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A new sterol has been isolated from the skin of rats treated with triparanol. The structure proposed for this compound is Δ7, 24-cholestadien-3β-ol, on the basis of the following evidence. 1. The optical rotation is similar to that of Δ7-cholesten-3β-ol. 2. Hydrogenation with Raney nickel catalyst yields a compound with chromatographic behavior similar to that of Δ7-cholesten-3β-ol. 3. Hydrogenation with palladium catalyst yields a compound with an infrared spectrum indistinguishable from that of δ8(14)-cholesten-3β-ol. Approximately 1 mole of hydrogen is absorbed per mole of sterol. 4. The elemental composition is correct for the proposed structure. 5. The infrared spectrum is similar to that of Δ7-cholesten-3β-ol, except for the differences to be expected from the presence of the Δ24 bond. 6. The nuclear magnetic resonance spectrum differs from that of Δ7-cholesten-3β-ol in the ways predicted. Δ7, 24-Cholestadien-3β-ol is biologically convertible to Δ7-cholesten-3β-ol and to cholesterol. It can be derived from Δ8, 24-cholestadien-3β-ol, but the reverse reaction could not be shown.
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Frantz et al. (1966) studied this question.
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