434 THE CHEMICAL EXAUINATIOX OF IIACROZAMIA SPIRALIS, 



Examination of the Resins, C. 



The resinous mass insoluble in hot water, which was left in the still after 

 the removal of the volatile eonstituents by steam distillation, when dry weighed 

 392 gms., or 40 ^c of the total contents of the alcoholic extract . 



This substance was a dark brown powder. It was dissolved in the smallest 

 amount of alcohol, mixed witli purified sawdust and completely dried to constant 

 weight. The dried mass thus rendered porous was transferred to a Soxhlet ap- 

 paratus, and extracted successively and completely with petroleum spirit (b.p. 

 below 50° C), ether, cldoroform, and alcohol. After each of these extracts was 

 distilled to remove the solvent, and the residues dried at 110° and weighed, the 

 following results were obtained : — 



1 . Petroleum sjiirit extract 35 gins . 8.9% 



2. Ether extract 38 „ 9.7 



3. Chloroform extract 4 ,, 1.0 



4. Alcohol extract (iO „ 15.4 



Left unextracted 255 „ 05.0 



Total 392 .. 100.0 



This table shows that although 392 gms. of this mixture originally were in 

 alcoholic solution, being extracted from the leaves with this solvent, 255 gins, had 

 now liecome insoluble in that liquid, forming nearly two-thirds of tlie original 

 extract . 



Two factors may explain this anomaly: — The i)etroleum spirit extract con- 

 tains all the oils and fats. Certain substances are intimately associated in tlie 

 plant with these oils and are soluble in them alone. 'I'licy are removed together 

 ■with the oils in the extraction of the leaves by alcohol. When subse(|uently the 

 oils and fats are removed by petroleum spirit these other constituents, having 

 lost their special solvent, are now rendered completely insoluble in alcohol. In 

 the second place the leaves were originally extracted with 80 % alcohol (contain- 

 ing 5 % wood-spirit), and in the resin analysis 98 9r ethyl alcohol was used. 



i. Petroleum spirit extract of the Ttesins. — The solvent was removed by 

 distillation, and the residue of 35 gms. was dissolved in ether leaving a small 

 amount of insoluble brown residue, which weighed 0.2 gm. The ethereal solution 

 was then agitated a number of times with (1) ammonium carbonate, (2) sodium 

 carbonate. (3) sodium hydroxide, . (4) water, for the separation of organic acids. 

 The alkaline extracts were rendered acid with sulphuric, and shaken back with 

 ether, the solvent distilled off, and the residue examined. In this way (1) am- 

 monium carbonate yielded 0.25 gm. of a grey amorpjious residue. (2) The 

 sodium carbonate extract yielded a small <|uantity of a dark brown oil. At the 

 same time there was precipitated by sulphuric acid about 10 gms. of a brown 

 solid substance. The latter with the acid fluid was distilled in a current <if 

 steam, hut from the distillate only a trace of volatile acids was obtained. Tlie 

 acid liquid remaining in the still, however, when titrated \v\th baryta snhiticm 

 and evapoiated, yielded the barium salt of acetic acid. 



0.4(i0 gm. Ra salt gave 0.410 gm. BaS04=89.2% 

 Barium acetate requires „ =-01.3 

 The amount was eiiual to about 0.7(1 gm. of acetic acid. The l)ro\vii solid sub- 

 stance mentioned above, of 10 gms. weight, was treated witli petrdlcum spirit 



