4966 2,6-Di-tert-butyl-4-methylphenol 2,6-Di-tert-butyl-4-methylphenol is also known as butylated hydroxytoluene (BHT) or butylhydroxytoluene, is a lipophilic (fat-soluble) organic compound that is primarily used as an antioxidant food additive (E number E321) as well as an antioxidant additive in cosmetics, pharmaceuticals, jet fuels, rubber, petroleum products, electrical transformer oil, and embalming fluid. It is also found in certain plants, including soft-necked garlic. A recent study has found that phytoplankton, including the green algae, Botryococcus braunii, as well as three different cyanobacteria (Cylindrospermopsis raciborskii, Microcystis aeruginosa and Oscillatoria sp.) are capable of producing this compound. 128-37-0 31404 C15H24O 220.35 White powder 72 °C 265 °C 1.1 mg/mL Ingestion; Inhalation BHT is metabolized to quinone methides (QMs) which are responsible for promoting tumor formation in many animal models. One example of a QM is 2,6-di-tert-butyl-4-methylenecyclohexa-2,5-dienone (BHT-QM). QMs are strongly electrophilic and readily form adducts with proteins. Some of the QM targets include redox proteins such as glutathione S-transferase P1 (GST-P1), peroxiredoxin 6 (Prx6), Cu,Zn-superoxide dismutase (SOD1), carbonyl reductase, and selenium-binding protein 1, which have direct or indirect antioxidant functions. (A15087, A15355). The modification of these proteins leads to decreased cellular protection from electrophiles and oxidants. Alkylation also may interfere with GSTP1 regulation of stress kinases, thereby influencing phosphorylation and cell growth. BHT also binds to the retinoic acid receptor which can lead to changes in cell development. Oxidative metabolism (phase 1 reactions) mediated by the microsomal monooxygenase system is the major route for BHT degradation. Oxidation of the tert-butyl groups is most common in man. Gallates and 2-tert-butylhydroquinone are mainly metabolized by non-oxidative pathways (methylation or conjugation with sulphate and glucuronic acid). (A15352). In particular BHT is frequently metabolized to quinone methides (QMs) which are thought to be responsible for promoting tumor formation. One example of a QM is 2,6-di-tert-butyl-4-methylenecyclohexa-2,5-dienone (BHT-QM). QMs are strongly electrophilic and readily form adducts with proteins. In rats, the oral LD50 was > 2930 mg/kg bw, the LD50 after dermal exposure was > 2000 mg/kg 3, not classifiable as to its carcinogenicity to humans. (L135) BHT is primarily used as an antioxidant food additive (E number E321) as well as an antioxidant additive in cosmetics, pharmaceuticals, jet fuels, rubber, petroleum products, electrical transformer oil, and embalming fluid. 25 mg/kg/day for thyroid and liver damage. 100 mg/kg/day for cancer. BHT is of low acute toxicity. Acute exposure to BHT can cause coughs and sore throat (inhalation), redness on the skin (via contact) and abdominal pain, confusion, dizziness and nausea (via ingestion). Long-term exposure to high doses of BHT is toxic in mice and rats, causing liver, thyroid and kidney problems and affecting lung function and blood coagulation. BHT can act as a tumour promoter in certain situations (A15353) although it is not a genotoxic carcinogen. Limited evidence suggests that high doses of BHT may mimic estrogen (A15354), the primary female sex hormone, and prevent expression of male sex hormones, resulting in adverse reproductive affects. On chronic oral exposure of rats, liver and thyroid are the main targets. Doses above 25 mg/kg bw/day BHT resulted in thyroid hyperactivity and enlargement of the liver. For acute exposure: EYES: irrigate opened eyes for several minutes under running water. INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice. SKIN: should be treated immediately by rinsing the affected parts in cold running water for at least 15 minutes, followed by thorough washing with soap and water. If necessary, the person should shower and change contaminated clothing and shoes, and then must seek medical attention. INHALATION: supply fresh air. If required provide artificial respiration. 2014-09-11T05:21:57Z 2026-04-16T22:38:55Z http://en.wikipedia.org/wiki/Butylated_hydroxytoluene C14693 34247 D002084 DB16863 true CC1=CC(=C(O)C(=C1)C(C)(C)C)C(C)(C)C C15H24O InChI=1S/C15H24O/c1-10-8-11(14(2,3)4)13(16)12(9-10)15(5,6)7/h8-9,16H,1-7H3 NLZUEZXRPGMBCV-UHFFFAOYSA-N 220.3505 220.18271539 Exogenous Solid 5.10 HMDB33826 13835296 CHEM003867 DTXSID30591739 2,6-di-tert-butyl-4-methylphenol