4-tert-Butylphenol (CHEM003837)

Record Information
Version1.0
Creation Date2014-09-11 05:20:39 UTC
Update Date2026-08-18 01:04:55 UTC
Accession NumberCHEM003837
Identification
Common Name4-tert-Butylphenol
ClassSmall Molecule
Description
4-tert-Butylphenol is found in herbs and spices. 4-tert-Butylphenol is found in oregano. 4-tert-Butylphenol is a flavour ingredient. 4-tert-Butylphenol belongs to the family of Cumenes. These are aromatic compounds containing a prop-2-ylbenzene moiety.
Contaminant Sources
  • EAFUS Chemicals
  • FooDB Chemicals
  • HPV EPA Chemicals
  • OECD HPV Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Food Toxin
  • Household Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
  • Plant Toxin
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
4-(1,1-Dimethylethyl)phenolChEBI
4-Tert-butyl-phenolChEBI
ButylphenChEBI
p-t-Butyl phenolChEBI
p-Tert-butylphenolChEBI
Para-tertiary-butylphenolChEBI
PTBPChEBI
1-Hydroxy-4-tert-butylbenzeneHMDB
2-(4-Hydroxyphenyl)-2-methylpropaneHMDB
4-(1, 1-Dimethylethyl)phenolHMDB
4-(1,1-Dimethylethyl)-phenolHMDB
4-(1,1-Dimethylethyl)phenol, 9ciHMDB
4-t-ButylphenolHMDB
4-Tertiary-butylphenolHMDB
FEMA 3918HMDB
Lowinox 070HMDB
Lowinox PTBTHMDB
Lowinox TBMXHMDB
p-(Tert-butyl)-phenolHMDB
p-Sec-butylphenolHMDB
p-t-ButylphenolHMDB
p-Terc.butylfenolHMDB
p-Tert-butyl-phenolHMDB
T-ButylphenolHMDB
Ucar butylphenol 4-THMDB
Ucar butylphenol 4-T flakeHMDB
4-(t-Butyl)phenolHMDB
Chemical FormulaC10H14O
Average Molecular Mass150.218 g/mol
Monoisotopic Mass150.104 g/mol
CAS Registry Number98-54-4
IUPAC Name4-tert-butylphenol
Traditional Name4-tert-butylphenol
SMILESCC(C)(C)C1=CC=C(O)C=C1
InChI IdentifierInChI=1S/C10H14O/c1-10(2,3)8-4-6-9(11)7-5-8/h4-7,11H,1-3H3
InChI KeyQHPQWRBYOIRBIT-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 Descriptors
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 Point99 °C
Boiling PointNot Available
Solubility0.58 mg/mL at 25 °C
Predicted Properties
PropertyValueSource
Water Solubility0.65 g/LALOGPS
logP3.47ALOGPS
logP3.21ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)10.24ChemAxon
pKa (Strongest Basic)-5.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity46.7 m³·mol⁻¹ChemAxon
Polarizability17.64 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureDermal
Mechanism of Toxicity4-Tert-butylphenol is structurally similar to the melanin precursor tyrosine, and acts as a substrate for tyrosinase. Tyrosinase oxidizes 4-tert-butylphenol to a quinone (4-tert-butylcyclohexa-3,5-diene-1,2-dione) which in turn rapidly reacts with glutathione (GSH). A depletion of the GSH defence system may allow the quinone to generate reactive oxygen species that damage melanocytes and induce apoptosis, leading to leukoderma/vitiligo. (1, 2)
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/Sources4-Tert-butylphenol is also found in herbs and spices and in oregano. 4-tert-Butylphenol is a flavour ingredient.
Minimum Risk LevelNot Available
Health EffectsLeukoderma, vitiligo.
SymptomsLoss of skin pigmentation.
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0032063
FooDB IDFDB008772
Phenol Explorer IDNot Available
KNApSAcK IDC00045799
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID13846663
ChEBI ID34444
PubChem Compound ID7393
Kegg Compound IDC14200
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=24801287
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=26302341
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=26819047
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=8462290
5. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.