1H NMR study of methyl linoleate ozonation

Maritza F. Díaz, Frank Hernández, Oscar Ledea, José A. Gavín Sazatornil, Jesús Moleiro

Research output: Contribution to journalArticlepeer-review

17 Citations (Scopus)


Unsaturated fatty acids are essential components of vegetable oils and cellular membranes and the involved aspect of unsaturated fatty acids ozonation have been widely studied by different authors. In this paper, in vitro ozonolysis of unsaturated fatty acids with addition of water or ethanol has been studied by Proton Nuclear Magnetic Resonance (1H NMR) at 250 MHz in order to explore the possibility of this technique for the detection of Criegee ozonides in characterizing ozone reaction with these substrates. The ozonolysis of methyl linoleate showed that signal intensities from formed ozonides were increased with ozone concentration increments. However, the signal intensities with addition of water were higher than those in ethanol addition. Signal intensities from olefinic double bonds were found to decrease with the increment in ozonide signals. Thus, a correspondence of thee behavior of these signals is observed with a proportional rate reaction between the number of double bonds in the substrate molecule. Signals from aldehyde formation were poorly detected at lower ozone concentration. It was concluded that the evaluation of ozonide and olefinic double bond signals from 250 MHz 1H NMR can be a useful tool in assessing ozone reaction with biomolecules. The reaction mechanism for the ozone reaction with unsaturated fatty acids in the presence of water or ethanol is analyzed.

Original languageEnglish
Pages (from-to)121-126
Number of pages6
JournalOzone: Science and Engineering
Issue number2
Publication statusPublished - 2003
Externally publishedYes


  • H NMR
  • Methyl Linoleate
  • Ozone
  • Ozonides
  • Sunflower Oil

ASJC Scopus subject areas

  • Environmental Engineering
  • Environmental Chemistry


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