Submitted to: Journal of the American Oil Chemists' Society
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: March 28, 1995
Publication Date: N/A
Interpretive Summary: Novel fatty acid derivatives (hydroxy fatty acids) were synthesized from commercial fatty acids and characterized. These compounds have potential in commercial applications such as additives in lubricants, greases, vegetable-oil based diesel fuels, and cosmetics.
Technical Abstract: Several novel allylic mono- and dihydroxy fatty compounds were synthesized from delta 5-, delta 7-, delta 8-, and delta 10- monounsaturated fatty acids with the selenium dioxide / tert.- butylhydroperoxide system. Chain lengths were C19 for delta 7 and delta 10 and C20 for delta 5 and delta 8. With the full range of delta 5- to delta 11-unsaturated allylic monohydroxy fatty compounds available, position-dependent effects in the 13C-NMR spectra of these compounds are discussed. The olefinic carbon shift differences in monohydroxy compounds where the OH group is located between the double bond and the terminal methyl group were plotted as a function of double bond distance from C1. This plot is presumably an exponential function. During SeO(2)-based hydroxylation, lactonization of the hydroxy groups located between the double bond and the carboxyl group also occurs for delta 5 unsaturation.