Gemeinschaftsarbeiten der DGF, 101. Mitteilung Deutsche Einheitsmethoden zur Untersuchung von Fetten, Fettprodukten und verwandten Stoffen, 78. Mitt: Analyse von Fetten XXV/Analyse von fettreichen Lebensmitteln III

✍ Scribed by Arens, M. ;Gertz, Chr.

• Publisher: John Wiley and Sons
• Year: 1987
• Weight: 387 KB
• Volume: 89
• Category: Article
• ISSN: 0931-5985
• DOI: 10.1002/lipi.19870891105

✦ Synopsis

0 / \ -C=C-cH2-C-C-); 7.2 (ILH, m, cis-HC-CH-), 4.6 (2H, m,

-HC=CH-) and -0.8 offset (lH, s, COOH).

Methyl esters were prepared from the oil by saponification in alcoholic KOH followed by reaction with 10 Vo BF, in methanol.

Acetolysis of the epoxy acid (500 mg) was done in accordance with the method of Gunstone4. The resulting acid on successful crystallization from acetone-light petroleum (3 : 1, v/v) gave a crystalline product, m. p. 54-55' C, which was found undepressed on admixture with a reference sample of threo-12,13-dihydroxyoleic acid derived from K anthelmintica oil.

0.15 g of this dihydroxyoleic acid was hydrogenated in the presence of 10 Yo palladium on charcoal. The usual work-up yielded a white crystalline product identified as 12J3-dihydroxy-octadecanoic acid. It melted at 96-97' C, either alone or mixed with authentic threo-12,13-dihydroxyoctadecanoic acid prepared from Kanthelmintica oil.

The two diol acids were individually subjected to von Rudhff oxidation lo with specific modification in which t- butyl alcohol is used as co-solvent. The oxidation products were recovered, methylated and identified by GLC.