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Merck
CN

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

Key Documents

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Product Name

3-tert-Butyl-4-hydroxyanisole, ≥98% (sum of isomers, GC), ≤10% 2-BHA basis (GC)

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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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).

General description

The voltammetric behavior of 3-tert-butyl-4-hydroxyanisole at a polymer electrode modified with nickel phthalocyanine (as electron mediator) was studied.

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
WXBF7926V
WXBF6118V
BCCJ6531
BCCK5134
BCCG8386

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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
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
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
M M Peters et al.
Cancer research, 56(5), 1006-1011 (1996-03-01)
3-tert-Butyl-4-hydroxyanisole and tert-butyl-hydroquinone (TBHQ) are antioxidants known to promote renal and bladder carcinogenesis in the rat, although the mechanisms of these effects are unclear. Because glutathione (GSH) conjugates of a variety of hydroquinones are nephrotoxic, and because 2-tert-butyl-5-(glutathion-S-yl)hydroquinone [5-(GSyl)TBHQ], 2-tert-butyl-6-(glutathion-S-yl)hydroquinone
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