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Record Information
Version3.6
Creation Date2006-05-22 14:17:34 UTC
Update Date2016-02-11 01:05:15 UTC
HMDB IDHMDB02055
Secondary Accession NumbersNone
Metabolite Identification
Common Nameo-Cresol
Descriptiono-Cresol is a minor urinary metabolite of toluene, a widely used chemical with neurotoxicological properties. (PMID: 15687000 ). o-Cresol is used commercially as a disinfectant. Exposure may occur by inhalation, by cutaneous adsorption or by oral ingestion. o-Cresol denature and precipitate cellular proteins and thus may rapidly cause poisoning. o-Cresol is metabolized by conjugation and oxidation. Ingestion of o-Cresol cause intense burning of mouth and throat, followed by marked abdominal pain and distress. The minimum lethal dose of cresol by mouth is about 2 g. (PMID 15040915 ).
Structure
Thumb
Synonyms
ValueSource
1-Hydroxy-2-methylbenzeneChEBI
2-CresolChEBI
2-Hydroxy-1-methylbenzeneChEBI
2-HydroxytolueneChEBI
O-Cresylic acidChEBI
O-KresolChEBI
O-MethylphenolChEBI
ortho-CresolChEBI
OrthocresolChEBI
O-CresylateGenerator
1-Methyl-2-hydroxybenzeneHMDB
2-MethylphenolHMDB
O-HydroxytolueneHMDB
O-MethylphenylolHMDB
O-OxytolueneHMDB
O-ToluolHMDB
Chemical FormulaC7H8O
Average Molecular Weight108.1378
Monoisotopic Molecular Weight108.057514878
IUPAC Name2-methylphenol
Traditional Nameo-cresol
CAS Registry Number95-48-7
SMILES
CC1=CC=CC=C1O
InChI Identifier
InChI=1S/C7H8O/c1-6-4-2-3-5-7(6)8/h2-5,8H,1H3
InChI KeyInChIKey=QWVGKYWNOKOFNN-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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
ClassBenzene and substituted derivatives
Sub ClassPhenols and derivatives
Direct ParentOrtho cresols
Alternative Parents
Substituents
  • O-cresol
  • Toluene
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Microbial
  • Toxin/Pollutant
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Membrane (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point29.8 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility25.9 mg/mL at 25 °CNot Available
LogP1.95HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility27.5 mg/mLALOGPS
logP1.89ALOGPS
logP2.18ChemAxon
logS-0.59ALOGPS
pKa (Strongest Acidic)10.37ChemAxon
pKa (Strongest Basic)-5.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity33.08 m3·mol-1ChemAxon
Polarizability11.83 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0a4i-5900000000-c7d0037b6de77737b7e4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0006-9000000000-151af99851311002a3faView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-03y3-9000000000-260e2bcf6f7dca1a3c9cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (VARIAN MAT-44) , Positivesplash10-0a6r-9600000000-ac87a40c538d227b6915View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6L) , Positivesplash10-0pbi-9200000000-be9e6e56af8374e66bebView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-0a4i-7900000000-1a7cfac9452c2b14f977View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
MSMass Spectrum (Electron Ionization)splash10-0a4i-9800000000-c390212681445a7e2727View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Feces
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot Available
Normal
  • Not Applicable
details
FecesDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
FecesDetected but not QuantifiedNot ApplicableChildren (1-13 years old)Not Specified
Normal
details
UrineDetected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified17.5 (9.24-32.6) uMAdult (>18 years old)Both
Cresol poisoning
details
FecesDetected but not QuantifiedNot ApplicableChildren (1-13 years old)Not Specified
Treated celiac disease
details
Associated Disorders and Diseases
Disease References
Cresol poisoning IBS
  1. Boatto G, Nieddu M, Carta A, Pau A, Lorenzoni S, Manconi P, Serra D: Determination of phenol and o-cresol by GC/MS in a fatal poisoning case. Forensic Sci Int. 2004 Jan 28;139(2-3):191-4. [15040915 ]
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB008785
KNApSAcK IDC00030878
Chemspider ID13835772
KEGG Compound IDC01542
BioCyc IDCPD-109
BiGG IDNot Available
Wikipedia Linko-Cresol
NuGOwiki LinkHMDB02055
Metagene LinkHMDB02055
METLIN IDNot Available
PubChem Compound335
PDB IDJZ0
ChEBI ID28054
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Boatto G, Nieddu M, Carta A, Pau A, Lorenzoni S, Manconi P, Serra D: Determination of phenol and o-cresol by GC/MS in a fatal poisoning case. Forensic Sci Int. 2004 Jan 28;139(2-3):191-4. [15040915 ]
  2. Fustinoni S, Mercadante R, Campo L, Scibetta L, Valla C, Foa V: Determination of urinary ortho- and meta-cresol in humans by headspace SPME gas chromatography/mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Mar 25;817(2):309-17. [15687000 ]