Record Information
Version1.0
Creation date2010-04-08 22:10:11 UTC
Update date2019-11-26 03:06:52 UTC
Primary IDFDB012468
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePyrazine
DescriptionMaillard product In the Staedel-Rugheimer pyrazine synthesis (1876) 2-chloroacetophenone is reacted with ammonia to the amino ketone, then condensed and then oxidized to a pyrazine A variation is the Gutknecht Pyrazine Synthesis (1879) also based on this selfcondensation but differing in the way the alpha-ketoamine is synthesised (the chlorine compound in the above method is a lachrymatory agent); Pyrazine is a heterocyclic aromatic organic compound.; Pyrazine is a symmetrical molecule with point group D2h. It is found in folic acid in the form of pterin. Derivatives like Phenazine are well known for their antitumor, antibiotic and diuretic activity. Pyrazine is less basic in nature than pyridine, pyridazine and pyrimidine. Tetramethylpyrazine (also known as ligustrazine) is reported to scavenge superoxide anion and decrease nitric oxide production in human polymorphonuclear leukocytes. Tetramethylpyrazine is also a component of some herbs in Traditional Chinese Medicine.
CAS Number290-37-9
Structure
Thumb
Synonyms
SynonymSource
1,4-DiazinChEBI
1,4-DiazineChEBI
p-DiazineChEBI
ParadiazineChEBI
PyrazinChEBI
pyzChEBI
1, 4-DiazabenzeneHMDB
1,4-DiazabenzeneHMDB
2-CyanopyrazineHMDB
CyanopyrazineHMDB
PiazineHMDB
Piazine (obsol.)HMDB
P-diazinebiospider
PYZbiospider
Predicted Properties
PropertyValueSource
Water Solubility534 g/LALOGPS
logP-0.29ALOGPS
logP-0.46ChemAxon
logS0.82ALOGPS
pKa (Strongest Basic)0.88ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area25.78 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity21.74 m³·mol⁻¹ChemAxon
Polarizability7.62 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC4H4N2
IUPAC namepyrazine
InChI IdentifierInChI=1S/C4H4N2/c1-2-6-4-3-5-1/h1-4H
InChI KeyKYQCOXFCLRTKLS-UHFFFAOYSA-N
Isomeric SMILESC1=CN=CC=N1
Average Molecular Weight80.088
Monoisotopic Molecular Weight80.037448138
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 Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 59.99%; H 5.03%; N 34.98%DFC
Melting PointMp 54-56° (47°)DFC
Boiling PointBp768 115.5-115.8°DFC
Experimental Water SolubilityNot Available
Experimental logP-0.26HANSCH,C ET AL. (1995)
Experimental pKapKa2 0.57 (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)splash10-0ue9-9000000000-a9ecb71c1f0bcbaaf11bJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0f89-9000000000-0df782a68a2c1241b0faJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0ue9-9000000000-a9ecb71c1f0bcbaaf11bJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0f89-9000000000-0df782a68a2c1241b0faJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9000000000-0d169680fbd08985c9ddJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-004i-9000000000-4ab2302c1f18fb749914JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-001i-9000000000-e12a532426f546e87965JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-001i-9000000000-e12a532426f546e87965JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-001i-9000000000-e12a532426f546e87965JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-001i-9000000000-e12a532426f546e87965JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-001i-9000000000-e12a532426f546e87965JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-001i-9000000000-94a5f82e15da219f831aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-001i-9000000000-94a5f82e15da219f831aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-001i-9000000000-e12a532426f546e87965JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-001i-9000000000-e12a532426f546e87965JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-001i-9000000000-a5db0ef57f8fb4432902JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-001i-9000000000-a5db0ef57f8fb4432902JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-001i-9000000000-67966ad1ea4c70f96224JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-001i-9000000000-a5db0ef57f8fb4432902JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-001i-9000000000-67966ad1ea4c70f96224JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-001i-9000000000-67966ad1ea4c70f96224JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-001i-9000000000-67966ad1ea4c70f96224JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-001i-9000000000-a5db0ef57f8fb4432902JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-001i-9000000000-67966ad1ea4c70f96224JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-9000000000-73d255a36568e9413c78JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-9000000000-c9bce48c51da920d5cd5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zgi-9000000000-fdb72ce6f5a40ea431f8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-9000000000-7b4264e953d5ba3b2c75JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-88728ef69d13e92d73d6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-461c3e6869f2758a24afJSpectraViewer
ChemSpider ID8904
ChEMBL IDCHEMBL15797
KEGG Compound IDC02018
Pubchem Compound ID9261
Pubchem Substance IDNot Available
ChEBI ID30953
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB34176
CRC / DFC (Dictionary of Food Compounds) IDHHF58-P:HHF58-P
EAFUS ID3256
Dr. Duke IDPYRAZINE
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1040421
SuperScent IDNot Available
Wikipedia IDPyrazine
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
pungent
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sweet corn
  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.
hazelnut
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
barley
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSshow
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).