linoleic-acid-hydroperoxide and cyclopentenone

linoleic-acid-hydroperoxide has been researched along with cyclopentenone* in 2 studies

Other Studies

2 other study(ies) available for linoleic-acid-hydroperoxide and cyclopentenone

Article	Year
Distinct Mechanistic Behaviour of Tomato CYP74C3 and Maize CYP74A19 Allene Oxide Synthases: Insights from Trapping Experiments and Allene Oxide Isolation. International journal of molecular sciences, 2023, Jan-23, Volume: 24, Issue:3 The product specificity and mechanistic peculiarities of two allene oxide synthases, tomato LeAOS3 (CYP74C3) and maize ZmAOS (CYP74A19), were studied. Enzymes were vortexed with linoleic acid 9-hydroperoxide in a hexane-water biphasic system (20-60 s, 0 °C). Synthesized allene oxide (9,10-epoxy-10,12-octadecadienoic acid; 9,10-EOD) was trapped with ethanol. Incubations with ZmAOS produced predominantly 9,10-EOD, which was converted into an ethanolysis product, (12 Topics: Hexanes; Oxides; Solanum lycopersicum; Zea mays	2023
Cyclization of natural allene oxide in aprotic solvent: formation of the novel oxylipin methyl cis-12-oxo-10-phytoenoate. Chemistry and physics of lipids, 2007, Volume: 148, Issue:2 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 (1)H 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. Topics: Chromatography, High Pressure Liquid; Cyclization; Cyclopentanes; Flax; Hydrophobic and Hydrophilic Interactions; Intramolecular Oxidoreductases; Lactones; Linoleic Acids; Lipid Peroxides; Macrolides; Models, Chemical; Solvents; Spectrum Analysis; Stereoisomerism; Temperature	2007

Article

Year

Distinct Mechanistic Behaviour of Tomato CYP74C3 and Maize CYP74A19 Allene Oxide Synthases: Insights from Trapping Experiments and Allene Oxide Isolation.

International journal of molecular sciences, 2023, Jan-23, Volume: 24, Issue:3

The product specificity and mechanistic peculiarities of two allene oxide synthases, tomato LeAOS3 (CYP74C3) and maize ZmAOS (CYP74A19), were studied. Enzymes were vortexed with linoleic acid 9-hydroperoxide in a hexane-water biphasic system (20-60 s, 0 °C). Synthesized allene oxide (9,10-epoxy-10,12-octadecadienoic acid; 9,10-EOD) was trapped with ethanol. Incubations with ZmAOS produced predominantly 9,10-EOD, which was converted into an ethanolysis product, (12

Topics: Hexanes; Oxides; Solanum lycopersicum; Zea mays

2023

Cyclization of natural allene oxide in aprotic solvent: formation of the novel oxylipin methyl cis-12-oxo-10-phytoenoate.

Chemistry and physics of lipids, 2007, Volume: 148, Issue:2

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 (1)H 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.

Topics: Chromatography, High Pressure Liquid; Cyclization; Cyclopentanes; Flax; Hydrophobic and Hydrophilic Interactions; Intramolecular Oxidoreductases; Lactones; Linoleic Acids; Lipid Peroxides; Macrolides; Models, Chemical; Solvents; Spectrum Analysis; Stereoisomerism; Temperature

2007