Record Information
Version1.0
Creation date2010-04-08 22:08:15 UTC
Update date2019-11-27 17:15:33 UTC
Primary IDFDB008788
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name3-Methylphenol
Descriptionm-Cresol, also known as meta-cresol or 3-hydroxytoluene, 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. m-Cresol is an extremely weak basic (essentially neutral) compound (based on its pKa). m-Cresol exists in all eukaryotes, ranging from yeast to humans. m-Cresol is a fecal, leather, and medicinal tasting compound. m-Cresol has been detected, but not quantified in, a few different foods, such as arabica coffee, asparagus, and tea. This could make m-cresol a potential biomarker for the consumption of these foods. m-Cresol is a potentially toxic compound.
CAS Number108-39-4
Structure
Thumb
Synonyms
SynonymSource
1-Hydroxy-3-methylbenzeneChEBI
3-CresolChEBI
3-HydroxytolueneChEBI
3-MethylphenolChEBI
m-KresolChEBI
m-MethylphenolChEBI
Meta-cresolChEBI
MetacresolChEBI
3-PhenylphenolHMDB
m-Cresylic acidHMDB
m-HydroxytolueneHMDB
m-OxytolueneHMDB
m-ToluolHMDB
3-Cresol, sodium saltHMDB
3-Cresol, calcium salt(1:2)HMDB
m-CresolKEGG
1-Methyl-3-hydroxybenzenebiospider
3-methyl-1-hydroxybenzenebiospider
Cresol, m-biospider
Cresol, metabiospider
FEMA 3530db_source
Hydroxy-3-methylbenzenebiospider
m-Cresol, 8CIdb_source
m-toluolbiospider
Meta-cresylic acidbiospider
Metacresol, USANdb_source
Phenol, 3-methyl-biospider
Predicted Properties
PropertyValueSource
Water Solubility25.1 g/LALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC7H8O
IUPAC name3-methylphenol
InChI IdentifierInChI=1S/C7H8O/c1-6-3-2-4-7(8)5-6/h2-5,8H,1H3
InChI KeyRLSSMJSEOOYNOY-UHFFFAOYSA-N
Isomeric SMILESCC1=CC=CC(O)=C1
Average Molecular Weight108.1378
Monoisotopic Molecular Weight108.057514878
Classification
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:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionC 77.75%; H 7.46%; O 14.80%DFC
Melting PointMp 11-12°DFC
Boiling PointBp6 80°DFC
Experimental Water Solubility22.7 mg/mL at 25 oCYALKOWSKY,SH & HE,Y (2003)
Experimental logP1.96HANSCH,C ET AL. (1995)
Experimental pKapKa 10.09 (25°)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
Densityd224 1.04DFC
Refractive Indexn20D 1.5400DFC
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-6900000000-f2082b2d78602454887cView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-9700000000-987a7fd82a03c828f2f6View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-5900000000-80356192ec6d2f2cce17View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014l-3900000000-5be628cfaed43892ecb6View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-6900000000-f2082b2d78602454887cView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-9700000000-987a7fd82a03c828f2f6View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-5900000000-80356192ec6d2f2cce17View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014l-3900000000-5be628cfaed43892ecb6View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-6900000000-b8ad5789d64b1436f653View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-01b9-7900000000-bea1778da40d4c1353e5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0a4i-4900000000-ff165ee98ef540125c4fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00kf-9000000000-606fcb6bc90a29dd8728View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014i-9000000000-dcdf60701ebd4f253affView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (VARIAN MAT-44) , Positivesplash10-0a4i-6900000000-8a57217dc9acf65664ceView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6L) , Positivesplash10-0a4i-9700000000-987a7fd82a03c828f2f6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-0a4i-5900000000-80356192ec6d2f2cce17View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-50eeee8ccda679df8336View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1900000000-8d97f02d4ffa2f7ea5d7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-9100000000-5118914f1ab03a16ca6eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-a61d3231658626b2b393View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-373e69629866322cc176View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9700000000-c3be74dad978cee7d152View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0a4i-9800000000-f9433af649d30cc0e317View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
ChemSpider ID21105871
ChEMBL IDCHEMBL298312
KEGG Compound IDC01467
Pubchem Compound ID342
Pubchem Substance IDNot Available
ChEBI ID17231
Phenol-Explorer IDNot Available
DrugBank IDDB01776
HMDB IDHMDB02048
CRC / DFC (Dictionary of Food Compounds) IDDXH39-K:DXH39-K
EAFUS ID770
Dr. Duke IDM-CRESOL
BIGG IDNot Available
KNApSAcK IDC00035128
HET IDCRS
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID108-39-4
GoodScent IDrw1007701
SuperScent ID342
Wikipedia IDm-Cresol
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti septic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
fumigant39276 A volatile or volatilizable chemical compound utilized for control of pests in buildings, soil, grain, as well as during processing of goods to be imported or exported to prevent transfer of exotic organisms.DUKE
hemolyticDUKE
irritantDUKE
parasiticideDUKE
perfumery48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
rodenticide33288 A substance used to destroy rodent pests.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
fecal
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
plastic
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
medicinal
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
medical
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
woody
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
leather
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
phenolic
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).