Journal of Chemical Ecology

, Volume 38, Issue 12, pp 1493–1503 | Cite as

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

  • Till Tolasch
  • Siegfried Kehl
  • Stefan Dötterl


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 



We thank Susanne Sölter (Agilent Technologies) and Gunnar Weibchen (Waters GmbH) for the GC-CIMS analyses in the former Varian application lab, Jürgen Conrad (Hohenheim) for recording the NMR data, Wolfgang Rutkies (Osnabrück) and Alexander Endreß (Bayreuth) for support during field work, Bernhard Rothweiler and Moritz Hebestreit (Agilent) for lending us their 60 m DB-23 column, Kim Steiner (San Francisco) and two anonymous reviewers for comments on earlier versions of the manuscript.


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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

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