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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-03-20 21:10:35 UTC
Update Date2023-02-21 17:29:37 UTC
HMDB IDHMDB0059926
Secondary Accession Numbers
  • HMDB59926
Metabolite Identification
Common Name2-tert-Butyl-4-hydroxyanisole
Description2-tert-Butyl-4-hydroxyanisole is an ingredient in butylated hydroxyanisole. Butylated hydroxyanisole (BHA) is an antioxidant consisting of a mixture of two isomeric organic compounds, 2-tert-butyl-4-hydroxyanisole and 3-tert-butyl-4-hydroxyanisole. It is prepared from 4-methoxyphenol and isobutylene. It is a waxy solid used as a food additive with the E number E320. The primary use for BHA is as an antioxidant and preservative in food, food packaging, animal feed, cosmetics, rubber, and petroleum products. BHA also is commonly used in medicines, such as isotretinoin, lovastatin, and simvastatin, among others. (Wikipedia)
Structure
Data?1677000577
Synonyms
ValueSource
2-(1,1-Dimethylethyl)-4-hydroxyanisoleChEBI
2-BHAChEBI
2-Tert-butyl-p-hydroxyanisoleChEBI
3-(1,1-Dimethylethyl)-4-methoxyphenolChEBI
4-Hydroxy-2-tert-butylanisoleChEBI
4-Methoxy-3-tert-butylphenolChEBI
4-Methoxy-5-tert-butylphenolChEBI
m-Tert-butyl-p-methoxyphenolChEBI
p-Methoxy-m-tert-butylphenolChEBI
Chemical FormulaC11H16O2
Average Molecular Weight180.2435
Monoisotopic Molecular Weight180.115029756
IUPAC Name3-tert-butyl-4-methoxyphenol
Traditional Name3-tert-butyl-4-methoxyphenol
CAS Registry NumberNot Available
SMILES
COC1=C(C=C(O)C=C1)C(C)(C)C
InChI Identifier
InChI=1S/C11H16O2/c1-11(2,3)9-7-8(12)5-6-10(9)13-4/h5-7,12H,1-4H3
InChI KeyIMOYOUMVYICGCA-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
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.9 g/LALOGPS
logP3.29ALOGPS
logP3.06ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)10.01ChemAxon
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
Polarizability20.34 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+141.60531661259
DarkChem[M-H]-140.83931661259
DeepCCS[M+H]+148.37830932474
DeepCCS[M-H]-145.98230932474
DeepCCS[M-2H]-179.99330932474
DeepCCS[M+Na]+154.71930932474
AllCCS[M+H]+136.532859911
AllCCS[M+H-H2O]+132.332859911
AllCCS[M+NH4]+140.432859911
AllCCS[M+Na]+141.632859911
AllCCS[M-H]-139.932859911
AllCCS[M+Na-2H]-140.932859911
AllCCS[M+HCOO]-141.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-tert-Butyl-4-hydroxyanisoleCOC1=C(C=C(O)C=C1)C(C)(C)C2296.6Standard polar33892256
2-tert-Butyl-4-hydroxyanisoleCOC1=C(C=C(O)C=C1)C(C)(C)C1437.2Standard non polar33892256
2-tert-Butyl-4-hydroxyanisoleCOC1=C(C=C(O)C=C1)C(C)(C)C1507.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2-tert-Butyl-4-hydroxyanisole,1TMS,isomer #1COC1=CC=C(O[Si](C)(C)C)C=C1C(C)(C)C1541.3Semi standard non polar33892256
2-tert-Butyl-4-hydroxyanisole,1TBDMS,isomer #1COC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1C(C)(C)C1779.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2-tert-Butyl-4-hydroxyanisole GC-MS (Non-derivatized) - 70eV, Positivesplash10-014r-2900000000-80d60a326c7d3c117cf12017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-tert-Butyl-4-hydroxyanisole GC-MS (1 TMS) - 70eV, Positivesplash10-0079-7690000000-f9638c1cfffbb9419c7c2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-tert-Butyl-4-hydroxyanisole GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-tert-Butyl-4-hydroxyanisole 10V, Positive-QTOFsplash10-001i-0900000000-952f1abed5b90b5cb1c32017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-tert-Butyl-4-hydroxyanisole 20V, Positive-QTOFsplash10-001i-1900000000-c83820c0996f70b008252017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-tert-Butyl-4-hydroxyanisole 40V, Positive-QTOFsplash10-05ai-9700000000-cb2dd58cb0e50b44eee22017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-tert-Butyl-4-hydroxyanisole 10V, Negative-QTOFsplash10-004i-0900000000-7f2bb0dd12c0910a46702017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-tert-Butyl-4-hydroxyanisole 20V, Negative-QTOFsplash10-004i-0900000000-dcb6d6a4469d8809ac372017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-tert-Butyl-4-hydroxyanisole 40V, Negative-QTOFsplash10-06sr-3900000000-302820a046bd060f297e2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-tert-Butyl-4-hydroxyanisole 10V, Positive-QTOFsplash10-001i-0900000000-984d8c1e6b0e9783722e2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-tert-Butyl-4-hydroxyanisole 20V, Positive-QTOFsplash10-001i-3900000000-ceadd10ae33770d9182f2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-tert-Butyl-4-hydroxyanisole 40V, Positive-QTOFsplash10-0a4i-9800000000-59f3d48b777a1a96be402021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-tert-Butyl-4-hydroxyanisole 10V, Negative-QTOFsplash10-004i-0900000000-ed614b6bd089f6f9641a2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-tert-Butyl-4-hydroxyanisole 20V, Negative-QTOFsplash10-004i-0900000000-be91789dbe6c0517d4a02021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-tert-Butyl-4-hydroxyanisole 40V, Negative-QTOFsplash10-08fr-2900000000-756ff75497d1827d05392021-10-12Wishart 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 (predicted from logP)
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 IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6932
PDB IDNot Available
ChEBI ID76357
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [PubMed:7388831 ]