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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:45:55 UTC
Update Date2019-07-23 06:09:39 UTC
HMDB IDHMDB0031844
Secondary Accession Numbers
  • HMDB31844
Metabolite Identification
Common 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. Outside of the human body, trimethylpyrazine is found, on average, in the highest concentration in kohlrabis. trimethylpyrazine has also been detected, but not quantified in, several different foods, such as green vegetables, pepper (c. annuum), orange bell peppers, potato, and red bell peppers. This could make trimethylpyrazine a potential biomarker for the consumption of these foods. Found in many foodstuffs e.g. asparagus, baked potato, wheat bread, Swiss cheese, coffee, black tea, roasted filbert and peanut, soybean etc.
Structure
Data?1563862179
Synonyms
ValueSource
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
Chemical FormulaC7H10N2
Average Molecular Weight122.1677
Monoisotopic Molecular Weight122.08439833
IUPAC Name2,3,5-trimethylpyrazine
Traditional Namepyrazine, trimethyl-
CAS Registry Number14667-55-1
SMILES
CC1=NC(C)=C(C)N=C1
InChI Identifier
InChI=1S/C7H10N2/c1-5-4-8-6(2)7(3)9-5/h4H,1-3H3
InChI KeyIAEGWXHKWJGQAZ-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 ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP0.95Not 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
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-006x-9200000000-9f6faed991931d5ad1eeSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9200000000-40504210dd3941e2c04aSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-006x-9200000000-9f6faed991931d5ad1eeSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9200000000-40504210dd3941e2c04aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-8900000000-a14528e7d6edd51f8dc6Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-00di-2900000000-76363ef0f48afd63a91aSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 5V, positivesplash10-00di-7900000000-e98f2f5a6e323c824048Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-0ab9-9400000000-35d807ba9ebeef9ae55cSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 7V, positivesplash10-0pb9-9100000000-fff3de03d74c83ae57e0Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 9V, positivesplash10-0zfr-9000000000-715231eb0f6256a14836Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 8V, positivesplash10-001i-9000000000-9b38357d8213dfc04a21Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 8V, positivesplash10-0a4i-9000000000-5c4795e954d5c3e9b74eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-9fd5c695f7b8a4cfe63dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-2900000000-bb37b6ad64235815e0f4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zgl-9000000000-8acc5bf685bbdae5968fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-434c116a57f2e3b72058Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0900000000-65f5a51dc79dd6ae5de8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pi0-9800000000-dfd2d2cc903cdbd80f8eSpectrum
MSMass Spectrum (Electron Ionization)splash10-006x-9300000000-0bf83855966f2520d689Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
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 IDFDB008527
KNApSAcK IDNot Available
Chemspider ID24972
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAlkylpyrazine
METLIN IDNot Available
PubChem Compound26808
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Van Lancker F, Adams A, De Kimpe N: Impact of the N-terminal amino acid on the formation of pyrazines from peptides in Maillard model systems. J Agric Food Chem. 2012 May 9;60(18):4697-708. doi: 10.1021/jf301315b. Epub 2012 Apr 25. [PubMed:22463717 ]
