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2,3-dimethyl pyrazine

Chemical Structure

General Material Information

Preferred name 2,3-dimethyl pyrazine
Trivial Name 2,3-Dimethylpyrazine
Short Description 2,3-dimethylpyrazine
Formula C6 H8 N2
CAS Number 5910-89-4
FEMA Number 3271
Flavis Number 14.05
ECHA Number 227-630-0
FDA UNII WHF7883D0V
Nikkaji Number J45.570I
MDL MFCD00006144
COE Number 11323
NMR Predictor External link
JECFA Food Flavoring 765 2,3-dimethylpyrazine
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 5910-89-4 ; 2,3-DIMETHYLPYRAZINE
Synonyms
  • 2,3-dimethyl pyrazine FCC
  • 2,3-dimethyl pyrazine natural 5% in ethyl alcohol
  • 2,3-dimethyl pyrazine natural 5% in ethyl alcohol, kosher
  • 2,3-dimethyl pyrazine, kosher
  • 2,3-dimethyl-1,4-diazine
  • dimethyl-2,3 pyrazine
  • 2,3-dimethyl-pyrazine
  • 2,3-dimethylpyrazin
  • 2, 3 dimethylpyrazine
  • 2,3-dimethylpyrazine
  • 2,3-dimethylpyrazine, kosher
  • pyrazine, 2,3-dimethyl-
  • pyrazine, dimethyl-
  • 2,3-Dimethylpyrazine

US / EU / FDA / JECFA / FEMA / Scholar / Patents

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Literature & References

2,3-dimethylpyrazine
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:5910-89-4
Pubchem (cid):22201
Pubchem (sid):134987453
Flavornet:5910-89-4
Publications by US Patents
3,931,166 - Certain 2,5-dimethyl-3-thiopyrazines
Publications by PubMed
Relevant and unprecedented C-H/σ supramolecular interactions involving σ-aromatic M2X2 cores.
Determination of the alkylpyrazine composition of coffee using stable isotope dilution-gas chromatography-mass spectrometry (SIDA-GC-MS).
Volatile profiling of high quality hazelnuts (Corylus avellana L.): chemical indices of roasting.
Odorant-evoked electrical responses in Grueneberg ganglion neurons rely on cGMP-associated signaling proteins.
Double Schiff base adducts of 2,3-butanedione with glycine: formation of pyrazine rings with the participation of amino acid carbon atoms.
Characterization of cocoa liquors by GC-MS and LC-MS/MS: focus on alkylpyrazines and flavanols.
Comparison of fermented soybean paste (Doenjang) prepared by different methods based on profiling of volatile compounds.
Phorid fly, Pseudacteon tricuspis, response to alkylpyrazine analogs of a fire ant, Solenopsis invicta, alarm pheromone.
Crystal transformation and host molecular motions in CO2 adsorption process of a metal benzoate pyrazine (M(II) = Rh, Cu).
Biodegradation of the major color containing compounds in distillery wastewater by an aerobic bacterial culture and characterization of their metabolites.
Syntheses, structures, and photoluminescence of a series of silver(I) sulfonates with pyrazine derivatives.
Structural study of silver(I) sulfonate complexes with pyrazine derivatives.
Synthesis, crystal structure, thermal and luminescence properties of CuX(2,3-dimethylpyrazine) (X=Cl, Br, I) coordination polymers.
Construction of polyoxometalates-based coordination polymers through direct incorporation between polyoxometalates and the voids in a 2D network.
Degradation of 2,5-dimethylpyrazine by Rhodococcus erythropolis strain DP-45 isolated from a waste gas treatment plant of a fishmeal processing company.
Investigations on the synthesis, structures, and properties of new copper(I) 2,3-dimethylpyrazine coordination compounds.
Effect of citric acid and glycine addition on acrylamide and flavor in a potato model system.
Influence of steric hindrance of organic ligand on the structure of Keggin-based coordination polymer.
Identification of components responsible for the odor of cigar smoker's breath.
Determination of the 2H/1H and 15N/14N ratios of Alkylpyrazines from coffee beans (Coffea arabica L. and Coffea canephoravar. robusta) by isotope ratio mass spectrometry.
Aroma compounds in sweet whey powder.
Effects of static vs. tidal hydrology on pollutant transformation in wetland sediments.
Growth and angiogenesis are inhibited in vivo in developing tissues by pyrazine and its derivatives.
Thermal decomposition of specifically phosphorylated D-glucoses and their role in the control of the Maillard reaction.
A study by ultraviolet spectroscopy on the self-association of diazines in aqueous solution.
Identification of aroma compounds in Parmigiano-Reggiano cheese by gas chromatography/olfactometry.
Use of gas chromatography-olfactometry to identify key odorant compounds in dark chocolate. Comparison of samples before and after conching.
Poly[copper(I)-mu-bromo-mu-2,3-dimethylpyrazine-N:N'].
Effects of olive, canola, and sunflower oils on the formation of volatiles from the Maillard reaction of lysine with xylose and glucose.
2,3-dimethyl-5-(2-methylpropyl)pyrazine, a trail pheromone component of Eutetramorium mocquerysi Emery (1899) (Hymenoptera: Formicidae).
Formation of sugar-specific reactive intermediates from (13)C-labeled L-serines.
Effects of Maillard reaction products on mutagen formation in boiled pork juice.
Effects of dimethylpyrazine isomers on reproductive and accessory reproductive organs in male rats.

