Benzoic acid, 3,5-bis(1,1-dimethylethyl)-4-hydroxy- (CHEM010189)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-19 03:18:14 UTC
Update Date2016-11-09 01:14:09 UTC
Accession NumberCHEM010189
Identification
Common NameBenzoic acid, 3,5-bis(1,1-dimethylethyl)-4-hydroxy-
ClassSmall Molecule
Description3,5-Di-tert-butyl-4-hydroxybenzoic acid, also known as BHT-COOH or 4-carboxy-2,6-di-tert-butylphenol, belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups. BHT-COOH 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
  • HPV EPA Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3,5-Di-tert-butyl-4-hydroxybenzoateGenerator
BHT-COOHHMDB
2,6-Di-tert-butyl-4-carboxyphenolHMDB
3,5-Bis(1,1-dimethylethyl)-4-hydroxybenzoic acidHMDB
4-Carboxy-2,6-di-tert-butylphenolHMDB
4-Hydroxy-3,5-di-tert-butylbenzoic acidHMDB
3,5-Di-tert-butyl-4-hydroxybenzoic acidMeSH
Chemical FormulaC15H22O3
Average Molecular Mass250.338 g/mol
Monoisotopic Mass250.157 g/mol
CAS Registry Number1421-49-4
IUPAC Name3,5-di-tert-butyl-4-hydroxybenzoic acid
Traditional Name3,5-di-tert-butyl-4-hydroxybenzoic acid
SMILESCC(C)(C)C1=CC(=CC(=C1O)C(C)(C)C)C(O)=O
InChI IdentifierInChI=1S/C15H22O3/c1-14(2,3)10-7-9(13(17)18)8-11(12(10)16)15(4,5)6/h7-8,16H,1-6H3,(H,17,18)
InChI KeyYEXOWHQZWLCHHD-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentHydroxybenzoic acid derivatives
Alternative Parents
Substituents
  • Hydroxybenzoic acid
  • Phenylpropane
  • Benzoic acid
  • Benzoyl
  • Phenol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • 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 Solubility0.11 g/LALOGPS
logP4.5ALOGPS
logP4.42ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)4.36ChemAxon
pKa (Strongest Basic)-5.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity72.63 m³·mol⁻¹ChemAxon
Polarizability28.44 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0090000000-7467e42064ee08ac42cbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f89-0390000000-974088ad571180615e1fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a7i-3690000000-682e13e87cc4e4ec8606Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-77e0271550d3898a3fe4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4j-0190000000-34a21f0d7a041ace1a6dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4j-1890000000-2dce0525ad25dd5303a7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0090000000-6a76724ca68c443d673eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4j-0090000000-250bf2625d573b97ae7aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-0960000000-02b30cc39bf8c672b6a0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0290000000-114a124b6a8e49fc6628Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udj-0590000000-35eb44b51adc0107f920Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a59-8900000000-1ef30a3afc57be07b7dfSpectrum
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 IDHMDB0240642
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID14285
ChEBI IDNot Available
PubChem Compound ID15007
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.