  2. Bohman B, Jeffares L, Flematti G, Byrne LT, Skelton BW, Phillips RD, Dixon KW, Peakall R, Barrow RA: Discovery of tetrasubstituted pyrazines as semiochemicals in a sexually deceptive orchid. J Nat Prod. 2012 Sep 28;75(9):1589-94. Epub 2012 Sep 18. [PubMed:22988937 ]
  3. Zhai L, Zhang P, Sun RY, Liu XY, Liu WG, Guo XL: Cytoprotective effects of CSTMP, a novel stilbene derivative, against H2O2-induced oxidative stress in human endothelial cells. Pharmacol Rep. 2011;63(6):1469-80. [PubMed:22358095 ]
  4. Li S, Chen H, Wang X, Wu J, Jiang J, Wang Y: Pharmacokinetic study of a novel stroke therapeutic, 2-[[(1,1-dimethylethyl)oxidoimino]methyl]-3,5,6-trimethylpyrazine, by a simple HPLC-UV method in rats. Eur J Drug Metab Pharmacokinet. 2011 Jun;36(2):95-101. doi: 10.1007/s13318-011-0032-2. Epub 2011 Mar 22. [PubMed:21424683 ]
  5. Divine RD, Sommer D, Lopez-Hernandez A, Rankin SA: Short communication: Evidence for methylglyoxal-mediated browning of Parmesan cheese during low temperature storage. J Dairy Sci. 2012 May;95(5):2347-54. doi: 10.3168/jds.2011-4828. [PubMed:22541463 ]
  6. Yang XZ, Yang WH, Xu YG, Diao XJ, He GW, Gong GQ: Synthesis and antithrombotic evaluation of novel dabigatran prodrugs containing a cleavable moiety with anti-platelet activity. Eur J Med Chem. 2012 Nov;57:21-8. doi: 10.1016/j.ejmech.2012.09.016. Epub 2012 Sep 18. [PubMed:23043765 ]
  7. Ren M, Dong J, Xu Y, Wen N, Gong G: Synthesis of novel ligustrazine derivatives as NA+/H+ exchange inhibitors. Chem Biodivers. 2010 Nov;7(11):2727-36. doi: 10.1002/cbdv.200900353. [PubMed:21072772 ]
  8. Huang Y, Barringer SA: Alkylpyrazines and other volatiles in cocoa liquors at pH 5 to 8, by Selected Ion Flow Tube-Mass Spectrometry (SIFT-MS). J Food Sci. 2010 Jan-Feb;75(1):C121-7. doi: 10.1111/j.1750-3841.2009.01455.x. [PubMed:20492142 ]
  9. Magi E, Bono L, Di Carro M: Characterization of cocoa liquors by GC-MS and LC-MS/MS: focus on alkylpyrazines and flavanols. J Mass Spectrom. 2012 Sep;47(9):1191-7. doi: 10.1002/jms.3034. [PubMed:22972787 ]
  10. Qin P, Ma T, Wu L, Shan F, Ren G: Identification of tartary buckwheat tea aroma compounds with gas chromatography-mass spectrometry. J Food Sci. 2011 Aug;76(6):S401-7. doi: 10.1111/j.1750-3841.2011.02223.x. Epub 2011 Jun 8. [PubMed:22417522 ]
  11. Huang Y, Barringer SA: Monitoring of cocoa volatiles produced during roasting by selected ion flow tube-mass spectrometry (SIFT-MS). J Food Sci. 2011 Mar;76(2):C279-86. doi: 10.1111/j.1750-3841.2010.01984.x. Epub 2011 Feb 1. [PubMed:21535747 ]
  12. Sun Y, Yu P, Zhang G, Wang L, Zhong H, Zhai Z, Wang L, Wang Y: Therapeutic effects of tetramethylpyrazine nitrone in rat ischemic stroke models. J Neurosci Res. 2012 Aug;90(8):1662-9. doi: 10.1002/jnr.23034. Epub 2012 Mar 19. [PubMed:22431378 ]
  13. Sharp MD, Kocaoglu-Vurma NA, Langford V, Rodriguez-Saona LE, Harper WJ: Rapid discrimination and characterization of vanilla bean extracts by attenuated total reflection infrared spectroscopy and selected ion flow tube mass spectrometry. J Food Sci. 2012 Mar;77(3):C284-92. doi: 10.1111/j.1750-3841.2011.02544.x. [PubMed:22384952 ]
  14. Guerra PV, Yaylayan VA: Double Schiff base adducts of 2,3-butanedione with glycine: formation of pyrazine rings with the participation of amino acid carbon atoms. J Agric Food Chem. 2012 Nov 14;60(45):11440-5. doi: 10.1021/jf303658m. Epub 2012 Nov 6. [PubMed:23106172 ]
  15. Ishida T, Takechi S, Yamaguchi T: Possible involvement of glutathione balance disruption in dihydropyrazine-induced cytotoxicity on human hepatoma HepG2 cells. J Toxicol Sci. 2012;37(5):1065-9. [PubMed:23038014 ]
  16. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .