Skip to main content
SpringerLink
Log in

1-Octen-3-ol and its relation to other oxidative cleavage products from esters of linoleic acid

  • Technical
  • Published:
Journal of the American Oil Chemists Society

Abstract

By means of preparative GLC, 1-octen-3-ol and 2-trans-heptenal could be isolated from mildly oxidized linoleic acid ester and from oils containing this acid (e.g., soybean oil). A hypothesis for the origin of these two substances in natural products is given. The absence of 2-trans-octenal in the cleavage products from methyl linoleate, its presence in oils and the controversial experimental results obtained by various investigators, seem to be reconcilable by assuming the formation of an acetal. The suggested acetal may, on intermolecular cyclic rearrangement and cleavage, give 1-octen-3-ol. *** DIRECT SUPPORT *** A03O2190 00002

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. Hoffmann, G., JAOCS38, 1 (1961).

    CAS  Google Scholar 

  2. Hoffmann, G., Ibid.38, 31 (1961).

    Article  Google Scholar 

  3. Murahashi, Sh., Chem. Abstr.32, 3755 (1938).

    Google Scholar 

  4. Naves, Y. R., helv. Chim. Acta26, 1992 (1943).

    Article  CAS  Google Scholar 

  5. Sfiras, J., Chem. Abstr.48, 3932 (1954).

    Google Scholar 

  6. Crabalona, L., Bull. soc. chim. France11, 67 (1944).

    CAS  Google Scholar 

  7. Martin, C. J., A. I. Schepartz, and B. F. Daubert, JAOCS25, 113 (1948).

    CAS  Google Scholar 

  8. Forss, D. A., E. A. Dunstone, and W. Stark, J. Dairy Res.27, 373 (1960).

    Article  Google Scholar 

  9. De Bruyn, J., and J. C. M. Schogt, JAOCS38, 40 (1961).

    Article  Google Scholar 

  10. Radlove, S. B., Ibid.35, 236 (1958).

    CAS  Google Scholar 

  11. Levene, P. A., and A. Walti, J. Biol. Chem.94, 353 (1931).

    CAS  Google Scholar 

  12. Lathlean, B., Paint J. Australia and New Zealand3 [1], 12–13, 15–18 (1958).

    CAS  Google Scholar 

  13. Ellis, R., A. M. Gaddis, and G. T. Currie, Food Technol.14 [4] (1960). Insert of Techn. Program 20th Am. Meeting. No. 86. p. 30.

    Google Scholar 

  14. Sephton, H. H., and D. A. Sutton, JAOCS33, 263 (1956).

    Article  CAS  Google Scholar 

  15. Bergström, S., Arkiv Kemi, Mineral. Geol. 21A [14], 1 (1945). Nature156, 717 (1945).

    Google Scholar 

  16. Privett, S. et al., JAOCS30, 61 (1953).

    CAS  Google Scholar 

  17. Badings, H. T., Ibid.36, 648 (1959).

    CAS  Google Scholar 

  18. Patton, S., I.J. Barnes, and L. E. Evans, Ibid.36, 280 (1959).

    CAS  Google Scholar 

  19. Swift, C. E. et al., Ibid.26, 297 (1949).

    CAS  Google Scholar 

  20. Frankel, E. N., J. Nowakowska, and C. D. Evans, Ibid.38, 161 (1961).

    CAS  Google Scholar 

  21. Powick, W. C., J. Agr. Research36, 323 (1923).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Unilever Research Laboratory, Vlaardingen, The Netherlands

    G. Hoffmann

Authors
  1. G. Hoffmann
    View author publications

    You can also search for this author in PubMed Google Scholar

About this article

Cite this article

Hoffmann, G. 1-Octen-3-ol and its relation to other oxidative cleavage products from esters of linoleic acid. J Am Oil Chem Soc 39, 439–444 (1962). https://doi.org/10.1007/BF02637660

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02637660

Keywords

Search

Navigation