20021
3-tert-Butyl-4-hydroxyanisole
≥98% (sum of isomers, GC), ≤10% 2-BHA basis (GC)
Synonym(s):
2-tert-Butyl-4-methoxyphenol, 3-BHA, BHA
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About This Item
Empirical Formula (Hill Notation):
C11H16O2
CAS Number:
Molecular Weight:
180.24
Beilstein:
1867499
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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Quality Level
Assay
≥98% (sum of isomers, GC)
form
solid
composition
2-BHA, ≤10% GC
3-BHA, ≥90% GC
impurities
≤1% 4-hydroxyanisole
ign. residue
≤0.05%
mp
48-63 °C
solubility
ethanol: soluble 1 g/10 mL, clear, colorless to faint yellow or tan
SMILES string
COc1ccc(O)c(c1)C(C)(C)C
InChI
1S/C11H16O2/c1-11(2,3)9-7-8(13-4)5-6-10(9)12/h5-7,12H,1-4H3
InChI key
MRBKEAMVRSLQPH-UHFFFAOYSA-N
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General description
The voltammetric behavior of 3-tert-butyl-4-hydroxyanisole at a polymer electrode modified with nickel phthalocyanine (as electron mediator) was studied.
Application
- Regulation of Smad signaling in mesenchymal stem cells: 3-tert-Butyl-4-hydroxyanisole disrupts the differentiation of C3H10T1/2 mesenchymal stem cells into brown adipocytes by modulating Smad signaling pathways, with potential implications for obesity and metabolic syndrome research (Wang et al., 2023).
Hazard Statements
Precautionary Statements
Hazard Classifications
Aquatic Chronic 2
Storage Class Code
11 - Combustible Solids
WGK
WGK 2
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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C de la Fuente et al.
Talanta, 49(2), 441-452 (2008-10-31)
The voltammetric behaviour of the antioxidants 3-tert-butyl-4-hydroxyanisole (BHA) and tert-butylhydroquinone (TBHQ), at a polymer electrode modified with nickel phthalocyanine as electron mediator, is described, and an electroanalytical method for the determination of these antioxidants based on their electrochemical oxidation on
K Tajima et al.
Drug metabolism and disposition: the biological fate of chemicals, 20(6), 816-820 (1992-11-01)
3-Tert-butyl-4-hydroxyanisole (3-BHA) was metabolized in the presence of horseradish peroxidase and hydrogen peroxide to 2-tert-butyl-p-benzoquinone (TBQ), 2,3-epoxy-5-tert-butyl-1,4-benzoquinone (TBQ-epoxide), and two known dimers. The formation of TBQ from 3-BHA required both horseradish peroxidase and hydrogen peroxide. When 2.5 mM 3-BHA was
A Matsuoka et al.
Mutation research, 241(2), 125-132 (1990-06-01)
The mutagenicity of 3-tert-butyl-4-hydroxyanisole (BHA) and its metabolites was investigated in the reverse mutation assay using S. typhimurium strains and the chromosomal aberration test in vitro using a Chinese hamster fibroblast cell line, CHL. BHA, tert-butylhydroquinone (BHQ), tert-butylquinone (BQ) and
K Tajima et al.
Drug metabolism and disposition: the biological fate of chemicals, 19(6), 1028-1033 (1991-11-01)
After ip administration of 3-tert-butyl-4-hydroxyanisole (3-BHA) to rats, two previously undocumented metabolites 2-tert-butyl-5-methylthiohydroquinone (TBHQ-5-SMe) and 2-tert-butyl-6-methylthiohydroquinone (TBHQ-6-SMe) were identified in the urine by comparison with the authentic samples by GC/MS. In addition to these metabolites, 3-tert-butyl-4,5-dihydroxyanisole was also detected in
P A Schilderman et al.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 33(2), 99-109 (1995-02-01)
The effect of metabolic activation of the food additive 3-tert-butyl-4-hydroxyanisole (BHA) by prostaglandin H synthase on the gastro-intestinal cell proliferation was determined by studies of the nature and the time dependency of early lesions in the forestomach, glandular stomach and
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