114488-95-8Relevant articles and documents
Cyclization of natural allene oxide in aprotic solvent: formation of the novel oxylipin methyl cis-12-oxo-10-phytoenoate
Medvedeva, Natalia V.,Mukhtarova, Lucia S.,Mukhitova, Faina K.,Balandina, Alsu A.,Latypov, Shamil K.,Grechkin, Alexander N.
, p. 91 - 96 (2007)
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.
Geometrical configuration of 12,13-epoxyoctadeca-9,11-dienoic acid, a product of the reaction catalyzed by flaxseed allene oxide synthase (CYP74A)
Medvedeva,Latypov,Balandina,Mukhtarova,Grechkin
, p. 595 - 596 (2005)
The geometrical configuration of a short-living allene oxide reaction product that arises under the catalysis by flaxseed allene oxide synthase (CYP74A) was studied by NMR spectroscopy. The structure of (9Z,11E)-12,13- epoxyoctadeca-9,11-dienoic acid was established for it from the results of the nuclear Overhauser effect measurements.
