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| ImageSize1 = 220
| ImageSize1 = 220
| ImageAlt1 = Ball-and-stick model of the chalcone molecule
| ImageAlt1 = Ball-and-stick model of the chalcone molecule
| ImageFile2 =
| PIN = Chalcone<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = [[Royal Society of Chemistry|The Royal Society of Chemistry]] | date = 2014 | location = Cambridge | page = 722 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4| chapter = Front Matter }}</ref>
| PIN = Chalcone<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = [[Royal Society of Chemistry|The Royal Society of Chemistry]] | date = 2014 | location = Cambridge | page = 722 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4| chapter = Front Matter }}</ref>
| SystematicName = (2''E'')-1,3-Diphenylprop-2-en-1-one
| SystematicName = (2''E'')-1,3-Diphenylprop-2-en-1-one
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}}
}}
}}
}}
'''Chalcone''' is the [[organic compound]] C<sub>6</sub>H<sub>5</sub>C(O)CH=CHC<sub>6</sub>H<sub>5</sub>. It is an [[Alpha-beta Unsaturated carbonyl compounds|α,β-unsaturated ketone]]. A variety of important biological compounds are known collectively as chalcones or [[chalconoid]]s.<ref>{{cite journal |doi=10.1002/(SICI)1097-0010(20000515)80:7<1073::AID-JSFA568>3.0.CO;2-B|title=Flavanones, Chalcones and Dihydrochalcones - Nature, Occurrence and Dietary Burden|year=2000|last1=Tomás-Barberán|first1=Francisco A.|last2=Clifford|first2=Michael N.|journal=Journal of the Science of Food and Agriculture|volume=80|issue=7|pages=1073–1080}}</ref>
'''Chalcone''' is the [[organic compound]] C<sub>6</sub>H<sub>5</sub>C(O)CH=CHC<sub>6</sub>H<sub>5</sub>. It is an [[Alpha-beta Unsaturated carbonyl compounds|α,β-unsaturated ketone]]. A variety of important biological compounds are known collectively as chalcones or [[chalconoid]]s.<ref>{{cite journal |doi=10.1002/(SICI)1097-0010(20000515)80:7<1073::AID-JSFA568>3.0.CO;2-B|title=Flavanones, Chalcones and Dihydrochalcones - Nature, Occurrence and Dietary Burden|year=2000|last1=Tomás-Barberán|first1=Francisco A.|last2=Clifford|first2=Michael N.|journal=Journal of the Science of Food and Agriculture|volume=80|issue=7|pages=1073–1080}}</ref> They are widely known bioactive substances, fluorescent materials, and chemical intermediates.


== Chemical properties ==
== Chemical properties ==
Chalcones have two absorption maxima at 280&nbsp;nm and 340&nbsp;nm.<ref>{{cite journal |doi=10.1016/S0925-3467(02)00220-3 |title=Photochemistry of chalcone and the application of chalcone-derivatives in photo-alignment layer of liquid crystal display |journal=Optical Materials |volume=21 |issue=1–3 |pages=667–71 |year=2003 |last1=Song |first1=Dong-mee |last2=Jung |first2=Kyoung-Hoon |last3=Moon |first3=Ji-hye |last4=Shin |first4=Dong-Myung |bibcode=2003OptMa..21..667S}}</ref>
Chalcones have two absorption maxima at 280&nbsp;nm and 340&nbsp;nm.<ref>{{cite journal |doi=10.1016/S0925-3467(02)00220-3 |title=Photochemistry of chalcone and the application of chalcone-derivatives in photo-alignment layer of liquid crystal display |journal=Optical Materials |volume=21 |issue=1–3 |pages=667–71 |year=2003 |last1=Song |first1=Dong-mee |last2=Jung |first2=Kyoung-Hoon |last3=Moon |first3=Ji-hye |last4=Shin |first4=Dong-Myung |bibcode=2003OptMa..21..667S}}</ref>


== Synthesis ==
==Biosynthesis==
⚫
Chalcones and [[chalconoids]] are synthesized in plants as [[secondary metabolite]]s. 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 plant|vascular]]) and several "lower" ([[non-vascular plant|non-vascular]]) plants.<ref name=zhuang_2017 />

==Laboratory synthesis ==
Chalcone is usually prepared by an [[aldol condensation]] between [[benzaldehyde]] and [[acetophenone]].<ref>{{cite journal |doi=10.15227/orgsyn.002.0001|title=Benzalacetophenone|journal=Organic Syntheses|year=1922|volume=2|page=1|author=E. P. Kohler, H. M. Chadwell}}</ref>
Chalcone is usually prepared by an [[aldol condensation]] between [[benzaldehyde]] and [[acetophenone]].<ref>{{cite journal |doi=10.15227/orgsyn.002.0001|title=Benzalacetophenone|journal=Organic Syntheses|year=1922|volume=2|page=1|author=E. P. Kohler, H. M. Chadwell}}</ref>
:[[Image:Chalcone preparation.svg|400px|preparation of chalcone]]
:[[Image:Chalcone preparation.svg|400px|preparation of chalcone]]


