Allylic hydroxy fatty compounds with Δ5‐, Δ7‐, Δ8‐, and Δ10‐Unsaturation

Abstract Several novel allylic mono‐ and dihydroxy fatty compounds were synthesized from Δ5, Δ7‐, Δ8‐, and Δ10‐monounsaturated fatty acids with the selenium dioxide/tert‐butyl‐hydroperoxide. Chainlengths were C19 for Δ7 and Δ10, and C20 for Δ5 and Δ8 compounds. With a full range of Δ5‐ to Δ11‐unsaturated allylic monohydroxy fatty compounds available, position‐dependent effects in the13C‐nuclear magnetic resonance 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 a rational function. During SeO2‐based hydroxylation, lactonization of the hydroxy groups, located between the double‐bond and the carboxyl group, also occurs for Δ5 unsaturation.