Cholest-5-ene-3β,26-diol: Synthesis and biomedical use of a deuterated compound

To further studies of the metabolism of 26‐hydroxycholesterol in fetal and neonatal life, a deuterated compound was prepared from kryptogenin by Clemmensen reduction. The spectra of the deuterated 26‐hydroxycholesterol showed that five to nine deuterium atoms were incorporated per 26‐hydroxycholesterol molecule, with the maximum incorporation of eight deuterium atoms. The deuterated compound was recovered unchanged from the feces of a child following oral administration. Comparison of the ratio of deuterated to protium compound indicated the presence of an endogenous pool of 26‐hydroxycholesterol. Parenteral administration of the compound to a hamster indicated metabolism to deuterated chenodeoxycholic acid. The compound is useful as an isotope tracer for studies of the endogenous metabolism of 26‐hydroxycholesterol.