Acetoacetic acid: Difference between revisions

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{{short description|Chemical compound}}
= Acetoacetic acid =
{{Chembox
| ImageFile = Acetoacetic_acid.png
| ImageSize = 200px
| ImageAlt = Structural formula of acetoacetic acid
| IUPACName = 3-Oxobutanoic acid
| OtherNames = Acetoacetic acid
| Section1 = {{Chembox Identifiers
  | CASNo = 541-50-4
  | PubChem = 1140
  | ChemSpiderID = 1105
  }}
| Section2 = {{Chembox Properties
  | C=4
  | H=6
  | O=3
  | Appearance = Colorless liquid
  | Density = 1.1 g/cm_
  | MeltingPt = -3 °C
  | BoilingPt = 175 °C
  }}
}}


'''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.
[[File:Acetoacetic_acid.png|thumb|right|Structure of acetoacetic acid]]


==Structure and Properties==
'''Acetoacetic acid''' is a [[beta-keto acid]] with the chemical formula C<sub>4</sub>H<sub>6</sub>O<sub>3</sub>. It is an important intermediate in the [[ketone bodies]] metabolism and is involved in various biochemical pathways.
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.


[[File:3-Oxobutyric_acid_KetoEnol.svg|thumb|center|500px|Keto-enol tautomerism of acetoacetic acid]]
== Structure and Properties ==


==Synthesis==
[[File:Acetoacetic-acid-3D-balls.png|thumb|right|3D ball model of acetoacetic acid]]
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.


[[File:DiketeneReaction.svg|thumb|center|500px|Hydrolysis of diketene to form acetoacetic acid]]
Acetoacetic acid is a [[keto acid]] that contains both a ketone group and a carboxylic acid group. It exists in equilibrium with its [[enol]] form, which is a characteristic feature of beta-keto acids. The compound is a colorless liquid with a pungent odor and is soluble in water.


==Biological Role==
== Keto-Enol Tautomerism ==
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==
[[File:3-Oxobutyric_acid_KetoEnol.svg|thumb|right|Keto-enol tautomerism of acetoacetic acid]]
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 exhibits keto-enol tautomerism, where the keto form (3-oxobutyric acid) and the enol form are in dynamic equilibrium. This tautomerism is important in its reactivity and stability.
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.
 
== Biological Role ==
 
Acetoacetic acid is one of the three [[ketone bodies]] produced in the liver during the breakdown of [[fatty acids]]. It serves as an important energy source during periods of fasting, prolonged exercise, or low-carbohydrate diets. The other ketone bodies are [[beta-hydroxybutyrate]] and [[acetone]].
 
== Synthesis ==
 
Acetoacetic acid can be synthesized through the [[Claisen condensation]] of [[ethyl acetate]] with [[acetone]]. It is also produced in the body from the breakdown of [[fatty acids]] in the liver.
 
== Reactions ==
 
Acetoacetic acid is a versatile intermediate in organic synthesis. It can undergo decarboxylation to form [[acetone]] and carbon dioxide. It can also participate in various condensation reactions, such as the [[Diketene]] reaction.
 
[[File:DiketeneReaction.svg|thumb|right|Diketene reaction involving acetoacetic acid]]
 
== Uses ==
 
Acetoacetic acid and its esters are used in the synthesis of [[dyes]], [[pharmaceuticals]], and [[flavoring agents]]. Its derivatives are also used in the production of [[vitamins]] and [[hormones]].
 
== Safety ==
 
Acetoacetic acid is a corrosive substance and should be handled with care. It can cause irritation to the skin, eyes, and respiratory tract.
 
== Related pages ==


==Related pages==
* [[Ketone bodies]]
* [[Ketone bodies]]
* [[Beta-hydroxybutyrate]]
* [[Beta-hydroxybutyrate]]
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* [[Fatty acid metabolism]]
* [[Fatty acid metabolism]]


==Gallery==
== Gallery ==
 
<gallery>
<gallery>
File:Acetoacetic-acid-3D-balls.png|3D model of acetoacetic acid
File:YellowPig5thTry.png|Illustration of acetoacetic acid
File:YellowPig5thTry.png|Illustration of acetoacetic acid
</gallery>
</gallery>


[[Category:Keto acids]]
[[Category:Keto acids]]
[[Category:Ketone bodies]]
[[Category:Metabolism]]
[[Category:Biochemistry]]
[[Category:Organic chemistry]]

Revision as of 21:22, 11 February 2025

Acetoacetic acid

Structure of acetoacetic acid

Acetoacetic acid is a beta-keto acid with the chemical formula C4H6O3. It is an important intermediate in the ketone bodies metabolism and is involved in various biochemical pathways.

Structure and Properties

3D ball model of acetoacetic acid

Acetoacetic acid is a keto acid that contains both a ketone group and a carboxylic acid group. It exists in equilibrium with its enol form, which is a characteristic feature of beta-keto acids. The compound is a colorless liquid with a pungent odor and is soluble in water.

Keto-Enol Tautomerism

Keto-enol tautomerism of acetoacetic acid

Acetoacetic acid exhibits keto-enol tautomerism, where the keto form (3-oxobutyric acid) and the enol form are in dynamic equilibrium. This tautomerism is important in its reactivity and stability.

Biological Role

Acetoacetic acid is one of the three ketone bodies produced in the liver during the breakdown of fatty acids. It serves as an important energy source during periods of fasting, prolonged exercise, or low-carbohydrate diets. The other ketone bodies are beta-hydroxybutyrate and acetone.

Synthesis

Acetoacetic acid can be synthesized through the Claisen condensation of ethyl acetate with acetone. It is also produced in the body from the breakdown of fatty acids in the liver.

Reactions

Acetoacetic acid is a versatile intermediate in organic synthesis. It can undergo decarboxylation to form acetone and carbon dioxide. It can also participate in various condensation reactions, such as the Diketene reaction.

Diketene reaction involving acetoacetic acid

Uses

Acetoacetic acid and its esters are used in the synthesis of dyes, pharmaceuticals, and flavoring agents. Its derivatives are also used in the production of vitamins and hormones.

Safety

Acetoacetic acid is a corrosive substance and should be handled with care. It can cause irritation to the skin, eyes, and respiratory tract.

Related pages

Gallery

  • Illustration of acetoacetic acid
    Illustration of acetoacetic acid
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