Butylated hydroxytoluene
IUPAC name	2,6-bis(1,1-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
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 Image File history File links 2,6-bis(1,1-dimethylethyl)-4-methylphenol. ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... RTECS, also known as Registry of Toxic Effects of Chemical Substances, is a database of toxicity information compiled from the open scientific literature that is available for charge. ... A chemical formula is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... This article does not cite any references or sources. ... For other uses, see Density (disambiguation). ... The melting point of a crystalline solid is the temperature range at which it changes state from solid to liquid. ...
Boiling point	265 °C (538.15 K) Italic text This article is about the boiling point of liquids. ...
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 disclaimer and references

Butylated hydroxytoluene (BHT) is the organic compound with the formula MeC₆H₂(CMe₃)₂OH (Me = methyl). This lipophilic (fat-soluble) phenol 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. Solubility is a chemical property referring to the ability for a given substance, the solute, to dissolve in a solvent. ... Impact from a water drop causes an upward rebound jet surrounded by circular capillary waves. ... This page meets Wikipedias criteria for speedy deletion. ... The examples and perspective in this article or section may not represent a worldwide view. ... R-phrases are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous substances and preparations. ... S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. ... For other uses, see Flash point (disambiguation). ... Butylated hydroxyanisole (BHA) is a mixture of two isomeric organic compounds, 2-tert-butyl-4-hydroxyanisole and 3-tert-butyl-4-hydroxyanisole. ... In chemistry, the standard state of a material is its state at 1 bar (100 kilopascals) and 25 degrees Celsius (298. ... Benzene is the simplest of the arenes, a family of organic compounds An organic compound is any member of a large class of chemical compounds whose molecules contain carbon and hydrogen; therefore, carbides, carbonates, carbon oxides and elementary carbon are not organic (see below for more on the definition controversy... A chemical formula is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... In chemistry a methyl-group is a hydrophobic Alkyl functional group which is derived from methane (CH4). ... Phenol, also known under an older name of carbolic acid, is a colourless crystalline solid with a typical sweet tarry odor. ... Space-filling model of the antioxidant metabolite glutathione. ... Food additives are substances added to food to preserve flavor or improve its taste and appearance. ... For the mathematical constant see: E (mathematical constant). ... “Make-up” redirects here. ... Jet fuel is a type of aviation fuel designed for use in jet-engined aircraft. ... This does not cite any references or sources. ... Pumpjack pumping an oil well near Lubbock, Texas Ignacy Łukasiewicz - inventor of the refining of kerosene from crude oil. ... Embalming, in most modern cultures, is the art and science of temporarily preserving human remains to forestall decomposition and to make them suitable for display at a funeral. ...

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 suppressed 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: Alkylation is the transfer of an alkyl group from one molecule to another. ... Cresols are organic chemical compounds which are methylphenols. ... 1-butene cis-2-butene trans-2-butene methylpropene There are four alkenes which have four carbon atoms and one double bond in their chemical structure. ... Tocopherol, or Vitamin E, is a fat-soluble vitamin in eight forms that is an important antioxidant. ... A single chemical reaction is said to have undergone autocatalysis, or be autocatalytic, if the reaction product is itself the catalyst for that reaction. ...

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. For other uses of THF, see THF (disambiguation) Tetrahydrofuran is a heterocyclic organic compound. ... This article is about the chemical compound. ... The general structure of an organic peroxide. ...

Use in foods

BHT was patented in 1947 and received approval of the Food and Drug Administration for use as a food additive and preservative in 1954. BHT reacts with free radicals, slowing the rate of autoxidation in food, preventing changes in the food's color, odor, and taste.^[2] For other uses, see Patent (disambiguation). ... Year 1947 (MCMXLVII) was a common year starting on Wednesday (link will display full 1947 calendar) of the Gregorian calendar. ... “FDA” redirects here. ... Year 1954 (MCMLIV) was a common year (link will display full calendar) of the Gregorian calendar. ... In chemistry free radicals are uncharged atomic or molecular species with unpaired electrons or an otherwise open shell configuration. ... The most fundamental reactions in chemistry are the redox processes. ...

Controversy

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. Products with BHT include McDonald's sausage patties, <http://app.mcdonalds.com/bagamcmeal?process=item&itemID=83>; Chiclets and Trident gum (Cadbury Adams); Orbit White sugarfree gum (Wrigley Jr. Company); Diamond Foods nuts; Quaker Oats Granola Bites; Banquet Brown 'N Serve sausage links (ConAgra); packaging material for some Kraft Foods products (including Nabisco and Post brands); Banana Boat facial sunblock stick (Sun Pharmaceuticals); Safeway Corn Flakes; Stride gum; Wheat Thins; Kellogg's Rice Krispies. BHT is also commonly referred to as "Jeebonaut" [Gee-BO-Not] Year 1958 (MCMLVIII) was a common year starting on Wednesday (link will display full calendar) of the Gregorian calendar. ...

References

1. ^ 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
2. ^ Fujisawa, S.; Kadomab, Y.; Yokoe, I. "Radical-scavenging activity of butylated hydroxytoluene (BHT) and its metabolites" Chemistry and Physics of Lipids 130 (2004) pp. 189–195. DOI 10.1016/j.chemphyslip.2004.03.005.

See also

• Butylated hydroxyanisole (BHA)

Butylated hydroxyanisole (BHA) is a mixture of two isomeric organic compounds, 2-tert-butyl-4-hydroxyanisole and 3-tert-butyl-4-hydroxyanisole. ...

External links

• Why are BHA and BHT in foods? Are they safe?
• Bioassay of BHT, includes structure
• BUTYLATED HYDROXYTOLUENE (ICSC)
• Butylated Hydroxytoluene (BHT) Antioxidant