オレイン酸メチルおよびC18-トランス・トランス共役ジエン酸メチルと無水マレイン酸との反応生成物について

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Authors studied the isolation technique and some properties (NMR, UV, IR, GLC, TLC, and saponification rate) of the trimethyl esters of mono-maleic anhydride adducts of oleic acid and trans-trans conjugated octadecadienoic fatty acid. The silicic acid column chromatography or thin-layer chromatography technique using silica coated plate and solvent system consisting of petroleum ether-diethyl ether=7 ; 35 : 5 (vol/vol) resulted in good effects on the isolation of mono-maleic anhydride adducts. In the case of oleic acid adduct, it was found that a-methylene group adjacent to double bond disappared (by NMR) and cis-double bond was converted to traps form (by IR and NMR), then it was conjectured that the succinic acid type adduct was formed. In the case of trans-trans conjugated octadecadienoic fatty acid adduct, cyclohexene type adduct was formed which differed from oleic acid adduct. The separation of cyclohexene type adduct and succinic acid type adduct each other from their mixture was found to be possible by the programmed gas liquid chromatography technique using 3 % SE-30/chromosorb W column and hydrogen flame ionization detector. The peak temperature of the former was 203°C, and the latter was 194 °C. In addition, surface active properties of their tripotassium salts were discussed.