Studies on tocopherol derivatives: V. Intestinal absorption of several d,1-3,4-3H2-alpha-tocopheryl esters in the rat.

Abstract

Twelve d,1-3,4-3H2-alpha-tocopheryl esters were synthesized from d,1-3,4-3H2-alpha-tocopherol. They were acetate, propionate, butyrate, isobutyrate, caprylate, palmitate, acid succinate, benzoate, nicotinate, o-hydroxybenzoate, o-acetoxybenzoate, and pivalate. The hydrolysis of these esters with bile-pancreatic juice and with 9,000 x g supernatant of small intestine and liver homogenates of rats was examined. When these esters were incubated in small intestine or liver supernatants, hydrolysis occurred at a similar rate. In the incubation experiments, alpha-tocopheryl acetate, propionate, butyrate, isobutyrate, caprylate, palmitate, and acid succinate were classified as an easily hydrolyzable group. Alpha-tocopheryl benzoate and nicotinate were in a moderately hydrolyzable group. O-hydroxybenzoate and pivalate, which resisted hydrolysis, were in a scarcely hydrolyzable group. O-acetoxybenzoate was easily hydrolyzed to the o-hydroxybenzoate. Hydrolysis on straight chain fatty acid esters of alpha-tocopherol easily occurred in bile-pancreatic juice. In in vivo experiments, the lymphatic absorption rate of 6 esters, acetate, palmitate, acid succinate, nicotinate, o-hydroxybenzoate, and pivalate, was measured on thoracic duct fistula rats. Easily hydrolyzable esters were recovered mostly in lymph as alpha-tocopherol, whereas, an ester which strongly resisted hydrolysis, such as pivalate, appeared mainly unchanged. This fact suggested that hydrolysis of alpha-tocopheryl esters was not necessarily a prerequisite for intestinal absorption. The percentage of absorption of slowly hydrolyzed esters in lymph was relatively lower than that of moderately or easily hydrolyzable esters.