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Formation of γ‐ketols from 13‐ and 9‐hydroperoxides of linolenic acid by flaxseed hydroperoxide isomerase
Author(s) -
Feng Paul,
Vick Brady A.,
Zimmerman Don C.
Publication year - 1981
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/bf02534967
Subject(s) - chemistry , clinical chemistry , lipidology , isomerase , linolenic acid , organic chemistry , fatty acid , biochemistry , stereochemistry , enzyme , linoleic acid
A reexamination of the flaxseed hydroperoxide isomerase reaction showed that a minor enzymic product (ca. 5%), identified as a γ‐ketol, was present. The substrates were the 13‐ or 9‐hydroperoxides of linolenic acid, which were converted to 9‐hydroxy‐12‐oxo‐ cis ‐15‐ trans ‐11‐octadecadienoic acid, respectively. These compounds were formed in addition to the major products reported earlier: a 12,13‐α‐ketol and 12‐oxo‐ cis ‐10,15‐phytodienoic acid from the 13‐isomer, and a 9,10‐α‐ketol from the 9‐isomer.