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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 43, 2013 - Issue 10
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Original Articles

trans-Tetradec-2-enoic Acid in Impatiens glandulifera

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Pages 1404-1412 | Received 27 Sep 2011, Published online: 05 Mar 2013
 

Abstract

Purification of the hydrophobic extracts of the flowers and seed pods of Impatiens glandulifera(Himilayan balsam) yielded 2-methoxy-[1,4]-naphthoquinone 1, 1-hydroxyeicosan-3-one 16, and an unusual unsaturated fatty acid, trans-tetradec-2-enoic acid 6. Mass spectrometry and nuclear magnetic resonance spectroscopy indicated that the latter compound (6) was isolated as a mixture with linolenic acid 8 and saturated acids 7, 9, and 10 (chain lengths C-16, 18, and 20). Its structure was subsequently proven by independent chemical synthesis.

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GRAPHICAL ABSTRACT

ACKNOWLEDGMENTS

We thank J. Kerner for facilitating access to the sampled Impatiens glandulifera plants, and financial support from University College Dublin is gratefully acknowledged.

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