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2,6-dimethyl pyrazine

Chemical Structure

General Material Information

Preferred name 2,6-dimethyl pyrazine
Trivial Name 2,6-Dimethylpyrazine
Short Description 2,6-dimethylpyrazine
Formula C6 H8 N2
CAS Number 108-50-9
FEMA Number 3273
Flavis Number 14.021
ECHA Number 203-589-4
FDA UNII N77Q72C9I3
Nikkaji Number J1.498B
Beilstein Number 0107052
MDL MFCD00006148
COE Number 2211
NMR Predictor External link
JECFA Food Flavoring 767 2,6-dimethylpyrazine
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 108-50-9 ; 2,6-DIMETHYLPYRAZINE
Synonyms
  • 2,6-dimethyl paradiazine
  • 2,6-dimethyl piazine
  • 2,6-dimethyl pyrazine, kosher
  • 2,6-dimethyl-1,4-diazine
  • dimethyl-2,6 pyrazine
  • 2,6-dimethylparadiazine
  • 2,6-dimethylpiazine
  • 2,6-dimethylpyrazine
  • 2,6 dimethylpyrazine
  • 3,5-dimethylpyrazine
  • 2-methyl-6-methylpyrazine
  • Pyrazine, 2,6-dimethyl-
  • 2,6-Dimethylpyrazine
  • 3,5-Dimethylpyrazine

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

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Literature & References

2,6-dimethylpyrazine
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:108-50-9
Pubchem (cid):7938
Pubchem (sid):134970522
Flavornet:108-50-9
Publications by PubMed
Determination of the alkylpyrazine composition of coffee using stable isotope dilution-gas chromatography-mass spectrometry (SIDA-GC-MS).
Pyrazine analogues are active components of wolf urine that induce avoidance and freezing behaviours in mice.
Mechanistic elucidation of linker and ancillary ligand substitution reactions in Pt(II) dinuclear complexes.
Bis(cyanato-κN)tetra-kis-(2,6-dimethyl-pyrazine-κN(4))nickel(II).
Desalination of fish sauce by electrodialysis: effect on selected aroma compounds and amino acid compositions.
Identification of 2-ethyl-4-methyl-3-thiazoline and 2-isopropyl-4-methyl-3-thiazoline for the first time in nature by the comprehensive analysis of sesame seed oil.
Alkylpyrazines and other volatiles in cocoa liquors at pH 5 to 8, by Selected Ion Flow Tube-Mass Spectrometry (SIFT-MS).
Temporal changes of flavour and texture in cooked bologna type sausages as affected by fat and salt content.
Bioconversion of 2,6-dimethylpyridine to 6-methylpicolinic acid by Exophiala dermatitidis (Kano) de Hoog DA5501 cells grown on n-dodecane.
Coffee aroma--statistical analysis of compositional data.
Syntheses, structures, and photoluminescence of a series of silver(I) sulfonates with pyrazine derivatives.
Suppression of blood lipid concentrations by volatile Maillard reaction products.
Bis(2,6-dimethyl-pyrazine-κN)diiodidozinc(II).
Competition between photochemistry and energy transfer in UV-excited diazabenzenes. 4. UV photodissociation of 2,3-, 2,5-, and 2,6-dimethylpyrazine.
Structural study of silver(I) sulfonate complexes with pyrazine derivatives.
Effect of ripening time and rearing system on amino acid-related flavour compounds of Iberian ham.
Degradation of 2,5-dimethylpyrazine by Rhodococcus erythropolis strain DP-45 isolated from a waste gas treatment plant of a fishmeal processing company.
Characterization of aroma compounds of chinese "Wuliangye" and "Jiannanchun" liquors by aroma extract dilution analysis.
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.
Pyrazine derivatives in cigarette smoke inhibit hamster oviductal functioning.
[Chemical profiles of methylpyrazines contained in commercially available natto].
Identification of aroma compounds in Parmigiano-Reggiano cheese by gas chromatography/olfactometry.
Effects of carnosine on volatile generation from Maillard reaction of ribose and cysteine.
Effect of urea on volatile generation from Maillard reaction of cysteine and ribose.
Chemical and sensory properties of liquid beet sugar.
Pyrazine formation from serine and threonine.
Effects of roasting on pyrazine contents and oxidative stability of red pepper seed oil prior to its extraction.
Quantitative analysis of alkylpyrazines in regular- and low-fat commercial peanut butter preparations.
Genotoxicity of 1,3-dithiane and 1,4-dithiane in the CHO/SCE assay and the Salmonella/microsomal test.
Headspace constituents of opium.
Effects of dimethylpyrazine isomers on reproductive and accessory reproductive organs in male rats.
Publications by J-Stage
Chemical Profiles of Methylpyrazines Contained in Commercially Available Natto
Quantitative Analysis of Alkylpyrazines in Regular- and Low-fat Commercial Peanut Butter Preparations

