65 



by the well-known derivatives. The high optical rotation calls for 

 attention. 



By oxidising myrtenol with chromic acid in solution of glacial 

 acetic acid, the aldehyde myrtenal C 10 H 14 O was obtained (b. p. 87 

 to 90 at 10 mm. pressure; d2o° 0,9876; n D 1,50420; mol. refr. found 

 44,96, calculated for C 10 H 14 O/~43, 79; semicarbazone m. p. about 230 ), 

 which could be converted over the oxime (m. p. 71 to 72 °) and the 

 nitrile, in to myrtenic acid C 10 H 14 O 2 (m. p. 54 ). From the properties 

 of the methyl ester of this acid, (b. p. 99 at 9 mm. piessure; d2o° 1,022; 

 n D 1,48616; mol. refr. found 50,55, calculated for C n H 16 2 /~ 49,84), 

 Semmler and Bart el t draw the conclusion that it still belongs to 

 the bicyclic, singly unsaturated system of myrtenol. This view is 

 supported by the fact that it was possible to produce from the ester 

 by reduction with sodium and amyl alcohol, a hydrated myrtenic acid 

 C 10 H 16 O 2 (b. p. 142 to 1 44 at 8 mm. pressure; d 2 o° 1,049; n r> I A%5 I 9'> 

 mol. refr. found 45,9, calculated for C 10 H 16 O 2 45,7) which behaved 

 like a saturated bicyclic acid. Whilst the experiments mentioned up 

 to the present showed that myrtenol is a primary alcohol, possessing 

 the carbon structure of pinene, the oxidation of myrtenol with per- 

 manganate into pinic acid showed the position of the CH 2 • OH-group 

 (see formula). When boiled with 10 per cent, sulphuric acid, myrtenol 

 yielded a hydrocarbon C 10 H 14 (b. p. 55 at 9 mm. pressure; dgo© 0,858; 

 n D 1,49097; «d±o°) which is possibly cymene. 



On the strength of the facts communicated above, Semmler and 

 Bart el t draw up the following formulae for myrtenol and its products 

 of conversion : — 



CH 



jH 3 OOCH g 



CEL HX 



CH HC 



CH 



COOH 



C-CH 2 .OH C.CH 2 C1 CCH 3 COOH 



Myrtenol Myrtenyl chloride Pinene Pinic acid 



Oil of Nardostachys Jatamansi (?). From the drug Kansho-ko, 

 which is popular in Japan as a perfume, and which is probably the 

 rhizome with attached rests of leaves of Nardostachys Jatamansi D. C. 

 ( Valerianacese) , Y. Asahina 1 ) isolated 1,9% °f a greenish yellow 

 pleasantly smelling oil, which readily resinifies on exposure to the 

 air; d 15 o 0,9536; [o] D — ii°3o'; n D8 o 1,571; acid no. 0; sap. no. 45,7; 

 sap. no. after acetylation 66,42. The oil contains a sesquiterpene 

 boiling at 250 to 254 (di 5 o 0,932). 



*) Journ. of the pharm. Soc. of Japan 1907, 355. 



5 



