Record Information
Version1.0
Creation date2010-04-08 22:04:45 UTC
Update date2018-05-29 00:31:08 UTC
Primary IDFDB000893
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePhenol
DescriptionIt is used as a flavouring agent in a few foods, at maximum levels below 10 ppm Phenol, also known as carbolic acid, is an organic compound with the chemical formula C6H5OH. It is a white crystalline solid. The molecule consists of a phenyl (-C6H5), bonded to a hydroxyl (-OH) group. It is produced on a large scale (about 7 billion kg/year) as a precursor to many materials and useful compounds. Phenol is found in many foods, some of which are sweet marjoram, highbush blueberry, orange bell pepper, and tamarind.
CAS Number108-95-2
Structure
Thumb
Synonyms
SynonymSource
Acide carboliqueChEBI
Acide pheniqueChEBI
BenzenolChEBI
Carbolic acidChEBI
CarbolsaeureChEBI
HydroxybenzeneChEBI
KarbolsaeureChEBI
OxybenzeneChEBI
Phenic acidChEBI
Phenylic acidChEBI
Phenylic alcoholChEBI
PHOHChEBI
Liquefied phenolKegg
Phenol for disinfectionKegg
Phenol, liquefiedKegg
PaoscleKegg
CarbolateGenerator
PhenateGenerator
PhenylateGenerator
AnbesolHMDB
BenzophenolHMDB
Campho-phenique cold sore gelHMDB
Campho-phenique gelHMDB
Campho-phenique liquidHMDB
Carbolic acid liquidHMDB
Carbolic oilHMDB
Carbolicum acidumHMDB
CarbolsaureHMDB
Cepastat lozengesHMDB
Cuticura pain relieving ointmentHMDB
FenolHMDB
FenoloHMDB
FenosmolinHMDB
FenosmolineHMDB
Hydroxy-benzeneHMDB
IPHHMDB
IZALHMDB
Liquid phenolHMDB
Liquified phenolHMDB
Monohydroxy benzeneHMDB
MonohydroxybenzeneHMDB
MonophenolHMDB
PhenicHMDB
Phenic alcoholHMDB
Phenol alcoholHMDB
Phenol homopolymerHMDB
Phenol liquidHMDB
Phenol moltenHMDB
Phenol polymer-boundHMDB
Phenol solutionHMDB
Phenol syntheticHMDB
Phenolated waterHMDB
Phenolated water for disinfectionHMDB
PhenoleHMDB
PhenosmolinHMDB
Synthetic phenolHMDB
Tea polyphenolHMDB
Phenol, sodium saltHMDB
Phenolate sodiumHMDB
CarbolHMDB
Phenolate, sodiumHMDB
Sodium phenolateHMDB
FEMA 3223db_source
Phenyl alcoholmanual
Phenyl hydratemanual
Phenyl hydroxidemanual
Predicted Properties
PropertyValueSource
Water Solubility46.6 g/LALOGPS
logP1.39ALOGPS
logP1.67ChemAxon
logS-0.31ALOGPS
pKa (Strongest Acidic)10.02ChemAxon
pKa (Strongest Basic)-5.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity28.04 m³·mol⁻¹ChemAxon
Polarizability9.81 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC6H6O
IUPAC namephenol
InChI IdentifierInChI=1S/C6H6O/c7-6-4-2-1-3-5-6/h1-5,7H
InChI KeyISWSIDIOOBJBQZ-UHFFFAOYSA-N
Isomeric SMILESOC1=CC=CC=C1
Average Molecular Weight94.1112
Monoisotopic Molecular Weight94.041864814
Classification
Description belongs to the class of organic compounds known as 1-hydroxy-4-unsubstituted benzenoids. These are phenols that are unsubstituted at the 4-position.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub Class1-hydroxy-4-unsubstituted benzenoids
Direct Parent1-hydroxy-4-unsubstituted benzenoids
Alternative Parents
Substituents
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 76.57%; H 6.43%; O 17.00%DFC
Melting PointFp 41°DFC
Boiling PointBp25 90.2°DFC
Experimental Water Solubility82.8 mg/mL at 25 oCSOUTHWORTH,GR & KELLER,JL (1986)
Experimental logP1.46HANSCH,C ET AL. (1995)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0udi-3900000000-97dfa3be718a9ee7ace4View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00kf-9000000000-6fb456992902a13931f9View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-78c83ab6ff1d3dfdbec6View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-89b0c430b8924ee2afdeView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-fc01d0ad6740cfd70e13View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-006w-9000000000-c8b41f2899ca8cc9d4bcView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-db80d8b605e20595c679View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0udi-3900000000-97dfa3be718a9ee7ace4View