Commercial notes and scientific information. 85 



The principal constituent of the essential oil of primula root is p-m ethyl ether-^- 

 methylresorcylate (4-methoxy methyl salicylate). It melts at 49° and is identical with 

 the so-called primula-camphor 1 ). Its constitution was ascertained by combustion 

 and by saponification into jp-methylether-/3-resorcylic acid (4-methoxy salicylic acid), 

 m. p. 158 to 159°. The acid was identical with the product described by Tiemann and 

 Parrisius 2 ). The constitution of p-methyl ether-/?-resorcylic acid was further ascertained 

 by demethylation with hydriodic acid and subsequent splitting-off of carbonic acid. 

 The result was resorcinol. 



The following equations show the decomposition of primverin by means of 

 fermentation and of acids respectively: — 



I. Decomposition by fermentation: 

 XOOCHs /COOOV 1 ' 



C 6 H 3 - - CuH 19 0. + H 2 = CuH.cOm + C 6 H 3 — OH < 2 > 



\)CH 3 Primverose. \)CH 3 W 



Primverin. p-Methylether-/9-methyI- 



resorcylate. 



II. Decomposition by acids: 

 Primverin + 2H 2 = C 6 Hi 2 0e + C 5 Hi O 5 + p-methylether-^-methylresorcylate. 



Hexose. Pentose. 



By the name of primulaverin the authors designate a body with m. p. 161 to 163°, 

 « D — 66,56°. It crystallises with 2 molecules of water and possesses the same empirical 

 formula as does primverin. It probably results from an isomorphic crystallisation of 

 primverin with primulaverin proper, which latter up to the present has not been isolated 

 in the pure state and which appears to be closely related to primverin. The essential 

 oil which is formed from primulaverin by hydrolysis consists of a mixture of the 

 methyl esters of ^-methylether-/?-resorcylic acid and ra-methoxy salicylic acid. 



It was now an easy matter to ascertain the constitution of the essential oil which 

 is obtained by the steam-distillation of primula root. A quantity of 40 grams of green 

 root was carefully ground up and macerated with water for 24 to 28 hours. In the 

 process of distillation the mass effervesced strongly. 8,56 grams = 0,0214 p. c. of 

 scales with a mother-of-pearl like lustre passed over, while the distillation water was 

 found to contain 26 grams = 0,065 p. c. of a mass consisting to the extent of about 

 75 p. c. of solid matter. The total yield was 0,0864 p. c. The solid mass crystallises 

 from dilute alcohol in needles, m. p. 49 to 51°. The highly-diluted solution has a 

 clearly-perceptible odour of Russian anise; when more highly concentrated its odour 

 reminds first of the cinnamate, and afterwards of the salicylate of methyl- and benzyl- 

 alcohol. When saponified, the solid substance yielded p-methylether-^-resorcylic acid 

 (m. p. 158°); while the saponified liquid portions yielded chiefly m-methoxy salicylic 

 acid (m. p. 142 to 143°). 



With the object of preparing the essential oil of the flowers, water was first poured 

 over the latter, and after 6 hours they were distilled, yielding 0,00C86 p. c. of a pale green 

 oil. The distillation-water contained 0,00826 p. c. oil. The oil consists in part of 

 saponifiable and in part of non-saponifiable constituents. The former again yielded 

 j9-methylether-tf-resorcylic acid and m-methoxy salicylic acid. So far the constitution 

 of the non-saponifiable constituents has not yet been ascertained. 



l ) Comp. Gildemeister and Hoffmann, The Volatile Oils, p. 590. — 2 ) Berl. Berichte 13 (1S90), 2376. 



