— 124 — 



(zl 6 -m-menthenol-8) was formed quantitatively. This possessed an in- 

 tense odour of peppermint and terpineol, boiled at 106 at 20 mm. 

 pressure and yielded a nitroso -chloride melting at 125 . From the 

 latter, carvestrene dihydrochloride (m. p. 52,5°) and carvestrene dihydro- 

 bromide (m. p. 48 to 49 ) were obtained by means of hydrohalogen. 

 The cis-tetrahydro carvestrenediol, which was obtained by shaking with 

 dilute sulphuric acid, melted at 94 . By means of magnesium methyl 

 iodide, water could readily be separated from the dihydro isocarvestrenol, 

 and in this process isocarvestrene (b. p. 176 to 1 77 at 765 mm. press.) 

 together with a diterpene C 20 H 32 (di-isocarvestrene) were formed, the 

 latter of which boiled at from 188 to 190 under 20 mm. pressure. 

 It is remarkable that in the case of isocarvestrene it is not only the 

 values of the refraction, but also the fact that the hydrocarbon did 

 not yield the carvestrene derivatives referred to, which point to the 

 presence of conjugated double-linkings in the substance. 



Cadinene. In a preliminary note, N. Lepeschkin 1 ) reports on 

 case of isomerism in the preparation of cadinene. Cadinene prepared 

 by heating cadinene dihydrochloride (he does not state with what) and 

 possessing the following constants: (b. p. 148 to 149 at 20 mm. pressure; 

 d^o- 0,9172; " D 1,5107; [«] D — 111,28°) was converted by prolonged 

 heating at 180 to 200° into an isomeric compound (b. p. 145 to 148° 

 at 20 mm. pressure; d ^ 0,9061 ; n D20° i>504 J ; [°Jd — 2,80°). Isomerism 

 also occurred when the substance was heated with glacial acetic 

 acid. For the preparation of pure cadinene, for which the constants 

 are given as follows: b. p. 271 to 2J2 at ordinary press.; 149° at 

 20 mm. press.; d~ 0,9183; n D20O 1,5073; [«] D — 110,96°, the treat- 

 ment of cadinene dihydrochloride with sodium alcoholate is recommended. 



Caryophyllene. By oxidising caryophyllene with permanganate 

 E. Deussen 2 ) had previously obtained a body C 15 H 22 4 , m. p. 120,5° 

 which is certainly of a glycol like character. Deussen has recently 

 announced 3 ) that he has isolated two acids from the products of oxi- 

 dation. One of these boiled under 16 mm. pressure between 186 

 and 190, possessed the formula C 10 H 16 O 3 and proved to be a mono- 

 basic ketonic or aldehydic acid, yielding a semicarbazone melting at 

 186°. The second acid crystallised in coarse square columns, melting 

 at 179,5 to x 8o,5°. It was a monobasic acid C 8 H 8 4 , which could 

 not be identified with any known acid. Furthermore, by carrying 



*) Journ. Russ. phys.-chem. Ges. 40 (1908), 698. Quoted from Chem. Zentralbl. 

 1908, II. 1354. 



2 ) Liebig's Annalen 359 (1908), 258; Report November 1908, 178. 



3 ) Berl. Berichte 42 (1909), 376, 680. 



