{{For|the butterfly genus|Chalcone (butterfly)}} {{chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 443514088 | Name = Chalcone<ref>''Merck Index'', 11th Edition, '''2028'''</ref> | ImageFile = Chalcone.svg | ImageSize = 180 | ImageAlt = Skeletal formula of chalcone | ImageFile1 = Chalcone 3D ball.png | ImageSize1 = 220 | 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 = 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 | 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. |Section1={{Chembox Identifiers | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 6921 | InChIKey = DQFBYFPFKXHELB-UHFFFAOYAP | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C15H12O/c16-15(14-9-5-2-6-10-14)12-11-13-7-3-1-4-8-13/h1-12H | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = DQFBYFPFKXHELB-UHFFFAOYSA-N | CASNo = 94-41-7 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 5S5A2Q39HX | CASNo2 = 614-47-1 | CASNo2_Ref = {{cascite|correct|CAS}} | CASNo2_Comment = ((''E'')-Chalcone) | PubChem = 637760 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 27618 | SMILES = O=C(C=Cc1ccccc1)c2ccccc2 | InChI = 1/C15H12O/c16-15(14-9-5-2-6-10-14)12-11-13-7-3-1-4-8-13/h1-12H | MeSHName = }} |Section2={{Chembox Properties | C=15 | H=12 | O=1 | Appearance = pale yellow solid | Density =1.071 g/cm<sup>3</sup> | MeltingPtC = 55 to 57 | MeltingPt_notes = | BoilingPtC = 345 to 348 | Solubility = | MagSus = −125.7·10<sup>−6</sup> cm<sup>3</sup>/mol }} }} '''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 α,β-unsaturated ketone. A variety of important biological compounds are known collectively as chalcones or chalconoids.<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 |bibcode=2000JSFA...80.1073T }}</ref> They are widely known bioactive substances, fluorescent materials, and chemical intermediates.

== 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>

==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.<ref name=zhuang_2017 />

==Laboratory synthesis == Chalcone is usually prepared by an aldol condensation between benzaldehyde and acetophenone. <ref>{{cite journal |last1=Sîrbu |first1=Dumitru |last2=Marin |first2=Ion |title=Synthesis and IR, NMR caracterisation of new p-(N,N-diphenylamino) chalcones |journal=Chemistry Journal of Moldova. General, Industrial and Ecological Chemistry |year=2011 |volume=6 |issue=1 |pages=86–89 }}</ref> <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> :400px|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.<ref>{{cite journal |doi=10.1021/ed081p1345 |title=Solvent-Free Synthesis of Chalcones |journal=Journal of Chemical Education |volume=81 |issue=9 |page=1345 |year=2004 |last1=Palleros |first1=Daniel R |bibcode=2004JChEd..81.1345P }}</ref>

==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|pmid=28488435 |pmc=6131713 }}</ref>

==Uses== ===Medicinal uses=== In medicinal chemistry, chalcones have been used as: *antioxidants *anticancer agents *antidiabetic drugs *antiviral drugs *antimalarial drugs

===Industrial uses=== In chemical industries, they are employed as: *liquid crystals *fluorescent chemical scaffolds *metal sensors *corrosion inhibitors *plant hormones<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 |volume=60 |issue=8 |language=en |article-number=jhet.4617 |doi=10.1002/jhet.4617 |s2cid=255212828 |issn=0022-152X|url-access=subscription }}</ref>

===Uses in organic chemistry=== Chalcones have been used as intermediates in heterocyclic synthesis, especially in the synthesis of pyrazoles and aurones.<ref name=Nayak/>

In the Johnson–Corey–Chaykovsky reaction, chalcone reacts with dimethylsulfoxonium methylide to give 1-phenyl-2-benzoylcyclopropane [15295-43-9] [1145-91-1] in 95% yield.<ref>{{cite journal |author=Corey, E. J. |author2=Chaykovsky, Michael. | journal=Journal of the American Chemical Society | title=Dimethylsulfoxonium Methylide | volume=84 | issue=5 | pages=867–868 | date= March 1962 | doi=10.1021/ja00864a040 | bibcode=1962JAChS..84..867C }}</ref> A Leuckart reaction or ammonium acetate in the presence of sodium cyanoborohydride would be predicted to give Phenyl(2-phenylcyclopropyl)methanamine [1559116-96-9]. Alternatively if a reductive amination of the ketone with methylamine is performed one would instead get the secondary amine N-Me [1559367-56-4]. center|500px|Corey's tranylcypromine These compounds have the same ''trans''-stereochemistry as was observed for tranylcypromine although their exact mode of pharmacology is still lacking. Lastly, it was discovered that if a hydrazine is prepared from the ketone (ala pheniprazine) one gets a compound that is called [Phenyl-(2-phenylcyclopropyl)methyl]hydrazine ([https://pubchem.ncbi.nlm.nih.gov/compound/105199424 PC105199424]).

==See also== * Juliá–Colonna epoxidation

==References== {{reflist}}

==External links== * [http://www.reference.md/files/D047/mD047188.html Chalcone on reference.md] {{Webarchive|url=https://web.archive.org/web/20200925011431/http://www.reference.md/files/D047/mD047188.html |date=2020-09-25 }}

Category:Chalconoids Category:Phenyl compounds Category:Enones