MALIC ACID. 177 



not quite ripe. The boiled and filtered juice of these 

 berries is mixed with so much milk of lime, that it 

 still remains slightly acid, and then boiled for some 

 time. During the boiling the neutral calcium salt 

 separates. This is dissolved in nitric acid (diluted with 

 ten times its volume of water), a saturated boiling 

 solution being formed. On cooling, acid calcium ma- 

 late crystallizes out, which is then thoroughly puri- 

 fied by recrystallization. From its solution the insolu- 

 ble lead salt is precipitated by means of lead acetate, 

 this decomposed with sulphuretted hydrogen, and the 

 filtrate evaporated. 



Properties. Crystallizable with difficulty ; deliques- 

 cent in the air ; has a very acid taste ; fusing point, 

 100 ; at 180 it is decomposed, forming water, fumaric 

 acid, maleic acid, and maleic anhydride. The aqueous 

 solution of the acid occurring in nature rotates the 

 plane of polarization to the left. On being heated with 

 hydrobromic acid, it is transformed into bromsuccinic 

 acid ; heated with hydriodic acid, into succinic acid. 

 It is also reduced to succinic acid in the animal 

 organism. 



The neutral salts of the alkalies are deliquescent. The 

 neutral calcium salt C 4 H 4 5 Ca forms large, shining, 

 easily soluble, folious prisms. "When a solution of this 

 salt is boiled, an almost insoluble salt with 1 molecule 

 water of crystallization is thrown down. The acid 

 calcium salt (H.C 4 H 4 5 ) 2 Ca 4- 8H 2 forms large, trans- 

 parent crystals, difficultly soluble in cold water, more 

 easily in hot water. 



Ethyl malate, C 2 H 3 (OH) j QQ SH' is P roduced 



by saturating a solution of malic acid in absolute alco- 

 hol with hydrochloric acid gas. Liquid, not distillable 

 without decomposition. 



Ethyl acetylmalate, C 2 H 3 (O.C 2 H 3 0) j oaOOTfr' 

 is formed by the action of acetyl chloride on the ether, 

 without the aid of heat. A liquid, boiling at 258. 



