Journal of Chemical Ecology

, Volume 8, Issue 1, pp 163–175 | Cite as

(Z)-11-eicosen-1-ol, an important new pheromonal component from the sting of the honey bee,Apis mellifera L. (Hymenoptera, Apidae.)

  • J. A. Pickett
  • Ingrid H. Williams
  • A. P. Martin


(Z)-11-Eicosen-1-ol was identified by GC-MS and microchemical methods as a major volatile component, ca. 5 μg per insect, secreted by the sting apparatus of the worker honey bee. When presented on moving lures at the hive entrance, (Z)-11-eicosen-1-ol, like isopentyl acetate already known as an alarm pheromone, elicited stinging, and together these two compounds were as active as the natural pheromone from the sting. On stationary lures, (Z)-11-eicosen-1-ol prolonged the effectiveness of isopentyl acetate.

Key words

Honey bee Apis mellifera Hymenoptera Apidae pheromone (Z)-11-eicosen-1-ol sting EAG alarm pheromone mass spectrometry epoxides 


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. Beroza, M., andBierl, B.A. 1967. Rapid determination of olefin position in organic compounds in microgram range by ozonolysis and gas chromatography.Anal. Chem. 39:1131.Google Scholar
  2. Bierl-Leonhardt, B.A., Devilbiss, E.D., andPlimmer, J.R. 1980. Location of double-bond position in long-chain aldehydes and acetates by mass spectral analysis of epoxide derivatives.J. Chrormatogr. Sci. 18:364–367.Google Scholar
  3. Boch, R., andShearer, D. A. 1966. Iso-pentyl acetate in stings of honeybees of different ages.J. Apic. Res. 5:65–70.Google Scholar
  4. Boch, R., Shearer, D.A. andStone, B.C. 1962. Identification of iso-amyl acetate as an active component in the sting pheromone of the honey bee.Nature 195:1018–1020.Google Scholar
  5. Boch, R., Shearer, D.A., andPetrosovits, A. 1970. Efficacies of two alarm substances of the honey bee.J. Insect Physiol. 16:17–24.Google Scholar
  6. Blum, M.S., Fales, H.M., Tucker, K.W., andCollins, A.M. 1978. Chemistry of the sting apparatus of the worker honey bee.J. Apic. Res. 17:218–221.Google Scholar
  7. Budzikiewicz, H., Djerassi, C., andWilliams, D.H. 1967. Mass Spectrometry of Organic Compounds. Holden-Day, London, p. 449.Google Scholar
  8. Free, J.B., andSimpson, J. 1968. The alerting pheromones of the honeybee.Z. Vergl. Physiol. 61:361–365.Google Scholar
  9. Ghent, R.L., andGary, N.E. 1962. A chemical alarm releaser in honey bee stings (Apismellifera L.)Psyche 69:1–6.Google Scholar
  10. Koeniger, N., Weiss, J., andMaschwitz, U. 1979. Alarm pheromones of the sting in the genusApis.J. Insect Physiol. 25:467–475.Google Scholar
  11. Kullenberg, B., Bergstrom, G., andStallberg-Stenhagen, S. 1970. Volatile components of the cephalic marking secretion of male bumble bees.Acta Chem. Scand. 24:1481–1483.Google Scholar
  12. Mass Spectrometry Data Centre. 1975. Eight Peak Index of Mass Spectra, 2nd ed., Reading, U.K.Google Scholar
  13. Pickett, J.A., Williams, I.H., Martin, A.P., andSmith, M.C. 1980. Nasonov pheromone of the honey bee,Apis mellifera L. (Hymenoptera: Apidae). Part I. Chemical characterization.J. Chem Ecol. 66:425–434.Google Scholar
  14. Pringle, J. W.S. 1938 Proprioceptors in insects. I A new type of mechanical receptor from the palps of the cockroach.J. Exp. Biol. 15:101–113.Google Scholar
  15. Sugawara, F., Kobayashi, A., Yamashita, K., andMatsuda, K. 1978. Identification of octadecyl acetate and (Z)-11-octadecenyl acetate, major components of the defensive secretion ofGastrophysa atroceana Motschulsky.Agric. Biol. Chem. 43:687.Google Scholar
  16. Williams, I.H., Pickett, J.A., andMartin, A.P. 1981. Nasonov pheromone of the honey bee,Apris mellifera L. (Hymenoptera: Apidae). Part II. Bioassay of the components using foragers.J. Chem. Ecol. 7:225–237.Google Scholar
  17. Williams, I.H.,Pickett, J.A., andMartin, A.P. 1982. Nasonov pheromone of the honey bee,Apis mellifera L. (Hymenoptera: Apidae). Part IV. Electrophysiological bioassay of the components.J. Chem. Ecol. In press.Google Scholar

Copyright information

© Plenum Publishing Corporation 1982

Authors and Affiliations

  • J. A. Pickett
    • 1
  • Ingrid H. Williams
    • 1
  • A. P. Martin
    • 1
  1. 1.Rothamsted Experimental StationHarpendenEngland

Personalised recommendations