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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:47:32 UTC
Update Date2019-07-23 06:10:13 UTC
HMDB IDHMDB0032063
Secondary Accession Numbers
  • HMDB32063
Metabolite Identification
Common Name4-tert-Butylphenol
Description4-tert-Butylphenol, also known as butylphen or PTBP, belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety. 4-tert-Butylphenol is an extremely weak basic (essentially neutral) compound (based on its pKa). 4-tert-Butylphenol is a leather and oakmoss tasting compound. Outside of the human body, 4-tert-Butylphenol has been detected, but not quantified in, herbs and spices. This could make 4-tert-butylphenol a potential biomarker for the consumption of these foods. 4-Tert-butylphenol is structurally similar to the melanin precursor tyrosine, and acts as a substrate for tyrosinase. 4-tert-Butylphenol is a potentially toxic compound. 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. 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).
Structure
Data?1563862213
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 Weight150.2176
Monoisotopic Molecular Weight150.10446507
IUPAC Name4-tert-butylphenol
Traditional Name4-tert-butylphenol
CAS Registry Number98-54-4
SMILES
CC(C)(C)C1=CC=C(O)C=C1
InChI Identifier
InChI=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
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point99 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.58 mg/mL at 25 °CNot Available
LogP3.31Not Available
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
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 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
MSMass Spectrum (Electron Ionization)splash10-000i-5900000000-d83739407ea92534ecafSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)BothNormal details
FecesDetected but not Quantified Children (1-13 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)BothImmunoglobulin A nephropathy (IgAN) non progressor details
FecesDetected but not Quantified Adult (>18 years old)BothImmunoglobulin A nephropathy (IgAN) progressor details
FecesDetected but not Quantified Children (1-13 years old)Bothautism details
FecesDetected but not Quantified Children (1-13 years old)BothPervasive Developmental Disorder Not Otherwise Specified details
Associated Disorders and Diseases
Disease References
Autism
  1. De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]
Pervasive developmental disorder not otherwise specified
  1. De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB008772
KNApSAcK IDNot Available
Chemspider ID13846663
KEGG Compound IDC14200
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound7393
PDB IDNot Available
ChEBI ID34444
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .