Carbon-13 NMR spectra of some representative hormonal steroids

Abstract

Assignments are proposed for the 13C NMR spectra of the following hormonal steroids on the basis of comparisons with the published spectra of some closely related steroids and single-frequency off-resonance-decoupled (SFORD) measurements: 11β,17α,21-trihydroxy-4-pregnene-3,20-dione,21-acetate (hydrocortisone acetate, 7); 17α,21-dihydroxy-4-pregnene-3,11,20-trione,21-acetate (cortisone acetate, 6); 17α,21-dihydroxy-1,4-pregnadiene-3,11,20-trione,21-acetate(prednisone acetate, 3); 11β,17α,21-trihydroxy-1,4-pregnadiene-3,20-dione,21-acetate(prednisolone acetate, 2); 17β-hydroxy-1,4-androstadiene-3-one (DTS, 10); 9α-fluoro-11β,17α,21-trihydroxy-16α-methyl-1,4-pregnadiene-3,20-dione,21-acetate (dexamethasone acetate, 13); 9α-fluoro-11β,17α,21-trihydroxy-16β-methyl-1,4-pregnadiene-3,20-dione,21-acetate (betamethasone, 14): 6α-fluoro-11β,17α,21-trihydroxy-16α-methyl-1-4-pregnadiene-3,20-dione,21-acetate (paramethasone acetate, 15), 11β,17α,21-trihydroxy-6α-methyl-1,4-pregnadiene-3,20-dione (6α-methyl-prednisolone, 16); 17β-hydroxy-3-oxo-4,6-androstadiene-17α-propionic acid, γ-lactone (canrenone, 18); 3β-hydroxy-6α-carbonitrile-5-pregnene-20-one (PCN, 21).