Other Information

(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
FDA Substances Added to Food (formerly EAFUS):View
CHEMBL:View
HMDB (The Human Metabolome Database):HMDB32971
FooDB:FDB010958
Export Tariff Code:2933.99.8210
Typical G.C.
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View

PhysChem Properties

Material listed in food chemical codex Yes
Molecular weight 108.14376068115
Specific gravity @ 25 °C
Pounds per Gallon 8.296 to 8.479
Specific gravity @ 25 °C
Pounds per Gallon 8.296 to 8.571
Refractive Index 1.506 to 1.509 @ 20 °C
Refractive Index 1.501 to 1.51 @ 20 °C
Boiling Point 155 to 157°C @ 760 mm Hg
Vapor Pressure 3.449 mmHg @ 25 °C
Vapor Density 3.7
Flash Point TCC Value 53.33 °C TCC
logP (o/w) 0.54
Solubility
alcohol Yes
ether Yes
water, 3.816e+004 mg/L @ 25 °C (est) Yes
Stability
non-discoloring in most media Unspecified
stable in most media Unspecified

Organoleptic Properties

Odor Type: Nutty
nutty, nut skin, cocoa, peanut butter, coffee, walnut, caramellic, roasted, musty, powdery, potato
Odor strength high , recommend smelling in a 0.10 % solution or less
Substantivity < 3 hour(s) at 100.00 %
Luebke, William tgsc, (2017) At 0.10 % in dipropylene glycol. nutty nut skin cocoa peanut butter coffee walnut caramellic roasted
Mosciano, Gerard P&F 21, No. 6, 49, (1996) Musty, nut skins, cocoa powdery and roasted with potato and coffee nuances
Flavor Type: Nutty
nutty, nut skin, peanut, cocoa, coffee roasted coffee, walnut, corn chip, bready, musty, powdery, roasted, coffee
Luebke, William tgsc, (2017) Nutty nut skin peanut cocoa roasted coffee walnut corn chip bready
Mosciano, Gerard P&F 21, No. 6, 49, (1996) At 7.50 ppm. Musty, nut skins, cocoa powdery, roasted coffee and bready
Used in meat, coffee, cocoa, soup and gravy products. Meaty
Used in baked and dairy products, gravies, beverages, at 10ppm. Nutty

Occurrences

Potential Uses

Applications
Odor purposes Chocolate, Coffee, Hazelnut, Peanut, Popcorn
Flavoring purposes Bread, Chocolate cocoa, Meat, Roasted, Shellfish, Soup, Vegetable

Safety Information

Safety information

Preferred SDS: View
European information :
Most important hazard(s):
Xn - Harmful.
R 10 - Flammable.
R 22 - Harmful if swallowed.
R 36/37/38 - Irritating to eyes, respiratory system, and skin.
S 02 - Keep out of the reach of children.
S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S 36/37/39 - Wear suitable clothing, gloves and eye/face protection.
Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
Pictogram
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
gavage-rat LD50 613 mg/kg
(Moran et al., 1980)

intraperitoneal-mouse LD50 1390 mg/kg
Toxicology and Applied Pharmacology. Vol. 17, Pg. 244, 1970.

