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, also known as fema 3244, 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 is a moderately basic compound (based on its pKa). Trimethylpyrazine is a cocoa, earthy, and hazelnut tasting compound. Trimethylpyrazine is found, on average, in the highest concentration within kohlrabis. Trimethylpyrazine has also been detected, but not quantified in, several different foods, such as coconuts, tortilla chips, asparagus, potato, and soy beans. This could make trimethylpyrazine a potential biomarker for the consumption of these foods.
CAS Number14667-55-1
Structure
Thumb
Synonyms
SynonymSource
235-Trimethyl-pyrazineHMDB
2,3,5-TRIMETHYL pyrazineHMDB
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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-006x-9200000000-9f6faed991931d5ad1eeJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9200000000-40504210dd3941e2c04aJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-006x-9200000000-9f6faed991931d5ad1eeJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9200000000-40504210dd3941e2c04aJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-8900000000-a14528e7d6edd51f8dc6JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-00di-2900000000-76363ef0f48afd63a91aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 5V, positivesplash10-00di-7900000000-e98f2f5a6e323c824048JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-0ab9-9400000000-35d807ba9ebeef9ae55cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 7V, positivesplash10-0pb9-9100000000-fff3de03d74c83ae57e0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 9V, positivesplash10-0zfr-9000000000-715231eb0f6256a14836JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 8V, positivesplash10-001i-9000000000-9b38357d8213dfc04a21JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 8V, positivesplash10-0a4i-9000000000-5c4795e954d5c3e9b74eJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-9fd5c695f7b8a4cfe63dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-2900000000-bb37b6ad64235815e0f4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zgl-9000000000-8acc5bf685bbdae5968fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-434c116a57f2e3b72058JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0900000000-65f5a51dc79dd6ae5de8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pi0-9800000000-dfd2d2cc903cdbd80f8eJSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-006x-9300000000-0bf83855966f2520d689JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
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).