Synthesis of Dibenzalacetone using Sonochemistry and Its Antibacterial Activity Against Escherichia coli

Yuliana Purwaningsih; Erwin Indriyanti; Mighfar Syukur; Dyan Wigati

doi:10.20961/jkpk.v8i3.65172

Synthesis of Dibenzalacetone using Sonochemistry and Its Antibacterial Activity Against Escherichia coli

Yuliana Purwaningsih, Erwin Indriyanti, Mighfar Syukur, Dyan Wigati

Abstract

The synthesis of dibenzalacetone, a ketone compound with potential antibacterial properties, especially against Escherichia coli, has typically involved time-consuming methods. This study adopts sonochemistry, an increasingly popular technique recognized for its efficiency and quick yield. The aim is to synthesize dibenzalacetone using the sonochemical method and evaluate its antibacterial efficacy against E. coli. The synthesis process includes a cross-aldol condensation reaction between acetone and benzaldehyde, catalyzed by NaOH, conducted in an ultrasonic bath at 35 °C for 1-5 minutes. The optimal synthesis condition, achieved in 4 minutes, resulted in a 76.56% yield of dibenzalacetone, characterized as a bright yellow solid with a melting point of 111-114°C. Techniques such as FT-IR, GC-MS, 1H-NMR, and 13C-NMR spectrometry were employed for structural characterization. The FTIR analysis revealed various functional groups, including C=O ketone, C=C aromatic, and C-H aromatic. GC-MS data confirmed the molecular weight of dibenzalacetone at m/z 234.1. Furthermore, ¹H-NMR and ¹³C-NMR analyses provided detailed insights into the compound's chemical shifts and structural groups, affirming the successful synthesis of dibenzalacetone. The antibacterial activity of dibenzalacetone against E. coli was tested at concentrations ranging from 5% to 20%. Notably, at a 15% concentration, dibenzalacetone exhibited antibacterial activity comparable to amoxicillin. These findings suggest that dibenzalacetone, efficiently synthesized via sonochemistry, not only achieves a high yield but also has potential as an antibacterial agent against E. coli. This research highlights the efficacy of sonochemistry for the rapid and effective synthesis of compounds with significant medical applications.

Keywords

Antibacterial; Dibenzalacetone; Escherichia coli; Green synthesis; Sonochemistry

Full Text:

PDF

References

[1] F. Prestinaci, P. Pezzotti, and A. Pantosti, “Antimicrobial resistance: A global multifaceted phenomenon,” Pathog. Glob. Health, vol. 109, no. 7, pp. 309–318, 2015,

doi: 10.1179/2047773215Y.0000000030.

[2] S. B. Levy and M. Bonnie, “Antibacterial resistance worldwide: Causes, challenges and responses,” Nat. Med., vol. 10, no. 12S, pp. S122–S129, 2004,

doi: 10.1038/nm1145.

[3] M. Terreni, M. Taccani, and M. Pregnolato, “New antibiotics for multidrug-resistant bacterial strains: Latest research developments and future perspectives,” Molecules, vol. 26, no. 9, 2021,

doi: 10.3390/molecules26092671.

[4] R. Watpade, P. Tandale, M. Shinde, P. Dhondge, and R. Toche, “Synthesis, characterization of β- amino ketone complexes and Study of their antibacterial activity,” Der Pharm. Lett., vol. 8, no. 11, pp. 124–127, 2016.

Google Scholar

[5] L. Hellewell and S. Bhakta, “Chalcones, stilbenes and ketones have anti-infective properties via inhibition of bacterial drug-efflux and consequential synergism with antimicrobial agents,” Access Microbiol., vol. 2, no. 4, 2020,

doi: 10.1099/acmi.0.000105.

[6] M. De Los Angeles Alvarez, V. E. P. Zarelli, N. B. Pappano, and N. B. Debattista, “Bacteriostatic action of synthetic polyhydroxylated chalcones against Escherichia coli,” Biocell, vol. 28, no. 1, pp. 31–34, 2004,

doi: 10.32604/biocell.2004.28.031.

[7] G. Araya et al., “Inhibition of Escherichia coli and Bacillus subtilis FtsZ polymerization and bacillus subtilis growth by dihydroxynaphtyl aryl ketones,” Front. Microbiol., vol. 10, no. JUN, pp. 1–9, 2019,

doi: 10.3389/fmicb.2019.01225.

