ALLYLIC HYDROXY FATTY COMPOUNDS WITH DELTA-5-UNSATURATION, DELTA-7-UNSATURATION, DELTA-8-UNSATURATION, AND DELTA-10-UNSATURATION

Several novel allylic mono- and dihydroxy fatty compounds were synthes ized from Delta 5, Delta 7-, Delta 8-, and Delta 10-monounsaturated fa tty acids with the selenium dioxide/tert-butylhydroperoxide. Chainleng ths were C-19 for Delta 7 and Delta 10, and C-20 for Delta 5 and Delta 8 compounds. With a full range of Delta 5- to Delta 11-unsaturated al lylic monohydroxy fatty compounds available, position-dependent effect s in the C-13-nuclear magnetic resonance spectra of these compounds ar e discussed. The olefinic carbon shift differences in monohydroxy comp ounds, where the OH group is located between the double bond and the t erminal methyl group, were plotted as a function of double-bond distan ce from C-1. This plot is presumably a rational function. During SeO2- based hydroxylation, lactonization of the hydroxy groups, located betw een the double-bond and the carboxyl group, also occurs for Delta 5 un saturation.