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38 REPORT OF SCHIMMEL § Co. OCTOBER 1914/ APRIL 1915. 
The needle oil from Pinus heterophylla had an odour similar to that of pine-needle . 
oil from Abies alba, reminding at the same time of higher fatty aldehydes. We ascertained 
the following constants: di500,8879; %) — 35° 23’; np20o 1,48568; acid v. 0,6; ester v. 10,1; 
soluble in 7 volumes and more of 90 p.c. alcohol, with turbidity. About 70 p.c. of the 
oil distilled up to 72° (3 mm.). Treated with neutralized bisulphite solution, the residue 
formed a small quantity of a solid bisulphite compound which, when distilled with 
steam in presence of soda solution, produced traces of a semi-solid body, the odour 
of which reminded distinctly of lauric aldehyde. The semicarbazone remained of 
paste-like consistence. On account of the small quantity at our disposal it could not - 
be purified. The high-boiling parts, which did not react with bisulphite, smelled like 
sesquiterpene. 
In the fractions which passed over up to 72° (3 mm.) we proved: Locale 
(b. p. 162°; a) —24° 37’; nitrosochloride, m.p. 103 to 104°; nitrolbenzylamine, m. p. 123 
to 123,59), 7-@-pinene (b. p. 102 to 163°; nopinic acid, m.p. 125 to 126°) and possibly 
also camphene. On hydrating the hydrocarbons boiling between 162 and 163°, a solid 
mass was formed, which smelled distinctly of zsoborneol; through oxidation with Beck- 
mann’s mixture we obtained a product smelling like camphor. The quantity was too 
small to permit of purification. 
The needle oil from Pinus palustris also resembled the oil of Abies alba in odour. 
diso 0,8849; a) — 30°15’; nyo 1,48277; acid v. 0,9; ester v. 4,6; soluble in 6 volumes 
of 90 p.c. alcohol, with slight opalescence. About 57 p.c. of the oil passed over up 
to 40° (6 mm.). By means of neutralized bisulphite solution, a body was separated 
from the residue, which smelled of lauric aldehyde. The high-boiling parts of the 
oil smelled like sesquiterpene. In the fractions of the b.p. 164 to 165° (dis0 0,8701; 
&y — 17°) we found l-a-pinene (nitrolbenzylamine, m. p. 123 to 124°) and (-pinene 
(nopinic acid, m. p. 125,5 to 126°). From 18g. of this fraction we obtained, by single . 
oxidation, 5 g. of a purified sodium nopinate. 
Needle oil from Pinus ponderosa. This oil, too, resembled the oil from Abies alba 
in odour. It did not react with neutralized bisulphite solution. It had the following 
properties: dis0 0,8796; @) —17° 16’; Npx»0 1,48033; acid v. 0,6; ester v. 8,6; soluble in — 
5,9 volumes and more of 90 p.c. alcohol. About 10 p.c. of the oil boiled between 
159 to 164°, producing a small quantity of a nitrosochloride melting at 104°, which 
points to the presence of «-pinene. About 50 p.c. boiled from 164 to 170° (4p — 18° 38’) 
and contained /-8-pinene (nopinic acid, m.p. 1260 to 126,5°). With a single oxidation 
12 g. of this fraction yielded 5 g. of purified sodium nopinate. The fractions boiling 
above 176° were treated in the usual way with phthalic anhydride, resulting in traces 
of an alcohol smelling of borneol. 
We may add that this oil is obtained on the Pacific coast as a by-product in 
the manufacture of so-called pine-needle wool (forest wool) (Lana pint) which is used in 
the manufacture of mattresses’). 
Oil of Ramona stachyoides. On page 107 of our Report April 1912 we mentioned 
a paper by F. Rabak on the oil of the labiata Ramona stachyoides. Further particulars 
on the composition of this oil are found in a publication by C.E.Burke and C.C. Scalione*) 
who distilled the oil from leaves and twigs collected in February, obtaining a yield of 
0,9 p.c. Due consideration must be given to the fact that the raw material had slightly 
1) Gildemeister and Hornaasn, The Volatile Oils, 2°4 ed., vol. II, p. 132. — %) Journ. Ind. Eng. Chemie, i 
6 (1914), 804. 