This reaction, which can be carried out without any solvent, is so reliable that it is used in as an example of [[green chemistry]] in undergraduate education.<ref>{{cite journal |doi=10.1021/ed081p1345 |title=Solvent-Free Synthesis of Chalcones |journal=Journal of Chemical Education |volume=81 |issue=9 |pages=1345 |year=2004 |last1=Palleros |first1=Daniel R |bibcode=2004JChEd..81.1345P }}</ref>
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.<ref>{{cite journal |doi=10.1021/ed081p1345 |title=Solvent-Free Synthesis of Chalcones |journal=Journal of Chemical Education |volume=81 |issue=9 |pages=1345 |year=2004 |last1=Palleros |first1=Daniel R |bibcode=2004JChEd..81.1345P }}</ref>

==Biosynthesis==
⚫
Chalcones and [[chalconoids]] are synthesized in plants as [[secondary metabolite]]s. 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 plant|vascular]]) and several "lower" ([[non-vascular plant|non-vascular]]) plants.<ref name=zhuang_2017 />


==Potential pharmacology==
==Potential pharmacology==
Chalcones and their derivatives demonstrate a wide range of biological activities including anti-inflammation.<ref name=pmid28914193>{{cite journal |doi=10.2174/1568026617666170914160446 |pmid=28914193 |title=Chalcone Derivatives: Anti-inflammatory Potential and Molecular Targets Perspectives |journal=Current Topics in Medicinal Chemistry |volume=17 |issue=28 |pages=3146–3169 |year=2017 |last1=Mahapatra |first1=Debarshi Kar |last2=Bharti |first2=Sanjay Kumar |last3=Asati |first3=Vivek }}</ref> Some 2′-amino chalcones have been studied as potential antitumor agents.<ref name="XiaYang2000">{{cite journal|last1=Xia|first1=Yi|last2=Yang|first2=Zheng-Yu|last3=Xia|first3=Peng|last4=Bastow|first4=Kenneth F.|last5=Nakanishi|first5=Yuka|last6=Lee|first6=Kuo-Hsiung|title=Antitumor agents. Part 202: Novel 2′-amino chalcones: design, synthesis and biological evaluation|journal=Bioorganic & Medicinal Chemistry Letters|volume=10|issue=8|year=2000|pages=699–701|issn=0960-894X|doi=10.1016/S0960-894X(00)00072-X|pmid=10782667}}</ref><ref name="SantosPinhanelli2017">{{cite journal|last1=Santos|first1=Mariana B.|last2=Pinhanelli|first2=Vitor C.|last3=Garcia|first3=Mayara A.R.|last4=Silva|first4=Gabriel|last5=Baek|first5=Seung J.|last6=França|first6=Suzelei C.|last7=Fachin|first7=Ana L.|last8=Marins|first8=Mozart|last9=Regasini|first9=Luis O.|title=Antiproliferative and pro-apoptotic activities of 2′- and 4′-aminochalcones against tumor canine cells|journal=European Journal of Medicinal Chemistry|volume=138|year=2017|pages=884–889|issn=0223-5234|doi=10.1016/j.ejmech.2017.06.049|pmid=28738308|url=https://repositorio.unesp.br/bitstream/11449/174929/1/2-s2.0-85024884865.pdf|hdl=11449/174929|hdl-access=free}}</ref> Chalcones are of interest in [[medicinal chemistry]] and have been described as a [[privileged scaffold]].<ref name="zhuang_2017">{{cite journal |last1=Zhuang |first1=Chunlin |last2=Zhang |first2=Wen |last3=Sheng |first3=Chunquan |last4=Zhang |first4=Wannian |last5=Xing |first5=Chengguo |last6=Miao |first6=Zhenyuan |title=Chalcone: A Privileged Structure in Medicinal Chemistry |journal=Chemical Reviews |date=28 June 2017 |volume=117 |issue=12 |pages=7762–7810 |doi=10.1021/acs.chemrev.7b00020|pmc=6131713 }}</ref>
Chalcones and their derivatives demonstrate a wide range of biological activities including anti-inflammation.<ref name=pmid28914193>{{cite journal |doi=10.2174/1568026617666170914160446 |pmid=28914193 |title=Chalcone Derivatives: Anti-inflammatory Potential and Molecular Targets Perspectives |journal=Current Topics in Medicinal Chemistry |volume=17 |issue=28 |pages=3146–3169 |year=2017 |last1=Mahapatra |first1=Debarshi Kar |last2=Bharti |first2=Sanjay Kumar |last3=Asati |first3=Vivek }}</ref> Some 2′-amino chalcones have been studied as potential antitumor agents.<ref name="XiaYang2000">{{cite journal|last1=Xia|first1=Yi|last2=Yang|first2=Zheng-Yu|last3=Xia|first3=Peng|last4=Bastow|first4=Kenneth F.|last5=Nakanishi|first5=Yuka|last6=Lee|first6=Kuo-Hsiung|title=Antitumor agents. Part 202: Novel 2′-amino chalcones: design, synthesis and biological evaluation|journal=Bioorganic & Medicinal Chemistry Letters|volume=10|issue=8|year=2000|pages=699–701|issn=0960-894X|doi=10.1016/S0960-894X(00)00072-X|pmid=10782667}}</ref><ref name="SantosPinhanelli2017">{{cite journal|last1=Santos|first1=Mariana B.|last2=Pinhanelli|first2=Vitor C.|last3=Garcia|first3=Mayara A.R.|last4=Silva|first4=Gabriel|last5=Baek|first5=Seung J.|last6=França|first6=Suzelei C.|last7=Fachin|first7=Ana L.|last8=Marins|first8=Mozart|last9=Regasini|first9=Luis O.|title=Antiproliferative and pro-apoptotic activities of 2′- and 4′-aminochalcones against tumor canine cells|journal=European Journal of Medicinal Chemistry|volume=138|year=2017|pages=884–889|issn=0223-5234|doi=10.1016/j.ejmech.2017.06.049|pmid=28738308|url=https://repositorio.unesp.br/bitstream/11449/174929/1/2-s2.0-85024884865.pdf|hdl=11449/174929|hdl-access=free}}</ref> Chalcones are of interest in [[medicinal chemistry]] and have been described as a [[privileged scaffold]].<ref name="zhuang_2017">{{cite journal |last1=Zhuang |first1=Chunlin |last2=Zhang |first2=Wen |last3=Sheng |first3=Chunquan |last4=Zhang |first4=Wannian |last5=Xing |first5=Chengguo |last6=Miao |first6=Zhenyuan |title=Chalcone: A Privileged Structure in Medicinal Chemistry |journal=Chemical Reviews |date=28 June 2017 |volume=117 |issue=12 |pages=7762–7810 |doi=10.1021/acs.chemrev.7b00020|pmid=28488435 |pmc=6131713 }}</ref>

