Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2012-09-11 18:36:03 UTC
Update Date2021-10-13 06:35:50 UTC
HMDB IDHMDB0033826
Secondary Accession Numbers
  • HMDB33826
Metabolite Identification
Common Name2,6-Di-tert-butyl-4-methylphenol
Description2,6-Di-tert-butyl-4-methylphenol, also known as butylated hydroxytoluene or BHT, belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety. BHT is a mild, camphor, and musty tasting compound. It has been detected, but not quantified, in soft-necked garlic. This could make BHT a potential biomarker for the consumption of this food. BHT is a synthetic phenolic antioxidant (SPA). SPAs are a family of chemicals used widely in foods, polymers, and cosmetics as radical trapping agents to slow down degradation due to oxidation. Given their widespread use, human exposure is unavoidable and there is public concern regarding environmental contamination by these chemicals. BHT was detected in human urine (PMID:31265952 ).
Structure
Data?1588090629
Synonyms
ValueSource
2,6-Bis(1,1-dimethylethyl)-4-methylphenolChEBI
2,6-Di-t-butyl-4-methylphenolChEBI
2,6-Di-tert-butyl-1-hydroxy-4-methylbenzeneChEBI
2,6-Di-tert-butyl-4-cresolChEBI
2,6-Di-tert-butyl-p-cresolChEBI
BHTChEBI
Butylated hydroxytolueneChEBI
ButylhydroxytolueneChEBI
2,6 Di t butyl 4 methylphenolMeSH
2,6 Di tert butyl 4 methylphenolMeSH
2,6 Di tert butyl p cresolMeSH
4 Methyl 2,6 ditertbutylphenolMeSH
4-Methyl-2,6-ditertbutylphenolMeSH
Di tert butyl methylphenolMeSH
DibunolMeSH
Hydroxytoluene, butylatedMeSH
IonolMeSH
Ionol (BHT)MeSH
Di-tert-butyl-methylphenolMeSH
2,6-Bis(1,1-dimethylethyl)-4-methylphenol, 9ciHMDB
2,6-Di-tert-butyl-P-cresol, 8ciHMDB
Butyl hydroxy tolueneHMDB
e321HMDB
FEMA 2184HMDB
PopolHMDB
2,6-Bis(tert-butyl)-4-methylphenolHMDB
2,6-Di(tert-butyl)hydroxytolueneHMDB
2,6-Di-tert-butyl-4-hydroxytolueneHMDB
2,6-Di-tert-butyl-4-methyl phenolHMDB
2,6-Di-tert-butyl-4-methyl-1-hydroxybenzeneHMDB
2,6-Di-tert-butyl-4-methylhydroxybenzeneHMDB
2,6-Di-tert-butyl-4-methylphenolHMDB
2,6-Di-tert-butyl-p-cresoleHMDB
2,6-Di-tert-butyl-p-methylphenolHMDB
2,6-Di-tert-butylcresolHMDB
2,6-Di-tert-butylmethylphenolHMDB
2,6-Ditertbutyl paracresolHMDB
2,6-tert-Butyl-4-methylphenolHMDB
3,5-Bis(1,1-dimethylethyl)-4-hydroxytolueneHMDB
3,5-Di-tert-butyl-4-hydroxytolueneHMDB
3,5-Di-tert-butyl-p-hydroxytolueneHMDB
4-Hydroxy-3,5-di-tert-butyltolueneHMDB
4-Methyl-2,6-bis(1,1-dimethylethyl)phenolHMDB
4-Methyl-2,6-di-tert-butylphenolHMDB
4-Methyl-2,6-ditertbutyl phenolHMDB
Di-tert-Butyl-4-methylphenolHMDB
Di-tert-butyl-p-cresolHMDB
Di-tert-butylcresolHMDB
Dibutyl paracresolHMDB
Dibutylated hydroxytolueneHMDB
DibutylcresolHMDB
DibutylhydroxytolueneHMDB
o-Di-tert-butyl-p-methylphenolHMDB
Chemical FormulaC15H24O
Average Molecular Weight220.3505
Monoisotopic Molecular Weight220.18271539
IUPAC Name2,6-di-tert-butyl-4-methylphenol
Traditional Nameional
CAS Registry Number128-37-0
SMILES
CC1=CC(=C(O)C(=C1)C(C)(C)C)C(C)(C)C
InChI Identifier
InChI=1S/C15H24O/c1-10-8-11(14(2,3)4)13(16)12(9-10)15(5,6)7/h8-9,16H,1-7H3
InChI KeyNLZUEZXRPGMBCV-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
  • P-cresol
  • Toluene
  • Phenol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point71 °CNot Available
Boiling Point265.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility0.0006 mg/mL at 25 °CNot Available
LogP5.10Not Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.015 g/LALOGPS
logP10(5.25) g/LALOGPS
logP10(5.27) g/LChemAxon
logS10(-4.2) g/LALOGPS
pKa (Strongest Acidic)11.6ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity70.41 m³·mol⁻¹ChemAxon
Polarizability27.35 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+151.86431661259
DarkChem[M-H]-152.36531661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2,6-Di-tert-butyl-4-methylphenol,1TMS,#1CC1=CC(C(C)(C)C)=C(O[Si](C)(C)C)C(C(C)(C)C)=C11751.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
2,6-Di-tert-butyl-4-methylphenol,1TBDMS,#1CC1=CC(C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C(C(C)(C)C)=C11989.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 2,6-Di-tert-butyl-4-methylphenol EI-B (Non-derivatized)splash10-0a4i-2190000000-9fbadde6214d718465402017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2,6-Di-tert-butyl-4-methylphenol EI-B (Non-derivatized)splash10-0a4i-7490000000-b8f13a22c093b18836672017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2,6-Di-tert-butyl-4-methylphenol EI-B (Non-derivatized)splash10-0a4i-8590000000-bb65eb9156b08a98eb132017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2,6-Di-tert-butyl-4-methylphenol EI-B (Non-derivatized)splash10-0a4i-4490000000-a19c5b42b06567024d6f2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2,6-Di-tert-butyl-4-methylphenol EI-B (Non-derivatized)splash10-0a4i-3490000000-ddeff8b438c2941c327e2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2,6-Di-tert-butyl-4-methylphenol EI-B (Non-derivatized)splash10-0a4i-2190000000-9fbadde6214d718465402018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2,6-Di-tert-butyl-4-methylphenol EI-B (Non-derivatized)splash10-0a4i-7490000000-b8f13a22c093b18836672018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2,6-Di-tert-butyl-4-methylphenol EI-B (Non-derivatized)splash10-0a4i-8590000000-bb65eb9156b08a98eb132018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2,6-Di-tert-butyl-4-methylphenol EI-B (Non-derivatized)splash10-0a4i-4490000000-a19c5b42b06567024d6f2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2,6-Di-tert-butyl-4-methylphenol EI-B (Non-derivatized)splash10-0a4i-3490000000-ddeff8b438c2941c327e2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2,6-Di-tert-butyl-4-methylphenol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-4890000000-937a0d7c9f6bc68849172016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2,6-Di-tert-butyl-4-methylphenol GC-MS (1 TMS) - 70eV, Positivesplash10-00fr-3190000000-b316f5f5da9b2ca1a8362017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2,6-Di-tert-butyl-4-methylphenol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a4i-7790000000-b645e922d4fa7b593cbc2014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 2,6-Di-tert-butyl-4-methylphenol DI-ESI-qTof , Negative-QTOFsplash10-0gb9-0090000000-beb559334e11b52a6a6b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2,6-Di-tert-butyl-4-methylphenol 10V, Negative-QTOFsplash10-014i-0090000000-32399a5e228ba02e4e322021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2,6-Di-tert-butyl-4-methylphenol 20V, Negative-QTOFsplash10-014i-0090000000-b36ce28bdef9bd2f364b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2,6-Di-tert-butyl-4-methylphenol 40V, Negative-QTOFsplash10-0fr6-5090000000-217bda984af47583c3112021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2,6-Di-tert-butyl-4-methylphenol 10V, Positive-QTOFsplash10-03di-0920000000-05e50a2a2ff3734570542021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2,6-Di-tert-butyl-4-methylphenol 20V, Positive-QTOFsplash10-03di-0900000000-2cc85cec8e88b993179f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2,6-Di-tert-butyl-4-methylphenol 40V, Positive-QTOFsplash10-001i-0900000000-3062a57022e6dc3200a32021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2,6-Di-tert-butyl-4-methylphenol 30V, Positive-QTOFsplash10-03di-0900000000-7cfc05798b5e4aee58742021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,6-Di-tert-butyl-4-methylphenol 10V, Positive-QTOFsplash10-00di-0090000000-f5adfac3bff91424bb5a2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,6-Di-tert-butyl-4-methylphenol 20V, Positive-QTOFsplash10-00di-1490000000-16fb4ab4552b3f6dc2d22016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,6-Di-tert-butyl-4-methylphenol 40V, Positive-QTOFsplash10-0ab9-3920000000-413f3c2e53c1dfbc97f22016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,6-Di-tert-butyl-4-methylphenol 10V, Negative-QTOFsplash10-014i-0090000000-361c47d317a34fbbf4032016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,6-Di-tert-butyl-4-methylphenol 20V, Negative-QTOFsplash10-014i-0090000000-27b24d01f4d65ae3d8ff2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,6-Di-tert-butyl-4-methylphenol 40V, Negative-QTOFsplash10-014i-0970000000-c5d8c2d3517a4486f6c22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,6-Di-tert-butyl-4-methylphenol 10V, Negative-QTOFsplash10-014i-0090000000-4af4c4ee1c4acef7e18b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,6-Di-tert-butyl-4-methylphenol 20V, Negative-QTOFsplash10-014i-0090000000-4af4c4ee1c4acef7e18b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,6-Di-tert-butyl-4-methylphenol 40V, Negative-QTOFsplash10-0f7a-0950000000-311825055cfa82a1e8702021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,6-Di-tert-butyl-4-methylphenol 10V, Positive-QTOFsplash10-0avi-0930000000-c53bfeff3f15a3ffd9312021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,6-Di-tert-butyl-4-methylphenol 20V, Positive-QTOFsplash10-0a4i-7910000000-9e7b8280fd5866b2aa5c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,6-Di-tert-butyl-4-methylphenol 40V, Positive-QTOFsplash10-0a4l-9100000000-430b6d18363b022950502021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
UrineDetected and Quantified0.000174 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB011992
KNApSAcK IDC00042069
Chemspider ID13835296
KEGG Compound IDC14693
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkButylated_hydroxytoluene
METLIN IDNot Available
PubChem Compound31404
PDB IDNot Available
ChEBI ID34247
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1029651
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Liu R, Mabury SA: Unexpectedly high concentrations of 2,4-di-tert-butylphenol in human urine. Environ Pollut. 2019 Sep;252(Pt B):1423-1428. doi: 10.1016/j.envpol.2019.06.077. Epub 2019 Jun 21. [PubMed:31265952 ]
  2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .