Chemistry of Essential Oils

(Tuis.) #1

COMPOSITE 289


from 30 to 45 per cent. Schimmel & Co.^1 have investigated it, and find
a very small quantity of phellandrene and cadinene and the merest traces
of pinene present. In addition to these bodies, the oil contains free
thujyl alcohol and its acetic, isovaleric, and palmitic esters. The blue
compound present is probably azulene. A pure sample examined by
means of the acetylation and saponification methods gave results
equivalent to 14 per cent, of thujyl alcohol and 15 per cent, of thujyl
acetate. The oil is frequently adulterated, the favourite adulterant being
turpentine. This is best detected by distilling 10 per cent, from the oil.
This fraction should dissolve to a clear solution in twice its volume of
80 per cent, alcohol. The presence of even a very small amount of
turpentine upsets this test. Wormwood oil has a tonic and stimulating
effect on the digestive organs, and is sometimes also used externally. It
is a constituent of the well-known liqueur, absinthe.
Paolini and Lomonaco^2 find that the Italian oil contains 10 per cent,
of a mixture of alpha and beta-thujone, which are identified by means of
their semicarbazones, and about 48 per cent, of thujyl alcohol, which
was separated in the form of its phthalic acid ester. Phellandrene was
also isolated as its nitrosite, melting at 105°, and cadinene was separated in
the form of its hydrochloride. Thujyl alcohol is present in the free state,
and also in the form of acetic, isovalerianic, and palmitic esters. At least
two isomeric thujyl alcohols are present including the deZta-variety.
European wormseed oil (Oleum cina) is the product of distillation
of the unexpanded flower buds of Artemisia maritima, although other
species probably contribute to the commercial oil. (" American worm-
seed " oil is the product of one of the Chenopodiacece, q.v.). The plant
is indigenous to the Orient and Southern Russia, Levant wormseed (as.
the buds are termed) being the most highly valued. The principal
constituent of wormseed is the well-known drug santonin, the well-
known anthelmintic. The greater part, if not the whole, of the oil
found in commerce is obtained from the santonin factories, and is said
to differ slightly from the oil distilled from the seeds without extracting
the santonin ; this, however, is very doubtful. The yield of oil is about,
2 per cent. It is a thick yellow oil having the following characters :—
Specific gravity O915 to 0*940
Optical rotation - 1° 30' to - 8°
Refractive index 1-4650 to 1-4690
It is soluble in 2 to 3 volumes of 70 per cent, alcohol.
This oil has been the subject of numerous researches, the results
obtained being extremely variable, no doubt due to difference in the
species of Artemisia used, or to the employment of adulterated oil.
Volckel
8
stated that it was a mixture of bodies to which he assigned
the names cinaebene and cinaebene camphor, without giving any very
definite evidence of their purity. Kraut and Wahlforss^4 found the chief
constituent of the oil to be a substance of the formula C 10 H 18 O. This
body is clearly cineol, which is definitely settled as the principal con-
stituent of the oil. Faust and Homeyer
6
assigned to the principal
constituent the formula C 10 H 16 O. Hell and Stiircke,
6
using^ the oil
from Artemisia vahliana, one of the species contributing to the Levant
wormseed, confirmed the presence of cineol C 10 H 18 O. The presence of


(^1) Berichte, April (1897), 51. (^2) Ckem. Zentral. (1915), i. 607.
*Annalen, 38 (1841), HO. (^4) Ibid., 128 (1864), 293.
5
Berichte, 5 (1872), 680. 6 Ibid. , 17 (1884), 1970.
VOL. I. 19

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