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Do you have any information on Butylated Hydroxytoluene that you are willing to share for my school project? --Thanx
Question Date: 2011-03-10
Answer 1:

Butylated hydroxytoluene (IUPAC name2,6-bis(1,1-dimethylethyl)-4-methylphenol) is used as an antioxidantand preservative in food. It is similar in structure to vitamin E,which is a naturally occurring antioxidant (also called a reducingagent) in cells that protects lipids from oxidation.

Butylated hydroxytoluene (BHT) protects against radicals and the propagation of destructive reactions caused by radicals. A radical is a chemical species with an unpaired electron. Since species withunpaired electrons are unstable, they also tend to be very reactive.This reactivity can be dangerous to biological systems as well as food.

When a radical attacks a lipid (or other molecules), it transfers the lone electron. The lipid then becomes a radical that can react with itself or other molecules in a destructive chain reaction. BHT is able to inhibit the propagation of the radical reaction.

When the hydrogen is removed from the phenol in the BHT, the remaining phenoxide ion becomes a good electron donor. The phenoxide can donate an electron to a radical species, which ends the propagation of radical reactions. The BHT is then itself a radical, but it is much less reactive than most radical species because the lone electron is stabilized by the conjugation in the phenyl ring and the sterichindrance from the two butyl groups further impedes the possibility of a reaction.

I have attached structures of BHT showing how the name corresponds to different parts of the structure for both the common name and theIUPAC name.



References:Structures from

Vollhardt, K. Peter C., and Neil Eric Schore. "Chapter 22: Chemistryof Benzene Substituents." Organic Chemistry: Structure and Function.New York: W.H. Freeman and, 2003. 134-37. Print.

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