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20021

Sigma-Aldrich

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:
121-00-6
Molecular Weight:
180.24
Beilstein:
1867499
EC Number:
204-442-7
MDL number:
MFCD00040484
UNSPSC Code:
12352100
PubChem Substance ID:
57647769
NACRES:
NA.22

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).

Pictograms

Environment
GHS09

Hazard Statements

H411

Precautionary Statements

P273 - P391 - P501

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

Certificates of Analysis (COA)

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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
Mengxiao Xie et al.
Journal of autoimmunity, 102, 96-113 (2019-05-28)
The subset of regulatory T (Treg) cells, with its specific transcription Foxp3, is a unique cell type for the maintenance of immune homeostasis by controlling effector T (Teff) cell responses. Although it is common that a defect in Treg cells
L K Lam et al.
Carcinogenesis, 12(12), 2311-2315 (1991-12-01)
Carcinogen-induced aberrant crypts (AC) of the colon are a precancerous state that leads to malignancy. The inhibition of AC formation by chemopreventive agents was evaluated in this study. Colon AC were induced by 1,2-dimethylhydrazine (DMH) in 3 weeks in CF1
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, 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
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