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Oil ofUmbellularia californica. Fr.B.PowerandFr.H.Lees 1 ) 

 report on an detailed examination of the essential oil of the Californian 

 laurel Umbelhilaria californica Nuttall. This tree which is distributed 

 in the valleys of Oregon and California, contains in the leaves 

 an oil with a pungent odour causing the flow of tears, which had 

 already been examined earlier 2 ) by He any 3 ) and Stillman 4 ). The 

 latter observed that the body with the pungent odour is chiefly pre- 

 sent in the fractions boiling between 215 and 21 6°, and gave to the 

 compound the name umbellol. The analysis showed the com- 

 position C 8 H 12 0. 



The quantity of oil examined by Power and Lees amounted to 

 1200 kilo; d 16 o 0,9483; «d — 22°\ the oil was completely soluble in 

 1,5 parts 70 per cent, alcohol, did not react with bisulphite liquor, 

 and contained neither nitrogen nor sulphur compounds. Apart from 

 traces of formic acid and higher fatty acids, the oil contained 

 of compounds soluble in soda liquor only eugenol. Of the latter 

 1,7 °/ were obtained by shaking with liquor. The benzoyl com- 

 pound of eugenol produced melted at 69 to 70 . 



Of well-known bodies there were further detected in the oil boiling 

 from 150 to 250 , 1-pinene 6°/ , cineol 2O°/ , eugenol methyl 

 ether 10 °/ , and small quantities of safrol. Of special interest was 

 the fraction -2 17 to 2 2 2°, which represents 60 °/ of the oil, and 

 which contained the constituent with the pungent odour. This fraction 

 consists chiefly of a ketone C 10 H 14 O, which Stillman had before him 

 in the impure state. This ketone, on which F. H. Lees 5 ) gives further 

 information in a separate publication, is called by the authors umbell- 

 ulone. It does not react with bisulphite liquor, absorbs 2 atoms bromine, 

 and immediately discolours potassium permanganate solution. The con- 

 stants of the umbellulone fraction were as follows: boiling point 21 8°, 

 at 752 mm.; d^o 0,9614; «rj — 36°33 / . With semicarbazide it com- 

 bines to a compound C 10 H 15 (:N . NH . CO . NH 2 ) CH 4 ON 3 of the 

 melting point 217 , which is split up by boiling with dilute mineral acids, 

 with separation of umbellulone. The pure umbellulone thus obtained 

 distils from 219 to 220 at 749 mm. as a colourless oil which at first 

 has a pleasant mint -like odour, but on stronger smelling causes the 

 flow of tears. 



With hydroxylamine the compound C 10 H 15 (: N • OH) NH • OH 

 was obtained as a faint green amorphous mass. 



1 ) Journ. Chem. Soc. 85 (1904), 029. 



2 ) Report October 1887, 47. 



8 ) Americ. Journ. Pharm. 47 (1875), I0 5- — Pharmaceutical Journal III. 5 

 1*875), 791. 



4 ) Berl. Berichte 13 (1880), 630. 



5 ) Journ. chem. Soc. 85 (1904), 639. 



