Showing Compound Card for o-Cresol (CDB005787)

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Record Information
Version1.0
Created at2020-04-27 16:56:33 UTC
Updated at2021-01-05 16:40:40 UTC
CannabisDB IDCDB005787
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Nameo-Cresol
Descriptiono-Cresol, also known as ortho-Cresol or 2-hydroxytoluene, 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. Three isomers of cresol are known, including o-Cresol, m-Cresol and p-Cresol which differ in the position of the methyl relative to the hydroxyl groups, on the phenol ring. o-Cresol exists as a colorless to white crystals. It is moderately soluble in water and has a sweet, phenolic odor. Industrially o-Cresol can be prepared from coal tar (the volatilized materials obtained in the roasting of coal to produce coke) and petroleum residues. It is used a precursor or intermediate in the production of herbicides and drugs. o-Cresol is also employed commercially as a disinfectant. In the cosmetic industry o-Cresol is used as an antimicrobial agent and as a perfuming agent. Cresols, such as o-Cresol are strong germicides, and in low concentrations they are effective disinfectants and antiseptics. Cresol solutions are used as household cleaners and disinfectants, perhaps most famously under the trade name Lysol. They are also used in low concentrations in sheep-dips (disinfectants often containing insecticides and pesticides). o-Cresol is an important component of creosote, a wood preservative produced as a by-product of coal tar distillation. Cresols give creosote its antibacterial and insecticidal properties, as well as its toxicity and its ability to irritate bare skin. Most exposures to cresols are at very low levels that are not harmful. When cresols are inhaled, ingested, or applied to the skin at very high levels, they can be very harmful. Effects observed in people include irritation and burning of skin, eyes, mouth, and throat; abdominal pain and vomiting; heart damage; anemia; liver and kidney damage; facial paralysis; coma; and death. Breathing high levels of cresols for a short time results in irritation of the nose and throat. Aside from these effects, very little is known about the effects of breathing cresols, for example, at lower levels over longer times. Ingesting high levels results in kidney problems, mouth and throat burns, abdominal pain, vomiting, and effects on the blood and nervous system. Ingestion of o-Cresol causes intense burning of the mouth and throat, followed by marked abdominal pain and distress. The minimum lethal dose of cresol by mouth is about 2 g (PMID 15040915 ). Skin contact with high levels of cresols can burn the skin and damage the kidneys, liver, blood, brain, and lungs. o-Cresol is also produced naturally at low levels and is found in a number of plants and animals including the castor sacks of beavers. Among plants, o-Cresol has been detected in peppermints, asparagus, coffee, mustard, garden tomato (var.), tea, pepper (C. annuum), orange bell peppers, and sour cherries. This could make o-Cresol a potential biomarker for the consumption of these foods. o-Cresol can be routinely detected in humans. It is a minor urinary metabolite of toluene, a widely used chemical with known neurotoxicological properties. (PMID: 15687000 ). As a result, o-Cresol is commonly used to assess human inhalation exposures to toluene (PMID: 25601989 ). o-Cresol is also produced from tobacco smoke and auto exhaust and the sulfate derivative of o-Cresol (o-Cresylsulfate) can be detected in blood and urine (PMID: 26721601 ). o-Cresol is one of several phenolic compounds found in cannabis smoke and is formed during the combustion of cannabis ( Ref:DOI ).
Structure
Thumb
MOLSDFPDBSMILESInChI
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, MeSH
O-HydroxytolueneHMDB
O-MethylphenylolHMDB
O-OxytolueneHMDB
O-ToluolHMDB
2-Cresol, potassium saltMeSH, HMDB
2-Cresol, ammonium saltMeSH, HMDB
2-Cresol, sodium saltMeSH, HMDB
Chemical FormulaC7H8O
Average Molecular Weight108.14
Monoisotopic Molecular Weight108.0575
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

Health effect:

Disposition

Source:

Route of exposure:

Biological location:

Role

Environmental role:

Industrial application:

