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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

Quality Level

200

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
K Morimoto et al.
Carcinogenesis, 12(4), 703-708 (1991-04-01)
DNA damage in the forestomach epithelium of male F344 rats was tested by alkaline elution assay following oral administration of 3-tert-butyl-4-hydroxyanisole (3-BHA) and its free metabolites. Although 1% 3-BHA and 0.001% tert-butylhydroquinone (BHQ) caused no detectable DNA damage, a tert-butylquinone
M Hirose et al.
Toxicology, 53(1), 33-43 (1988-12-16)
The urinary and fecal metabolites of orally administered 2-tert-butyl-4-hydroxyanisole (2-BHA) and 3-tert-butyl-4-hydroxyanisole (3-BHA) in rats were identified. Samples of 2-day pooled urine and feces of rats given a single intragastric dose of 1 g/kg body wt of tert[butyl-14C]3-BHA (*Bu-3-BHA). tert[butyl-14C]2-BHA
M G Salgo et al.
Archives of biochemistry and biophysics, 333(2), 482-488 (1996-09-15)
Peroxynitrite is a strong oxidant that reacts with a variety of biomolecules in vivo and in vitro. When rat thymocytes in phosphate buffer are exposed to 25 microM peroxynitrite for 10 min, DNA single strand breaks (SSB) can be detected.
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
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