Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
1253753 | Chemistry and Physics of Lipids | 2007 | 6 Pages |
Abstract
Allene oxide, (9Z,11E)-12,13-epoxy-9,11-octadecadienoic acid (12,13-EOD), was prepared by incubation of linoleic acid (13S)-hydroperoxide with flaxseed allene oxide synthase (AOS) and purified (as methyl ester) by low temperature HPLC. Identification of pure 12,13-EOD was substantiated by its UV and 1H NMR spectra and by GC-MS data for its methanol trapping product. The methyl ester of 12,13-EOD (but not the free carboxylic acid) is slowly cyclized in hexane solution, affording a novel cyclopentenone cis-12-oxo-10-phytoenoic acid. Free carboxylic form of 12,13-EOD does not cyclize due to the exceeding formation of macrolactone (9Z)-12-oxo-9-octadecen-11-olide. The spontaneous cyclization of pure natural allene oxide (12,13-EOD) into cis-cyclopentenone have been observed first time.
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Physical Sciences and Engineering
Chemistry
Chemistry (General)
Authors
Natalia V. Medvedeva, Lucia S. Mukhtarova, Faina K. Mukhitova, Alsu A. Balandina, Shamil K. Latypov, Alexander N. Grechkin,