Chalcone

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Chalcone

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Template:Longitem	Template:Chembox Elements/molecular formula
Molar mass	Template:Chem molar mass
Appearance	pale yellow solid
Density	1.071 g/cm3
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Template:Longitem	−125.7·10−6 cm3/mol

Chalcone is the organic compound C₆H₅C(O)CH=CHC₆H₅. It is an α,β-unsaturated ketone. A variety of important biological compounds are known collectively as chalcones or chalconoids. They are widely known bioactive substances, fluorescent materials, and chemical intermediates.

Chemical properties

Chalcones have two absorption maxima at 280 nm and 340 nm.

Biosynthesis

Chalcones and chalconoids are synthesized in plants as secondary metabolites. The enzyme chalcone synthase, a type III polyketide synthase, is responsible for the biosynthesis of these compounds. The enzyme is found in all "higher" (vascular) and several "lower" (non-vascular) plants.

Laboratory synthesis

Chalcone is usually prepared by an aldol condensation between benzaldehyde and acetophenone.

preparation of chalcone

This reaction, which can be carried out without any solvent, is so reliable that it is often given as an example of green chemistry in undergraduate education.

Potential pharmacology

Chalcones and their derivatives demonstrate a wide range of biological activities including anti-inflammation. Some 2′-amino chalcones have been studied as potential antitumor agents. Chalcones are of interest in medicinal chemistry and have been described as a privileged scaffold.

Uses

Medicinal uses

In medicinal chemistry, chalcones have been used as:

• antioxidants
• anticancer agents
• antidiabetic drugs
• antiviral drugs
• antimalarial drugs

Industrial uses

In chemical industries, they are employed as:

• liquid crystals
• fluorescent chemical scaffolds
• metal sensors
• corrosion inhibitors
• plant hormones

Uses in organic chemistry

Chalcones have been used as intermediates in heterocyclic synthesis, especially in the synthesis of pyrazoles and aurones.

In the Johnson–Corey–Chaykovsky reaction, chalcone reacts with dimethylsulfoxonium methylide to give 1-phenyl-2-benzoylcyclopropane [15295-43-9] [1145-91-1] in 95% yield. A Leuckart reaction or ammonium acetate in the presence of sodium cyanoborohydride would be predicted to give Phenyl(2-phenylcyclopropyl)methanamine [1559116-96-9]. Alternatively if a reductive amination of the ketone with methylamine is performed one would instead get the secondary amine N-Me [1559367-56-4].

Corey's tranylcypromine

Corey's tranylcypromine

These compounds have the same trans-stereochemistry as was observed for tranylcypromine although their exact mode of pharmacology is still lacking. Lastly, it was discovered that if a hydrazine is prepared from the ketone (ala pheniprazine) one gets a compound that is called [Phenyl-(2-phenylcyclopropyl)methyl]hydrazine (PC105199424).

See also

• Juliá–Colonna epoxidation

External links

• Chalcone on reference.md