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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:47:32 UTC
Update Date2023-02-21 17:21:35 UTC
HMDB IDHMDB0032062
Secondary Accession Numbers
  • HMDB32062
Metabolite Identification
Common Name2-tert-Butyl-1,4-benzenediol
Description2-tert-Butyl-1,4-benzenediol, also known as MTBHQ or 2-t-butylhydroquinone, belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety. Based on a literature review a small amount of articles have been published on 2-tert-Butyl-1,4-benzenediol.
Structure
Data?1677000095
Synonyms
ValueSource
2-(1,1-Dimethylethyl)-1,4-benzenediolChEBI
2-t-Butyl-1,4-benzenediolChEBI
2-t-ButylhydroquinoneChEBI
2-Tert-butyl(1,4)hydroquinoneChEBI
2-Tertiary-butylhydroquinoneChEBI
mono-Tert-butylhydroquinoneChEBI
mono-TertiarybutylhydroquinoneChEBI
MTBHQChEBI
t-Butyl hydroquinoneChEBI
t-ButylhydroquinoneChEBI
TBHQChEBI
Tert-butyl-1,4-benzenediolChEBI
Tert-butylhydroquinoneChEBI
Tertiary-butylhydroquinoneChEBI
2-(1,1-Dimethylethyl)-1,4-benzenediol, 9ciHMDB
2-(1,1-Dimethylethyl)benzene-1,4-diolHMDB
2-Tert-butylbenzene-1,4-diolHMDB
2-Tert-butylhydroquinoneHMDB
Banox 20baHMDB
Eastman MTBHQHMDB
EYKHMDB
Monotertiary butyl hydroquinoneHMDB
SustaneHMDB
Sustane TBHQHMDB
T-BHQHMDB
t-Butyl-hydroquinoneHMDB
Tenox 20HMDB
Tenox tbhoHMDB
Tenox TBHQHMDB
Tenox TBHQTBHQHMDB
Tert-butyl-hydroquinoneHMDB
Tert-butylhydrochinoneHMDB
2-Tert-butyl-1,4-benzenediolChEBI
Chemical FormulaC10H14O2
Average Molecular Weight166.217
Monoisotopic Molecular Weight166.099379692
IUPAC Name2-tert-butylbenzene-1,4-diol
Traditional Nametert-butylhydroquinone
CAS Registry Number1948-33-0
SMILES
CC(C)(C)C1=CC(O)=CC=C1O
InChI Identifier
InChI=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
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylpropanes
Direct ParentPhenylpropanes
Alternative Parents
Substituents
  • Phenylpropane
  • Hydroquinone
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point127 - 129 °CNot Available
Boiling Point291.35 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility748.2 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP2.257 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility2.75 g/LALOGPS
logP2.61ALOGPS
logP2.91ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)9.94ChemAxon
pKa (Strongest Basic)-5.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity48.69 m³·mol⁻¹ChemAxon
Polarizability18.38 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+137.6931661259
DarkChem[M-H]-135.61931661259
DeepCCS[M+H]+139.75530932474
DeepCCS[M-H]-137.33430932474
DeepCCS[M-2H]-173.31730932474
DeepCCS[M+Na]+148.53230932474
AllCCS[M+H]+132.732859911
AllCCS[M+H-H2O]+128.432859911
AllCCS[M+NH4]+136.832859911
AllCCS[M+Na]+138.032859911
AllCCS[M-H]-133.932859911
AllCCS[M+Na-2H]-135.032859911
AllCCS[M+HCOO]-136.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-tert-Butyl-1,4-benzenediolCC(C)(C)C1=CC(O)=CC=C1O2455.3Standard polar33892256
2-tert-Butyl-1,4-benzenediolCC(C)(C)C1=CC(O)=CC=C1O1462.9Standard non polar33892256
2-tert-Butyl-1,4-benzenediolCC(C)(C)C1=CC(O)=CC=C1O1567.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2-tert-Butyl-1,4-benzenediol,1TMS,isomer #1CC(C)(C)C1=CC(O[Si](C)(C)C)=CC=C1O1499.8Semi standard non polar33892256
2-tert-Butyl-1,4-benzenediol,1TMS,isomer #2CC(C)(C)C1=CC(O)=CC=C1O[Si](C)(C)C1576.7Semi standard non polar33892256
2-tert-Butyl-1,4-benzenediol,2TMS,isomer #1CC(C)(C)C1=CC(O[Si](C)(C)C)=CC=C1O[Si](C)(C)C1611.1Semi standard non polar33892256
