52-54.] 



SORBITOL 



107 



Sorbitol is converted into sorbose, 

 the hexose (ketose) from mountain- ash 

 berries, by the action of a Bacterium 

 (Bertrand, Comp. Rend. 122, 900; 

 126, 653). The sorbose Bacterium of 

 Bertrand is, as suspected by this author, 

 J3. xylinum of A. J. Brown (Emmerling, 

 Ber. 32, 541). 



SYNTHETICAL PROCESSES. 



[A.] From dextrose [154] by reduction 

 with sodium amalgam (Meunier, Comp. 

 Rend. Ill, 49). Mannitol is formed to 

 some extent [51 ; D]. 



[B.] From Itevulose [155] by reduc- 

 tion with sodium amalgam (Fischer, 

 Ber. 23, 3684 : see also under manni- 

 tol [51; E]). 



[C.] Mannose [156] with phenyl- 

 hydrazine in excess gives glucosazone 

 (Fischer, Ber. 20, 821 ; Fischer and 

 Hirschberger, Ber. 21, 1805; 22, 365; 

 1155; Reiss, Ibid. 609), and this on 

 heating with fuming hydrochloric acid 

 yields the osone (Fischer, Ber. 21, 2631 ; 

 22, 88; 23, 2120). The latter on 

 reduction with zinc and acetic acid 

 gives Itevulose [155] (Fischer, Ber. 23, 

 2121), which can be reduced to sorbitol 

 as above under B. 



53. Maniioheptol ; Perse'itol ; 

 Heptaneheptol. 



H H HO HO 



I I I I 

 HO . H.C . CH(OH)-C C-C-C CH 2 . OH 



I I I I 

 HOHOH H 

 or 



II H HO HO 



HO . H 2 C . C-C C-C-CH(OH) . CH 2 . OH 



I I I I 

 HOHOH H 



(Dextro-modification). 



NATURAL SOURCE. 



In fruit, seeds, and leaves of Laurus 

 persea (Avequin, 1831 ; Melsens, Ann. 

 Chim. [2] 72, 109 ; Miintz and Mar- 

 can o, Comp. Rend. 99, 38 ; Ann. Chim. 

 [6] 3, 279; Maquenne, Comp. Rend. 

 107, 583 ; Ann. Chim. [6] 19, 5). 



SYNTHETICAL PROCESS. 



or 



[A.] From formic aldehyde [9l] 

 glycerol [48] through d-mannose as 

 under mannitol [51 ; A]. The d-man- 

 nose forms a cyanhydrin by the action 

 of hydrogen cyanide [172], which hydro- 

 lyses to d-mannoheptonic acid (Fischer 

 and Hirschberger, Ber. 22, 370; Fischer 

 and Passmore, Ber. 23, 2226). The 

 anhydride (lactone) of this acid reduces 

 to d-mannoheptol by the action of 

 sodium amalgam (Fischer, Ber. 23, 

 936 ; Fischer and Passmore, ibid. 2231). 



AROMATIC ALCOHOLS AND PHENOLS. 



54. Benzyl Alcohol ; 

 Plieiiylcarbiiiol ; Pkenemetliylol. 

 CH, . OH 



NATURAL SOURCES. 



Occurs as benzoate in Peru balsam 

 from Myroxylon (Toluifera) pereirte, San 

 Salvador ; as cinnamic ester in this 

 balsam and in liquid storax from 



Liquidambar orientals. As benzoate 



and cinnamate in tolu balsam from 

 Myroxylon toluiferiim, New Granada, 

 Venezuela, Brazil, and Ecuador (Schar- 

 ling, Ann. 97, 168 ; Kraut, Ann. 107, 

 208; 109, 255; 152, 129; Strecker, 

 Jahresber. 1868, 566 ; Laubenheimer, 

 Ann. 164, 289; Busse, Ber. 9, 830; 

 Erdmann, Pharm. Journ. 65, 387 ; 

 Journ. Soc. Ch. Ind. 19, 1140). 



The alcohol is said to occur in small 

 quantity in the free state in Peru bal- 

 sam (Kraut, Ann. 152, 129: compare 

 Thorns, Arch. Pharm. 237, 271). Ben- 

 zyl alcohol has been found in the 

 volatile oil of the cherry laurel, Prunus 



