E aa of his investigations was that with seven samples he ascertained an average 
loss, after six months, of 2.42 per cent. and he found that after 54 months the average 
“a 
- Oil of the leaves of Cryptomeria japonica. The conifer Cryptomeria japonica, 
Don. known by the name of “Sugi”, is a native of Japan where it is planted on a 
_ large scale on account of its wood. The oil from the wood has been examined?) 
- fepeatedly whereas the oil from the leaves has only been described by So Uchida 
- quite recently*). By- distilling green leaves he obtained 0.7 per cent. of a brownish- 
_ loss was 4.70 per cent. The greatest decrease in weight amounted to 7.83 per cent. 
\ 
prow readily mobile oil which boiled at ordinary pressure from 155 to 350°. 
_ The constants were as follows: d22> 0.9217; [@]pis0 19.2994) (10 per cent. solution in 
_ chloroform); Npz0 1.4895; acid v. 1.0; ester v. 6.56; after acet. 14.35. By means of 
E soda solution a small quantity of free acid was separated from the oil but it was not — 
_ sufficient for closer investigation. In the low-boiling parts of the oil d-a-pinene 
_was found: nitrolpiperidine, m. p. 118 to 119°, nitrolbenzylamine, m. p. 122 to 123°. zt 
 8-Pinene could not be proved, but dipentene was identified by means of the tetra-_ 
bromide, m. p. 123 to 124°. The parts boiling between 100 and 180° (15 mm.) were 
examined after acetylation, when it was found that they contained an alcohol C,oHisO, 
boiling at 213 to 2149; d®2 0.9414; [a], + 56.07° (8.98 per cent. solution in chloroform); 
189 
3 Npjse 1.4832. The alcohol could not be completely acetylated. Its odour resembles 
_ camphor as well as peppermint and seems to be of importance for the aroma of the D 
- oil From the high- boiling parts of the oil a twice unsaturated sesquiterpene Cer segs 
was isolated, b. p. 266 to 268°; d®22.0.9335; [a], + 15.19° (6.08 per cent. solution in 
15.50 
_ chloroform); Npw».s0 1.0041. It yielded a liquid dihydrochloride; solid derivatives, such 
; as nitrosochloride, nitrosite, nitrosate, bromide, or hydrate, were not obtained. Cadinene 
“was present in a fraction boiling from 272 to 275°; it formed a dihydrochloride, 
_ m.p. 117 to 118°*). Furthermore the oil contained a sesquiterpene alcohol C,;H2.0O, 
Bb. p. 284 to 2869; d2=2 0.9623; [4]p0 + 16.76° (5 per cent. solution in chloroform); 
a Np».s0 1.5048. The sesquiterpene alcohol was distilled from a fraction b.p. 270 to 280°, 
- which was of dark blue colour and may have contained azulene. The fractions boiling 
_ from 180 to 200° (15 mm.) contained, moreover, an unknown diterpene CooHs2, the 
_ ecryptomerene; m.p. 61°; b. p. 198° (15 mm.); 345° (ord. pressure); -[@]p20— 34.329 s 
(4.69 per cent. solution in chloroform). As it adds no iodine it may be looked upon 
_as a Saturated body. It yields no crystalline derivative with bromine. Even when 
- treated with concentrated sulphuric acid no characteristic compound resulted; on the 
other hand treatment with hydrochloric acid gas changed it to an isomeride of the 
mi. p. 211 to 212°, i. e., 8-cryptomerene. From the saponification liquor of the oil Uchida 
- obtained a body Cog Hes O,, evidently a lactone, as well as caprylic acid (analysis of 
_ the eer salt). ; . ; a : 
\ 
\ 
“vol. Il, p. 137. — #*) Journ. Americ. Chem, Soc. 38 (1916), 867. — 4) The direction of the rotation is not 
given. — *) On page 49 of our Report April 1914 we pointed. out that the isolation of cadinene hydrochloride 
___ by itself could no longer be regarded as a proof of the presence of cadinene, as besides cadinene there are 
_ two other sesquiterpenes which yield cadinene hydrochloride when treated with hydrochloric acid gas. 
2) Americ. Journ. Pharm. 87 (1915), 526. — %) See Gildemeister and Hoffmann, The Volatile Oils, 2"4- ed., 
