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

Scribe, P.; Guézennec, Jean; Dagaut, J.; Pèpe, Claude; Saliot, A.

doi:10.1021/ac00160a019

Cited by 140 publications

(101 citation statements)

References 18 publications

(25 reference statements)

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“…They were identified by gas chromatography/mass spectometry (ionization energy 70 eV, source temperature 170°C) and quantified at a 10% precision level by using authentic standards and n-C23:1 acid as internal standard. The positions of the double bonds in the monounsaturated fatty acids were determined by gas chromatography/mass spectometry after derivatization with dimethyldisulfide according to Scribe et al (1988).…”

Section: Momzikoff Et Almentioning

confidence: 99%

Field study of the chemical characterization of the upper ocean surface using various samplers

Momzikoff

Brinis

Dallot

et al. 2004

Limnology & Ocean Methods

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The sea surface microlayer (SML) is the seawater layer (about 100 µm thick) located at the air-ocean interface, usually enriched in organic and inorganic matter compared to the underlying water (UW) sampled between 5 cm and 50 cm depth. This article is aimed at providing novel data for a better quantification of the SML enrichment and knowledge of associated processes. First, the mean 1 to 100 cm depth profile for dissolved total carbohydrates (DTCHO) established from a set of 10 stations in coastal northwestern Mediterranean waters (off Barcelona and Banyuls-sur-mer) indicates that (1) this layer is not necessarily homogeneous as generally admitted and (2) an exploratory survey is needed before undertaking an extensive sampling, to determine the most appropriate depth for sampling UW. Second, two samplers, glass plate (GP) and metal screen (MS), are compared for their ability to collect several classes of biomolecules at the first 50 µm and 440 µm layers below the interface, respectively. GP is shown to collect more efficiently (1) hydrophobic amino acids and phytoplanktonderived detrital matter, as shown by statistical results on a set of eight stations, and (2) fatty acids originating from bacteria and continental higher plants (inferred from a lower number of stations). Thus, it is well adapted for studying interactions between ocean, atmosphere, and continent. On the contrary, MS is better adapted for recovering phytoplankton organisms, as shown by data for chlorophyll a, pheophytin a, and unsaturated fatty acids. DTCHO are equally sampled by GP and MS.

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Section: Momzikoff Et Almentioning

confidence: 99%

Field study of the chemical characterization of the upper ocean surface using various samplers

Momzikoff

Brinis

Dallot

et al. 2004

Limnology & Ocean Methods

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“…MS of fatty acid methyl esters (FAMEs), on the other hand, are believed to provide little structural information such as the position and geometry of double bonds [9]. Pyrrolidide, picolinyl, and dimethyl oxazoline derivatives [10], double-bond deuteration, silylation [11], and preparation of dimethyl disulfide adducts [12] are among the derivatization methods used for the determination of double-bond positions. While many studies have been made on the determination of the position of double bonds, there are very few reports on identification of the geometry of double bonds in fatty acids using mass spectrometry [9,[13][14][15][16][17][18][19][20][21].…”

mentioning

confidence: 99%

Discrimination among geometrical isomers of α-linolenic acid methyl ester using low energy electron ionization mass spectrometry

Hejazi

Ebrahimi

Guilhaus

et al. 2009

J. Am. Soc. Mass Spectrom.

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There is a consensus that electron impact ionization mass spectrometry is not capable of discriminating among geometrical isomers of unsaturated fatty acid methyl esters (and in general olefinic compounds). In this paper, we report the identification of all eight geometrical isomers of ␣-linolenic acid, one of the few essential -3 fatty acids that has attracted great attention, using low-energy electron ionization mass spectrometry. Three electron energies 70, 50, and 30 eV were studied and the mass spectrum of each isomer was obtained from the analysis of different concentrations of a standard mixture of ␣-linolenic acid methyl ester geometrical isomers to ensure the robustness of the method. Principal component analysis was employed to model the complex variation of m/z intensities across the isomers. Only using the data of 30 eV energy was complete differentiation among geometrical isomers observed. The unique cleavage pattern of the ␣-linolenic acid methyl ester isomers leading to a benzenium ion structure is discussed and general fragmentation rules are derived using the mass spectra of over 300 compounds with different kinds and levels of unsaturation. Application of the proposed method is not limited to ␣-linolenic acid. It can potentially be used to identify the geometrical isomers of any compounds with an olefinic chain. (J Am Soc Mass Spectrom 2009, 20, 1272-1280

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“…This was not always the case for the other acids of the secretion. The most reliable results were obtained by the mass spectra of dimethyl disulfide (DMDS) adducts (10) of the unsaturated methyl esters [22,23] The individual acids were identified by interpretation of the mass spectra of the derivatives as just discussed, according to well established rules [22,[24][25][26][27][28][29], and by correlation with gas chromatographic retention indices I [18,30]. Over 100 acids were identified.…”

Section: Fatty Acidsmentioning

confidence: 99%

Scent gland constituents of the Middle American burrowing python, Loxocemus bicolor (Serpentes: Loxocemidae)

Schulze

Weldon

Schulz

2017

Zeitschrift Für Naturforschung C

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Analysis by gas chromatography/mass spectrometry of the scent gland secretions of male and female Middle American burrowing pythons (Loxocemus bicolor) revealed the presence of over 300 components including cholesterol, fatty acids, glyceryl monoalkyl ethers, and alcohols. The fatty acids, over 100 of which were identified, constitute most of the compounds in the secretions and show the greatest structural diversity. They include saturated and unsaturated, unbranched and mono-, di-, and trimethyl-branched compounds ranging in carbonchain length from 13 to 24. The glyceryl monoethers possess saturated or unsaturated, straight or methylbranched alkyl chains ranging in carbon-chain length from 13 to 24. Alcohols, which have not previously been reported from the scent glands, possess straight, chiefly saturated carbon chains ranging in length from 13 to 24. Sex or individual differences in secretion composition were not observed. Compounds in the scent gland secretions of L. bicolor may deter offending arthropods, such as ants.

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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

Cited by 140 publications

References 18 publications

Field study of the chemical characterization of the upper ocean surface using various samplers

Field study of the chemical characterization of the upper ocean surface using various samplers

Discrimination among geometrical isomers of α-linolenic acid methyl ester using low energy electron ionization mass spectrometry

Scent gland constituents of the Middle American burrowing python, Loxocemus bicolor (Serpentes: Loxocemidae)

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