220 Messrs. Dorée and Gardner. Origin and  [Dee. 20, 
Hippocoprosterol behaves, therefore, as a saturated alcohol. The hydroxyl - 
group, however, is not readily replaceable by chlorine. When ground up 
with phosphorus pentachloride in the cold, no action takes place, though 
on adding petrol and boiling some hydrochloric acid is evolved, but we 
have not succeeded in preparing the chloride, either by this method or by 
the use of thionyl chloride. Various substances appear to be formed, which 
we are at present investigating. 
Hxamination of the Alcoholic Mother Liquors. 
The residues remaining after separation of the hippocoprosterol were 
subjected to a careful examination, first with the object of isolating the 
a-hippocoprosterol (m.p. 66° to 67°) described by Wilenko, and secondly to 
discover whether any of the cholesterol of the bile was present. 
As an example, 2 kilogrammes of dry dung obtained in the summer yielded 
3°65 grammes or 0°18 per cent. of hippocoprosterol, and 8:1 or 0-4 per cent. 
of a dark red buttery residue. The latter was dissolved in alcohol and 
allowed to evaporate. The first crops of material obtained gave melting 
points varying between 65° and 70°, but small quantities of pure hippocopros- 
terol could always be obtained from these. The second crop (0°2 gramme) 
gave a body which dissolved easily in all solvents, except dilute alcohol, from 
which it crystallised readily in microscopic hexagonal plates. It melted at 
136° to 137°, absorbed bromine in carbon bisulphide solution, and gave the 
‘Salkowski and Liebermann colour tests. It thus agreed closely with the 
‘sitosterol of Burian.* The acetate of the body, however, did not confirm 
this. It was made in the usual way with acetic anhydride and sodium 
acetate, and came out of dilute alcohol in brilliant glistening leaves consisting 
of six-sided plates. In all its properties, however, it agreed with the original 
substance, except that it was less soluble in absolute alcohol. It gave a 
constant melting point of 136°, which could not be altered by repeated 
crystallisation. Sitosterol acetate melts at 127°5. The third crop 
(0'1 gramme) was white, and after several crystallisations from 80-per-cent. 
alcohol appeared under the microscope as long thin plates like sword blades. 
These melted sharply at 161° to 162° and gave Liebermann’s colour test. To 
identify it if possible with the caulosterine obtained by Schulze and Barbierit 
from the shoots of the yellow lupin (m.p. 158°), it was heated with benzoic 
anhydride, but no crystalline benzoate could be obtained. The concentrated 
alcoholic filtrate still showed traces of solid matter, but this could not be 
* From germinating wheat, ‘ Monatshefte f. Chemie,’ 1897, vol. 18, p. 551. 
+ ‘Journ. Prak. Chem.’ (2), vol. 25, p. 159. 
