CHEMICAL STRUCTURE AND BIOLOGICAL ACTIVITY 



827 



of esters and ethers of trimethylhydroquinone is given in Table 9, while the 

 corresponding data on the derivatives of tetramethylhydroquinone are 

 summarized in Table 10. 



TABLE 9 

 Vitamin E Activity of Ethers and Esters of Trimethylhydroquinone" 



Active compounds 



Inactive compounds 



Monobenzoate* 

 Mono-n-hexyl ether'' 

 Mono-re-dodecyl ether* . 

 Mono-n-dodecyl ether acetate'^ 

 Monodihydrochaulmoogryl other" 



Bis-jS-iodopropionate'' 

 Di-n-dodecyl ether* 



» Adapted from L. I. Smith, Chem. Revs., 27, 287-329 (1940). 



^ F. V. Werder, T. Moll, and F. Jung, Z. phtjsiol. Chem., 257, 129-139 (1939). 



« F. V. Werder and T. Moll, Z. physiol. Chem., 254, 39-50 (1938). 



TABLE 10 

 ViTAMm E Activity of P]thers and Esters of Tetramethylhydroquinone" 



Active compounds 



Inactive compounds 



Mono-n-butyl ether** 

 Di-n-butyl ether' 

 Mono-n-hexyl ether' 

 Di-n-hexyl ether* 

 Mono-n-octyl ether' 

 Di-n-octyl ether' 

 Monocetyl ether* 

 Mono-n-dodecyl ether palmitate' 

 Monodecyl ether'-* 

 Mono-n-nonadecyl 2-ether* 

 Mono-ra-nonadecyl ether** 



Monodihydrochaulmoogryl ether' 



Monobenzyl ether' 



Mono-n-heptyl ether* 

 Dibenzyl ether' 



Monocetyl ether* 



Mono-w-dodecyl ether n-propionate' 

 Di-n-dodecy] ether' 

 Mono-n-octadecyl ether*^ 

 Mono-2-methyloctadecyl ether* 

 Di-7i-nonadecyl ether** 

 Mono-3-methyl-5-( 1', 1 ',3'-trimethyl- 

 2'-cyclohexyl)pentyl-l ether"* 



" Adapted from L. I. Smith, Chem. Revs., 27, 287-329 (1940). 



* F. V. Werder and T. Moll, Z. physiol. Chem., 254, 39-50 (1938). 



« H, M. Evans, G. A. Emerson, and O. H. Emerson, Science, 88, 38-39 (1938). 



<* F. V. Werder, T. Moll, and F. Jung, Z. physiol. Chem., 257, 129-139 (1939). 



Phytol, Avhen fed alone or in conjunction with trimethylhydroquinone"' 

 has been found to be inactive as a source of vitamin E. Although these 

 two components readily condense in the laboratory to form a-tocopherol in 

 excellent yield, a synthesis of this nature apparently does not take place in 



VIVO. 



