Showing Compound Card for 4-tert-Butylphenol (CDB000656)

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Record Information
Version1.0
Created at2020-03-19 00:49:18 UTC
Updated at2020-12-07 19:07:37 UTC
CannabisDB IDCDB000656
Secondary Accession NumbersNot Available
Cannabis Compound 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 a leather and oakmoss tasting compound. 4-tert-Butylphenol has been detected in herbs and spices. It has also been reported to a volatile component of cannabis plants (PMID: 26657499 ). 4-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 (PMID: 10761994 ). However, at the levels of concentration expected to be present in plant tissues, p-tert-butylphenol represents an insignificant threat to human health.
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 Weight150.22
Monoisotopic Molecular Weight150.1045
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
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-000i-5900000000-d83739407ea92534ecaf2014-09-20View Spectrum
GC-MS4-tert-Butylphenol, non-derivatized, GC-MS Spectrumsplash10-000i-8900000000-fcc9d5515e40bf2ce9bfSpectrum
GC-MS4-tert-Butylphenol, non-derivatized, GC-MS Spectrumsplash10-000i-2900000000-4db3c9778d301443456dSpectrum
GC-MS4-tert-Butylphenol, non-derivatized, GC-MS Spectrumsplash10-0002-0910000000-5f1bfd35cf8deb78b98cSpectrum
GC-MS4-tert-Butylphenol, non-derivatized, GC-MS Spectrumsplash10-000i-8900000000-fcc9d5515e40bf2ce9bfSpectrum
GC-MS4-tert-Butylphenol, non-derivatized, GC-MS Spectrumsplash10-000i-2900000000-4db3c9778d301443456dSpectrum
GC-MS4-tert-Butylphenol, non-derivatized, GC-MS Spectrumsplash10-0002-0910000000-5f1bfd35cf8deb78b98cSpectrum
Predicted GC-MS4-tert-Butylphenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0f7c-6900000000-e6bc03dc9e08a393382aSpectrum
Predicted GC-MS4-tert-Butylphenol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0ab9-7950000000-9a3eb623432cc113e7c1Spectrum
Predicted GC-MS4-tert-Butylphenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS4-tert-Butylphenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Orbitrap 5V, negativesplash10-0002-0900000000-1b438e2954f692bde21c2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 6V, negativesplash10-0002-0900000000-4869d097cbf53b54eac72020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 7V, negativesplash10-0002-0900000000-eb91984e2eee362605ea2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 8V, negativesplash10-001j-0900000000-6f41817f2d53326891f52020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 9V, negativesplash10-001i-0900000000-743d3c04ea258d8d65f42020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 11V, negativesplash10-001i-0900000000-5b6aa25385985d1805642020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 12V, negativesplash10-001i-1900000000-fd9628d81ef8f4e181332020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 14V, negativesplash10-001i-2900000000-ccd8003868f8bdeccc5c2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 10V, negativesplash10-001i-0900000000-d8230f5f259df6fea0002020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 7V, negativesplash10-001i-1900000000-cfab9ce208c524adf3212020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 8V, negativesplash10-00lu-2900000000-b607a227fde521d769132020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 9V, negativesplash10-014i-3900000000-81462e4176534374f8432020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 11V, negativesplash10-014i-2900000000-13838214504729aab1272020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 12V, negativesplash10-014i-2900000000-c76ede2275038ed75b6d2020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-e180d190b00910efa3822016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-1900000000-57816f46479a4b16509f2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kmi-4900000000-4d051f92232b77a4f2222016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-22731f94c93a65d86fa72016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-af037d6638ec1135f64a2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-3900000000-c10592e6ba17dd98b6ba2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-3900000000-fceeeeb8e46c4e45273b2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9100000000-a55d19411e2dc8e43a3d2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9100000000-b8f56188be6daa978d822021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-22917433edc8ad9dbc2e2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-22917433edc8ad9dbc2e2021-09-25View Spectrum
NMR
TypeDescriptionView
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0032063
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB008772
KNApSAcK IDC00045799
Chemspider ID13846663
KEGG Compound IDC14200
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound7393
PDB IDNot Available
ChEBI ID34444
References
General References
  1. Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499 ]
  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. doi: 10.1034/j.1600-0749.2000.130107.x. [PubMed:10761994 ]