Gas–liquid chromatography–mass spectrometry of hydroxy fatty acids as their methyl esters tert.-butyldimethylsilyl ethers

Chance, Deborah L.; Gerhardt, Klaus O.; Mawhinney, Thomas P.

doi:10.1016/s0021-9673(97)00876-5

Cited by 50 publications

(19 citation statements)

References 22 publications

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“…The ion at [M − 57] + is frequently the base peak in the spectra of saturated primary alcohols; m/z 75 (CH 3 ) 2 Si‐OH ( d ) is also abundant (Chance et al, ) and forms the base peak in the spectra of unsaturated primary alcohols (Chance et al, ; Mawhinney et al 1986; Dasgupta & Banerjee, ) and many derivatized fatty acids (Chance et al, ; Kim et al, ; Woollard, ; Woollard & Mallet, ). Secondary alcohols display α‐cleavage product ions (Woollard, ) as with the TMS derivatives.…”

Section: Other Silyl Derivativesmentioning

confidence: 99%

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Mass Spectrometric Fragmentation of Trimethylsilyl and Related Alkylsilyl Derivatives

Harvey

Vouros

2019

Mass Spectrometry Reviews

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This review describes the mass spectral fragmentation of trimethylsilyl (TMS) and related alkylsilyl derivatives used for preparing samples for analysis, mainly by combined gas chromatography and mass spectrometry (GC/MS). The review is divided into three sections. The first section is concerned with the TMS derivatives themselves and describes fragmentation of derivatized alcohols, thiols, amines, ketones, carboxylic acids and bifunctional compounds such as hydroxy‐ and amino‐acids, halo acids and hydroxy ethers. More complex compounds such as glycerides, sphingolipids, carbohydrates, organic phosphates, phosphonates, steroids, vitamin D, cannabinoids, and prostaglandins are discussed next. The second section describes intermolecular reactions of siliconium ions such as the TMS cation and the third section discusses other alkylsilyl derivatives. Among these latter compounds are di‐ and trialkyl‐silyl derivatives, various substituted‐alkyldimethylsilyl derivatives such as the tert‐butyldimethylsilyl ethers, cyclic silyl derivatives, alkoxysilyl derivatives, and 3‐pyridylmethyldimethylsilyl esters used for double bond location in fatty acid spectra. © 2019 Wiley Periodicals, Inc. Mass Spec Rev 0000:1–107, 2019

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Section: Other Silyl Derivativesmentioning

confidence: 99%

“…For other papers on TBDMS derivatives, see Chance et al (1998), (hydroxyl-fatty acids), Paik et al, (2006) (β-blockers), Mawhinney et al (1986), (mono-, di-and tricarboxylates), Hocart et al (1986) (cytokinin bases), Arkan et al (2016) (N-(phosphonomethyl)glycine, (glyphosate)).…”

Section: Ivd2 Tert-butyldimethylsilyl (Tbdms) Derivativesmentioning

confidence: 99%

Mass Spectrometric Fragmentation of Trimethylsilyl and Related Alkylsilyl Derivatives

Harvey

Vouros

2019

Mass Spectrometry Reviews

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“…Hydroxy fatty acids are found in triacylglycerols, waxes, cerebrosides, and other lipids in plants, insects, and microorganisms (Chance et al 1998). The hydroxy fatty acids of microorganisms, which are produced by the biotransformation of unsaturated fatty acids, are classified according to the number of hydroxy groups such as monohydroxy (Yamada et al 1996), dihydroxy (Hou et al 1991), and trihydroxy fatty acids (Kuo et al 2001).…”

Section: Introductionmentioning

confidence: 99%

Conversion of oleic acid to 10-hydroxystearic acid by whole cells of Stenotrophomonas nitritireducens

Kim

Yeom

2011

Biotechnol Lett

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The optimal reaction conditions for the conversion of oleic acid to 10-hydroxystearic acid by whole cells of Stenotrophomonas nitritireducens were: pH 7.5, 35 °C, 0.05% (w/v) Tween 80, 20 g cells l(-1), and 30 g oleic acid l(-1) in an anaerobic atmosphere. Under these conditions, the cells produced 31.5 g 10-hydroxystearic acid l(-1) over 4 h with a conversion yield of 100% (mol/mol) and a productivity of 7.9 g l(-1) h(-1), indicating that oleic acid was converted completely to 10-hydroxystearic acid, with no detectable byproduct. This is the highest concentration, productivity, and yield of 10-hydroxystearic acid from oleic acid reported thus far.

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“…Hydroxy fatty acids are important industrial materials because of their higher reactivity compared with that of other non‐hydroxylated fatty acids (1). Hydroxy fatty acids have been found as components of triacylglycerols, waxes, cerebrosides, and other lipids in plants, insects, and microorganisms (2). The hydroxy fatty acids of microorganisms, which are produced by biotransformation of unsaturated fatty acids, are classified into three types according to the number of hydroxy groups as monohydroxy (3), dihydroxy (4), and trihydroxy fatty acids (5).…”

Section: Introductionmentioning

confidence: 99%

Conversion of Linoleic Acid into 10-Hydroxy-12(Z)-octadecenoic Acid by Whole Cells of Stenotrophomonas nitritireducens

Yu¹,

Kim²,

Oh³

2008

Biotechnol. Prog.

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The conversion of linoleic acid into 10‐hydroxy‐12( Z)‐octadecenoic acid by whole cells of Stenotrophomonas nitritireducens as an isolated bacterium was optimized, and the optimal temperature, pH, and cell and substrate concentrations were 30 °C, 7.5, and 20 and 20 g/L, respectively. Under these conditions, whole cells in a bioreactor produced 15 g/L 10‐hydroxy‐12( Z)‐octadecenoic acid in 2 h of reaction time without detectable byproducts. Using 2 g/L linoleic acid, the cells produced 1.92 g/L 10‐hydroxy‐12( Z)‐octadecenoic acid. These are the highest concentration and yield of 10‐hydroxy‐12( Z)‐octadecenoic acid ever reported.

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Gas–liquid chromatography–mass spectrometry of hydroxy fatty acids as their methyl esters tert.-butyldimethylsilyl ethers

Cited by 50 publications

References 22 publications

Mass Spectrometric Fragmentation of Trimethylsilyl and Related Alkylsilyl Derivatives

Mass Spectrometric Fragmentation of Trimethylsilyl and Related Alkylsilyl Derivatives

Conversion of oleic acid to 10-hydroxystearic acid by whole cells of Stenotrophomonas nitritireducens

Conversion of Linoleic Acid into 10-Hydroxy-12(Z)-octadecenoic Acid by Whole Cells of Stenotrophomonas nitritireducens

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