2-tert-Butyl-1,4-benzenediol,1TBDMS,isomer #1CC(C)(C)C1=CC(O[Si](C)(C)C(C)(C)C)=CC=C1O1739.4Semi standard non polar33892256
2-tert-Butyl-1,4-benzenediol,1TBDMS,isomer #2CC(C)(C)C1=CC(O)=CC=C1O[Si](C)(C)C(C)(C)C1807.4Semi standard non polar33892256
2-tert-Butyl-1,4-benzenediol,2TBDMS,isomer #1CC(C)(C)C1=CC(O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C2086.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2-tert-Butyl-1,4-benzenediol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-2900000000-f1c81ea618f29937b9db2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-tert-Butyl-1,4-benzenediol GC-MS (2 TMS) - 70eV, Positivesplash10-0072-5290000000-a66d84718b6ad3740c7f2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-tert-Butyl-1,4-benzenediol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0fk9-3900000000-b2a502fc1214548205d42014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-tert-Butyl-1,4-benzenediol 10V, Positive-QTOFsplash10-014i-0900000000-c8c9ce2ba695603664e02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-tert-Butyl-1,4-benzenediol 20V, Positive-QTOFsplash10-02t9-1900000000-60b2cdcb6f62608be5622016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-tert-Butyl-1,4-benzenediol 40V, Positive-QTOFsplash10-0540-9600000000-c632f069846be5a5631e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-tert-Butyl-1,4-benzenediol 10V, Negative-QTOFsplash10-014i-0900000000-a87a87005aabcae88abb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-tert-Butyl-1,4-benzenediol 20V, Negative-QTOFsplash10-014i-0900000000-944286023e85118a003e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-tert-Butyl-1,4-benzenediol 40V, Negative-QTOFsplash10-0api-5900000000-0b55de568076ecc543d62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-tert-Butyl-1,4-benzenediol 10V, Positive-QTOFsplash10-066r-4900000000-4e458a1e12011a878c7f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-tert-Butyl-1,4-benzenediol 20V, Positive-QTOFsplash10-0a4i-9700000000-dbaf67fa3a2eadaf141b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-tert-Butyl-1,4-benzenediol 40V, Positive-QTOFsplash10-0a4i-9300000000-9a7c98eebcf85d0a06562021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-tert-Butyl-1,4-benzenediol 10V, Negative-QTOFsplash10-014i-0900000000-349584a3f625d5b5807f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-tert-Butyl-1,4-benzenediol 20V, Negative-QTOFsplash10-0159-5900000000-5a27aa1cd764288a4c772021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-tert-Butyl-1,4-benzenediol 40V, Negative-QTOFsplash10-0aos-9700000000-31963d7453ec788e62df2021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB07726
Phenol Explorer Compound IDNot Available
FooDB IDFDB008771
KNApSAcK IDNot Available
Chemspider ID15235
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTert-Butylhydroquinone
METLIN IDNot Available
PubChem Compound16043
PDB IDEYK
ChEBI ID78886
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1050641
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  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. [PubMed: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. [PubMed: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. [PubMed:15875828 ]
  4. Surak JG: Monotertiarybutylhydroquinone effects on Tetrahymena pyriformis. Life Sci. 1977 May 15;20(10):1735-40. [PubMed: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. [PubMed:1133430 ]
  6. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .