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:''For the genus of grass skipper butterflies, see '']. |
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{{for|the butterflies|Chalcone (skipper)}} |
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{{chembox |
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{{chembox |
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| Verifiedfields = changed |
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| verifiedrevid = 443512620 |
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| Watchedfields = changed |
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| Name = Chalcone<ref>''Merck Index'', 11th Edition, '''2028'''.</ref> |
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| verifiedrevid = 443514088 |
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| ImageFile = Chalcone.svg |
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| Name = Chalcone<ref>''Merck Index'', 11th Edition, '''2028'''</ref> |
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| IUPACName= 1,3-Diphenyl-2-propen-1-one |
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| ImageFile = Chalcone.svg |
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| OtherNames=Chalcone<br />Chalkone<br />Benzylideneacetophenone<br />Phenyl styryl ketone |
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| ImageSize = 180 |
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|Section1= {{Chembox Identifiers |
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| ImageAlt = Skeletal formula of chalcone |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ImageFile1 = Chalcone 3D ball.png |
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| ImageSize1 = 220 |
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| ImageAlt1 = Ball-and-stick model of the chalcone molecule |
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| ImageFile2 = |
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| PIN = Chalcone<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = ] | date = 2014 | location = Cambridge | page = 722 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4| chapter = Front Matter }}</ref> |
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| SystematicName = (2''E'')-1,3-Diphenylprop-2-en-1-one |
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| OtherNames = Chalkone<br />Benzylideneacetophenone<br />Phenyl styryl ketone<br />benzalacetophenone<br /> ''β''-phenylacrylophenone<br />''γ''-oxo-''α'',''γ''-diphenyl-''α''-propylene<br /> ''α''-phenyl-''β''-benzoylethylene. |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 6921 |
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| ChemSpiderID = 6921 |
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| InChIKey = DQFBYFPFKXHELB-UHFFFAOYAP |
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| InChIKey = DQFBYFPFKXHELB-UHFFFAOYAP |
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| StdInChIKey = DQFBYFPFKXHELB-UHFFFAOYSA-N |
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| StdInChIKey = DQFBYFPFKXHELB-UHFFFAOYSA-N |
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| CASNo = 94-41-7 |
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| CASNo = 94-41-7 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 5S5A2Q39HX |
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| CASOther = <br/>614-47-1 ((''E'')-Chalcone) |
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| PubChem = 637760 |
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| CASNo2 = 614-47-1 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| CASNo2_Ref = {{cascite|correct|CAS}} |
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| CASNo2_Comment = ((''E'')-Chalcone) |
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| PubChem = 637760 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 27618 |
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| ChEBI = 27618 |
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| SMILES = O=C(C=Cc1ccccc1)c2ccccc2 |
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| SMILES = O=C(C=Cc1ccccc1)c2ccccc2 |
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| InChI = 1/C15H12O/c16-15(14-9-5-2-6-10-14)12-11-13-7-3-1-4-8-13/h1-12H |
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| InChI = 1/C15H12O/c16-15(14-9-5-2-6-10-14)12-11-13-7-3-1-4-8-13/h1-12H |
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| MeSHName = |
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}} |
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|Section2= {{Chembox Properties |
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| C=15|H=12|O=1 |
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| MolarMass =208.26 g/mol |
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| ExactMass = 208.088815 |
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| Appearance= |
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| Density=1.071 g/cm<sup>3</sup> |
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| MeltingPt=55–57 °C |
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| BoilingPt = 345-348 °C |
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| Solubility= |
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}} |
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}} |
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|Section2={{Chembox Properties |
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| C=15 | H=12 | O=1 |
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| Appearance = pale yellow solid |
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| Density =1.071 g/cm<sup>3</sup> |
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| MeltingPtC = 55 to 57 |
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| MeltingPt_notes = |
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| BoilingPtC = 345 to 348 |
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| Solubility = |
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| MagSus = -125.7·10<sup>−6</sup> cm<sup>3</sup>/mol |
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'''Chalcone''' is the ] C<sub>6</sub>H<sub>5</sub>C(O)CH=CHC<sub>6</sub>H<sub>5</sub>. It is an ]. A variety of important biological compounds are known collectively as chalcones or ]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. |
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'''Chalcone''' is an ] ] and an ] that forms the central core for a variety of important biological compounds, which are known collectively as chalcones or ]s. |
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==Chemical synthesis== |
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== Chemical properties == |
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Chalcones have two absorption maxima at 280 nm and 340 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> |
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Chalcones can be prepared by an ] between a ] and an ] in the presence of ] as a ]. |
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==Biosynthesis== |
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Chalcones and ] are synthesized in plants as ]s. The enzyme ], a type III ], is responsible for the ] of these compounds. The enzyme is found in all "higher" (]) and several "lower" (]) plants.<ref name=zhuang_2017 /> |
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==Laboratory synthesis == |
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This reaction has been found to work without any solvent at all - a ] reaction.<ref>Toda, F., et al., '']'', '''1990''', 3207.</ref> The reaction between substituted benzaldehydes and acetophenones has been used to demonstrate ] in undergraduate chemistry education.<ref>Palleros, D. R., '']'', '''81''', 1345 (2004).</ref> In a study investigating green chemistry synthesis, chalcones were also synthesized from the same starting materials in high temperature water (200 to 350 °C).<ref>Comisar, C. M. and Savage, P. E. ], '''6''' (2004), 227 - 231. {{DOI|10.1039/b314622g}}</ref> |
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Chalcone is usually prepared by an ] between ] and ].<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> |
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:] |
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This reaction, which can be carried out without any solvent, is so reliable that it is often given as an example of ] 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> |
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==Chemical reactions== |
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An example is the ] of chalcone by ] <ref>{{cite journal|doi=10.1016/S0040-4039(00)72405-1|title=Reaction of organotin hydrides with α,β-unsaturated ketones|year=1966|last1=Leusink|first1=A.J.|last2=Noltes|first2=J.G.|journal=Tetrahedron Letters|volume=7|pages=2221|issue=20}}</ref>: |
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==Potential pharmacology== |
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{| class="wikitable" |
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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 ] and have been described as a ].<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> |
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! Conjugate reduction chalcone |
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==Uses== |
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An asymmetric version of this reaction has also been developed <ref>{{cite journal|doi=10.1021/ja0009525|title=Synthesis of β-Alkyl Cyclopentanones in High Enantiomeric Excess via Copper-Catalyzed Asymmetric Conjugate Reduction|year=2000|last1=Moritani|first1=Yasunori|last2=Appella|first2=Daniel H.|last3=Jurkauskas|first3=Valdas|last4=Buchwald|first4=Stephen L.|journal=Journal of the American Chemical Society|volume=122|pages=6797|issue=28}}</ref>. |
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===Medicinal uses=== |
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In ], chalcones have been used as: |
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*]s |
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*]s |
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*]s |
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*]s |
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*]s and more. |
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===Industrial uses=== |
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In chemical industries, they are employed as: |
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*]s |
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*] ]s |
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*]s |
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*]s |
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*]s.<ref name=Nayak>{{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> |
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===Uses in organic chemistry=== |
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Chalcones have been used as intermediates in heterocyclic synthesis, especially in the synthesis of ]s and ]s.<ref name=Nayak/> |
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==See also== |
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==See also== |
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* ] |
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* ] |
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==References== |
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==References== |
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{{reflist}} |
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<references/> |
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==External links== |
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==External links== |
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* {{Webarchive|url=https://web.archive.org/web/20200925011431/http://www.reference.md/files/D047/mD047188.html |date=2020-09-25 }} |
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