trans-Tetradec-2-enoic Acid in Impatiens glandulifera

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

Keywords:

• Himilayan balsam
• Horner–Wadsworth–Emmons
• Impatiens glandulifera (Balasaminaceae)
• lipids
• metabolites

ACKNOWLEDGMENTS

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