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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:53:01 UTC
Update Date2021-10-13 06:28:40 UTC
HMDB IDHMDB0032971
Secondary Accession Numbers
  • HMDB32971
Metabolite Identification
Common Name2,3-Dimethylpyrazine
Description2,3-Dimethylpyrazine, also known as fema 3271, belongs to the class of organic compounds known as pyrazines. Pyrazines are compounds containing a pyrazine ring, which is a six-member aromatic heterocycle, that consists of two nitrogen atoms (at positions 1 and 4) and four carbon atoms. Some alkylpyrazines are naturally occurring highly aromatic substances which often have a very low odor threshold and contribute to the taste and aroma of various foods including coffee and wines. 2,3-Dimethylpyrazine is an almond, butter, and caramel tasting compound. 2,3-Dimethylpyrazine has been detected, but not quantified, in several different foods, such as asparagus, fruits, red bell peppers, orange bell peppers, and green bell peppers. This could make 2,3-dimethylpyrazine a potential biomarker for the consumption of these foods. It occurs naturally in asparagus, black or green tea, crispbread, malt, raw shrimp, soya, squid, Swiss cheeses, and wheat bread. It occurs naturally in baked potato, black or green tea, crispbread, French fries, malt, peated malt, raw asparagus, roasted barley, roasted filberts or pecans, squid, wheat bread, wild rice (Zizania aquatica), and wort. 2,3-Dimethylpyrazine 2,3-Dimethylpyrazine is a component of the aroma of roasted sesame seeds. Alkylpyrazines are also formed during the cooking of some foods via Maillard reactions. Alkylpyrazines are chemical compounds based on pyrazine with different substitution patterns.
Structure
Data?1563862333
Synonyms
ValueSource
2,3-DMP PyrazineMeSH
23-Dimethyl-pyrazineChEMBL, HMDB
2,3-Dimethyl-1,4-diazineHMDB
2,3-Dimethyl-pyrazineHMDB
FEMA 3271HMDB
Chemical FormulaC6H8N2
Average Molecular Weight108.1411
Monoisotopic Molecular Weight108.068748266
IUPAC Name2,3-dimethylpyrazine
Traditional Namepyrazine, 2,3-dimethyl-
CAS Registry Number5910-89-4
SMILES
CC1=C(C)N=CC=N1
InChI Identifier
InChI=1S/C6H8N2/c1-5-6(2)8-4-3-7-5/h3-4H,1-2H3
InChI KeyOXQOBQJCDNLAPO-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyrazines. Pyrazines are compounds containing a pyrazine ring, which is a six-member aromatic heterocycle, that consists of two nitrogen atoms (at positions 1 and 4) and four carbon atoms.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazines
Sub ClassPyrazines
Direct ParentPyrazines
Alternative Parents
Substituents
  • Pyrazine
  • Heteroaromatic compound
  • Azacycle
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point155.00 to 157.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility38160 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP0.54Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility180 g/LALOGPS
logP10(0.63) g/LALOGPS
logP10(-0.2) g/LChemAxon
logS10(0.22) g/LALOGPS
pKa (Strongest Basic)1.62ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area25.78 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity30.93 m³·mol⁻¹ChemAxon
Polarizability11.75 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+119.83331661259
DarkChem[M-H]-116.65831661259
DeepCCS[M+H]+125.18830932474
DeepCCS[M-H]-122.22930932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2,3-DimethylpyrazineCC1=C(C)N=CC=N11342.0Standard polar33892256
2,3-DimethylpyrazineCC1=C(C)N=CC=N1884.7Standard non polar33892256
2,3-DimethylpyrazineCC1=C(C)N=CC=N1914.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 2,3-Dimethylpyrazine EI-B (Non-derivatized)splash10-066u-9300000000-a8e384b21f05e83669012017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2,3-Dimethylpyrazine EI-B (Non-derivatized)splash10-066u-9300000000-a8e384b21f05e83669012018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2,3-Dimethylpyrazine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9800000000-84b80cbd4522b6d411202017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2,3-Dimethylpyrazine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-066u-9200000000-81c62da205b82b71c5f42015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Dimethylpyrazine 10V, Positive-QTOFsplash10-0a4i-0900000000-be85de85cd4c9c268d1f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Dimethylpyrazine 20V, Positive-QTOFsplash10-0a4i-1900000000-e32b9221fcb3b6f14e7f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Dimethylpyrazine 40V, Positive-QTOFsplash10-0ldl-9000000000-c45c1029e88c6f7f1abe2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Dimethylpyrazine 10V, Negative-QTOFsplash10-0a4i-0900000000-8bc06f3195c254237e312016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Dimethylpyrazine 20V, Negative-QTOFsplash10-0a4i-0900000000-c7cbca7309a958b109e02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Dimethylpyrazine 40V, Negative-QTOFsplash10-0pb9-9400000000-bbf99b74f59a4b21d37c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Dimethylpyrazine 10V, Negative-QTOFsplash10-0a4i-0900000000-1d4d8b4513a0185581992021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Dimethylpyrazine 20V, Negative-QTOFsplash10-0a4i-1900000000-5e56bb9f78bc0c56fa722021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Dimethylpyrazine 40V, Negative-QTOFsplash10-0006-9000000000-12edac38431654aaa8392021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Dimethylpyrazine 10V, Positive-QTOFsplash10-0a4i-0900000000-f6048b98ce921f15f8932021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Dimethylpyrazine 20V, Positive-QTOFsplash10-0a4i-9700000000-36854acac26b155e72da2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Dimethylpyrazine 40V, Positive-QTOFsplash10-0udi-9000000000-5dfe58276533b985a7b62021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB010958
KNApSAcK IDC00052588
Chemspider ID20843
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAlkylpyrazine
METLIN IDNot Available
PubChem Compound22201
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1008121
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .