THE CHEMISTRY OF CHLOROPHYLL 431 



transmitted light, separated out, which were purified by dissolv- 

 ing in chloroform and mixing the solution thus obtained with 

 several times its volume of alcohol. When a methyl alcoholic 

 solution was employed a methyl ester of taonin was obtained, 

 and with ethyl alcohol an ethyl ester. Both products were very 

 similar in appearance and properties. They were but slightly 

 attacked by aqueous alkalis, but were readily saponified by 

 alcoholic solutions. In this way phyllotaonin itself could be 

 prepared. It could also be obtained by evaporation of phyllo- 

 cyanin or phylloxanthin with alkalis and acids, and purifying the 

 product by means of chloroform and alcohol in the way already 

 described. It formed crystalline scales which were opaque to 

 transmitted light, and appeared steely-blue in reflected light. 

 It was readily soluble in alcohol and ether, and was also 

 soluble in benzene, carbon disulphide, chloroform, and aniline, 

 Its analyses corresponded with the formula C 4 oH 3 90 6 N 6 . On 

 distilling with zinc-dust it gave a pyrrol-like substance. An 

 acetyl derivative could be obtained from it, although no alkyl 

 esters could be prepared by directly treating it with alcohols 

 and hydrochloric acid. 



Phylloporphyrin. — The most interesting product, perhaps, 

 obtainable from phyllotaonin was that prepared by Schunck 

 and Marchlewski, by heating it in sealed tubes for some hours 

 with alcoholic potassium hydroxide at 190 . On acidifying the 

 mixture thus obtained, and extracting, after acidification, with 

 ether, the latter assumed a purple-red colour, and deposited 

 on evaporation dark violet-coloured crystals mixed with an 

 amorphous brown substance. The alcoholic solution of the 

 product thus obtained gave on treatment with alcoholic zinc 

 acetate a beautiful red crystalline, zinc salt. This was dissolved 

 in hot alcohol, and the solution acidified with hydrochloric acid 

 and thrown into water. The mixture was then extracted with 

 ether, which on evaporation deposited carmine-red crystals 

 which could be purified by recrystallisation from alcohol. This 

 substance was identical with that obtained by Hoppe-Seyler 

 from his chlorophyllan by heating with potassium hydroxide, 

 although it was not prepared by him in a pure condition. It 

 was designated phylloporphyrin, and the name was retained by 

 Schunck and Marchlewski for the product obtained by them 

 from phyllotaonin. 



In its pure condition it was a beautiful dark violet crystalline 



