14 CYANOGENETIC GLUCOSIDE OF EREMOPHILA MACULATA 



the resinous material obtained on evaporation of the solvent 

 treated with water. The aqueus solution, precipitated 

 by basic lead acetate, and excess of lead removed by HoS, 

 was concentrated under diminished pressure, taken up in 

 alcohol and finally extracted with ethyl acetate. 



The brown syrup obtained on evaporation of the solvent 

 showed no sign of crystallisation even on standing several 

 months, and was without appreciable reducing action on 

 Fehling's solution. 



It was further taken u]) in water when addition of acetate 

 of lead produced further small quantity of yellow precipitate. 



The solution freed from lead and concentrated to a 

 syrup was repeatedly taken up in alcohol and fractionally 

 precipitated by addition of ethyl acetate and ether when 

 small quantities of resinous material were deposited. 



The decanted liquor on concentration in partial vacuo 

 did not cr^^stallise, nor could crystallisation be obtained 

 by use of a mixture of ethjd acetate and toluene as recom- 

 mended by Herissey (J. Chem. Soc. Abr., 110, pt. 1, 31). 



An attempt was made to prepare the acetyl derivative 

 of the glucoside by boiling a quantity of the crude syrup 

 with acetic anhydride. The oil obtained by pouring into 

 water was washed with 5 per cent, sodium hydroxide 

 solution to free from acidic substances and finally thoroughly 

 with water. 



It was completely soluble in ethyl acetate, chloro- 

 form, ether, and 95 per cent, alcohol, and evaporation of 

 the last mentioned solvent yielded a quantitj^ of rhombic 

 crvstals. These were purified by two crystallisations from 

 hot 95 per cent alcohol and were found to melt sharply 

 at 123 degrees C. 



This melting point is identical with that of tetra-acetyl- 

 prulaurasin, though from its sparing solubility in cold 

 alcohol and its crystalline form it could not be identified 

 with that substance. The amount available did not permit 

 of further experimental work. Cooling of the mother 

 liquors to— 5 degrees C. gave a further quantity of similar 

 crj-stals, and also a small quantity of needles, apparently 

 orthorhombic, though it was found impracticable to effect 

 the separation of the two substances. 



