This section is from the book "The Volatile Oils Vol2", by E. Gildemeister.

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241. Oil Of Nigella Damascena

Origin, Production and Properties. The seeds of Nigella damascena, L, known occasionally as
Schwarzkummel, yield upon distillation 0,4 to 0,5 p. c. of an oil with a beautifully blue
fluorescence, which has the agreeable odor and taste ofjuniper berries. d15o 0,895 to 0,9153); aD
+ 1°4' to - 7,8°3); n20o 1,55823). In 90 p. c.alcoholthe oil is but imperfectly soluble, in absolute
alcohol it is soluble in all proportions.
Composition. The principal constituent of nigella oil4) is the alkaloid damascenine,
C10H13O3N, which produces the characteristic fluorescence, and which was first prepared by
A. Schneider5). By shaking the oil with tartaricacidand subsequent decomposition of the tartrate
with soda6), as much as 9 p.c. can be isolated from the oil. The alkaloid can also be obtained by
percolating the comminuted seed with dilute hydrochloric acid, supersaturating the solution with
soda and extracting withpetroleumether. From the petroleum ether solution the chlor-hydrate of
the base can be shaken out in a pure condition by means of hydrochloric acid. In this manner 18
kg. of seeds yielded 110 g. of hydrochlorate1).
1) Berl. Berichte 24 (1891), 2459.

2) Report of Schimmel & Co. April 1895, 75.

3) H. Haensel, Apotheker Ztg. 15 (1911), 28.

4) The statements found in the reports on earlier investigations are largely contradictory. This is
due to the fact that in some instances the seeds of Nigella damascena, L., were examined, in
others those ofNigella sativa, L - H. G. Greenish, Pharmaceutical Journ. III. 12 (1882), 681. -
Reinsch, Jahrbuch f. prakt. Pharm. II. 4 (1841), 385; Pharm. Zentralbl. 1842, 314. - Fluckiger,
ibidem HI. 2 (1854), 161.

5) Pharm. Zentralh. 31 (1890), 173 and 191. Comp. also the inaug dissertation by the same
author, Erlangen 1890.

6) Report of Schimmel & Co. October 1899, 38.

Pure damascenine boils with slight decomposition at 270° (750 mm.)'2) or in vacuum at 157° (10
mm.). It congeals in the cold and melts at 26°. According to A. Schneider it yields crystalline
salts with acids. With platinum chloride, gold chloride, and mercuric chloride, crystalline double
salts result. With the general alkaloidal reagents it produces characteristic precipitates: solution
of iodine in potasium iodide produces a purplish-brown precipitate; potassium bismuth iodide, a
brown precipitate; potassium mercuric iodide and phosphomolybdic acid yield white
precipitates.
The problem of the constitution of damascenine has been attacked consecutively by Schimmel &
Co.3), H. Pommerehne4) and O. Keller5). However, A.). Ewins2) first succeeded in proving the
constitutional formula of damascenine by its synthesis, thus demonstrating it to be the
methylesterof a 2-methylamino-3-methoxvbenzoic acid.

The synthesis of damascenine was accomplished in the following manner: with the aid of
dimethyl sulphate, m-hydroxy-benzoic acid was converted into m-methoxybenzoic acid. When
nitrated, this yielded a mixture of nitro products from which the 2-nitro-3-methoxybenzoic acid
could be isolated without difficulty. This was reduced to 2-amino-3-methoxybenzoic acid which,
when heated with methyl iodide in a sealed tube, yielded the hydriodide of 2-methylamino-3-
methoxy benzoic acid. By heating it with freshly precipitated silver chloride it was converted
into the corresponding hydrochloride (m.p. 210 to 211°) which is identical with the
hydrochloride of damasceninic acid. By passing hydrogen chloride into the methyl alcoholic
solution of the hydrochloride, the hydrochloride of the methyl ester is produced. When hydrogen
chloride is split off, this yields methyl-2-methylamino-3-methoxybenzoate or damascenine (m. p.
23 to 24°). Mixed with thenaturalproduct, this synthetic damascenine suffers no lowering of the
melting point.

1) Arch, der Pharm. 237 (1899), 475.

2) Journ. chem. Soc. 101 (1912), 544.

3) Loc. cit.

4) Arch, der Pharm. 238 (1900), 546; 239 (1901), 34; 242 (1904), 295. 5) Ibidem 242 (1904),
299; 246 (1908), 1.

The seeds of other species of Nigella have also been examined for alkaloids by O.Keller1). In the
seeds of Nigella aristata he is supposed to have found a new alkaloid, methyl-damascenine, in
addition to damascenine. According to Ewins, however, this is an error. The methyldamascenine
of Keller, C10H13O3N, is by him supposed to be identical with the dama-scenine of Nigella
damascena to which the above formula should be assigned. Keller's attempts to isolate alkaloids
from the seeds of Nigella sativa, N. arvensis, N. orientalis, N his-panica, N. Garidella, N.
integrifolia and N. divers/folia by extraction with dilute hydrochloric acid gave negative results.

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