March 30, 1872.] 
THE PHARMACEUTICAL JOURNAL AND TRANSACTIONS. 
789 
•composing cresol, we shall, no doubt, in time arrive at a 
proper method for obtaining- them all directly, by treat¬ 
ing the alcohols w r ith nascent hydrogen. 
In subjecting gum guaiac to destructive distillation, 
we obtain a fluid which in many respects hears a great 
resemblance to creasote. This distillate has been espe¬ 
cially investigated by Voelckel and Sobrero and Hlasi- 
w T etz, who succeeded in separating it into two fluids, that 
gave crvstallizable compounds with bases, and which 
they called guaiacol and homo-guaiacol. A later and 
closer study of creasote revealed the fact, that it con¬ 
sisted of these two identical compounds in different pro¬ 
portions. Let us compare them with the products we 
•■obtained from the alcohols of the phenylic series :— 
Chinon, C G H 4 0 2 , Pyrocatechin, C 6 H 6 0 2 
Ivreson, C 7 H G 0 2 , Guaiacol, C-H s 0 2 
Phloron, C 8 H 8 0 2 , Homo-guaiacol, C 8 II 10 O 2 . 
In treating chinon with nascent hydrogen, we obtain 
hydrochinon, and succeed also in producing similar com¬ 
pounds from creoson and phloron, thereby establishing 
the existence of two homologue series of compounds 
having the same composition, but differing in properties. 
Pyrocatechin, C G H G 0 2 , and Hydrochinon 
Guaiacol, C 7 H 8 0 2 , and Hydroereoson 
Homo-guaiacol, C 8 H 10 O 2 , and Hydrophloron. 
Now let us look at the constitution of these compounds. 
It is very probable, and almost admitted by Kekule, that 
cresol is monomethylated pyrocatechin, and homoguaia- 
col or creasol bimethylated pyrocatechin. In fact, in 
treating guaiacol with hydriodic acid we obtain iodide 
of methyl and pyrocatechin, which amounts to a proof 
■of this view, and which gives us two links by which we 
may connect the members of the coal-tar series with 
those of the wood-tar series. To render the constitution 
more apparent to the eye, the formulas may be given thus: 
C g H 5 (OH) Phenol (carbolic acid, coal-tar). 
p rr f OH | Cresylic acid, coal-tar. 
<- 6^4 | CH 3 J Cresol. 
(OH ) 
C G H 3 CH 3 Phlorol. 
(ch 3 ) 
C G H -0 (OH) Pyrocatechin. 
p TT A ( OH 
^ 6±1 -* u \ CH 3 
( OH 
c 6 h 3 o ch 
|ch' 
Guaiacol. 
Creasote, wood-tar. 
Homo - guaiacol. 
It may be stated in further proof for the correctness 
-of considering the above-mentioned compounds as me¬ 
thylated pyrocatechin, that the molecule of methylene, 
■CH.,, may be introduced directly into the constitution of 
pyrocatechin, by heating it in closed tubes with caustic 
potash and sulpho-methylate of potash, producing 
thereby guaiacol. 
The homologues of the phenylic series are crystalli- 
zable compounds of the respective boiling points of 184° C., 
203° C., 220° C., while the two derivatives of pyrocate- 
•ehin are oily liquids boiling at a temperature of 200° C. 
and 219° C. 
Phenol, 184° C. Pyrocatechin. 
Cresol, 203° C. Guaiacol, 200° C. 
Phlorol, 220° C. Creasol, 219° C. 
It can be seen, therefore, that in cases of working with 
mixtures of the individuals of both series, we should 
find it impossible to separate them by fractional distilla¬ 
tions. Their products of decomposition, however, may 
he resorted to as a means of distinguishing between 
them; for while phenol and its series yield with nitric 
acid nitro-phenol and similar compounds, we obtain with 
guaiacol oxalic acid ; chlorine converts phenol into chlo- 
rophenic acid and chloronil; while the products obtained 
in "this way from creasote. though similar to them, pre¬ 
sent differences, which stamp them as peculiar and dis¬ 
tinct bodies .—New York Druggists' Circular. 
