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429074

Sigma-Aldrich

2-tert-Butyl-1,4-benzoquinone

98%

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About This Item

Fórmula lineal:
(CH3)3CC6H3(=O)2
Número de CAS:
3602-55-9
Peso molecular:
164.20
EC Number:
222-757-8
MDL number:
MFCD00666928
UNSPSC Code:
12352100
PubChem Substance ID:
24866835
NACRES:
NA.22

assay

98%

form

solid

mp

54-58 °C (lit.)

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
GHS07

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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P A Schilderman et al.
Carcinogenesis, 16(3), 507-512 (1995-03-01)
The food additive butylated hydroxyanisole (BHA) has been shown to induce gastrointestinal hyperplasia in rodents by an unknown mechanism. The relevance of this observation for human risk assessment is not clear. We therefore analysed the effect of BHA and its
Azatrioxa [8] circulenes: Planar Anti-Aromatic Cyclooctatetraenes.
Nielsen CB, et al.
Chemistry (Weinheim An Der Bergstrasse, Germany), 19(12), 3898-3904 (2013)
Release of synthetic phenolic antioxidants from extruded poly lactic acid (PLA) film.
Jamshidian M, et al.
Food Control, 28(2), 445-455 (2012)
J H Chung et al.
Toxicology and applied pharmacology, 124(1), 123-130 (1994-01-01)
Quinone reductase (QR), in the presence of suitable substrate, results in the regeneration of NAD+ from NADH. To test the hypothesis that QR can play a role in ethanol metabolism and toxicity, we studied the effect of a quinone as
C G Rogers et al.
Mutation research, 299(1), 9-18 (1993-03-01)
tert.-Butyl-p-quinone (TBQ), a major metabolite of the phenolic antioxidant tert.-butyl-4-hydroxyanisole (BHA), was examined for cytotoxic and genotoxic properties in an in vitro assay system with Chinese hamster V79 cells and in diploid strain D7 of Saccharomyces cerevisiae. TBQ was prepared
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