— 85 — 



only known that the oil is prepared from several species of origanum 

 growing in the Mediterranean countries 1 ). 



A parcel of flowering herb from Smyrna which was received by us 

 some time ago for distilling purposes therefore gave us a welcome 

 opportunity of causing the botanical origin of the material to be determined. 

 Dr. Giessler, Curator of the Botanical Institute at Leipzig, found the parent 

 plant of our parcel to be Majorana Onites, (L), Benth. {Origanum Onites, 

 L, Origanum smyrnceum. L). The oil, of which a yield of 2°/o was ob- 

 tained, was dark-brown and gave the following constants: d 15 o 0,9572, 

 a D — 1°30' or, from another sample: — 2° 10', phenol-content 74°/ , sol. 

 in 2,2 vols and more of 70% alcohol. It differed from the usual commercial 

 oils from Smyrna (which are also said to be derived from Origanum 

 smyrnceum) in having a much greater phenol content, and in its low 

 linalool content. This may perhaps be explained by the peculiar condition 

 of the raw material, for by far the greater part of the herb worked up 

 by us consisted of flowers, and it is of course possible that the oil 

 from the flowers may be much richer in phenols than that from the 

 other parts of the plant. But this is only a surmise, the correctness 

 of which must be determined by special experiments. More detailed 

 examination showed that the phenols consisted almost entirely of carvacrol. 

 At 754 mm. press, they boiled between 235 and 237°, at 5 mm. press, between 

 95 and 96°. The nitroso compound melted at 153°. In contradistinction 

 to what has been observed in the other oils from Smyrna 2 ), the non-phenols 

 of our distillate only had a faint linalool odour, and when subjected to 

 fractional distillation at 4 mm. press, they behaved as follows: — 



1. 



37 to 42° 



17°/o 



« D — 1°56' 



2. 



42 „ 45° 



25°/o 



+ 1°50' 



3. 



45 „ 72° 



1 1 °/o 



+ 1°30' 



4. 



72 „ 80° 



5°/o 



— 5° 40' 



5. 



80 „ 105° 



15°/o 



— 11°28' 



6. 



105 „ 120° 



7°/o 



— 25° 45' 



7. 



Residue 



20°/o 



— 



Fraction 1 consisted principally af «-pinene (benzyl nitrolamine, m. p. 

 123,5°) but the two following fractions consisted almost entirely of p-cymene, 

 which was identified by conversion into p-hydroxy?sopropyl benzoic acid, 

 m. p. 155°. 



The fourth fraction, after repeated fractionation, was found to contain 

 1-linalool. The phenylurethane, which was formed from phenyl isocyanate, 

 was lasvorotatory (as was the linalool fraction itself), its m. p. being 63 

 to 64°. Its m. p. was not depressed with a preparation from pure linalool 

 used for purposes of comparison. The fifth fraction was solid at ordinary 

 temperature owing to camphor having separated out. This camphor was 

 dextrorotatory and, after purification, gave m. p. 176 to 177°. Its oxime 



3 ) Comp. Gildemeister and Hoffmann, "The Volatile Oils", 1 th Ed., p. 622. 

 2 ) Report April 1895, 52. 



