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.

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

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

See more in PubMed

J Chem Ecol. 2008 Jun;34(6):772-82 PubMed

Angew Chem Int Ed Engl. 2005 Apr 29;44(18):2752-2756 PubMed

Mass Spectrom Rev. 2000 Nov-Dec;19(6):398-420 PubMed

Anal Chem. 2000 Jan 1;72(1):101-9 PubMed

PLoS One. 2010 Jul 29;5(7):e11887 PubMed

Z Parasitenkd. 1953;15(6):457-75 PubMed

Hoppe Seylers Z Physiol Chem. 1951 Mar;287(1-2):65-89 PubMed

Mol Phylogenet Evol. 2011 Feb;58(2):169-80 PubMed

Mol Phylogenet Evol. 2010 Jun;55(3):846-59 PubMed

J Am Chem Soc. 2002 Mar 27;124(12):2870-1 PubMed

Lipids. 2008 May;43(5):441-50 PubMed

J Org Chem. 2005 Mar 4;70(5):1808-27 PubMed

J Am Soc Mass Spectrom. 1991 May;2(3):245-9 PubMed

Tissue Cell. 2004 Jun;36(3):211-20 PubMed

Syst Biol. 1997 Mar;46(1):1-68 PubMed

The Paragenital Organ of Stylopidae (Insecta: Strepsiptera) and the Functional Incorporation of the Secondary Larval Exuvia

Strepsiptera of Canada