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Wool wax. VIII. —The composition of the unsaponifiable material
Author(s) -
Horn D. H. S.
Publication year - 1958
Publication title -
journal of the science of food and agriculture
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.782
H-Index - 142
eISSN - 1097-0010
pISSN - 0022-5142
DOI - 10.1002/jsfa.2740091002
Subject(s) - unsaponifiable , autoxidation , chemistry , wax , organic chemistry , activated alumina , squalene , chromatography , catalysis
The optimum conditions for the chromatographic fractionation of the unsaponifiable material on activated alumina have been worked out and applied, together with the urea separation of the aliphatic alcohols, to the separation of the unsaponifiable materials of freshly secreted and autoxidized waxes. The unsaponifiable material of the relatively fresh wax was found to be made up of the following major components: iso cholesterol (the lanosterol—dihydrolanosterol mixture), 44.2%; cholesterol, 32.5%; urea‐separated aliphatic alcohols, 14.7%; aliphatic diols, 3.2%, and hydrocarbons, 0.9%. The unsaponifiable materials from autoxidized waxes contained in addition an unresolved resinous complex mixture which was shown to be composed of autoxidation products, derived chiefly from the unsaturated unsaponifiable constituents, viz., iso cholesterol and cholesterol, and it is concluded that these reactive substances, in the form of wool wax esters, undergo primary attack at the active methylene groups adjacent to the unsaturated bonds to yield α‐unsaturated ketone and alcohol derivatives, probably via unstable hydroperoxide precursors, as has been shown to be the case in the autoxidation of dihydrolanosteryl acetate, a model wool wax compound. Secondary reactions probably involve the unsaturated bonds of these primary products and lead to saturated ketones and saponifiable substances.