SOLVENT FREE SYNTHESIS OF CHALCONE AS ANTIBACTERIAL SUBSTANCE

Susy Yunita Prabawati, Arifah Khusnuryani, Khamidinal Khamidinal

Abstract

The aims of this study was to synthesize a compound of 3-methoxy-4-hydroxychalcone through Claisen-Schmidt condensation with grinding technique (solvent-free). Vanillin, acetophenone and 60 % NaOH catalyst used in this synthesis. Characterization of products was done with a spectrophotometer FTIR and 1H-NMR spectrometer. The  product was obtained as a orange solid which has a melting point at    58 - 59 ˚C. Identification of the product by IR spectrophotometer showed the absorption of  C=C in the wavenumber of 1496.76 cm-1 which confirmed that the hydration reaction of chalcone had occurred. Analysis using 1H-NMR spectrometer also showed the proton of the CH=CH appearing on chemical shift (δ) 7.99 ppm. The antibacterial activity test showed that the compounds of 3-methoxy-4- hydroxychalcone has a potential as an antibacterial against bacteria E. coli and B. subtilis.

Keywords

antibacterial; grinding technique; vanillin; 3-methoxy-4-hydroxychalcone

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References

Achanta, G., Modzelewska, A., Feng, L., Khan, S.R., and Huang, P., 2006. Boronic-chalcone derivative exhibits potent anticancer activity through inhibition of the proteasome. Molecular pharmacology 70, 426-433.

Cappuccino, J.G., and Sherman, N., 2011. Microbiology: a laboratory manual. 9 Edition. SUNY Rockland Community College, New York.

Dwi, R.H., 2014. Optimasi Sintesis Senyawa 3-metoksi-4-hidroksikalkon pada Variasi Konsentrasi Katalis dan Waktu Reaksi Menggunakan Bahan Dasar Vanilin. Skripsi. UIN Sunan Kalijaga: Yogyakarta.

Eryanti, Y., Zamri, A., Jasril, Rahmita., 2010. Sintesis Turunan 2’-hidroksi Kalkon melalui Kondensasi Claisen-Schmidt dan Uji Aktivitasnya sebagai Antimikroba. Jurnal Natur Indonesia 12 (2), 223-227.

Faridz, M.B.O., 2009. Sintesis kalkon bebas Pelarut daripada Kondensasi Aldol dimangkinkan oleh Pejajal natrium Hidroksida (NaOH). Skripsi. Universiti Teknologi MARA.

Fitri, A.Y., 2013. Penggunaan Hidroksi sitronelal Kaliks [4] Resorsinarena Untuk Adsorpsi Kation Logam Berat Pb(II), Cd(II), da Cu(II). Skripsi. Universitas Pendidikan Indonesia: Bandung.

Jasril, Teruna, H.Y., Zamri, A., Alfatos, D., Yuslinda, E., and Nurulita, Y., 2012. Sintesis dan Uji Antibakteri Senyawa Bromo Kalkon Piridin. Jurnal Natur Indonesia 14 (3), 172-175.

Jia, X., Li, J., D, Y., Zhang, B., Wang, N., and Wang, Y., 2013. A simple and green protocol for 2H-Indalazo [2,1-b] htalazine-triones Using Grinding Method. Journal of Chemistry 2013, 1-5. doi:10.1155/2013/634510

Kim, B.T., O, K., Chun, J.C and Hwang, K.J., 2008. Synthesis of dihydroxylated chalcone derivatives with diverse substitution patterns and their radical scavenging ability toward DPPH free radicals. Bulletin of the Korean Chemical Society 29 (6), 1125-1130.

Kim, Y.H., Kim, J., Park, H and Kim, H.P., 2007. Anti-inflammatory activity of the synthetic chalcone derivative: inhibition of inducible nitric oxide synthase-catalyzed nitric oxide production from lipopoly saccharide-treated raw 264.7 cells. Biological & Pharmaceutical Bulletin 30 (8), 1450-1455.

Lahtchev, K.L., Batovska, D.I., Parushev, St.P., Ubiyvovk, V.M., and Sibirny, A.A., 2008. Antifungal activity of chalcones: A mechanistic study using various yeast strains. European Journal of Medicinal Chemistry 43, 2220-2228.

Palleros, D.R., 2004. Experimental Organic Chemistry. John Wiley & Sons, New York.

Prasad, Y.R., Kumar, P.P., Kumar, P.R., and Rao, A.S., 2008. Synthesis and Antimicrobial activity of some new chalcones of 2-acetyl pyridine. Journal of Chemistry 5, 144-148.

Saxena, S., and Gomber, C., 2008. Comparative in vitro Antimicrobial Procedural Efficacy for Susceptibility of Staphylococcus aureus, Escherichia coli and Pseudomonas species to Chloramphenicol, Ciprofloxacin and Cefaclor. British Journal of Biochemical Science 65:178-183.

Susanti, E.V.H., Matsjeh, S., Tutik, T.D., and Mustofa, 2012. Sintesis 2’,6’-dihidroksi-3,4-dimetoksikalkon Melalui Kondensasi Claisen-Schmidt dengan Teknik Grinding. Prosiding Seminar Nasional Kimia. Jurusan Pendidikan Kimia FMIPA UNY, 3 November 2012.

DOI: https://doi.org/10.20961/alchemy.13.1.4324.95-102

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