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
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
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
Chemoprevention of heterocyclic amine-induced carcinogenesis by phenolic compounds in rats.
1999 Sep 1
Inducers of gamma-glutamylcysteine synthetase and their effects on glutathione synthetase expression.
2000 Sep 7
Synthesis and antiperoxidant activity of new phenolic O-glycosides.
2001 Feb 28
2,5-Di-tert-butyl-1,4-hydroquinone enhances cell transformation accompanied by an increase in intracellular free calcium ion concentration.
2001 Jul 26
Reactive oxygen species-related induction of multidrug resistance-associated protein 2 expression in primary hepatocytes exposed to sulforaphane.
2001 Mar 23
Cell-based studies reveal differences in glutathione S-transferase induction between oltipraz and tert-butylhydroquinone.
2002
Characterization, quantification, and bioactivities of anthocyanins in Cornus species.
2002 Apr 24
Ability of surfactant micelles to alter the partitioning of phenolic antioxidants in oil-in-water emulsions.
2002 Feb 27
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
Differential gene expression patterns revealed by oligonucleotide versus long cDNA arrays.
2002 Oct
Role of AP-1 in the coordinate induction of rat glutamate-cysteine ligase and glutathione synthetase by tert-butylhydroquinone.
2002 Sep 20
Aqueous outflow-enhancing effect of tert-butylhydroquinone: involvement of AP-1 activation and MMP-3 expression.
2003 Aug
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
A reassessment of the effects of luminal [Ca2+] on inositol 1,4,5-trisphosphate-induced Ca2+ release from internal stores.
2003 Oct 10
Thioredoxin reductase in human hepatoma cells is transcriptionally regulated by sulforaphane and other electrophiles via an antioxidant response element.
2003 Sep
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
The induction of human UDP-glucuronosyltransferase 1A1 mediated through a distal enhancer module by flavonoids and xenobiotics.
2004 Mar 1
Patents
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
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EPA CompTox
DTXSID6020220
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EVMPD
SUB169773
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RXCUI
1362739
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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
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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
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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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