51-A.] 



MANNITOL 



105 



pallidus, L. pyrogallus, L. vellevreus, L. 

 turpis, L. piperatus, L. controversies, &c. 

 (Bourquelot, Comp. Rend. 108, 568) ; 

 Boletus and Amanita sp., Pholiota radi- 

 cosa, Hypholoma fasciculare (Ibid. Ill, 

 $>j8);Elaphomyces()ranulatus (Bissinger, 

 Arch. Pharm. [3] 21, 321); also in 

 ergotised rye (Pelouze and Liebig, 

 Comp. Rend. 3, 418; Ann. Chim. [3] 

 63, 113: for occurrence of mannitol in 

 algae, fungi, &c., see also Braconnot, 

 Ann. Chim. [i] 79,265; 80,272; 87, 

 237 ; Vauquelin, Ibid. 85, 5 ; Knop and 

 Schnedermann, Ann. 49, 293 ; Journ. 

 pr. Ch. 32, 411 ; Db'pping and Schloss- 

 berger, Ann. 52, 117; Miintz, Comp. 

 Rend. 76, 649; 79, 1182; 82, 210; 

 Ann. Chim. [5] 8, 56 ; Ferry, Ch. 

 Centr. 1889, 1, 541 ; 1891, 1, 220). 



The alcoholic extract of Affaricus 

 campestris contains mannitol (Zega, 

 Ch. Zeit. 24, 285). 



The mould Penicillium glavicum can 

 under certain conditions produce man- 

 nitol as a product of metabolism (Miintz; 

 see Klocker's ' Garungsorganismen, &c.' 

 p. 229). 



Mannitol is formed during the lactic 

 fermentation of sugar (Liebig, Jahres- 

 ber. 1847-48, 466 ; Strecker, Ann. 92, 

 80 ; Pasteur, Jahresber. 1857, 511; 

 Dragendorff, Ibid. 1879, 854 ; Arch. 

 Pharm. [3] 15, 47), and also during 

 the viscous or mucous fermentation of 

 sugar (Pasteur, Jahresber. 1861, 728 ; 

 Bull. Soc. 1861, 30; Journ. Pharm. [3] 

 39, 433). The sugar in wine is con- 

 verted into mannitol during the de- 

 generation known as ' bittering ' 

 (Basile, Staz. Sper. Agrar. 26, 451 ; 

 Gayon and Dubourg, Ann. Inst. Past. 

 8, 1894; Laborde, Comp. Rend. 126, 

 1223). This mannitol fermentation is 

 an anaerobic process (Peglion, Centr. 

 Bakter. II, 4, 73) and the ferment 

 can produce mannitol from Isevulose 

 only (Gayon and Dubourg, loc. cit. 15, 



Reducing micro- organisms generally 

 may give rise to mannitol during the 

 fermentation of sugars, especially under 

 anaerobic conditions. Thus, many fer- 

 mented liquors from various fruits, &c., 

 may contain mannitol (Vauquelin and 

 Fourcroy, Ann. Chim. [i] 65, 161 ; 



Pelouze, Ibid. [2] 47, 409 ; Berthelot, 

 Comp. Rend. 41, 392 ; Ann. Chim. [3] 

 46, 66; Scheibler, Ber. 6, 612; Gui- 

 bourt, Ann. Chim. [2] 16, 371 ; Mar- 

 cano, Comp. Rend. 1O8, 955 ; Carles, 

 Ibid. 112, 811 ; Blarez, Journ. Pharm. 

 [5] 27, 260; Roos, Ch. Centr. 1893, 

 1, 1098 ; Malbot, Bull. Soc. [3] 11, 87 ; 

 176; 413; Jandrier, Comp. Rend. 117, 

 498). 



Mannitol has been found in beet- 

 sugar molasses (Margueritte ; quoted by 

 Maquenne, ' Les Sucres, &c.' p. 131 : also 

 Scheibler, Ibid.; and v. Lippmann, Ber. 

 25, 3216). The mannitol is produced 

 in this case from sugar by Leuconostoc 

 mesenterioides (Greig-Smith and Steel, 

 Journ. Soc. Ch. Ind. 21, 1386). Ba- 

 cillus gummosus produces mannitol from 

 sugar (Happ ; quoted by Emmerling, 

 ' Die Zersetzung, &c.' p. 91). 



Mannitol has been found in the urine 

 of dogs after giving morphia or after 

 feeding with rye bread (Jaffe, Zeit. 

 physiol. Ch. 7, 297). The mannitol in 

 the last case may have been derived 

 directly from the bread. 



SYNTHETICAL PROCESSES. 



[A.] Formic aldehyde [91] in contact 

 with lime water or a mixture of mag- 

 nesia, magnesium sulphate, and lead 

 gives a syrupy mixture containing a- 

 acrose = i-fructose (Loew, Journ. pr. 

 Ch. [2] 33, 321, 34, 51; Fischer, Ber. 

 21, 989; Fischer and Passmore, Ber. 

 22 > 359 '> Loew, ibid. 475 : see also 

 Butleroff, Ann. 120, 295 ; Tollens, Ber. 

 15, 1639; 16, 1917; Wehmer and 

 Tollens, Ber. 19, 707 and 2135). On 

 treatment with phenylhydrazine the 

 a-acrosazone is obtained (Fischer), and 

 this by the action of strong hydrochloric 

 acid furnishes the corresponding a-acros- 

 one (Fischer and Tafel, Ber. 22, 98). 

 The latter by reduction with zinc dust 

 and acetic acid gives i-fructose which, 

 by reduction with sodium amalgam, is 

 converted into i-mannitol = a-acritol 

 (Fischer and Tafel, Ber. 22, 100) ; the 

 i-mannitol by oxidation with dilute 

 nitric acid gives i-mannose (Fischer, 

 Ber. 23, 390), and by further oxidation 

 with bromine i-mannonic acid. The 