oral-rat LD50 613 mg/kg
Drug and Chemical Toxicology. Vol. 3, Pg. 249, 1980.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined

Safety in use information

Category:
flavor and fragrance agents
RIFM Fragrance Material Safety Assessment: Search
IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice
Recommendation for 2,3-dimethyl pyrazine usage levels up to:
0.0500 % in the fragrance concentrate.
Maximised Survey-derived Daily Intakes (MSDI-EU): 14.00 (μg/capita/day)
Maximised Survey-derived Daily Intakes (MSDI-USA): 4.00 (μg/capita/day)
Structure Class: II
Use levels for FEMA GRAS flavoring substances on which the FEMA Expert Panel based its judgments that the substances are generally recognized as safe (GRAS).
The Expert Panel also publishes separate extensive reviews of scientific information on all FEMA GRAS flavoring substances and can be found at FEMA Flavor Ingredient Library
publication number: 5. Update in publication number(s): 29
Click here to view publication 5
average usual ppmaverage maximum ppm
baked goods: 10.0000010.00000
beverages(nonalcoholic): 10.0000010.00000
beverages(alcoholic): 0.002002.00000
breakfast cereal: 0.100001.00000
cheese: 0.100001.00000
chewing gum: 1.000001.00000
condiments / relishes: 0.100001.00000
confectionery froastings: 0.100001.00000
egg products: 0.100001.00000
fats / oils: 0.100001.00000
fish products: 0.100001.00000
frozen dairy: 10.0000010.00000
fruit ices: --
gelatins / puddings: 10.0000010.00000
granulated sugar: 0.100001.00000
gravies: 10.0000010.00000
hard candy: 10.0000010.00000
imitation dairy: 0.100001.00000
instant coffee / tea: 0.100001.00000
jams / jellies: 0.100001.00000
meat products: 10.0000010.00000
milk products: 0.100001.00000
nut products: --
other grains: 0.100001.00000
poultry: 0.100001.00000
processed fruits: --
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: 1.0000010.00000
snack foods: 0.100001.00000
soft candy: 10.0000010.00000
soups: 0.100001.00000
sugar substitutes: 0.100001.00000
sweet sauces: 0.100001.00000

Safety references

European Food Safety Athority(EFSA):Flavor usage levels; Subacute, Subchronic, Chronic and Carcinogenicity Studies; Developmental / Reproductive Toxicity Studies; Genotoxicity Studies...

European Food Safety Authority (EFSA) reference(s):

Opinion of the Scientific Panel on food additives, flavourings, processing aids and materials in contact with food (AFC) on a request from the Commission related to Flavouring Group Evaluation 17 (FGE.17): Pyrazine derivatives from chemical group 24 (Commission Regulation (EC) No 1565/2000 of 18 July 2000)
View page or View pdf

Flavouring Group Evaluation 50 (FGE.50): Consideration of pyrazine derivatives evaluated by JECFA (57th meeting) structurally related to pyrazine derivatives evaluated by EFSA in FGE.17 (2005) (Commission Regulation (EC) No 1565/2000 of 18 July 2000) - Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC)
View page or View pdf

Flavouring Group Evaluation 17, Revision 1 (FGE.17Rev1): Pyrazine derivatives from chemical group 24 - Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC) [1]
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 17, Revision 2 (FGE.17Rev2): Pyrazine derivatives from chemical group 24
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 50, Revision 1 (FGE.50Rev1): Consideration of pyrazine derivatives evaluated by JECFA (57th meeting) structurally related to pyrazine derivatives evaluated by EFSA in FGE.17Rev2 (2010)
View page or View pdf

Safety and efficacy of pyrazine derivatives including saturated ones belonging to chemical group 24 when used as flavourings for all animal species
View page or View pdf

EPI System: View
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):5910-89-4
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :22201
National Institute of Allergy and Infectious Diseases:Data
WISER:UN 1993
WGK Germany:3
2,3-dimethylpyrazine
Chemidplus:0005910894
RTECS:UQ2625000 for cas# 5910-89-4