ABIETENE, A NEW HYDROCARBON. * 
BY WILLIAM WENZELL. 
This hydrocarbon is the product of distillation of the 
terebinthinate exudation of a coniferous tree indigenous 
to California, and is obtained from the J'imis sabiniana , 
Dougl., a tree inhabiting the dry sides of thb foot hills of 
the Sierra Nevada mountains and the coast range, 
known more familiarly, however, by the name of Nut 
Pine or Digger Pine, names seemingly suggested by the 
edible quality of its fruit, upon which the Digger Indians 
chiefly rely as an article of food. 
During winter the tree is notched and guttered at a 
convenient height from the ground, to receive the resin 
which then exudes, and, when a sufficient quantity is 
thus obtained, it is carried to the stills for distillation. 
As this hydrocarbon is extremely volatile, and, there¬ 
fore, much loss often sustained if the resinous exudation 
is kept long, distillation is usually commenced as soon as 
a sufficient quantity of the “gum” has been collected. 
The crude oil, as usually found in San Francisco, is a 
colourless, limpid fluid, and requires only to be distilled 
to obtain it quite pure. It occurs as an article of com¬ 
merce, and has acquired, during the last eight or ten 
years, a considerable reputation under the names of 
abieteno, erasine, aurantine, theoline, etc., for the removal 
of grease and paint from clothing, fabrics, etc.,—an effi¬ 
cient substitute for petroleum benzine. 
In order to determine whether it was homogeneous in 
its composition, or composed of several hydrocarbons, 
seventeen fluid ounces of the crude abietene were dis¬ 
tilled fractionally, and the several distillates of three 
ounces each separately collected. The first three ounces 
were obtained with the thermometer indicating 101° C., 
the second fraction indicated a thermometric rise of a 
quarter of a degree, and the thermometer rose with every 
succeeding fractional part until the fifth fraction indi¬ 
cated a boiling-point of 104° C. "With the sixth or last 
fraction the thermometer rose rapidly from 105° to 115° 
C., when at this point the distillation was discontinued. 
The remaining ounce presented a brownish-red appear¬ 
ance, and left, on evaporation in a porcelain capsule, a 
small quantity of a solid resinous body. Each fractional 
part was found, on examination, to possess a boiling- 
point of 101° C., showing that the hydrocarbon abietene 
is a homogeneous liquid. Pure abietene is a colourless, 
limpid liquid, possessing a strong penetrating odour, 
bearing some resemblance to oil of oranges. It is speci¬ 
fically lighter than water, turpentine, absolute alcohol, 
and ether, its specific gravity being 0-694 at a tempera¬ 
ture of 16-5° C. It is very volatile and highly inflam¬ 
mable, burning with a brilliant white, smokeless flame. 
It is nearly insoluble in water; soluble in five parts by 
volume of 95 per cent, alcohol. "When poured upon the 
hands it evaporates rapidly, communicating the sensa¬ 
tion of cold. Dry hydrochloric acid, passed through it 
for ten hours, did not react upon it. It dissolves iodine 
with the production of a rich purple colour; bromine is 
also freely dissolved, forming an orange-coloured solu¬ 
tion. Nitric acid of sp. gr. P43 added to abietene occa¬ 
sioned no reaction in the cold, but when the mixture 
was heated to boiling, a moderate reaction was esta¬ 
blished with the disengagement of nitrous acid fumes. 
Concentrated sulphuric acid exerted no reaction what¬ 
ever, either in the cold or on heating; metallic potas¬ 
sium was not acted upon. On passing dry chlorine into 
abietene, this gas was abundantly absorbed, with the 
evolution of hydrochloric acid gas, an increase of volume 
and density, accompanied by a rise of temperature. On 
saturating abietene with chlorine, assisting towards the 
end with a gentle heat, a thick liquid resulted, 'which, 
when heated on a water-bath to remove some hydro¬ 
chloric acid held in solution, was found to possess the 
consistency of glycerine, sp. gr. 1-666, to be colourless, 
insoluble in water, but soluble in warm alcohol, and 
possessing- a taste resembling- balsam ot fir._ 
* Read before the California Pharm. Soc., Dec. 13, 1871. 
