tert-Butylhydroquinone

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Template:Chembox header | Tert-Butylhydroquinone
Tert-Butylhydroquinone
Template:Chembox header | 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]
Template:Chembox header | Properties
Density and phase ? g/cm³, ?
Solubility in water Insoluble
Melting point 127-129 °C
Boiling point ?°C (? K)
Acidity (pKa) ?
Template:Chembox header | Structure
Dipole moment ? D
Template:Chembox header | Hazards
MSDS External MSDS
Main hazards Harmful
NFPA 704
Flash point ? °C
R/S statement R: Template:R22
S: Template:S26 Template:S27 Template:S28
RTECS number ?
Template:Chembox header | Supplementary data page
Structure and
properties
n, εr, etc.
Thermodynamic
data
Phase behaviour
Solid, liquid, gas
Spectral data UV, IR, NMR, MS
Template:Chembox header | Related compounds
Related compounds Butylated hydroxyanisole (BHA)
4-tert-Butylcatechol (TBC)
Template:Chembox header | 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.

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