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4-Methylphenol (FDB008789)

Record Information
Version1.0
Creation date2010-04-08 22:08:15 UTC
Update date2019-11-26 03:03:13 UTC
Primary IDFDB008789
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name4-Methylphenol
Descriptionp-Cresol, also known as 4-hydroxytoluene or 4-methylphenol, belongs to the class of organic compounds known as para cresols. Para cresols are compounds containing a para cresol moiety, which consists of a benzene ring bearing one hydroxyl group at ring positions 1 and 4. p-Cresol exists in all living species, ranging from bacteria to plants to humans. p-Cresol is an animal, medicinal, and mimosa tasting compound. p-Cresol is found, on average, in the highest concentration within a few different foods, such as milk (cow), peppermints (Mentha X piperita), and bilberries (Vaccinium myrtillus). p-Cresol has also been detected, but not quantified in, several different foods, such as almonds (Prunus dulcis), green tea, cherry tomatoes (Solanum lycopersicum var. cerasiforme), green vegetables, and yellow bell peppers (Capsicum annuum). This could make p-cresol a potential biomarker for the consumption of these foods. p-Cresol, with regard to humans, has been found to be associated with several diseases such as autism, nonalcoholic fatty liver disease, diarrhoea predominant irritable bowel syndrome, and enteritis; p-cresol has also been linked to the inborn metabolic disorder celiac disease. Based on a literature review a significant number of articles have been published on p-Cresol.
CAS Number106-44-5
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility23.1 g/LALOGPS
logP1.95ALOGPS
logP2.18ChemAxon
logS-0.67ALOGPS
pKa (Strongest Acidic)10.36ChemAxon
pKa (Strongest Basic)-5.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity33.08 m³·mol⁻¹ChemAxon
Polarizability11.93 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC7H8O
IUPAC name4-methylphenol
InChI IdentifierInChI=1S/C7H8O/c1-6-2-4-7(8)5-3-6/h2-5,8H,1H3
InChI KeyIWDCLRJOBJJRNH-UHFFFAOYSA-N
Isomeric SMILESCC1=CC=C(O)C=C1
Average Molecular Weight108.1378
Monoisotopic Molecular Weight108.057514878
Classification
Description Belongs to the class of organic compounds known as para cresols. Para cresols are compounds containing a para cresol moiety, which consists of a benzene ring bearing one hydroxyl group at ring positions 1 and 4.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassCresols
Direct ParentPara cresols
Alternative Parents
Substituents
  • P-cresol
  • 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

Indirect biological role:

Environmental role:

Industrial application:

Foods
  • Dairy products
  • Eggs
  • Meats

    • Grains:

    Nuts and legumes:

