Journal of Chemical Ecology

, Volume 38, Issue 12, pp 1493–1503

First Sex Pheromone of the Order Strepsiptera: (3R,5R,9R)-3,5,9-Trimethyldodecanal in Stylops melittae Kirby, 1802


DOI: 10.1007/s10886-012-0215-6

Cite this article as:
Tolasch, T., Kehl, S. & Dötterl, S. J Chem Ecol (2012) 38: 1493. doi:10.1007/s10886-012-0215-6


The twisted-wing parasites (Strepsiptera) are an unusual and small order of insects with about 600 known species. As obligate endoparasitoids, they develop and spend most of their lives living in other insects. Adults show an extreme sexual dimorphism: The free-living males have large eyes, branched antennae, reduced forewings, and well developed hind wings, while the neotenic females of most species lack all external characters that normally define an insect, remain endoparasitic, and only extrude the cephalothorax from the host. Due to the males’ short life span of only a few hours, there must be an efficient means of mate finding. This is believed to be mediated by chemical cues released by virgin females. Here, we report the first identification and synthesis of a female-produced strepsipteran sex pheromone, (3R,5R,9R)-3,5,9-trimethyldodecanal, from Stylops melittae, a species parasitizing andrenid bees. We found this highly EAD-active compound to be present in cephalothoraxes of and released from unmated females, and synthetic samples proved to be extremely attractive when offered in the field during the swarming period of the males. The structural features of this new natural compound may further support the re-establishment of the Strepsiptera as the closest living relatives of the Coleoptera.


Strepsiptera Stylopidae Stylops Andrena Twisted-wing parasite 3,5,9-Trimethyldodecanal GC-EAD GC-MS Endoparasitoid Taxonomy 

Copyright information

© Springer Science+Business Media New York 2012

Authors and Affiliations

  1. 1.Universität Hohenheim, Institut für ZoologieStuttgartGermany
  2. 2.Universität Bayreuth, Lehrstuhl Tierökologie IIBayreuthGermany
  3. 3.Universität Bayreuth, Lehrstuhl PflanzensystematikBayreuthGermany
  4. 4.Organismic Biology, Plant Ecology, Salzburg UniversitySalzburgAustria

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