Synthesis and antimicrobial activity of the essential oil compounds (E)- and (Z)-3-hexenyl nonanoate and two analogues
Date
2012
Journal Title
Journal ISSN
Volume Title
Publisher
University of KwaZulu-Natal
Abstract
The synthesis of (E)- and (Z)-3-hexenyl nonanoate, known constituents of essential oil containing plants, and two related compounds is reported. These compounds were assembled from nonanoyl chloride or nonanoic acid and the respective alcohols. In particular, it was found that the use of triethylamine as a co-solvent was necessary to avoid acid-mediated isomerization of the alkenes, which resulted in an inseparable mixture of products. The antimicrobial activity of the four hexenyl and hexyl nonanoate compounds was undertaken using microdilution minimum inhibitory concentration (MIC) analysis against eight test microorganisms. All four compounds demonstrated activity, with (E)-3-hexenyl nonanoate 1B: having the highest inhibition (MIC value of 0.45 mg mL-1) against Pseudomonas aeruginosa ATCC 27858. Furthermore, this compound demonstrated the highest broad-spectrum activity (mean MIC value of 1.24 ± 0.50 mg mL-1) with noteworthy activity against all pathogens tested.
Description
CITATION: Chakravorty, S. et al. 2012. Synthesis and antimicrobial activity of the essential oil compounds (E)- and (Z)-3-hexenyl nonanoate and two analogues. South African Journal of Chemistry, 65:202-205.
The original publication is available at http://www.scielo.org.za
The original publication is available at http://www.scielo.org.za
Keywords
Essences and essential oils -- Composition, Anti-infective agents
Citation
Chakravorty, S. et al. 2012. Synthesis and antimicrobial activity of the essential oil compounds (E)- and (Z)-3-hexenyl nonanoate and two analogues. South African Journal of Chemistry, 65:202-205.