[8] O. Houshia et al., “Assessment of the Ratio of Geometric Isomers of Dibenzalacetone Spectroscopically,” J. Pharm. Res. Int., vol. 31, no. 4, pp. 1–9, 2019,

doi: 10.9734/jpri/2019/v31i430307.

[9] S. Handani and I. S. Arty, “Synthesis of Hydroxyl Radical Scavengers from Benzalacetone and its Derivatives,” J. Phys. Sci., vol. 19, no. 2, pp. 61–68, 2008.

Google Scholar

[10] I. S. Chauhan, G. S. Rao, J. Shankar, L. K. S. Chauhan, G. J. Kapadia, and N. Singh, “Chemoprevention of Leishmaniasis: In-vitro antiparasitic activity of dibenzalacetone, a synthetic curcumin analog leads to apoptotic cell death in Leishmania donovani,” Parasitol. Int., vol. 67, no. 5, pp. 627–636, 2018,

doi: 10.1016/j.parint.2018.06.004.

[11] A. F. M. M. Rahman, R. Ali, Y. Jahng, and A. A. Kadi, “A facile solvent free claisen-schmidt reaction: Synthesis of α,α’-bis-(Substituted-benzylidene)cycloalkanones and α,α’-bis-(Substituted-alkylidene)cycloalkanones,” Molecules, vol. 17, no. 1, pp. 571–583, 2012,

doi: 10.3390/molecules17010571.

[12] S. Handayani, S. Matsjeh, C. Anwar, S. Atun, and I. Fatimah, “Novel Synthesis of 1 , 5-dibenzalacetone using NaOH/ZrO₂ Montmorillonite as Cooperative Catalyst,” Int. J. Chem. Anal. Sci., vol. 3, no. 6, pp. 6–10, 2012.

Google Scholar

[13] M. Draye, G. Chatel, and R. Duwald, “Ultrasound for drug synthesis: A green approach,” Pharmaceuticals, vol. 13, no. 2, 2020,

doi: 10.3390/ph13020023.

[14] M. A. Mohamed, “Sonochemistry (Applications of Ultrasound in Chemical Synthesis and Reactions): A Review Part III,” J. Pharm. Res. Int., vol. 31, no. 6, pp. 1–19, 2019,

doi: 10.9734/jpri/2019/v31i630363.

[15] S. D. Gawas and V. K. Rathod, “Ultrasound assisted green synthesis of 2-ethylhexyl stearate: A cosmetic bio-lubricant,” J. Oleo Sci., vol. 69, no. 9, pp. 1043–1049, 2020,

doi: 10.5650/jos.ess19322.

[16] D. Vassilev, N. Petkova, M. Koleva, and P. Denev, “Ultrasound-assisted method for the synthesis of tertiary fatty aliphatic esters with potential antimicrobial activity,” Biointerface Res. Appl. Chem., vol. 10, no. 6, pp. 6829–6836, 2020,

doi: 10.33263/BRIAC106.68296836.

[17] Y. Purwaningsih, M. Syukur, U. Rizki, and E. Purwanto, “Sonochemical Synthesis of Ethyl Cinnamate,” JKPK (JURNAL Kim. DAN Pendidik. Kim., vol. 5, no. 1, pp. 1–7, 2020,

doi: 10.20961/jkpk.v5i1.35525.

[18] N. Sharma, P. Kumari, P. Sharma, N. Bhagat, and S. Bhagat, “Ultrasound-Accelerated Amide Coupling Reactions Directed toward the Synthesis of 1-Acetyl-3-carboxamide-β-carboline Derivatives of Biological Importance,” SynOpen, vol. 01, no. 01, pp. 0008–0010, 2017,

doi: 10.1055/s-0036-1588167.

[19] A. A. T. Suma, T. D. Wahyuningsih, and Mustofa, “Efficient synthesis of chloro chalcones under ultrasound irradiation, their anticancer activities and molecular docking studies,” Rasayan J. Chem., vol. 12, no. 2, pp. 502–510, 2019,

doi: 10.31788/RJC.2019.1225020.

[20] G. Cravotto, A. Demetri, G. M. Nano, G. Palmisano, A. Penoni, and S. Tagliapietra, “The Aldol Reaction under High-Intensity Ultrasound: A Novel Approach to an Old Reaction,” European J. Org. Chem., no. 22, pp. 4438–4444, 2003,

doi: 10.1002/ejoc.200300369.

