4-HYDROXYMETHYL-2,6-DI-TERTBUTYLPHENOL (CHEM006073)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-19 02:09:42 UTC
Update Date2016-11-09 01:09:40 UTC
Accession NumberCHEM006073
Identification
Common Name4-HYDROXYMETHYL-2,6-DI-TERTBUTYLPHENOL
ClassSmall Molecule
Description2,6-Di-tert-butyl-4-hydroxymethylphenol, also known as BHT-OH, 3,5-di-tert-butyl-4-hydroxy-benzyl alcohol, or 4-hydroxymethyl-2,6-di-tert-butylphenol, belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety. BHT-OH is an extremely weak basic (essentially neutral) compound (based on its pKa). BHT-OH is a metabolite of 2,6-di-tert-butyl-4-methylphenol (BHA), 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-OH was detected in human urine (PMID: 31265952).
Contaminant Sources
  • EAFUS Chemicals
  • FooDB Chemicals
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2, 6-Di-tert-butyl-4-(hydroxymethyl)phenolHMDB
2, 6-Di-tert-butyl-4-hydroxymethylphenolHMDB
2,6-Bis(1,1-dimethylethyl)-4-(hydroxymethyl)phenolHMDB
2,6-Di-t-butyl-4-hydroxymethylphenolHMDB
2,6-Di-tert-butyl-4-(hydroxymethyl)phenolHMDB
2,6-Di-tert-butyl-4-hydroxymethyl phenolHMDB
3,5-Bis(1,1-dimethylethyl)-4-hydroxy-benzenemethanolHMDB
3,5-Bis(1,1-dimethylethyl)-4-hydroxybenzenemethanolHMDB
3,5-Bis(1,1-dimethylethyl)-4-hydroxybenzenemethanol, 9ciHMDB
3,5-Di-t-butyl-4-hydroxybenzyl alcoholHMDB
3,5-Di-tert-butyl-4-hydroxy-benzyl alcoholHMDB
3,5-Di-tert-butyl-4-hydroxybenzyl alcoholHMDB
3,5-Di-tert-butyl-4-hydroxybenzyl alcohol, 8ciHMDB
4-Hydroxymethyl-2,6-di-tert-butylphenolHMDB, MeSH
4-Hydroxymethyl-2,6-di-tertbutylphenolHMDB
alpha-Hydroxy-2,6-di-tert-butyl-P-cresolHMDB
Antioxidant 754HMDB
Benzenemethanol, 4-hydroxy-3,5-di-tert.-butylHMDB
BHT AlcoholHMDB
Butylated hydroxymethylphenolHMDB
Di-tert-butyl-4-hydroxymethyl phenolHMDB
Ionox 100HMDB
Ionox 100 antioxidantHMDB
4-HMDBPMeSH, HMDB
BHTBzOHMeSH, HMDB
2,6-Di-tert-butyl-4-hydroxymethylphenolMeSH
3,5-Di-t-butyl-4-hidroxy-benzyl alcoholHMDB
3,5-Di-tert-butyl-4-hydroxyphenylmethanolHMDB
4-Hydroxy-3,5-di-tert-butylbenzyl alcoholHMDB
BHT-OHHMDB
Chemical FormulaC15H24O2
Average Molecular Mass236.350 g/mol
Monoisotopic Mass236.178 g/mol
CAS Registry Number88-26-6
IUPAC Name2,6-di-tert-butyl-4-(hydroxymethyl)phenol
Traditional Name2,6-di-tert-butyl-4-(hydroxymethyl)phenol
SMILESCC(C)(C)C1=CC(CO)=CC(=C1O)C(C)(C)C
InChI IdentifierInChI=1S/C15H24O2/c1-14(2,3)11-7-10(9-16)8-12(13(11)17)15(4,5)6/h7-8,16-17H,9H2,1-6H3
InChI KeyHNURKXXMYARGAY-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
  • Benzyl alcohol
  • Phenol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.15 g/LALOGPS
logP4ALOGPS
logP3.99ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)10.73ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity72.19 m³·mol⁻¹ChemAxon
Polarizability28.31 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-5980000000-c4903b8c014660089b1fSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-5980000000-c4903b8c014660089b1fSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-1590000000-c105d4c8edcd01f667b2Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0avi-8049000000-0266b8a9fd3717df38faSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-0090000000-c6e1869c905799e56672Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0290000000-7738b3dee209e378e21dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014r-1590000000-d4b4f40a51824b17d1daSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-215a903d9c5e8b2bf4f8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052r-0090000000-9fb4b7f36c9ac96700c3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4r-0590000000-d4aefa264a3d261899e9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-c0031dc201eac6b6350aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-3387d858c61f65b3f554Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-0690000000-a17a93b7b3d961cbe117Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1590000000-c33d33740f4d9b567ca9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-08fr-4940000000-1dea2fb5642c1a3c1f6cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9600000000-bf881e2fdcee13275509Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0032048
FooDB IDFDB008752
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID6663
ChEBI IDNot Available
PubChem Compound ID6929
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot 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.
2. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.