— 175 — 



him contain the same M-pinene, mixed with «-pinene of varying rotation. 

 According to Vavon, the three oils under examination are constituted as 



follows: - French 



«-pinene [«]j— 39,5° 63°/o 



^-pinene [«]j — 19,8° 37°/o 



German 



«-pinene [«]j + 24° 73°/o 



/^-pinene [4 — 19,8° 27°/o 



American 



«-pinene [«]j + 7,5° 72°/o 



/?-pinene [«]j — 18,3° 28% 



Vavon was also successful in isolating by fractionation y#-pinene from 

 French turpentine oil, of which the first-named body is a well-known con- 

 stituent. The hydrocarbon solidified at — 50° and boiled at 164°; [«]j — 22,7°. 

 When reduced, it yielded a hydrocarbon rotating [«]j —23,5°, which was 

 identical with «-pinene from Aleppo turpentine oil 1 ), thus proving that 

 «- and /?-pinene yield the same product of reduction. 



Similar conditions were observed by Vavon 2 ) in the case of another 

 pinene derivative, namely pinene hydrochloride, which was purified by 

 five or six crystallisations from ether, and finally melted at about 133°. 

 We tabulate below the rotations observed [<*]j for the fractions of French, 

 German 3 ), and American oil boiling between 155 and 165° and for the 

 corresponding derivatives (hydrochloride and dihydro-body) with ray I =578. 



French Oil. 

 Oil fraction —44,3° —37,5° —30,1° —22,7° 

 Hydrochloride —34,5° —35,2° —36,7° —37,5° 

 Dihydroterpene —21,8° —22,2° —22,6° —23,6° 



German Oil. 

 Oil fraction +27,3° + 19,9° +12,8° +2,9° — 4,3° — 9,6° —16,1° 

 Hydrochloride +20,0° +11,7° + 3,2° —8,0° —16,3° —22,2° —31,2° 

 Dihydroterpene +12,5°+ 7,2°+ 1,8°— 5,3° —10,6° —14,7° —19,1° 



American Oil. 



Oil fraction +8,0° +4,2° —0,7° — 5,7° —10,2° —15,6° —19,1° 



Hydrochloride +5,0° +0,7° —6,8° —12,7° —20,8° —26,8° —32,7° 



Dihydroterpene +3,4° —4,4° — 8,5° —12,7° —17,4° —20,7° 



According to Vavon, if these figures are brought into mathematical 

 relation to each other in the same manner as above, the conclusion is 



x ) Comp. Report April 1910, 166. 



2 ) Compt. rend. 150 (1910), 1428. 



3 ) See note above. 



