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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-05-18 15:59:06 UTC
Update Date2023-02-21 17:18:05 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?1676999885
Synonyms
ValueSource
4-t-OctylphenolKegg
4-(1,1,3,3-Tetramethylbutyl)phenolKegg
p-(1,1,3,3-Tetramethylbutyl)-phenolMeSH
p-Tert-octylphenolMeSH
4-Tertiary-octylphenolMeSH
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-(Tert-octyl)-phenolHMDB
P-OctylphenolHMDB
P-Terc.oktylfenolHMDB
Para-tert-octylphenolHMDB
Tert-octylphenol, flakedHMDB
alpha-(p-(1,1,3,3-Tetramethylbutyl)phenyl)-omega-hydroxypoly(oxyethylene)HMDB
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
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point84.5 °CNot Available
Boiling Point282.30 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility4.82 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP5.180 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+148.61131661259
DarkChem[M-H]-146.54331661259
DeepCCS[M+H]+155.85630932474
DeepCCS[M-H]-153.49830932474
DeepCCS[M-2H]-186.56630932474
DeepCCS[M+Na]+161.9530932474
AllCCS[M+H]+144.732859911
AllCCS[M+H-H2O]+140.732859911
AllCCS[M+NH4]+148.332859911
AllCCS[M+Na]+149.332859911
AllCCS[M-H]-152.232859911
AllCCS[M+Na-2H]-152.732859911
AllCCS[M+HCOO]-153.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-(1,1,3,3-Tetramethylbutyl)-phenolCC(C)(C)CC(C)(C)C1=CC=C(O)C=C12475.6Standard polar33892256
4-(1,1,3,3-Tetramethylbutyl)-phenolCC(C)(C)CC(C)(C)C1=CC=C(O)C=C11584.1Standard non polar33892256
4-(1,1,3,3-Tetramethylbutyl)-phenolCC(C)(C)CC(C)(C)C1=CC=C(O)C=C11638.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-(1,1,3,3-Tetramethylbutyl)-phenol,1TMS,isomer #1CC(C)(C)CC(C)(C)C1=CC=C(O[Si](C)(C)C)C=C11618.0Semi standard non polar33892256
4-(1,1,3,3-Tetramethylbutyl)-phenol,1TBDMS,isomer #1CC(C)(C)CC(C)(C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C11866.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4-(1,1,3,3-Tetramethylbutyl)-phenol GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-2900000000-f92b122dd7da7c354da12017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-(1,1,3,3-Tetramethylbutyl)-phenol GC-MS (1 TMS) - 70eV, Positivesplash10-0a4i-2190000000-c49bfd01ea946c72fc2e2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-(1,1,3,3-Tetramethylbutyl)-phenol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-000i-3900000000-e0acd3551aaaeb8bc0a22014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-(1,1,3,3-Tetramethylbutyl)-phenol 15V, Negative-QTOFsplash10-0a4i-0090000000-587e608db055a05c750e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-(1,1,3,3-Tetramethylbutyl)-phenol 90V, Negative-QTOFsplash10-000i-0920000000-1f2e6c1d05a0843dc24b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-(1,1,3,3-Tetramethylbutyl)-phenol 60V, Positive-QTOFsplash10-0a4i-0190000000-fbc10fa8cd95636b25312021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-(1,1,3,3-Tetramethylbutyl)-phenol 60V, Negative-QTOFsplash10-0a4i-0190000000-74392b748884c07a591e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-(1,1,3,3-Tetramethylbutyl)-phenol 75V, Negative-QTOFsplash10-0a4r-0590000000-ea4d2f89515c6b8f33a52021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-(1,1,3,3-Tetramethylbutyl)-phenol 45V, Negative-QTOFsplash10-0a4i-0090000000-1fce8ff30d97c03b61532021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-(1,1,3,3-Tetramethylbutyl)-phenol 30V, Negative-QTOFsplash10-0a4i-0090000000-706d0172f177e3fa56882021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(1,1,3,3-Tetramethylbutyl)-phenol 10V, Positive-QTOFsplash10-0a4i-0190000000-312caab5fa71d0dbc4ac2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(1,1,3,3-Tetramethylbutyl)-phenol 20V, Positive-QTOFsplash10-0a4i-1590000000-554843e16a1b867f14632016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(1,1,3,3-Tetramethylbutyl)-phenol 40V, Positive-QTOFsplash10-052s-5900000000-e546135869e4f5ba72312016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(1,1,3,3-Tetramethylbutyl)-phenol 10V, Negative-QTOFsplash10-0a4i-0090000000-b410576bf25ec1ab460f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(1,1,3,3-Tetramethylbutyl)-phenol 20V, Negative-QTOFsplash10-0a4i-0090000000-1705cc32a155c97241fb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(1,1,3,3-Tetramethylbutyl)-phenol 40V, Negative-QTOFsplash10-0abi-4930000000-b11aff47964eb84859192016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(1,1,3,3-Tetramethylbutyl)-phenol 10V, Negative-QTOFsplash10-0a4i-0090000000-2d8ac504a1490d38e7ad2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(1,1,3,3-Tetramethylbutyl)-phenol 20V, Negative-QTOFsplash10-0a4i-0090000000-2d8ac504a1490d38e7ad2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(1,1,3,3-Tetramethylbutyl)-phenol 40V, Negative-QTOFsplash10-060c-3910000000-0423436ad62e98639d582021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(1,1,3,3-Tetramethylbutyl)-phenol 10V, Positive-QTOFsplash10-0a4i-9560000000-47c322d85e30da643e432021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(1,1,3,3-Tetramethylbutyl)-phenol 20V, Positive-QTOFsplash10-0a4j-9100000000-935fbc45521bfac08de22021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(1,1,3,3-Tetramethylbutyl)-phenol 40V, Positive-QTOFsplash10-0a4l-9400000000-41a41008b3769ca9c9152021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
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)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal
    • Zhang, S., Liu, L...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothImmunoglobulin A nephropathy (IgAN) non progressor details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothImmunoglobulin A nephropathy (IgAN) progressor details
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)Bothautism details
FecesDetected but not QuantifiedNot QuantifiedChildren (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
FooDB 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
MarkerDB IDNot Available
Good Scents IDrw1197551
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). EAFUS: Everything Added to Food in the United States.. .