Record Information
Version1.0
Creation date2010-04-08 22:08:07 UTC
Update date2019-11-26 03:02:43 UTC
Primary IDFDB008527
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameTrimethylpyrazine
DescriptionTrimethylpyrazine 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. Trimethylpyrazine exists in all eukaryotes, ranging from yeast to plants to humans. Trimethylpyrazine is a cocoa, earthy, and hazelnut tasting compound. Trimethylpyrazine is found, on average, in the highest concentration within kohlrabis (Brassica oleracea var. gongylodes). Trimethylpyrazine has also been detected, but not quantified in, several different foods, such as teas (Camellia sinensis), herbal tea, coconuts (Cocos nucifera), green vegetables, and soy beans (Glycine max). This could make trimethylpyrazine a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Trimethylpyrazine.
CAS Number14667-55-1
Structure
Thumb
Synonyms
SynonymSource
235-Trimethyl-pyrazineChEMBL, HMDB
2,3,5-TRIMETHYL pyrazineHMDB, MeSH
2,3,5-Trimethyl-pyrazineHMDB
2,3,6-TrimethylpyrazineHMDB
FEMA 3244HMDB
Pyrazine, 2,3,5-trimethylHMDB
Trimethyl-pyrazineHMDB
2,3,5-TRIMETHYL PYRAZINEbiospider
2,3,5-Trimethylpyrazinebiospider
pyrazine, 2,3,5-trimethylbiospider
Pyrazine, 2,3,5-trimethyl-biospider
Pyrazine, trimethyl-biospider
Predicted Properties
PropertyValueSource
Water Solubility51.6 g/LALOGPS
logP1.11ALOGPS
logP-0.068ChemAxon
logS-0.37ALOGPS
pKa (Strongest Basic)2.08ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area25.78 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity35.52 m³·mol⁻¹ChemAxon
Polarizability13.94 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC7H10N2
IUPAC name2,3,5-trimethylpyrazine
InChI IdentifierInChI=1S/C7H10N2/c1-5-4-8-6(2)7(3)9-5/h4H,1-3H3
InChI KeyIAEGWXHKWJGQAZ-UHFFFAOYSA-N
Isomeric SMILESCC1=NC(C)=C(C)N=C1
Average Molecular Weight122.1677
Monoisotopic Molecular Weight122.08439833
Classification
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

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 68.82%; H 8.25%; N 22.93%DFC
Melting PointNot Available
Boiling PointBp735 171-172°DFC
Experimental Water SolubilityNot Available
Experimental logP0.95YAMAGAMI,C ET AL. (1991)
Experimental pKapKa2 -3.6 (25°, H2O)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-006x-9300000000-0bf83855966f2520d689Spectrum
GC-MSTrimethylpyrazine, non-derivatized, GC-MS Spectrumsplash10-006x-9200000000-9f6faed991931d5ad1eeSpectrum
GC-MSTrimethylpyrazine, non-derivatized, GC-MS Spectrumsplash10-0006-9200000000-40504210dd3941e2c04aSpectrum
GC-MSTrimethylpyrazine, non-derivatized, GC-MS Spectrumsplash10-006x-9200000000-9f6faed991931d5ad1eeSpectrum
GC-MSTrimethylpyrazine, non-derivatized, GC-MS Spectrumsplash10-0006-9200000000-40504210dd3941e2c04aSpectrum
Predicted GC-MSTrimethylpyrazine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-8900000000-a14528e7d6edd51f8dc6Spectrum
Predicted GC-MSTrimethylpyrazine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-00di-2900000000-76363ef0f48afd63a91aSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 5V, positivesplash10-00di-7900000000-e98f2f5a6e323c824048Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-0ab9-9400000000-35d807ba9ebeef9ae55cSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 7V, positivesplash10-0pb9-9100000000-fff3de03d74c83ae57e0Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 9V, positivesplash10-0zfr-9000000000-715231eb0f6256a14836Spectrum
MS/MSLC-MS/MS Spectrum - n/a 8V, positivesplash10-001i-9000000000-9b38357d8213dfc04a21Spectrum
MS/MSLC-MS/MS Spectrum - n/a 8V, positivesplash10-0a4i-9000000000-5c4795e954d5c3e9b74eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-9fd5c695f7b8a4cfe63dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-2900000000-bb37b6ad64235815e0f4Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zgl-9000000000-8acc5bf685bbdae5968fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-434c116a57f2e3b72058Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0900000000-65f5a51dc79dd6ae5de8Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pi0-9800000000-dfd2d2cc903cdbd80f8eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-1fbfd2b4b0ef1b9b6feeSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9400000000-a6ecdcbe708aeefa02c5Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-100u-9000000000-7d5a8bbe136aa07e5c95Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-1900000000-7b36c336b1384f9bab4bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006x-9300000000-49f0534d4a86e681b444Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-b33164d500a1075f7e25Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
ChemSpider ID24972
ChEMBL IDCHEMBL320146
KEGG Compound IDNot Available
Pubchem Compound ID26808
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB31844
CRC / DFC (Dictionary of Food Compounds) IDDMZ82-F:DMZ82-F
EAFUS ID3767
Dr. Duke ID2,3,5-TRIMETHYLPYRAZINE|TRIMETHYL-PYRAZINE
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID14667-55-1
GoodScent IDrw1012941
SuperScent ID26808
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
roast
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
potato
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
must
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
hazelnut
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
peanut
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
  2. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
nutty
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
musty
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
earthy
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
powdery
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
cocoa
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
roasted
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).