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=CC(O)=CC=C1O
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 |
|---|---|---|
| Dissecting tBHQ induced ARE-driven gene expression through long and short oligonucleotide arrays. | 2005-03-21 |
|
| Transcriptional activation of the human Galphai2 gene promoter through nuclear factor-kappaB and antioxidant response elements. | 2005-03-18 |
|
| Different cytoprotective effect of antioxidants and change in the iron regulatory system in rodent cells exposed to paraquat or formaldehyde. | 2005-03-01 |
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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. | 2005-03 |
|
| tert-Butylhydroquinone is a novel aryl hydrocarbon receptor ligand. | 2005-03 |
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| Stabilization of Nrf2 by tBHQ confers protection against oxidative stress-induced cell death in human neural stem cells. | 2005-02 |
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| Coordinate regulation of glutathione metabolism in astrocytes by Nrf2. | 2005-01-14 |
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| Potential neuroprotective effect of t-butylhydroquinone against neurotoxicity-induced by 1-methyl-4-(2'-methylphenyl)-1,2,3,6-tetrahydropyridine (2'-methyl-MPTP) in mice. | 2005 |
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| Differential regulation of three genes encoding glutathione S-transferases in Schizosaccharomyces pombe. | 2004-12-31 |
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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. | 2004-12-29 |
|
| Expression of glutathione S-transferase P1-1 in leukemic cells is regulated by inducible AP-1 binding. | 2004-12-28 |
|
| Nrf3 negatively regulates antioxidant-response element-mediated expression and antioxidant induction of NAD(P)H:quinone oxidoreductase1 gene. | 2004-12-03 |
|
| Phase II enzyme inducer, sulforaphane, inhibits UVB-induced AP-1 activation in human keratinocytes by a novel mechanism. | 2004-11 |
|
| Compartmentation of Nrf-2 redox control: regulation of cytoplasmic activation by glutathione and DNA binding by thioredoxin-1. | 2004-11 |
|
| Optimization of a high-performance liquid chromatography system by artificial neural networks for separation and determination of antioxidants. | 2004-10 |
|
| Ceramide, an apoptotic rheostat, inhibits CCAAT/enhancer binding protein-beta and NF-E2-related factor-2 activation: the role in glutathione S-transferase A2 gene repression. | 2004-09 |
|
| 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. | 2004-08-11 |
|
| Two pathways for store-mediated calcium entry differentially dependent on the actin cytoskeleton in human platelets. | 2004-07-09 |
|
| PKC downstream of Pl3-kinase regulates peroxynitrite formation for Nrf2-mediated GSTA2 induction. | 2004-07 |
|
| Induction of metallothionein I by phenolic antioxidants requires metal-activated transcription factor 1 (MTF-1) and zinc. | 2004-06-15 |
|
| Ceramide negatively regulates glutathione S-transferase gene transactivation via repression of hepatic nuclear factor-1 that is degraded by the ubiquitin proteasome system. | 2004-06 |
|
| The induction of human UDP-glucuronosyltransferase 1A1 mediated through a distal enhancer module by flavonoids and xenobiotics. | 2004-03-01 |
|
| Variable regulation of glutamate cysteine ligase subunit proteins affects glutathione biosynthesis in response to oxidative stress. | 2004-03-01 |
|
| 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. | 2004-02-04 |
|
| Induction of murine NAD(P)H:quinone oxidoreductase by 2,3,7,8-tetrachlorodibenzo-p-dioxin requires the CNC (cap 'n' collar) basic leucine zipper transcription factor Nrf2 (nuclear factor erythroid 2-related factor 2): cross-interaction between AhR (aryl hydrocarbon receptor) and Nrf2 signal transduction. | 2004-01-01 |
|
| Increase of antioxidative potential by tert-butylhydroquinone protects against cell death associated with 6-hydroxydopamine-induced oxidative stress in neuroblastoma SH-SY5Y cells. | 2003-11-26 |
|
| 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. | 2003-11-07 |
|
| A reassessment of the effects of luminal [Ca2+] on inositol 1,4,5-trisphosphate-induced Ca2+ release from internal stores. | 2003-10-10 |
|
| Contribution of the Ah receptor to the phenolic antioxidant-mediated expression of human and rat UDP-glucuronosyltransferase UGT1A6 in Caco-2 and rat hepatoma 5L cells. | 2003-09-01 |
|
| Thioredoxin reductase in human hepatoma cells is transcriptionally regulated by sulforaphane and other electrophiles via an antioxidant response element. | 2003-09 |
|
| 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. | 2003-08-10 |
|
| Aqueous outflow-enhancing effect of tert-butylhydroquinone: involvement of AP-1 activation and MMP-3 expression. | 2003-08 |
|
| Positive and negative regulation of prostaglandin E2 biosynthesis in human colorectal carcinoma cells by cancer chemopreventive agents. | 2003-07-01 |
|
| Testicular toxicity of dibromoacetonitrile and possible protection by tertiary butylhydroquinone. | 2003-06 |
|
| Thymoquinone is a potent superoxide anion scavenger. | 2003-05 |
|
| Cell death induced by the phenolic antioxidant tert-butylhydroquinone and its metabolite tert-butylquinone in human monocytic leukemia U937 cells. | 2003-05 |
|
| Antioxidant activity of 3-dehydroshikimic acid in liposomes, emulsions, and bulk oil. | 2003-04-23 |
|
| Coordinate regulation of glutathione biosynthesis and release by Nrf2-expressing glia potently protects neurons from oxidative stress. | 2003-04-15 |
|
| Pivotal role of electrophilicity in glutathione S-transferase induction by tert-butylhydroquinone. | 2003-04-15 |
|
| Enhancement of ATRA-induced cell differentiation by inhibition of calcium accumulation into the endoplasmic reticulum: cross-talk between RAR alpha and calcium-dependent signaling. | 2003-04-15 |
|
| Differential responses from seven mammalian cell lines to the treatments of detoxifying enzyme inducers. | 2003-04-04 |
|
| Identification of the NF-E2-related factor-2-dependent genes conferring protection against oxidative stress in primary cortical astrocytes using oligonucleotide microarray analysis. | 2003-04-04 |
|
| Hydrogen peroxide- and cell-density-regulated expression of NADH-cytochrome b5 reductase in HeLa cells. | 2003-04 |
|
| Thioredoxin-dependent redox regulation of the antioxidant responsive element (ARE) in electrophile response. | 2003-03-27 |
|
| Cyclooxygenase inhibitory and antioxidant compounds from crabapple fruits. | 2003-03-26 |
|
| Role of NAD(P)H:quinone oxidoreductase in the progression of neuronal cell death in vitro and following cerebral ischaemia in vivo. | 2003-03 |
|
| Increased protein stability as a mechanism that enhances Nrf2-mediated transcriptional activation of the antioxidant response element. Degradation of Nrf2 by the 26 S proteasome. | 2003-02-14 |
|
| Patch testing with the irritant sodium lauryl sulfate (SLS) is useful in interpreting weak reactions to contact allergens as allergic or irritant. | 2003-02 |
|
| Regulation of the glyoxalase pathway in human brain microvascular endothelium: effects of troglitazone and tertiary butylhydroperoxide. | 2002 |
|
| [Extraction of the antioxidative substances from Chinese rose and its antioxidative effect on lard]. | 2001-11 |
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:02:29 GMT 2025
by
admin
on
Mon Mar 31 18:02:29 GMT 2025
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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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C018855
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C12674942B
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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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