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2-Phenylethanol (FDB012152)

Record Information
Version1.0
Creation date2010-04-08 22:10:01 UTC
Update date2019-11-26 03:06:16 UTC
Primary IDFDB012152
Secondary Accession Numbers
  • FDB007516
Chemical Information
FooDB Name2-Phenylethanol
Description2-Phenylethanol, also known as phenethyl alcohol or 2-PEA, 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 in all living species, ranging from bacteria to plants to humans. 2-Phenylethanol is a bitter, floral, and honey tasting compound. 2-Phenylethanol is found, on average, in the highest concentration within a few different foods, such as red wine, black walnuts (Juglans nigra), and white wine and in a lower concentration in peppermints (Mentha X piperita), sweet basils (Ocimum basilicum), and bilberries (Vaccinium myrtillus). 2-Phenylethanol has also been detected, but not quantified in, several different foods, such as rowanberries (Sorbus aucuparia), elderberries (Sambucus), rocket salad (ssp.), napa cabbages (Brassica rapa var. pekinensis), and summer savories (Satureja hortensis). This could make 2-phenylethanol a potential biomarker for the consumption of these foods. 2-Phenylethanol, with regard to humans, has been found to be associated with several diseases such as ulcerative colitis, autism, and pervasive developmental disorder not otherwise specified; 2-phenylethanol 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 2-Phenylethanol.
CAS Number60-12-8
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC8H10O
IUPAC name2-phenylethan-1-ol
InChI IdentifierInChI=1S/C8H10O/c9-7-6-8-4-2-1-3-5-8/h1-5,9H,6-7H2
InChI KeyWRMNZCZEMHIOCP-UHFFFAOYSA-N
Isomeric SMILESOCCC1=CC=CC=C1
Average Molecular Weight122.1644
Monoisotopic Molecular Weight122.073164942
Classification
Description 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:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 78.65%; H 8.25%; O 13.10%DFC
Melting PointMp -25.8°DFC
Boiling PointBp10 99.5°DFC
Experimental Water Solubility22.2 mg/mL at 25 oCVALVANI, SC et al. (1981)
Experimental logP1.36HANSCH,C ET AL. (1995)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
Densityd204 1.02DFC
Refractive Indexn20D 1.5325DFC
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0006-9100000000-2e7748b750dd46a70f692015-03-01View Spectrum
GC-MS2-Phenylethan-1-ol, non-derivatized, GC-MS Spectrumsplash10-0006-9100000000-850cab93c17d62d7ae48Spectrum
GC-MS2-Phenylethan-1-ol, non-derivatized, GC-MS Spectrumsplash10-0006-9100000000-e67375f5607fb09ff117Spectrum
GC-MS2-Phenylethan-1-ol, non-derivatized, GC-MS Spectrumsplash10-0006-9100000000-0ea4f78bf9f95dd3e378Spectrum
GC-MS2-Phenylethan-1-ol, non-derivatized, GC-MS Spectrumsplash10-0006-9100000000-850cab93c17d62d7ae48Spectrum
GC-MS2-Phenylethan-1-ol, non-derivatized, GC-MS Spectrumsplash10-0006-9100000000-e67375f5607fb09ff117Spectrum
GC-MS2-Phenylethan-1-ol, non-derivatized, GC-MS Spectrumsplash10-0006-9100000000-0ea4f78bf9f95dd3e378Spectrum
Predicted GC-MS2-Phenylethan-1-ol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9200000000-12b145fa925fdbec3da0Spectrum
Predicted GC-MS2-Phenylethan-1-ol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0096-9300000000-143aa2e8abc3ff64d203Spectrum
Predicted GC-MS2-Phenylethan-1-ol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - QTOF 4V, positivesplash10-0a4i-4900000000-01a904ef24c032004b012020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 5V, positivesplash10-0a4i-3900000000-ddf7f3974789f0591a552020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 7V, positivesplash10-0a4i-2900000000-f5f16d832b17b6c421112020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 10V, positivesplash10-0a6r-4900000000-798c6ceb60cef825b5072020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 15V, positivesplash10-056r-9600000000-ab7ba9e5577110cb66062020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 17V, positivesplash10-004i-9400000000-f7bfe71e4407e811baac2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 20V, positivesplash10-004i-9200000000-fdd7461658bdfde8e1662020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 23V, positivesplash10-004i-9100000000-3ee09fc79fd925fea86a2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 25V, positivesplash10-004i-9000000000-8ca4cd35ef32af2c5ee62020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 27V, positivesplash10-004i-9000000000-bc43025005b4fc0228ea2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 30V, positivesplash10-0fb9-9000000000-ebfd370a836a01c2e6442020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 33V, positivesplash10-0ufr-9000000000-8eb5ed3477e91745eb8a2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 35V, positivesplash10-0ufr-9000000000-08b0a4ab5c93b536ece32020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 40V, positivesplash10-0udi-9000000000-0016533929cda6a361672020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 45V, positivesplash10-0udi-9000000000-a64c19beae57204777f72020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ab9-0900000000-1568ff280886079d95912015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1900000000-e752bbf1c2351ee5aab52015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9600000000-a4927b67121bc2c9a1ed2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-3900000000-796d56c2e36ce04910a52015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006x-8900000000-3a23c6e7ffa45e8861322015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f96-9300000000-5414e7814d2a111717342015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00dl-7900000000-180ad2b2d5ea5abc75fc2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9300000000-dc57d0e64c13958600db2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004l-9000000000-4a2b1f87db1ff5c4e2a02021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4l-7900000000-c5bfd86d969527f320b12021-09-23View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 90 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
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
ChemSpider ID5830
ChEMBL IDCHEMBL448500
KEGG Compound IDC05853
Pubchem Compound ID6054
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDDB02192
HMDB IDHMDB33944
CRC / DFC (Dictionary of Food Compounds) IDHDT74-H:HDT74-H
EAFUS ID2957
Dr. Duke IDBETA-PHENYLETHYLALCOHOL|2-PHENYLETHANOL|2-PHENYLETHYL-ALCOHOL|PHENYL-ETHYL-ALCOHOL|PHENETHYL-ALCOHOL|2-PHENETHANOL|BETA-PHENYLETHANOL
BIGG IDNot Available
KNApSAcK IDC00002663
HET IDPEL
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID60-12-8
GoodScent IDrw1010051
SuperScent IDNot Available
Wikipedia ID2-Phenylethanol
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
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti septic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
flavor48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
motor depressantDUKE
perfumery48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
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
sedative35717 A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
honey
  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
spice
  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
rose
  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
  2. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
lilac
  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
floral
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
rose dried
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
rose flower
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
rose water
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
bitter
  1. Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
Files
MSDSNot Available
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.