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ARTICLE

Application of the Principles of “Green Chemistry” for the Synthesis of 10-Undecylenic Aliphatic Esters with Antimicrobial Activity

Dragomir Vassilev^1,*, Nadezhda Petkova², Yulian Tumbarski³, Milena Koleva¹, Panteley Denev²

1 Department of Physics, Chemistry and Ecology, Technical University of Gabrovo, Gabrovo, 5300, Bulgaria
2 Department of Inorganic and Organic Chemistry, University of Food Technologies, Plovdiv, 4002, Bulgaria
3 Department of Microbiology, University of Food Technologies, Plovdiv, 4002, Bulgaria

* Corresponding Author: Dragomir Vassilev. Email:

(This article belongs to the Special Issue: The 10th Conference on Green Chemistry and Nanotechnologies in Polymeric Materials (GCNPM 2019))

Journal of Renewable Materials 2020, 8(6), 675-686. https://doi.org/10.32604/jrm.2020.09279

Received 29 November 2019; Accepted 09 March 2020; Issue published 12 May 2020

Abstract

Undenicylic acid (10:1) is known as an antifungal agent and an active ingredient of many topical medicines [1–6]. The present research investigates the preparation of aliphatic esters of 10-undecylic acid with butanol and i-amyl alcohol by the conventional and ultrasound-assisted syntheses as well as the structural elucidation of the resulting compounds, by FTIR and NMR spectroscopy. The antimicrobial properties of the obtained 10-undecylenic esters were tested against Gram-positive bacteria (Staphylococcus aureus; Enterococcus faecalis; Listeria monocytogenes), Gram-negative bacteria (Escherichia coli; Salmonella sp.) and filamentous fungi (Penicillium sp.; Aspergillus niger; Fusarium moniliforme) using the conventional agar-well diffusion assay. The results demonstrated that all esters had insignificant antibacterial activity. i-Amyl-10-undecylenate and t-butyl-10-undecylenate showed activity against both Gram-positive and Gram-negative bacteria, while i-butyl-10- undecylenate and n-butyl-10-undecylenate were effective only against Gram-positive bacteria tested. In contrast, all 10-undecylenic esters demonstrated high antifungal activity, which was most pronounced in i-Amyl-10-undecylenate. Therefore, the obtained products can be successfully used as promising antifungal agents for various pharmaceutical formulations as well as biocontrol means against plant pathogens.

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