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Under typical physiological conditions, acetoacetic acid exists as its conjugate base, acetoacetate: AcCH 2 CO 2 H → AcCH 2 CO − 2 + H + Unbound acetoacetate is primarily produced by liver mitochondria from its thioester with coenzyme A (CoA): AcCH 2 C(O)−CoA + OH − → AcCH 2 CO − 2 + H−CoA. The acetoacetate-CoA itself is formed by ...
Acetoacetic ester synthesis is a chemical reaction where ethyl acetoacetate is alkylated at the α-carbon to both carbonyl groups and then converted into a ketone, or more specifically an α-substituted acetone. This is very similar to malonic ester synthesis. Acetoacetic ester synthesis equation
Ketone bodies are water-soluble molecules or compounds that contain the ketone groups produced from fatty acids by the liver (ketogenesis). [1] [2] Ketone bodies are readily transported into tissues outside the liver, where they are converted into acetyl-CoA (acetyl-Coenzyme A) – which then enters the citric acid cycle (Krebs cycle) and is oxidized for energy.
The enzyme acetoacetyl-CoA hydrolase (EC 3.1.2.11) catalyzes the reaction . acetoacetyl-CoA + H 2 O CoA + acetoacetate. This enzyme belongs to the family of hydrolases, specifically those acting on thioester bonds.
The original Knorr synthesis employed two equivalents of ethyl acetoacetate, one of which was converted to ethyl 2-oximinoacetoacetate by dissolving it in glacial acetic acid, and slowly adding one equivalent of saturated aqueous sodium nitrite, under external cooling. Zinc dust was then stirred in, reducing the oxime group to the amine. This ...
Technically there are other ketone esters such as acetoacetate bound to D/L 1,3-butanediol (racemic). This diester has been tested more with deep sea divers. It is not commercially available. [10] Another ketone ester is also referred to as a ketone di-ester which is a bond of C6 and R 1,3 butanediol or C8 and R 1,3 butanediol.
OXCT1 is a member of the CoA transferase family I, which is known to catalyze the transfer of CoA between carboxylic acid groups. [9] [10] In particular, OXCT1 catalyzes the first, rate-limiting step in ketolysis by transferring the CoA from succinyl-CoA to acetoacetate, giving acetoacetyl-CoA (AcAc-CoA).
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