Synthesis and chemical carcinogen inhibitory activity of 2-tert-butyl-4-hydroxyanisole
- 1 May 1979
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of Medicinal Chemistry
- Vol. 22 (5) , 569-571
- https://doi.org/10.1021/jm00191a020
Abstract
The title compound 1 was selectively synthesized in its pure isomeric form by means of the hydroxyl-protecting reagent dimethyl-tert-butylchlorosilane. Exclusive silylation occurred at the less hindered hydroxyl group of 3. Dimethyl sulfate methylation of 4 gave 5 in excellent yield. Compound 1 was then obtained by acid hydrolysis of 5. Two BHA [butylated hydroxyanisole] isomers, were tested on their inhibitory effects toward benzo[a]pyrene-induced neoplasia in the forestomach of the ICR/Ha mouse. Both isomers, when added to the diet, reduced the number of mice with tumors and the number of tumors per mouse. Isomer 1, which has the less hindered free hydroxyl group, showed higher inhibitory effect in the present experimental model.This publication has 2 references indexed in Scilit:
- Effects of Butylated Hydroxyanisole on the Metabolism of Benzo[a]pyrene by Mouse Liver Microsomes2JNCI Journal of the National Cancer Institute, 1977
- Determination of isomer content of butylated hydroxyanisoleJournal of Agricultural and Food Chemistry, 1967