SECTIONAL TRANSACTIONS.—B, 467 
Ascheim and Zondek in 1927 discovered the hormone in pregnancy urine. 
The chemical nature of the active substance was partially disclosed by 
methods of obtaining potent extracts. Its phenolic nature was recognised 
by Funk and by Marrian in 1929. 
Doisy, Veler and Thayer, in 1929, and shortly afterwards Butenandt, and 
also Dingemanse, isolated crystalline ketohydroxycestrin, C,H», (CO)(OH). 
Marrian obtained trihydroxyestrin, C}sH2;(OH)s, in 1930. 
Butenandt, having found both compounds in pregnancy urine, de- 
monstrated that ketohydroxyeestrin was formed by potassium bisulphate 
dehydration of trihydroxyeestrin, a reaction which Marrian and Haslewood 
later showed to occur through elimination of the elements of water between 
the two alcoholic hydroxyl groups of trihydroxyeestrin. 
Examination of surface films of cestrin derivatives by Adam and Danielli 
and a crystallographic investigation by Bernal showed the estrin molecule to 
possess a rigid fused-ring structure of the phenanthrene or anthracene type, 
with the phenolic group remote from the other oxygen-containing groups. 
The absence of ethylenic double bonds was shown by the preparation of 
substituted mono-bromo-derivatives. 
Dr. A. BUTENANDT.—The relation of the sex hormones to the sterols 
and bile acids, 
The following constitutional formule have been proposed for the follicular 
hormone, C,,;H 2302) and its hydrate, Ci3H.,0; : 
O OH 
CH; | CH; | 
(SP i nS 
iparifions ¢ 
HO\V/\Y (D HOVY/\/ (ID 
These formulz are based on the following observations : 
(x) The follicular hormone is a hydroxyketone, the hydrate a trihydroxy- 
compound ; both contain one acidic hydroxyl group, similarly linked in each 
case, whilst in the hydrate two adjacent secondary alcoholic groups replace 
the keto-group. 
_ (2) The results of catalytic hydrogenation conjoined with those of the 
measurement of molecular refraction show decisively the presence in the 
molecule of only three double bonds. This being established, the hydrogen 
content as determined by analysis demands a four-ring system. 
(3) The three double-bonds confer aromatic character, as shown by their 
chemical behaviour and in view of the results of measurements of molecular 
refraction and ultraviolet absorption. The acidity of the phenolic group 
is to be explained by its phenolic character. 
(4) The keto-group or the two hydroxyl groups are in a terminal five- 
membered ring, which is opened by the alkali-fusion of the hydrate, a 
dicarboxylic acid C,;H.,O; being formed. 
(5) The points of union of this ring are shown by the degradation of 
the acid C,,H,,O; to 1 : 2-dimethyl-7-hydroxyphenanthrene and 1 : 2-di- 
methylphenanthrene. 
The formule I and II demonstrate a clear connection between the folli- 
cular hormone and the sterols, bile-acids, and pregnandiol. This relation- 
ship is substantiated by the preparation of degradation products common 
