2-tert-Butyl-4-methoxyphenol (CHEM017617)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 04:29:54 UTC
Update Date2016-11-09 01:15:38 UTC
Accession NumberCHEM017617
Identification
Common Name2-tert-Butyl-4-methoxyphenol
ClassSmall Molecule
DescriptionAn aromatic ether that is 4-methoxyphenol in which one of the hydrogens ortho- to the phenolic hydroxy group is replaced by a tert-butyl group.
Contaminant Sources
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
2-(1,1-Dimethylethyl)-4-methoxyphenolChEBI
3-(1,1-Dimethylethyl)-4-hydroxyanisoleChEBI
3-BHAChEBI
3-Tert-butyl-p-hydroxyanisoleChEBI
4-Hydroxy-3-tert-butylanisoleChEBI
4-Methoxy-2-tert-butylphenolChEBI
4-Methoxy-6-tert-butylphenolChEBI
O-Tert-butyl-p-methoxyphenolChEBI
p-Methoxy-O-tert-butylphenolChEBI
(1,1-Dimethylethyl)-4-methoxyphenolHMDB
Methoxyphenol, butylHMDB
AMIF72HMDB
BHAHMDB
ButylhydroxyanisoleHMDB
Nipantiox 1 FHMDB
AMIF-72HMDB
Hydroxyanisole, butylatedHMDB
Nipantiox 1-FHMDB
Nipantiox 1FHMDB
Tenox bhaHMDB
AMIF 72HMDB
Butyl methoxyphenolHMDB
Butylated hydroxyanisoleHMDB
EmbanoxHMDB
2-Tert-butyl-4-methoxyphenolHMDB
2-Tert-butyl-p-methoxyphenolHMDB
Tert-butyl-2-methoxy-4-phenolHMDB
3-tert-Butyl-4-hydroxyanisoleHMDB
Chemical FormulaC11H16O2
Average Molecular Mass180.244 g/mol
Monoisotopic Mass180.115 g/mol
CAS Registry Number121-00-6
IUPAC Name2-tert-butyl-4-methoxyphenol
Traditional Name3-tert-butyl-4-hydroxyanisole
SMILESCOC1=CC(=C(O)C=C1)C(C)(C)C
InChI IdentifierInChI=1S/C11H16O2/c1-11(2,3)9-7-8(13-4)5-6-10(9)12/h5-7,12H,1-4H3
InChI KeyMRBKEAMVRSLQPH-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassMethoxyphenols
Direct ParentMethoxyphenols
Alternative Parents
Substituents
  • Methoxyphenol
  • 4-alkoxyphenol
  • Phenylpropane
  • Phenoxy compound
  • Methoxybenzene
  • Phenol ether
  • Anisole
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
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 Solubility0.97 g/LALOGPS
logP3.25ALOGPS
logP3.06ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)10.57ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.46 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity53.17 m³·mol⁻¹ChemAxon
Polarizability20.42 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-4900000000-3f285fdccb9fbe4de2d2Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-4900000000-3f285fdccb9fbe4de2d2Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-014r-2900000000-6e34e81692e6395c1afeSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ( TMS) - 70eV, Positivesplash10-0079-7980000000-87abe5aa52479d1bd461Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Negativesplash10-004i-0900000000-58f82fc5543c0d66c899Spectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Negativesplash10-004i-0900000000-6de1ada6e165cb9fddbeSpectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Negativesplash10-004i-0900000000-3f65bbae1c7c5e9e8a29Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-004i-0900000000-9f05f550021e6570b637Spectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Negativesplash10-004i-0900000000-0fdac0b3ba8a4734505aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-63e540598f2fa990edf3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-1900000000-8066217d99f73fa2ec65Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0l7r-4900000000-65da2551598499ee4dacSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-114f004bbcdf6d4522fdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0900000000-6c34280448208d6da7b3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-08gj-4900000000-78c4ba94b80f66329158Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-d1acfc4fe8cc20fdb3bfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000t-2900000000-4a41c9b45ff018073785Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-7900000000-8a4f1f09112bf7710dfdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-ed614b6bd089f6f9641aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-1900000000-a34b44e76c734ea442eaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0bta-4900000000-08b175b62b67340b812aSpectrum
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 IDHMDB0059925
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkButylated_hydroxyanisole
Chemspider ID8145
ChEBI ID76358
PubChem Compound ID8456
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=3201475
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=4053035
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=6542057
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=7388831
5. Cummings SW, Ansari GA, Guengerich FP, Crouch LS, Prough RA: Metabolism of 3-tert-butyl-4-hydroxyanisole by microsomal fractions and isolated rat hepatocytes. Cancer Res. 1985 Nov;45(11 Pt 2):5617-24.
6. Castelli MG, Benfenati E, Pastorelli R, Salmona M, Fanelli R: Kinetics of 3-tert-butyl-4-hydroxyanisole (BHA) in man. Food Chem Toxicol. 1984 Nov;22(11):901-4.
7. Wattenberg LW, Coccia JB, Lam LK: Inhibitory effects of phenolic compounds on benzo(a)pyrene-induced neoplasia. Cancer Res. 1980 Aug;40(8 Pt 1):2820-3.
8. 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.