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Some physical, chemical, and biological properties of natural and synthetic unsaturated C 18 acids
Author(s) -
Gunstone F. D.
Publication year - 1973
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/bf02639866
Subject(s) - degree of unsaturation , cyclopropane , chemistry , organic chemistry , ricinoleic acid , melting point , gas chromatography , raman spectroscopy , spectral properties , stereochemistry , chromatography , computational chemistry , ring (chemistry) , castor oil , physics , optics
Series of octadecenoic ( cis and trans ), octadecynoic, octadecadienoic ( cis,cis and trans,trans ), and octadecadiynoic acids have been synthesized and employed in a comparative study of some physical (melting point, Raman spectra, NMR spectra, Ag + thin layer chromatography, and gas liquid chromatography) and biological properties. The results show that the position of unsaturation has a considerable influence on the physical and biological properties of isomeric unsaturated acids. Several chemical reactions of linoleic acid and of the related oxygenated acids ricinoleic or vernolic (12,13‐epoxyoleic) furnish cyclopropane compounds and 1,4‐ (or 1,5‐) epoxides. The formation of these is rationalized in terms of neighboring group participation. The oxymercuration‐demercuration reaction is the basis of a new method of examining acids with Δ3, Δ4, or Δ5 unsaturation.