THE CHEMISTRY OF CHLOROPHYLL 4 39 



reaction which took place was the elimination of magnesium. 

 A product was thereby obtained which, unlike chlorophyllin or 

 alkachlorophyll, possessed no acidic characters, but was a 

 neutral product, to which the name phceophytin l was assigned. 

 This substance on hydrolysis with alkali yields the alcohol, 

 which has been already mentioned, which possess a composition 

 corresponding with the formula C 2 oH 4 oO, and to which the name 

 phytol was assigned. 



Phaeophytin was prepared by treating the alcoholic extract 

 of leaves with just sufficient oxalic acid ; it separates out as a 

 product somewhat insoluble in alcohol, and was freed from its 

 admixtures by repeated solution in chloroform, and precipitation 

 from this solution by means of alcohol. The product obtained 

 in this way possesses neither marked acidic nor basic properties ; 

 it is a wax-like substance, which in solid form is almost black, 

 and which gives rise to dark olive-brown fluorescent solution. 

 The products obtained from various sources did not all have the 

 same chemical composition ; some specimens obtained from the 

 same species of plants, but from different harvests, varied. The 

 reason of this is due to the admixture of another closely allied 

 substance which will be alluded to later. The phaeophytin 

 from different sources yields, furthermore, for the same reason, 

 on treatment with alcoholic solutions of caustic alkalis varying 

 quantities of phytol. Thus a sample of phaeophytin from grass 

 yielded 32 per cent, of its weight of phytol, whereas one from 

 pines yielded only 14 per cent. The phaeophytins from various 

 sources yielded on hydrolysis with alcoholic potassium hydroxide 

 or by strong acids varying quantities of mixtures of the different 

 phytorhodins and phytochlorins. 



The alcohol phytol, C H 4 oO, obtained by the hydrolysis of 

 phaeophytin, is a clear colourless oil which boils at a temperature 

 of 145° under a pressure of 0*03 — 0*04 mm. It does not distil 

 without decomposition if the pressure be much higher, and it 

 cannot, therefore, be fractionated in an ordinary vacuum. It can 

 be readily oxidised by potassium permanganate and also chromium 

 trioxide. The esterification constant was determined by the Men- 

 schutkin method ; this constant was not far removed from that of 

 allyl alcohol; its behaviour agreed generally with that of a primary 



1 With regard to the nomenclature, Willstatter proposes to adopt the termination 

 ''-phytin " for the products derived by treatment of chlorophyll with acids, and 

 ''-phyllin " for those containing magnesium and derived by the action of alkalis. 



