Tert-Butylhydroquinone

Chembox new
Name = Tert-Butylhydroquinone
ImageFile = Tert-butylhydroquinone.png ImageSize = 200px
ImageName =
IUPACName = 2-(1,1-Dimethylethyl)-1,4-benzenediol
OtherNames = TBHQ(i)
Section1 = Chembox Identifiers
SMILES = CC(C)(C)c1cc(O)ccc1O
CASNo = 1948-33-0
RTECS =
Section2 = Chembox Properties
Formula = C₁₀H₁₄O₂
MolarMass = 166.22 g/mol
Appearance = Tan powder
Density =
Solubility = Insoluble
MeltingPt = 127-129 °C
BoilingPt = (? K)
pKa =
Section3 = Chembox Structure
Dipole =
Section7 = Chembox Hazards
ExternalMSDS = [http://physchem.ox.ac.uk/MSDS/BU/tert-butyl_hydroquinone.html External MSDS]
MainHazards = Harmful
FlashPt =
RPhrases = R22
SPhrases = S26 S27 S28
Section8 = Chembox Related
OtherCpds = Butylated hydroxyanisole (BHA)
4-tert-Butylcatechol (TBC)

"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 it is added to. It can be combined with other preservatives such as butylated hydroxyanisole (BHA). As food additive, its E number is E319, where it is used as a preservative. 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. [ [http://www.inchem.org/documents/jecfa/jecmono/v35je03.htm Tert-Butylhydroquinone] - safety summary from The International Programme on Chemical Safety] A number of studies have shown that prolonged exposure to TBHQ may induce carcinogenity. [cite journal |author=Gharavi N, El-Kadi A |title=tert-Butylhydroquinone is a novel aryl hydrocarbon receptor ligand |journal=Drug Metab Dispos |volume=33 |issue=3 |pages=365–72 |year=2005 |pmid=15608132 |doi=10.1124/dmd.104.002253] Other studies, however, have shown inhibition against HCA-induced carcinogenesis (by depression of metabolic activation) for TBHQ and other phenolic antioxidants. [cite journal |author=Hirose M, Takahashi S, Ogawa K, Futakuchi M, Shirai T, Shibutani M, Uneyama C, Toyoda K, Iwata H |title=Chemoprevention of heterocyclic amine-induced carcinogenesis by phenolic compounds in rats |journal=Cancer Lett |volume=143 |issue=2 |pages=173–8 |year=1999 |pmid=10503899 |doi=10.1016/S0304-3835(99)00120-2]

References