Details
Stereochemistry | ACHIRAL |
Molecular Formula | C10H14O2 |
Molecular Weight | 166.217 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)(C)C1=C(O)C=CC(O)=C1
InChI
InChIKey=BGNXCDMCOKJUMV-UHFFFAOYSA-N
InChI=1S/C10H14O2/c1-10(2,3)8-6-7(11)4-5-9(8)12/h4-6,11-12H,1-3H3
Tert-butylhydroquinone (tBHQ) or 2-(1,1-dimethylethyl)-1,4-benzenediol is an antioxdant found to inhibit lipid oxidation. Extensive studies have demonstrated that tBHQ exhibit anti-carcinogenic effect. The ability of tBHQ to induce phase II xenobiotic metabolizing enzymes through an Nrf2-dependent pathway is thought to be responsible for the observed protective effect of tBHQ. It has been proposed that tBHQ enhances Nrf2-mediated transcription by promoting reactive oxygen species-mediated dissociation of Nrf2-Keap1, Nrf2 stabilization, phosphatidylinositol 3-kinase (PI3K)/Akt activity, and MAPK pathway activation. tBHQ has been commonly used as a synthetic food additive to prevent oils and fats from oxidative deterioration and rancidity due to its potent anti-lipid peroxidation activity.
Approval Year
PubMed
Title | Date | PubMed |
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Induction of human UDP glucuronosyltransferases (UGT1A6, UGT1A9, and UGT2B7) by t-butylhydroquinone and 2,3,7,8-tetrachlorodibenzo-p-dioxin in Caco-2 cells. | 1999 May |
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Chemoprevention of heterocyclic amine-induced carcinogenesis by phenolic compounds in rats. | 1999 Sep 1 |
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Inducers of gamma-glutamylcysteine synthetase and their effects on glutathione synthetase expression. | 2000 Sep 7 |
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Synthesis and antiperoxidant activity of new phenolic O-glycosides. | 2001 Feb 28 |
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2,5-Di-tert-butyl-1,4-hydroquinone enhances cell transformation accompanied by an increase in intracellular free calcium ion concentration. | 2001 Jul 26 |
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Reactive oxygen species-related induction of multidrug resistance-associated protein 2 expression in primary hepatocytes exposed to sulforaphane. | 2001 Mar 23 |
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Cell-based studies reveal differences in glutathione S-transferase induction between oltipraz and tert-butylhydroquinone. | 2002 |
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Characterization, quantification, and bioactivities of anthocyanins in Cornus species. | 2002 Apr 24 |
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Ability of surfactant micelles to alter the partitioning of phenolic antioxidants in oil-in-water emulsions. | 2002 Feb 27 |
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Copper redox-dependent activation of 2-tert-butyl(1,4)hydroquinone: formation of reactive oxygen species and induction of oxidative DNA damage in isolated DNA and cultured rat hepatocytes. | 2002 Jul 25 |
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Differential gene expression patterns revealed by oligonucleotide versus long cDNA arrays. | 2002 Oct |
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Role of AP-1 in the coordinate induction of rat glutamate-cysteine ligase and glutathione synthetase by tert-butylhydroquinone. | 2002 Sep 20 |
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Aqueous outflow-enhancing effect of tert-butylhydroquinone: involvement of AP-1 activation and MMP-3 expression. | 2003 Aug |
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Phosphorylation of Nrf2 at Ser40 by protein kinase C in response to antioxidants leads to the release of Nrf2 from INrf2, but is not required for Nrf2 stabilization/accumulation in the nucleus and transcriptional activation of antioxidant response element-mediated NAD(P)H:quinone oxidoreductase-1 gene expression. | 2003 Nov 7 |
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A reassessment of the effects of luminal [Ca2+] on inositol 1,4,5-trisphosphate-induced Ca2+ release from internal stores. | 2003 Oct 10 |
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Thioredoxin reductase in human hepatoma cells is transcriptionally regulated by sulforaphane and other electrophiles via an antioxidant response element. | 2003 Sep |
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Nuclear factor E2-related factor 2-dependent antioxidant response element activation by tert-butylhydroquinone and sulforaphane occurring preferentially in astrocytes conditions neurons against oxidative insult. | 2004 Feb 4 |
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The induction of human UDP-glucuronosyltransferase 1A1 mediated through a distal enhancer module by flavonoids and xenobiotics. | 2004 Mar 1 |
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Classification Tree | Code System | Code | ||
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CODEX ALIMENTARIUS (GSFA) |
INS-319
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JECFA EVALUATION |
INS-319
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21 CFR 172.185
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DTXSID6020220
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SUB169773
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1362739
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C018855
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C12674942B
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78886
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C77508
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TERT-BUTYLHYDROQUINONE
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100000159541
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4972
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C12674942B
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C45678
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16043
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217-752-2
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1948-33-0
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DB07726
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838
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SUBSTANCE RECORD