3-tert-Butyl-4-Hydroxyanisole
3-Tert-butyl-4-hydroxyanisole (3-BHA) is one component of butylated hydroxyanisole (BHA). This compound is commonly used as a food additive; it exhibits antioxidative and anticancer activities. In leukemia cells, 3-BHA decreases the mitochondrial membrane potential, inhibits mitochondrial oxidative phosphorylation, induces apoptosis and DNA damage, and suppresses cellular proliferation. In animal models, 3-BHA induces phase II enzymes, increasing expression of quinone reductase and glutathione-S-transferase. Some studies suggest that 3-BHA may also be mutagenic.
References PubMed ID：:http://www.ncbi.nlm.nih.gov/pubmed/18832972
| Cas No. |
121-00-6 |
|---|---|
| Purity |
≥99% |
| Formula |
C11H16O2 |
| Formula Wt. |
180.25 |
| Chemical Name |
3-(1,1-Di-methylethyl)4-methoxyphenol |
| IUPAC Name |
2-tert-butyl-4-methoxyphenol |
| Synonym |
3-BHA |
| Melting Point |
69-71°C |
| Solubility |
Insoluble in water. Soluble in ethanol, acetone, or DMSO. |
| Appearance |
White Crystal Powder |
Hwang GH, Jeon YJ, Han HJ, et al. Protective effect of butylated hydroxylanisole against hydrogen peroxide-induced apoptosis in primary cultured mouse hepatocytes. J Vet Sci. 2014 Oct 8. [Epub ahead of print]. PMID: 25293491.
Okubo T, Yokoyama Y, Kano K, et al. Molecular mechanism of cell death induced by the antioxidant tert-butylhydroxyanisole in human monocytic leukemia U937 cells. Biol Pharm Bull. 2004 Mar;27(3):295-302. PMID: 14993791.
Prochaska HJ, Fernandes CL. Elevation of serum phase II enzymes by anticarcinogenic enzyme inducers: markers for a chemoprotected state? Carcinogenesis. 1993 Dec;14(12):2441-5. PMID: 8269610.
Matsuoka A, Matsui M, Miyata N, et al. Mutagenicity of 3-tert-butyl-4-hydroxyanisole (BHA) and its metabolites in short-term tests in vitro. Mutat Res. 1990 Jun;241(2):125-32. PMID: 2345551.
