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May 1, 1991Journal of the American Oil Chemists Society

Preparation of deuterium‐labelled methyl linoleate and its geometric isomers from natural seed oils

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To synthesize multi-gram quantities of deuterium-labelled methyl linoleate and its geometric isomers using precursors isolated from natural seed oils.
Natural oils from Crépis alpina and Vernonia galamensis provided fatty acid precursors, including cis-9-octadecen-12-ynoic acid and vernolic acid.
Synthesized d2-labelled isomers via Lindlar-catalyzed deuteration of alkynoate precursors.
Prepared d2-, d4-, and d6-labelled geometric isomers using stereocontrolled Wittig coupling of deuterated alkyltriphenylphosphonium salts with aldehyde intermediates derived from periodic acid cleavage.
Multi-gram yields of all four geometric isomers (cis-9,cis-12; trans-9,cis-12; cis-9,trans-12; and trans-9,trans-12) were successfully synthesized.
Isotopic purities reached 88% for the d6 isomers and up to 99% for the d2 isomers.

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Laboratory synthesis demonstrates multi-gram preparation of deuterium-labelled methyl linoleate isomers from natural seed oils, indicating efficient pathways for generating isotopically pure lipid...

Cite This Study

Adlof et al. (1991) studied this question.

synapsesocial.com/papers/6a6f3ebf31a3df824327a9af https://doi.org/10.1007/bf02657681

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Implication

Laboratory synthesis demonstrates multi-gram preparation of deuterium-labelled methyl linoleate isomers from natural seed oils, indicating efficient pathways for generating isotopically pure lipid...

Preparation of deuterium‐labelled methyl linoleate and its geometric isomers from natural seed oils

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Discussion

Implication

Cite This Study

Preparation of deuterium‐labelled methyl linoleate and its geometric isomers from natural seed oils

Key Points

Discussion

Implication

Cite This Study