Notes on scientific research. 151 



b. p. 208° (25 mm.), dj~ 1,0619. Geraniol dioxide, in the presence of traces of an acid, 

 yields a mixture of two compounds, one a crystalline product, Ci H 17 O(OH) 3 -2H 2 O, 

 m. p. 94,5 to 95,5°, and the other a liquid portion. The crystalline product, after being 

 dried, was split up into two compounds by recrystallisation from glacial acetic ester 

 under exclusion of moisture, viz. 1. A compound Ci Hi 7 O(OH).j, m. p. 145 to 146° and 

 2. a compound of the same constitution but with m. p. 163 to 164°. The first-named 

 compound is a monohydrate of geraniol dioxide and with acetic anhydride forms an 

 ester C 10 H 17 (OCOCH 3 ) 3 : b. p. 189,5 to 190° (14 mm.), d^g 1,1253. The liquid portion 

 which is formed in the hydration of geraniol dioxide boils between 197 and 201° 

 (14 mm.), but it does not appear to be a uniform body. Prilechajeff now ascribes to 

 linalool monoxide somewhat different properties than those which he had enumerated 

 for it on a previous occasion. He gives b. p. 197 to 198° (758 mm.), d~ c c J 0,9520, 

 n D16 o 1,45567. The constants 1 ) determined by us at the time for preparations derived 

 from Mexican linaloe oil were as follow: b. p. 193 to 194°, 63 to 65° (4 mm), di 50 0,9431 

 to 0,9442, « D — 5°25' to — 5°46', n D20O 1,45191 to 1,45221. Prilechajeff attempted to 

 hydrate the linalool monoxide, but without success. When heating it with highly 

 dilute hydrochloric acid to 150° he obtained a product with an odour of camphor, 

 b. p. 120 to 122° (25 mm.), (djg 0,8576; n D1 ,o 1,5038; semicarbazone, m. p. 138,5°) which 

 rapidly becomes oxidised into a gum-like mass when exposed to air. Linalool monoxide 

 when treated with acetic anhydride yields a liquid with an odour of bergamot oil, 

 b. p. 118 to 119° (25 mm.): djg0,9770, n D16 o 1,44972. Prilechajeff gives the sp. rotation 

 of linalool dioxide as [«]d + 5,3°; n D16 o 1,46170. When hydrated it forms a glycerol 

 oxide which with acetic anhydride yields a compound CioHi 7 (OH)(OCOCH 3 ) 4 : b. p. 207 

 to 209° (20 mm.) d£g 1,114, n D16 o 1,4531. The oxide of linalyl acetate, Ci H 17 O 2 COCH 3 , 

 boils between 138 and 139° (25 mm.): d^0,9742, [«] D — 2,58°, n D16llo 1 ,44847. It absorbs 

 water energetically, giving rise to a compound Ci H 17 (OH) 2 (OCOCH 3 ), b. p. 171 to 175° 

 (20 mm.). After saponification of this ester there is formed a body C xo Hi 7 (OH) 3 : 

 m. p. 54 to 55°, b. p. 177 to 180° (15 mm.). On the present occasion Prilechajeff gives 

 the following data for citral monoxide: b. p. 144,5 to 145,5° (20 mm.), d^ 0,9679, 

 n D16 o 1,47848. The glycol which is formed when citral oxide is hydrated has dj|§ 1,0335. 

 Treatment with moist silver oxide gives rise to an acid C 9 Hi 4 (OH)COOH, b. p. 176 to 

 180° (19 mm.); with acetic anhydride the glycol forms a compound CioH 16 3 (COCH 3 )s, 

 b. p. 205 to 207° (15 mm.). When it was attempted to prepare citral dioxide, a 

 decomposing oxidation ensued and a carbon-atom was split off, giving rise to a body 

 C 9 H 16 2 , b. p. 114 to 115° (25 mm.), d^0,9419, n D16 o 1,43728. The hydrate of this body 

 boils between 161 and 162° (25 mm.), d~ 1,0573, n D16 o 1,4710. 



Nitrogenous bodies. 



Sinigrine. According to Gadamer's investigations' 2 ) the glucosides of mustard 

 oil are in all probability derived from a hypothetic alkyliminothiol carbonic acid, 

 possessing the general formula R-N : C(SH)(OH). Thus, in his opinion, sinigrine 

 possesses the structure (shown in formula I), of an allylimino thiol carbonic acid, of 

 which the hydroxyl is esterified with the residual acid (potassium bisulphate), while 

 the sulphohydryl occurs in an ether-like combination with glucose. 



As the formula of sinigrine is at present only of a hypothetical character, W. Schneider") 

 has undertaken to synthetise compounds of type I and to compare the chemical behaviour 



!) Report October 1912, 78. — 2 ) Arch, der Pharm. 235 (1897), 47; Berl Bericlite 30 (1897), 2322, 232S. 

 3 ) Berl. Berichte 45 (1912), 2961. 



