Skip to main content
SpringerLink
Log in

On the odour shift from bitter almond odour to cinnamic-floral notes

Zum Geruchswechsel von Bittermandelgeruch zu zimt-blumigen Noten

  • Organische Chemie Und Biochemie
  • Published:
Monatshefte für Chemie / Chemical Monthly Aims and scope Submit manuscript

Summary

The structural differences between bitter almond odour substances and molecules with cinnamic or floral odour notes were investigated by comparison of a number of compounds with various synthetic modifications. An attempt was made to find a systematic principle for the change of the odour notes.

Zusammenfassung

Strukturelle Unterschiede zwischen Substanzen mit Bittermandelgeruch und Molekülen mit zimtartigen oder blumigen Noten wurden durch Vergleich einer Anzahl von durch Synthese verschieden modifizierten Verbindungen studiert. Es wurde versucht, ein systematisches Prinzip für den Geruchswechsel zu finden.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Beets M. G. J. (1971) In: Beidler L. M. (ed) Handbook of sensory physiology, vol. IV. Chemical senses 1. Olfaction. Springer, Berlin Heidelberg New York, p 257 ff

    Google Scholar 

  2. Boelens H., Heydel J. (1973) Chemiker Ztg.97: 8

    Google Scholar 

  3. Amoore J. E. (1971) In: Ohloff G., Thomas A. F. (eds) Gustation and olfaction. Academic Press, London New York, p. 147

    Google Scholar 

  4. Wright R. H. (1954) J. Appl. Chem.4: 611

    Google Scholar 

  5. Wright R. H. (1969) Exc. Med. Int. Cong. Ser.206: 3

    Google Scholar 

  6. Lindner P., Märtensson O. (1972) Int. J. Quant. Chem.6: 363

    Google Scholar 

  7. Wright R. H., Robson A. (1969) Nature222: 290

    Google Scholar 

  8. Ericksson A., Lindner R., Märtensson O. (1981) In: Srinivasian R. (ed.) Biomolecular structure, conformation, function and evolution, vol. 2. Pergamon Press

  9. Zakarya D., Yahiaoui M., Fkih-Tetouani S. (1992) J. Soc. Maroc. Chim.1: 14

    Google Scholar 

  10. Boelens H. (1974) Cosmet. & Perf.89: 70

    Google Scholar 

  11. Beets M. G. J. (1978) In: “Structure-activity-relationships in human chemoreception”, p. 162ff, Appl. Sci. Publ., London

    Google Scholar 

  12. Worrall D. E. (1941) Org. Synthesis, VolI, 413

    Google Scholar 

  13. Gairaud C. B., Lappain G. R. (1953) J. Org. Chem.18: 1

    Google Scholar 

  14. Koremura M., Oku H., Shono T., Nakanishi T. (1961) Takamine Kenkyusho Nempo13: 212; C.A. (1962)57: 16451a

    Google Scholar 

  15. Karmarkar S. N., Kelkar S. L., Wadia M. S. (1985) Synth. Commun.15: 510

    Google Scholar 

  16. Agafonov N. E., Sedishev I. P., Dudin A. V., Kutin A. A., Stashina G. A., Zhulin V. M. (1991) Izv. Akad. Nauk. SSSR, Ser. Khim., 426; C.A. (1991)115: 28781x

    Google Scholar 

  17. Smith P. J., Dimmock J. R., Taylor G. (1972) Can. J. Chem.50: 871

    Google Scholar 

  18. Lenek G. J., Cejka L. (1941) Org. Synthesis, Vol I, 283

  19. Ivanoff D. (1924) Bull. Soc. Chim. France35: 1658

    Google Scholar 

  20. Keskin H., Miller R. E., Nord F. F. (1951) J. Org. Chem.16: 199

    Google Scholar 

  21. Patterson J. M. (1973) Org. Synthesis, Vol V, 585

  22. Tietze L. F., Eicher Th. (1989) Reactions and Syntheses in the organic Chemistry Laboratory 176

  23. Buchbauer G., Kalchhauser H., Wolschann P., Yahiaoui M., Zakarya D.; in preparation

  24. Allinger N. L. (1972) J. Am. Chem. Soc.99: 8127

    Google Scholar 

  25. Gaussian 90, Revision J; Frisch M. J., Heat-Gordon M., Trucks G. W., Foresman J. B., Schlegel H. B., Raghavachari K., Robb M., Binkley J. S., Gonzales C., Defrees D. J., Fox D. J., Whiteside R. A., Seeger R., Melius C. F., Baker J., Martin R. L., Kahn L. R., Stewart J. J. P., Topiol S., Pople J. A.; Gaussian Inc., Pittsburgh PA, 1990

  26. Steiner W. (1969) J. Soc. Cosmet. Chem.20: 729

    Google Scholar 

  27. Brower K. R., Schafer R. (1975) J. Chem. Educ.52: 538

    Google Scholar 

  28. Karner K., Seib K. (1977) Seifen-Fette-Öle-Wachse103: 117

    Google Scholar 

  29. Moncrieff R. W. (1967) In: “The chemical senses”, p. 483. Leonhard Hill, London

    Google Scholar 

  30. Boelens H. (1976) In: Benz G. (ed) Structure-acitivity-relationships in chemoreception. Retrieval, London, p. 197, Inform.

    Google Scholar 

  31. Lerner O. M. (1958) Zhur. Priklad. Khim.31: 663; C.A. (1959) V52, 18271g

    Google Scholar 

  32. Worrall D. E. (1938) J. Am. Chem. Soc.60: 2845

    Google Scholar 

  33. Campbell N., Anderson W., Gilmore J. (1940) J. Chem. Soc. 446

  34. Byrdy S., Eckstein Z., Plenkiewica J. (1961) Bull. Acad. Polon. Sci, Ser. Sci. Chim.9: 627

    Google Scholar 

  35. Koremura M., Oku H., Shono T., Nakanishi T. (1961) Takamine Kenkyusho Nempo13: 216; C.A. (1962)57: 16451d

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institut für Pharmazeutische Chemie, Universität Wien, A-1090, Vienna, Austria

    G. Buchbauer

  2. Institut für Organische Chemie, Universität Wien, A-1090, Vienna, Austria

    H. Kalchhauser

  3. Institut für Theoretische Chemie und Strahlenchemie, Universität Wien, A-1090, Vienna, Austria

    P. Wolschann

  4. Laboratoire de Chimie des Plantes et de Synthese Organique et Bioorganique, University Mohammed V, Fac. Sciences, Rabat, Morocco

    M. Yahiaoui

  5. Faculty of Sciences, University “Moulay Ismail”, Meknes, Morocco

    D. Zakarya

Authors
  1. G. Buchbauer
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. H. Kalchhauser
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. P. Wolschann
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. M. Yahiaoui
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. D. Zakarya
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Dedicated to Prof. Dr. K. Schlögl on the occasion of his 70th anniversary

Rights and permissions

Reprints and permissions

About this article

Cite this article

Buchbauer, G., Kalchhauser, H., Wolschann, P. et al. On the odour shift from bitter almond odour to cinnamic-floral notes. Monatsh Chem 125, 1091–1099 (1994). https://doi.org/10.1007/BF00811517

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00811517

Keywords

Search

Navigation