Furanoid fatty acids from fish lipids
- 1 November 1975
- Vol. 10 (11) , 695-702
- https://doi.org/10.1007/bf02532763
Abstract
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.Keywords
This publication has 29 references indexed in Scilit:
- Convenient synthesis of substituted furansJournal of the American Chemical Society, 1967
- Retroconversion of polyunsaturated fatty acids in vivo by partial degradation and hydrogenationBiochimica et Biophysica Acta (BBA) - Lipids and Lipid Metabolism, 1967
- Selective Reductions. XI. The Reaction of Sodium Borohydride with Alkyl Halides under Solvolytic Conditions. Borohydride as a Convenient Trap for Carbonium Ions1,2Journal of the American Chemical Society, 1966
- Darstellung von Polycarbonsäuren, II. Mitteil.): Die Aufspaltung des α‐substituierten Tetrahydrofuran‐Ringes in der AlkalischmelzeEuropean Journal of Inorganic Chemistry, 1954
- 125. ω-2′-Furylalkane derivativesJournal of the Chemical Society, 1953
- Steroidal Sapogenins. IX.1 Oxidation of Δ5,16,20(22)-Furostatriene-3β,26-diol2Journal of the American Chemical Society, 1951
- Mechanism of Lithium Aluminum Hydride ReactionsJournal of the American Chemical Society, 1949
- Catalytic Hydrogenation of Furan and Substituted Furans on PlatinumJournal of the American Chemical Society, 1949
- Hydrogenolysis of Alkyl Halides by Lithium Aluminum Hydride1Journal of the American Chemical Society, 1948
- Hydrogenation and Hydrogenolysis of Furan DerivativesJournal of the American Chemical Society, 1934