450 BROOKS. 



Preparation of the free coloring matter, narrin, from the copper 

 or lead salts by hydrogen sulphide yielded narrin which retained the 

 solvent from which it was prepared most tenaciously, causing variable 

 results on analysis. 



Fusion of narrin with caustic potash yielded phloroglucine, identified 

 by the pine splint test, and resorcinol, which was detected by forming 

 fluorescein by heating the residue from the ether extract with phthalic 

 anhydride. 42 



Slow oxidation of 12 grams of narrin with 10 grams of potassium 

 permanganate in alkaline solution and extraction with ether gave 0.5 

 gram of substance having a strong odor of vanillin. The color reaction 

 with ferric chloride indicated its presence. Addition of phe^dhydrazine 

 acetate to the aqueous solution of the extract gave the crystalline phenyl- 

 hydrazone which melted at 104°. Four grams of narrin, apparently 

 unchanged, were recovered. JSTo other products of the oxidation were 

 identified. 



The benzoyl derivative obtained by the Baumann-Schotten method 

 was an amorphous, brown mass which could not be crystallized. Dilute 

 nitric acid yielded a yellow resin. 



Narrin is not a glucoside. 



This was shown by heating 10 grams of the dye, which had been extracted by 

 neutral solvents, on the water bath for one hour with a 2 per cent solution of 

 caustic soda, acidifying slightly and adding a solution of phenylhydrazine acetate. 

 The warm solution was then placed in the ice box for twenty-four hours. No 

 osazone nor other crystalline precipitate resulted. The precipitated coloring 

 matter was dried, dissolved in alcohol and the copper salt precipitated by alcoholic 

 copper acetate. The copper salt thus prepared on ignition gave G.53 per cent 

 copper oxide. 



Narrin chars on. distillation with zinc dust and yields a small amount 

 of resorcinol dimethyl ether. 



The dyeing properties of narrin are similar to those of santalin. 

 It is quite insoluble in water, but dissolves readily in alkaline solutions, 

 such as an infusion of wood ashes. Metallic mordants such as chro- 

 mium and copper hydroxides are the most suitable. The shades pro- 

 duced are not very fast to soap. 



Owing to the fact that neither narrin nor any of its derivatives could 

 be obtained in a crystalline state its study was not continued. 



The two colorless crystalline compounds are sparingly soluble in cold alcohol 

 and separate from a concentrated extract on cooling. Of the two, pterocarpin is 

 much more insoluble in this solvent and can easily be separated from homop- 

 terocarpin by crystallization from the hot solution. Pterocarpin is described by 

 Cazeneuve and Hugonenq 4S as a body crystallizing from chloroform in colorless, 

 monoclinic plates, melting with previous softening at 152°. I isolated, in all, 



^Mulliken, S. P. Identification of Pure Organic Compounds (1905), 1, 84. 

 "Bull. Soc. chim. Paris (1887), 48, 88. 



