Some physical, chemical, and biological properties of natural and synthetic unsaturated C18 acids.
作者： F. D. Gunstone
DOI: 10.1007/BF02639866
关键词: Degree of unsaturation 、 Thin-layer chromatography 、 NMR spectra database 、 Cyclopropane 、 Chemical reaction 、 Melting point 、 Organic chemistry 、 Linoleic acid 、 Chemistry 、 Gas chromatography
摘要: Series of octadecenoic (cis andtrans), octadecynoic, octadecadienoic (cis,cis andtrans,trans), and octadecadiynoic acids have been synthesized employed in a comparative study some physical (melting point, Raman spectra, NMR Ag+ thin layer chromatography, gas liquid chromatography) biological properties. The results show that the position unsaturation has considerable influence on properties isomeric unsaturated acids. Several chemical reactions linoleic acid related oxygenated ricinoleic or vernolic (12,13-epoxyoleic) furnish cyclopropane compounds 1,4- (or 1,5-) epoxides. formation these is rationalized terms neighboring group participation. oxymercuration-demercuration reaction basis new method examining with Δ3, Δ4, Δ5 unsaturation.
springer.com
sci-hub.se 参考文章(33)
G.G. Abbot, F.D. Gunstone, S.D. Hoyes, Fatty acids, part 27: The formation of 1,4-epoxides from methyl linoleate and related esters by reaction with toluene-p-sulphonic acid and an appropriate solvent☆ Chemistry and Physics of Lipids. ,vol. 4, pp. 351- 366 ,(1970) , 10.1016/0009-3084(70)90035-6
F.D. Gunstone, R.P. Inglis, Fatty acids, part 39: Oxymercuration-demercuration of unsaturated alcohols. A new procedure for the identification, isolation, and estimation of Δ3t, Δ4, and Δ5 alkenols and of substances reducible thereto Chemistry and Physics of Lipids. ,vol. 10, pp. 105- 113 ,(1973) , 10.1016/0009-3084(73)90044-3
F.D. Gunstone, R.P. Inglis, Fatty acids, part 37 Chemistry and Physics of Lipids. ,vol. 10, pp. 73- 88 ,(1973) , 10.1016/0009-3084(73)90042-X
F.D. Gunstone, R.P. Inglis, Fatty acids, part 38: Neighbouring group participation in the oxymercuration-demercuration reaction. Another route to 1,4- and 1,5-epoxides Chemistry and Physics of Lipids. ,vol. 10, pp. 89- 104 ,(1973) , 10.1016/0009-3084(73)90043-1
F.D. Gunstone, A.I. Said, Fatty acids, part 29: Methyl 12-mesyloxyoleate as a source of cyclopropane esters and of conjugated octadecadienoates☆ Chemistry and Physics of Lipids. ,vol. 7, pp. 121- 134 ,(1971) , 10.1016/0009-3084(71)90026-0
F.D. Gunstone, B.S. Perera, Fatty acids, Part 41: The halogenation of some long-chain hydroxy alkenes with special reference to the possibility of neighbouring group participation leading to cyclic ethers or lactones Chemistry and Physics of Lipids. ,vol. 11, pp. 43- 65 ,(1973) , 10.1016/0009-3084(73)90051-0
H.B.S. Conacher, F.D. Gunstone, Fatty acids, part 21: The rearrangement of methyl 12, 13-epoxyoleate by boron trifluoride with formation of cyclopropane esters Chemistry and Physics of Lipids. ,vol. 3, pp. 203- 220 ,(1969) , 10.1016/0009-3084(69)90013-9
H. A. Walens, R. P. Koob, W. C. Ault, G. Maerker, Rearrangement of epoxy fatty esters to keto fatty esters Journal of the American Oil Chemists' Society. ,vol. 42, pp. 126- 129 ,(1965) , 10.1007/BF02545047
Howard W. Sperecher, H. J. Dutton, F. D. Gunstone, Ralph T. Holman, Metabolic conversions and the positional distributions in liver lecithin of some unnatural dienoic acids in the rat Lipids. ,vol. 2, pp. 122- 126 ,(1967) , 10.1007/BF02530910
F.D. Gunstone, I.A. Ismail, Fatty acids. Part 13. The synthesis of all the cis n-octadecenoic acids Chemistry and Physics of Lipids. ,vol. 1, pp. 209- 224 ,(1967) , 10.1016/0009-3084(67)90029-1