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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
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, electrical transformer oil¹, and embalming fluid.

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.²

In the chemical industry it is added to tetrahydrofuran and diethyl ether in order to inhibit the formation of dangerous organic peroxides.

Controversy

In the 1970s, Benjamin Feingold, a San Francisco MD who established the "Feingold Diet" claimed that BHT could produce hyperactivity in some children. In addition, there has been some controversy with regard to BHT and cancer risk,³ some studies showing the potential to increase and some showing a decrease in risk.⁴⁵⁶ Some food industries have voluntarily eliminated this additive from their products, and since the 1970s it has been steadily replaced with the less studied BHA.

On the other hand, BHT is also marketed as a health food supplement in capsule form. It has been reported to have anti-viral effects, particularly in use against herpes family viruses and in combination with L-lysine and Vitamin C.^78910111213 This latter use has made it into some of the more popular literature.¹⁴¹⁵

References

1. ^ Ficha de Datos de Seguridad, Transformador 64, page 1, retrieved December 29, 2008, (español).
2. ^ 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
3. ^ "Butylated hydroxytoluene (BHT)", IARC Monographs on the Evaluation of Carcinogenic Risks to Humans, 1986;40:161-206.
4. ^ Kensler TW, Egner PA, Trush MA, Bueding E, Groopman JD, "Modification of aflatoxin B1 binding to DNA in vivo in rats fed phenolic antioxidants, ethoxyquin and a dithiothione", Carcinogenesis, 1985;6(5):759-63.
5. ^ Williams GM, Iatropoulos MJ, "Inhibition of the hepatocarcinogenicity of aflatoxin B1 in rats by low levels of the phenolic antioxidants butylated hydroxyanisole and butylated hydroxytoluene", Cancer Lett. 1996;104(1):49-53.
6. ^ Franklin RA, "Butylated hydroxytoluene in sarcoma-prone dogs", Lancet. 1976;1(7972):1296.
7. ^ Snipes W, Person S, Keith A, Cupp J, "Butylated hydroxytoluene inactivates lipid-containing viruses", Science. 1975;188(4183):64-6.
8. ^ Brugh M Jr, "Butylated hydroxytoluene protects chickens exposed to Newcastle disease virus. Science", 1977;197(4310):1291-2.
9. ^ Richards JT, Katz ME, Kern ER, "Topical butylated hydroxytoluene treatment of genital herpes simplex virus infections of guinea pigs", Antiviral Res. 1985;5(5):281-90.
10. ^ Kim KS, Moon HM, Sapienza V, Carp RI, Pullarkat R, "Inactivation of cytomegalovirus and Semliki Forest virus by butylated hydroxytoluene", J Infect Dis. 1978;138(1):91-4.
11. ^ Pirtle EC, Sacks JM, Nachman RJ, "Antiviral effectiveness of butylated hydroxytoluene against pseudorabies (Aujeszky’s disease) virus in cell culture, mice, and swine", Am J Vet Res. 1986;47(9):1892-5.
12. ^ Chetverikova LK, Ki’ldivatov II, Inozemtseva LI, Kramskaia TA, Filippov VK, et al. "Factors of antiviral resistance in the pathogenesis of influenza in mice", Vestn Akad Med Nauk SSSR. 1989;(11):63-8. [in Russian]
13. ^ Chetverikova LK, Inozemtseva LI, "Role of lipid peroxidation in the pathogenesis of influenza and search for antiviral protective agents" Vestn Ross Akad Med Nauk. 1996;(3):37-40. [in Russian]
14. ^ Pearson D, Shaw S, "Life Extension: A Practical Scientific Approach", New York, NY: Warner Books, Inc.; 1982:206-207.
15. ^ Mann JA, Fowkes SW, "Wipe Out Herpes with BHT", Manhattan Beach, Calif: MegaHealth Society; 1983.

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

Wikipedia content modification information:

• This page was last modified on 30 December 2008, at 00:44.

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