Chalcone

Chalcone

Names
Preferred IUPAC name Chalcone
Systematic IUPAC name (2E)-1,3-Diphenylprop-2-en-1-one
Other names Chalkone Benzylideneacetophenone Phenyl styryl ketone
Identifiers
CAS Number	94-41-7 Y 614-47-1 ((E)-Chalcone) N
3D model (Jmol)	Interactive image
ChEBI	CHEBI:27618 Y
ChemSpider	6921 Y
ECHA InfoCard	100.002.119
PubChem	637760
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	208.26 g·mol−1
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  (what is YN ?)
Infobox references

Chalcone is an aromatic ketone and an enone that forms the central core for a variety of important biological compounds, which are known collectively as chalcones or chalconoids. Benzylideneacetophenone is the parent member of the chalcone series. The alternative name given to chalcone are phenyl styryl ketone, benzalacetophenone, β-phenylacrylophenone, ɣ-oxo-α,ɣ-diphenyl-α-propylene and α-phenyl-β-benzoylethylene.

Chalcones and their derivatives demonstrate wide range of biological activities such as anti-diabetic, anti-neoplastic, anti-hypertensive, anti-retroviral, anti-inflammatory, anti-parasitic, anti-histaminic, anti-malarial, anti-oxidant, anti-fungal, anti-obesity, anti-platelet, anti-tubercular, immunosuppressant, anti-arrhythmic, hypnotic, anti-gout, anxiolytic, anti-spasmodic, anti-nociceptive, hypolipidemic, anti-filarial, anti-angiogenic, anti-protozoal, anti-bacterial, anti-steroidal, cardioprotective, etc.

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

Chalcones can be prepared by an aldol condensation between benzaldehyde and 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. The reaction between substituted benzaldehydes and acetophenones can be used as an example of green chemistry in undergraduate education. In a study investigating green syntheses, chalcones were synthesized from the same starting materials in high-temperature water (200 to 350 °C).

Substituted chalcones were also synthesised by piperidine-mediated condensation to avoid side reactions such as multiple condensations, polymerizations, and rearrangements.

An example is the conjugate reduction of the enone by tributyltin hydride: