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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2012-09-11 18:36:03 UTC
Update Date2020-04-28 16:21:50 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 an extremely weak basic (essentially neutral) compound (based on its pKa). 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-Bis(1,1-dimethylethyl)-4-methylphenol, 9ciHMDB
2,6-Di-tert-butyl-p-cresol, 8ciHMDB
Butyl hydroxy tolueneHMDB
e321HMDB
FEMA 2184HMDB
IonolHMDB
PopolHMDB
2,6 Di t butyl 4 methylphenolHMDB
4-Methyl-2,6-ditertbutylphenolHMDB
Hydroxytoluene, butylatedHMDB
Ionol (BHT)HMDB
2,6 Di tert butyl p cresolHMDB
4 Methyl 2,6 ditertbutylphenolHMDB
DibunolHMDB
Di-tert-butyl-methylphenolMeSH
2,6 Di tert butyl 4 methylphenolMeSH
Di tert butyl methylphenolMeSH
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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point71 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0006 mg/mL at 25 °CNot Available
LogP5.10Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.015 g/LALOGPS
logP5.25ALOGPS
logP5.27ChemAxon
logS-4.2ALOGPS
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
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-2190000000-9fbadde6214d71846540Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-7490000000-b8f13a22c093b1883667Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-8590000000-bb65eb9156b08a98eb13Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-4490000000-a19c5b42b06567024d6fSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-3490000000-ddeff8b438c2941c327eSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-2190000000-9fbadde6214d71846540Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-7490000000-b8f13a22c093b1883667Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-8590000000-bb65eb9156b08a98eb13Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-4490000000-a19c5b42b06567024d6fSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-3490000000-ddeff8b438c2941c327eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-4890000000-937a0d7c9f6bc6884917Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00fr-3190000000-b316f5f5da9b2ca1a836Spectrum
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Negativesplash10-0gb9-0090000000-beb559334e11b52a6a6bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0090000000-f5adfac3bff91424bb5aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-1490000000-16fb4ab4552b3f6dc2d2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ab9-3920000000-413f3c2e53c1dfbc97f2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-361c47d317a34fbbf403Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0090000000-27b24d01f4d65ae3d8ffSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-0970000000-c5d8c2d3517a4486f6c2Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a4i-7790000000-b645e922d4fa7b593cbcSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not Quantified Adult (>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
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.. .