重合油の構造と栄養価に関する研究 (第10報)
熱重合油の構造と毒性 (1)
1976 年 25 巻 2 号 p. 79-86
詳細
1976 年 25 巻 2 号 p. 79-86
It is known that polymerized oils heated in the inert gas showed toxicity to rats. The toxic components in those oils were presumed to be the monomeric cyclic fatty acids. But little knowledge has been obtained on the exact structure of them. A series of studies was performed to know more detailed structure and biological properties of these cyclic fatty acids.
Linseed oil heated in the nitrogen atomosphere was converted to methyl esters and subjected to distillation under reduced pressure. The distillate was treated with urea and fractionated into urea adduct and non-adduct-forming fractions. The latter was found to be toxic in a mouse bioassy. This fraction was converted to Bromo-Mercuri-Methoxy (BMM) adducts and chromatographed by silicic acid. After fractionation, the methoxy and bromo mercury groups were eliminated and recovered the original esters. The toxic study indicated that the fraction eluted with petroleum ether : dioxane (90 : 10) (Fr. III.) was found to be the most toxic to mice. In order to concentrate the toxic substances, BMM adducts were reformed from Fr. III and rechromatographed by successive elution with dioxane in petroleum ether in the ratio of 2 : 98 (Fr. III-A), 5 : 95 (Fr. III-B) and 10 : 90 (Fr.III-C). The results indicated that the Fr. III-B was the most toxic followed by the Fr. III-A and Fr. II-C. Subsequent analysis with the aid of GC-MS indicated that these toxic compounds had the skelton of methyl 7- (2'-n-propyl-cyclohexyl) nonancate and methyl 6- (2'-n- butylcyclohexyl) octanoate and containing two double bonds. In an attempt to determine the positions of the double bonds, the main components were collected by preparative GLC and were converted to TMS derivatives to be subjected to GC-MS analysis. The results revealed the presence of four positional isomers from (I) to (IV) in the most toxic fraction.
