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Allylic hydroxy fatty compounds with Δ5‐, Δ7‐, Δ8‐, and Δ10‐Unsaturation
Author(s) -
Knothe G.,
Bagby M. O.,
Weisleder D.,
Peterson R. E.
Publication year - 1995
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/bf02635659
Subject(s) - degree of unsaturation , double bond , allylic rearrangement , chemistry , hydroxylation , fatty acid , stereochemistry , medicinal chemistry , organic chemistry , catalysis , enzyme
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 C 19 for Δ7 and Δ10, and C 20 for Δ5 and Δ8 compounds. With a full range of Δ5‐ to Δ11‐unsaturated allylic monohydroxy fatty compounds available, position‐dependent effects in the 13 C‐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 C 1 . This plot is presumably a rational function. During SeO 2 ‐based hydroxylation, lactonization of the hydroxy groups, located between the double‐bond and the carboxyl group, also occurs for Δ5 unsaturation.