Identification of the position and the stereochemistry of the double bond in monounsaturated fatty acid methyl esters by gas chromatography/mass spectrometry of dimethyl disulfide derivatives
A single-step derivatization procedure using dimethyl disulfide (DMDS) is described for monounsaturated fatty acid esters (MUFAME). The analysis of DMDS adducts by gas chromatography/mass spectrometry is detailed: The mass spectra (electron impact 70 eV) show molecular ions (M/sup +/) and give key fragments that permit determination of the position of the original double bond. Alkylthiolation of Z- and E-MUFAME as a specific antiaddition leads, respectively, to the threo and erythro adducts. The two isomers are well-separated by gas chromatography, permitting precise stereochemistry of the initial double bond. Nevertheless, for a complex environmental mixture of MUFAME, the stereochemical identification is restricted to the linear series. This procedure is suitable for the analysis of trace compounds at the nanogram level such as encountered in the natural environment. An application is presented for the analysis of planktonic and bacterially derived fatty acids in recent marine sediments.
- Research Organization:
- Universite Pierre et Marie Curie, Paris (France)
- OSTI ID:
- 6978016
- Journal Information:
- Anal. Chem.; (United States), Vol. 60:9
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
ORGANIC
PHYSICAL AND ANALYTICAL CHEMISTRY
54 ENVIRONMENTAL SCIENCES
CARBOXYLIC ACID ESTERS
GAS CHROMATOGRAPHY
MASS SPECTROSCOPY
SEDIMENTS
QUALITATIVE CHEMICAL ANALYSIS
DERIVATIZATION
DISULFIDES
DOUBLE BONDS
EXPERIMENTAL DATA
STEREOCHEMISTRY
TRACE AMOUNTS
CHEMICAL ANALYSIS
CHEMICAL BONDS
CHEMICAL REACTIONS
CHROMATOGRAPHY
DATA
ESTERS
INFORMATION
NUMERICAL DATA
ORGANIC COMPOUNDS
ORGANIC SULFUR COMPOUNDS
SEPARATION PROCESSES
SPECTROSCOPY
400102* - Chemical & Spectral Procedures
400201 - Chemical & Physicochemical Properties
510200 - Environment
Terrestrial- Chemicals Monitoring & Transport- (-1989)