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Record Information
Version3.6
Creation Date2012-09-11 18:58:10 UTC
Update Date2013-06-30 01:23:58 UTC
HMDB IDHMDB34176
Secondary Accession NumbersNone
Metabolite Identification
Common NamePyrazine
DescriptionPyrazine is found in fenugreek. Pyrazine is a maillard 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.
Structure
Thumb
Synonyms
  1. 1, 4-Diazabenzene
  2. 1,4-Diazabenzene
  3. 1,4-Diazin
  4. 1,4-Diazine
  5. 2-Cyanopyrazine
  6. Cyanopyrazine
  7. P-Diazine
  8. Paradiazine
  9. Piazine
  10. Piazine (obsol.)
  11. Pyrazin
  12. PYZ
Chemical FormulaC4H4N2
Average Molecular Weight80.088
Monoisotopic Molecular Weight80.037448138
IUPAC Namepyrazine
Traditional Namepyrazine
CAS Registry Number290-37-9
SMILES
C1=CN=CC=N1
InChI Identifier
InChI=1S/C4H4N2/c1-2-6-4-3-5-1/h1-4H
InChI KeyKYQCOXFCLRTKLS-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAromatic Heteromonocyclic Compounds
ClassDiazines
Sub ClassPyrazines
Other Descriptors
  • Aromatic Heteromonocyclic Compounds
  • diazine(ChEBI)
  • pyrazines(ChEBI)
SubstituentsNone
Direct ParentPyrazines
Ontology
StatusExpected and Not Quantified
Origin
  • Food
Biofunction
  • Nutrient
Application
  • Nutrient
Cellular locations
  • Cytoplasm
  • Extracellular
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting Point54 - 56 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-0.26Not Available
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 Area25.78ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity21.74ChemAxon
Polarizability7.62ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB012468
KNApSAcK IDNot Available
Chemspider ID8904
KEGG Compound IDC02018
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPyrazine
NuGOwiki LinkHMDB34176
Metagene LinkHMDB34176
METLIN IDNot Available
PubChem Compound9261
PDB IDNot Available
ChEBI ID30953
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.