids show ...
.
Preparation
Acetonedicarboxylic acid can also be prepared by
decarboxylation
Decarboxylation is a chemical reaction that removes a carboxyl group and releases carbon dioxide (CO2). Usually, decarboxylation refers to a reaction of carboxylic acids, removing a carbon atom from a carbon chain. The reverse process, which is t ...
of
citric acid
Citric acid is an organic compound with the chemical formula HOC(CO2H)(CH2CO2H)2. It is a colorless weak organic acid. It occurs naturally in citrus fruits. In biochemistry, it is an intermediate in the citric acid cycle, which occurs in t ...
in fuming
sulfuric acid
Sulfuric acid (American spelling and the preferred IUPAC name) or sulphuric acid ( Commonwealth spelling), known in antiquity as oil of vitriol, is a mineral acid composed of the elements sulfur, oxygen and hydrogen, with the molecular formu ...
:
:
Applications
Acetonedicarboxylic acid and its esters such as dimethylacetonedicarboxylate are primarily used as building blocks in the synthesis of heterocyclic rings and in the
Weiss–Cook reaction.
Acetonedicarboxylic acid is well known to be used in the Robinson
tropinone
Tropinone is an alkaloid, famously synthesised in 1917 by Robert Robinson as a synthetic precursor to atropine, a scarce commodity during World War I. Tropinone and the alkaloids cocaine and atropine all share the same tropane core structure. I ...
synthesis.
The presence of β-ketoglutaric acid in human urine is diagnostic for the harmful gut flora such as ''
Candida albicans
''Candida albicans'' is an opportunistic pathogenic yeast that is a common member of the human gut flora. It can also survive outside the human body. It is detected in the gastrointestinal tract and mouth in 40–60% of healthy adults. It is us ...
''.
[Schmidt, Michael A, ''Tired of Being Tired: Overcoming Chronic Fatigue and Low Energy'']
See also
*
alpha-Ketoglutaric acid
References
Dicarboxylic acids
Beta-keto acids