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.
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Preferred IUPAC name
Chalcone[2] | |
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. | |
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3D model (JSmol)
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ChEBI |
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ECHA InfoCard | 100.002.119 |
PubChem CID
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CompTox Dashboard (EPA)
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Properties | |
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) |
-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).
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Infobox references
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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]
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.[7]
Chalcones and their derivatives demonstrate a wide range of biological activities including anti-inflammation.[8] Some 2′-amino chalcones have been studied as potential antitumor agents.[9][10] Chalcones are of interest in medicinal chemistry and have been described as a privileged scaffold.[5]
In medicinal chemistry, chalcones have been used as:
In chemical industries, they are employed as:
Chalcones have been used as intermediates in heterocyclic synthesis, especially in the synthesis of pyrazoles and aurones.[12]