What question did this study set out to answer?

To synthesize specifically labeled tetradeuterated methyl octadecatrienoate and methyl octadecatetraenoate fatty acid esters.

March 1, 1990Lipids

Preparation of deuterated methyl 6,9,12‐octadecatrienoates and methyl 6,9,12,15‐octadecatetraenoates

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Authors

HRHenry RakoffNational Center for Agricultural Utilization Research

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Implication

Experimental chemical study demonstrates the synthesis of deuterated polyunsaturated fatty acid methyl esters, suggesting viable pathways for isotopic tracing in lipid metabolism.

Key Points

To synthesize specifically labeled tetradeuterated methyl octadecatrienoate and methyl octadecatetraenoate fatty acid esters.
Prepared a common aldehyde ester intermediate, methyl 9-oxo-6-nonenoate, via cyclohexene ozonolysis and subsequent Wittig olefination.
Synthesized deuterated phosphonium iodide precursors through catalytic deuteration using deuterium gas with tris-(triphenylphosphine)chlororhodium or P-2 nickel catalysts.
Coupled intermediate fragments via Wittig reactions and isolated the target isomers using silver resin chromatography.
Successfully prepared methyl 6,9,12-octadecatrienoate-15,15,16,16-d4 through Wittig coupling between a tetradeuterated nonenylphosphonium salt and methyl 9-oxo-6-nonenoate.
Successfully synthesized methyl 6,9,12,15-octadecatetraenoate-12,13,15,16-d4 using Wittig coupling of a tetradeutero-nonadienylphosphonium salt with the aldehyde ester.
Achieved chromatographic separation of the targeted deuterated polyunsaturated esters from geometrical isomers using silver resin chromatography.

Cite This Study

Henry Rakoff (1990) studied this question.

synapsesocial.com/papers/6a99e7dd8548cd35f93fd540 https://doi.org/10.1007/bf02544326

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Implication

Experimental chemical study demonstrates the synthesis of deuterated polyunsaturated fatty acid methyl esters, suggesting viable pathways for isotopic tracing in lipid metabolism.

Preparation of deuterated methyl 6,9,12‐octadecatrienoates and methyl 6,9,12,15‐octadecatetraenoates

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Implication

Key Points

Cite This Study

Preparation of deuterated methyl 6,9,12‐octadecatrienoates and methyl 6,9,12,15‐octadecatetraenoates

Discussion

Member takes

Implication

Key Points

Cite This Study

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