Untersuchungen über das Unverseifbare. I. Mitteilung. Über das Unverseifbare des Ovarialdermoidcystenfettes

Abstract

It is suggested that the living organism may synthesize cholesterol, which is structurally related to the bile acids and sex hormones, from squalene or fatty acids by way of intermediate products. A large ovarian dermoid cyst is opened and the contents mixed with several vols. ethyl alcohol. The mixture is filtered, the filtrate evaporated at 40[degree] in vacuo, and the residue extracted with ether in the Soxhlet apparatus. The ether extract is evaporated and 86.5 g. of oily liquid obtained, which is extracted with anhydrous ether. The ether soln. is saponified with Na alcoholate and 21.99 g. of unsaponifiable yellow oil obtained. The unsaponifiable substance is dissolved in 250 ml. 96% ale, 100 ml. of the soln. precipitated with digitonin and 0.92 g. cholesterol isolated. From the filtrate of the digitonin precipitation 7.71 g. of "residual unsaponifiable" material are recovered, which contain solid higher saturated aliphatic alcs., and squalene. The squalene is precipitated as the hexahydrochloride, m. 133.5[degree], by treating the ether or acetone soln. of the unsaponifiable material with HC1 gas at [long dash]5[degree], and 0.18 g. squalene obtained. The presence of squalene associated with cholesterol is characteristic of dermoid cyst fat. The saturated aliphatic alcohols found are tetradecyl, docosyl and carnaubyl alcohol. Aldehydes, ketones, iso- and hydroxycholesterol are not present, while dihydrocholesterol and ergosterol are present. Other substances found in dermoid cyst fat are formic, butyric, caproic, caprylic, myristic, palmitic, stearic, arachic and oleic acids, and cetyl, octadecyl, eicosyl alcohols and glycerin. The squalene in the dermoid cysts is to be regarded as a product of a pathologic abnormality in the fat metabolism.