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
Molecular Formula | C10H14O2 |
Molecular Weight | 166.217 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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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Inducers of gamma-glutamylcysteine synthetase and their effects on glutathione synthetase expression. | 2000 Sep 7 |
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A novel function of sphingosine-1-phosphate to activate a non-selective cation channel in human endothelial cells. | 2001 Dec 1 |
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Nrf2-dependent activation of the antioxidant responsive element by tert-butylhydroquinone is independent of oxidative stress in IMR-32 human neuroblastoma cells. | 2001 Jan 12 |
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Functional characterization and role of INrf2 in antioxidant response element-mediated expression and antioxidant induction of NAD(P)H:quinone oxidoreductase1 gene. | 2001 Jun 28 |
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Identification of alpha-tocopherol oxidation products in triolein at elevated temperatures. | 2001 Mar |
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Troglitazone selectively inhibits glyoxalase I gene expression. | 2001 Nov |
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Cyclooxygenase inhibitory and antioxidant cyanidin glycosides in cherries and berries. | 2001 Sep |
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Time-dependent changes in ARE-driven gene expression by use of a noise-filtering process for microarray data. | 2002 |
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Influence of redox-active compounds and PXR-activators on human MRP1 and MRP2 gene expression. | 2002 Feb 28 |
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Differential induction of mafF, mafG and mafK expression by electrophile-response-element activators. | 2002 Jan 15 |
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In vitro induction of the anticarcinogenic marker enzyme, quinone reductase, in human hepatoma cells by food extracts. | 2002 Jun 6 |
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Phosphatidylinositol 3-kinase regulates nuclear translocation of NF-E2-related factor 2 through actin rearrangement in response to oxidative stress. | 2002 Nov |
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Differential responses from seven mammalian cell lines to the treatments of detoxifying enzyme inducers. | 2003 Apr 4 |
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Identification of the NF-E2-related factor-2-dependent genes conferring protection against oxidative stress in primary cortical astrocytes using oligonucleotide microarray analysis. | 2003 Apr 4 |
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Patch testing with the irritant sodium lauryl sulfate (SLS) is useful in interpreting weak reactions to contact allergens as allergic or irritant. | 2003 Feb |
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Cell death induced by the phenolic antioxidant tert-butylhydroquinone and its metabolite tert-butylquinone in human monocytic leukemia U937 cells. | 2003 May |
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Increase of antioxidative potential by tert-butylhydroquinone protects against cell death associated with 6-hydroxydopamine-induced oxidative stress in neuroblastoma SH-SY5Y cells. | 2003 Nov 26 |
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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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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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Total phenolics and antioxidant activities of fenugreek, green tea, black tea, grape seed, ginger, rosemary, gotu kola, and ginkgo extracts, vitamin E, and tert-butylhydroquinone. | 2004 Aug 11 |
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Effect of electron beam irradiation and storage at 5 degrees C on thiobarbituric acid reactive substances and carbonyl contents in chicken breast meat infused with antioxidants and selected plant extracts. | 2004 Dec 29 |
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Differential regulation of three genes encoding glutathione S-transferases in Schizosaccharomyces pombe. | 2004 Dec 31 |
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Identification of benzene metabolites in dermal fibroblasts as nonphenolic: regulation of cell viability, apoptosis, lipid peroxidation and expression of matrix metalloproteinase 1 and elastin by benzene metabolites. | 2004 May-Jun |
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Down-regulation of aryl hydrocarbon receptor-regulated genes by tumor necrosis factor-alpha and lipopolysaccharide in murine hepatoma Hepa 1c1c7 cells. | 2005 Mar |
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Different cytoprotective effect of antioxidants and change in the iron regulatory system in rodent cells exposed to paraquat or formaldehyde. | 2005 Mar 1 |
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Transcriptional activation of the human Galphai2 gene promoter through nuclear factor-kappaB and antioxidant response elements. | 2005 Mar 18 |
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Dissecting tBHQ induced ARE-driven gene expression through long and short oligonucleotide arrays. | 2005 Mar 21 |
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:35:58 GMT 2023
by
admin
on
Fri Dec 15 15:35:58 GMT 2023
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Record UNII |
C12674942B
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Record Status |
Validated (UNII)
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Record Version |
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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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