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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2012-05-18 15:59:06 UTC
Update Date2019-07-23 05:59:23 UTC
HMDB IDHMDB0013825
Secondary Accession Numbers
  • HMDB0032528
  • HMDB13825
  • HMDB32528
Metabolite Identification
Common Name4-(1,1,3,3-Tetramethylbutyl)-phenol
Description4-(1,1,3,3-Tetramethylbutyl)-phenol is manufactured via a catalytic reaction of phenol with diisobutylene. It is a member of the class of compounds known as phenylpropanes. Phenylpropanes are organic compounds that contain a phenylpropane moiety. 4-(1,1,3,3-Tetramethylbutyl)-phenol can be found primarily in feces and urine. Within the cell, 4-(1,1,3,3-Tetramethylbutyl)-phenol is primarily located in the membrane (predicted from logP). It is a non-carcinogenic (not listed by IARC) potentially toxic compound. 4-(1,1,3,3-Tetramethylbutyl)-phenol is biodegradable, and in the surface layer of natural waters, 30% of OP can be degraded within one day. 4-(1,1,3,3-Tetramethylbutyl)-phenol is acutely very toxic to aquatic organisms and may cause long-term adverse effects in the aquatic environment. It is not acutely toxic to human health, but it is slightly irritating to the skin and highly irritating to the eyes. It is not genotoxic, but it may cause depigmentation of the skin. 4-(1,1,3,3-Tetramethylbutyl)-phenol is used as a food additive (EAFUS: Everything Added to Food in the United States).
Structure
Data?1563861563
Synonyms
ValueSource
4-t-OctylphenolKegg
4-(1,1,3,3-Tetramethylbutyl)phenolKegg
4-(1,1,3,3-Tetramethylbutyl)phenol (acd/name 4.0)HMDB
Octylphenol PTHMDB
p-(1',1',3', 3'-Tetramethylbutyl)phenolHMDB
p-(1',1',3',3'-Tetramethylbutyl)phenolHMDB
p-(1,1,3,3-Tetramethylbutyl)-phenolHMDB
p-(1,1,3,3-Tetramethylbutyl)phenolHMDB
p-(Tert-octyl)-phenolHMDB
p-OctylphenolHMDB
p-Terc.oktylfenolHMDB
p-Tert-octylphenolHMDB
Para-tert-octylphenolHMDB
Tert-octylphenol, flakedHMDB
alpha-(p-(1,1,3,3-Tetramethylbutyl)phenyl)-omega-hydroxypoly(oxyethylene)HMDB
4-Tertiary-octylphenolMeSH
a-(p-(1,1,3,3-Tetramethylbutyl)phenyl)-omega-hydroxypoly(oxyethylene)Generator
Α-(p-(1,1,3,3-tetramethylbutyl)phenyl)-omega-hydroxypoly(oxyethylene)Generator
Chemical FormulaC14H22O
Average Molecular Weight206.3239
Monoisotopic Molecular Weight206.167065326
IUPAC Name4-(2,4,4-trimethylpentan-2-yl)phenol
Traditional Name4-tert-octylphenol
CAS Registry Number140-66-9
SMILES
CC(C)(C)CC(C)(C)C1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C14H22O/c1-13(2,3)10-14(4,5)11-6-8-12(15)9-7-11/h6-9,15H,10H2,1-5H3
InChI KeyISAVYTVYFVQUDY-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
Disposition

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point84.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.026 g/LALOGPS
logP5.29ALOGPS
logP4.69ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)10.23ChemAxon
pKa (Strongest Basic)-5.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity64.93 m³·mol⁻¹ChemAxon
Polarizability24.96 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-2900000000-f92b122dd7da7c354da1JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0a4i-2190000000-c49bfd01ea946c72fc2eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0190000000-312caab5fa71d0dbc4acJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1590000000-554843e16a1b867f1463JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052s-5900000000-e546135869e4f5ba7231JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0090000000-b410576bf25ec1ab460fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0090000000-1705cc32a155c97241fbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0abi-4930000000-b11aff47964eb8485919JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-000i-3900000000-e0acd3551aaaeb8bc0a2JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Feces
  • Urine
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
UrineDetected but not Quantified Adult (>18 years old)BothNormal
    • Zhang, S., Liu, L...
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 IDFDB010381
KNApSAcK IDNot Available
Chemspider ID8483
KEGG Compound IDC14205
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound8814
PDB ID27L
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). EAFUS: Everything Added to Food in the United States.. .