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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2012-09-11 18:43:05 UTC
Update Date2018-05-20 10:19:53 UTC
HMDB IDHMDB0033944
Secondary Accession Numbers
  • HMDB33944
Metabolite Identification
Common Name2-Phenylethanol
Description2-Phenylethanol, also known as phenethyl alcohol or benzeneethanol, belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene. 2-Phenylethanol exists as a solid, soluble (in water), and an extremely weak acidic (essentially neutral) compound (based on its pKa). 2-Phenylethanol has been primarily detected in feces. Within the cell, 2-phenylethanol is primarily located in the cytoplasm. 2-Phenylethanol exists in all eukaryotes, ranging from yeast to humans. 2-Phenylethanol can be biosynthesized from phenylacetaldehyde; which is catalyzed by the enzyme alcohol dehydrogenase. 2-Phenylethanol is a bitter, floral, and honey tasting compound that can be found in a number of food items such as loganberry, chinese mustard, poppy, and persian lime. This makes 2-phenylethanol a potential biomarker for the consumption of these food products. 2-Phenylethanol has been found to be associated with several diseases known as pervasive developmental disorder not otherwise specified and autism; 2-phenylethanol has also been linked to the inborn metabolic disorders including celiac disease.
Structure
Thumb
Synonyms
ValueSource
2-HydroxyethylbenzeneChEBI
2-PEAChEBI
2-PHENYL-ethanolChEBI
BenzeneethanolChEBI
BenzylmethanolChEBI
beta-PEAChEBI
beta-Phenethyl alcoholChEBI
beta-PhenylethanolChEBI
beta-Phenylethyl alcoholChEBI
Phenethyl alcoholChEBI
Phenylethyl alcoholChEBI
b-PEAGenerator
β-peaGenerator
b-Phenethyl alcoholGenerator
β-phenethyl alcoholGenerator
b-PhenylethanolGenerator
β-phenylethanolGenerator
b-Phenylethyl alcoholGenerator
β-phenylethyl alcoholGenerator
1-Phenyl-2-ethanolHMDB
2-PhenethanolHMDB
2-Phenethyl alcoholHMDB
2-PhenyIethanolHMDB
2-Phenylethyl alcoholHMDB
b-HydroxyethylbenzeneHMDB
Benzeneethanol, 9ciHMDB
BenzenethanolHMDB
Benzyl carbinolHMDB
Benzyl ethyl alcoholHMDB
Benzyl-methanolHMDB
BenzylcarbinolHMDB
beta -HydroxyethylbenzeneHMDB
FEMA 2858HMDB
HydroxyethylbenzeneHMDB
PhenethanolHMDB
Phenethyl alcohol, 8ci, banHMDB
Phenyl ethyl alcoholHMDB
Phenyl-ethanolHMDB
PhenylethanolHMDB
Phenylethyl alcohol, usanHMDB
Alcohol, phenylethylMeSH
Alcohol, phenethylMeSH
beta PhenylethanolMeSH
2 PhenylethanolMeSH
Carbinol, benzylMeSH
Chemical FormulaC8H10O
Average Molecular Weight122.1644
Monoisotopic Molecular Weight122.073164942
IUPAC Name2-phenylethan-1-ol
Traditional Namephenylethanol
CAS Registry Number60-12-8
SMILES
OCCC1=CC=CC=C1
InChI Identifier
InChI=1S/C8H10O/c9-7-6-8-4-2-1-3-5-8/h1-5,9H,6-7H2
InChI KeyWRMNZCZEMHIOCP-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassNot Available
Direct ParentBenzene and substituted derivatives
Alternative Parents
Substituents
  • Monocyclic benzene moiety
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-25.8 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility22.2 mg/mL at 25 °CNot Available
LogP1.36Not Available
Predicted Properties
PropertyValueSource
Water Solubility11.3 g/LALOGPS
logP1.51ALOGPS
logP1.49ChemAxon
logS-1ALOGPS
pKa (Strongest Acidic)15.88ChemAxon
pKa (Strongest Basic)-2.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity37.63 m³·mol⁻¹ChemAxon
Polarizability13.87 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9100000000-850cab93c17d62d7ae48View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9100000000-e67375f5607fb09ff117View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9100000000-0ea4f78bf9f95dd3e378View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9100000000-850cab93c17d62d7ae48View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9100000000-e67375f5607fb09ff117View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9100000000-0ea4f78bf9f95dd3e378View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9200000000-12b145fa925fdbec3da0View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0096-9300000000-143aa2e8abc3ff64d203View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ab9-0900000000-1568ff280886079d9591View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1900000000-e752bbf1c2351ee5aab5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9600000000-a4927b67121bc2c9a1edView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-3900000000-796d56c2e36ce04910a5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006x-8900000000-3a23c6e7ffa45e886132View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f96-9300000000-5414e7814d2a11171734View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0006-9100000000-2e7748b750dd46a70f69View in MoNA
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
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected and Quantified27.286 (0-54.571) nmol/g wet fecesChildren (1 - 13 years old)Both
Normal
details
FecesDetected and Quantified0-113972.101 nmol/g wet fecesChildren (1-13 years old)Not Specified
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected and Quantified0-71406.509 nmol/g wet fecesChildren (1-13 years old)Not Specified
Treated celiac disease
details
FecesDetected and Quantified27.286 (0-109.143) nmol/g wet fecesChildren (1 - 13 years old)Both
Autism
details
FecesDetected and Quantified27.286 (0-54.571) nmol/g wet fecesChildren (1 - 13 years old)Both
Developmental Disorder Not Otherwise Specified
details
FecesDetected but not Quantified Adult (>18 years old)Both
Campylobacter jejuni infection
details
FecesDetected but not Quantified Adult (>18 years old)Both
Clostridium difficile infection
details
FecesDetected but not Quantified Adult (>18 years old)Both
Ulcerative Colitis
details
Associated Disorders and Diseases
Disease References
Autism
  1. De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]
Celiac disease
  1. Di Cagno R, De Angelis M, De Pasquale I, Ndagijimana M, Vernocchi P, Ricciuti P, Gagliardi F, Laghi L, Crecchio C, Guerzoni ME, Gobbetti M, Francavilla R: Duodenal and faecal microbiota of celiac children: molecular, phenotype and metabolome characterization. BMC Microbiol. 2011 Oct 4;11:219. doi: 10.1186/1471-2180-11-219. [PubMed:21970810 ]
Ulcerative colitis
  1. Garner CE, Smith S, de Lacy Costello B, White P, Spencer R, Probert CS, Ratcliffe NM: Volatile organic compounds from feces and their potential for diagnosis of gastrointestinal disease. FASEB J. 2007 Jun;21(8):1675-88. Epub 2007 Feb 21. [PubMed:17314143 ]
Pervasive developmental disorder not otherwise specified
  1. De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]
Associated OMIM IDs
DrugBank IDDB02192
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012152
KNApSAcK IDC00002663
Chemspider ID5830
KEGG Compound IDC05853
BioCyc IDCPD-7035
BiGG IDNot Available
Wikipedia LinkPhenethyl_alcohol
METLIN IDNot Available
PubChem Compound6054
PDB IDPEL
ChEBI ID49000
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .