U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of TERT-BUTYLHYDROQUINONE

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

HIDE SMILES / InChI

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

Targets

Targets

Primary TargetPharmacologyConditionPotency
PubMed

PubMed

TitleDatePubMed
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
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
Stabilization of Nrf2 by tBHQ confers protection against oxidative stress-induced cell death in human neural stem cells.
2005-02
Coordinate regulation of glutathione metabolism in astrocytes by Nrf2.
2005-01-14
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
Differential regulation of three genes encoding glutathione S-transferases in Schizosaccharomyces pombe.
2004-12-31
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
Patents
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:02:29 GMT 2025
Edited
by admin
on Mon Mar 31 18:02:29 GMT 2025
Record UNII
C12674942B
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TERT-BUTYLHYDROQUINONE
II  
Systematic Name English
TBHQ
FCC   INCI  
INCI  
Preferred Name English
2-TERT-BUTYLHYDROQUINONE
Systematic Name English
E-319
Code English
HYDROQUINONE,TERTIARY BUTYL [VANDF]
Common Name English
TERT-BUTYLHYDROQUINONE [II]
Common Name English
INS-319
Code English
BUTYLHYDROQUINONE, TERT-
Systematic Name English
MONO-TERT-BUTYLHYDROQUINONE
Systematic Name English
TERTIARY BUTYLHYDROQUINONE
MART.  
Common Name English
2-(1,1-DIMETHYLETHYL)-1,4-BENZENEDIOL
Systematic Name English
BUTYLHYDROQUINONE,TERT-
Common Name English
INS NO.319
Code English
HYDROQUINONE,TERTIARY BUTYL
VANDF  
Common Name English
T-BUTYLHYDROQUINONE
HSDB  
Systematic Name English
SUSTANE
Brand Name English
MONO-TERTIARYBUTYLHYDROQUINONE
Common Name English
1,4-BENZENEDIOL, 2-(1,1-DIMETHYLETHYL)-
Systematic Name English
TERTIARY BUTYLHYDROQUINONE [MART.]
Common Name English
TBHQ [FCC]
Common Name English
T-BUTYLHYDROQUINONE [HSDB]
Common Name English
NSC-4972
Code English
Classification Tree Code System Code
CODEX ALIMENTARIUS (GSFA) INS-319
Created by admin on Mon Mar 31 18:02:29 GMT 2025 , Edited by admin on Mon Mar 31 18:02:29 GMT 2025
JECFA EVALUATION INS-319
Created by admin on Mon Mar 31 18:02:29 GMT 2025 , Edited by admin on Mon Mar 31 18:02:29 GMT 2025
Code System Code Type Description
CFR
21 CFR 172.185
Created by admin on Mon Mar 31 18:02:29 GMT 2025 , Edited by admin on Mon Mar 31 18:02:29 GMT 2025
PRIMARY
EPA CompTox
DTXSID6020220
Created by admin on Mon Mar 31 18:02:29 GMT 2025 , Edited by admin on Mon Mar 31 18:02:29 GMT 2025
PRIMARY
EVMPD
SUB169773
Created by admin on Mon Mar 31 18:02:29 GMT 2025 , Edited by admin on Mon Mar 31 18:02:29 GMT 2025
PRIMARY
RXCUI
1362739
Created by admin on Mon Mar 31 18:02:29 GMT 2025 , Edited by admin on Mon Mar 31 18:02:29 GMT 2025
PRIMARY
MESH
C018855
Created by admin on Mon Mar 31 18:02:29 GMT 2025 , Edited by admin on Mon Mar 31 18:02:29 GMT 2025
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DAILYMED
C12674942B
Created by admin on Mon Mar 31 18:02:29 GMT 2025 , Edited by admin on Mon Mar 31 18:02:29 GMT 2025
PRIMARY
CHEBI
78886
Created by admin on Mon Mar 31 18:02:29 GMT 2025 , Edited by admin on Mon Mar 31 18:02:29 GMT 2025
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NCI_THESAURUS
C77508
Created by admin on Mon Mar 31 18:02:29 GMT 2025 , Edited by admin on Mon Mar 31 18:02:29 GMT 2025
PRIMARY
WIKIPEDIA
TERT-BUTYLHYDROQUINONE
Created by admin on Mon Mar 31 18:02:29 GMT 2025 , Edited by admin on Mon Mar 31 18:02:29 GMT 2025
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SMS_ID
100000159541
Created by admin on Mon Mar 31 18:02:29 GMT 2025 , Edited by admin on Mon Mar 31 18:02:29 GMT 2025
PRIMARY
NSC
4972
Created by admin on Mon Mar 31 18:02:29 GMT 2025 , Edited by admin on Mon Mar 31 18:02:29 GMT 2025
PRIMARY
FDA UNII
C12674942B
Created by admin on Mon Mar 31 18:02:29 GMT 2025 , Edited by admin on Mon Mar 31 18:02:29 GMT 2025
PRIMARY
NCI_THESAURUS
C45678
Created by admin on Mon Mar 31 18:02:29 GMT 2025 , Edited by admin on Mon Mar 31 18:02:29 GMT 2025
CONCEPT Industrial Aid
PUBCHEM
16043
Created by admin on Mon Mar 31 18:02:29 GMT 2025 , Edited by admin on Mon Mar 31 18:02:29 GMT 2025
PRIMARY
ECHA (EC/EINECS)
217-752-2
Created by admin on Mon Mar 31 18:02:29 GMT 2025 , Edited by admin on Mon Mar 31 18:02:29 GMT 2025
PRIMARY
CAS
1948-33-0
Created by admin on Mon Mar 31 18:02:29 GMT 2025 , Edited by admin on Mon Mar 31 18:02:29 GMT 2025
PRIMARY
DRUG BANK
DB07726
Created by admin on Mon Mar 31 18:02:29 GMT 2025 , Edited by admin on Mon Mar 31 18:02:29 GMT 2025
PRIMARY
HSDB
838
Created by admin on Mon Mar 31 18:02:29 GMT 2025 , Edited by admin on Mon Mar 31 18:02:29 GMT 2025
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