TERT-BUTYLHYDROQUINONE

Relevant Data

Food Additives Approved by WHO:

Food Additives Approved by European Union:

  • Tertiary-butyl hydroquinone (TBHQ) [show]

General Information

MaintermTERT-BUTYLHYDROQUINONE
Doc TypeASP
CAS Reg.No.(or other ID)1948-33-0
Regnum 177.2420
172.185

From www.fda.gov

Computed Descriptors

Download SDF
2D Structure
CID16043
IUPAC Name2-tert-butylbenzene-1,4-diol
InChIInChI=1S/C10H14O2/c1-10(2,3)8-6-7(11)4-5-9(8)12/h4-6,11-12H,1-3H3
InChI KeyBGNXCDMCOKJUMV-UHFFFAOYSA-N
Canonical SMILESCC(C)(C)C1=C(C=CC(=C1)O)O
Molecular FormulaC10H14O2
Wikipediatert-butylhydroquinone

From Pubchem

Computed Properties

Property Name Property Value
Molecular Weight166.22
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count2
Rotatable Bond Count1
Complexity148.0
CACTVS Substructure Key Fingerprint A A A D c c B w M A A A A A A A A A A A A A A A A A A A A A A A A A A w A A A A A A A A A A A B A A A A G g A A C A A A D g S A m A A y B o A A A g C A A i B C A A A C A A A g I A A I i A A G C I g I J i K C E R K A c A A k w B E I m A f A w P A P g Q A B A A A I A A A C A A I A A B A A A A A A A A A A A A = =
Topological Polar Surface Area40.5
Monoisotopic Mass166.099
Exact Mass166.099
Compound Is CanonicalizedTrue
Formal Charge0
Heavy Atom Count12
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

From Pubchem

ADMET Predicted Profile --- Classification

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.7813
Human Intestinal AbsorptionHIA+0.9939
Caco-2 PermeabilityCaco2+0.8959
P-glycoprotein SubstrateNon-substrate0.6116
P-glycoprotein InhibitorNon-inhibitor0.9294
Non-inhibitor0.9743
Renal Organic Cation TransporterNon-inhibitor0.9171
Distribution
Subcellular localizationMitochondria0.8945
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7721
CYP450 2D6 SubstrateNon-substrate0.5661
CYP450 3A4 SubstrateSubstrate0.5162
CYP450 1A2 InhibitorInhibitor0.6786
CYP450 2C9 InhibitorNon-inhibitor0.8403
CYP450 2D6 InhibitorNon-inhibitor0.9232
CYP450 2C19 InhibitorNon-inhibitor0.9025
CYP450 3A4 InhibitorNon-inhibitor0.8310
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.6222
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9575
Non-inhibitor0.9131
AMES ToxicityNon AMES toxic0.9609
CarcinogensNon-carcinogens0.6888
Fish ToxicityHigh FHMT0.6100
Tetrahymena Pyriformis ToxicityHigh TPT0.8650
Honey Bee ToxicityHigh HBT0.7992
BiodegradationNot ready biodegradable0.9522
Acute Oral ToxicityIII0.8484
Carcinogenicity (Three-class)Non-required0.7226

From admetSAR

ADMET Predicted Profile --- Regression

Model Value Unit
Absorption
Aqueous solubility-2.3538LogS
Caco-2 Permeability1.6504LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity1.8796LD50, mol/kg
Fish Toxicity0.4272pLC50, mg/L
Tetrahymena Pyriformis Toxicity2.0087pIGC50, ug/L

From admetSAR

Toxicity Profile

Route of Exposure
Mechanism of Toxicity
Metabolism
Toxicity Values
Lethal Dose
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Minimum Risk Level
Health Effects
Treatment
Reference
  1. Hsu SS, Chou CT: Deltamethrin-Induced [Ca (2)(+) ]i Rise and Death in HGB Human Glioblastoma Cells. Chin J Physiol. 2012 Aug 31;55(4):294-304. doi: 10.4077/CJP.2012.BAB114.[23282171 ]
  2. Stolze K, Nohl H: Free radical formation and erythrocyte membrane alterations during MetHb formation induced by the BHA metabolite, tert-butylhydroquinone. Free Radic Res. 1999 Apr;30(4):295-303.[10230808 ]
  3. Gunaseelan K, Romsted LS, Gonzalez-Romero E, Bravo-Diaz C: Determining partition constants of polar organic molecules between the oil/interfacial and water/interfacial regions in emulsions: a combined electrochemical and spectrometric method. Langmuir. 2004 Apr 13;20(8):3047-55.[15875828 ]
  4. Surak JG: Monotertiarybutylhydroquinone effects on Tetrahymena pyriformis. Life Sci. 1977 May 15;20(10):1735-40.[406489 ]
  5. Astill BD, Terhaar CJ, Krasavage WJ, Wlof GL, Roudabush RL, Fassett DW: Safety evaluation and biochemical behavior of monotertiarybutylhydroquinone. J Am Oil Chem Soc. 1975 Feb;52(2):53-8.[1133430 ]

