Furanoid fatty acids from fish lipids

• Published in: Lipids Vol. 10; no. 11; pp. 695 - 702
• Main Authors: Glass, Robert L., Krick, Thomas P., Sand, Donald M., Rahn, Curtis H., Schlenk, Hermann
• Format: Journal Article
• Language: English
• Published: Berlin/Heidelberg Springer‐Verlag 01.11.1975
• Subjects: Animals; Chromatography, Gas; Fatty Acids, Unsaturated - analysis; Fishes; Furans - analysis; Lasers; Magnetic Resonance Spectroscopy; Mass Spectrometry; Oxidation-Reduction; Scattering, Radiation; Spectrophotometry, Infrared; Spectrophotometry, Ultraviolet; Spectrum Analysis
• ISSN: 0024-4201; 1558-9307
• DOI: 10.1007/BF02532763

Fatty acids, recently reported as constitutents of certain fish lipids, were identified to be derivatives of furan (furanoid fish fatty acids). 12,15‐Epoxy‐13,14‐dimethyleicosa‐12,14‐dienoic acid is predominant among the furan acids and is associated withbis‐homologs in regard to chain length. Monomethyl acids, such as 12,15‐epoxy‐13‐methyleicosa‐12,14‐dienoic, are present in appreciable amounts. The structures were concluded from oxidative degradations, from mass spectrometry of methyl esters of the novel acids and fatty acids derived from them by opening the ring, and from nuclear magnetic resonance, infrared, and Raman spectra. The results from chemical procedures and from spectrometric methods were in aggreement with those obtained with authentic methyl 9,12‐epoxyoctadeca‐9,11‐dienoate. The number of substituents at the furan ring greatly influences hydrogenation, hydrogenolysis, and hydrolysis reactions of the ring.