2-Methoxy-3-isobutylpyrazine (YMDB01586)

Identification
YMDB IDYMDB01586
Name2-Methoxy-3-isobutylpyrazine
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
Description2-Methoxy-3-isobutylpyrazine is a 3-alkyl-2-methoxypyrazine, which are important compounds for the aroma of wines. 2-Methoxy-3-isobutylpyrazine has been related with the green and vegetative aromas characteristic of some wines made with Cabernet Sauvignon, Sauvignon blanc, Merlot or Cabernet Franc grapes. It it is typically found at 15-30 ng/L in these wines. The origin of 3-alkyl-2-methoxypyrazines is mostly endogenous as these compounds are part of the chemicals produced in the first stages of grape development. [PMID: 21227432]
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 2-Isobutyl-3-methoxypyrazine
  • 2-methoxy-3-(2-methylpropyl)pyrazine
  • 3-isobutyl-2-methoxypyrazine
  • 3-methoxy-2-isobutylpyrazine
  • Pyrazine, 2-(2-methylpropyl)-3-methoxy
  • Pyrazine, 2-isobutyl-3-methoxy
  • pyrazine, 2-methoxy, 3-isobutyl
  • Pyrazine, 3-methoxy-2-(2-methylpropyl)
  • 1DZK
  • 2-Isobutyl-3-methoxy-pyrazine
  • 2-Isobutyl-3-methoxypyrazine, 8ci
  • 2-Methoxy-3-(2-methyl-propyl) pyrazine
  • 2-Methoxy-3-(2-methylpropyl)-pyrazine
  • 2-Methoxy-3-isobutylpyrazine
  • FEMA 3132
  • Galbazine
  • IBMP
  • PRZ
CAS number24683-00-9
WeightAverage: 166.2203
Monoisotopic: 166.11061308
InChI KeyUXFSPRAGHGMRSQ-UHFFFAOYSA-N
InChIInChI=1S/C9H14N2O/c1-7(2)6-8-9(12-3)11-5-4-10-8/h4-5,7H,6H2,1-3H3
IUPAC Name2-methoxy-3-(2-methylpropyl)pyrazine
Traditional IUPAC Name2-isobutyl-3-methoxypyrazine
Chemical FormulaC9H14N2O
SMILESCOC1=NC=CN=C1CC(C)C
Chemical Taxonomy
Description belongs to the class of organic compounds known as methoxypyrazines. These are pyrazines containing a methoxyl group attached to the pyrazine ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazines
Sub ClassPyrazines
Direct ParentMethoxypyrazines
Alternative Parents
Substituents
  • Methoxypyrazine
  • Alkyl aryl ether
  • Heteroaromatic compound
  • Azacycle
  • Ether
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility20.9 g/LALOGPS
logP2.11ALOGPS
logP1.54ChemAxon
logS-0.9ALOGPS
pKa (Strongest Basic)0.98ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area35.01 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity46.89 m³·mol⁻¹ChemAxon
Polarizability18.38 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic Properties
Flavour/OdourSource
BellFDB008544
EarthFDB008544
GalbanumFDB008544
GreenFDB008544
Green pepperFDB008544
PeaFDB008544
PepperFDB008544
SpiceFDB008544
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-9800000000-b2a76f846c9e6cdec480JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-f195deae40b120d03a2bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0aor-7900000000-ce68c6d37c62fbafe643JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a59-9100000000-fdcbed3bfb97241ae911JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-f72a38590d903075c866JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-2900000000-8a6a0e5c0c27143a34f1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9300000000-02b43dab5d60f685355eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-36e5a9d0812fa5b880dcJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-1900000000-a3ae70c6cad1c5005bd3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-1252189c65cc284d2024JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-d120bc32d136e668f60aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-2900000000-b41ddec9414daee33f17JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014l-9100000000-4674a4a6a16f025751abJSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-00di-9800000000-0379fe3fc6cfe11798f3JSpectraViewer | MoNA
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
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDHMDB0031860
Pubchem Compound ID32594
Kegg IDNot Available
ChemSpider ID30208
FOODB IDFDB008544
Wikipedia IDNot Available
BioCyc IDNot Available