Identification of (all-cis)-6,9,12,15-octadecatetraenoic acid in Ribes nigrum and fish oils: chemical and physical characterization.
In this report, we show that the non-conjugated octadecatetraenoic acid found in the oil of the seeds from Ribes nigrum is identical to the C18-polyunsaturated fatty acid previously isolated in a number of fish oils and seed oils. Evidence obtained from mass spectral data of its triazolopyridine derivative clearly indicates the presence of methylene-interrupted double bonds. Comparison with authentic material prepared by chemical synthesis provides further confirmation of the (all-cis)-6,9,12,15-octadecatetraenoic acid structure. The (all-cis)-4,8,12,15-structural arrangement erroneously attributed to this acid in several literature reports is thus definitely ruled out.
Moine
G
G
Vitamin and Nutrition Research, Analytical Department, F. Hoffmann-La Roche Ltd., Basel, Switzerland.
Forzy
L
L
Oesterhelt
G
G
D002247:Carbon Isotopes; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D002849:Chromatography, Gas; D005231:Fatty Acids, Unsaturated / Q000138:chemical synthesis / Q000737:chemistry*; D005395:Fish Oils / Q000737:chemistry*; D008401:Gas Chromatography-Mass Spectrometry; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D010944:Plants / Q000737:chemistry*; D012639:Seeds / Q000737:chemistry
D002247:Carbon Isotopes; D005231:Fatty Acids, Unsaturated; D005395:Fish Oils; C013641:parinaric acid