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J Chem Ecol. 2012 Dec;38(12):1483-91. doi: 10.1007/s10886-012-0214-7. Epub 2012 Nov 11.

Stylopsal: the first identified female-produced sex pheromone of strepsiptera.

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  • 1Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, vvi., Flemingovo nám. 2, 16610, Prague 6, Czech Republic.

Erratum in

  • J Chem Ecol. 2012 Dec;38(12):1492.


A female-produced sex pheromone of Stylops muelleri was identified as an unusually branched saturated aldehyde (9R)-3,5-syn-3,5,9-trimethyldodecanal. We named it stylopsal. Its structure was established by using mass spectrometry, infrared spectroscopy, and organic synthesis of candidate compounds. The synthetic standard of (9R)-3,5-syn-3,5,9-trimethyldodecanal gave identical chromatographic and mass spectrometric data as the natural pheromone and also was active in electroantennographic and behavioral assays. The female fat body lipids contained the corresponding fatty acid, indicating a possible link between lipid metabolism and the pheromone biosynthesis.

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