New Geometric Isomers of Oxooctadecadienoate in Copper-catalyzed Decomposition Products of Linoleate Hydroperoxide

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概要

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• Methyl linoleate hydroperoxide produced by autoxidation was refluxed with 10^-4M Cu-naphthenate in benzene. Two new geometrical isomers of oxooctadecadienoate (compounds I and II) were found in addition to the four known isomers. They were isolated by a Sephadex LH-20 column chromatography with chloroform-hexane (2 : 1) and purified by HPLC on Nucleosil ^[○!R]100-5 and Zorbax ODS columns. UV, IR, MS, and ^1H-NMR spectra were measured. The geometry of conjugated dienes were assigned from the coupling constants of the olefinic protons. Compounds I and II were identified as 13-oxo-trans-9,cis-11-and 9-oxo-cis-10,trans-12-octadecadienoate, respectively. Each of them had a cis double bond adjacent to the oxo group. The hydroperoxides of the same geometry as compounds I and II were also detected in autoxidation products.

• 社団法人日本農芸化学会の論文
• 1999-06-23

著者

• Morita Makio

  Department Of Food And Nutrition Japan Women's University

• Tokita M

  Japan Women's Univ. Tokyo Jpn

• TOKITA Masako

  Department of Food and Nutrition, Japan Women's University

• IWAHARA Jyunko

  Department of Food and Nutrition, Japan Women's University

• Tokita Masako

  Department Of Food And Nutrition Japan Women's University

• Iwahara Jyunko

  Department Of Food And Nutrition Japan Women's University

• Morita Makio

  Department of Agricultural Chemistry, Faculty of Agriculture, The University of Tokyo

関連論文

• Autocatalytic Activity in the Low-Polarity Part of Autoxidizing Methl Linolenate(ノ-ト)
• New Geometric Isomers of Oxooctadecadienoate in Copper-catalyzed Decomposition Products of Linoleate Hydroperoxide
• Identification of New Geometric Isomers of Methyl Linoleate Hydroperoxide and Their Chromatographic Behavior
• Methyl 9-(2-(2,5-Dihydro-5-pentylfuryl))-nonanoate in the Copper-catalyzed Decomposition Products of Methyl Linoleate Hydroperoxides and Some Other Products(Food & Nutrition)
• Influence of Linoleate Hydroperoxide Minor Isomers on GLC Analysis of Oleate Hydroperoxides
• Different Rates of Geometric Isomers of Linoleate Hydroperoxide in Acid-catalyzed Decomposition
• Methyl Linoleate Dimer and Methyl 8-Phenyloctanoate in the Coppercatalyzed Decomposition Products of Methyl Linoleate Hydroperoxides
• Non-metal-requiring Catalyst Contained in Recovered Methyl Linolenate from an Autoxidizing Sample

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