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Chalcone



For the genus of grass skipper butterflies, see Chalcone (butterfly).
Chalcone[1]
IUPAC name 1,3-Diphenyl-2-propen-1-one
Other names Chalcone
Chalkone
Benzylideneacetophenone
Phenyl styryl ketone
Identifiers
CAS number 614-47-1
Properties
Molecular formula C15H12O
Molar mass 208.26 g/mol
Density 1.071 g/cm3
Melting point

129.7–130.9 °C

Boiling point

345-348 °C

Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

Chalcone is an aromatic ketone that forms the central core for a variety of important biological compounds, which are known collectively as chalcones. They show antibacterial, antifungal, antitumor and anti-inflammatory properties. They are also intermediates in the biosynthesis of flavonoids, which are substances widespread in plants and with an array of biological activities. Chalcones are also intermediates in the Auwers synthesis of flavones.

Additional recommended knowledge

Synthesis

Chalcones can be prepared by an aldol condensation between a benzaldehyde and an acetophenone in the presence of sodium hydroxide as a catalyst.

This reaction has been found to work without any solvent at all - a solid-state reaction.[2] The reaction between substituted benzaldehydes and acetophenones has been used to demonstrate green chemistry in undergraduate chemistry education.[3] In a study investigating green chemistry synthesis, chalcones were also synthesized from the same starting materials in high temperature water (200 to 350 °C).[4]

References

  1. ^ Merck Index, 11th Edition, 2028.
  2. ^ Toda, F., et al, J. Chem. Soc. Perkin Trans. I, 1990, 3207.
  3. ^ Palleros, D. R., J. Chem. Educ., 81, 1345 (2004).
  4. ^ Comisar, C. M. and Savage, P. E. Green Chem., 6 (2004), 227 - 231. doi:10.1039/b314622g
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Chalcone". A list of authors is available in Wikipedia.
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