title: Chemical synthesis of glucuronidated metabolites of cortisol.
abstract: During in vivo metabolism the addition of six atoms of hydrogen to cortisone at the appropriate location and configuration can lead to formation of either 3 alpha,17,20 alpha,21-tetrahydroxy 5 beta-pregnan-11-one (cortolone) or 3 alpha,17,20 beta,21-tetrahydroxy-5 beta-pregnan-11-one (beta-cortolone). Likewise, metabolic reduction of cortisol can lead to formation of either 5 alpha-pregnane-3 alpha,11 beta,17,20 alpha,21-pentol (cortol) or the 20 beta isomer (beta-cortol). This paper describes the chemical syntheses of the C-3 beta-D-glucosiduronates of cortolone, beta-cortolone, cortol and beta-cortol-conjugates which are normal excretory products of man. The foregoing conjugates are characterized as free acids (or salts), as methyl esters and as polyacetate methyl esters.
mesh_terms: D005965:Glucuronates / Q000138:chemical synthesis*; D006854:Hydrocortisone / Q000031:analogs & derivatives* / Q000378:metabolism; D007202:Indicators and Reagents; D013329:Structure-Activity Relationship
chemical_list: D005965:Glucuronates; D007202:Indicators and Reagents; D006854:Hydrocortisone