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/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 verify (what is YN ?)

Infobox references

Chemical compound

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

[edit]

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

## Biosynthesis

[edit]

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

[edit]

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

[edit]

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

[edit]

### Medicinal uses

[edit]

In medicinal chemistry, chalcones have been used as:

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

### Industrial uses

[edit]

In chemical industries, they are employed as:

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

### Uses in organic chemistry

[edit]

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

## See also

[edit]

* Juliá–Colonna epoxidation

## References

[edit]

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. ^ a b 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. ^ a b 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

[edit]

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

*[CID]: Compound ID
*[EPA]: U.S. Environmental Protection Agency