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BILIRUBIN. 429
and which shows great similarity to tho urinary pigment, urobilin, as well
as to siercobilin found in the contents of the intestine (Masius and
Vanlaib j
). The reduction products have been carefully investigated
by H. Fischer and then by Paul Meter and F. Meyek-Betz. They
have found that hy< In (bilirubin is a mixture of bodies, among which there
is one which forms at least one-half and therefore, called henribilirvbin,
gives colorless crystals, and according to Fischer and Meyer-Betz
is identical with the urobilinogen of the urine. The formula of this
body is, C32H44N4O6 or C33H44N4OG. The other body is amorphous
but in properties and composition shows great similarity to the hemi-
bilirubin. The analyses correspond closely to the formula, C32H40X4O6.
This body as well as the hemibilirubin yields hsematinic acid and met Inl-
et hylmaleic imide on oxidation. As Kuster 2
first showed, bilirubin
yields hsematinic acid as oxidation product. It does not on the con-
trary yield methylethyl maleic imide.
Piloty and Thannhauser 3
obtained bilinic acid, C17H2GN2O3
from bilirubin on reduction with hydriodic acid and iodophosphonium.
Tliis acid corresponded to the hsematopyrrolidine carboxylic acid obtained
from haematoporphyrin. This bilinic acid is identical with the bilirubinic
acid described below and hence has this name.4
They also obtained an
isomeric acid to phonopyrrolic acid, the isophonopyrrol carboxylic acid
and in the potash fusion they found partly a dimethyl- and partly a
trimethylpyrrol. From bilinic acid they later obtained on mild oxida-
tion an intensely yellow colored acid, the dehydrobilinic acid.
From bilirubin and hemibilirubin, on heating with sodium methylate,
H. Fischer and Rose 5
have obtained 2, 4, 5- tri methylpyrrol-S-propionic
acid which was previously obtained by H. Fischer and Bartholomai s
from phonopyrrolcarboxylic acid. From bilirubinic acid on the con-
trary, with the same procedure they did not obtain this acid but another,
xanthobilirubinic acid, C17H22X2O3, which is probably identical with
dehydrobilinic acid, and which contains two atoms of hydrogen less than
bilirubinic acid, and which can be retransformed into the latter by glacial
acetic acid and hydriodic acid. As bilirubin, as well as hemibilirubin,
yields xanthobilirubinic acid as a side product with sodium methylate,
these experimenters consider this as a proof that the bilirubinic acid con-
1
Maly, Wien. Sitzungsber., 57, and Annal. d. Chem., 163; Masius and Vanlair,
Centralbl. f. d. med. Wissenseh., 1871, 369.
2
Hans Fischer, Zeitschr. f. physiol. Chem., 73, with Paul Meyer, ibid., 75, with.
Meyer-Betz, ibid., 75; Kuster, ibid., 26 and Ber. d. d. chem. Gesellsch, 32 and 35.
3
Piloty and Thannhauser, Annal. d. chem. u. Pharm., 390 and Ber d. d. chem.
Gesellsch., 45.
4
Piloty, Ber. d. d. chem. Gesellsch., 46, 1000; H. Fischer, ibid., 46, 1574.
s
Ber. d. d. chem. Gesellsch., 46, 439.
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