( 47(1 ) 



On saponification with alcoholic potassium hydroxide a substance 

 was obtained which crystallised from ether in needles. Placed in the 

 bath at 260°. the melting point was 263 — 265°. In regard to litmus 

 this substance behaves like the unsaponitied product, but it may be 

 again titrated with alcoholic potassium hydroxide and phenolphthalein. 

 From these titrations the molecular weight was found to be 452 

 and 461 ; the formula C„ H 60 0, represents 470,5. 



Found: C 78.42 78.(11 calculated for C„ II, 0, 79.08 

 H 11.07 11.05 10.71 



The potassium compound of this substance is soluble, with diffi- 

 culty, in alcohol, and crystallises from this in needles. 



On treating either the saponified or the unsaponitied oxidation 

 product the same compound was obtained, which seems to be a 

 diacetylated substance. The results of the combustions, however, were 

 not very concordant, but I have not been able to account for this. 

 Found: C 75.:)9 74.71 75.67 74.96 74.47 calcul. for C„ H, 4 0, 75.75 

 II 10.12 10.16 10.51 10.24 9.81 



By boiling with excess of alcoholic potassium hydroxide and 

 titrating with alcoholic sulphuric acid the molecular weight was 

 found to be 549, assuming that the molecule contains two acetyl 

 groups. The formula C, B II,, 6 represents 554.5. 



It is desirable to investigate more closely these oxidation products, 

 which are so important in the study of lupeol, before trying to 

 explain their formation. 



Lupeol is not reduced by metallic sodium and boiling amyl alcohol; 

 whereas lupeon is reduced by sodium and ethyl alcohol to lupeol. 

 Therefore, if lupeon should possess a double bond, this is sure not 

 to be in u ,?-position in regard to the carbonyl group. 



Neither lupeol, nor lupeol acetate dissolved in boiling acetone are 

 acted upon by potassium permanganate. This behaviour does not 

 agree with the theory of a double bond, but the presence of the 

 latter in lupeol and lupeon could be satisfactorily demonstrated by 

 means of Hvbl's iodine reagent. On the other hand the oxidation 

 product C 8S H 52 4 no longer seemed to contain the double bond. 

 On the strength of various combustions and bromine determinations, 

 particularly of dibromolupeon, I consider C 31 H 50 to be the most 

 likely formula for lupeol. The formula C 36 H 42 given by Likiernik : ) 

 and Sack 2 ) is certainly not correct. 



Utrecht, Org. Chem. Lab. University. 



1 ) Likiernik 1. c. 



2) Sack 1. c. 



