B1378

2,6-Di-tert-butyl-4-methylphenol

≥99.0% (GC), powder

• Synonym(s): 2,6-Di-tert-butyl-p-cresol, BHT, Butylated hydroxytoluene, Butylhydroxytoluene, DBPC
• Linear Formula: [(CH₃)₃C]₂C₆H₂(CH₃)OH
• CAS Number: 128-37-0
• Molecular Weight: 220.35
• Beilstein: 1911640
• EC Number: 204-881-4
• MDL number: MFCD00011644
• UNSPSC Code: 12352100
• PubChem Substance ID: 57653920
• NACRES: NA.22

Properties

• vapor density: 7.6 (vs air)
• vapor pressure: <0.01 mmHg ( 20 °C)
• Assay: ≥99.0% (GC)
• form: powder
• autoignition temp.: 878 °F
• bp: 265 °C (lit.)
• mp: 69-73 °C (lit.)
• solubility: ethanol: 100 mg/mL; vegetable oils: soluble
• SMILES string: Cc1cc(c(O)c(c1)C(C)(C)C)C(C)(C)C
• 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
• InChI key: NLZUEZXRPGMBCV-UHFFFAOYSA-N
• Gene Information: human ... CAPN1(823) ; rat ... Capn1(29153) , Nos1(24598)

Description

Application

• Thermal decomposition characteristics of BHT and its peroxide (BHTOOH): BHT is highlighted for its excellent antioxidant properties, which degrade into BHTOOH under specific conditions (S Dai, et al., 2024).
• Relaxation mechanisms in low-stress polymer networks: BHT is utilized in polymer networks to assess its effects on the mechanical properties and durability of dental composites (SH Lewis, et al., 2024).
• Compatibility and safety of labels for pharmaceutical packaging: The study found BHT in labels, indicating its widespread use in pharmaceutical packaging due to its stabilizing properties (C Fu, et al., 2023).

Biochem/physiol Actions

Butylated hydroxytoluene (BHT) is a phenolic antioxidant. It has been shown to inhibit lipid peroxidation. It causes lung injury and promotes tumors in mice, but this may be due to a metabolite of BHT, 6-tert-butyl-2-[2′-(2′-hydroxymethyl)-propyl]-4-methylphenol. Metabolites of BHT have also been reported to induce DNA strand breaks and internucleosomal DNA fragmentation (a characteristic of apoptosis) in cultured cells. In rats, a single intraperitoneal injection of BHT (60 mg/kg body mass) results in a significant increase in nuclear DNA methyl transferase activity in the liver, kidneys, heart, spleen, brain and lungs. Incubation of alveolar macrophages with BHT significantly reduced the level of TNF-α which may explain the mechanism by which this antioxidant reduces inflammation. Preincubation of aspirin-treated platelets with BHT inhibits the secretion, aggregation, and protein phosphorylation induced by protein kinase C activators. BHT was also found to inhibit the initiation of hepatocarcinogenesis by aflatoxin B1.

Safety Information

• Pictograms: GHS09
• Signal Word: Warning
• Hazard Statements: H410
• Precautionary Statements: P273 - P391 - P501
• Hazard Classifications: Aquatic Acute 1 - Aquatic Chronic 1
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 2
• Flash Point(F): 260.6 °F - open cup
• Flash Point(C): 127 °C - open cup
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves