| tert-Butylhydroquinone | |
|---|---|
 |
|
| IUPAC name |
2-(1,1-Dimethylethyl)-1,4-benzenediol
|
| Other names | TBHQ(i) |
| Identifiers | |
| CAS number | 1948-33-0 |
| SMILES |
CC(C)(C)c1cc(O)ccc1O
|
| Properties | |
| Molecular formula | C10H14O2 |
| Molar mass | 166.22 g/mol |
| Appearance | Tan powder |
| Melting point |
127-129 °C |
| Boiling point |
273 °C |
| Solubility in water | Insoluble |
| Hazards | |
| MSDS | External MSDS |
| R-phrases | R22 |
| S-phrases | S26 S27 S28 |
| 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 references | |
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 preservative 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 or odor of the material to which it is added. It can be combined with other preservatives such as butylated hydroxyanisole (BHA). As a food additive, its E number is E319, where it is used as a preservative. It is added to a wide range of foods, with the highest limit (1000 mg/kg) permitted for frozen fish and fish products. TBHQ as a food additive is regulated in the United States by 21 C.F.R. § 172.185.[1] 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.[2] A number of studies have shown that prolonged exposure to TBHQ may induce carcinogenity.[3] Other studies, however, have shown inhibition against HCA-induced carcinogenesis (by depression of metabolic activation) for TBHQ and other phenolic antioxidants (TBHQ was one of several, and not the most potent).[4]
References
- ^ 21 C.F.R. § 172.185
- ^ 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. doi:. 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. doi:. PMID 10503899.
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