Chalcone

Chalcone¹

Names
Preferred IUPAC name Chalcone2
Systematic IUPAC name (2E)-1,3-Diphenylprop-2-en-1-one
Other names Chalkone Benzylideneacetophenone Phenyl styryl ketone benzalacetophenone β-phenylacrylophenone γ-oxo-α,γ-diphenyl-α-propylene α-phenyl-β-benzoylethylene.
Identifiers
CAS Number	94-41-7 614-47-1 ((E)-Chalcone) Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:27618 Y
ChemSpider	6921 Y
ECHA InfoCard	100.002.119
PubChem CID	637760
UNII	5S5A2Q39HX Y
CompTox Dashboard (EPA)	DTXSID20873536
InChI InChI=1S/C15H12O/c16-15(14-9-5-2-6-10-14)12-11-13-7-3-1-4-8-13/h1-12H Y Key: DQFBYFPFKXHELB-UHFFFAOYSA-N Y InChI=1/C15H12O/c16-15(14-9-5-2-6-10-14)12-11-13-7-3-1-4-8-13/h1-12H Key: DQFBYFPFKXHELB-UHFFFAOYAP
SMILES O=C(C=Cc1ccccc1)c2ccccc2
Properties
Chemical formula	C15H12O
Molar mass	208.260 g·mol−1
Appearance	pale yellow solid
Density	1.071 g/cm3
Melting point	55 to 57 °C (131 to 135 °F; 328 to 330 K)
Boiling point	345 to 348 °C (653 to 658 °F; 618 to 621 K)
Magnetic susceptibility (χ)	−125.7·10−6 cm3/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

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.³ They are widely known bioactive substances, fluorescent materials, and chemical intermediates.

Chalcones have two absorption maxima at 280 nm and 340 nm.⁴

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.⁵

Chalcone is usually prepared by an aldol condensation between benzaldehyde and acetophenone. ^{6 7}

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.⁸

Chalcones and their derivatives demonstrate a wide range of biological activities including anti-inflammation.⁹ Some 2′-amino chalcones have been studied as potential antitumor agents.¹⁰¹¹ Chalcones are of interest in medicinal chemistry and have been described as a privileged scaffold.⁵

In medicinal chemistry, chalcones have been used as:

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

In chemical industries, they are employed as:

• liquid crystals
• fluorescent chemical scaffolds
• metal sensors
• corrosion inhibitors
• plant hormones¹²

Chalcones have been used as intermediates in heterocyclic synthesis, especially in the synthesis of pyrazoles and aurones.¹²

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.¹³ 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].

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).