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A simple method of preparation of methyl trans-10,cis-12- and cis-9,trans-11-octadecadienoates from methyl linoleate

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Journal of the American Oil Chemists' Society

Abstract

Pure conjugated isomers of linoleic acid were prepared on a large scale by alkali-isomerization of purified methyl linoleate. The methyl esters of alkali-isomerized linoleic acid contained mainly the methyl cis-9,trans-11- and trans-10,cis-12-octadecadienoates (44 and 47%, respectively). These two isomers were then separated and purified by a series of low-temperature crystallizations from acetone. The isomeric purity obtained for the cis-9,trans-11-octadecadienoate isomer was >90% and that of the trans-10,cis-12-octadecadienoate isomer was 89 to 97%. The isolated yield of the two isomers corresponded to 18 and 25.7%, respectively, of the starting material. The structure of the two isomers was confirmed using partial hydrazine reduction, silver nitrate-thin-layer chromatography of the resulting monoenes and gas chromatography coupled with mass spectrometry of the 4,4-dimethyloxazoline derivatives. Fourier transform infrared spectroscopy of the monoenes gave the confirmation of the geometry of each double bond.

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Authors and Affiliations

  1. INRA, Unité de Nutrition Lipidique, 17 rue de Sully, BV 1540, 21034, Dijon Cedex, France

    O. Berdeaux, L. Voinot, E. Angioni, P. Juanéda & J. L. Sébédio

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  1. O. Berdeaux
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  2. L. Voinot
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  3. E. Angioni
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  4. P. Juanéda
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  5. J. L. Sébédio
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Correspondence to O. Berdeaux.

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Berdeaux, O., Voinot, L., Angioni, E. et al. A simple method of preparation of methyl trans-10,cis-12- and cis-9,trans-11-octadecadienoates from methyl linoleate. J Amer Oil Chem Soc 75, 1749–1755 (1998). https://doi.org/10.1007/s11746-998-0327-x

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  • DOI: https://doi.org/10.1007/s11746-998-0327-x

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