Skip to main content
SpringerLink
Log in

Fluorescent products of lipid peroxidation: I. Structural requirement for fluorescence in conjugated schiff bases

  • Published:
Lipids

Abstract

The structural requirement for fluorescence in Schiff bases was defined. Aldehydes and amines were reacted and the structures of the Schiff bases N-hydroxyethyl-1-imino-2′,4′-hexadiene (I), N-1-benzal-2-hydroxyaminoethane (II), and N-1-benzal-2,2′-hydroxyaminoethane (III) were established by elemental analysis, IR spectral analysis and mass spectral analysis. The structures of N-alanyl-2-hydroxy-naphthylidine (IV) and N,N′-dileucinyl-1-amino-3-iminopropene (V) had been established previously. III, IV and V were fluorescent compounds and I and II were not. The results of these analyses suggest that an electron donating group in conjugation with an imine is the structure required for fluorescence.

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. Dahl, L.K., E.G. Hill and R.T. Holman, Arch. Biochem. Biophys. 98:253 (1962).

    Article  Google Scholar 

  2. Baker, N., and L. Wilson, J. Lipid Res. 7:253 (1966).

    Google Scholar 

  3. Crawford, D.L., T.C. Yu and R.O. Sinnhuber, J. Agr. Chem. 14:182 (1966).

    Article  CAS  Google Scholar 

  4. Chio, K.S., and A.L. Tappel, Biochemistry 8:2821 (1969).

    Article  PubMed  CAS  Google Scholar 

  5. Dillard, C.J., and A.L. Tappel, Lipids 6:715 (1971).

    Article  PubMed  CAS  Google Scholar 

  6. Porta, E.A., and W.S. Hartroff, in “Pigments in Pathology,” Edited by M. Wolman, Academic Press, New York, 1969, p. 191.

    Google Scholar 

  7. Tappel, A.L., in “Pathological Aspects of Cell Membranes,” Vol. 1, Edited by B.F. Trump and A. Aristila, Academic Press, New York, In press.

  8. Lillard, D.A., and E.A. Day, JAOCS 41:549 (1964).

    CAS  Google Scholar 

  9. McIntire, F.C., J. Amer. Chem. Soc. 69:1377 (1947).

    Article  CAS  Google Scholar 

  10. Margerum, J.D., and J.A. Sousa, Appl. Spectrosc. 19:91 (1965).

    Article  CAS  Google Scholar 

  11. Sawicki, E., T.W. Stanley and H. Johnson, Anal. Chem. 35:199 (1963).

    Article  CAS  Google Scholar 

  12. March, J., in “Advanced Organic Chemistry: Reaction, Mechanism, and Structure,” McGraw-Hill, New York, 1968, p. 496.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Food Science and Technology, University of California, 95616, Davis, California

    V. G. Malshet & L. Al Tappel

Authors
  1. V. G. Malshet
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. L. Al Tappel
    View author publications

    You can also search for this author in PubMed Google Scholar

About this article

Cite this article

Malshet, V.G., Al Tappel, L. Fluorescent products of lipid peroxidation: I. Structural requirement for fluorescence in conjugated schiff bases. Lipids 8, 194–198 (1973). https://doi.org/10.1007/BF02544634

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02544634

Keywords

Search

Navigation