Acetoacetic acid
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Acetoacetic acid (also known as 3-oxobutanoic acid) is a beta-keto acid with the chemical formula CH_COCH_COOH. It is an important intermediate in the ketone bodies metabolism and is involved in various biochemical pathways.
Structure and Properties
Acetoacetic acid is a simple keto acid that contains both a ketone group and a carboxylic acid group. It is a colorless liquid at room temperature and has a characteristic odor. The compound is known for its keto-enol tautomerism, where it can exist in two forms: the keto form and the enol form. The keto form is more stable and predominant in solution.
Synthesis
Acetoacetic acid can be synthesized through the Claisen condensation of ethyl acetate with sodium ethoxide followed by acidification. It can also be produced by the hydrolysis of diketene in the presence of water.
Biological Role
In biological systems, acetoacetic acid is one of the three ketone bodies produced during the breakdown of fatty acids. It is synthesized in the liver and can be converted into acetone or beta-hydroxybutyrate. These ketone bodies are used as an energy source by various tissues, especially during periods of fasting, starvation, or low-carbohydrate diets.
Applications
Acetoacetic acid is used in the synthesis of various pharmaceuticals and as a building block in organic chemistry. It is also used in the production of dyes, perfumes, and flavoring agents.
Safety and Handling
Acetoacetic acid should be handled with care as it is a corrosive substance. It can cause burns upon contact with skin and eyes, and inhalation of its vapors can be harmful. Proper protective equipment should be used when handling this chemical.
Related pages
Gallery
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3D model of acetoacetic acid -
Illustration of acetoacetic acid
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