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=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

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
Inducers of gamma-glutamylcysteine synthetase and their effects on glutathione synthetase expression.
2000 Sep 7
A novel function of sphingosine-1-phosphate to activate a non-selective cation channel in human endothelial cells.
2001 Dec 1
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
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
Identification of alpha-tocopherol oxidation products in triolein at elevated temperatures.
2001 Mar
Troglitazone selectively inhibits glyoxalase I gene expression.
2001 Nov
Cyclooxygenase inhibitory and antioxidant cyanidin glycosides in cherries and berries.
2001 Sep
Time-dependent changes in ARE-driven gene expression by use of a noise-filtering process for microarray data.
2002
Influence of redox-active compounds and PXR-activators on human MRP1 and MRP2 gene expression.
2002 Feb 28
Differential induction of mafF, mafG and mafK expression by electrophile-response-element activators.
2002 Jan 15
In vitro induction of the anticarcinogenic marker enzyme, quinone reductase, in human hepatoma cells by food extracts.
2002 Jun 6
Phosphatidylinositol 3-kinase regulates nuclear translocation of NF-E2-related factor 2 through actin rearrangement in response to oxidative stress.
2002 Nov
Differential responses from seven mammalian cell lines to the treatments of detoxifying enzyme inducers.
2003 Apr 4
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
Patch testing with the irritant sodium lauryl sulfate (SLS) is useful in interpreting weak reactions to contact allergens as allergic or irritant.
2003 Feb
Cell death induced by the phenolic antioxidant tert-butylhydroquinone and its metabolite tert-butylquinone in human monocytic leukemia U937 cells.
2003 May
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
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
Thioredoxin reductase in human hepatoma cells is transcriptionally regulated by sulforaphane and other electrophiles via an antioxidant response element.
2003 Sep
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
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
Differential regulation of three genes encoding glutathione S-transferases in Schizosaccharomyces pombe.
2004 Dec 31
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
Down-regulation of aryl hydrocarbon receptor-regulated genes by tumor necrosis factor-alpha and lipopolysaccharide in murine hepatoma Hepa 1c1c7 cells.
2005 Mar
Different cytoprotective effect of antioxidants and change in the iron regulatory system in rodent cells exposed to paraquat or formaldehyde.
2005 Mar 1
Transcriptional activation of the human Galphai2 gene promoter through nuclear factor-kappaB and antioxidant response elements.
2005 Mar 18
Dissecting tBHQ induced ARE-driven gene expression through long and short oligonucleotide arrays.
2005 Mar 21
Patents
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:35:58 GMT 2023
Edited
by admin
on Fri Dec 15 15:35:58 GMT 2023
Record UNII
C12674942B
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TERT-BUTYLHYDROQUINONE
II  
Systematic 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
TBHQ [INCI]
Common 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
TBHQ
FCC   INCI  
INCI  
Official 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 Fri Dec 15 15:35:58 GMT 2023 , Edited by admin on Fri Dec 15 15:35:58 GMT 2023
JECFA EVALUATION INS-319
Created by admin on Fri Dec 15 15:35:58 GMT 2023 , Edited by admin on Fri Dec 15 15:35:58 GMT 2023
Code System Code Type Description
CFR
21 CFR 172.185
Created by admin on Fri Dec 15 15:35:58 GMT 2023 , Edited by admin on Fri Dec 15 15:35:58 GMT 2023
PRIMARY
EPA CompTox
DTXSID6020220
Created by admin on Fri Dec 15 15:35:58 GMT 2023 , Edited by admin on Fri Dec 15 15:35:58 GMT 2023
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EVMPD
SUB169773
Created by admin on Fri Dec 15 15:35:58 GMT 2023 , Edited by admin on Fri Dec 15 15:35:58 GMT 2023
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RXCUI
1362739
Created by admin on Fri Dec 15 15:35:58 GMT 2023 , Edited by admin on Fri Dec 15 15:35:58 GMT 2023
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MESH
C018855
Created by admin on Fri Dec 15 15:35:58 GMT 2023 , Edited by admin on Fri Dec 15 15:35:58 GMT 2023
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DAILYMED
C12674942B
Created by admin on Fri Dec 15 15:35:58 GMT 2023 , Edited by admin on Fri Dec 15 15:35:58 GMT 2023
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CHEBI
78886
Created by admin on Fri Dec 15 15:35:58 GMT 2023 , Edited by admin on Fri Dec 15 15:35:58 GMT 2023
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NCI_THESAURUS
C77508
Created by admin on Fri Dec 15 15:35:58 GMT 2023 , Edited by admin on Fri Dec 15 15:35:58 GMT 2023
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WIKIPEDIA
TERT-BUTYLHYDROQUINONE
Created by admin on Fri Dec 15 15:35:58 GMT 2023 , Edited by admin on Fri Dec 15 15:35:58 GMT 2023
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SMS_ID
100000159541
Created by admin on Fri Dec 15 15:35:58 GMT 2023 , Edited by admin on Fri Dec 15 15:35:58 GMT 2023
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NSC
4972
Created by admin on Fri Dec 15 15:35:58 GMT 2023 , Edited by admin on Fri Dec 15 15:35:58 GMT 2023
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FDA UNII
C12674942B
Created by admin on Fri Dec 15 15:35:58 GMT 2023 , Edited by admin on Fri Dec 15 15:35:58 GMT 2023
PRIMARY
NCI_THESAURUS
C45678
Created by admin on Fri Dec 15 15:35:58 GMT 2023 , Edited by admin on Fri Dec 15 15:35:58 GMT 2023
CONCEPT Industrial Aid
PUBCHEM
16043
Created by admin on Fri Dec 15 15:35:58 GMT 2023 , Edited by admin on Fri Dec 15 15:35:58 GMT 2023
PRIMARY
ECHA (EC/EINECS)
217-752-2
Created by admin on Fri Dec 15 15:35:58 GMT 2023 , Edited by admin on Fri Dec 15 15:35:58 GMT 2023
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CAS
1948-33-0
Created by admin on Fri Dec 15 15:35:58 GMT 2023 , Edited by admin on Fri Dec 15 15:35:58 GMT 2023
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DRUG BANK
DB07726
Created by admin on Fri Dec 15 15:35:58 GMT 2023 , Edited by admin on Fri Dec 15 15:35:58 GMT 2023
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HSDB
838
Created by admin on Fri Dec 15 15:35:58 GMT 2023 , Edited by admin on Fri Dec 15 15:35:58 GMT 2023
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