Butylated hydroxyanisole (CHEM003638)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2014-09-11 02:04:40 UTC
Update Date2026-05-20 18:29:23 UTC
Accession NumberCHEM003638
Identification
Common NameButylated hydroxyanisole
ClassSmall Molecule
DescriptionAntioxidant. Butylated hydroxyanisole is used in foods. 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 in certain amounts as a food additive with the E number E320. Butylated hydroxyanisole has been shown to exhibit anti-mutagen, anti-tumor and radical scavenger functions (1, 2, 3). Butylated hydroxyanisole belongs to the family of Methoxyphenols and Derivatives. These are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.
Contaminant Sources
  • EAFUS Chemicals
  • FooDB Chemicals
  • HPV EPA Chemicals
  • IARC Carcinogens Group 2B
  • My Exposome Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
Contaminant Type
  • Food Additive
  • Food Toxin
  • Household Toxin
  • Metabolite
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(1,1-Dimethylethyl)-4-methoxy-phenolHMDB
(1,1-Dimethylethyl)-4-methoxyphenol, 9ciHMDB
2(3)-Tert-butyl-4-hydroxyanisoleHMDB
2-(1,1-Dimethylethyl)-4-methoxy-phenolHMDB
2-Butyl-4-hydroxyanisoleHMDB
2-Tert-butyl-4-methoxy-phenolHMDB
2-Tert-butyl-4-methoxyphenolHMDB
3-BHAHMDB
3-t-Butyl-4-hydroxyanisoleHMDB
4-Methoxy-2-tert-butylphenolHMDB
Antioxyne bHMDB
BHAHMDB, MeSH
ButylhydroxyanisoleHMDB, MeSH
EmbanoxHMDB, MeSH
ProtexHMDB
Sustane 1FHMDB
Tenox bhaHMDB, MeSH
Tert-butyl-4-methoxyphenolHMDB
Tert-butylhydroxyanisoleHMDB
Butyl methoxyphenolMeSH
Butylated hydroxyanisoleMeSH
AMIF-72MeSH
Hydroxyanisole, butylatedMeSH
Nipantiox 1-FMeSH
Nipantiox 1FMeSH
AMIF 72MeSH
AMIF72MeSH
Nipantiox 1 FMeSH
(1,1-Dimethylethyl)-4-methoxyphenolMeSH
Methoxyphenol, butylMeSH
Chemical FormulaC22H32O4
Average Molecular Mass360.487 g/mol
Monoisotopic Mass360.230 g/mol
CAS Registry Number25013-16-5
IUPAC NameNot Available
Traditional Name3-tert-butyl-4-hydroxyanisole; 3-tert-butyl-4-methoxyphenol
SMILESCOC1=CC(=C(O)C=C1)C(C)(C)C.COC1=C(C=C(O)C=C1)C(C)(C)C
InChI IdentifierInChI=1S/2C11H16O2/c1-11(2,3)9-7-8(13-4)5-6-10(9)12;1-11(2,3)9-7-8(12)5-6-10(9)13-4/h2*5-7,12H,1-4H3
InChI KeyCZBZUDVBLSSABA-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 FrameworkNot Available
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point104 - 105 °C
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
logP3.06ChemAxon
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 Count4ChemAxon
Refractivity53.17 m³·mol⁻¹ChemAxon
Polarizability20.42 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0079-7980000000-87abe5aa52479d1bd461Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0009000000-1c029a60f5731df2a2c0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0009000000-1c029a60f5731df2a2c0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-0009000000-1c029a60f5731df2a2c0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0009000000-067a50384b6cf836b66fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0009000000-067a50384b6cf836b66fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-0009000000-067a50384b6cf836b66fSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)2B, possibly carcinogenic to humans. (4)
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0031848
FooDB IDFDB008532
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkButylated hydroxyanisole
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID24667
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available