From T3DB

Taxonomic Classification

KingdomOrganic compounds
SuperclassBenzenoids
ClassBenzene and substituted derivatives
SubclassPhenylpropanes
Intermediate Tree NodesNot available
Direct ParentPhenylpropanes
Alternative Parents
Molecular FrameworkAromatic homomonocyclic compounds
SubstituentsPhenylpropane - Hydroquinone - 1-hydroxy-2-unsubstituted benzenoid - Phenol - Organic oxygen compound - Hydrocarbon derivative - Organooxygen compound - Aromatic homomonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety.

From ClassyFire

Targets

Target Details

Mothers against decapentaplegic homolog 1

General Function:
Transforming growth factor beta receptor, pathway-specific cytoplasmic mediator activity
Specific Function:
Transcriptional modulator activated by BMP (bone morphogenetic proteins) type 1 receptor kinase. SMAD1 is a receptor-regulated SMAD (R-SMAD). SMAD1/OAZ1/PSMB4 complex mediates the degradation of the CREBBP/EP300 repressor SNIP1. May act synergistically with SMAD4 and YY1 in bone morphogenetic protein (BMP)-mediated cardiac-specific gene expression.
Gene Name:
SMAD1
Uniprot ID:
Q15797
Molecular Weight:
52259.72 Da
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
Target Details

Cytochrome P450 2C9

General Function:
Steroid hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular Weight:
55627.365 Da
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
Target Details

Cytochrome P450 2C19

General Function:
Steroid hydroxylase activity
Specific Function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular Weight:
55930.545 Da
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
Target Details

Aryl hydrocarbon receptor

General Function:
Transcription regulatory region dna binding
Specific Function:
Ligand-activated transcriptional activator. Binds to the XRE promoter region of genes it activates. Activates the expression of multiple phase I and II xenobiotic chemical metabolizing enzyme genes (such as the CYP1A1 gene). Mediates biochemical and toxic effects of halogenated aromatic hydrocarbons. Involved in cell-cycle regulation. Likely to play an important role in the development and maturation of many tissues. Regulates the circadian clock by inhibiting the basal and circadian expression of the core circadian component PER1. Inhibits PER1 by repressing the CLOCK-ARNTL/BMAL1 heterodimer mediated transcriptional activation of PER1.
Gene Name:
AHR
Uniprot ID:
P35869
Molecular Weight:
96146.705 Da
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
Target Details

Nuclear receptor subfamily 1 group I member 2

General Function:
Zinc ion binding
Specific Function:
Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism and secretion of potentially harmful xenobiotics, drugs and endogenous compounds. Activated by the antibiotic rifampicin and various plant metabolites, such as hyperforin, guggulipid, colupulone, and isoflavones. Response to specific ligands is species-specific. Activated by naturally occurring steroids, such as pregnenolone and progesterone. Binds to a response element in the promoters of the CYP3A4 and ABCB1/MDR1 genes.
Gene Name:
NR1I2
Uniprot ID:
O75469
Molecular Weight:
49761.245 Da
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
Target Details

Cytochrome P450 2D6

General Function:
Steroid hydroxylase activity
Specific Function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular Weight:
55768.94 Da
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
Target Details

Nuclear receptor subfamily 1 group I member 3

General Function:
Zinc ion binding
Specific Function:
Binds and transactivates the retinoic acid response elements that control expression of the retinoic acid receptor beta 2 and alcohol dehydrogenase 3 genes. Transactivates both the phenobarbital responsive element module of the human CYP2B6 gene and the CYP3A4 xenobiotic response element.
Gene Name:
NR1I3
Uniprot ID:
Q14994
Molecular Weight:
39942.145 Da
References
  1. Dring AM, Anderson LE, Qamar S, Stoner MA: Rational quantitative structure-activity relationship (RQSAR) screen for PXR and CAR isoform-specific nuclear receptor ligands. Chem Biol Interact. 2010 Dec 5;188(3):512-25. doi: 10.1016/j.cbi.2010.09.018. Epub 2010 Oct 20. [20869355 ]

From T3DB