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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
Recommended Products
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.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
Target Organs
Respiratory system
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
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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Titanium superoxide catalyzed selective oxidation of phenols to p-quinones with aq. H2O2.
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Indian J. Chem. B, 44(7), 1530-1530 (2005)
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)
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
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
Azatrioxa [8] circulenes: Planar Anti-Aromatic Cyclooctatetraenes.
Nielsen CB, et al.
Chemistry (Weinheim An Der Bergstrasse, Germany), 19(12), 3898-3904 (2013)
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