Skip to main content
SpringerLink
Log in

Fatty acid amides and anilides, syntheses and antimicrobial properties

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

Abstract

A series of fatty acid amides anilides was prepared and a number of compounds in the series were found to be highly active against gram positive bacteria but ineffective against gram negative organisms. The N,N-dimethyl- and N,N-diethylamides of C12-C14 fatty acids had minimal inhibitory concentration (MIC) values of 100 ppm or less. Substituted anilides of C6-C11 fatty acids were active when the following groups were attached to the aromatic ring: 3,4-dichloro, 3-nitro, 4-nitro, 5-chloro-2-hydroxy, 4-chloro-3-nitro, and 2-hydroxy-5-nitro. Some of these compounds had a MIC value of 0.1 ppm. Significantly, the presence of soap did not reduce the activity of these bacteriostats, whereas polysorbate 80 at high concentrations deactivated the compounds.

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. Ralston, A.W., “Fatty Acids and Their Derivatives”, Wiley, New York 1948, p. 582.

    Google Scholar 

  2. Markley, K.S., “Fatty Acids,” Interscience Publishers, New York 1964, Part 3, p. 1551.

    Google Scholar 

  3. Pattison, E.S., “Fatty Acids and their Industrial Applications,” Marcel Dekker Inc., New York, 1968, p. 77.

    Google Scholar 

  4. Mitchell, J.A., and E.E. Reid, J. Am. Chem. Soc. 53:1879 (1931).

    Article  CAS  Google Scholar 

  5. D'Alelio, G.F., and E.E. Reid, Ibid. 59:111 (1937).

    Article  Google Scholar 

  6. Robertson, P.W., J. Chem. Soc. 93:1033 (1908); 115: 1210 (1919).

    CAS  Google Scholar 

  7. Novak, A.F., J.M. Solar, R.R. Mod, F.C. Magne, and E.L. Skau, JAOCS 46:249 (1968).

    Article  Google Scholar 

  8. Novak, A.F., J.M. Solar, R.R. Mod, F.C. Magne, and E.L. Skau, Appl. Microbiol. 18:1050 (1969).

    CAS  Google Scholar 

  9. Kabara, J.J., A.J. Conely, and J.P. Truant, Antimicrob. Agents Chemother. 2:492 (1972).

    CAS  Google Scholar 

  10. Baker, J.W., U.S. 3,418,345, (Monsanto Co.), December 24, 1968.

  11. Wilson, H.F., and D.H. McRae, U.S. 3,816,092, (Rohm & Haas Co.), June 11, 1974.

  12. Good, N.E., Plant Physiol. 36:788 (1961).

    Article  CAS  Google Scholar 

  13. Moreland, D.E., and K.L. Hill, Weeds 11:55 (1963).

    CAS  Google Scholar 

  14. Beaver, D.J., D.R. Roman, and P.J. Stoffel, J. Am. Chem. Soc. 79:1236 (1957).

    Article  CAS  Google Scholar 

  15. Linfield, W.M., R.E. Casely, and D.R. Noel, JAOCS 37:251 (1960).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Eastern Regional Research Center, 19118, Philadelphia, PA

    R. G. Bistline {jrJr.}, E. W. Maurer, F. D. Smith & W. M. Linfield

Authors
  1. R. G. Bistline {jrJr.}
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. E. W. Maurer
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. F. D. Smith
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. W. M. Linfield
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Agricultural Research, Science and Education Administration, U.S. Department of Agriculture.

About this article

Cite this article

Bistline {jrJr.}, R.G., Maurer, E.W., Smith, F.D. et al. Fatty acid amides and anilides, syntheses and antimicrobial properties. J Am Oil Chem Soc 57, 98–103 (1980). https://doi.org/10.1007/BF02674376

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02674376

Keywords

Search

Navigation