Commercial notes and scientific information. 107 



the bicyclic doubly unsaturated hydrocarbon. They probably belong to the vetivenols 

 C15H24O, just as the santalenes belong to the santalols, and should be differentiated 

 as bi- and tricyclic vetivene. 



The examination of Reunion vetiver oil (d 20 o 0,9916 and 0,9982; « D 24° 6' and 

 -j- 31°; n D 1,52429 and 1,52517) gave somewhat different results. The high-boiling 

 constituent vetivenolic vetivenate, is either absent from this compound, or only occurs 

 in it in scarcely detectable traces. The Reunion oil, like that distilled by us, contains 

 tricyclic and bicyclic vetivene. The tricyclic as well as the bicyclic vetivenol also 

 occur in the Reunion oil. 



In the course of reaction with phosphorus pentachloride in light petroleum solution, 

 the vetivenol from Reunion oil (b. p. 161 to 164° at 9 mm.) formed a chloride with 

 b. p. 140 to 147° (10 mm.): d 20O 0,9679, « D — 24°, n D 1,52640, from which latter a synthetic 

 vetivene was obtained by reduction with sodium and alcohol: b. p. 121 to 127° (9 mm.), 

 d 20O 0,9296, « D — 25° 48', n D 1,51491, mol. refr. found 66,1, calc. for C 15 H 24 ^ 66,07. 

 Semmler obtained a different result when, without previous distillation in vacuo, he 

 reduced the chloride (which had also been prepared by means of phosphorus penta- 

 chloride), with sodium and alcohol. The resulting hydrocarbon was first distilled ove 

 sodium and then subjected to a prolonged shaking with a 3 p. c. permanganate solution; 

 after which it possessed the following characteristics: b. p. 123 to 129° (10 mm.), 

 d 20O 0,9288, « D + 6°12', n D 1,50682, mol. refr. found 63,88, calc. for Ci 5 H 24 r 64,45. 

 Further investigation is needed to clear up the point in how far the synthetic and the 

 natural vetivenes are identical. 



Reduction of the crude vetivenol from Reunion oil by means of hydrogen in the 

 presence of finely divided platinum led apparently to tricyclic dihydrovetivenol and 

 bicyclic tetrahydrovetivenol. A small portion of the vetivenol was reduced to a hydro- 

 carbon in the process. 



Oil of Wallflower seed. It will be remembered that wallflower seed contains the 

 isosulphocyanate cheiroline in glucoside-like combination, and that W. Schneider 1 ) 

 has identified this body as a /-thiocarbimidopropylmethylsulphone. Schneider, in 

 collaboration with Lohmann 2 ), has recently reported on the glucoside, which is obtai- 

 nable from the seeds (after removal of their fatty constituents) by extraction with 

 anhydrous alcohol. The glucoside occurs as a substance without definite melting-point, 

 and exceptionally readily soluble in water. When separated out from its alcoholic 

 solution it still contains from 6 to 7 p. c. alcohol of crystallisation (?) which, however, 

 it gives off in vacuo over sodium at water-bath temperature. It was unfortunately 

 impossible to prepare the glucoside in the pure state, its conditions of solubility 

 being exceedingly unmanageable. Chemically it shows close analogy to other gluco- 

 sides of mustard oil, and among its constituents are cheirolin, glucose, sulphuric 

 acid, and potassium. Sulphur occurs in the glucoside-molecule in three modifications: 

 as sulphuric acid, as allyl sulphide and as sulphonic sulphide. Cheiroline may be 

 isolated by enzymatic decomposition with the myrosine of white mustard. The wall- 

 flower seed itself contains an enzyme which has the power of decomposing the sinigrine 

 of black mustard (mustard oil being formed during the reaction), and which is therefore 

 equal in value to, if not identical with, myrosine. 



In searching for the presence of other sulphone mustard oils in the N. O. of the 

 Cruciferce, the authors succeeded in proving the presence of allyl /^osulphocyanate and 



l ) Litbigs Annalen 375 (1910), 207; Report October 1910, 85. — -) Eerl. EerichU 45 (1912), 2954. 



