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Autoxidation of the furan fatty acid ester, methyl 9,12-epoxyoctadeca-9,11-dienoate

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Journal of the American Oil Chemists' Society

Abstract

The objective of this study was to identify autoxidation products of methyl 9,12-epoxyoctadeca-9,11-dienoate (F9,12). Previous work has shown that F9,12 is a product both of autoxidation and singlet oxygen oxidation of the methyl ester derivative of conjugated linoleic acid (CLA). F9,12, 95% pure, was synthesized from methyl ricinoleate. The synthetic F9,12 was heated at 50°C in sealed tubes containing air. Each tube contained 6 mg F9,12 and 1 mg methyl stearate as an internal standard. Samples were taken at 4.5, 7, 23, 46.5, 69.5, and 93 h. The oxidized F9,12 was dissolved in isooctane and analyzed by gas chromatography (GC), GC-direct deposition-Fourier transform infrared spectroscopy, and GC-electron ionization mass spectrometry. CLA methyl ester was oxidized in a similar manner. Under these conditions, the half-lives of CLA and F9,12 were 40 and 35 h, respectively. Oxidation products of F9,12 that were identified included: 5-hexyl-2-furaldehyde (I), methyl 8-oxooctanoate (II), methyl 13-oxo-9,12-epoxytrideca-9,11-dienoate (III), methyl 8-oxo-9,12-epoxy-9,11-octadecadienoate (IV), and methyl 13-oxo-9,12-epoxy-9,11-octadecadienoate (V).

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Authors and Affiliations

  1. Center for Food Safety and Applied Nutrition, Office of Food Labeling (HFS-175), Food and Drug Administration, 200 C St., S.W., 20204, Washington, DC

    N. Sehat, M. P. Yurawecz, J. A. G. Roach, M. M. Mossoba, K. Eulitz, E. P. Mazzola & Y. Ku

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  1. N. Sehat
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  2. M. P. Yurawecz
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  3. J. A. G. Roach
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  4. M. M. Mossoba
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  5. K. Eulitz
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  6. E. P. Mazzola
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  7. Y. Ku
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Sehat, N., Yurawecz, M.P., Roach, J.A.G. et al. Autoxidation of the furan fatty acid ester, methyl 9,12-epoxyoctadeca-9,11-dienoate. J Amer Oil Chem Soc 75, 1313–1319 (1998). https://doi.org/10.1007/s11746-998-0177-6

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  • DOI: https://doi.org/10.1007/s11746-998-0177-6

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