You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2006-05-22 14:17:34 UTC
Update Date2017-03-02 21:26:51 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
2-Cresol, potassium saltMeSH
2-Cresol, ammonium saltMeSH
2-Cresol, sodium saltMeSH
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 KeyQWVGKYWNOKOFNN-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassPhenols
Direct ParentOrtho cresols
Alternative Parents
Substituents
  • O-cresol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Toluene
  • Monocyclic benzene moiety
  • Organic oxygen compound
  • 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
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
GC-MSGC-MS Spectrum - EI-Bsplash10-0a6r-9600000000-5a01d451557a1b35332aView in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-0pbi-9200000000-be9e6e56af8374e66bebView in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-0a4i-7900000000-c8eb63e9fe9da99fda0fView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-00ko-5900000000-cef3087dea0c431cce4bView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-00ko-5900000000-cef3087dea0c431cce4bView in MoNA
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
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 Quantified Not AvailableNot Available
Normal
    details
    FecesDetected but not Quantified Not SpecifiedNot Specified
    Normal
    details
    FecesDetected but not Quantified Children (1-13 years old)Not Specified
    Normal
    details
    UrineDetected but not Quantified Not 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 Quantified Children (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. [PubMed: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. [PubMed: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. [PubMed:15687000 ]