The original purpose of this work was to
determine the constitution of an organic half -ester
of sulphuric acid isolated from mare's pregnancy
urine by Schachter and Marrian in Toronto in 1938.
Two new organic sulphates, one of which
may be identical with that of Schachter, have been
isolated and studied. The scope of the work has
been widened, so that it now represents some initial
stages in a general study of the conjugates of horse
urine. Some incidental work on the pure chemistry
of organic sulphates has also been done.
PART 1 of this Thesis outlines the previous
work on the organic sulphates of mare's pregnancy
urine (Schachter and Marrian, 1936, 1938; Schachter,
Ph.D. Thesis, 1939; Butenandt and I-Iofstetter, 1939) .
PART 2 describes the sources and collection
of urine, the extraction of the sulphates and the
early stages in their purification. These methods
have been developed from those of Schachter.
PART 3 describes the isolation and study of a
sulphate (2 sulphate) which may be identical with
that of Schachter and Marrian. This sulphate on acid
hydrolysis yields a compound of the probable formula
C₂₁H₃₂O₂ (Compound Z) which is apparently not identical
with any substance previously obtained from mare's
pregnancy urine. Z appears to be a 3-ß-hydroxy
steroid and may contain an αß-unsaturated ketonic
group. Comparison of Z and Δ¹⁶ allopregnene-3 (ß)-ol-20-one
indicates that these substances are probably
identical, although the evidence is insufficient for
PART 4 describes the isolation and study of
another sulphate (Y sulphate). This on acid
hydrolysis yields Compound Y, probable formula
C₂₁H₃₂O₂. Y is a saturated dihydroxy compound,
probably a 3(ß)-hydroxy steroid. The properties of
Y and its derivatives closely resemble those of
' uranediol' and its derivatives (Marker et al., 1938f),
but no direct comparison has yet been possible.
PART 5 of this Thesis describes miscellaneous
experiments on mare's urine, conjugates, incidental
to the study of Z and Y, which may be useful if a
thorough study of horse-urine steroids is undertaken.
The great drawback throughout the work has
been lack of material. Probably more time has been
spent in looking for urine than in working it up. So
far as the primary purpose of the work is concerned,
lack of material has prevented a complete study of
Compounds Z and Y. In the wider field, few definite
results have been obtained; it has rarely been
possible to study a number of batches of urine in the
same way, and so to obtain results of quantitative
significance. Again,while many different methods
of extraction and separation have been tried at
different times (Part 2, section 6), controls have
rarely been carried out, and this part of the work
must be considered a very sporadic reconnaisance
The author begs anyone who reads this thesis to bear
these facts constantly in mind.