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2-phenylethanol (YMDB01072)

Identification
YMDB IDYMDB01072
Name2-phenylethanol
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionPhenethyl alcohol (2-phenylethanol) is an alcohol with a pleasant floral odor that occurs widely in nature. It is found in a variety of essential oils, including rose, carnation, hyacinth, Aleppo pine, orange blossom, ylang-ylang, geranium, neroli, and champaca. It is therefore a common ingredient in flavors and perfumery, particularly when the smell of rose is desired. It is responsible for honey-like aromas, a major aroma component of Muscat wine. It is used as an additive in cigarettes. It is also used as a preservative in soaps due to its stability in basic conditions. In biology it is of interest due to its antimicrobial properties.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 1-Phenyl-2-ethanol
  • 1-phenyl-2-ethanol (beta-phenylethanol)
  • 2-Hydroxyethylbenzene
  • 2-PEA
  • 2-Phenethanol
  • 2-Phenethyl Alcohol
  • 2-PhenyIethanol
  • 2-PHENYL-ETHANOL
  • 2-Phenylethanol
  • 2-Phenylethyl alcohol
  • Benzeneethanol
  • Benzeneethanol (2-Phenylethanol)
  • benzenethanol
  • Benzyl Carbinol
  • Benzylmethanol
  • beta-Fenethylalkohol
  • beta-Fenylethanol
  • beta-Hydroxyethylbenzene
  • beta-P.E.A.
  • beta-PEA
  • beta-Phenethanol
  • beta-Phenethyl alcohol
  • beta-Phenylethanol
  • beta-Phenylethyl alcohol
  • Ethanol, 2-phenyl-
  • Hydroxyethylbenzene
  • Mellol
  • Methanol, benzyl-
  • Orange oil
  • PEA
  • Phenethanol
  • Phenethyl alcohol
  • Phenylethanol
  • Phenylethyl alcohol
  • Phenylethyl, b- alcohol
  • Rose oil
  • b-PEA
  • Β-pea
  • b-Phenethyl alcohol
  • Β-phenethyl alcohol
  • b-Phenylethanol
  • Β-phenylethanol
  • b-Phenylethyl alcohol
  • Β-phenylethyl alcohol
  • b-Hydroxyethylbenzene
  • Benzeneethanol, 9ci
  • Benzyl ethyl alcohol
  • Benzyl-methanol
  • Benzylcarbinol
  • beta -Hydroxyethylbenzene
  • FEMA 2858
  • Phenethyl alcohol, 8ci, ban
  • Phenyl ethyl alcohol
  • Phenyl-ethanol
  • Phenylethyl alcohol, usan
  • Alcohol, phenylethyl
  • Alcohol, phenethyl
  • beta Phenylethanol
  • 2 Phenylethanol
  • Carbinol, benzyl
CAS number60-12-8
WeightAverage: 122.1644
Monoisotopic: 122.073164942
InChI KeyWRMNZCZEMHIOCP-UHFFFAOYSA-N
InChIInChI=1S/C8H10O/c9-7-6-8-4-2-1-3-5-8/h1-5,9H,6-7H2
IUPAC Name2-phenylethan-1-ol
Traditional IUPAC Namephenylethanol
Chemical FormulaC8H10O
SMILESOCCC1=CC=CC=C1
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 Parents
Substituents
  • Monocyclic benzene moiety
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateLiquid
Charge0
Melting point-27 °C
Experimental Properties
PropertyValueReference
Water Solubility22.2 mg/mL at 25 oC [VALVANI, SC et al. (1981)]PhysProp
LogP1.36 [HANSCH,C ET AL. (1995)]PhysProp
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
Biological Properties
Cellular Locations
  • extracellular
  • mitochondrion
  • cytoplasm
Organoleptic Properties
Flavour/OdourSource
CoolFDB012152
FreshFDB012152
GreenFDB012152
HyacinthFDB012152
LeafyFDB012152
MetallicFDB012152
SpringFDB012152
SMPDB Pathways
Phenylalanine metabolismPW002437 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Phenylalanine metabolismec00360 Map00360
SMPDB Reactions
Phenylacetaldehyde + hydron + NADH → 2-phenylethanol + NAD
KEGG Reactions
Acetyl-CoA + 2-phenylethanol → phenethyl acetate + Coenzyme A
NADH + Phenylacetaldehyde + hydron → NAD + 2-phenylethanol
Phenylacetaldehyde + NADPH + hydron → NADP + 2-phenylethanol
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9100000000-850cab93c17d62d7ae48JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9100000000-e67375f5607fb09ff117JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9100000000-0ea4f78bf9f95dd3e378JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9100000000-850cab93c17d62d7ae48JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9100000000-e67375f5607fb09ff117JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9100000000-0ea4f78bf9f95dd3e378JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9200000000-12b145fa925fdbec3da0JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0096-9300000000-143aa2e8abc3ff64d203JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - QTOF 4V, positivesplash10-0a4i-4900000000-01a904ef24c032004b01JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 5V, positivesplash10-0a4i-3900000000-ddf7f3974789f0591a55JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 7V, positivesplash10-0a4i-2900000000-f5f16d832b17b6c42111JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 10V, positivesplash10-0a6r-4900000000-798c6ceb60cef825b507JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 15V, positivesplash10-056r-9600000000-ab7ba9e5577110cb6606JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 17V, positivesplash10-004i-9400000000-f7bfe71e4407e811baacJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 