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Identification
YMDB IDYMDB01426
Namebenzyl alcohol
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionBenzyl alcohol, also known as alpha-toluenol or benzenemethanol, belongs to the class of organic compounds known as benzyl alcohols. These are organic compounds containing the phenylmethanol substructure. Benzyl alcohol is an extremely weak basic (essentially neutral) compound (based on its pKa). Benzyl alcohol exists in all living species, ranging from bacteria to humans.
Structure
Thumb
Synonyms
  • .alpha.-hydroxytoluene
  • .alpha.-toluenol
  • (hydroxymethyl)benzene
  • a-Hydroxytoluene
  • a-Toluenol
  • alcoholum benzylicum
  • Alcool benzylique
  • alpha-hydroxytoluene
  • Alpha-toluenol
  • Aromatic primary alcohol
  • Bentalol
  • Benzal alcohol
  • Benzenecarbinol
  • Benzenemethanol
  • benzenmethanol
  • Benzoyl alcohol
  • Benzyl alcohol
  • Benzyl alkohol
  • Benzyl-alcohol
  • BenzylAlcohol
  • Benzylalkohol
  • Benzylic alcohol
  • Benzylicum
  • Enzylalcohol
  • hydroxymethylbenzene
  • Hydroxytoluene
  • MBN
  • Methanol benzene
  • Methanol, phenyl-
  • Phenolcarbinol
  • Phenylcarbinol
  • Phenylcarbinolum
  • phenylmethanol
  • Phenylmethyl alcohol
  • Aromatic alcohol
  • Ulesfia
  • Α-hydroxytoluene
  • Α-toluenol
  • Caswell no. 081F
  • Euxyl K 100
  • Itch-X
  • Sunmorl BK 20
  • TB 13g
  • Alcohol, benzyl
CAS number100-51-6
WeightAverage: 108.1378
Monoisotopic: 108.057514878
InChI KeyWVDDGKGOMKODPV-UHFFFAOYSA-N
InChIInChI=1S/C7H8O/c8-6-7-4-2-1-3-5-7/h1-5,8H,6H2
IUPAC Namephenylmethanol
Traditional IUPAC Namebenzyl alcohol
Chemical FormulaC7H8O
SMILESOCC1=CC=CC=C1
Chemical Taxonomy
Description belongs to the class of organic compounds known as benzyl alcohols. These are organic compounds containing the phenylmethanol substructure.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzyl alcohols
Direct ParentBenzyl alcohols
Alternative Parents
Substituents
  • Benzyl alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateLiquid
Charge0
Melting point-15.2 °C
Experimental Properties
PropertyValueReference
Water Solubility42.9 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
LogP1.10 [HANSCH,C ET AL. (1995)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility26.8 g/LALOGPS
logP1.07ALOGPS
logP1.21ChemAxon
logS-0.61ALOGPS
pKa (Strongest Acidic)15.02ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity32.87 m³·mol⁻¹ChemAxon
Polarizability11.89 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • extracellular
Organoleptic Properties
Flavour/OdourSource
BalsamicFDB008745
BerryFDB008745
CherryFDB008745
FloralFDB008745
FlowerFDB008745
GrapefruitFDB008745
PhenolicFDB008745
RoseFDB008745
SweetFDB008745
WalnutFDB008745
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-00ko-6900000000-a9d668ecd37a1579a6feJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-056r-9400000000-77cec715500da9c57a84JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-056r-9400000000-8dc38068387df3fa06aaJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-056r-9300000000-fb124b56257906cce9f1JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-056r-9400000000-7a77e67486ae3b2dd855JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-056r-9400000000-dd0878988e7c2d9a5431JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00ko-6900000000-a9d668ecd37a1579a6feJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0006-8900000000-c256b0b7a0755f08ac64JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-054o-9200000000-a9f7c0f39c81d478c0d4JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dl-9300000000-e1cfa5e819f61adf9df2JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-0a4i-9500000000-2a82c3dd7c6871f61c34JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-0006-9000000000-ad1762d5292c30b29bbdJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-0006-9000000000-3c8d4c630cf42e3bfd3fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-056r-9400000000-c4dcb2148958f946cd01JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-056r-9400000000-e17e577dbe4546313a91JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-01-SG-2) , Positivesplash10-056r-9300000000-fb124b56257906cce9f1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-056r-9400000000-47b3605316c57e02b84fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-056r-9400000000-dd0878988e7c2d9a5431JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0a4i-3900000000-4d1bf15f6cf8f65bf0a6JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-3a71c23796a048eb999cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1900000000-40737e7bdf548d714249JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uxr-9100000000-23e82914cfa9372ecafcJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-1900000000-17f95f5a398b5850abb2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a6r-7900000000-733d283e0916e755a736JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-d0c6e5fc39516ee594b4JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-056r-9400000000-a8f1fd78fa3f8781f296JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • 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
Synthesis Reference:Xu, Hua-Long; Huang, Jing-Jing; Yang, Xin-Yan; Du, Jun-Ming; Shen, Jiang; Shen, Wei. Consecutive hydrogenation of methyl benzoate to non-chloride benzyl alcohol over K-MnO/g-Al2O3 and Cu/SiO2 catalysts. Huaxue Xuebao (2006), 64(16), 1615-1621.
External Links:
ResourceLink
CHEBI ID17987
HMDB IDHMDB03119
Pubchem Compound ID244
Kegg IDC00556
ChemSpider ID13860335
FOODB IDFDB008745
Wikipediabenzyl_alcohol
BioCyc ID34-DIMETHYLBENZYL-ALCOHOL