A8 REPORT OF SCHIMMEL & Co. APRIL 1914. 
Several years ago we published in our Reports’) a few brief particulars of Seychelles 
clove leaf oil, and we are now able to add to these a few data, as we have in the 
meantime had an opportunity of examining further oils from this source. The con- 
stants now observed range within the following limits: diso 1,0324 to 1,0493, a) —1°40’ 
to —1°53’, eugenol content (estimated with 3 p.c. soda liquor) 78 to 87 p.c., soluble 
in 1 to 1,5 vols. of 70 p.c. alcohol; when more alcohol is added turbidity occurs in 
a few cases. Three samples of clove-leaf oil distilled in Mauritius, which have been 
received by us from the Imperial Institute in London, exhibit exactly similar characters. 
We record the values below: — 
diso oD Np200 Eugenol content 
1,0626 * —1° 1,53814 93 °/o 
1,0610 — (0° 50’ 1,53039 92 °/o 
1,0671 — 0°50’ 1,53914 92 °/o 
| Soluble in 1 vol. a.m. 
| of 70 p.c. alcohol. 
Copaiba Balsam Oil. It is a familiar fact that several investigations”) have 
established the presence in African copaiba balsam oil of considerable proportions of 
a dextrorotatory sesquiterpene, possessing the properties of cadinene, but affording a 
levorotatory hydrochloride. In addition to this sesquiterpene, Deussen®) has found 
that the oil contains about 0,9 p.c. of -caryophyllene. Having occasion to prepare 
cadinene from an African copaiba balsam oil, we examined the first runnings of the 
sample, and submitted 600 grams thereof to careful fractionation. We obtained the 
following principal fractions with more or less constant b. p.: — 
1. 119 to 120° (10 mm.); 246 to 248° (ord. press.) 10 °/o; ap) — 13°7’. 
AS? ,, 2002 K | i dr MO So 
250) ~,.*2912-G,, ey Oi 
2. 123 to 125° (10 mm.); 258 to 263° (ord. press.) — ; ep — 6952’. 
3. 130 to 133° (10 mm.); 267 to 270° (ord. press.) 20 °/o; «+ 50°. 
2h a Zia Jo eT OR 6 
The principal fraction (No. 3) had the same b. p. as cadinene. The other characters 
of the “cadinene-fraction” isolated from the oil were: dis. 0,9261, [@])-+ 60°40’, 
Np»o 1,01112. 
Fraction. 2 (20 gr., 4) — 6° 52’) was tested for caryophyllene. With glacial acetic 
and sulphuric acids it afforded no caryophyllene alcohol, but when nitric oxide was 
passed into the ethereal solution according to Deussen’s method’), we obtained 2,33 p.c. 
of a nitrogenous body, derived from $-caryophyllene. (m. p. 155 to 156° from acetone). 
Deussen obtained 25 p.c. of this substance from a fraction (2) —4° 36’). The oil 
examined by us, therefore, must have contained much less #-caryophyllene than did 
Deussen’s. 
Fraction 1 (100 gr.; dis. 0,9077; [@]) — 13° 21’; tpw0 1,48943); only afforded the 
smallest traces of the nitrogenous body from -caryophyllene, and can therefore have 
contained next to nothing of this sesquiterpene. It yielded neither a solid nitrosochloride 
nor a nitrosite, but it afforded 30 p.c. of a solid hydrochloride, m.p. 117 to 118° and 
[«]p — 36,38° in a 5,09 p.c. chloroform solution. These characters, as well as fusion 
with /-cadinene hydrochloride (in which manipulation the m.p. was also found to be 
1) Report October 1907, 37; November 1908, 48. — 7%) Comp. Report October 1909, 31. — %) Liebigs 
Annalen 888 (1912), 139; Report October 1912, 149. 
