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2-Methylphenol (FDB008785)

Record Information
Version1.0
Creation date2010-04-08 22:08:15 UTC
Update date2019-11-26 03:03:12 UTC
Primary IDFDB008785
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name2-Methylphenol
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. o-Cresol exists in all living species, ranging from bacteria to plants to humans. o-Cresol is a medicinal, musty, and phenolic tasting compound. o-Cresol is found, on average, in the highest concentration within beer and peppermints (Mentha X piperita). o-Cresol has also been detected, but not quantified in, several different foods, such as herbal tea, garden tomato (var.), green bell peppers (Capsicum annuum), asparagus (Asparagus officinalis), and arabica coffees (Coffea arabica). This could make O-cresol a potential biomarker for the consumption of these foods. o-Cresol, with regard to humans, has been found to be associated with the diseases such as cresol poisoning ibs; O-cresol has also been linked to the inborn metabolic disorder celiac disease. Based on a literature review a small amount of articles have been published on o-Cresol.
CAS Number95-48-7
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility27.5 g/LALOGPS
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
Chemical FormulaC7H8O
IUPAC name2-methylphenol
InChI IdentifierInChI=1S/C7H8O/c1-6-4-2-3-5-7(6)8/h2-5,8H,1H3
InChI KeyQWVGKYWNOKOFNN-UHFFFAOYSA-N
Isomeric SMILESCC1=CC=CC=C1O
Average Molecular Weight108.1378
Monoisotopic Molecular Weight108.057514878
Classification
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:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 77.75%; H 7.46%; O 14.80%DFC
Melting PointMp 30°DFC
Boiling PointBp6 70°DFC
Experimental Water Solubility25.9 mg/mL at 25 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP1.95HANSCH,C ET AL. (1995)
Experimental pKapKa 10.32 (25°)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
Densityd204 1.05DFC
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0a4i-9800000000-c390212681445a7e27272014-09-20View Spectrum
GC-MS2-Methylphenol, non-derivatized, GC-MS Spectrumsplash10-0a6r-9600000000-5a01d451557a1b35332aSpectrum
GC-MS2-Methylphenol, non-derivatized, GC-MS Spectrumsplash10-0pbi-9200000000-be9e6e56af8374e66bebSpectrum
GC-MS2-Methylphenol, non-derivatized, GC-MS Spectrumsplash10-0a4i-7900000000-c8eb63e9fe9da99fda0fSpectrum
GC-MS2-Methylphenol, non-derivatized, GC-MS Spectrumsplash10-00ko-5900000000-cef3087dea0c431cce4bSpectrum
GC-MS2-Methylphenol, non-derivatized, GC-MS Spectrumsplash10-0a6r-9600000000-5a01d451557a1b35332aSpectrum
GC-MS2-Methylphenol, non-derivatized, GC-MS Spectrumsplash10-0pbi-9200000000-be9e6e56af8374e66bebSpectrum
GC-MS2-Methylphenol, non-derivatized, GC-MS Spectrumsplash10-0a4i-7900000000-c8eb63e9fe9da99fda0fSpectrum
GC-MS2-Methylphenol, non-derivatized, GC-MS Spectrumsplash10-00ko-5900000000-cef3087dea0c431cce4bSpectrum
Predicted GC-MS2-Methylphenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-6900000000-7ba7c816e0edce6b772fSpectrum
Predicted GC-MS2-Methylphenol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-06di-7900000000-db9d20fae81c588496feSpectrum
Predicted GC-MS2-Methylphenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2-Methylphenol, 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
ChemSpider ID13835772
ChEMBL IDCHEMBL46931
KEGG Compound IDC01542
Pubchem Compound ID335
Pubchem Substance IDNot Available
ChEBI ID28054
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB02055
CRC / DFC (Dictionary of Food Compounds) IDDXH33-E:DXH33-E
EAFUS ID771
Dr. Duke IDO-CRESOL
BIGG IDNot Available
KNApSAcK IDC00030878
HET IDJZ0
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID95-48-7
GoodScent IDrw1007721
SuperScent ID335
Wikipedia IDo-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
allelochemicDUKE
anti mutagenicDUKE
anti septic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.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
phenol
  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
musty
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
  2. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
medicinal
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
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).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.