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429074

Sigma-Aldrich

2-tert-Butyl-1,4-benzoquinone

98%

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About This Item

Linear Formula:
(CH3)3CC6H3(=O)2
CAS Number:
Molecular Weight:
164.20
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

assay

98%

form

solid

mp

54-58 °C (lit.)

functional group

ketone

SMILES string

CC(C)(C)C1=CC(=O)C=CC1=O

InChI

1S/C10H12O2/c1-10(2,3)8-6-7(11)4-5-9(8)12/h4-6H,1-3H3

InChI key

NCCTVAJNFXYWTM-UHFFFAOYSA-N

General description

2-tert-Butyl-1,4-benzoquinone (TBQ, TBBQ, tBQ, BuBQ, BQ , tert-butyl-p-quinone) is a 1,4-benzoquinone derivative. It is a major metabolite of the food additive, butylated hydroxyanisole (BHA). TBQ is reported to be strongly cytotoxic in human monocytic leukemia U937 cells. TBQ is an oxidation product of 2-tert-butylhydroquinone (TBHQ). Studies confirm that TBQ induces apoptosis and cell proliferation inhibition in chronic myelogenous leukemia (CML) cells. Its binding interactions with lysozyme has been examined and found to be intermediate between BHA and TBHQ. It has been reported to be synthesized by the titanium superoxide catalyzed oxidation of 2-tert-butylphenol using aq. 30% H2O2. TBQ is one of the main neoformed compounds from TBHQ decomposition in PLA-TBHQ film (Poly lactic acid).

Application

2-tert-Butyl-1,4-benzoquinone may be used in the synthesis of azatrioxa[8]circulene.

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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Binding properties and structure-affinity relationships of food antioxidant butylated hydroxyanisole and its metabolites with lysozyme.
Wu D, et al.
Food Chemistry, 188, 370-376 (2015)
Titanium superoxide catalyzed selective oxidation of phenols to p-quinones with aq. H2O2.
Dewkar GK, et al.
Indian J. Chem. B, 44(7), 1530-1530 (2005)
W H Kalus et al.
Environmental health perspectives, 102(1), 96-99 (1994-01-01)
We examined t-butylhydroquinone (t-BHQ) and t-butylquinone (t-BuQ), two of the major microsomal metabolites of the synthetic antioxidant butylated hydroxyanisole (BHA), for their ability to react with the xenobiotic arylamines aniline and N-methylaniline. A number of substances were isolated by thin-layer
R Kahl et al.
Toxicology, 59(2), 179-194 (1989-12-01)
The synthetic antioxidant butylated hydroxyanisole (BHA) stimulates superoxide formation in rat liver microsomes up to 10-fold. This stimulation is prevented by the monooxygenase inhibitor metyrapone and does not occur when NADH is consumed instead of NADPH indicating that metabolic activation
M Mizuno et al.
Mutation research, 176(2), 179-184 (1987-02-01)
The reaction products from butylated hydroxyanisole treated with nitrite under acidic conditions were investigated for mutagenic activity in Salmonella typhimurium his reversion assay and for DNA-damaging activity using H17 Rec+ (wild) and M45 Rec- (recombinationless) of Bacillus subtilis. The chloroform

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