Large-scale preparation of linoleic acid-d2-enriched triglycerides fromCrepis alpina seed oil

  • Richard O. Adlof
  • Edward A. Emken
Short Communication


Catalytic deuteration ofCrepis alpina seed oil provided a convenient one-step method for the direct synthesis of large quantities of triglycerides enriched with deuteriumlabelled linoleic acid.Crepis alpina seed (19 kg) was crushed, and the oil [74% crepenynic acid (cis-9-octadecen-12-ynoic acid)] was extracted with hexane. After purification by column chromatography (silica gel), > 170-g batches of oil were deuterated with Lindlar catalyst and deuterium (D2) gas. Purification (silica gel) resulted in > 150-g samples of triglyceride containing 74%cis-9,cis-12-octadecadienoic acid-12,13-d2 (18:2-d2) and 14% unlabelled linoleic acid. Pure (> 99%) tricrepenynin was recovered by further fractionation of theCrepis alpina triglycerides on silica gel. Deuteration of this sample produced deuteriumlabelled trilinolein containing linoleic acid-d2 of > 98% isotopic purity.

Key words

Acetylenic fatty acids and esters C18 fatty acids and derivatives crepis oil seeds and crepenynic acid deuterium and deuteration linoleic acid and esters 


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Copyright information

© American Oil Chemists’ Society 1993

Authors and Affiliations

  • Richard O. Adlof
    • 2
  • Edward A. Emken
    • 2
  1. 1.USDA, ARS, NCAURPeoria
  2. 2.USDA, ARS, Food Quality and Safety Research UnitPeoria

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