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Synthesis of Linoleic Acid Hydroperoxides as Flavor Precursors, Using Selected Substrate Sources

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Journal of the American Oil Chemists' Society

Abstract

The objective of the research was the synthesis of linoleic acid hydroperoxides (HPOD) and their recovery, using selected sources of linoleic acid (LA) as substrate. This is part of on-going work aimed at the development of an economically viable biotechnological process for the production of natural flavors. The investigated sources included pure (100 %) LA and commercial (67 %) LA as well as safflower oil (SO) and its hydrolyzed product. A model describing commercial LA oxidation by lipoxygenase, based on Michaelis–Menten kinetics, was developed. The conversion of pure LA and commercial LA resulted in insignificant differences in HPOD yield of 69.7 and 68.9 %, respectively. However, there was a significant difference in the HPOD yield, obtained from the SO (2.0 %) and that from the hydrolyzed SO (58.0 %) in comparison to that from pure LA (69.7 %). The ratios of the different 9- and 13-HPOD isomers were insignificantly different for the sources containing free LA, with 13-(9Z,11E)-HPOD was the highest relative percentage. Using optimized conditions, HPOD yields were 85.9 and 74.0 % for the commercial LA and the hydrolyzed SO, respectively. Based on experimental findings, commercial (67 %) LA was selected as the most appropriate alternative to pure LA for the production of HPOD. An efficient extraction procedure for the recovery of HPOD was also developed.

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Acknowledgments

This research was supported by a Discovery Grant from the Natural Sciences and Engineering Research Council of Canada (NSERC). Marya Aziz was the recipient of a M.Sc. graduate student fellowship, from the Fonds de Recherche sur la Nature et les Technologies (FQRNT) as well as a Ph.D. graduate fellowship, awarded by the NSERC.

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Authors and Affiliations

  1. Department of Food Science and Agricultural Chemistry, McGill University, 21,111 Lakeshore, Ste-Anne de Bellevue, QC, H9X 3V9, Canada

    Marya Aziz & Selim Kermasha

  2. Institut National de Recherche et d’Analyse Physico-chimique (INRAP), Pôle Technologique, Sidi Thabet, 2020, Tunis, Tunisia

    Najla Ben Akacha

  3. Laboratoire de Génie des Procédés Microbiologiques et Alimentaires (GPMA), AgroSup Dijon, 1, Esplanade Erasme, 21,000, Dijon, France

    Florence Husson

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  1. Marya Aziz
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  2. Najla Ben Akacha
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  3. Florence Husson
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  4. Selim Kermasha
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Correspondence to Selim Kermasha.

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Aziz, M., Ben Akacha, N., Husson, F. et al. Synthesis of Linoleic Acid Hydroperoxides as Flavor Precursors, Using Selected Substrate Sources. J Am Oil Chem Soc 91, 1867–1876 (2014). https://doi.org/10.1007/s11746-014-2543-x

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  • DOI: https://doi.org/10.1007/s11746-014-2543-x

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