4-tert-Butylphenol (CHEM003837)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (3)XML
Record Information
Version1.0
Creation Date2014-09-11 05:20:39 UTC
Update Date2026-03-31 18:55:14 UTC
Accession NumberCHEM003837
Identification
Common Name4-tert-Butylphenol
ClassSmall Molecule
Description4-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
Thumb
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-8900000000-fcc9d5515e40bf2ce9bfSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-2900000000-4db3c9778d301443456dSpectrum
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-0002-0910000000-5f1bfd35cf8deb78b98cSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-8900000000-fcc9d5515e40bf2ce9bfSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-2900000000-4db3c9778d301443456dSpectrum
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-0002-0910000000-5f1bfd35cf8deb78b98cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f7c-6900000000-e6bc03dc9e08a393382aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0ab9-7950000000-9a3eb623432cc113e7c1Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 5V, negativesplash10-0002-0900000000-1b438e2954f692bde21cSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 6V, negativesplash10-0002-0900000000-4869d097cbf53b54eac7Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 7V, negativesplash10-0002-0900000000-eb91984e2eee362605eaSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 8V, negativesplash10-001j-0900000000-6f41817f2d53326891f5Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 9V, negativesplash10-001i-0900000000-743d3c04ea258d8d65f4Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 11V, negativesplash10-001i-0900000000-5b6aa25385985d180564Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 12V, negativesplash10-001i-1900000000-fd9628d81ef8f4e18133Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 14V, negativesplash10-001i-2900000000-ccd8003868f8bdeccc5cSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 10V, negativesplash10-001i-0900000000-d8230f5f259df6fea000Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 7V, negativesplash10-001i-1900000000-cfab9ce208c524adf321Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 8V, negativesplash10-00lu-2900000000-b607a227fde521d76913Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 9V, negativesplash10-014i-3900000000-81462e4176534374f843Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 11V, negativesplash10-014i-2900000000-13838214504729aab127Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 12V, negativesplash10-014i-2900000000-c76ede2275038ed75b6dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-e180d190b00910efa382Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-1900000000-57816f46479a4b16509fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kmi-4900000000-4d051f92232b77a4f222Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-22731f94c93a65d86fa7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-af037d6638ec1135f64aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-3900000000-c10592e6ba17dd98b6baSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-3900000000-fceeeeb8e46c4e45273bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9100000000-a55d19411e2dc8e43a3dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9100000000-b8f56188be6daa978d82Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-22917433edc8ad9dbc2eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-22917433edc8ad9dbc2eSpectrum
MSMass Spectrum (Electron Ionization)splash10-000i-5900000000-d83739407ea92534ecafSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
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
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.