Record Information
Version2.0
Creation Date2014-09-11 05:20:39 UTC
Update Date2014-12-24 20:26:58 UTC
Accession NumberT3D4881
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.
Compound Type
  • Food Toxin
  • Household Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
  • Plant Toxin
Chemical Structure
Thumb
Synonyms
Synonym
1-Hydroxy-4-tert-butylbenzene
2-(4-Hydroxyphenyl)-2-methylpropane
4-(1, 1-Dimethylethyl)phenol
4-(1,1-Dimethylethyl)-Phenol
4-(1,1-Dimethylethyl)phenol
4-(1,1-Dimethylethyl)phenol, 9CI
4-t-Butylphenol
4-Tert-butyl-Phenol
4-Tert-butylphenol
4-Tertiary-butylphenol
Butylphen
FEMA 3918
Lowinox 070
Lowinox PTBT
Lowinox TBMX
p-(Tert-butyl)-Phenol
P-Sec-butylphenol
P-t-Butyl phenol
P-t-Butylphenol
P-Terc.butylfenol
p-Tert-butyl-Phenol
P-Tert-butylphenol
Para-tertiary-butylphenol
PTBP
T-Butylphenol
Ucar butylphenol 4-T
Ucar butylphenol 4-T flake
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 KeyInChIKey=QHPQWRBYOIRBIT-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
LogP3.31
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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-8900000000-fcc9d5515e40bf2ce9bf2017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-2900000000-4db3c9778d301443456d2017-09-12View Spectrum
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-0002-0910000000-5f1bfd35cf8deb78b98c2017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-8900000000-fcc9d5515e40bf2ce9bf2018-05-18View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-2900000000-4db3c9778d301443456d2018-05-18View Spectrum
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-0002-0910000000-5f1bfd35cf8deb78b98c2018-05-18View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f7c-6900000000-e6bc03dc9e08a393382a2017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0ab9-7950000000-9a3eb623432cc113e7c12017-10-06View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 5V, negativesplash10-0002-0900000000-1b438e2954f692bde21c2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 6V, negativesplash10-0002-0900000000-4869d097cbf53b54eac72020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 7V, negativesplash10-0002-0900000000-eb91984e2eee362605ea2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 8V, negativesplash10-001j-0900000000-6f41817f2d53326891f52020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 9V, negativesplash10-001i-0900000000-743d3c04ea258d8d65f42020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 11V, negativesplash10-001i-0900000000-5b6aa25385985d1805642020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 12V, negativesplash10-001i-1900000000-fd9628d81ef8f4e181332020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 14V, negativesplash10-001i-2900000000-ccd8003868f8bdeccc5c2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 10V, negativesplash10-001i-0900000000-d8230f5f259df6fea0002020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 7V, negativesplash10-001i-1900000000-cfab9ce208c524adf3212020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 8V, negativesplash10-00lu-2900000000-b607a227fde521d769132020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 9V, negativesplash10-014i-3900000000-81462e4176534374f8432020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 11V, negativesplash10-014i-2900000000-13838214504729aab1272020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 12V, negativesplash10-014i-2900000000-c76ede2275038ed75b6d2020-07-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-e180d190b00910efa3822016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-1900000000-57816f46479a4b16509f2016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kmi-4900000000-4d051f92232b77a4f2222016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-22731f94c93a65d86fa72016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-af037d6638ec1135f64a2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-3900000000-c10592e6ba17dd98b6ba2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-3900000000-fceeeeb8e46c4e45273b2021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9100000000-a55d19411e2dc8e43a3d2021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9100000000-b8f56188be6daa978d822021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-22917433edc8ad9dbc2e2021-09-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-22917433edc8ad9dbc2e2021-09-25View Spectrum
MSMass Spectrum (Electron Ionization)splash10-000i-5900000000-d83739407ea92534ecaf2014-09-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Not Available2014-09-23View Spectrum
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
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB32063
PubChem Compound ID7393
ChEMBL IDCHEMBL16217
ChemSpider ID13846663
KEGG IDC14200
UniProt IDNot Available
OMIM ID
ChEBI ID34444
BioCyc IDNot Available
CTD IDC006862
Stitch IDNot Available
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDST3D4881.pdf
General References
  1. Manga P, Sheyn D, Yang F, Sarangarajan R, Boissy RE: A role for tyrosinase-related protein 1 in 4-tert-butylphenol-induced toxicity in melanocytes: Implications for vitiligo. Am J Pathol. 2006 Nov;169(5):1652-62. [17071589 ]
  2. Thorneby-Andersson K, Sterner O, Hansson C: Tyrosinase-mediated formation of a reactive quinone from the depigmenting agents, 4-tert-butylphenol and 4-tert-butylcatechol. Pigment Cell Res. 2000 Feb;13(1):33-8. [10761994 ]
  3. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

General Function:
Zinc ion binding
Specific Function:
Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription factors, such as AP-1/c-Jun, c-Fos, ATF-2, Sp1 and Sp3, to mediate ERE-independent signaling. Ligand binding induces a conformational change allowing subsequent or combinatorial association with multiprotein coactivator complexes through LXXLL motifs of their respective components. Mutual transrepression occurs between the estrogen receptor (ER) and NF-kappa-B in a cell-type specific manner. Decreases NF-kappa-B DNA-binding activity and inhibits NF-kappa-B-mediated transcription from the IL6 promoter and displace RELA/p65 and associated coregulators from the promoter. Recruited to the NF-kappa-B response element of the CCL2 and IL8 promoters and can displace CREBBP. Present with NF-kappa-B components RELA/p65 and NFKB1/p50 on ERE sequences. Can also act synergistically with NF-kappa-B to activate transcription involving respective recruitment adjacent response elements; the function involves CREBBP. Can activate the transcriptional activity of TFF1. Also mediates membrane-initiated estrogen signaling involving various kinase cascades. Isoform 3 is involved in activation of NOS3 and endothelial nitric oxide production. Isoforms lacking one or several functional domains are thought to modulate transcriptional activity by competitive ligand or DNA binding and/or heterodimerization with the full length receptor. Essential for MTA1-mediated transcriptional regulation of BRCA1 and BCAS3. Isoform 3 can bind to ERE and inhibit isoform 1.
Gene Name:
ESR1
Uniprot ID:
P03372
Molecular Weight:
66215.45 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC507.66 uMATG_ERa_TRANSAttagene
AC505.78 uMATG_ERE_CISAttagene
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
  2. Hu JY, Aizawa T: Quantitative structure-activity relationships for estrogen receptor binding affinity of phenolic chemicals. Water Res. 2003 Mar;37(6):1213-22. [12598185 ]
  3. Dang Z: Comparison of relative binding affinities to fish and mammalian estrogen receptors: the regulatory implications. Toxicol Lett. 2010 Feb 15;192(3):298-315. doi: 10.1016/j.toxlet.2009.11.004. Epub 2009 Nov 12. [19913605 ]
General Function:
Protein homodimerization activity
Specific Function:
This is a copper-containing oxidase that functions in the formation of pigments such as melanins and other polyphenolic compounds. Catalyzes the rate-limiting conversions of tyrosine to DOPA, DOPA to DOPA-quinone and possibly 5,6-dihydroxyindole to indole-5,6 quinone.
Gene Name:
TYR
Uniprot ID:
P14679
Molecular Weight:
60392.69 Da
References
  1. Thorneby-Andersson K, Sterner O, Hansson C: Tyrosinase-mediated formation of a reactive quinone from the depigmenting agents, 4-tert-butylphenol and 4-tert-butylcatechol. Pigment Cell Res. 2000 Feb;13(1):33-8. [10761994 ]
General Function:
Zinc ion binding
Specific Function:
Binds and transactivates the retinoic acid response elements that control expression of the retinoic acid receptor beta 2 and alcohol dehydrogenase 3 genes. Transactivates both the phenobarbital responsive element module of the human CYP2B6 gene and the CYP3A4 xenobiotic response element.
Gene Name:
NR1I3
Uniprot ID:
Q14994
Molecular Weight:
39942.145 Da
References
  1. Dring AM, Anderson LE, Qamar S, Stoner MA: Rational quantitative structure-activity relationship (RQSAR) screen for PXR and CAR isoform-specific nuclear receptor ligands. Chem Biol Interact. 2010 Dec 5;188(3):512-25. doi: 10.1016/j.cbi.2010.09.018. Epub 2010 Oct 20. [20869355 ]