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22-AUGUST-2008 06:13:22 - Butylated hydroxytoluene July 2008 Butylated hydroxytoluene Butylated hydroxytoluene IUPAC name 2,6-bis1,1-dimethylethyl-4-methylphenol Other names 2,6-di-tert-butyl-4-methylphenol; 2,6-di-tert-butyl-p-cresol DBPC; butylated hydroxytoluene; BHT Identifiers CAS number 128-37-0 EINECS number 204-881-4 RTECS number GO7875000 Properties Molecular formula C15H24O Molar mass 220.35 g/mol Appearance white powder Density 1.048 g/cm³, solid Melting point 70-73 °C Boiling point 265 °C 538.15 K Solubility in water insol. Hazards MSDS External MSDS Main hazards Flammable R-phrases 22-36 37 38 S-phrases 26-36 Flash point 127 °C Related compounds Related compounds butylated hydroxyanisole Except where noted otherwise, data are given for materials in their standard state at 25 °C, 100 kPa Infobox references Butylated hydroxytoluene BHT, also known as Butylhydroxytoluene, is a lipophilic fat-soluble organic compound that is primarily used as an antioxidant food additive E number E321 as well as in cosmetics, pharmaceuticals, jet fuels, rubber, petroleum products, and embalming fluid. Contents 1 Chemistry 2 Controversy 3 References 4 See also 5 External links Chemistry BHT is produced by alkylation reaction of p-cresol with isobutylene. The species behaves as a synthetic analogue of vitamin E, primarily acting as a terminating agent that suppresses autoxidation, a process whereby unsaturated usually organic compounds are attacked by atmospheric oxygen. BHT stops this autocatalytic reaction by converting peroxy radicals to hydroperoxides. It effects this function by donating a hydrogen atom: RO2. + ArOH → ROOH + ArO. RO2. + ArO. → nonradical products where R is alkyl or aryl, and where ArOH is BHT or related phenolic antioxidants. One can see that each BHT consumes two peroxy radicals.1 In the chemical industry it is added to tetrahydrofuran and diethyl ether in order to inhibit the formation of dangerous organic peroxides. Controversy This article or section may be inaccurate or unbalanced in favor of certain viewpoints. Please improve the article by adding information on neglected viewpoints, or discuss the issue on the talk page. Concerns have been raised about the use of BHT in food products.citation needed The compound has been banned for use in food in Japan 1958, Romania, Sweden, and Australia. The US has barred it from infant foods.citation needed Some food industries have voluntarily eliminated it from their products. However, BHT is also marketed as a health food supplement in capsule form. In different studies, BHT has been reported to cure some cancers, but to encourage others.citation needed BHT is well studied because of public concern over synthetic preservatives. Since the 1970s, BHT has been steadily replaced with the less studied BHA. References ^ Burton, G. W.; Ingold, K. U., Autoxidation of biological molecules. 1. Antioxidant activity of vitamin E and related chain-breaking phenolic antioxidants in vitro, Journal of the American Chemical Society, 1981, volume 103, pp 6472 - 6477. DOI: 10.1021/ja00411a035 See also Butylated hydroxyanisole BHA External links An experiment on the effectiveness BHT has against herpes cold sore outbreaks Why are BHA and BHT in foods? Are they safe? Bioassay of BHT, includes structure BUTYLATED HYDROXYTOLUENE ICSC Butylated Hydroxytoluene BHT Antioxidant Retrieved from http://en..org/wiki/Butylated_hydroxytoluene Categories: Antioxidants | Phenols | Fuel antioxidants | Food antioxidantsHidden categories: Articles lacking sources from July 2008 | All articles lacking sources | Articles needing more viewpoints | All articles with statements | Articles with statements since September 2007 | Articles with statements since April 2008 Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages Deutsch Español Français Italiano Magyar Nederlands 日本語 Polski Português РуÑ?Ñ?кий ä¸æ–‡ This page was last modified on 12 August 2008, at 20:45. of the GNU Free Documentation License. ® , Inc., a U.S.
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