Chalcone

For the butterflies, see Chalcone (skipper).

Chalcone[1]

Names
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.
Identifiers
CAS Number	94-41-7 614-47-1 ((E)-Chalcone)^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:27618^Y
ChemSpider	6921^Y
ECHA InfoCard	100.002.119
PubChem CID	637760
UNII	5S5A2Q39HX^Y
CompTox Dashboard (EPA)	DTXSID20873536
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	208.260 g·mol^−1
Appearance	pale yellow solid
Density	1.071 g/cm^3
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 cm^3/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references

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.

Chemical properties

Chalcones have two absorption maxima at 280 nm and 340 nm.[4]

Biosynthesis

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]

Laboratory synthesis

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]

Potential pharmacology

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]

Uses

Medicinal uses

In medicinal chemistry, chalcones have been used as:

• antioxidants
• Anticancer agents
• antidiabetic drugs
• antiviral drugs
• antimalarial drugs and more.

Industrial uses

In chemical industries, they are employed as:

• liquid crystals
• fluorescent chemical scaffolds
• metal sensors
• corrosion inhibitors
• plant hormones.[11]

Uses in organic chemistry

Chalcones have been used as intermediates in heterocyclic synthesis, especially in the synthesis of pyrazoles and aurones.[11]

See also

• Juliá–Colonna epoxidation

References

1. Merck Index, 11th Edition, 2028
2. "Front Matter". Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 722. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
3. Tomás-Barberán, Francisco A.; Clifford, Michael N. (2000). "Flavanones, Chalcones and Dihydrochalcones - Nature, Occurrence and Dietary Burden". Journal of the Science of Food and Agriculture. 80 (7): 1073–1080. doi:10.1002/(SICI)1097-0010(20000515)80:7<1073::AID-JSFA568>3.0.CO;2-B.
4. Song, Dong-mee; Jung, Kyoung-Hoon; Moon, Ji-hye; Shin, Dong-Myung (2003). "Photochemistry of chalcone and the application of chalcone-derivatives in photo-alignment layer of liquid crystal display". Optical Materials. 21 (1–3): 667–71. Bibcode:2003OptMa..21..667S. doi:10.1016/S0925-3467(02)00220-3.
5. Zhuang, Chunlin; Zhang, Wen; Sheng, Chunquan; Zhang, Wannian; Xing, Chengguo; Miao, Zhenyuan (28 June 2017). "Chalcone: A Privileged Structure in Medicinal Chemistry". Chemical Reviews. 117 (12): 7762–7810. doi:10.1021/acs.chemrev.7b00020. PMC 6131713. PMID 28488435.
6. E. P. Kohler, H. M. Chadwell (1922). "Benzalacetophenone". Organic Syntheses. 2: 1. doi:10.15227/orgsyn.002.0001.
7. Palleros, Daniel R (2004). "Solvent-Free Synthesis of Chalcones". Journal of Chemical Education. 81 (9): 1345. Bibcode:2004JChEd..81.1345P. doi:10.1021/ed081p1345.
8. Mahapatra, Debarshi Kar; Bharti, Sanjay Kumar; Asati, Vivek (2017). "Chalcone Derivatives: Anti-inflammatory Potential and Molecular Targets Perspectives". Current Topics in Medicinal Chemistry. 17 (28): 3146–3169. doi:10.2174/1568026617666170914160446. PMID 28914193.
9. Xia, Yi; Yang, Zheng-Yu; Xia, Peng; Bastow, Kenneth F.; Nakanishi, Yuka; Lee, Kuo-Hsiung (2000). "Antitumor agents. Part 202: Novel 2′-amino chalcones: design, synthesis and biological evaluation". Bioorganic & Medicinal Chemistry Letters. 10 (8): 699–701. doi:10.1016/S0960-894X(00)00072-X. ISSN 0960-894X. PMID 10782667.
10. Santos, Mariana B.; Pinhanelli, Vitor C.; Garcia, Mayara A.R.; Silva, Gabriel; Baek, Seung J.; França, Suzelei C.; Fachin, Ana L.; Marins, Mozart; Regasini, Luis O. (2017). "Antiproliferative and pro-apoptotic activities of 2′- and 4′-aminochalcones against tumor canine cells" (PDF). European Journal of Medicinal Chemistry. 138: 884–889. doi:10.1016/j.ejmech.2017.06.049. hdl:11449/174929. ISSN 0223-5234. PMID 28738308.
11. Nayak, Yogeesha N.; Gaonkar, Santosh L.; Sabu, Mariya (2023-01-04). "Chalcones: Versatile intermediates in heterocyclic synthesis". Journal of Heterocyclic Chemistry: jhet.4617. doi:10.1002/jhet.4617. ISSN 0022-152X. S2CID 255212828.

External links

• Chalcone on reference.md Archived 2020-09-25 at the Wayback Machine