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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 (pKa)  ?
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, εr, 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

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

  1. ^ Tert-Butylhydroquinone - safety summary from The International Programme on Chemical Safety
  2. ^ Gharavi N, El-Kadi A (2005). "tert-Butylhydroquinone is a novel aryl hydrocarbon receptor ligand". Drug Metab Dispos 33 (3): 365-72. PMID 15608132.
  3. ^ 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.
 
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.
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