108 MM. Zwcngcr and Bodcnbcndcr on Cumarine, 



cooling, provided the solution be dilute, large well-defined crys- 

 tals are deposited, while in the mother-liquor there is a new 

 crystal lizable acid which the authors name melilotic acid. 



The crystals above mentioned are readily purified by one or 

 two crystallizations from alcohol, and consist then of transparent 

 colourless rhomboidal plates, or, when rapidly formed, of silky 

 needles. The body has the odour of cumarine from tonka beans, 

 but somewhat feebler. The solution has an acid reaction, and 

 produces precipitates with basic acetate of lead and with sesqui- 

 chloride of iron, in which respect it differs from the cumarine 

 from tonka beans. The composition was found on analysis to 

 be O 36 H 16 10 . On further investigation, this substance was 

 found to be a compound of cumarine with melilotic acid ; for on 

 treating it with ammonia, the acid was dissolved out and the 

 residue, purified by recrystallization, was found in all its pro- 

 perties, melting-point, neutral reaction, and crystalline form, to 

 be identical with ordinary cumarine. 



To obtain melilotic acid, the aqueous solution of the above- 

 mentioned etherial extract is treated with acetate of lead, by 

 which free melilotic acid, as well as that united with cumarine, 

 are precipitated; the precipitate is extracted with ether and alcohol 

 to remove any free cumarine; the residue, being diffused in 

 warm water, is treated with sulphuretted hydrogen, and the filtrate 

 evaporated on the water-bath until oily drops begin to form. On 

 cooling, the residue cools to a brownish coloured mass of crystals, 

 which are then purified. 



Melilotic acid affects the form of small prisms, which are 

 soluble in water, alcohol, and ether, and its solution has a dis- 

 tinctly acid reaction. It decomposes, on being heated, into 

 water and an oil, which is the anhydride. By nitric acid it is 

 principally changed into picric acid. Its salts are mostly crystal- 

 lizable, and soluble in alcohol and ether. 



Its formula is C 18 H 10 O 6 , and it unites with cumarine,C 18 H 6 4 , 

 to form melilotate of cumarine, C 36 H 16 10 , without the elimi- 

 nation of water. It is probably bibasic, as seems from its decom- 

 position into anhydride and water by being heated, and also by 

 its forming acid salts. It is constituted according to the general 

 formula O H w ~ 8 0°', and accordingly belongs to the salicylic acid 

 series. It is isomeric with phloretic acid, and only differs from 

 cumaric acid, C 18 H 8 G , by containing 211 more. 



Erlenmeyer found* that iodide of propyle was formed by the 

 action of excess of hydriodic acid on glycerine. This iodide, 

 when treated with oxalate of silver, yields oxalate of propyle, 

 from which propylic alcohol, G 3 H 8 O, was obtained by the action 



* Zeitschrift fur Chemie, part 13, 1863. 



