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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2012-05-18 15:59:04 UTC
Update Date2023-02-21 17:18:04 UTC
HMDB IDHMDB0013816
Secondary Accession Numbers
  • HMDB13816
Metabolite Identification
Common Name2,4-Di-tert-butylphenol
Description2,4-Di-tert-butylphenol, also known as 2,4-DTBP, belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety. 2,4-Di-tert-butylphenol is an extremely weak basic (essentially neutral) compound (based on its pKa). 2,4-Di-tert-butylphenol is 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. 2,4-Di-tert-butylphenol was detected at extremely high concentrations in human urine (PMID: 31265952 ).
Structure
Data?1676999884
Synonyms
ValueSource
1-Hydroxy-2,4-di-tert-butylbenzeneChEBI
2,4-Bis(1,1'-dimethylethyl)phenolChEBI
2,4-Bis(1,1-dimethylethyl)-phenolChEBI
2,4-Bis(1,1-dimethylethyl)phenolChEBI
2,4-Bis(tert-butyl)phenolChEBI
2,4-Di-t-butylphenolChEBI
2,4-Tert-butylphenolChEBI
2,4-DTBPHMDB
2,4-Di-tert-butyl-phenolHMDB
2,4-Di-tert-butylhydroxybenzeneHMDB
DBPHMDB
2,4-Di-tert-butylphenolMeSH
Chemical FormulaC14H22O
Average Molecular Weight206.329
Monoisotopic Molecular Weight206.167065328
IUPAC Name2,4-di-tert-butylphenol
Traditional Name2,4-di-T-butylphenol
CAS Registry Number96-76-4
SMILES
CC(C)(C)C1=CC=C(O)C(=C1)C(C)(C)C
InChI Identifier
InChI=1S/C14H22O/c1-13(2,3)10-7-8-12(15)11(9-10)14(4,5)6/h7-9,15H,1-6H3
InChI KeyICKWICRCANNIBI-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylpropanes
Direct ParentPhenylpropanes
Alternative Parents
Substituents
  • Phenylpropane
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point56.5 °CNot Available
Boiling Point263.00 to 264.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility0.035 mg/mL at 25 °CNot Available
LogP5.19Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal
    • Zhang, S., Liu, L...
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.0608 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)
details
Associated Disorders and Diseases
Disease References
Nonalcoholic fatty liver disease
  1. Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDC00052597
Chemspider ID7037
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound7311
PDB IDNot Available
ChEBI ID89188
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1163331
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 ]