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The preparation and characterization of the methoxy derivatives of polyunsaturated fatty acids: Stabilized product analogs of lipoxygenase catalysis
Author(s) -
Funk Max O.,
Levison Bruce,
Keller Maggie B.
Publication year - 1980
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1007/bf02534322
Subject(s) - chemistry , sodium borohydride , lipoxygenase , methyl iodide , catalysis , polyunsaturated fatty acid , organic chemistry , sodium iodide , mass spectrometry , fatty acid , chromatography , enzyme
The 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.