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-c35c89484e2499c62a49View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0g4i-9300000000-afd565a878ea36c74defView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0006-9000000000-e67da0571423f0e6b4b8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0006-9000000000-e0f57b1e970d0d46597eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0006-9000000000-e67da0571423f0e6b4b8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-00kf-9000000000-7bfe3b897e928a8f3a2cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-01-SG-2) , Positivesplash10-0006-9000000000-78c83ab6ff1d3dfdbec6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6L) , Positivesplash10-0006-9000000000-89b0c430b8924ee2afdeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-D-3000) , Positivesplash10-0006-9000000000-fc01d0ad6740cfd70e13View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-0006-9000000000-ca4fa5905cccbfeab33aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9000000000-2c7201e803e029dd1aefView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9000000000-3fb3990dfbfbde2b8d57View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gba-9000000000-d3da8db6579f32d02c6cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-9000000000-a74494cda18ab9fb8055View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-a74494cda18ab9fb8055View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-03a61ff7da92cb08edf8View in MoNA
MSMass Spectrum (Electron Ionization)splash10-00kf-9000000000-40b376f4e58c23369a01View in MoNA
1D NMR1H 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 ID971
ChEMBL IDCHEMBL14060
KEGG Compound IDC15584
Pubchem Compound ID996
Pubchem Substance IDNot Available
ChEBI ID15882
Phenol-Explorer ID657
DrugBank IDDB03255
HMDB IDHMDB00228
CRC / DFC (Dictionary of Food Compounds) IDBLS38-K:BLS38-K
EAFUS ID2977
Dr. Duke IDPHENOL
BIGG IDNot Available
KNApSAcK IDC00002664
HET IDIPH
Flavornet ID108-95-2
GoodScent IDrw1009361
SuperScent IDNot Available
Wikipedia IDPhenol
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
analgesic35480 An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.DUKE
anestheticDUKE
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti hemorrhoidal52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti hydrocoeleDUKE
anti incontinence52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti monosodium-glutamateDUKE
anti onychogryphoticDUKE
anti otitic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
anti prostatiticDUKE
anti pyruveticDUKE
anti septic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti sinusiticDUKE
anti spasticDUKE
anti viral22587 A substance that destroys or inhibits replication of viruses.DUKE
anti wrinkleDUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
carcinogenic50903 A role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities.DUKE
central nervous system depressant35470 A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.DUKE
emeticDUKE
fungicide24127 A substance used to destroy fungal pests.DUKE
hemolyticDUKE
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
vasodilator35620 A drug used to cause dilation of the blood vessels.DUKE
Enzymes
NameGene NameUniProt ID
Serum paraoxonase/lactonase 3PON3Q15166
Serum paraoxonase/arylesterase 1PON1P27169
Serum paraoxonase/arylesterase 2PON2Q15165
6-phosphogluconolactonasePGLSO95336
Glucose-6-phosphate 1-dehydrogenaseG6PDP11413
Sulfotransferase 1A1SULT1A1P50225
Sulfotransferase 1A2SULT1A2P50226
Sulfotransferase 1A3/1A4SULT1A3P50224
6-phosphogluconate dehydrogenase, decarboxylatingPGDP52209
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
phenolic
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
plastic
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
rubber
  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).
— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.