August 12,1871.] 
THE PHARMACEUTICAL JOURNAL AND TRANSACTIONS. 
131 
say it is no work ; it is a real pleasure to do anything 
for this Conference. It is really a work of love. 
Professor Wright, D.Sc., read the following paper on 
The Oxidation Products of Essential Oil of 
Orange-feel (known as “Portugal”). 
RY C. R. A. WRIGHT, D.SC., 
Lecturer on Chemistry in St. Mary's Hospital Medical School, 
AND CHARLES H. TIESSE, 
Assistant Analyst in St. Thomas's Hospital. 
Preliminary Notice. 
Through the kindness of Messrs. Piesse and Lubin, 
we have been enabled to examine a specimen of pure oil 
of orange-peel. As stated by Soubeiran and Capitaine, 
and by Dr. Gladstone, this oil consists principally of a 
hydrocarbon, hesperidine, boiling at 174°, and of formula 
C 10 H lf) . We found that the crude oil commenced to boil 
at 175°, and that 97*2 per cent, by weight came over be¬ 
low 179°; the remaining 2-8 per cent, was a yellow, 
resinous substance, not volatile without decomposition, 
sparingly soluble in alcohol even when boiling, but very 
soluble in ether. In water it was almost insoluble, but 
it communicated to it the bitter taste of fresh orange- 
peel. At 100 ° it was perfectly fluid, but did not entirely 
solidify even after standing some days at the ordinary 
temperature. After complete expulsion of hesperidine 
by long-continued heating to 100 °, it was perfectly in¬ 
odorous; it contained no nitrogen, and on combustion 
yielded numbers agreeing with the formula C^H^Og. 
Hesperidine is readily acted on by nitric acid; if un¬ 
diluted a violent action ensues, a viscid, yellow, tarry 
substance being formed; but if diluted with its own 
bulk of water, nitric acid acts more slowly. By long- 
continued boiling, an inverted condenser being attached, 
the evolution of red fumes and carbonic acid is noticed 
for some hours, and then almost ceases; the hydro¬ 
carbon is then found to be converted into a brown resin, 
becoming very soft at 100 °, but hard and brittle after 
cooling. This resin contains a large quantity of nitro¬ 
gen, and is apparently foimod from the original body 
by addition of oxygen and replacement of hydrogen by 
N 0 2 . Its examination is not yet completed. 
By the action of stronger nitric acid on this brown 
resin, a yellow resin not softening at 100 °, and contain¬ 
ing less carbon and hydrogen, is produced. The forma¬ 
tion of this body is accompanied by the production of 
much oxalic acid, and possibly of a nitrogenized acid, 
as the snow-white oxalic acid obtained after precipita¬ 
tion, as lead salt, decomposition by hydric sulphide, and 
several recrystallizations contained nitrogen, and gave 
numbers on analysis (as well as its silver salt) approxi¬ 
mating to, but not agreeing very well with, those 
required by theory. 
On heating 1 part of hesperidine with 30 of water, 1 
of sulphuric acid, and 3 of potassium dichromate, a 
slow evolution of C0 2 is noticed. After some hours 
boiling with an inverted condenser attached, the majo¬ 
rity of the hydrocarbon is apparently unattacked, but 
on distilling an acid distillate is obtained. This acid, 
converted into barium salt and silver salt, gave num¬ 
bers indicating that the acid was essentially acetic. 
The barium salt also gave all the qualitative reactions 
of an acetate. 
Sulphuric acid and potassium chlorate have a violent 
action on hesperidine, and produce a viscid tar not yet 
fully examined. 
The President said that this short communication by 
Professor AVright was only another proof that he was 
working in the right direction. He seemed to have hit 
the nail on the very head. This paper accounted for 
the difficulty they had of preserving the essential oil of 
orange-peel. No doubt the changes referred to would, 
go to explain the change essential oil of orange-peel 
undergoes. 
Mr. Hanbury said he supposed the gentleman who* 
read the paper had not found the source of this essential 
oil; whether it was got from home or abroad—from the. 
bitter or sweet orange. He thought it would be in¬ 
teresting to know about that. 
Professor Wright said all he knew was that it was- 
received from Piesse and Lubin, from abroad, and that 
it was as pure a material as could be made. He ob¬ 
tained the article from the firm referred to ; but as to 
the nature of the orange from which it was derived, he; 
was not acquainted with it. 
Dr. Attfield said that there were many gentlemen 
present who would feel as he did, that they should re¬ 
cognize the labotu’s of Professor AVright, by thanking, 
him for his paper. It was one of those gems of research 
as to which he thought they would be insulting the 
work of Dr. AVright if they alluded to the mere practical 
application of such a paper. The practical application 
of these matters was far lower than the research itself, 
and sure to follow in the ordinary course of events. As 
to votes of thanks to authors of papers, it might be welt- 
to wait till the end of the meeting, and then thank the- 
authors all at once. Authors of papers themselves gene¬ 
rally said that they were so abundantly gratified in 
making the researches, that they did not care much for 
the thanks, and were willing to put off to the end of the 
meeting any recognition of their services in this respect. 
It was agreed to postpone giving thanks till the close- 
of the meetings. 
The President said that the next paper was one of 
great ability, on “ New Derivatives from Codeia.” Ho 
was sure that that paper alone would repay them for- 
coming to Edinburgh to hear it. 
Professor AVright then read the following paper:— 
New Derivatives from Codeia. 
BY CHARLES R. A. WRIGHT, D.SC., 
Lecturer on Chemistry in St. Mary's Hospital Medical School. 
By the action of hydrobromic acid (48 per cent. HBr), 
on codeia at 100 ° F., there is produced firstly a base con¬ 
taining the elements of codeia, where O H is replaced by 
Br ; and by a further action two other bases, one con¬ 
taining one atom of oxygen less than codeia, the other 
having the composition of four molecules of codeia, 
coalesced together, one of the 84 hydrogen atoms in the- 
product being replaced by Br. 
Codeia.Qis^iNOg 
Bromocodeide .... C 18 H 20 BrNO 2 
Deoxy codeia .... C 18 H 21 N0 2 
Bromotetracodeia . . . C^HggBrNjO^ 
The last base is almost insoluble in ether, whereby it 
can be separated from the other two, which are readily 
soluble in that menstruum. 
The further action of hydrobromic acid on the above 
bodies gives rise to the substitution of H for C H 3 in 
them, the following substances being obtainable by this 
means: — 
Deoxymorphia.C 17 H 19 N0 2 
Bromo-dicodeia-dimorphia . C 70 H- 9 BrN 4 O 12 
Bromototramorpliia . . . C f)8 H 7i BrN 4 0 12 
AA r hen treated with strong hydrochloric acid at the 
ordinary temperature, the bromine in the tetra-bases de¬ 
scribed above is replaced by chlorine. Thus, the follow¬ 
ing bodies have been analysed (*. e. their salts) :— 
Chlorotetracodeia .... C 72 H 83 C1N 4 0 12 
Chloro-dicodeia-dimorphia . C 70 H 79 ClN 4 O 12 
C'hlorotetramorphia . . . C 68 H; 5 C1N 4 -0 13 
The physiological action of the above bodies does not 
