Synthesis of multi-labeled cortisols and cortisones with (2)H and (13)C for study of cortisol metabolism in humans

Steroids. 2000 Apr;65(4):180-9. doi: 10.1016/s0039-128x(99)00102-6.

Abstract

A method is described for the preparation of multi-labeled cortisol and cortisone with (13)C and (2)H via the indan synthon method, starting from chiral 11-oxoindanylpropionic acid. [1, 3-(13)C(2)]Acetone was used for the syntheses of [1,2,4, 19-(13)C(4)]cortisol (cortisol-(13)C(4)) and [1,2,4, 19-(13)C(4)]cortisone (cortisone-(13)C(4)), and [1,3-(13)C(2),1,1,1, 3,3,3-(2)H(6)]acetone was for [1,2,4,19-(13)C(4),1,1,19,19, 19-(2)H(5)]cortisol (cortisol-(13)C(4),(2)H(5)) and [1,2,4, 19-(13)C(4),1,1,19,19,19-(2)H(5)]cortisone (cortisone-(13)C(4), (2)H(5)). The chemical shifts for the (13)C and (1)H NMR spectra of cortisol and cortisone were fully assigned.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbon Isotopes
  • Cortisone / chemical synthesis*
  • Deuterium
  • Gas Chromatography-Mass Spectrometry / standards
  • Hydrocortisone / chemical synthesis*
  • Hydrocortisone / metabolism
  • Isotope Labeling / methods*
  • Magnetic Resonance Spectroscopy

Substances

  • Carbon Isotopes
  • Deuterium
  • Cortisone
  • Hydrocortisone