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Merck

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:
121-00-6
Molecular Weight:
180.24
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
57647769
EC Number:
204-442-7
Beilstein/REAXYS Number:
1867499
MDL number:
MFCD00040484
Assay:
≥98% (sum of isomers, GC)
Form:
solid

Key Documents

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InChI key

MRBKEAMVRSLQPH-UHFFFAOYSA-N

InChI

1S/C11H16O2/c1-11(2,3)9-7-8(13-4)5-6-10(9)12/h5-7,12H,1-4H3

SMILES string

COc1ccc(O)c(c1)C(C)(C)C

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

Quality Level

200

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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

hcodes

H411

Hazard Classifications

Aquatic Chronic 2

Storage Class

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
WXBF8227V
WXBF7926V
WXBF6118V
BCCJ6531
BCCK5134

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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
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
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
View All Related Papers

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