Record Information
Version1.0
Creation date2010-04-08 22:06:33 UTC
Update date2019-11-26 03:00:24 UTC
Primary IDFDB005153
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name2,3,5-Trimethylphenol
Description2,3,5-trimethylphenol, also known as 1-hydroxy-2,3,5-trimethylbenzene or isopseudocumenol, is a member of the class of compounds known as ortho cresols. Ortho cresols are organic compounds containing an ortho-cresol moiety, which consists of a benzene bearing one hydroxyl group at ring positions 1 and 2, respectively. 2,3,5-trimethylphenol is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). 2,3,5-trimethylphenol can be synthesized from 1,2,4-trimethylbenzene. 2,3,5-trimethylphenol can also be synthesized into 2,3,5-trimethylphenyl methylcarbamate. 2,3,5-trimethylphenol can be found in arabica coffee, which makes 2,3,5-trimethylphenol a potential biomarker for the consumption of this food product.
CAS Number697-82-5
Structure
Thumb
Synonyms
SynonymSource
1-Hydroxy-2,3,5-trimethylbenzeneChEBI
IsopseudocumenolChEBI
1-Hydroxy-2, 3,5-trimethylbenzenebiospider
6-HYDROXYPSEUDOCUMENEbiospider
Phenol, 2,3,5-trimethyl-biospider
Phenol, 2,3,5(or 3,4,5)-trimethyl-biospider
Trimethylphenolbiospider
Predicted Properties
PropertyValueSource
Water Solubility1.88 g/LALOGPS
logP2.73ALOGPS
logP3.21ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)10.57ChemAxon
pKa (Strongest Basic)-5.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity43.16 m³·mol⁻¹ChemAxon
Polarizability15.99 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC9H12O
IUPAC name2,3,5-trimethylphenol
InChI IdentifierInChI=1S/C9H12O/c1-6-4-7(2)8(3)9(10)5-6/h4-5,10H,1-3H3
InChI KeyOGRAOKJKVGDSFR-UHFFFAOYSA-N
Isomeric SMILESCC1=CC(C)=C(C)C(O)=C1
Average Molecular Weight136.191
Monoisotopic Molecular Weight136.088815006
Classification
Description belongs to the class of organic compounds known as ortho cresols. These are organic compounds containing an ortho-cresol moiety, which consists of a benzene bearing one hydroxyl group at ring positions 1 and 2, respectively.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassCresols
Direct ParentOrtho cresols
Alternative Parents
Substituents
  • O-cresol
  • M-cresol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting Point93.5 oC
Boiling PointNot Available
Experimental Water Solubility0.762 mg/mL at 25 oCSHIU,WY et al. (1994)
Experimental logPNot Available
Experimental pKa10.7
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-11dc079713fe4f8a30e5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-2900000000-643b5cb3158513fa0e94JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uxu-9200000000-db6bd8d7be6c21152ee9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-a6e89cf53591b1cabedaJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-a7ec12fa15ec82f59e74JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kr-9800000000-10d502c51c239d8d9c63JSpectraViewer
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID12769
Pubchem Substance IDNot Available
ChEBI ID38570
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke ID2,3,5-TRIMETHYLPHENOL
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).