Authors : Chukwueke, A. K.; Iwu, I. C.; Akalezi, C.; Alisa, C. O.; Ndukwu, D. E.

Volume/Issue : Volume 11 - 2026, Issue 7 - July

Google Scholar : https://tinyurl.com/2fb6p3ee

Scribd : https://tinyurl.com/553bzsnw

DOI : https://doi.org/10.38124/ijisrt/26jul1447

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Abstract : Methyl 3- (N-benzyl-N, N-diethylammonium) propanoate bromide was synthesized via quaternization of methyl 3- (N, N-diethylamino) propanoate with benzyl bromide. The synthesized Benzalkonium quaternary ammonium compound possessing ester functionality was characterized by FTIR, 1HNMR, 13CNMR and GC-MS. The antimicrobial activity of the ester QAC was achieved by determining its minimum inhibitory concentration (MIC) value and minimum bactericidal concentration (MBC) value against strains of gram-positive Bacterial (S. Pneumonae, B. aureus, S. aureus) and gramnegative Bacterial (K. Pneumonae, E. Coli) Our findings revealed that the synthesized soft QAC containing a hydrolysable ester group primarily exhibit bactericidal and bacteriostatic mode of action, effectively inhibiting bacterial growth even at appreciable minimum inhibitory concentration value of 6.25mg/L.

Keywords : Soft QAC, Bactericidal, Bacteriostatic, Quaternization, Synthesized, Benzalkonium, Hydrolysable.

References :

