Springer Online Journal Archives 1860-2000
Chemistry and Pharmacology
Conclusions 1. The pK′ a values of 10 phenolic steroids were determined. It is shown that the introduction of a Δ8(9)-double bond conjugated with the aromatic A ring increases the degree of ionization of the phenolic hydroxyl group. 2. It is shown that transition for 17- and 17α-keto-3-hydroxy-Δ1,3,5(10)-estratrienes to the corresponding 3,17β- and 3,17αβ-dihydroxy compounds as well as from the normal series to the D homoanalogs is accompanied by a decrease in acidity, which may be the result of the distance effect from the D ring to the A ring. 3. A linear correlation is observed between the chemical oxidation constants (k2) and the dissociation constants (K) of 3,17-dihydroxy-Δ1,3,5(10)-estratrienes, which makes it possible to assume the existence of an interaction between C3 and C17 (C17α) by means of distance effects from the A ring to the D ring and from the D ring to the A ring.
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