— i8 — 



allyl-(i)-phen-(3, 4)diol, from which are derived both eugenol and 

 chavibetol, and also safrol: — 



OH 



OH OCH 3 



CH 2 / NoH CH 2 :CH.CH 



2 / ^>OCH 3 CH 2 :CH.CH 2 / NoH 



Allyl pyrocatechol 



Chavibetol Eugenol 



OCH 3 

 CH 2 :CH.CH 2 / ^>OCH 3 



CH 2 



CH 2 :CH.Ch/ / Q// 



Eugenol methyl ether 



Safrol (allyl pyrocatechol 

 methylene ether). 



Eugenol and chavicol could not be detected in the oil, although 

 we made a thorough examination of the chavibetol fraction for 

 this purpose. 



We next turned our attention to the oil of betle leaves from which 

 the phenols had been removed, and found in it still the following 

 bodies. The lowest boiling portions of the oil (b. p. 155 to 162 , 

 43 to 45 [4 mm. pressure], «r> — 9° 4') were tested for pinene, but 

 no solid nitroso chloride could be separated off. The fraction distilling 

 at 170 to 176 contained cineol. The iodol double compound, 

 purified from benzene, melted at 11 2°, and when heated with caustic 

 soda liquor developed the characteristic cineol odour. An oil passing over 

 between 100 and 107 (4 mm. pressure) boiled at ordinary pressure 

 chiefly at 247 to 254 , and on oxidation with permanganate according 

 to Tiemann's and Matsmoto's directions 1 ) yielded a very small 

 quantity of an acid melting at 179 , which quantity, however, was 

 sufficient to identify it as veratric acid. From this it appears probable 

 that the eugenol methyl ether was a constituent of the oil in 

 question. Finally, caryophyllene, which formed the principal con- 

 stituent of the phenol-free oil, could be identified by the nitrosate 2 ) 

 of the m. p. 1 5 8°. It was detected in a fraction with the following- 

 properties: b.p. 258 to 261 , di 5 o 0,9131, aD-f-o^z]/, n D20 o 1,50720. 

 A fraction of the approximate b. p. 275 and the further properties of 

 cadinene 3 ), which was present in the oil examined by Bertram and 

 Gildemeister, was not observed. 



The foregoing examination has consequently shown that oil of 

 betle leaves contains in addition to the already known constituents, 

 allyl pyrocatechol, a terpene, cineol, eugenol methyl ether, and 

 caryophyllene. 



x ) Berl. Berichte 9 (1876), 937. 



2 ) The m. p. of caryophyllene nitrosate is given in literature erroneously as 148 . 

 According to our repeated observations it lies at 15 8° (comp. Report April 1904, 76). 



3 ) Journ. f. prakt. Chem. II. 39 (1889), 355. 



