Chalcone
- For the genus of grass skipper butterflies, see Chalcone (butterfly).
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| Names | |
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| IUPAC name
1,3-Diphenyl-2-propen-1-one
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| Other names
Chalcone
Chalkone Benzylideneacetophenone Phenyl styryl ketone | |
| Identifiers | |
3D model (JSmol)
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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 | 208.26 g/mol |
| Density | 1.071 g/cm3 |
| Melting point | 55–57 °C |
| Boiling point | 345-348 °C |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Chalcone (and related compounds "chalconoids") 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.
Methyl hydroxychalcone (MCHP, molecular formula : C16H14O2, molar mass : 238.28 g/mol, exact mass : 238.09938, PubChem CID : 6440383), found in cinnamon, was thought to be an insulin mimetic, improving insulin response of diabetics.[3] It has since been determined that a flavonoid is responsible for the insulin-like biological activity.[4]
Synthesis
Chemical 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.[5] The reaction between substituted benzaldehydes and acetophenones has been used to demonstrate green chemistry in undergraduate chemistry education.[6] In a study investigating green chemistry synthesis, chalcones were also synthesized from the same starting materials in high temperature water (200 to 350 °C).[7]
Biosynthesis/metabolism
Chalcone synthase is responsible for the production of chalcones in plants.
Chalcone isomerase is responsible for their conversion into flavanones and other flavonoids.
Naringenin-chalcone synthase uses malonyl-CoA and 4-coumaroyl-CoA to produce CoA, naringenin chalcone, and CO2.
In aurones, chalcone closes into a 5 instead of the more typical 6 atoms ring (C ring).
See also
References
- ^ Merck Index, 11th Edition, 2028.
- ^ Yarishkin, O.V., et al., Bioorg. Med. Chem. Lett., 18, (2008), 137–140.
- ^
Anderson (2001). "A hydroxychalcone derived from cinnamon functions as a mimetic for insulin in 3T3-L1 adipocytes". J Am Coll Nutr. 20 (4): 327–36. PMID 11506060. Retrieved 2008-06-19.
{{cite journal}}: Unknown parameter|day=ignored (help); Unknown parameter|month=ignored (help) - ^ Anderson (2004). "Isolation and characterization of polyphenol type-A polymers from cinnamon with insulin-like biological activity". J Agric Food Chem. 52 (1): 65–70. doi:10.1021/jf034916b. PMID 14709014.
{{cite journal}}: Unknown parameter|month=ignored (help) - ^ Toda, F., et al., J. Chem. Soc. Perkin Trans. I, 1990, 3207.
- ^ Palleros, D. R., J. Chem. Educ., 81, 1345 (2004).
- ^ Comisar, C. M. and Savage, P. E. Green Chem., 6 (2004), 227 - 231. doi:10.1039/b314622g