Abstract
An emulsion of methyl linolenate was allowed to oxidize with a catalyst of ferrous sulfate and ascorbic acid. Three oxidation products were isolated, and their hydrogenated derivatives were characterized as the isomeric mixture of methyl monohydroxyoctadecanoate (monoOH), methyl 9,16-dihydroxyoctadecanoate (diOH), and the isomeric mixture of methyl trihydroxyoctadecanoate (triOH). The monoOH isomers and diOH apparently were derived from methyl monohydroperoxyoctadecatrienoate (monoHPO) and methyl dihydroperoxyoctadecatrienoate (diHPO), respectively. Two triOH isomers (the 9,10,12- and 13,15,16-isomers) were thought to be derived from the products containing cyclic peroxide-hydroperoxide structure. 9,16-diHPO was produced by the incubation of monoHPO with ferrous sulfate and ascorbic acid. Moreover, the experiment using18O2 demonstrated that mono-HPO yielded 9,16-diHPO by reacting with oxygen molecule. 9,10,13- and/or 9,12,13- and 12,13,16- and/or 12,15,16-triOH isomers were also detected in the hydrogenated derivatives of oxidation products from monoHPO.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Waters, W.A. (1971), J. Am. Oil Chem. Soc. 48, 427–433.
Tappel, A.L. (1953) Food Res. 18, 104–108.
Tappel, A.L. (1955) J. Biol. Chem. 217, 721–733.
Younathan, M.T., and Watts, B.M. (1959) Food Res. 24, 728–734.
Love, J.D., and Pearson, A.M. (1974) J. Agric. Food Chem. 22, 1032–1034.
Kwoh, T.L. (1971) J. Am. Oil Chem. Soc. 48, 550–555.
Wills, E.D. (1965) Biochim. Biophys. Acta 98, 238–251.
Chan, H.W.-S., and Newby, V.K. (1980) Biochim. Biophys. Acta 617, 353–362.
Hamberg, M. (1975) Lipids 10, 87–92.
Gardner, H.W., Kleiman, R., and Weisleder, D. (1974) Lipids 9, 696–706.
Gardner, H.W., Weisleder, D., and Kleiman, R. (1978) Lipids 13, 246–252.
Carrol, K.K. (1961) J. Lipid Res. 2, 135–141.
Terao, J., and Matsushita, S. (1975) Agric. Biol. Chem. 39, 397–402.
Terao, J., and Matsushita, S. (1975) Agric. Biol. Chem. 39, 2027–2033.
Terao, J., Hirota, Y., and Matsushita, S. (1981) J. Jpn. Oil Chem. Soc. 30, 10–14.
Terao, J., and Matsushita, S. (1977) J. Am. Oil Chem. Soc. 54, 234–238.
Terao, J., and Matsushita, S. (1981) Agric. Biol. Chem. 45, 587–593.
Frankel, E.N., Neff, W.E., Khambay, B.P.S., Garwood, R.F., and Weedon, B.C.L. (1977) Lipids 12, 901–907.
Frankel, E.N., Evans, C.D., McConnel, D.G., Selke, E., and Dutton, H.J. (1961) J. Org. Chem. 26, 4663–4669.
Frankel, E.N., Neff, W.E., Rohwedder, W.K., Khambay, B.P.S., Garwood, R.F., and Weedon, B.C.L. (1977) Lipids 12, 1055–1061.
Begemann, P.H., Woestenberg, W.J., and Leers, S. (1968) J. Agric. Food Chem. 16, 679–684.
Gerristsen, M., Veldink, G.A., Vliegenthart, J.F.G., and Boldingh, J. (1976) FEBS Lett. 67, 149–152.
Pryor, W.A., Stanley, J.P., and Brair, E. (1976) Lipids 11, 370–379.
Frankel, E.N. (1962) in Lipids and Their Oxidation (Schultz, H.W. ed.) pp. 51–78, AVI Publishing Co., Westport, CT.
Neff, W.E., Frankel, E.N., and Weisleder, D. (1981) Lipids 16, 439–448.
Author information
Authors and Affiliations
About this article
Cite this article
Toyoda, I., Terao, J. & Matsushita, S. Hydroperoxides formed by ferrous ion-catalyzed oxidation of methyl linolenate. Lipids 17, 84–90 (1982). https://doi.org/10.1007/BF02535180
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF02535180