242 



CARBOHYDRATES AND GLUCOSIDES [151-152 A. 



CARBOHYDRATES AND GLUCOSIDES. 



151. Diliyclroxy acetone ; 

 Pr op an ediol o 11 e . 



HO.CH 2 .CO.CH 2 .OH 



NATURAL SOURCES. 



A product of fermentation of glycerol 

 by the sorbose bacterium (Bertrand, 

 Comp. Rend. 126, 843 ; 984 ; Bull. 

 Soc. [3] 19, 502 ; Bertrand and Sazerac, 

 Comp. Rend. 132, 1504). According 

 to Emmerling (Ber. 32, 541) the sor- 

 bose bacterium is Bacterium xylinum of 

 A. J. Brown (Trans. Ch. Soc. 49, 432). 

 Other micro-organisms are capable of 

 acting upon glycerol in a similar way 

 (Bertrand, Comp. Rend. 133, 887). 



Glucose appears to give dihydroxy- 

 acetone among the products of its fer- 

 mentaiionby Bacillus roseus #iw(Bordas, 

 Joulin, and Raczkowski, Comp. Rend. 

 126, 1050), and the same Bacillus pro- 

 duces the dihydroxyketone from glycerol 

 ([bid. 1443). 



SYNTHETICAL PROCESSES. 



[A.] ~Fromformic aldehyde [9l] and 

 methyl alcohol [13] through nitroiso- 

 butylglycerol and dihydroxyacetone- 

 oxime (see under glycerol [48 ; L]). 



[B.] From citric acid [Vol. II] through 

 acetonedicarboxylic acid and diamino- 

 acetone [48; M]. 



[C.] From hippuric acid [Vol. II] 

 through diaminoacetone [48 ; N]. 



[D.] Glycerol [48] gives ' glycerose ' 

 on oxidation with nitric acid or by 

 electrolysis (Van Deen, Jahresber. 1863, 

 501 ; Stone, Am. Ch. Journ. 15, 656 ; 

 Fischer and Tafel, Ber. 20, 1088), by 

 oxidation with platinum black (Gri- 

 maux, Comp. Rend. 1O4, 1276; Bull. 

 Soc. [2] 45, 481 ; 49, 251 ; Emmer- 

 ling, Ber. 32, 542), with sodium hypo- 

 bromite or bromine and lead glycerate 

 (Fischer and Tafel, loc. cit. 3384 ; 

 21, 2634; 22, 106), or with hydrogen 

 peroxide in presence of ferrous sulphate 



(Fenton and Jackson, Trans. Ch. Soc. 

 75, 5). Glycerol gives glycerose on 

 oxidation by quinone in the presence of 

 light (Ciamician and Silber, Ber. 34, 



1532). 



Glycerose is a mixture of dihydroxy- 

 acetone with glyceric aldehyde, the 

 former predominating (Fischer and 

 Tafel, Ber. 20, 3384; see also Pilot y, 

 Ber. 3O, 3162; Wohl and Neuberg, Ber. 

 33, 3099). 



152. d-Erytlvmlose ; 

 Butanetriolone. 



HO 



I 

 HO . H 2 C . C . CO . CH 2 . OH 



1, 



NATURAL SOURCE. 



A product of fermentation of ery- 

 thritol by the sorbose bacterium (Ber- 

 trand, Comp. Rend. 126, 762 ; 130, 

 1330; 1472; Bull. Soc. [3] 19, 347; 

 23, 681). 



SYNTHETICAL PROCESSES. 



[A.] From erythritol [50] by oxida- 

 tion with nitric acid (Fischer and Tafel, 

 Ber. 20, 1088), with platinum black 

 (Grimaux, Comp. Rend. 104, 1276; 

 Bull. Soc. [2] 45, 481; 49, 251), or 

 with hydrogen peroxide and ferrous 

 sulphate (Fenton and Jackson, Trans. 

 Ch. Soc. 75, 7; Neuberg, Ber. 35, 

 2627). 



NOTE : The synthetical product is i-erythru- 

 lose. The ketose character of the synthetical 

 sugar, and therefore its identity with the bio- 

 chemical sugar, has only been proved (apart 

 from optical properties) in the case of the pro- 

 duct obtained by the last method, viz. hydrogen 

 peroxide and ferrous sulphate (Neuberg, loc. cit.'). 

 Other synthetical tetroses (probably aldoses) 

 have been obtained, but not from biochemical 

 sources. In order to complete the history of 

 these compounds the synthetical processes are 

 given below. 



