52 Report of Schimmel sj Co. April 1913. 



second, liquid, sesquiterpene alcohol. This alcohol boils between 136 and 138° 

 (4 to 5 mm.) that is to say at a considerable higher degree than does cypress- 

 camphor, which was the principal body found in the fractions with b. p. 123 to 125° 

 (4 mm.). When warmed with strong formic acid, the alcohol is converted into a 

 hydrocarbon, water being eliminated. Combustion confirmed the body to be an 

 alcohol with the formula d 5 H 26 0. 



0,1759 gr. Sbst: 0,5247 gr. C0 2 , 0,1842 gr. H 2 0. 

 Calc. for Ci 5 H 26 Found 



C 81,82% 81,35% 



H 11,71% 11,64%. 



So far we have been unable to identify it from any derivatives. 



Oil of Erysimum Perofskianum. A homologue of the sulphone mustard oil 

 cheirolin 1 ) which can be isolated from wallflower seed, has been obtained from the 

 seed of Erysimum Perofskianum, Fisch. et Mey. (M O. Cruciferce), by W. Schneider, 

 working in collaboration with H. Kaufmann -). Its empirical formula is C 6 Hii0 2 NS 2 (that 

 of cheirolin being C 5 H 9 2 NS 2 ), and it is called erysolin from its origin. The yield from 

 1 kilo of green seed, containing fatty constituents, was at most 0,5 gram. (= 0,05 p. c). 

 Recrystallised from ether, erysolin forms beautiful, colourless prisms (m. p. 59 to 60°) 

 which strongly excite the mucous membrane. With alcoholic ammonia it yields a 

 sulpho-urea, melting between 143 and 144°. Saponification with hydrochloric acid led 

 to the base of erysolin from which, by oxidation with nitric acid, ^-aminobutyl-methyl- 

 sulphone was obtained. Owing to the scarcity of available material it was impossible 

 to carry the resolution further. It was, however, found possible to prepare erysolin 

 synthetically. With this object in view, chlorobutyronitrile was allowed to react with 

 the calculated quantity of sodium mercaptide, when y-methylsulphide butyronitrile, 

 CH 3 S(CH 2 ) 3 CN was formed. The latter, when reduced with sodium and alcohol 

 yielded ^-aminobutyl methylsulphide CH 3 S(CH 2 ) 4 NH 2 , of which , the dilute aqueous 

 solution has an odour reminding of that of crab or lobster. When oxidised in acetone 

 solution with hydrogen peroxide this sulphide yields <?-aminobutyl methyl sulphoxide 

 (CH 3 -SO-(CH 2 ) 4 NH 2 ), from which, upon oxidation with potassium permanganate in 

 acid solution, <)-aminobutyl methylsulphone (CH 3 -S0 2 -(CH 2 )4'NH S ) resulted. The latter, 

 in alcoholic solution with carbon disulphide, was converted into the dithiocarbami- 

 nate (I) 3 ) which, in its turn, was oxidised with iodine into the corresponding dithiurame 



CrVS0 2 -(CH 2 )4-NH x 



CH 3 S0 2 (CH 2 ) 4 -NHv 



C : S + h 



CrVSOo-(CH 2 )4-NH 2 -Hs/ 



SC:S 

 SC:S 

 CH8-S0 2 (CH 2 ) 4 vNh/ 



I (Dithiocarbaminate). II (Dithiurame disulphide). 



CH 3 -S0 2 (CH 2 ) 4 -Mx 



S-C-SNa 

 S-C-SNa 

 CH 3 • S0 2 • (CH 2 ) 4 • N ^ CH 3 • S0 2 • (CH 2 ) 4 • NCS 



III (Na-salt of dithiurame disulphide). IV (^-Thiocarbimidobutyl-methylsulphone). 



x ) Comp. Report October 1910, 85. — 2 ) Uebigs Annalen 392 (1912), 1. — 3 ) By J. v. Braun's method, 

 Berl. Berichte 45 (1912), 2188; h'eport October 1912, 164. 



