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Acetoacetic acid
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Acetoacetic acid
Acetoacetic acid (IUPAC name: 3-oxobutanoic acid, also known as acetonecarboxylic acid or diacetic acid) is the organic compound with the formula CH3COCH2COOH. It is the simplest beta-keto acid, and like other members of this class, it is unstable. The methyl and ethyl esters, which are quite stable, are produced on a large scale industrially as precursors to dyes. Acetoacetic acid is a weak acid.
Under typical physiological conditions, acetoacetic acid exists as its conjugate base, acetoacetate:
Unbound acetoacetate is primarily produced by liver mitochondria from its thioester with coenzyme A (CoA):
The acetoacetyl-CoA itself is formed by three routes:
In mammals, acetoacetate produced in the liver (along with the other two "ketone bodies") is released into the bloodstream as an energy source during periods of fasting, exercise, or as a result of type 1 diabetes mellitus. First, a CoA group is enzymatically transferred to it from succinyl CoA, converting it back to acetoacetyl CoA; this is then broken into two acetyl CoA molecules by thiolase, and these then enter the citric acid cycle. Heart muscle and renal cortex prefer acetoacetate over glucose. The brain uses acetoacetate when glucose levels are low due to fasting or diabetes.
Acetoacetic acid may be prepared by the hydrolysis of diketene. Its esters are produced analogously via reactions between diketene and alcohols, and acetoacetic acid can be prepared by the hydrolysis of these species. In general, acetoacetic acid is generated at 0 °C and used in situ immediately.
It decomposes at a moderate reaction rate into acetone and carbon dioxide:
The acid form has a half-life of 140 minutes at 37 °C in water, whereas the basic form (the anion) has a half-life of 130 hours. That is, it reacts about 55 times more slowly. The corresponding decarboxylation of trifluoroacetoacetate is used to prepare trifluoroacetone:
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Acetoacetic acid
Acetoacetic acid (IUPAC name: 3-oxobutanoic acid, also known as acetonecarboxylic acid or diacetic acid) is the organic compound with the formula CH3COCH2COOH. It is the simplest beta-keto acid, and like other members of this class, it is unstable. The methyl and ethyl esters, which are quite stable, are produced on a large scale industrially as precursors to dyes. Acetoacetic acid is a weak acid.
Under typical physiological conditions, acetoacetic acid exists as its conjugate base, acetoacetate:
Unbound acetoacetate is primarily produced by liver mitochondria from its thioester with coenzyme A (CoA):
The acetoacetyl-CoA itself is formed by three routes:
In mammals, acetoacetate produced in the liver (along with the other two "ketone bodies") is released into the bloodstream as an energy source during periods of fasting, exercise, or as a result of type 1 diabetes mellitus. First, a CoA group is enzymatically transferred to it from succinyl CoA, converting it back to acetoacetyl CoA; this is then broken into two acetyl CoA molecules by thiolase, and these then enter the citric acid cycle. Heart muscle and renal cortex prefer acetoacetate over glucose. The brain uses acetoacetate when glucose levels are low due to fasting or diabetes.
Acetoacetic acid may be prepared by the hydrolysis of diketene. Its esters are produced analogously via reactions between diketene and alcohols, and acetoacetic acid can be prepared by the hydrolysis of these species. In general, acetoacetic acid is generated at 0 °C and used in situ immediately.
It decomposes at a moderate reaction rate into acetone and carbon dioxide:
The acid form has a half-life of 140 minutes at 37 °C in water, whereas the basic form (the anion) has a half-life of 130 hours. That is, it reacts about 55 times more slowly. The corresponding decarboxylation of trifluoroacetoacetate is used to prepare trifluoroacetone:
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