Record Information
Version1.0
Creation date2010-04-08 22:08:15 UTC
Update date2019-11-27 17:15:33 UTC
Primary IDFDB008789
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name4-Methylphenol
Descriptionp-Cresol, also known as 4-methylphenol or paracresol, 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 is an extremely weak basic (essentially neutral) compound (based on its pKa). p-Cresol exists in all living species, ranging from bacteria 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, and bilberries. p-Cresol has also been detected, but not quantified in, several different foods, such as orange bell peppers, cherry tomato, green vegetables, highbush blueberries, and tarragons. This could make p-cresol a potential biomarker for the consumption of these foods. p-Cresol is a potentially toxic compound.
CAS Number106-44-5
Structure
Thumb
Synonyms
SynonymSource
1-Hydroxy-4-methylbenzeneChEBI
4-CresolChEBI
4-HydroxytolueneChEBI
4-MethylphenolChEBI
p-KresolChEBI
p-MethylphenolChEBI
p-Tolyl alcoholChEBI
ParacresolChEBI
1-Methyl-4-hydroxybenzeneHMDB
4-(Pentafluorosulfanyl)phenolHMDB
4-Methyl phenolHMDB
4-Methyl-phenolHMDB
p-CresylateHMDB
p-Cresylic acidHMDB
p-HydroxytolueneHMDB
p-Methyl phenolHMDB
p-MethylhydroxybenzeneHMDB
p-OxytolueneHMDB
p-ToluolHMDB
Paramethyl phenolHMDB
4-Cresol, potassium saltHMDB
m-CresolHMDB
4-Cresol, aluminum saltHMDB
4-Cresol, sodium saltHMDB
Para-cresolHMDB
FEMA 2337db_source
P-CresolChEBI
p-Cresol, 8CIdb_source
P-KresolChEBI
P-MethylphenolChEBI
Para-cresylic acidbiospider
Phenol, 4-methyl-biospider
Taurylic aciddb_source
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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
    Spectrum TypeDescriptionSplash Key
    GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-5900000000-1d2bdfde621a5af9be73View in MoNA
    GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-5900000000-b76093f53701327ab25fView in MoNA
    GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-4900000000-7d25deb1e39c6ef4866fView in MoNA
    GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-7900000000-15d473146e11e4b049b2View in MoNA
    GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014l-4900000000-14fef90a661a09457976View in MoNA
    GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-5900000000-1d2bdfde621a5af9be73View in MoNA
    GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-5900000000-b76093f53701327ab25fView in MoNA
    GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-4900000000-7d25deb1e39c6ef4866fView in MoNA
    GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-7900000000-15d473146e11e4b049b2View in MoNA
    GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014l-4900000000-14fef90a661a09457976View in MoNA
    Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-6900000000-27534de20ade11dd5454View in MoNA
    Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-06fr-9700000000-f41dd95ca553de6bafffView in MoNA
    LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0a4i-5900000000-ab55ada5cae0538f383eView in MoNA
    LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0006-9000000000-385a7a99e0409c7f060dView in MoNA
    LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-02tl-9000000000-205f4e5245868e9debccView in MoNA
    LC-MS/MSLC-MS/MS Spectrum - EI-B (VARIAN MAT-44) , Positivesplash10-0a4i-5900000000-fd438231ac0ed75fdf09View in MoNA
    LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-0a4i-5900000000-b76093f53701327ab25fView in MoNA
    LC-MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-D-3000) , Positivesplash10-0a4i-4900000000-7d25deb1e39c6ef4866fView in MoNA
    LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-0a4i-7900000000-0cdab17a1a95f3e65f45View in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-cf0bed2b3a203309d9aaView in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1900000000-4f20c8bd2dde845b499cView in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fb9-9100000000-393b5f734646352622f9View in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-0c45920f40546c2d8944View in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-417774c01b748db1609dView in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9600000000-5583b6dc3ae583b8dab0View in MoNA
    MSMass Spectrum (Electron Ionization)splash10-0a4i-6900000000-729e6f5bdb0da3ed9dedView 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 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.