Professional Documents
Culture Documents
REACTIONS
BY H. W. MARLOW
(From the Department of Biochemistry, Southwestern Medical College of the
University of Texas, Dallas)
(Received for publication, July l&1949)
EXPERIMENTAL
TABLE I
Stru,clural ConJiguration of Steroids and Zimmermann and Kober Reagwh
-
Compound Position Group at immermann Kober reaction*
occupied position reaction’
Kober Reaction
The above modified Kober reaction was employed with p-naphthol in
concentrated HzS04. Table I shows the peak values at 508 rnp as in the
Zimmermann reaction. Here again, when the carbonyl group is at posi-
tion 17 and the methylene carbon is at position 16, the greatest amount of
color is produced. However, 3-methoxy-lG-keto-a-estradiol is an excep-
tion to this. When carbonyl groups are at positions 16 and 17 and a
methylene carbon is at position 15 (conditions under which the Zimmer-
Results
From a study of the groups affecting the intensity of color development
in the Zimmermann and Kober reactions, the following results are re-
ported.
Zimmermann Reuction-(1) Maximum color is developed when the com-
pound contains a carbonyl group at position 17 and a methylene carbon ad-
jacent at position 16 in the perhydro-1, 2-cyclopentanophenanthrene com-
pounds. (2) When a carbonyl group is at position 16 and the two adjacent
carbons are methylenic, or when there are carbonyl groups at both po-
sitions 16 and 17 and amethylenic carbon at position 15, no color is produced.
(3) When an OH or R group is at position 17 with an adjacent methylenic
carbon at position 16, no color development is observed. (4) If position
3 has a methoxy or benzyloxy group on it, there is a significant effect on
the transmission of light. (5) Unsaturation of Ring A or Rings A and
B does not significantly affect the color development.
Modified Kober Reaction-(l) Maximum color is developed when the
compound contains a carbonyl group at position 17 and a methylenic
carbon at the 16th position of all the estrogens tested. (2) If an OH
group is at position 17, or at both positions 1G and 17, together with
adjacent methylenic carbons, the K value is roughly 50 per cent of that
of compounds with a carbonyl group at the 17t.h position. (3) Meth-
oxyestrone gives more color but the benzyloxy derivative gives less color
than estrone in the Kober test. (4) Carbonyl groups at position 16 or at
both the 16th and 17th positions gave no color and hence showed no peak
value. (5) A hydroxyl group at position 17 and a carbonyl group at po-
sition 16 show as much transmission activity as a carbonyl at position
17 with an adjacent methylenic carbon.
H. W. MARLOW 171
SUMMARY
BIBLIOGRAPHY