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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:34 UTC
Update Date2023-02-21 17:16:06 UTC
HMDB IDHMDB0002055
Secondary Accession Numbers
  • HMDB02055
Metabolite Identification
Common Nameo-Cresol
Descriptiono-Cresol is a minor urinary metabolite of toluene, O-cresol is a cresol that is phenol substituted by a methyl group at position 2. It is a minor urinary metabolite of toluene. It has a role as a human xenobiotic metabolite. It is 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 ). o-Cresol is a microbial metabolite that can be found in Pseudomonas. Besides, o-Cresol is one of the chemical compounds found in castoreum. This compound is gathered from the beaver's castor glands and found in the white cedar consumed by the beavers. Together with many other compounds, o-cresol is traditionally extracted from coal tar, the volatile materials obtained in the production of coke from coal. A similar source material is petroleum residues. These residue contains a few percent by weight of phenol and isomeric cresols. In addition to the materials derived from these natural sources, about two thirds of the Western world's supply is produced by methylation of phenol using methanol.
Structure
Thumb
Synonyms
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
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
  • 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
Physiological effect
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point29.8 °CNot Available
Boiling Point191.00 to 192.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility25.9 mg/mL at 25 °CNot Available
LogP1.95HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)Not Specified
Normal
details
UrineDetected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified17.5 (9.24-32.6) uMAdult (>18 years old)Both
Cresol poisoning
details
FecesDetected but not QuantifiedNot QuantifiedChildren (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 ]
Celiac disease
  1. Di Cagno R, De Angelis M, De Pasquale I, Ndagijimana M, Vernocchi P, Ricciuti P, Gagliardi F, Laghi L, Crecchio C, Guerzoni ME, Gobbetti M, Francavilla R: Duodenal and faecal microbiota of celiac children: molecular, phenotype and metabolome characterization. BMC Microbiol. 2011 Oct 4;11:219. doi: 10.1186/1471-2180-11-219. [PubMed:21970810 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB008785
KNApSAcK IDC00030878
Chemspider ID13835772
KEGG Compound IDC01542
BioCyc IDCPD-109
BiGG IDNot Available
Wikipedia LinkO-Cresol
METLIN IDNot Available
PubChem Compound335
PDB IDNot Available
ChEBI ID28054
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1007721
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
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 ]