Showing Compound Card for 2,4-di-tert-Butylphenol (CDB000519)

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Record Information
Version1.0
Created at2020-03-19 00:41:26 UTC
Updated at2020-11-18 16:35:14 UTC
CannabisDB IDCDB000519
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name2,4-di-tert-Butylphenol
Description2,4-Di-tert-Butylphenol, also known as 2,4-DTBP, is a dibutylated derivative of phenol, with two isobutyl moieties positioned at C-2 and C-4. 2,4-di-tert-butylphenol is an organic compound with the structural formula 2,4-((CH3)3C)2C6H3OH. 2,4-Di-tert-butylphenol is a synthetic phenolic antioxidant (SPA). SPAs are a family of chemicals used widely in foods, polymers, and cosmetics as radical scavenging agents that slow down degradation due to oxidation. Given their widespread use, human exposure is unavoidable and there is public concern regarding environmental contamination by these chemicals. 2,4-Di-tert-butylphenol has been detected at extremely high concentrations in human urine (PMID: 31265952 ) and it has also been identified as a volatile component of cannabis samples from police seizures (PMID: 26657499 ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
1-Hydroxy-2,4-di-tert-butylbenzeneChEBI
2,4-Bis(1,1'-dimethylethyl)phenolChEBI
2,4-Bis(1,1-dimethylethyl)-phenolChEBI
2,4-Bis(1,1-dimethylethyl)phenolChEBI
2,4-Bis(tert-butyl)phenolChEBI
2,4-Di-t-butylphenolChEBI
2,4-Tert-butylphenolChEBI
2,4-DTBPHMDB
2,4-Di-tert-butyl-phenolHMDB
2,4-Di-tert-butylhydroxybenzeneHMDB
DBPHMDB
2,4-Di-tert-butylphenolMeSH
Chemical FormulaC14H22O
Average Molecular Weight206.33
Monoisotopic Molecular Weight206.1671
IUPAC Name2,4-di-tert-butylphenol
Traditional Name2,4-di-T-butylphenol
CAS Registry Number96-76-4
SMILES
CC(C)(C)C1=CC(=C(O)C=C1)C(C)(C)C
InChI Identifier
InChI=1S/C14H22O/c1-13(2,3)10-7-8-12(15)11(9-10)14(4,5)6/h7-9,15H,1-6H3
InChI KeyICKWICRCANNIBI-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 DescriptorsNot Available
Ontology
Disposition

Source:

Biological location:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point56.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.035 mg/mL at 25 °CNot Available
logP5.19Not Available
Predicted Properties
PropertyValueSource
logP4.91ALOGPS
logP4.76ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)10.87ChemAxon
pKa (Strongest Basic)-5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity65.37 m³·mol⁻¹ChemAxon
Polarizability25.32 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS2,4-di-tert-Butylphenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0007-2900000000-994efdbc7327235976d4Spectrum
Predicted GC-MS2,4-di-tert-Butylphenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Orbitrap 12V, negativesplash10-0a4i-0190000000-3b46ce20e0aa321154dc2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 14V, negativesplash10-0a4i-0390000000-42dfd2f16a89dc8f1a262020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 15V, negativesplash10-052r-0960000000-3c45ce0c7da2c97bcd2d2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 18V, negativesplash10-000i-0900000000-6c4cc4e06434f3426c8a2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 21V, negativesplash10-000i-0900000000-2061acc2d80b208314752020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 23V, negativesplash10-0079-0900000000-58a40377d6b1ebd9809a2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 14V, negativesplash10-052r-0940000000-7ca18c8b304176445f952020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 11V, negativesplash10-000i-0900000000-9cdec94bb4a70585be7e2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 13V, negativesplash10-000i-0900000000-77b969a7a062d07d4a2c2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 14V, negativesplash10-00dr-0900000000-1ae27e24efb9b6d274802020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - 90V, Negativesplash10-000i-0920000000-1f2e6c1d05a0843dc24b2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 15V, Negativesplash10-0a4i-0090000000-587e608db055a05c750e2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 75V, Negativesplash10-0a4r-0590000000-9e49713bb9c1507f052f2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 60V, Negativesplash10-0a4i-0190000000-74392b748884c07a591e2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0a4i-0090000000-706d0172f177e3fa56882021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 45V, Negativesplash10-0a4i-0090000000-1fce8ff30d97c03b61532021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-0a4i-0090000000-fa629e4ccce258736b822021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0190000000-37258e73d881ceee652e2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0590000000-44967cd8d168df989c772016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06vl-1910000000-8f9334c5936fcfdd60072016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0090000000-ce4ef5e9c3c72c4f8bca2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0090000000-cc6d8e07388ae5bf0b4f2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4s-1930000000-df61bac84fea752cf5282016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0090000000-2d8ac504a1490d38e7ad2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0090000000-2d8ac504a1490d38e7ad2021-09-22View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0013816
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00052597
Chemspider ID7037
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound7311
PDB IDNot Available
ChEBI ID89188
References
General References
  1. Liu R, Mabury SA: Unexpectedly high concentrations of 2,4-di-tert-butylphenol in human urine. Environ Pollut. 2019 Sep;252(Pt B):1423-1428. doi: 10.1016/j.envpol.2019.06.077. Epub 2019 Jun 21. [PubMed:31265952 ]
  2. 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 ]