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Furanoid fatty acids from fish lipids
Author(s) -
Glass Robert L.,
Krick Thomas P.,
Sand Donald M.,
Rahn Curtis H.,
Schlenk Hermann
Publication year - 1975
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1007/bf02532763
Subject(s) - furan , chemistry , hydrogenolysis , ring (chemistry) , hydrolysis , organic chemistry , fish <actinopterygii> , fatty acid , mass spectrometry , catalysis , chromatography , fishery , biology
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 with bis ‐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.