( 460 ) 



Chemistry. "On Lupeol" J ). By Dr. N. H. Cohen. (Communi- 



cated by Prof. P. v. Romburgh). 



(Communicated in the meeting of November 24, 190(1). 



Notwithstanding (lie many and beautiful researches of several 



chemists, the structure of cholesterol, which is important also from 

 a physiological point of view, is far from being known. Therefore, 

 Prof, van Romburgh invited me to investigate a substance closely 

 connected with the same, namely lupeol, a phytosterol. For the 

 phytosterols may be included with the cholesterols in one common 

 group "the cholesterollic substances". The original intention was to 

 study the alstol found by Sack *) in "bresk" 3 ). From the "bresk" 

 investigated by me, alstol, alstonol and ïsöalstonol could not be iso- 

 lated, although Sack claims to have found them in the same, but 

 1 obtained a- and ^-amyrin and lupeol. It appeared afterwards that 

 Sack's alstol is not a chemical individual. 



Lupeol was first found by LlKIERNIK ') in the skins of lupin seeds- 

 afterwards Sack') met with it in the bark of Roucheria Griffithiana, 

 whilst -van Romburgh and van der Linden 6 ) demonstrated its presence 

 as a cinnamate in the resin of Palaquium calophyllum. Finally,, 

 van Romburgh proved that Tschirch's 7 ) crystal-albane simply consisted 

 of lupeol cinnamate. The lupeol was prepared from "bresk" by 

 extracting the same first with boiling alcohol. On cooling, a white 

 mass was deposited which, without any further purification was 

 saponified with alcoholic potassium hydroxide. The saponified product 

 was then benzoylated with benzoyl chloride and pyridine and the 

 reaction product treated repeatedly with acetone by heating just to 

 boiling on the waterbath and then filtering off without delay. 



Finally, a lupeol benzoate was left, which after repeated recrystal- 

 lisation from acetone, consisted of fine, flat needles; m.p. 265° — 266°, 

 (corr. 273°— 274°). 



Found C 83.71—83.81 Calculated for C 38 H 54 3 84.07 



H 10.41—10.36 10.03 



These, like all subsequent combustions, were made with lead 

 chromate. 



[«] D = -j- 60°, 75 in chloroform. 



1 ) For a more elaborate description see Dissertation N. H. Cohen. 1906, Utrecht. 



2) Sack. Diss. 1901, Göttingen. 



3 ) Bresk or djetulung is the dried milky juice of some varieties of Dyera. 



4) Ztschr. f. physiol. Ghem. 15. 415 (1891). 



5 ) Sack I.e. 



6) Ber. 37. 3440 Ü904). 



7) Arch, der Pharm. 241. 653 (1903). 



