Ro. Adlof et Ea. Emken, LARGE-SCALE PREPARATION OF LINOLEIC ACID-D2-ENRICHED TRIGLYCERIDES FROM CREPIS-ALPINA SEED OIL, Journal of the American Oil Chemists' Society, 70(8), 1993, pp. 817-819
Catalytic deuteration of Crepis alpina seed oil provided a convenient
one-step method for the direct synthesis of large quantities of trigly
cerides enriched with deuterium-labelled linoleic acid. Crepis alpina
seed (19 kg) was crushed, and the oil [74% crepenynic acid (cis-9-octa
decen-12-ynoic acid)] was extracted with hexane. After purification by
column chromatography (silica gel), > 170-g batches of oil were deute
rated with Lindlar catalyst and deuterium (D2) gas. Purification (sili
ca 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 fra
ctionation of the Crepis alpina triglycerides on silica gel. Deuterati
on of this sample produced deuterium-labelled trilinolein containing l
inoleic acid-d2 of > 98% isotopic purity.