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Tert-Butylhydroquinone

Template:DISPLAYTITLE:tert-Butylhydroquinone

Tert-Butylhydroquinone

General
Systematic name	2-(1,1-Dimethylethyl)-1,4-benzenediol
Other names	TBHQ(i)
Molecular formula	C₁₀H₁₄O₂
SMILES	CC(C)(C)c1cc(O)ccc1O
Molar mass	166.22 g/mol
Appearance	Tan powder
CAS number	[1948-33-0]
Properties
Density and phase	? g/cm³, ?
Solubility in water	Insoluble
Melting point	127-129 °C
Boiling point	?°C (? K)
Acidity (pK_a)	?
Structure
Dipole moment	? D
Hazards
MSDS	External MSDS
Main hazards	Harmful
NFPA 704
Flash point	? °C
R/S statement	R: R22 S: S26 S27 S28
RTECS number	?
Supplementary data page
Structure and properties	n, ε_r, etc.
Thermodynamic data	Phase behaviour Solid, liquid, gas
Spectral data	UV, IR, NMR, MS
Related compounds
Related compounds	Butylated hydroxyanisole (BHA) 4-tert-Butylcatechol (TBC)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

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tert-Butylhydroquinone (TBHQ, tertiary butylhydroquinone) is an aromatic organic compound which is a type of phenol. It is a derivative of hydroquinone, substituted with tert-butyl group.

Applications

TBHQ is a highly effective antioxidant for unsaturated vegetable oils and many edible animal fats. It does not cause discoloration even in the presence of iron, and does not change flavor nor odor of the material it is added to. It can be combined with other antioxidants such as butylated hydroxyanisole (BHA). As food additive, its E number is E319, where it is used as an antioxidant. It is added to a wide range of foods, with highest limit (1000 mg/kg) permitted for frozen fish and fish products. Its primary advantage is enhancing storage life.

It is used industrially as a stabilizer to inhibit autopolymerization of organic peroxides. In perfumery, it is used as a fixative to lower the evaporation rate and improve stability. It is also added to varnishes, lacquers, resins, and oil field additives.

Carcinogenicity

In high doses, it has some negative health effects on lab animals, such as precursors to stomach tumors and damage to DNA.^[1] A number of studies have shown that prolonged exposure to TBHQ may induce carcinogenity.^[2] Other studies, however, have shown protective effects for TBHQ and other phenolic antioxidants.^[3]

References

^ Tert-Butylhydroquinone - safety summary from The International Programme on Chemical Safety
^ Gharavi N, El-Kadi A (2005). "tert-Butylhydroquinone is a novel aryl hydrocarbon receptor ligand". Drug Metab Dispos 33 (3): 365-72. PMID 15608132.
^ Hirose M, Takahashi S, Ogawa K, Futakuchi M, Shirai T, Shibutani M, Uneyama C, Toyoda K, Iwata H (1999). "Chemoprevention of heterocyclic amine-induced carcinogenesis by phenolic compounds in rats". Cancer Lett 143 (2): 173-8. PMID 10503899.

Categories: Benzenediols | Food antioxidants

This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Tert-Butylhydroquinone". A list of authors is available in Wikipedia.