20V, positivesplash10-004i-9200000000-fdd7461658bdfde8e166JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 23V, positivesplash10-004i-9100000000-3ee09fc79fd925fea86aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 25V, positivesplash10-004i-9000000000-8ca4cd35ef32af2c5ee6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 27V, positivesplash10-004i-9000000000-bc43025005b4fc0228eaJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 30V, positivesplash10-0fb9-9000000000-ebfd370a836a01c2e644JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 33V, positivesplash10-0ufr-9000000000-8eb5ed3477e91745eb8aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 35V, positivesplash10-0ufr-9000000000-08b0a4ab5c93b536ece3JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 40V, positivesplash10-0udi-9000000000-0016533929cda6a36167JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 45V, positivesplash10-0udi-9000000000-a64c19beae57204777f7JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ab9-0900000000-1568ff280886079d9591JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1900000000-e752bbf1c2351ee5aab5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9600000000-a4927b67121bc2c9a1edJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-3900000000-796d56c2e36ce04910a5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006x-8900000000-3a23c6e7ffa45e886132JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f96-9300000000-5414e7814d2a11171734JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00dl-7900000000-180ad2b2d5ea5abc75fcJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9300000000-dc57d0e64c13958600dbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004l-9000000000-4a2b1f87db1ff5c4e2a0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4l-7900000000-c5bfd86d969527f320b1JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-0006-9100000000-2e7748b750dd46a70f69JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • Verstrepen, K. J., Van Laere, S. D., Vanderhaegen, B. M., Derdelinckx, G., Dufour, J. P., Pretorius, I. S., Winderickx, J., Thevelein, J. M., Delvaux, F. R. (2003). "Expression levels of the yeast alcohol acetyltransferase genes ATF1, Lg-ATF1, and ATF2 control the formation of a broad range of volatile esters." Appl Environ Microbiol 69:5228-5237.12957907
  • Antonelli, A., Castellari, L., Zambonelli, C., Carnacini, A. (1999). "Yeast influence on volatile composition of wines." J Agric Food Chem 47:1139-1144.10552428
  • Tsakiris, A., Koutinas, A. A., Psarianos, C., Kourkoutas, Y., Bekatorou, A. (2010). "A new process for wine production by penetration of yeast in uncrushed frozen grapes." Appl Biochem Biotechnol 162:1109-1121.20151225
  • Patel, S., Shibamoto, T. (2002). "Effect of different strains of Saccharomyces cerevisiae on production of volatiles in Napa Gamay wine and Petite Sirah wine." J Agric Food Chem 50:5649-5653.12236692
  • Leskovac, V., Trivic, S., Pericin, D. (2002). "The three zinc-containing alcohol dehydrogenases from baker's yeast, Saccharomyces cerevisiae." FEMS Yeast Res 2:481-494.12702265
  • Chi, A., Huttenhower, C., Geer, L. Y., Coon, J. J., Syka, J. E., Bai, D. L., Shabanowitz, J., Burke, D. J., Troyanskaya, O. G., Hunt, D. F. (2007). "Analysis of phosphorylation sites on proteins from Saccharomyces cerevisiae by electron transfer dissociation (ETD) mass spectrometry." Proc Natl Acad Sci U S A 104:2193-2198.17287358
  • Larroy, C., Pares, X., Biosca, J. A. (2002). "Characterization of a Saccharomyces cerevisiae NADP(H)-dependent alcohol dehydrogenase (ADHVII), a member of the cinnamyl alcohol dehydrogenase family." Eur J Biochem 269:5738-5745.12423374
  • Dickinson, J. R., Salgado, L. E., Hewlins, M. J. (2003). "The catabolism of amino acids to long chain and complex alcohols in Saccharomyces cerevisiae." J Biol Chem 278:8028-8034.12499363
  • Larroy, C., Fernandez, M. R., Gonzalez, E., Pares, X., Biosca, J. A. (2002). "Characterization of the Saccharomyces cerevisiae YMR318C (ADH6) gene product as a broad specificity NADPH-dependent alcohol dehydrogenase: relevance in aldehyde reduction." Biochem J 361:163-172.11742541
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID49000
HMDB IDHMDB0033944
Pubchem Compound ID6054
Kegg IDC05853
ChemSpider ID5830
FOODB IDFDB012152
WikipediaPhenethyl_alcohol
BioCyc IDNot Available

Enzymes

Protein Details
1. NADP-dependent alcohol dehydrogenase 7
General function:
Involved in zinc ion binding
Specific function:
NADP-dependent alcohol dehydrogenase with a broad substrate specificity
Gene Name:
ADH7
Uniprot ID:
P25377
Molecular weight:
39348.19922
Reactions
An alcohol + NADP(+) → an aldehyde + NADPH.
Protein Details
2. NADP-dependent alcohol dehydrogenase 6
General function:
Involved in zinc ion binding
Specific function:
NADP-dependent alcohol dehydrogenase with a broad substrate specificity
Gene Name:
ADH6
Uniprot ID:
Q04894
Molecular weight:
39617.30078
Reactions
An alcohol + NADP(+) → an aldehyde + NADPH.