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(S)-2,3-Dihydrofarnesoic Acid, a New Component in Cephalic Glands of Male European Beewolves Philanthus triangulum

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Abstract

The chemical composition and functional significance of pheromones of solitary Hymenoptera is much less well known compared to social species. Males of the genus Philanthus (Sphecidae) are territorial and scent mark their territories to attract females. Because of inconsistent results of earlier studies, we reanalyzed the content of the cephalic glands of male European beewolves, Philanthus triangulum F. Besides a variety of alkanes and alkenes, four major compounds were found. Two of these, (Z)-11-eicosen-1-ol and (Z)-10-nonadecen-2-one, had been previously described as constituents of the cephalic glands. We identified 1-octadecanol as a new component of the cephalic gland, and a fourth compound, enantiopure (S)-2,3-dihydrofarnesoic acid, was identified for the first time in nature. Structural elucidation and enantiomeric analysis were performed by HRGC-MS and HRGC-FTIR as well as enantioselective gas chromatography and by means of authentic reference compounds. Occurrence and

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Authors and Affiliations

  1. Theodor-Boveri-Institut für Biowissenschaften, Zoologie III, Biozentrum, Am Hubland, D-97074, Würzburg, Germany

    Thomas Schmitt, Erhard Strohm & Gudrun Herzner

  2. Lehrstuhl für Lebensmittelchemie, Am Hubland, D-97074, Würzburg, Germany

    Thomas Schmitt, Frank Heckel & Peter Schreier

  3. Dipartimento di Scienza e Tecnologia Del Farmaco, Università degli Studi di Torino, Via Pietro Giuria, I-10125, Torino, Italy

    Carlo Bicchi

  4. Symrise AG, D-37603, Holzminden, Germany

    Gerhard Krammer

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  1. Thomas Schmitt
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  2. Erhard Strohm
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  3. Gudrun Herzner
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Correspondence to Erhard Strohm.

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Schmitt, T., Strohm, E., Herzner, G. et al. (S)-2,3-Dihydrofarnesoic Acid, a New Component in Cephalic Glands of Male European Beewolves Philanthus triangulum . J Chem Ecol 29, 2469–2479 (2003). https://doi.org/10.1023/A:1026305901049

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