Showing Compound Pyrazine (FDB012468)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:11 UTC

Update date

2019-11-26 03:06:52 UTC

Primary ID

FDB012468

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Pyrazine

Description

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.

CAS Number

290-37-9

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

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Showing 1 to 10 of 15 entries

Predicted Properties

Property	Value	Source
Water Solubility	534 g/L	ALOGPS
logP	-0.29	ALOGPS
logP	-0.46	ChemAxon
logS	0.82	ALOGPS
pKa (Strongest Basic)	0.88	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	25.78 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	21.74 m³·mol⁻¹	ChemAxon
Polarizability	7.62 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C4H4N2

IUPAC name

pyrazine

InChI Identifier

InChI=1S/C4H4N2/c1-2-6-4-3-5-1/h1-4H

InChI Key

KYQCOXFCLRTKLS-UHFFFAOYSA-N

Isomeric SMILES

C1=CN=CC=N1

Average Molecular Weight

80.088

Monoisotopic Molecular Weight

80.037448138

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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazines

Sub Class

Pyrazines

Direct Parent

Pyrazines

Alternative Parents

Substituents

Pyrazine
Heteroaromatic compound
Azacycle
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

pyrazines (CHEBI:30953 )
diazine (CHEBI:30953 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biological:

Plant

Biological location:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Role

Biological role:

Nutrient

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Bp768 115.5-115.8°	DFC
Charge	Not Available
Density	Not Available
Experimental logP	-0.26	HANSCH,C ET AL. (1995)
Experimental pKa	pKa2 0.57 (25°, H2O)	DFC
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	C 59.99%; H 5.03%; N 34.98%	DFC
Melting Point	Mp 54-56° (47°)	DFC
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	Pyrazine, non-derivatized, GC-MS Spectrum	splash10-0ue9-9000000000-a9ecb71c1f0bcbaaf11b	Spectrum
GC-MS	Pyrazine, non-derivatized, GC-MS Spectrum	splash10-0f89-9000000000-0df782a68a2c1241b0fa	Spectrum
GC-MS	Pyrazine, non-derivatized, GC-MS Spectrum	splash10-0ue9-9000000000-a9ecb71c1f0bcbaaf11b	Spectrum
GC-MS	Pyrazine, non-derivatized, GC-MS Spectrum	splash10-0f89-9000000000-0df782a68a2c1241b0fa	Spectrum
Predicted GC-MS	Pyrazine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-001i-9000000000-0d169680fbd08985c9dd	Spectrum
Predicted GC-MS	Pyrazine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Pyrazine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-004i-9000000000-4ab2302c1f18fb749914	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-001i-9000000000-e12a532426f546e87965	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-001i-9000000000-e12a532426f546e87965	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-001i-9000000000-e12a532426f546e87965	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-001i-9000000000-e12a532426f546e87965	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-001i-9000000000-e12a532426f546e87965	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-001i-9000000000-94a5f82e15da219f831a	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-001i-9000000000-94a5f82e15da219f831a	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-001i-9000000000-e12a532426f546e87965	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-001i-9000000000-e12a532426f546e87965	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - APCI-ITFT , positive	splash10-001i-9000000000-a5db0ef57f8fb4432902	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - APCI-ITFT , positive	splash10-001i-9000000000-a5db0ef57f8fb4432902	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - APCI-ITFT , positive	splash10-001i-9000000000-67966ad1ea4c70f96224	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - APCI-ITFT , positive	splash10-001i-9000000000-a5db0ef57f8fb4432902	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - APCI-ITFT , positive	splash10-001i-9000000000-67966ad1ea4c70f96224	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - APCI-ITFT , positive	splash10-001i-9000000000-67966ad1ea4c70f96224	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - APCI-ITFT , positive	splash10-001i-9000000000-67966ad1ea4c70f96224	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - APCI-ITFT , positive	splash10-001i-9000000000-a5db0ef57f8fb4432902	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - APCI-ITFT , positive	splash10-001i-9000000000-67966ad1ea4c70f96224	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-9000000000-73d255a36568e9413c78	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-9000000000-c9bce48c51da920d5cd5	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0zgi-9000000000-fdb72ce6f5a40ea431f8	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-9000000000-7b4264e953d5ba3b2c75	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9000000000-88728ef69d13e92d73d6	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-461c3e6869f2758a24af	2016-08-03	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

30953

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB34176

CRC / DFC (Dictionary of Food Compounds) ID

HHF58-P:HHF58-P

EAFUS ID

3256

Dr. Duke ID

PYRAZINE

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1040421

SuperScent ID

Not Available

Wikipedia ID

Pyrazine

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

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Flavor	Citations
barley	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
hazelnut	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
pungent	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
roasted	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sweet corn	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.