Showing Compound Card for m-Cresol (CDB005791)

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Record Information
Version1.0
Created at2020-04-27 16:56:56 UTC
Updated at2021-01-04 18:49:21 UTC
CannabisDB IDCDB005791
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Namem-Cresol
Descriptionm-Cresol or 3-Cresol also known as belongs to the class of organic compounds known as meta-Cresols. Meta-Cresols are compounds containing a meta-Cresol moiety, which consists of a benzene ring bearing one hydroxyl group at ring positions 1 and 3. m-Cresol is one of three known isomers of cresol including o-Cresol, m-Cresol and p-Cresol which differ in the position of the methyl group relative to the hydroxyl groups, on the phenol ring. m-Cresol is also classified as a methylphenol. Methylphenols are a widely occurring natural and manufactured group of aromatic organic compounds which are categorized as phenols (sometimes called phenolics). m-Cresol with a melting point of 11 °C ((52 °F; 284 K) is a colourless, viscous liquid that is water soluble. It has a medicinal, woody or phenolic odor. In the cosmetic industry it is used as an antimicrobial agent and a perfuming agent. It is used as an intermediate in the production of other chemicals. m-Cresol is traditionally extracted from coal tar, the volatile materials obtained in the production of coke from (bituminous) coal. Like other types of phenols, cresols are slowly oxidized by long exposure to air and the impurities often give cresols a yellowish to brownish red tint. Cresols have an odor characteristic to that of other simple phenols, reminiscent to some of a "medicine" smell. 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. Skin contact with high levels of cresols can burn the skin and damage the kidneys, liver, blood, brain, and lungs. In the past, cresol solutions have been used as antiseptics in surgery, but they have been largely displaced in this role by less toxic compounds. m-Cresol is used as a pesticide, as an antiseptic, and in the synthesis of vitamin E ( Ref:DOI ). m-Cresol is found in wood and tobacco smoke, car exhaust and in wood preservatives such as creosote. m-Cresol is also naturally present in a number of plants and plant foods. Among plants, m-Cresol has been detected in asparagus, coffee, jasmin, tea and myrrh oil. m-Cresol is one of several phenolic compounds found in cannabis smoke and is formed during the combustion of cannabis ( Ref:DOI ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
1-Hydroxy-3-methylbenzeneChEBI
3-CresolChEBI
3-HydroxytolueneChEBI
3-MethylphenolChEBI
m-KresolChEBI
m-MethylphenolChEBI
Meta-cresolChEBI
MetacresolChEBI
3-Cresol, calcium salt(1:2)MeSH
3-Cresol, sodium saltMeSH
3-PhenylphenolChEBI, HMDB
m-Cresylic acidHMDB
m-HydroxytolueneHMDB
m-OxytolueneHMDB
m-ToluolHMDB
m-CresolKEGG
Chemical FormulaC7H8O
Average Molecular Weight108.14
Monoisotopic Molecular Weight108.0575
IUPAC Name3-methylphenol
Traditional NameM-cresol
CAS Registry Number108-39-4
SMILES
CC1=CC(O)=CC=C1
InChI Identifier
InChI=1S/C7H8O/c1-6-3-2-4-7(8)5-6/h2-5,8H,1H3
InChI KeyRLSSMJSEOOYNOY-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as meta cresols. These are aromatic compounds containing a meta-cresol moiety, which consists of a benzene ring bearing a methyl group and a hydroxyl group at ring positions 1 and 3, respectively.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassCresols
Direct ParentMeta cresols
Alternative Parents
Substituents
  • M-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

Route of exposure:

Source:

Biological location:

Role

Environmental role:

Industrial application:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point11.8 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility22.7 mg/mL at 25 °CNot Available
logP1.96HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
logP1.93ALOGPS
logP2.18ChemAxon
logS-0.63ALOGPS
pKa (Strongest Acidic)10.13ChemAxon
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
Polarizability11.91 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-f9433af649d30cc0e3172014-09-20View Spectrum
GC-MSm-Cresol, non-derivatized, GC-MS Spectrumsplash10-0a4i-6900000000-f2082b2d78602454887cSpectrum
GC-MSm-Cresol, non-derivatized, GC-MS Spectrumsplash10-0a4i-9700000000-987a7fd82a03c828f2f6Spectrum
GC-MSm-Cresol, non-derivatized, GC-MS Spectrumsplash10-0a4i-5900000000-80356192ec6d2f2cce17Spectrum
GC-MSm-Cresol, non-derivatized, GC-MS Spectrumsplash10-014l-3900000000-5be628cfaed43892ecb6Spectrum
GC-MSm-Cresol, non-derivatized, GC-MS Spectrumsplash10-0a4i-6900000000-f2082b2d78602454887cSpectrum
GC-MSm-Cresol, non-derivatized, GC-MS Spectrumsplash10-0a4i-9700000000-987a7fd82a03c828f2f6Spectrum
GC-MSm-Cresol, non-derivatized, GC-MS Spectrumsplash10-0a4i-5900000000-80356192ec6d2f2cce17Spectrum
GC-MSm-Cresol, non-derivatized, GC-MS Spectrumsplash10-014l-3900000000-5be628cfaed43892ecb6Spectrum
Predicted GC-MSm-Cresol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-6900000000-b8ad5789d64b1436f653Spectrum
Predicted GC-MSm-Cresol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-01b9-7900000000-bea1778da40d4c1353e5Spectrum
Predicted GC-MSm-Cresol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSm-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-4900000000-ff165ee98ef540125c4f2012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00kf-9000000000-606fcb6bc90a29dd87282012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014i-9000000000-dcdf60701ebd4f253aff2012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (VARIAN MAT-44) , Positivesplash10-0a4i-6900000000-8a57217dc9acf65664ce2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6L) , Positivesplash10-0a4i-9700000000-987a7fd82a03c828f2f62012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-0a4i-5900000000-80356192ec6d2f2cce172012-08-31View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-50eeee8ccda679df83362016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1900000000-8d97f02d4ffa2f7ea5d72016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-9100000000-5118914f1ab03a16ca6e2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-a61d3231658626b2b3932016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-373e69629866322cc1762016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9700000000-c3be74dad978cee7d1522016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-3f09649991cc4cfcf1ec2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-4900000000-058b7146c5399581303c2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9000000000-1ab6752f7f06666002632021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-3900000000-1564c33b741bc83530e82021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-054o-9200000000-627147be2fad4471903e2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014u-9000000000-4f6fdf895856dea20b9e2021-09-24View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 400 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 IDHMDB0002048
DrugBank IDDB01776
Phenol Explorer Compound IDNot Available
FoodDB IDFDB008788
KNApSAcK IDC00035128
Chemspider ID21105871
KEGG Compound IDC01467
BioCyc IDCPD-112
BiGG IDNot Available
Wikipedia LinkM-cresol
METLIN IDNot Available
PubChem Compound342
PDB IDNot Available
ChEBI ID17231
References
General ReferencesNot Available