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Trimethylpyrazine (FDB008527)

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
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
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
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-9300000000-0bf83855966f2520d6892015-03-01View Spectrum
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-2900000000-76363ef0f48afd63a91a2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 5V, positivesplash10-00di-7900000000-e98f2f5a6e323c8240482020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-0ab9-9400000000-35d807ba9ebeef9ae55c2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 7V, positivesplash10-0pb9-9100000000-fff3de03d74c83ae57e02020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 9V, positivesplash10-0zfr-9000000000-715231eb0f6256a148362020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 8V, positivesplash10-001i-9000000000-9b38357d8213dfc04a212020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 8V, positivesplash10-0a4i-9000000000-5c4795e954d5c3e9b74e2020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-9fd5c695f7b8a4cfe63d2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-2900000000-bb37b6ad64235815e0f42015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zgl-9000000000-8acc5bf685bbdae5968f2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-434c116a57f2e3b720582015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0900000000-65f5a51dc79dd6ae5de82015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pi0-9800000000-dfd2d2cc903cdbd80f8e2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-1fbfd2b4b0ef1b9b6fee2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9400000000-a6ecdcbe708aeefa02c52021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-100u-9000000000-7d5a8bbe136aa07e5c952021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-1900000000-7b36c336b1384f9bab4b2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006x-9300000000-49f0534d4a86e681b4442021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-b33164d500a1075f7e252021-09-24View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
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).