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(R)-(Z,E)-9,11-octadecadien-13-olide: An intriguing lactone fromHeliconius pachinus (Lepidoptera)

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Summary

A fourteen-membered lactone,(R)-(Z,E)-9,11-octadecadien-13-olide, was isolated from extruded abdominal glands of a Neotropical, nymphalid butterfly,Heliconius pachinus (Lepidoptera). This compound was obtained from mature adults of both sexes, but was not detected in young adults or pupae.

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Literature

  1. Hecker, E., and Butenandt, A., in: Techniques in Pheromone Research, p. 1. Eds H. E. Hummel and T. A. Miller. Springer-Verlag, New York 1984.

    Google Scholar 

  2. Brand, J. M., Young, J. C., and Silverstein, R. M., in: Progress in the Chemistry of Organic Natural Products. Eds W. Herz, H. Grisebach and G. W. Kirby. Springer-Verlag, Vienna-New York 1979.

    Google Scholar 

  3. Henrick, C. A., Carney, R. L., and Anderson, R. J., in: Insect Pheromone Technology: Chemistry and Applications, p. 27. Eds B. A. Bierl-Leonhardt and M. Beroza. ACS Symposium Series 190, American Chemical Society, Washington D.C. 1982.

  4. Brown, K. B. Jr., A. Rev. Ent.26 (1981) 427.

    Article  Google Scholar 

  5. Miyakado, M., Meinwald, J., and Gilbert, L. E., unpublished results.

  6. EI-MS (70 eV) of c:m/z 278 (4.0), 207 (1.8), 179 (2.5), 151 (6.4), 136 (6.2), 135 (5.5), 121 (8.6), 107 (14.3), 99 (79.7), 93 (39.0), 91 (31.4), 79 (67.3), 71 (41.0), 67 (74.4), 55 (73.9), 43 (73.0), 41 (100).

  7. Corey, E. J., and Nicolaou, K. C., J. Am. chem. Soc.96 (1974) 5614.

    Article  CAS  Google Scholar 

  8. Phillips, B. E., Smith, C. R. Jr, and Tjarks, L. W., J. org. Chem.35 (1970) 1916.

    Article  CAS  Google Scholar 

  9. The1H-NMR spectra and GLC retention times of the two lactones were indistinguishable.

  10. Moore, B. P., and Brown, W. V., Aust. J. Chem.29 (1976) 1365.

    Article  CAS  Google Scholar 

  11. Millar, J. G., Pierce, H. D. Jr, Pierce, A. M., Oehlschlager, A. C., Borden, J. H., and Barak, A. V., J. chem. Ecol.11 (1985) 1053.

    Article  CAS  PubMed  Google Scholar 

  12. Millar, J. G., Pierce, H. D. Jr, Pierce, A. M., Oehlschlager, A. C., and Borden, J. H., J. chem. Ecol.11 (1985) 1071.

    Article  CAS  PubMed  Google Scholar 

  13. Cavill, G. W. K., Davies, N. W., and McDonald, F. J., J. chem. Ecol.6 (1980) 371.

    Article  CAS  Google Scholar 

  14. Spencer, G. F., Plattner, R. D., and Miller, R. W., Phytochemistry16 (1977) 764.

    Article  CAS  Google Scholar 

  15. Gilbert, L., unpublished observation.

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Miyakado, M., Meinwald, J. & Gilbert, L.E. (R)-(Z,E)-9,11-octadecadien-13-olide: An intriguing lactone fromHeliconius pachinus (Lepidoptera). Experientia 45, 1006–1008 (1989). https://doi.org/10.1007/BF01953063

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