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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2020-04-28 16:47:45 UTC
Update Date2020-06-03 15:12:17 UTC
HMDB IDHMDB0240642
Secondary Accession NumbersNone
Metabolite Identification
Common Name3,5-Di-tert-butyl-4-hydroxybenzoic acid
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 ).
Structure
Data?1588093388
Synonyms
ValueSource
3,5-Di-tert-butyl-4-hydroxybenzoateGenerator
3,5-Di-tert-butyl-4-hydroxybenzoic acidMeSH
BHT-COOHMeSH
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
Chemical FormulaC15H22O3
Average Molecular Weight250.338
Monoisotopic Molecular Weight250.156894568
IUPAC Name3,5-di-tert-butyl-4-hydroxybenzoic acid
Traditional Name3,5-di-tert-butyl-4-hydroxybenzoic acid
CAS Registry Number1421-49-4
SMILES
CC(C)(C)C1=CC(=CC(=C1O)C(C)(C)C)C(O)=O
InChI Identifier
InChI=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
Ontology
Not Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
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
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified0.00187 umol/mmol creatinineAdult (>18 years old)BothNormal details
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 ID14285
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound15007
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not 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. [PubMed:31265952 ]