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The Products of Pyrolysis of Cholesterol at 360°C. and Their Relation to Carcinogens^*

(From the Department of Pathology, University of Chicago, Chicago 37, Illinois)

The products formed by pyrolysis of cholesterol at 360°C. were separated and the following compounds were identified; cholestenone, dicholesteryl ether, 3,5-cholestadiene, the naphthalene derivative of cholesterol, the phenanthrene derivative of cholesterol, methylcyclopentenophenanthrene, and chrysene.

Except for cholestenone all of these products are intermediates in the transformation of cholesterol to methylcholanthrene. The latter compound was not found because instead of cyclization of the sidechain a break occurred at the C₁₇ position. The dehydration and dehydrogenation of the ring system occurred but the last step, cyclization of the sidechain, did not.

Six compounds whose degree of carcinogenic activity is unknown or uncertain were obtained. These include the saturated hydrocarbons cholestane and coprostane, the naphthalene derivative of cholesterol, the phenanthrene derivative of cholesterol, methylcyclopentenophenanthrene, the chrysene derivative, and the ketonic products. Tests for carcinogenicity of these products are under way.

^* This investigation was assisted by a research grant from the American Cancer Society recommended by the Committee on Growth of the National Research Council.