— 72 — 



Pomeranz supplies the proof of these possibilities only with 

 artificial mustard oil. On oxidation he obtained in addition to 

 much formic acid, also some acetic acid, which could only have 

 been formed from propenyl isothiocyanate. Pomeranz is of opinion 

 that the quantity of the propenyl compound which is formed during 

 the synthesis of mustard oil, is much larger than that found by him, 

 and he surmises that it remains behind in the higher boiling portions 

 during fractionating. 



Oil of Myrrh. A work by K. Lewinsohn 1 ) deals with the 

 composition of myrrh oil. The author has examined three commer- 

 cial oils, and one oil distilled by himself from Herabol myrrh. Not 

 without reason Lewinsohn emphasises that the composition of 

 myrrh oil differs according to the origin of the resin, the method 

 of production, and the age. He suspects that in the factories, as 

 soon as no further oil passes over with the steam, i°/ 00 potassium 

 hydroxide is added to the distillation residue for the purpose of 

 obtaining a larger yield, and the distillation is then continued. In 

 our works such a method is not carried out. Gildemeister and 

 Hoffmann 2 ) have already pointed out that during the production 

 on a small scale, the heavier portions easily remain in the resin, 

 and that only the lighter oil passes over. Lewinsohn has con- 

 firmed this fact again by his work. The constituents of myrrh oil 

 identified by him are: cuminic aldehyde, C 10 H 12 O (up to i°/ ), 

 b. p. 1 1 6° (12 mm. pressure); oxime, m. p. 5 6°; semicarbazone, m. p. 20 1°. 

 Oxidation with permanganate yielded cuminic acid, C 10 H 12 O 2 , m. p. 1 14 

 to 1 1 5 . — Acids: Of these, only acetic acid and palmitic acid 

 (m. p. 6 2°) were detected with certainty. Both are present in old 

 oils in the free state, whilst freshly distilled myrrh oil contains the 

 acids as esters. — Phenols (about i°/ ): In all 4 oils, eugenol (about 

 0,23 °/ ; benzoyl compound, m. p. 69 ), and a small quantity m-cresol 

 were detected. — Hydrocarbons: Fractional distillation over sodium 

 yielded four hydrocarbons (terpenes) of the formula C 10 H 16 (but not 

 simultaneously in all the examined oils), of which three were identified; 

 pin en e (nitrosochloride, m. p. 103 ; nitrolbenzylamine and nitrol- 

 piperidine); dipentene (tetrabromide, m. p. 124 °); limonene (tetra- 

 bromide, m. p. 104 ); the fourth hydrocarbon probably belongs also 

 to the limonene group (« D -J- 8o°, tetrabromide, m. p. 1 15 , and mono- 

 hydrochloride, m. p. 6°) but could not be identified. — Sesqui- 

 terpenes: From old oils a resin could be separated off by petroleum 

 ether which could be reduced to a hydrocarbon. The latter yielded 

 a crystallising addition product of hydrochloric acid (m. p. 115 to 11 7 ) 





*) Thesis, Berlin 1906; Arch, der Pharm. 244 (1906), 412. 

 2 ) Gildemeister and Hoffmann, The Volatile Oils, p. 487. 



