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CONSTITUTION OF THE BLOOD-PIGMENTS. 297
acid imide, which also haemato- and mesoporphyrin give, were obtained by
Marchlewski on the oxidation of phylloporphvrin and by Willstatter,
XX)—C.C2 H5
besides methylclhylmaleic imide, HX<^ , on the oxidation of
xCO—C.CH3
certain chlorophyll derivatives. The sarne two products were obtained
1 \ Ivuster l
on the oxidation of mesoporphyrin while haemin and haema-
toporphyrin gave no methylethylmaleic imide.
It has bem known for a long time that haemin and hacmatoporphyrin
gave an abundance of pyrrol on heating, and that phylloporphyrin has a
similar behavior was first shown by Schunck and Marchlewski.
That at least one pyrrol, of the pyrrol mixture, the so-called hcemopyrrol
is common to both the blood and leaf pigments has been shown by the
investigations of Marchlewski and his collaborators, and from haemo-
pyrrol Kuster was the first to obtain methylethylmaleic imide on oxida-
tion, showing that haemopyrrol was probably a dimethylethylpyrrol.
This behavior has been further developed by the investigations of
Piloty and Willstatter on the reduction products of the blood and
leaf pigments and by H. Fischer and Bartholomaus 2
on the sub-
stituted pyrrols.
Willstatter obtained a pyrrol mixture from hsemin and haemato-
porphyrin, as well as from chlorophyll derivatives, by reduction, from
which he isolated three different pyrrols. The first, which he calls hcemo-
pyrrol, was perhaps not perfectly pure, consisted at least in great part
of the cryptopyrrol (Fischer and Bartholomaus, c-haemopyrrol of
Piloty and Stock) which is identical with the 2, 4-dimethyl-3-ethyl
H3C.C C.C2H5
pvrrol = prepared svnthetically bv Knorr and Hess.3
HC—NH—C.CH3
The second haemopyrrol, which he calls isohocmopyrrol ( = haemopyrrol
of Fischer and Bartholomaus, B-haemopyrrol of Piloty and Stock)
is also a trisubstituted pyrrol, namely 2, 3-diinethyl-l-ethylpyrrol
C2H5.O C.CH3
HC—NH-C.CH3
These two dimethylethylpyrrols give with nitrous acid the correspond-
1
Ber. d. d. chem. Gesellsch., 45.
2
Piloty, Annal. d. Chem. u. Pharm., 377, 388, 390, and 392; Willstatter and
Asahina, ibid., 385. In this article will be found on pages 1S9 and 190 the references
to the literature on the investigations of Marchlewski and others on ha?mopyrrol.
H-lFischer and Bartholomaus, Zeitschr. f. physiol. Chem., 77 and 80 and Ber. d. d.
chem. Gesellsch., 45.
3
Piloty and Stock, Annal. d. Chem. u. Pharm., 392; Knorr and Hess, Ber. d.
d. chem. Gesellsch., 44 and 45.
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