==Uses==
===Medicinal uses===
In [[medicinal chemistry]], chalcones have been used as:
*[[antioxidant]]s
*[[Anticancer agent]]s
*[[antidiabetic drug]]s
*[[antiviral drug]]s
*[[antimalarial drug]]s and more.

===Industrial uses===
In chemical industries, they are employed as:
*[[liquid crystal]]s
*[[fluorescent]] [[scaffold (chemistry)|chemical scaffold]]s
*[[metal sensor]]s
*[[corrosion inhibitor]]s
*[[plant hormone]]s.<ref>{{Cite journal |last1=Nayak |first1=Yogeesha N. |last2=Gaonkar |first2=Santosh L. |last3=Sabu |first3=Mariya |date=2023-01-04 |title=Chalcones: Versatile intermediates in heterocyclic synthesis |url=https://onlinelibrary.wiley.com/doi/10.1002/jhet.4617 |journal=Journal of Heterocyclic Chemistry |language=en |pages=jhet.4617 |doi=10.1002/jhet.4617 |s2cid=255212828 |issn=0022-152X}}</ref>

===Uses in organic chemistry===
Chalcones have been used as intermediates in heterocyclic synthesis, especially in the synthesis of [[pyrazole]]s and [[aurone]]s.<ref>{{Cite journal |last1=Nayak |first1=Yogeesha N. |last2=Gaonkar |first2=Santosh L. |last3=Sabu |first3=Mariya |date=2023-01-04 |title=Chalcones: Versatile intermediates in heterocyclic synthesis |url=https://onlinelibrary.wiley.com/doi/10.1002/jhet.4617 |journal=Journal of Heterocyclic Chemistry |language=en |pages=jhet.4617 |doi=10.1002/jhet.4617 |s2cid=255212828 |issn=0022-152X}}</ref>


==See also==
==See also==

Latest revision as of 23:03, 27 June 2023

For the butterflies, see Chalcone (skipper).
Chalcone[1]
Skeletal formula of chalcone
Ball-and-stick model of the chalcone molecule
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
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.002.119 Edit this at Wikidata
UNII
  • InChI=1S/C15H12O/c16-15(14-9-5-2-6-10-14)12-11-13-7-3-1-4-8-13/h1-12H checkY
    Key: DQFBYFPFKXHELB-UHFFFAOYSA-N checkY
  • 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
  • O=C(C=Cc1ccccc1)c2ccccc2
Properties
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)
-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 checkY☒N ?)

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]

preparation of chalcone

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:

Industrial uses[edit]

In chemical industries, they are employed as:

Uses in organic chemistry[edit]

Chalcones have been used as intermediates in heterocyclic synthesis, especially in the synthesis of pyrazoles and aurones.[12]

See also[edit]

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. ^ 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.
  12. ^ 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]

source: https://en.wikipedia.org/w/index.php?title=Chalcone&diff=1162252483&oldid=1075974429

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