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

• CAS: 128-37-0
• Catalog Number: ACM128370-6
• Category: Main Products
• Molecular Weight: 220.35
• Molecular Formula: C15H24O
• Description: Butylated hydroxytoluene (BHT), also known as dibutylhydroxytoluene, is a lipophilic organic compound, chemically a derivative of phenol, that is useful for its Antioxidants properties. European and U.S. regulations allow small amounts to be used as a food additive. In addition to this use, BHT is widely used to prevent oxidation in fluids (e.g. fuel, oil) and other materials where free radicals must be controlled.
• Synonyms: 4-methyl-2,6-di-tert-butylphenol;Butylhydroxytoluene;2,6-Di-tert-butyl-p-cresol;Phenol, 2,6-bis(1,1-dimethylethyl)-4-methyl-;2,6-di-tert-butyl-4-methyl-phenol
• IUPAC Name: 2,6-ditert-butyl-4-methylphenol
• Canonical SMILES: CC1=CC(=C(C(=C1)C(C)(C)C)O)C(C)(C)C
• InChI Key: NLZUEZXRPGMBCV-UHFFFAOYSA-N
• Boiling Point: 265°C(lit.)
• Melting Point: 69-71ºC
• Flash Point: 127ºC
• Density: 1.048
• Appearance: Crystalline
• EC Number: 204-881-4
• Exact Mass: 220.18300
• Hazard Codes: Xn
• Hazard Statements: Xn,N
• HS Code: 2907199090
• LogP: 4.29560
• MDL Number: MFCD00011644
• Packing Group: III
• PSA: 2.23
• Refractive Index: 1.4859
• RIDADR: UN 3077
• Safety Description: 26-36-37/39-61-60
• Stability: Stable, but light-sensitive. Incompatible with acid chlorides, acid anhydrides, brass, copper, copper alloys, steel, bases, oxidizing agents. Combustible.
• Storage Conditions: 0-6ºC
• Supplemental Hazard Statements: H302-H315-H317-H319-H370-H373-H401-H411-H410
• Symbol: GHS09,GHS07,GHS08
• Vapor Density: 7.6
• Vapor Pressure: <0.01 mm Hg ( 20 °C)
• WGK Germany: 1

Case Study

Evaluation of the Antibiofilm Properties of 2,6-Di-Tert-Butyl-4-Methylphenol

Santhakumari, Sivasubramanian, et al. International journal of food microbiology, 2018, 281, 60-71.

The antibiofilm potential of 2,6-di-tert-butyl-4-methylphenol (DTBMP) against Vibrio spp. was evaluated in vitro and in vivo. The impact of the test compound on vibrios biofilm formation was assessed using the crystal violet (CV) assay to measure the biofilm biomass spectrometrically. The results showed that DTBMP could effectively inhibit the bioluminescence production and other biofilm-related virulence properties of the pathogenic Vibrio harveyi. DTBMP showed potential for application in the treatment of biofilm-associated Vibrio infections in aquaculture.
Determination of effective biofilm inhibition concentration (BIC)
· The DTBMP was prepared as a 50 mg/ml stock solution, which was dissolved in absolute ethanol and stored at 4 °C until further use.
· A 1% concentration of the target bacterial culture with an OD adjusted to 0.4 at 600 nm was mixed with 1 ml of mLB medium and incubated with various concentrations of DTBMP for 16 hours without agitation.
· Following the incubation period, the planktonic cells were eliminated, and the wells were washed twice with sterile water. The adhered cells in the MTP wells were stained with a 0.4% aqueous CV solution for 2 minutes, and then excess stain was removed by rinsing with flowing water.
· The CV bound cells were dissolved with 1 ml of 20% glacial acetic acid, and the intensity of the dissolved CV was measured using a spectrophotometer at OD 570 nm. The degree of biofilm inhibition was determined using the following formula: Percentage of inhibition = [(Control OD - Test OD) / Control OD] x 100.

The Anti-Inflammatory Activity of Artificial Antioxidant 2,6-Di-Tert-Butyl-4-Methylphenol and Its Combination

Murakami, Yukio, et al. in vivo, 2015, 29(2), 197-206.

This work evaluated the anti-inflammatory activity of several artificial complex phenolic compounds, including 2-tert-butyl-4-methoxyphenol (BHA), 2,6-di-tert-butyl-4-methylphenol (BHT) and 2,4,6-tri-tert-butylphenol (TBP) and their combination. The results showed that the combination of BHT and BHA with a molar ratio of 0.5-2 had a potent anti-inflammatory activity and had the potential to be used as an antioxidant in food and medicine.
Evaluation methods and results
· The anti-inflammatory activities of BHA, BHT, and TBP, as well as the combinations of BHT/BHA (molar ratios of 1:1, 1:2, 1:3, and 2:1), BHT/TBP (1:1), and BHA/TBP (1:1) were investigated using the gene expression system of cyclooxygenase-2 (Cox2) and tumor necrosis factor-α (Tnfa) in RAW264.7 cells. The impact of BHA, BHT, and TBP on the expression of Cox2 and Tnfa genes when exposed to LPS or Pg fimbriae was analyzed with real-time PCR.
· The combination of BHT/BHA (1:1 ratio) significantly increased the inhibitory effect on Cox2 and Tnfa gene expression when stimulated with LPS and fimbriae. BHT/TBP and BHA/TBP (both in a 1:1 ratio) slightly enhanced the inhibition of the Cox2 gene, but not the Tnfa gene. None of the antioxidants showed anti-inflammatory effects when exposed to LPS alone, but some activity was observed with Pg fimbriae. The combination of BHT/BHA had a more significant effect at a 1:2 or 2:1 ratio compared to a 1:1 ratio when inhibiting Cox2 mRNA expression from LPS stimulation, while a 1:3 ratio had no effect.