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Determination of Double Bond Positions and Geometry of Methyl Linoleate Isomers with Dimethyl Disulfide Adducts by GC/MS

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Lipids

Abstract

The dimethyl disulfide (DMDS) adduct method is one of the convenient and effective methods for determining double bond positions of unsaturated fatty acid methyl esters (FAME) except conjugated FAME. When analyzed using gas chromatography/electron ionization-mass spectrometry (GC/EI-MS), unsaturated FAME with DMDS added to the double bonds yields high intensity MS spectra of characteristic ions. The MS spectra of characteristic ions can then be used to easily confirm double bond positions. Here we explore the GC/EI-MS analysis of the DMDS adducts of methyl linoleate geometrical isomers isolated by high performance liquid chromatography (HPLC) with a silver nitrate column. For C18:2-c9, c12 and C18:2-t9, t12, DMDS randomly formed adducts with double bonds at either carbon 9–10 or carbon 12–13, but not both at the same time due to steric hindrance. For C18:2-c9, t12 and C18:2-t9, c12, however, DMDS only formed adducts with the double bond in the cis configuration. Consequently, when analyzing fatty acids with methylene interrupted double bonds, with one double bond in the cis and one in the trans configuration, double bond positions cannot be completely confirmed.

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Fig. 1
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Abbreviations

FAME:

Fatty acid methyl ester(s)

DMDS:

Dimethyl disulfide

GC/EI-MS:

Gas chromatography/electron ionization-mass spectrometry

HPLC:

High performance liquid chromatography

C18:2ME:

Octadecadienoic acid methyl ester(s)

GC:

Gas chromatography

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Acknowledgments

We are grateful to Dr. Andrew Gooley and Mr. Wenjian Lu for helpful discussions on this study.

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Authors and Affiliations

  1. Shimadzu Corporation, 3-9-4, Hikaridai, Seika-cho, Soraku-gun, Kyoto, 619-0237, Japan

    Shigeaki Shibamoto

  2. Shimadzu Corporation, 1 Nishinokyo Kuwabara-cho, Nakagyo-ku, Kyoto, 604-8511, Japan

    Tasuku Murata

  3. Osaka Prefecture University, 3-7-30 Habikino city, Osaka, 583-8555, Japan

    Kouhei Yamamoto

Authors
  1. Shigeaki Shibamoto
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  2. Tasuku Murata
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  3. Kouhei Yamamoto
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Correspondence to Shigeaki Shibamoto.

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Shibamoto, S., Murata, T. & Yamamoto, K. Determination of Double Bond Positions and Geometry of Methyl Linoleate Isomers with Dimethyl Disulfide Adducts by GC/MS. Lipids 51, 1077–1081 (2016). https://doi.org/10.1007/s11745-016-4180-7

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  • DOI: https://doi.org/10.1007/s11745-016-4180-7

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