1879-09-0
Chemical Structure
2-(tert-Butyl)-4,6-dimethylphenol
Synonym(s): 6-tert-Butyl-2,4-xylenol
- CAS No.: 1879-09-0
- Formula:C12H18O
- Molecular Weight:178.27
IUPAC Name: 2-(tert-butyl)-4,6-dimethylphenol
InChIKey: OPLCSTZDXXUYDU-UHFFFAOYSA-N
SMILES: OC1=C(C(C)(C)C)C=C(C)C=C1C
Biological Activity: 2-(tert-Butyl)-4,6-dimethylphenol (6-tert-Butyl-2,4-xylenol) is an electrophilic alkylating agent, gasoline antioxidant and hydration substrate. 2-(tert-Butyl)-4,6-dimethylphenol inhibits SERCA activity in rabbit hindleg microsomes with an IC50 of 53 μM. Oxidation of 2-(tert-Butyl)-4,6-dimethylphenol generates the intermediate BDMP-QM, which covalently modifies nitrogen sites of proteins, polypeptides and free amino acids via Michael addition, triggering covalent modification of macromolecules and mediating cytotoxicity. 2-(tert-Butyl)-4,6-dimethylphenol is widely used in toxicological and biochemical studies of alkylphenols[1][2][3].
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2-(tert-Butyl)-4,6-dimethylphenol | 2-(tert-Butyl)-4,6-dimethylphenol (6-tert-Butyl-2,4-xylenol) is an electrophilic alkylating agent, gasoline antioxidant and hydration substrate. 2-(tert-Butyl)-4,6-dimethylphenol inhibits SERCA activity in rabbit hindleg microsomes with an IC50 of 53 μM. Oxidation of 2-(tert-Butyl)-4,6-dimethylphenol generates the intermediate BDMP-QM, which covalently modifies nitrogen sites of proteins, polypeptides and free amino acids via Michael addition, triggering covalent modification of macromolecules and mediating cytotoxicity. 2-(tert-Butyl)-4,6-dimethylphenol is widely used in toxicological and biochemical studies of alkylphenols. | |||||||||||||||||||||
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- [1]. McCracken PG, et al. Covalent Modification of Proteins and Peptides by the Quinone Methide from 2-tert-Butyl-4,6-dimethylphenol: Selectivity and Reactivity with Respect to Competitive Hydration. The Journal of Organic Chemistry. 1997;62(6):1820-1825.
- [2]. Paula S, et al. Novel phenolic inhibitors of the sarco/endoplasmic reticulum calcium ATPase: identification and characterization by quantitative structure-activity relationship modeling and virtual screening. Journal of enzyme inhibition and medicinal chemistry. 2015 Feb;30(1):1-8. [Content Brief]
- [3]. Previc EP, et al. A New Synthesis Method for a Gasoline Antioxidant. Industrial & Engineering Chemistry. 1961;53(6):469-470.
Keywords
