Large‐scale preparation of linoleic acid‐d 2 ‐enriched triglycerides from Crepis alpina  seed oil | Zendy

Adlof Richard O. | Zendy; Emken Edward A. | Zendy

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Large‐scale preparation of linoleic acid‐d 2 ‐enriched triglycerides from Crepis alpina seed oil

Author(s) -

Adlof Richard O.,

Emken Edward A.

Publication year - 1993

Publication title -

journal of the american oil chemists' society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.512

H-Index - 117

eISSN - 1558-9331

pISSN - 0003-021X

DOI - 10.1007/bf02542609

Subject(s) - linoleic acid , chemistry , silica gel , fractionation , chromatography , hexane , triglyceride , extraction (chemistry) , gas chromatography , catalysis , organic chemistry , fatty acid , biochemistry , cholesterol

Catalytic deuteration of Crepis 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 (D 2 ) gas. Purification (silica gel) resulted in > 150‐g samples of triglyceride containing 74% cis ‐9, cis ‐12‐octadecadienoic acid‐12,13‐d 2 (18:2‐d 2 ) and 14% unlabelled linoleic acid. Pure (> 99%) tricrepenynin was recovered by further fractionation of the Crepis alpina triglycerides on silica gel. Deuteration of this sample produced deuteriumlabelled trilinolein containing linoleic acid‐d 2 of > 98% isotopic purity.

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