212 Prof. W. R. Dunstan. On the Occurrence of [June 6, 



with lime. Nencki (' Journ. fur Prakt. Chem.,' vol. 20, 1879, p. 466) 

 by a series of analyses of skatole and its picrate, showed that the 

 composition of the substance is expressed by the formula C 9 H 9 N, and 

 that it might be regarded as the methyl-derivative of indole (C 8 H 7 N"), 

 a compound which is associated with skatole in the faeces, and which 

 is also produced during the putrefaction of albumen. In 1880 von 

 Baeyer (' Deutsch. Chem. Gresell. Ber.,' vol. 13, p. 2340) described a 

 method of preparing skatole, together with indole, from indigo, which 

 was reduced with tin and hydrochloric acid, and the resulting reduc- 

 tion product distilled with powdered zinc. Three years later, in 

 1883, Otto Fischer and German achieved a synthesis of skatole 

 (' Deutsch. Chem. Gesell. Ber.,' vol. 16, p. 710) by heating glycerol 

 with a compound of zinc chloride and aniline, C 6 H 7 X 4- C 3 H 8 3 == 

 C 9 H 9 N + H 2 0. Fileti (' Gazz. Chim. Ital.,' vol. 13, p. 350) in the same 

 year prepared skatole by distilling the barium salt of orthonitrocumic 

 acid with powdered zinc, C 9 H n N"0 4 + 3Zn = 3ZnO 4- H 3 -f C 9 H 9 N, 

 and he inferred from this synthesis that skatole is Pr-3 methyl 

 indole, an inference which has since been fully substantiated. 



Quite recently a most interesting synthesis of skatole has been made 

 by Emil Fischer (' Liebig^'s Annalen,' vol. 236, 1886, p. 137) from pro- 

 pylidene phenylhydrazide. This compound when heated with zinc 

 chloride yields ammonia and Pr-3 methyl indole (skatole), 



C(CH 3 ) 



Ph.N a H:CH.CH 3 CH 3 = NH 3 + C 6 H 4 <— C>CH. 



IN hi 



Neither skatole nor indole has hitherto been observed to occur in 

 plants. They have appeared to be characteristic products of the 

 bacterial resolution of animal proteid. 



Among the many plants collected by the late Daniel Hanbury, 

 F.B.S., and now deposited in the Museum of the Pharmaceutical 

 Society, there was a small specimen of wood to which the Curator, 

 Mr. E. M. Holmes, drew my attention on account of it intense odour, 

 which recalled that of a-naphthylamine. Since »-naphthylamine has 

 not been noticed as a plant constituent I determined to examine the 

 specimen, which was labelled Geltis reticulosa, Java. It was evi- 

 dently the wood of a large tropical tree. 



In order to be well assured of the identity of the specimen I applied 

 to Mr. Thiselton Dyer for information about this plant, and I am 

 greatly indebted to him for the trouble he has taken in ascertaining 

 what is known on the subject. Mr. Dyer informs me that " Celtis 

 reticulosa was the name given by Miquel to a tree growing in Java. 

 Planchon subsequently identified the species with Geltis cinnam,omea 

 of Lindley.(De Candolle's ' Prodromus,' vol. 17, p. 181), which occurs 

 throughout Eastern India and Ceylon. Thwaites regards the Ceylon 



