528 CHEMISTRY OF THE PROTEIDS CHAP. 



Relationships of Hsematoporphyrin to other naturally 

 occurring Colouring Matters 



PHYLLOPORPHYRIN. From the green colouring matter of plants, 

 the chlorophyll, 1 and from its dissociation product phyllotaonin, 

 Schunk and Marchlewski 2 and Marchlewski 3 have prepared a colour- 

 ing matter which they call phylloporphyrin. It has the composition : 



C 16 H 18 N 2 0, 



and differs only from hsematoporphyrin in possessing two oxygen 

 atoms less. 4 Marchlewski 3 obtained from it both hsemopyrrol and also 

 haematinic acids. Nencki and Zaleski have made the attempt to 

 convert haematoporphyrin into phylloporphyrin, but only succeeded in 

 removing one of the two hydroxyls of haematoporphyrin, and so 

 reached a product intermediate between haematoporphyrin and phyllo- 

 porphyrin, which they therefore called mesoporphyrin (see p. 527). 

 Spectroscopically mesoporphyrin already resembles phylloporphyrin, 

 according to Marchlewski. 



The red colouring matter of the blood and the green chlorophyll 

 of plants being closely allied substances, are also probably related to 

 the lipochromes (Marchlewski). 5 



H^EMATOIDIN. Derivatives of haematoporphyrin occur also in 

 the animal body, for Virchow 6 discovered in 1847 in blood extrava- 

 sations haematoidin in well-formed rhombic crystals of a brick-red or 

 deep ruby colour. According to Nencki and Zaleski 7 haematoidin is 

 identical with mesoporphyrin, as both exhibit the same colour changes. 



UROBILIN is a reduction compound of haematin or haematoporphyrin, 

 as has been shown by Hoppe-Seyler, 8 Nencki and Sieber, 9 and le Noble. 1(> 

 Urobilin occurs normally in the urine and in the fasces, and is also 



1 L. Marchlewski, Die Chem. d. Chloroph. Leipzig and Hamburg, L. Voss (1905). 



2 E. Schunck and Marchlewski, Liebig's Annalen, 278. 329 (1894) ; 284. 81 

 (1895) ; 288. 209 (1895) ; 290. 306 (1896). 



3 L. Marchlewski, Bull, de I' A cad. des Sciences de Cracovie, CL Math, et Nat. 1902 r 

 January and April, pp. 1 and 223. 



4 M. Nencki, Ber. d. deutsch. chem. Ges. 29. III. 2877 (1896) ; M. Nencki and J. 

 Zaleski, ibid. 34. I. 997 (1901) ; compare also with the papers by Nencki, Sieber, and 

 Steudel quoted on p. 508. 



5 L. Marchlewski, Zeitschr. f. physiol. Chem. 38. 196 (1903). 



6 R. Virchow, Virchow's Archiv. I. 379 and 411 (1847). 



7 M. Nencki and J. Zaleski, Ber. d. deutsch. chem. Ges. 34. I. 997 (1901). 



8 Hoppe-Seyler, ibid. 7. II. 1065 (1874). 



9 M. Nencki and N. Sieber, Arch. f. experim. Path. u. Pharm. 18. 401 (1884) ; 

 Ber. d. deutsch. chem. Ges. 17. II. 2270 (1884) ; Monatsh.f. Chem. 9. 115 (1889). 



10 C. le Nobel, Pfluger's Archiv. 40. 501 (1887). 



