Showing Compound Card for 2,4,6-Trimethylphenol (CDB000520)

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Record Information
Version1.0
Created at2020-03-19 00:41:30 UTC
Updated at2020-12-07 19:07:29 UTC
CannabisDB IDCDB000520
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name2,4,6-Trimethylphenol
Description2,4,6-Trimethylphenol, also known as Mesitol, belongs to the class of organic compounds known as para-cresols. Para cresols are compounds containing a para-cresol moiety, which consists of a benzene ring bearing one hydroxyl group at ring positions 1 and a methyl group at position 4 (para-hydroxytoluene). 2,4,6-Trimethylphenol is a mild and phenolic tasting compound. 2,4,6-Trimethylphenol is an aromatic chemical compound having three methyl groups and one hydroxy group. The name and structure of mesitol derives from the combination of mesitylene and phenol. 2,4,6-Trimethylphenol or Mesitol can be obtained by reaction of mesitylene with peroxomonophosphoric acid. Mesitol is listed by the FDA as being used as a food additive. Mesitol has also been detected in cannabis samples obtained in police seizures (PMID: 26657499 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
246-Trimethyl-phenolChEMBL, HMDB
246-TrimethylphenolChEMBL, HMDB
1,3,5-TrimethylphenolHMDB
1-Hydroxy-2,4,6-trimethylbenzeneHMDB
2,4, 6-TrimethylphenolHMDB
2,4,6-Trimethyl-phenolHMDB
2,4,6-TrimethylofenolHMDB
2,4,6-TrimetylofenolHMDB
2-Hydroxy-1,3,5-trimethyl-benzeneHMDB
2-HydroxymesityleneHMDB
BENZENE,1-hydroxy,2,4,6-trimethylHMDB
MesitolHMDB
Mesityl alcoholHMDB
Chemical FormulaC9H12O
Average Molecular Weight136.19
Monoisotopic Molecular Weight136.0888
IUPAC Name2,4,6-trimethylphenol
Traditional Name2,4,6-trimethylphenol
CAS Registry Number527-60-6
SMILES
CC1=CC(C)=C(O)C(C)=C1
InChI Identifier
InChI=1S/C9H12O/c1-6-4-7(2)9(10)8(3)5-6/h4-5,10H,1-3H3
InChI KeyBPRYUXCVCCNUFE-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as para cresols. Para cresols are compounds containing a para cresol moiety, which consists of a benzene ring bearing one hydroxyl group at ring positions 1 and 4.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassCresols
Direct ParentPara cresols
Alternative Parents
Substituents
  • P-cresol
  • O-cresol
  • Monocyclic benzene moiety
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location:

Source:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point73 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.2 mg/mL at 25 °CNot Available
logP2.73Not Available
Predicted Properties
PropertyValueSource
logP2.72ALOGPS
logP3.21ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)11.07ChemAxon
pKa (Strongest Basic)-5.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity43.16 m³·mol⁻¹ChemAxon
Polarizability16.05 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MS2,4,6-Trimethylphenol, non-derivatized, GC-MS Spectrumsplash10-0079-2900000000-96d1b2eeedae4adc640dSpectrum
GC-MS2,4,6-Trimethylphenol, non-derivatized, GC-MS Spectrumsplash10-0079-2900000000-96d1b2eeedae4adc640dSpectrum
Predicted GC-MS2,4,6-Trimethylphenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000i-1900000000-9fd27842b0a4a1475274Spectrum
Predicted GC-MS2,4,6-Trimethylphenol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-059f-5910000000-2aec95a3096e870c6038Spectrum
Predicted GC-MS2,4,6-Trimethylphenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2,4,6-Trimethylphenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-72093199016add63b8492016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-9848ab98823f9fcd40452016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-066u-9500000000-25827873c1f6da0766cb2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-778323f3118b30fc4b932016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-bc4e69bccb38d1b7ac512016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kr-5900000000-be2de5c5660d4ed4b5762016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-3d153ee27562ca42735c2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-3d153ee27562ca42735c2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-02t9-9700000000-a4696d84f76264ebd8a52021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-c195f03247d70f942ba62021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0670-8900000000-67f05b7b27768b2c2e1c2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01di-9200000000-8c4e16d62bdc2c9a32c12021-09-24View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0032544
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB010421
KNApSAcK IDC00052591
Chemspider ID10248
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10698
PDB IDNot Available
ChEBI IDNot Available
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 ]