Np mrd loader

You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on NP-MRD.
Record Information
Version1.0
Created at2012-09-11 18:43:05 UTC
Updated at2021-08-19 23:58:12 UTC
NP-MRD IDNP0000545
Secondary Accession NumbersNone
Natural Product Identification
Common Name2-Phenylethanol
Description2-Phenylethanol, also known as benzeneethanol or benzyl carbinol, 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 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 wines, black walnuts, and white wines and in a lower concentration in grape wines, sweet basils, and peppermints. 2-Phenylethanol has also been detected, but not quantified, in several different foods, such as asparagus, allspices, fruits, horned melons, and lemons. 2-Phenylethanol, with regard to humans, has been found to be associated with several diseases such as ulcerative colitis, pervasive developmental disorder not otherwise specified, and autism. 2-Phenylethanol has also been linked to the inborn metabolic disorder celiac disease. A primary alcohol that is ethanol substituted by a phenyl group at position 2.
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, phenylethylHMDB
Alcohol, phenethylHMDB
beta PhenylethanolHMDB
2 PhenylethanolHMDB
Carbinol, benzylHMDB
Chemical FormulaC8H10O
Average Mass122.1644 Da
Monoisotopic Mass122.07316 Da
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
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, D2O, experimental)Wishart Lab2021-06-20View Spectrum
Species
Species of Origin
Species NameSourceReference
Brassica hirtaKNApSAcK Database
Citrus aurantifoliaKNApSAcK Database
Citrus aurantiumKNApSAcK Database
Citrus hystrixKNApSAcK Database
Citrus limonKNApSAcK Database
Citrus paradisiKNApSAcK Database
Citrus reticulataKNApSAcK Database
Citrus spp.KNApSAcK Database
Coffea arabicaKNApSAcK Database
Coffea canephoraKNApSAcK Database
Conyza newiiKNApSAcK Database
Heracleum canescensKNApSAcK Database
Hesperis matronalisKNApSAcK Database
Ligusticum elatumKNApSAcK Database
Litsea cubebaKNApSAcK Database
Lonicera japonicaKNApSAcK Database
Medicago sativaKNApSAcK Database
Murraya paniculataKNApSAcK Database
Nicotiana bonariensisKNApSAcK Database
Nicotiana langsdorffiiKNApSAcK Database
Petroselinum crispumKNApSAcK Database
Pinus spp.KNApSAcK Database
Piper longumKNApSAcK Database
Populus tremuloidesKNApSAcK Database
Rhodiola rosea L.KNApSAcK Database
Rosa rugosaKNApSAcK Database
Rosmarinus officinalisKNApSAcK Database
Silene latifoliaKNApSAcK Database
Tagetes minutaKNApSAcK Database
Viscum articulactumKNApSAcK Database
Zanthoxylum hamiltonianumKNApSAcK Database
Zanthoxylum hamiltoniumKNApSAcK Database
Species Where Detected
Species NameSourceReference
Aphomia sociellaKNApSAcK Database
Homo sapiens (Skin microbiota)KNApSAcK Database
Chemical Taxonomy
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 ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-25.8 °CNot Available
Boiling Point219.00 to 221.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
External Links
HMDB IDHMDB0033944
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
Good Scents IDrw1010051
References
General References
  1. Gao F, Daugulis AJ: Bioproduction of the aroma compound 2-phenylethanol in a solid-liquid two-phase partitioning bioreactor system by Kluyveromyces marxianus. Biotechnol Bioeng. 2009 Oct 1;104(2):332-9. doi: 10.1002/bit.22387. [PubMed:19517523 ]
  2. Farag MA, Al-Mahdy DA: Comparative study of the chemical composition and biological activities of Magnolia grandiflora and Magnolia virginiana flower essential oils. Nat Prod Res. 2013;27(12):1091-7. doi: 10.1080/14786419.2012.696256. Epub 2012 Jun 12. [PubMed:22690913 ]
  3. Politano VT, Diener RM, Christian MS, Hoberman AM, Palmer A, Ritacco G, Adams TB, Api AM: Oral and dermal developmental toxicity studies of phenylethyl alcohol in rats. Int J Toxicol. 2013 Jan-Feb;32(1):32-8. doi: 10.1177/1091581812461811. [PubMed:23385159 ]
  4. Kim B, Cho BR, Hahn JS: Metabolic engineering of Saccharomyces cerevisiae for the production of 2-phenylethanol via Ehrlich pathway. Biotechnol Bioeng. 2014 Jan;111(1):115-24. doi: 10.1002/bit.24993. Epub 2013 Jul 22. [PubMed:23836015 ]
  5. Xiao L, Lee J, Zhang G, Ebeler SE, Wickramasinghe N, Seiber J, Mitchell AE: HS-SPME GC/MS characterization of volatiles in raw and dry-roasted almonds (Prunus dulcis). Food Chem. 2014 May 15;151:31-9. doi: 10.1016/j.foodchem.2013.11.052. Epub 2013 Nov 18. [PubMed:24423498 ]
  6. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .