Cholest-5-ene-3 beta, 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.
D000818:Animals; D001646:Bile / Q000378:metabolism*; D002635:Chenodeoxycholic Acid / Q000378:metabolism*; D002648:Child; D006224:Cricetinae; D003903:Deuterium; D005243:Feces / Q000032:analysis; D006801:Humans; D006888:Hydroxycholesterols / Q000032:analysis / Q000138:chemical synthesis / Q000378:metabolism*; D007263:Infusions, Parenteral; D007553:Isotope Labeling; D013058:Mass Spectrometry
D006888:Hydroxycholesterols; D002635:Chenodeoxycholic Acid; C007042:cholest-5-ene-3 beta,26-diol; D003903:Deuterium