Chalcone

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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	55–57 °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. Some chalcones demonstrated the ability to block voltage-dependent potassium channels. ^[2] 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.

[edit] 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.^[3] The reaction between substituted benzaldehydes and acetophenones has been used to demonstrate green chemistry in undergraduate chemistry education.^[4] In a study investigating green chemistry synthesis, chalcones were also synthesized from the same starting materials in high temperature water (200 to 350 °C).^[5]

[edit] References

1. ^ Merck Index, 11th Edition, 2028.
2. ^ Yarishkin, O.V., et al, Bioorg. Med. Chem. Lett., 18, (2008), 137–140.
3. ^ Toda, F., et al, J. Chem. Soc. Perkin Trans. I, 1990, 3207.
4. ^ Palleros, D. R., J. Chem. Educ., 81, 1345 (2004).
5. ^ Comisar, C. M. and Savage, P. E. Green Chem., 6 (2004), 227 - 231. doi:10.1039/b314622g