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Identification of novel octadecadienoic fatty acids in the seaweed Cladophora rupestris through oxidative ozonolysis of the alcohols prepared from the acids
Author(s) -
Ratnayake W. N.,
Ackman R. G.
Publication year - 1979
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/bf02533536
Subject(s) - degree of unsaturation , ozonolysis , chemistry , organic chemistry , fatty alcohol , alcohol , reagent , fatty acid , polyunsaturated fatty acid , alkyl , algae , chromatography , botany , biology
The BF 3 −MeOH reagent for ozonolysis of ethylenic unsaturation does not oxidize alcohols. It is therefore feasible to determine the position of ethylenic unsaturation in long chain fatty alcohols of synthetic or natural origin by recovering the methyl ester products intact and silylating the alcohol function of half‐ester, half‐alcohol, products prior to gas liquid chromatographic analysis. The C 3 fragment from methylene‐interrupted alkyl chains is not recovered, but, by first reducing carboxyl ester groups to alcohols, the terminal difunctional products can be identified in nonmethylene‐interrupted dienoic fatty acids. The seaweed Cladophora rupestris is shown to contain Δ5,Δ11‐,Δ8,Δ11‐, and Δ11, Δ14‐ as well as Δ9,Δ12‐octadecadienoic acid.