Tert-Butylhydroquinone 5316962 215711698 2008-05-29T11:07:57Z DOI bot 6652755 Citation maintenance. Initiated by [[User:Tarun2k|Tarun2k]]. You can [[WP:DOI|use this bot]] yourself! Please [[User:DOI_bot/bugs|report any bugs]]. {{lowercase|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 = C<sub>10</sub>H<sub>14</sub>O<sub>2</sub> | 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)<br />[[4-tert-Butylcatechol]] (TBC) }} }} '''''tert''-Butylhydroquinone''' ('''TBHQ''', '''tertiary butylhydroquinone''') is an [[aromatic]] [[organic compound]] which is a type of [[phenols|phenol]]. It is a derivative of [[hydroquinone]], substituted with ''tert''-[[butyl]] group. ==Applications== TBHQ is a highly effective [[preservative]] for unsaturated [[vegetable oil]]s 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 (chemistry)|stabilizer]] to inhibit autopolymerization of [[organic peroxide]]s. In perfumery, it is used as a fixative to lower the evaporation rate and improve stability. It is also added to [[varnish]]es, [[lacquer]]s, [[resin]]s, 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.<ref>[http://www.inchem.org/documents/jecfa/jecmono/v35je03.htm Tert-Butylhydroquinone] - safety summary from The International Programme on Chemical Safety</ref> A number of studies have shown that prolonged exposure to TBHQ may induce carcinogenity.<ref>{{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}}</ref> Other studies, however, have shown inhibition against [[Heterocyclic amines|HCA]]-induced carcinogenesis (by depression of metabolic activation) for TBHQ and other phenolic antioxidants.<ref>{{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}}</ref> ==References== {{reflist}} {{DEFAULTSORT:Butylhydroquinone, tert-}} [[Category:Benzenediols]] [[Category:Food antioxidants]] [[hu:Butil-hidrokinon]]