Kalkon

Kalkon^[1]
Nama
	Nama IUPAC (preferensi) Kalkon
	Nama IUPAC (sistematis) (2E)-1,3-Difenilprop-2-en-1-ona
	Nama lain Benzilideneasetofenon; Fenil stiril keton; benzalasetofenon; β-fenilakrilofenon; γ-okso-α,γ-difenil-α-propilen; α-fenil-β-benzoiletilena.
Penanda
Nomor CAS	94-41-7; 614-47-1 ((E)-Chalcone) ;
Model 3D (JSmol)	Gambar interaktif;
3DMet	{{{3DMet}}}
ChEBI	CHEBI:27618 ;
ChemSpider	6921 ;
Nomor EC
PubChem CID	637760;
Nomor RTECS	{{{value}}}
UNII	5S5A2Q39HX ;
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 Key: DQFBYFPFKXHELB-UHFFFAOYSA-N ; 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;
Sifat
Rumus kimia	C15H12O
Massa molar	208,26 g·mol−1
Penampilan	Padat kuning pucat
Densitas	1.071 g/cm3
Titik lebur	55 hingga 57 °C (131 hingga 135 °F; 328 hingga 330 K)
Titik didih	345 hingga 348 °C (653 hingga 658 °F; 618 hingga 621 K)
Suseptibilitas magnetik (χ)	-125.7·10−6 cm3/mol
	Kecuali dinyatakan lain, data di atas berlaku pada suhu dan tekanan standar (25 °C [77 °F], 100 kPa).
	verifikasi (apa ini ?)
	Referensi

Kalkon adalah senyawa organik dengan rumus kimia C₆H₅C(O)CH=CHC₆H₅. Senyawa ini merupakan keton tak jenuh α,β. Berbagai senyawa biologis penting dikenal secara kolektif sebagai kalkon atau kalkonoid.^[3] Mereka merupakan zat bioaktif, bahan fluoresen, dan zat intermediat kimia yang dikenal luas.

Sifat kimia

Kalkon memiliki dua serapan maksimum pada 280 nm dan 340 nm.^[4]

Biosintesis

Kalkon dan kalkonoid disintesis pada tumbuhan sebagai metabolit sekunder. Enzim kalkon sintase, suatu poliketida sintase tipe III, bertanggung jawab atas biosintesis senyawa ini. Enzim ini ditemukan di semua tumbuhan "tingkat tinggi" (tumbuhan berpembuluh) dan beberapa tumbuhan "bawah" (tumbuhan tidak berpembuluh).^[5]

Sintesis laboratorium

Kalkon biasanya dibuat melalui kondensasi aldol antara benzaldehida dan asetofenon.^[6]

Reaksi ini, yang dapat dilakukan tanpa pelarut apa pun, sangat andal sehingga sering dijadikan contoh kimia hijau dalam pendidikan sarjana.^[7]

Farmakologi potensial

Kalkon dan turunannya menunjukkan berbagai aktivitas biologis termasuk antiinflamasi.^[8] Beberapa kalkon 2′-amino telah dipelajari sebagai agen antitumor yang potensial.^[9]^[10] Kalkon sangat menarik dalam bidang kimia medisinal dan telah digambarkan sebagai perancah istimewa.^[5]

Kegunaan

Kimia Medis

Antioksidan
Agen antikanker
Obat antidiabetik
Obat antivirus
Obat antimalaria dan banyak lagi.

Kimia Industri

Kristal cair
Perancah kimia fluoresensi
sensor logam
Penghambat korosi
Hormon tumbuhan.^[11]

Kimia Organik

Kalkon telah digunakan sebagai perantara dalam sintesis heterosiklik, terutama dalam sintesis pirazol dan auron.^[12]

Referensi

^ Merck Index, 11th Edition, 2028
^ "Front Matter". Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. hlm. 722. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
^ 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.
^ 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.
^ ^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.
^ E. P. Kohler, H. M. Chadwell (1922). "Benzalacetophenone". Organic Syntheses. 2: 1. doi:10.15227/orgsyn.002.0001.
^ Palleros, Daniel R (2004). "Solvent-Free Synthesis of Chalcones". Journal of Chemical Education. 81 (9): 1345. Bibcode:2004JChEd..81.1345P. doi:10.1021/ed081p1345.
^ 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.
^ 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.
^ 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.
^ Nayak, Yogeesha N.; Gaonkar, Santosh L.; Sabu, Mariya (2023-01-04). "Chalcones: Versatile intermediates in heterocyclic synthesis". Journal of Heterocyclic Chemistry (dalam bahasa Inggris): jhet.4617. doi:10.1002/jhet.4617. ISSN 0022-152X.
^ Nayak, Yogeesha N.; Gaonkar, Santosh L.; Sabu, Mariya (2023-01-04). "Chalcones: Versatile intermediates in heterocyclic synthesis". Journal of Heterocyclic Chemistry (dalam bahasa Inggris): jhet.4617. doi:10.1002/jhet.4617. ISSN 0022-152X.

Pranala Luar

Chalcone on reference.md Diarsipkan 2020-09-25 di Wayback Machine.

[1] Merck Index, 11th Edition, 2028

[iupac2013-2] "Front Matter". Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. hlm. 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.

[zhuang_2017-5] 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.

[pmid28914193-8] 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.

[XiaYang2000-9] 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.

[SantosPinhanelli2017-10] 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 (dalam bahasa Inggris): jhet.4617. doi:10.1002/jhet.4617. ISSN 0022-152X.

[12] Nayak, Yogeesha N.; Gaonkar, Santosh L.; Sabu, Mariya (2023-01-04). "Chalcones: Versatile intermediates in heterocyclic synthesis". Journal of Heterocyclic Chemistry (dalam bahasa Inggris): jhet.4617. doi:10.1002/jhet.4617. ISSN 0022-152X.

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