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Showing Compound 2,5-Dimethylpyrazine (FDB013954)

Record Information
Version1.0
Creation date2010-04-08 22:11:00 UTC
Update date2020-09-17 15:36:15 UTC
Primary IDFDB013954
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name2,5-Dimethylpyrazine
Description2,5-Dimethylpyrazine, also known as FEMA 3272 or 2,5-DMP, 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. 2,5-Dimethylpyrazine is also classified as an alkylpyrazine. Alkylpyrazines are naturally occurring highly aromatic substances which often have a very low odor threshold and contribute to the taste and aroma of various foods including coffee and wines. Alkylpyrazines are also formed during the cooking of some foods via Maillard reactions (doi:10.1093/chemse/10.3.287). 2,5-Dimethylpyrazine has a chocolate, roasted, musty, nutty, grassy aroma and a musty potato, nutty or oil taste. 2,5-Dimethylpyrazine occurs naturally in a wide number of foods including asparagus, black or green tea, crispbread, roast beef, beer, roasted coffee, kohlrabi, pork, potato chips, malt, raw shrimp, soya, squid, Swiss cheeses, wheat bread, mung beans, soft-necked garlics, fenugreeks, mollusks, roasted barley, roasted filberts or pecans, wild rice (Zizania aquatica), and wort. 2,5-Dimethylpyrazine is used as flavor additive and odorant in foods such as cereals and products such as cigarettes. It has also been used to artificially scent and enhance the flavour of potato chips.
CAS Number123-32-0
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
25-Dimethyl-pyrazineChEMBL, HMDB
2, 5-DimethylpyrazineHMDB
2,5-Dimethyl pyrazineHMDB
2,5-Dimethyl-1,4-diazineHMDB
2,5-Dimethyl-pyrazineHMDB
2,5-DimethylparadiazineHMDB
2,5-DimethylpiazineHMDB
FEMA 3272HMDB
PYRAZINE,2,5-dimethylHMDB
2,6-DimethylpyrazineMeSH
2,5-DMPMeSH
Pyrazine, 2,5-dimethyl-biospider
PYRAZINE,2,5-DIMETHYLbiospider
Predicted Properties
PropertyValueSource
Water Solubility184 g/LALOGPS
logP0.62ALOGPS
logP-0.2ChemAxon
logS0.23ALOGPS
pKa (Strongest Basic)1.59ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area25.78 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity30.93 m³·mol⁻¹ChemAxon
Polarizability11.91 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC6H8N2
IUPAC name2,5-dimethylpyrazine
InChI IdentifierInChI=1S/C6H8N2/c1-5-3-8-6(2)4-7-5/h3-4H,1-2H3
InChI KeyLCZUOKDVTBMCMX-UHFFFAOYSA-N
Isomeric SMILESCC1=CN=C(C)C=N1
Average Molecular Weight108.1411
Monoisotopic Molecular Weight108.068748266
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

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionC 66.64%; H 7.46%; N 25.90%DFC
Melting PointMp 15°DFC
Boiling PointBp 155°DFC
Experimental Water SolubilityNot Available
Experimental logP0.63HANSCH,C ET AL. (1995)
Experimental pKaNot Available
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
GC-MS2,5-Dimethylpyrazine, non-derivatized, GC-MS Spectrumsplash10-052f-9300000000-081f35e3a3380ed2698bSpectrum
GC-MS2,5-Dimethylpyrazine, non-derivatized, GC-MS Spectrumsplash10-052f-9300000000-081f35e3a3380ed2698bSpectrum
Predicted GC-MS2,5-Dimethylpyrazine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-8900000000-2ada7e902f3d0e2b31e9Spectrum
Predicted GC-MS2,5-Dimethylpyrazine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - , positivesplash10-0a4i-4900000000-7e680d62ffa714f804032017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-9b8f23be4c9d8c94f24d2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1900000000-b0964dc373b182b8f4c42015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0k9x-9000000000-dc3ffe8529561fb7b1cb2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-032c8099a4abe667a4b92015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-58fa248974f5ade4ee462015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-7900000000-890f0c8c1e9a4f4bf6ff2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-1d4d8b4513a0185581992021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-5900000000-53b7bc7c89378de544822021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-d47061f2d3232fef83182021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-3900000000-a2cd546c692d476da7562021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a59-9400000000-696590183181b11c1a142021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udl-9000000000-c5a37365c74d0ec835372021-09-24View Spectrum
NMRNot Available
ChemSpider ID28992
ChEMBL IDCHEMBL94709
KEGG Compound IDNot Available
Pubchem Compound ID31252
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB35289
CRC / DFC (Dictionary of Food Compounds) IDJLL01-V:JLL01-V
EAFUS ID1027
Dr. Duke ID2,5-DIMETHYL-PYRAZINE
BIGG IDNot Available
KNApSAcK IDNot Available
HET ID25R
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID123-32-0
GoodScent IDrw1008141
SuperScent ID31252
Wikipedia ID2,5-Dimethylpyrazine
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
cocoa
  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
  2. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
roasted nut
  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
roast beef
  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
  2. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
medicine
  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
medicinal
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
roasted nuts
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
woody
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
grass
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
medical
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
roastednut
  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
roastbeef
  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
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).