You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Yeast Metabolome Database.

Nerol (YMDB01760)

Identification
YMDB IDYMDB01760
NameNerol
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionGeraniol, also known as (Z)-geraniol or neryl alcohol, belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle. Thus, geraniol is considered to be an isoprenoid lipid molecule. Geraniol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
  • (2E)3,7-dimethyl-2,6-Octadien-1-ol
  • (2Z)-3,7-Dimethyl-2,6-octadien-1-ol
  • (2Z)3,7-dimethyl-2,6-Octadien-1-ol
  • (cis)3,7-dimethyl-2,6-Octadien-1-ol
  • (E)3,7-dimethyl-2,6-Octadien-1-ol
  • (E)3,7-Dimethyl-Octadien-1-ol
  • (Z)-3,7-dimethyl-2,6-octadien-1-ol
  • (z)-geraniol
  • (Z)3,7-dimethyl-2,6-Octadien-1-ol
  • 2-cis-3,7-Dimethyl-2,6-octadien-1-ol
  • 2-trans-3,7-Dimethyl-2,6-octadien-1-ol
  • 2-trans-3,7-dimethyl-2,6-octadiene-1-ol
  • 2, 6-Octadien-1-ol, 3,7-dimethyl-,(Z)-
  • 2,6-Dimethyl-2,6-octadien-8-ol
  • 2,6-dimethyl-trans-2,6-octadien-8-ol
  • 2,6-Octadien-1-ol, 3,7-dimethyl-, (E)-
  • 2,6-Octadien-1-ol, 3,7-dimethyl-, (Z)-
  • 2E-geraniol
  • 3,7-dimethyl-2,6-Octadien-1-ol
  • 3,7-Dimethyl-Octane-1-ol tetrahydro derivative
  • 3,7-Dimethyl-trans-2, 6-octadien-1-ol
  • 3,7-dimethylocta-2,6-dien-1-ol
  • Beta-geraniol
  • cis-3,7-Dimethyl-2,6-octadien-1-ol
  • Cis-geraniol
  • Geraniol (natural)
  • Geraniol alcohol
  • Geranyl alcohol
  • Guaniol
  • Lemonol
  • Nerol
  • Nerol (cis-geraniol)
  • Nerol (natural)
  • Nerolidyl diphosphate
  • Neryl alcohol
  • NPP
  • trans-3,7-dimethyl-2,6-octadien-1-ol
  • Trans-geraniol
  • Vernol
  • (Z)-3,7-Dimethylocta-2,6-dien-1-ol
  • Geraniol, 2-(14)C-labeled, (e)-isomer
  • Geraniol, titanium (4+) salt
  • Geraniol, (Z)-isomer
  • Geraniol, 1-(14)C-labeled, (e)-isomer
  • Geraniol, (e)-isomer
  • Geraniol
  • (Z)-3,7-Dimethyl-2,6-octadienol
  • (Z)-3,7-Dimethyloct-2,6-diene-1-ol
  • (Z)-Nerol
  • 3,7-Dimethyl-cis-2,6-octadien-1-ol
  • cis-1-Hydroxy-3,7-dimethyl-2,6-octadiene
  • beta-Nerol
  • β-Nerol
CAS number106-25-2
WeightAverage: 154.2493
Monoisotopic: 154.135765198
InChI KeyGLZPCOQZEFWAFX-YFHOEESVSA-N
InChIInChI=1S/C10H18O/c1-9(2)5-4-6-10(3)7-8-11/h5,7,11H,4,6,8H2,1-3H3/b10-7-
IUPAC Name(2Z)-3,7-dimethylocta-2,6-dien-1-ol
Traditional IUPAC Namenerol
Chemical FormulaC10H18O
SMILESCC(C)=CCC\C(C)=C/CO
Chemical Taxonomy
Description belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentAcyclic monoterpenoids
Alternative Parents
Substituents
  • Acyclic monoterpenoid
  • Fatty alcohol
  • Fatty acyl
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateLiquid
Charge0
Melting point<-15 °C
Experimental Properties
PropertyValueReference
Water Solubility0.531 mg/mL at 25 oC [MILLER,DJ & HAWTHORNE,SB (2000A)]PhysProp
LogP3.47 [GRIFFIN,S ET AL. (1999)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility1.37 g/LALOGPS
logP2.89ALOGPS
logP2.5ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)16.33ChemAxon
pKa (Strongest Basic)-2.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity51.18 m³·mol⁻¹ChemAxon
Polarizability19.29 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic Properties
Flavour/OdourSource
BitterFDB014945
CitrusFDB014945
MagnoliaFDB014945
NaturalFDB014945
NeroliFDB014945
SweetFDB014945
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 - EI-B (Non-derivatized)splash10-014l-9000000000-8132ea67e057a3dd9c80JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014l-9100000000-a5bdece739d0cb5bf629JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-015c-9200000000-eea073073c86ea4d9a38JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-0625da1bcd5a7d1938a6JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014l-9000000000-41e0055b618413366b81JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014l-9000000000-8132ea67e057a3dd9c80JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014l-9100000000-a5bdece739d0cb5bf629JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-015c-9200000000-eea073073c86ea4d9a38JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-0625da1bcd5a7d1938a6JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014l-9000000000-41e0055b618413366b81JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-Q (Non-derivatized)splash10-014l-9000000000-2ab93357dd27a7c07eb7JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-014u-9300000000-c85bc4c928fbf7d824e8JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-030c-9520000000-69b7fbbb25764f7b612eJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-001r-9600000000-69c0de28e07b8b530c9aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-001i-9100000000-0ee3622152359826448fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-003r-9000000000-d5bb693fadd752735f31JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-014l-9000000000-8132ea67e057a3dd9c80JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-014l-9100000000-a5bdece739d0cb5bf629JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-015c-9200000000-eea073073c86ea4d9a38JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (SHIMADZU QP-1000) , Positivesplash10-0006-9000000000-0625da1bcd5a7d1938a6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-014l-9000000000-7b5a5cfbbe0b42fdd23eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 10V, negativesplash10-0a4i-0900000000-73a127efb4137eb42580JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-1900000000-3d437630e5bec67a7e07JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-8900000000-0e505c85cec6344cab5cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-9100000000-c7400df359a9559bd594JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-113756054eed13d33ee4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fk9-0900000000-dea43b41c5b791cef9d2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0aou-9800000000-c028a2bd655026094251JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • Loscos, N., Hernandez-Orte, P., Cacho, J., Ferreira, V. (2007). "Release and formation of varietal aroma compounds during alcoholic fermentation from nonfloral grape odorless flavor precursors fractions." J Agric Food Chem 55:6674-6684.17616208
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID29452
HMDB IDHMDB05812
Pubchem Compound ID3327
Kegg IDC06111
ChemSpider ID558917
FOODB IDFDB014945
Wikipedia IDNerol
BioCyc IDNot Available