[21] H. J. K. and Y. B. Prabhudev S. M.*, Samina Sultana, Kishore Singh C., “Synthesis, Characterization and Biological Evaluation of Dibenzalketone Derivatives,” World J. Pharm. Res., vol. 9, no. 3, pp. 5041–5048, 2020,

doi: 10.20959/wjpr20205-17388.

[22] Y. Purwaningsih, E. Indriyanti, and A. F. Masduqi, “Synthesis of PMCA (P-Methoxy Cinnamic Acid) using Perkin Reaction and Its Activity as Photo Protective and Antifungal Agent,” JKPK (Jurnal Kim. dan Pendidik. Kim., vol. 7, no. 2, p. 138, 2022,

doi: 10.20961/jkpk.v7i2.61294.

[23] W. A. E. Setyowati, R. P. Nurisah, and P. I. Wulandari, “Binahong Leaves Water Extract (Anredera cordifolia (Tenore) Steen.) as a Natural Foaming and Antibacterial Agent of Antiseptic Liquid Bath Soap,” JKPK (Jurnal Kim. dan Pendidik. Kim., vol. 5, no. 2, p. 167, 2020,

doi: 10.20961/jkpk.v5i2.29892.

[24] S. Rodrigues, L. C. A. Mazzone, F. F. P. Santos, M. G. A. Cruz, and F. A. N. Fernandes, “Optimization of the production of ethyl esters by ultrasound assisted reaction of soybean oil and ethanol,” Brazilian J. Chem. Eng., vol. 26, no. 2, pp. 361–366, 2009,

doi: 10.1590/S0104-66322009000200013.

[25] B. Banerjee, “Recent developments on ultrasound-assisted organic synthesis in aqueous medium,” J. Serbian Chem. Soc., vol. 82, no. 7–8, pp. 755–790, 2017,

doi: 10.2298/JSC170217057B.

[26] H. A. D. Chen, ‎ S.K. Sharma, A. Mudhoo (Eds.), Handbook on Applications of Ultrasound, Sonochemistry for Sustainability. Boca Raton: CRC Press, 2012,

doi: 10.1201/b11012.

[27] L. N. Amsad, S. Liliasari, A. Kadarohman, and R. E. Sardjono, “Accomplishing the synthesis of dibenzalacetone by using retrosynthesis approach to explore students’ performance,” J. Eng. Sci. Technol., vol. 14, pp. 10–18, 2019.

Google Scholar

[28] S. Handayani, S. Matsjeh, C. Anwar, S. Atun, and I. Fatimah, “Reaction Efficiency of Crossed-Aldol Condensation between Acetone and Benzaldehyde over ZrO₂ and ZrO₂-Montmorillonite Catalyst,” J. Appl. Sci. Res., vol. 8, no. 5, pp. 2457–2464, 2012.

Google Scholar

[29] P. Kulkarni and G. Totre, “Synthesis of dibenzylidene acetone via aldol condensation of diacetone alcohol with substituted benzaldehydes,” Orbital, vol. 11, no. 5, pp. 292–296, 2019,

doi: 10.17807/orbital.v11i5.1388.

[30] S. Handayani, C. Budimarwanti, and W. Haryadi, “Microwave-assisted organic reactions: Eco-friendly synthesis of dibenzylidenecyclohexanone derivatives via crossed aldol condensation,” Indones. J. Chem., vol. 17, no. 2, pp. 336–341, 2017,

doi: 10.22146/ijc.25460.

[31] V. A. Fabiani and R. Lingga, “Green Synthesis of Silver Nanoparticles via Cratoxylum glaucum Leaf Extract Loaded Polyvinyl Alcohol and Its Antibacterial Acitvity,” JKPK (Jurnal Kim. dan Pendidik. Kim., vol. 7, no. 3, p. 314, 2022,

doi: 10.20961/jkpk.v7i3.64719.

[32] E. Susilowati, S. R. D. Ariani, L. Mahardiani, and L. Izzati, “Synthesis and Characterization Chitosan Film with Silver Nanoparticle Addition As A Multiresistant Antibacteria Material,” JKPK (Jurnal Kim. dan Pendidik. Kim., vol. 6, no. 3, p. 371, 2021,

doi: 10.20961/jkpk.v6i3.57101.

[33] T. Shahwan, “Lagergren equation: Can maximum loading of sorption replace equilibrium loading?,” Chem. Eng. Res. Des., 2015,

doi: 10.1016/j.cherd.2015.03.001.

DOI: https://doi.org/10.20961/jkpk.v8i3.65172