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
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 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity33.08 m³·mol⁻¹ChemAxon
Polarizability11.83 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0a4i-9800000000-c390212681445a7e27272014-09-20View Spectrum
GC-MSo-Cresol, non-derivatized, GC-MS Spectrumsplash10-0a6r-9600000000-5a01d451557a1b35332aSpectrum
GC-MSo-Cresol, non-derivatized, GC-MS Spectrumsplash10-0pbi-9200000000-be9e6e56af8374e66bebSpectrum
GC-MSo-Cresol, non-derivatized, GC-MS Spectrumsplash10-0a4i-7900000000-c8eb63e9fe9da99fda0fSpectrum
GC-MSo-Cresol, non-derivatized, GC-MS Spectrumsplash10-00ko-5900000000-cef3087dea0c431cce4bSpectrum
GC-MSo-Cresol, non-derivatized, GC-MS Spectrumsplash10-0a6r-9600000000-5a01d451557a1b35332aSpectrum
GC-MSo-Cresol, non-derivatized, GC-MS Spectrumsplash10-0pbi-9200000000-be9e6e56af8374e66bebSpectrum
GC-MSo-Cresol, non-derivatized, GC-MS Spectrumsplash10-0a4i-7900000000-c8eb63e9fe9da99fda0fSpectrum
GC-MSo-Cresol, non-derivatized, GC-MS Spectrumsplash10-00ko-5900000000-cef3087dea0c431cce4bSpectrum
Predicted GC-MSo-Cresol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-6900000000-7ba7c816e0edce6b772fSpectrum
Predicted GC-MSo-Cresol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-06di-7900000000-db9d20fae81c588496feSpectrum
Predicted GC-MSo-Cresol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSo-Cresol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0a4i-5900000000-c7d0037b6de77737b7e42012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0006-9000000000-151af99851311002a3fa2012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-03y3-9000000000-260e2bcf6f7dca1a3c9c2012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (VARIAN MAT-44) , Positivesplash10-0a6r-9600000000-ac87a40c538d227b69152012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6L) , Positivesplash10-0pbi-9200000000-be9e6e56af8374e66beb2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-0a4i-7900000000-1a7cfac9452c2b14f9772012-08-31View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-5d6424b7db2e7e40d6d72016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-2900000000-e468ad1b8f28b32d72762016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ufr-9000000000-2629c90f57b18d57c59d2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-8feea1e7288d5bc80ea52016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-22006f43be347c9152922016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6u-9300000000-d3ec19098100f79d4ebd2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-3f09649991cc4cfcf1ec2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-3f09649991cc4cfcf1ec2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0i03-9100000000-267c04454ade05650a342021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-2900000000-c580eec1345db0ab90452021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002f-9000000000-923877cbbb5c2a1edb9c2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-016u-9000000000-09eba92f6442b1a88ad52021-09-22View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0002055
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
References
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. doi: 10.1016/j.forsciint.2003.10.023. [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. doi: 10.1016/j.jchromb.2004.12.029. [PubMed:15687000 ]
  3. Marchand A, Aranda-Rodriguez R, Tardif R, Nong A, Haddad S: Human inhalation exposures to toluene, ethylbenzene, and m-xylene and physiologically based pharmacokinetic modeling of exposure biomarkers in exhaled air, blood, and urine. Toxicol Sci. 2015 Apr;144(2):414-24. doi: 10.1093/toxsci/kfv009. Epub 2015 Jan 19. [PubMed:25601989 ]
  4. Gu F, Derkach A, Freedman ND, Landi MT, Albanes D, Weinstein SJ, Mondul AM, Matthews CE, Guertin KA, Xiao Q, Zheng W, Shu XO, Sampson JN, Moore SC, Caporaso NE: Cigarette smoking behaviour and blood metabolomics. Int J Epidemiol. 2016 Oct;45(5):1421-1432. doi: 10.1093/ije/dyv330. Epub 2015 Dec 31. [PubMed:26721601 ]