    Physico-Chemical Properties - Experimental
    Physico-Chemical Properties - Experimental
    PropertyValueReference
    Physical stateSolid
    Physical DescriptionNot Available
    Mass CompositionC 77.75%; H 7.46%; O 14.80%DFC
    Melting PointMp 36°DFC
    Boiling PointBp11 90°DFC
    Experimental Water Solubility21.5 mg/mL at 25 oCYALKOWSKY,SH & HE,Y (2003)
    Experimental logP1.94HANSCH,C ET AL. (1995)
    Experimental pKapKa 10.27 (25°)DFC
    Isoelectric pointNot Available
    ChargeNot Available
    Optical RotationNot Available
    Spectroscopic UV DataNot Available
    Densityd204 1.03DFC
    Refractive IndexNot Available
    Spectra
    Spectra
    EI-MS/GC-MS
    TypeDescriptionSplash KeyView
    EI-MSMass Spectrum (Electron Ionization)splash10-0a4i-6900000000-729e6f5bdb0da3ed9ded2014-09-20View Spectrum
    GC-MS4-Methylphenol, non-derivatized, GC-MS Spectrumsplash10-0a4i-5900000000-1d2bdfde621a5af9be73Spectrum
    GC-MS4-Methylphenol, non-derivatized, GC-MS Spectrumsplash10-0a4i-5900000000-b76093f53701327ab25fSpectrum
    GC-MS4-Methylphenol, non-derivatized, GC-MS Spectrumsplash10-0a4i-4900000000-7d25deb1e39c6ef4866fSpectrum
    GC-MS4-Methylphenol, non-derivatized, GC-MS Spectrumsplash10-0a4i-7900000000-15d473146e11e4b049b2Spectrum
    GC-MS4-Methylphenol, non-derivatized, GC-MS Spectrumsplash10-014l-4900000000-14fef90a661a09457976Spectrum
    GC-MS4-Methylphenol, non-derivatized, GC-MS Spectrumsplash10-0a4i-5900000000-1d2bdfde621a5af9be73Spectrum
    GC-MS4-Methylphenol, non-derivatized, GC-MS Spectrumsplash10-0a4i-5900000000-b76093f53701327ab25fSpectrum
    GC-MS4-Methylphenol, non-derivatized, GC-MS Spectrumsplash10-0a4i-4900000000-7d25deb1e39c6ef4866fSpectrum
    GC-MS4-Methylphenol, non-derivatized, GC-MS Spectrumsplash10-0a4i-7900000000-15d473146e11e4b049b2Spectrum
    GC-MS4-Methylphenol, non-derivatized, GC-MS Spectrumsplash10-014l-4900000000-14fef90a661a09457976Spectrum
    Predicted GC-MS4-Methylphenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-6900000000-27534de20ade11dd5454Spectrum
    Predicted GC-MS4-Methylphenol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-06fr-9700000000-f41dd95ca553de6bafffSpectrum
    Predicted GC-MS4-Methylphenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MS4-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-ab55ada5cae0538f383e2012-07-24View Spectrum
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0006-9000000000-385a7a99e0409c7f060d2012-07-24View Spectrum
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-02tl-9000000000-205f4e5245868e9debcc2012-07-24View Spectrum
    MS/MSLC-MS/MS Spectrum - EI-B (VARIAN MAT-44) , Positivesplash10-0a4i-5900000000-fd438231ac0ed75fdf092012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-0a4i-5900000000-b76093f53701327ab25f2012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-D-3000) , Positivesplash10-0a4i-4900000000-7d25deb1e39c6ef4866f2012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-0a4i-7900000000-0cdab17a1a95f3e65f452012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - NA 35V, negativesplash10-0a6u-9600000000-276b44cbbdb079cac7182020-07-21View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-cf0bed2b3a203309d9aa2016-09-12View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1900000000-4f20c8bd2dde845b499c2016-09-12View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fb9-9100000000-393b5f734646352622f92016-09-12View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-0c45920f40546c2d89442016-09-12View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-417774c01b748db1609d2016-09-12View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9600000000-5583b6dc3ae583b8dab02016-09-12View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-3f09649991cc4cfcf1ec2021-09-23View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-3f09649991cc4cfcf1ec2021-09-23View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-6eb0884733967edc9e6b2021-09-23View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-3900000000-621936189d60e194cefd2021-09-24View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056u-9100000000-2740c99af64b11309dfb2021-09-24View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-9000000000-1c2034d922354f5d66822021-09-24View 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
    2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
    ChemSpider ID13839082
    ChEMBL IDCHEMBL16645
    KEGG Compound IDC01468
    Pubchem Compound ID2879
    Pubchem Substance IDNot Available
    ChEBI ID17847
    Phenol-Explorer IDNot Available
    DrugBank IDDB01688
    HMDB IDHMDB01858
    CRC / DFC (Dictionary of Food Compounds) IDDXH45-J:DXH45-J
    EAFUS ID772
    Dr. Duke IDCRESOL|P-CRESOL
    BIGG IDNot Available
    KNApSAcK IDC00002645
    HET IDPCR
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    Flavornet ID106-44-5
    GoodScent IDrw1003851
    SuperScent ID2879
    Wikipedia IDP-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
    flavor48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
    hemolyticDUKE
    irritantDUKE
    parasiticideDUKE
    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
    medicine
    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
    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
    smoke
    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
    phenolic
    1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
    narcissus
    1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
    animal
    1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
    mimosa
    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.