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Phenol (FDB000893)

Record Information
Version1.0
Creation date2010-04-08 22:04:45 UTC
Update date2024-11-29 22:27:43 UTC
Primary IDFDB000893
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePhenol
DescriptionPhenol, also known as hydroxybenzene or carbolic acid, belongs to the class of organic compounds known as hydroxy benzenoids. Phenol is a toxic, colourless crystalline solid with a sweet tarry odor that resembles a hospital smell. It is commonly used as an antiseptic and disinfectant. It is active against a wide range of microorganisms including some fungi and viruses but is only slowly effective against spores. It has been used to disinfect skin and to relieve itching. Phenol is also used in the preparation of cosmetics including sunscreens, hair dyes, and skin lightening preparations. It is also used in the production of drugs (it is the starting material in the industrial production of aspirin), weedkillers, and synthetic resins. Phenol can be found in areas with high levels of motor traffic, therefore, people living in crowded urban areas are frequently exposed to traffic-derived phenol vapor. The average (mean +/- SD) phenol concentration in urine among normal individuals living in urban areas is 7.4 +/- 2.2 mg/g of creatinine. Exposure of the skin to concentrated phenol solutions causes chemical burns which may be severe. In laboratories where it is used, it is usually recommended that polyethylene glycol solution is kept available for washing off splashes. In some bacteria phenol can be directly synthesized from tyrosine via the enzyme tyrosine phenol-lyase [EC:4.1.99.2]. It can be produced by Escherichia and Pseudomonas. Phenol has been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID: 22626821).
CAS Number108-95-2
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
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
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 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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-00kf-9000000000-40b376f4e58c23369a012014-09-20View Spectrum
GC-MSPhenol, 1 TMS, GC-MS Spectrumsplash10-0udi-3900000000-97dfa3be718a9ee7ace4Spectrum
GC-MSPhenol, non-derivatized, GC-MS Spectrumsplash10-00kf-9000000000-6fb456992902a13931f9Spectrum
GC-MSPhenol, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-78c83ab6ff1d3dfdbec6Spectrum
GC-MSPhenol, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-89b0c430b8924ee2afdeSpectrum
GC-MSPhenol, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-fc01d0ad6740cfd70e13Spectrum
GC-MSPhenol, non-derivatized, GC-MS Spectrumsplash10-006w-9000000000-c8b41f2899ca8cc9d4bcSpectrum
GC-MSPhenol, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-db80d8b605e20595c679Spectrum
GC-MSPhenol, non-derivatized, GC-MS Spectrumsplash10-0udi-3900000000-97dfa3be718a9ee7ace4Spectrum
Predicted GC-MSPhenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9000000000-c35c89484e2499c62a49Spectrum
Predicted GC-MSPhenol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0g4i-9300000000-afd565a878ea36c74defSpectrum
Predicted GC-MSPhenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0006-9000000000-e67da0571423f0e6b4b82012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0006-9000000000-e0f57b1e970d0d46597e2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0006-9000000000-e67da0571423f0e6b4b82012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-00kf-9000000000-7bfe3b897e928a8f3a2c2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-01-SG-2) , Positivesplash10-0006-9000000000-78c83ab6ff1d3dfdbec62012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6L) , Positivesplash10-0006-9000000000-89b0c430b8924ee2afde2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-D-3000) , Positivesplash10-0006-9000000000-fc01d0ad6740cfd70e132012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-0006-9000000000-ca4fa5905cccbfeab33a2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0002-9000000000-e3e33defb000b450bb372021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0002-9200000000-d63db79771e5931b258f2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9000000000-448a4d79ff53d77a8b162021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9000000000-2c7201e803e029dd1aef2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9000000000-3fb3990dfbfbde2b8d572016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gba-9000000000-d3da8db6579f32d02c6c2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-9000000000-a74494cda18ab9fb80552016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-a74494cda18ab9fb80552016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-03a61ff7da92cb08edf82016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9000000000-c65d4a4eaa8adde2ddb42021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-9000000000-def7a8d52afb63a3cd672021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9000000000-f3c795ffc788635ddbf42021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-9000000000-08485aaf085c13d5129a2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-08485aaf085c13d5129a2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-52b0f93832ef13f17bd22021-09-24View 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
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
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
Food Biomarker OntologyNot Available
VMH IDNot Available
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
Pathways
NameSMPDB LinkKEGG Link
Metabolism and Physiological Effects of Phenyl sulfateSMP0123213 Not Available
Metabolism and Physiological Effects of Phenyl glucuronideSMP0123227 Not Available
Metabolism and Physiological Effects of Phenol SMP0123255 Not Available
Metabolism and Physiological Effects of Phenol sulphate SMP0126844 Not 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.