A proton magnetic resonance study of the 18-hydroxy derivatives of cortisol and corticosterone.
Proton magnetic resonance spectroscopy played a crucial role in the identification of a new corticosteroid, 18-hydroxycortisol, recently isolated from the urine of a patient with an aldosterone-producing adenoma. Mass spectrometric analysis and chemical degradative studies demonstrated an empirical formula of C21 H30 O6 corresponding to a diketopregnenetetrol and placed three of the four hydroxyl groups at the 11 beta, 18 and 21 positions. The first suggestion that the locus of the fourth hydroxyl was 17 alpha came from the n.m.r. spectrum in the form of negative evidence for proton linked to the carbon atom bearing this fourth hydroxyl. The n.m.r. spectral features of the 18-hydroxy derivatives of cortisol and corticosterone are compared. Both were found to exist in the 20, 18 cyclic hemiketal form.
D015069:18-Hydroxycorticosterone; D003345:Corticosterone / Q000031:analogs & derivatives; D006801:Humans; D006854:Hydrocortisone / Q000031:analogs & derivatives* / Q000652:urine; D009682:Magnetic Resonance Spectroscopy; D011522:Protons
D011522:Protons; D015069:18-Hydroxycorticosterone; C033689:18-hydroxycortisol; D003345:Corticosterone; D006854:Hydrocortisone