CHEMICAL CONSTITUTION AND SYNTHESIS 



References to Section i 



1. E. Wildiers, La Cellule, 1901, 18, 313. 



2. E. V. Eastcott, /. Phys. Chem., 1928, 32, 1094. 



3. D. Scherer, Annalen, 1850, 73, 322. 



4. L. Maquenne, Ann. Chim., 1887, 12, 80. 



5. H. Wieland and R. S. Wishart, Ber., 1914, 47, 2082. 



6. D. W. Woolley, Science, 1940, 92, 384 ; /. Biol. Chem., 1940, 136, 



113. 



3. ISOLATION OF INOSITOL 



D. W. Woolley ^ isolated inositol from the 70 % alcohol-insoluble 

 fraction of an aqueous liver extract hydrolysed with concentrated 

 hydrochloric acid. Impurities were removed by means of normal 

 lead acetate solution and the inositol was then precipitated with basic 

 lead acetate solution. After decomposing the precipitate with sul- 

 phuric acid, the inositol was precipitated by baryta in alcoholic solu- 

 tion and the precipitate decomposed with carbon dioxide. The 

 inositol was dissolved in the minimum amiount of water, and alcohol 

 was added to the solution until crystallisation occurred. 



Reference to Section 2 

 I. D. W. Woolley, /. Biol. Chem., 1941, 139, 29. 



3. CHEMICAL CONSTITUTION AND SYNTHESIS OF 



INOSITOL 



Inositol was shown to be a cyclic hexahydroxy-alcohol as long ago 

 as 1887,^ but its configuration was not established with certainty until 

 1942. One of the reasons for the slow progress in the elucidation of its 

 structure was that reactions found to be of value in determining the 

 structure of the sugars proved to be non-specific when applied to the 

 cyclic alcohols. 



The structure of w^so-inositol was established by degradation of 

 partly phosphorylated inositols by oxidation with potassium per- 

 manganate and the identification of the oxidation products. There 

 are eight possible configurations of hexahydroxycyclohexane. By the 

 action of phosphatase on phytin, an optically active tetraphosphoric 

 ester ^ and an optically inactive monophosphoric ester of meso- 

 inositol were obtained.^ The formation of the former proved that 

 w^so-inositol could not have all its hydroxyl groups on one side of the 



565 



