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Tert-Butylhydroquinone
Antioxidant
Antioxidant
Butylated hydroxytoluene (BHT) 4-tert-Butylcatechol (TBC)
tert-Butylhydroquinone (TBHQ, tertiary butylhydroquinone, tBHQ) is a synthetic aromatic organic compound which is a type of phenol. It is a derivative of hydroquinone, substituted with a tert-butyl group.
Applications
Food preservative
In foods, TBHQ is used as an antioxidant 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.
Other
In perfumery, it is used as a fixative to lower the evaporation rate and improve stability.
It is used industrially as a stabilizer to inhibit autopolymerization of organic peroxides.
It is used as an antioxidant in biodiesel.
Polaroid uses it as a photographic developer in their black and white and Reclaimed Blue films.
Safety and regulation
The European Food Safety Authority (EFSA) and the United States Food and Drug Administration (FDA) have evaluated TBHQ and determined that it is safe to consume at the concentration allowed in foods. The FDA and European Union both set an upper limit of 0.02% (200mg/kg) of the oil or fat content in foods. It has not been approved in Japan, hence import of food containing TBHQ for selling is not allowed in Japan as of 2007.
At very high doses, it has some negative health effects on lab animals, such as producing precursors to stomach tumors and damage to DNA. A number of studies have shown that prolonged exposure to very high doses of TBHQ may be carcinogenic, especially for stomach tumors. Other studies, however, have shown opposite effects including 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) and reduction of nitrosamine-induced carcinogenesis (likely due to phase II enzyme induction via Nrf2). The EFSA considers TBHQ to be noncarcinogenic.
In addition, TBHQ has been identified by high-throughput screening as having potential immunotoxic effects in 2021. It was previously reported in 2014 that TBHQ enhances allergy response in mice by promoting Th2 cells through Nrf2.
Experiments on its genotoxicity at high doses are inconsistent. Its oxidized form TBBQ may be responsible for some toxic effects. There exists a wide margin of safety between food-additive doses and doses used in studies.
There have been reports of vision disturbances in individuals exposed to this chemical.
References
References
- It can be combined with other preservatives such as [[butylated hydroxyanisole]] (BHA). As a [[food additive]], its [[E number]] is '''E319'''. It is added to a wide range of foods. Its primary advantage is extending storage life.''Fats and oils: formulating and processing for applications'', Richard D. O'Brien, page 168
- (2011). "Behaviour of the antioxidant tert-butylhydroquinone on the storage stability and corrosive character of biodiesel". Fuel.
- Polaroid. "Introducing Polaroid Reclaimed Blue 600 film: no blue dye needed".
- [https://www.fda.gov/food/ingredientspackaginglabeling/foodadditivesingredients/ucm091048.htm "Food Additive Status List"]{{dead link. (May 2025)
- [http://www.efsa.europa.eu/en/efsajournal/pub/84 "Opinion of the Scientific Panel on food additives, flavourings, processing aids and materials in contact with food (AFC) on a request from the Commission related to tertiary-Butylhydroquinone (TBHQ)"]. [[European Food Safety Authority]], 12 July 2004
- [http://law.justia.com/cfr/title21/21-3.0.1.1.3.2.1.18.html 21 C.F.R. § 172.185]
- (9 January 2007). "TBHQ (t-butylhydroquinone) detected in imported foods".
- [http://www.inchem.org/documents/jecfa/jecmono/v35je03.htm Tert-Butylhydroquinone] - safety summary from The International Programme on Chemical Safety
- (2005). "tert-Butylhydroquinone is a novel aryl hydrocarbon receptor ligand". Drug Metab Dispos.
- (1993). "Modification of carcinogenesis by -tocopherol, t-butylhydro-quinone, propyl gallate and butylated hydroxytoluene in a rat multi-organ carcinogenesis model". [[Oxford University Press]].
- (1999). "Chemoprevention of heterocyclic amine-induced carcinogenesis by phenolic compounds in rats". Cancer Lett.
- (1 January 2007). "Chemoprotective and Carcinogenic Effects of tert-Butylhydroquinone and Its Metabolites". Current Drug Metabolism.
- (1986). "Toxicology of tert-butylhydroquinone (TBHQ)". [[Food and Chemical Toxicology]].
- (2021-03-24). "Investigating Molecular Mechanisms of Immunotoxicity and the Utility of ToxCast for Immunotoxicity Screening of Chemicals Added to Food". International Journal of Environmental Research and Public Health.
- (1 May 2014). "The Nrf2 activator, tBHQ, exacerbates immediate hypersensitivity response to food allergen (HYP7P.315)". The Journal of Immunology.
- "T-BUTYLHYDROQUINONE - National Library of Medicine HSDB Database".
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