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
CHEBI:View
HMDB (The Human Metabolome Database):HMDB35248
FooDB:FDB013908
YMDB (Yeast Metabolome Database):YMDB01600
Export Tariff Code:2933.59.9500
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
Melting Point 37 to 48°C @ 760 mm Hg
Boiling Point 154 to 155°C @ 760 mm Hg
Vapor Pressure 3.873 mmHg @ 25 °C
Flash Point TCC Value 52.78 °C TCC
logP (o/w) 0.54
Solubility
alcohol Yes
essential oils Yes
water, 3.816e+004 mg/L @ 25 °C (est) Yes
water No

Organoleptic Properties

Odor Type: Chocolate
ethereal, cocoa, nutty, roasted, meaty roasted meaty, beefy, brown, coffee, buttermilk
Odor strength medium , recommend smelling in a 10.00 % solution or less
Substantivity 37
Luebke, William tgsc, (2021) At 10.00 % in dipropylene glycol. ethereal cocoa nutty roasted roasted meaty beefy brown coffee buttermilk
Flavor Type: Meaty
meaty, nutty, roasted, cocoa, brothy, bready, coffee, musty
Luebke, William tgsc, (2021) Meaty nutty roasted cocoa brothy bready coffee musty
General comment Nutty coffee cocoa musty bready meaty

Occurrences

Potential Uses

Applications
Odor purposes Coffee, Maple, Tobacco
Flavoring purposes Beef roasted beef, Bread, Chocolate cocoa, Nut, Vegetable, Yeast
Other purposes Fried
Cosmetic purposes Perfuming agents

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:
oral-rat LD50 880 mg/kg
Drug and Chemical Toxicology. Vol. 3, Pg. 249, 1980.

intraperitoneal-mouse LD50 1080 mg/kg
Toxicology and Applied Pharmacology. Vol. 17, Pg. 244, 1970.

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 2,6-dimethyl pyrazine usage levels up to:
0.0500 % in the fragrance concentrate.
Maximised Survey-derived Daily Intakes (MSDI-EU): 1.30 (μg/capita/day)
Maximised Survey-derived Daily Intakes (MSDI-USA): 2.00 (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): 0.100005.00000
breakfast cereal: 10.0000010.00000
cheese: --
chewing gum: --
condiments / relishes: 10.0000010.00000
confectionery froastings: --
egg products: --
fats / oils: --
fish products: --
frozen dairy: 10.0000010.00000
fruit ices: --
gelatins / puddings: 10.0000010.00000
granulated sugar: --
gravies: 10.0000010.00000
hard candy: 10.0000010.00000
imitation dairy: --
instant coffee / tea: --
jams / jellies: --
meat products: 10.0000010.00000
milk products: 10.0000010.00000
nut products: --
other grains: --
poultry: --
processed fruits: --
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: --
snack foods: --
soft candy: 10.0000010.00000
soups: 10.0000010.00000
sugar substitutes: --
sweet sauces: --

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):108-50-9
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :7938
National Institute of Allergy and Infectious Diseases:Data
WISER:UN 1325
WGK Germany:3
2,6-dimethylpyrazine
Chemidplus:0000108509
RTECS:UQ2975000 for cas# 108-50-9