The preparation and characterization of the methoxy derivatives of polyunsaturated fatty acids: Stabilized product analogs of lipoxygenase catalysis

Abstract

AbstractThe products from the action of soybean lipoxygenase on a series of polyunsaturated fatty acids have been converted in 2 steps into the corresponding methoxy derivatives. The product hydroperoxides were reduced in situ to alcohols with sodium borohydride. The ethers were generated by treatment of the alcohols with sodium hydride and methyl iodide in tetrahydrofuran. 13‐Methoxy‐9(Z),11(E)‐octadecadienoic, 15‐methoxy‐11(Z),13(E)‐eicosadienoic and 15‐methoxy‐5(Z),8(Z),11(Z), 13(E)‐eicosatetraenoic acids were thus prepared. The methyl ethers were analyzed and the structures established by high performance liquid chromatography, nuclear magnetic resonance and infrared spectrometry, polarimetry and mass spectroscopy (as methyl esters). The methylation reaction proceeds without molecular rearrangements or racemiziation.