Fate of ¹⁴C-Butylated Hydroxyanisole in Oil

Abstract

[¹⁴C]2-tert-Butyl-4-methoxyphenol (¹⁴C-BHA) was synthesized from [¹⁴C]phenol. ¹⁴C-BHA was added to methyl oleate in various states of autoxidation, and the mixture was irradiated with ultraviolet rays or heated under aeration. The amounts of residual ¹⁴C-BHA, oxidation products of BHA (diphenyl and diphenyl ether compounds) and products formed by the interaction of oxidized methyl oleate and ¹⁴C-BHA were followed by the tracer method.
From a consideration of these data, it we conclude that most of the ¹⁴C-BHA is consumed by the formation of addition products to peroxidized oil, and a part of the ¹⁴C-BHA is consumed to form oxidation products. The main addition product, which had hydroperoxy and trans C=C groups and radioactivity, was isolated by column chromatography. The formation of addition products increased remarkably on addition of BHA to oxidized methyl oleate, compared with nonoxidized methyl oleate.