1. Avci, D, Mathias, L.J., Ayfer, B., Dizman, B. and ELasri, M.O. (2005) Synthesis and antibacterial activities of new quaternary ammonium monomers. Designed monomers and polymers. 8, (5) 437 – 451.
2. Barney, R., Stark, T., and Delavet, D. (2005). Synthesis and surfactant studies of Diakyl Dimethyl Quaternary Ammonium Bromide formulations. American Journal of Und. (Review) Research 5 (3) 1 – 4.
3. Beghetto, V., Morandini, A; Spadati, E., Leonetti, B; Sole, R., Gatto, V., and Rizzolio, F., (2021). Sustainable Triazine-derived quaternary ammonium salts as antimicrobial agents. Royal society of Chem. Vol. 11 28092.
4. Beghetto, V., Rizzolio, F., Caliguri, I., Gatto, V., Sole, R., Riello, P., Leonetti, B., and Morandini, A., Synthesis and Antimicrobial Evaluation of Bis- morpholine Triazine Quaternary Ammonium Salts (2021). Chem Medchem. Vol. 16, (20) Pp. 3172 – 3176.
5. Boethling, R.S. 1984. Environmental fate and toxicity in waste water treatment of quaternary ammonium surfactants. Water Research 18 (9): 1061 – 1076.
6. Crnecevic, D., Krce, L., Brkljaca Z., Cvitkovic, M., Babic, S., Coz-Rakovac, R., Odzak, R. and Spning, M., (2025). A dud antibacterial action of soft quaternary ammonium compound: bacteriostatic effects, membrane integrity and reduced in vitro and in vivo toxicity. Royal society of chem. (15) 1490 - 1506.
7. Cross, J. (1994). Cationic surfactant: analytical and biological evaluation; Mercel Dekker. Vol. 053.
8. Delaet, D., Stark, T. and Barney, R. (2005). Synthesis and surfactant studies of Diakyl Dimethyl Quaternary ammonium bromide formulations American Journal of undergraduate Research 5 (#).
9. Devinsky, F., Lacko, I., Bittererova, F., and MLYnarcik, D. (1987). Quaternary ammonium salts. Preparation and relationship between structure, IR spectral characteristics and antimicrobial activity of some new bis- quaternary isosters of 1,5-Pentanediammonium dibromides chem. Papers 41 (6) 803 – 814.
10. Dong Qing X, Zhong – Wen P. (2014) Phase Transfer Catalysis – Literature Review contd. Phase Transfer of a new cationic Gemini surfoctant with easter groups for nucleophilic substitution reaction. Journal of Chinese Chemistry. Lett. 2014, 25(08) 1169 – 1173.
11. Feldman, D., Nir, M., Rabinovitz, M., and Lissel, M. (1989). Bis-quaternary ammonium salts as phase transfer catalysts. Tetrahedron letters. 30 (13) 1683 – 1686.
12. Fisher J. Cleaning procedures in the factory: types of disinfectants. Encyclopedia of food, science and nutrition: 2^nd edition 2003.
13. Fu, S., Liu, J., Hou, P., Liu, L., and Zhang, H. (2021). Design, synthesis, Antibacterial, and Antitumor Activity of Linear Polyisocyanide Quaternary Ammonium salts with Different Structures and chain lengths. Molecules 26, 5686.
14. Gerba, C.P., (2015). Quaternary ammonium Biocides: Efficacy in Application. Applied and Environmental Microbiology 81(2) 464 – 469.
15. Ghig, G; Cagnina S. Maranzana, A. and Tonachini, G. 2010; The mechanism of the Stevens and Sommelet-Hauser Rearrangements. A theoretical study. Journal of Organic Chemistry. 75(11) 3608-3617.
16. Gozzelino G., Tobar R., Chaitiemwong N., Haeleger W., and Beumer R. 2011. Antibacterial Activity of Reactive Quaternary Ammonium Compounds in  solution and in Non-Leachable Coating. Journal of Food Protection, Vol 74, No 12, 2107-2112.
17. Lelciu, I., Vostinaru, O., Oniga, S., and Mogosom, C. (2013). Synthesis and effects of some new 2-aryl-thiazole ammonium salts on isolated ileum motility. Digest Journal of Nanomaterials and Biostructures 8 (3): 1089 – 1099.
18. Lindstedt M., Allenmark S., Thompson R.A. and Edebo L. 1990. Antimicrobial activity of betaine esters, quaternary ammonium amphiphiles which spontaneously hydrolyze into nontoxic components. Antimicrobial agents and chemotherapy. Vol 34, No. 10.1949-1954.
19. Marouka K. and Ooi T (2003). Enatioselective Amino Acid Synthesis by Chiral Phase Transfer Catalysis. Chemical Review, (103) 3013 – 3028.
20. Mcbain, A.J., Ledder, R.G., Moore, L.E., Catrenich, C.E., and Gilbert P., (2004) Effects of quaternary ammonium-based formulation on bacterial community dynamics and antimicrobial susceptibility. 70 (6) 3449 – 3456.
21. Mcdonnell G. Russell, A.D. 1999. Antiseptics and disinfectants activity, action and resistance. Clinical Microbiology Review, Jan 12(1), 147-179.
22. Mcmurry, J. Organic chemistry, 2^nd edition, Brooks/Cole publishing company, California. 1988.
23. Michocka K., Staszak K., Gwiazdowska D. and Wieczorek D. 2019. Synthesis, surface and Antimicrobial Activity of New Lactose-Based Surfactants. Molecules. Vol 24, 4010.
24. Munawar, A.M., Gul, S., Salem, M., Ahmad, H.A., Ahmad, Ahmed, E., and Farooqi, Z.H., Synthesis of novel quaternary ammonium salts from 1,2- benzothiazine derivates (2020). Journal of Sulfur Chemistry. Vol. 10 1080/17415.
25. Sommer, Z.H., Lipp, H.I., and Jackson, L. (1971). Alkylation of Amines. A general exhaustive Alkylation method for the synthesis of quaternary Ammonium Compounds (Review). Organic Chemistry 36 (6) 824.
26. Sprung, M., Crncevic, D., Sabljic, A., Primozic, I., and Odzak, R. (2023). Synthesis and Biological Evaluation of 3-Amidoquinuchidine quaternary Ammonium compounds as Newsoft antimicrobial agents. Pharmaceuticals 16 (2) 187.
27. Sprung, M., Primozic, I., Aviani, I. propovic, B.V., Odziak, R., Soldo, B., Krce, L., Maravic, A. and Bazina, L. Discovery of novel quaternary ammonium compounds based on quinuclidine – 3 – ol as new potential antimicrobial candidates (2019). European J. of Medicinal Chemistry. Vol. 163 P 626- 635.
28. Sprung, M., Primozic, I., Weber, I., Krce, L., Crncevic, D., Ramic, A., and Kastelic, A.R. (2024). Naturally derived 3-aminoquinuclidine salts as new promising therapeutic agents Scientific reports (14) 26211.
29. Sprung, M., Vuko, E., Sabijic, A., Brkljaca, Z., Cvitkovic, M., Krce, L., Crncevic D., Primozic, I., and Odzak, R. (2022). New membrane Active Antibacterial and Antiviral Amphiphiles derived from Heterocyclic backbone of Pyridinium – 4 – Aldoxime Pharmaceuticals, 15, 775.
30. Streitweiser, A., Heathcock, C.H., Kosower, E.M. (1992). Intro. To Organic Chemistry, 4^th Edition, Macmillan Publishing Company. New York.
31. Sugasawa S. and Matsuo, H. 1958. A modified Emde Degradation. Reductive cleavage of Quaternary ammonium salts by Raney Nickel. Chemical and pharmaceutical bulletin. 6 (6) 601-607.
32. Tahar, B., Mohammed, M., Aicha, D. and Eddine, H.D. (2010). Anti-bacterial activity of quaternary ammonium salt from Diethyl amino ethyl methylacyrlate. E-Journal of Chemistry. 7 (51) 861 – 866.
33. Wuest, W.M., Minbiole, P.C., Jenings, M.C., Santiago, C.N. and Joyce, M.D. (2016). Natural product – derived quaternary ammonium compounds with potent antimicrobial activity. The journal of Antibiotics (69) 344 – 347.
34. Xue, Y, Xiaom H. and Zhange, Y. 2015. Antimicrobial polymeric material with quaternary ammonium and phosphonium salts. Int. Journ. of Molecular Science. 16 (2) 3626 – 3655.
35. Youssef, M.M., El-Bordany, E. and Azad, M.E. (2013). Synthesis and Antibacterial Evaluation of Novel Heterocyclic compounds containing a sulfonamido moiety. Molecules (18) 832 – 844.
36. Christensen, J. B., Leisner, J. J., Ficker, M., Counil, C., Frederiksen, R.F., and Soven, W. S. 2020. Synthesis and Antimicrobial properties of Ciprofloxacin and PAMAM - dendrimer conjugate. Molecules (61) 1389.
37. Ezelerab, H. A. A., Abbas, S., Abourehab, M., and Basr, M. 2021. Novel antimicrobial Ciprofloxacin – Pyridinium quaternary ammonium salts with improved physiochemical properties and DNA gyrase inhibitory activity. Medicinal Chemistry Research. 30 (12).