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

Dragomir Vassilev1,*, 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: email

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

Journal of Renewable Materials 2020, 8(6), 675-686.


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.


Cite This Article

Vassilev, D., Petkova, N., Tumbarski, Y., Koleva, M., Denev, P. (2020). Application of the Principles of “Green Chemistry” for the Synthesis of 10-Undecylenic Aliphatic Esters with Antimicrobial Activity. Journal of Renewable Materials, 8(6), 675–686.


cc This work is licensed under a Creative Commons Attribution 4.0 International License , which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
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