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ILfflMATOPOKPHYRIN. 295
to Piloty two carboxyl groups axe formed with the taking up of water and
these occur to a certain extent latent in lactam combination in the baemin.
According to Kusteh, 1
who admits of two already funned carboxylfl in the ha-min,
two bydroxyls are produced secondarily in the fuematoporphyrin, in that (by the
action of the glacial acetic acid and hydrobromie acid) primarily an attachment
of hydrobromic acid takes place and then from this as intermediary product,
by tiie action of water, bromine is split off ami is replaced by hydroxyl. In the
formation of mesoporphyrin the procedure is still different because among others,
mesoporphyrin contains 2 oxygen atoms less than the luematoporphyrin.
On the gentle reduction of hsemin with glacial acetic acid, bydriodic acid
and red phosphorus, Piloty and Fink obtained besides mesoporphyrin a second
body, phonoporphyrin, which differs from the mesoporphyrin by containing
more oxygen, a brown color and almost complete insolubility in dilute hydro-
chloric acid. It is not reduced to mesoporphyrin by hydriodic acid but yields
hsematinic acid and methyl-ethyl maleic imide on oxidation with chromic acid.
They obtained no other cleavage products from hsemin under the above men-
tioned experimental conditions. The two porphyrins were produced in about
equal quantities and they formed about 90 per cent of the calculated cleavage
products. They each represent one-half of the ha?min, whose formula corresponds
to CesH^XgOsFciCla which must be doubled. As these two porphyrins yield
methyl ethylmaleic imide, while this is not the case with either the haemin or the
hsematoporphyrin, it is believed that both are combined together in the haemin
or ha?matoporphyrin with that part of their molecules which allow of the maleic
imide formation.
By the action of glacial acetic acid, and hydriodic acid upon hsemin in the
cold (room temperature) in the presence of iodophosphonium, H. Fischer and
Bartholomaus have obtained a beautiful crystalline, colorless product, por-
phyrinogen, whose formation and behavior have been further studied by Rose. 2
Porphyrinogen, C.^H^NjO^ is formed from hsemin, the meso- and the hsemato-
porphyrin in acid, and from the meso- or hsematoporphyrin also in alkaline
reduction. Porphyrinogen can be transformed into mesoporphyrin by oxidative
action of various kinds. Like the latter it yields hsematinic acid as well as methyl
ethyl maleic imide as oxidation products.
Haematoporphyrin is closely related to the bile pigment bilirubin
(see Chapter VII) and also stands in close relation with the urinary
pigment, urobilin. By action of reducing substances several investiga-
tors (Hoppe-Seyler, Nencki and Sieber, Le Nobel, MacjMunn and
others) have obtained pigments similar to urobilin, and by experiments
with rabbits, Nencki and Rotschy3 have proved that haematoporphyrin
introduced into the animal body may in part be transformed into a
urobilin substance.
In connection with the question of the behavior of haematoporphyrin in the
animal body, the poisonous action of this body, as discovered by Hausmann,
and which manifests itself as a photobiological sensibilisation, is of interest.
Hausmann has found that white mice that have had fuematoporphyrin injected
1
Piloty, 1. c; Kiister, Ber. d. d. ehem. Gesellsch., 45.
2
Piloty and Fink, Ber. d. d. chem. Gesellsch., 46, 2021; H. Fischer and Bartholo-
maus, ibid., 46, 511; Rose, Zeitschr. f. physiol. Chem., 84.
3
Hoppe-Seyler, Med. Chem. Unters. p. 533; Le Xobel, Pfluser’s Arch., 40;
Nencki and Sieber, 1. c; MacMunn, Proc. Roy. Soc, 30, and Journ. of Physiol., 10;
Nencki and Rotschy, Monatsh. f. chem., 10.
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