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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:48:53 UTC
Update Date2022-03-07 02:53:18 UTC
HMDB IDHMDB0032276
Secondary Accession Numbers
  • HMDB32276
Metabolite Identification
Common Name2-Ethyl-3,(5 or 6)-dimethylpyrazine
Description2-Ethyl-3,(5 or 6)-dimethylpyrazine, also known as 2E3,6DMP, 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. 2-Ethyl-3,(5 or 6)-dimethylpyrazine is a cocoa, nutty, and potato tasting compound. 2-Ethyl-3,(5 or 6)-dimethylpyrazine has been detected, but not quantified in, several different foods, such as arabica coffees (Coffea arabica), coffee and coffee products, robusta coffees (Coffea canephora), herbal tea, and teas (Camellia sinensis). This could make 2-ethyl-3,(5 or 6)-dimethylpyrazine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 2-Ethyl-3,(5 or 6)-dimethylpyrazine.
Structure
Data?1563862241
Synonyms
ValueSource
2E3,6DMPMeSH
2-Ethyl-3,6-dimethylpyrazineMeSH
2-Ethyl-3,5/6-dimethyl-pyrazineHMDB
Chemical FormulaC8H12N2
Average Molecular Weight136.1943
Monoisotopic Molecular Weight136.100048394
IUPAC Name3-ethyl-2,5-dimethylpyrazine
Traditional Name3-ethyl-2,5-dimethylpyrazine
CAS Registry Number27043-05-6
SMILES
CCC1=NC(C)=CN=C1C
InChI Identifier
InChI=1S/C8H12N2/c1-4-8-7(3)9-5-6(2)10-8/h5H,4H2,1-3H3
InChI KeyWHMWOHBXYIZFPF-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

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility1473 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility21.4 g/LALOGPS
logP1.59ALOGPS
logP0.63ChemAxon
logS-0.8ALOGPS
pKa (Strongest Basic)1.93ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area25.78 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity40.15 m³·mol⁻¹ChemAxon
Polarizability15.86 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]+129.55431661259
DarkChem[M-H]-127.19231661259
DeepCCS[M+H]+133.14630932474
DeepCCS[M-H]-130.08830932474
DeepCCS[M-2H]-167.08330932474
DeepCCS[M+Na]+142.19930932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-Ethyl-3,(5 or 6)-dimethylpyrazineCCC1=NC(C)=CN=C1C1430.4Standard polar33892256
2-Ethyl-3,(5 or 6)-dimethylpyrazineCCC1=NC(C)=CN=C1C1030.4Standard non polar33892256
2-Ethyl-3,(5 or 6)-dimethylpyrazineCCC1=NC(C)=CN=C1C1083.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2-Ethyl-3,(5 or 6)-dimethylpyrazine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0079-5900000000-8972bb1f230d4ce37aa02017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Ethyl-3,(5 or 6)-dimethylpyrazine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Ethyl-3,(5 or 6)-dimethylpyrazine 10V, Positive-QTOFsplash10-000i-0900000000-0314177c3c76c33d3a622016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Ethyl-3,(5 or 6)-dimethylpyrazine 20V, Positive-QTOFsplash10-000i-2900000000-17c28b506f498cff1d9f2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Ethyl-3,(5 or 6)-dimethylpyrazine 40V, Positive-QTOFsplash10-00kf-9100000000-53eee1c2cd50606623a02016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Ethyl-3,(5 or 6)-dimethylpyrazine 10V, Negative-QTOFsplash10-000i-0900000000-ec3a2f6d876ea167479f2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Ethyl-3,(5 or 6)-dimethylpyrazine 20V, Negative-QTOFsplash10-000i-1900000000-eb3d7afc9b1afc13d34c2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Ethyl-3,(5 or 6)-dimethylpyrazine 40V, Negative-QTOFsplash10-0ap0-8900000000-4026d008af47668a5d3d2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Ethyl-3,(5 or 6)-dimethylpyrazine 10V, Negative-QTOFsplash10-000i-0900000000-560d709635c029cd0cba2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Ethyl-3,(5 or 6)-dimethylpyrazine 20V, Negative-QTOFsplash10-000i-6900000000-a822bb86992113f3c90b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Ethyl-3,(5 or 6)-dimethylpyrazine 40V, Negative-QTOFsplash10-0f7o-9500000000-43ee0e402d531191a7db2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Ethyl-3,(5 or 6)-dimethylpyrazine 10V, Positive-QTOFsplash10-000i-0900000000-ac299646e14f1770c4b52021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Ethyl-3,(5 or 6)-dimethylpyrazine 20V, Positive-QTOFsplash10-000i-8900000000-14fd5e997abecd36a2f52021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Ethyl-3,(5 or 6)-dimethylpyrazine 40V, Positive-QTOFsplash10-00l6-9000000000-c858357dc68519b94e382021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C 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 IDFDB020022
KNApSAcK IDC00052678
Chemspider ID24145
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound25916
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1426461
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.. .