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2,5-dimethyl pyrazine

Chemical Structure

General Material Information

Preferred name 2,5-dimethyl pyrazine
Trivial Name 2,5-Dimethylpyrazine
Short Description 2,5-dimethylpyrazine
Formula C6 H8 N2
CAS Number 123-32-0
FEMA Number 3272
Flavis Number 14.02
ECHA Number 204-618-3
FDA UNII V99Y0MUY1Q
Nikkaji Number J2.009E
Beilstein Number 0107052
MDL MFCD00006147
COE Number 2210
NMR Predictor External link
JECFA Food Flavoring 766 2,5-dimethylpyrazine
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 123-32-0 ; 2,5-DIMETHYLPYRAZINE
Synonyms
  • 2,5-dimethyl paradiazine
  • 2,5-dimethyl piazine
  • 2,5-dimethyl pyrazine natural
  • 2,5-dimethyl pyrazine, natural
  • 2,5-dimethyl-1,4-diazine
  • 2,5-dimethyl-pyrazine
  • 2,5-dimethylparadiazine
  • 2,5-dimethylpiazine
  • 2, 5 dimethylpyrazine
  • 2,5-dimethylpyrazine
  • 2,5-dimethylpyrazine >80.0%(gc) (contains 2,6-isomer)
  • ketine
  • pyrazine, 2,5-dimethyl
  • pyrazine, 2,5-dimethyl-
  • 2,5-Dimethylpyrazine
  • NSC 49139

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

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Literature & References

2,5-dimethylpyrazine
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:123-32-0
Pubchem (cid):31252
Pubchem (sid):134974393
Flavornet:123-32-0
Pherobase:View
Publications by PubMed
Relationship of sensory and instrumental aroma measurements of dark chocolate as influenced by fermentation method, roasting and conching conditions.
HS-SPME GC/MS characterization of volatiles in raw and dry-roasted almonds (Prunus dulcis).
Chemical communication during foraging in the harvesting ants Messor pergandei and Messor andrei.
Headspace-solid phase microextraction-gas chromatography-tandem mass spectrometry (HS-SPME-GC-MS2) method for the determination of pyrazines in perilla seed oils: impact of roasting on the pyrazines in perilla seed oils.
Stimulation of cell proliferation in the subventricular zone by synthetic murine pheromones.
Determination of the alkylpyrazine composition of coffee using stable isotope dilution-gas chromatography-mass spectrometry (SIDA-GC-MS).
Comparison of direct mass spectrometry methods for the on-line analysis of volatile compounds in foods.
Volatile profiling of high quality hazelnuts (Corylus avellana L.): chemical indices of roasting.
Characterization of cocoa liquors by GC-MS and LC-MS/MS: focus on alkylpyrazines and flavanols.
[Balance hypothesis of action of socially significant volatile chemosignals on reactivity of chromosome machinery of the bone marrow dividing cells in the house mouse Mus domesticus L].
[Action of two pyrazine-containing chemosignals on cells of bone marrow and testes in male house mouse Mus musculus L].
Volatile compounds of black cumin seeds (Nigella sativa L.) from microwave-heating and conventional roasting.
Identification of tartary buckwheat tea aroma compounds with gas chromatography-mass spectrometry.
GC-MS based metabolomics for rapid simultaneous detection of Escherichia coli O157:H7, Salmonella Typhimurium, Salmonella Muenchen, and Salmonella Hartford in ground beef and chicken.
[The role of metabolic activation of promutagens in the genome destabilization under pheromonal stress in the house mouse (Mus musculus)].
Effects of roasting conditions on the physicochemical properties and volatile distribution in perilla oils (Perilla frutescens var. japonica).
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.
Grueneberg ganglion neurons are activated by a defined set of odorants.
Volatile composition and sensory analysis of Italian gianduja torrone.
High resolution X-ray structures of mouse major urinary protein nasal isoform in complex with pheromones.
catena-Poly[[[diaqua-bis(8-hydroxy-quinoline N-oxide-κO)cobalt(II)]-μ-2,5-dimethyl-pyrazine 1,4-dioxide-κO:O] bis-(perchlorate)].
[Effects of "pheromone-like" pyrazine-containing substances on stability of genetic apparatus in bone marrow cells of the male house mouse (Mus musculus L.)].
Coffee aroma--statistical analysis of compositional data.
Syntheses, structures, and photoluminescence of a series of silver(I) sulfonates with pyrazine derivatives.
Alkyldimethylpyrazines in the defensive spray of Phyllium westwoodii: a first for order Phasmatodea.
Identification of chemicals emitted by calling males of the Sapote fruit fly, Anastrepha serpentina.
Strong through-space two-halide magnetic exchange of -234 K in (2,5-dimethylpyrazine)copper(II) bromide.
A binuclear Cu(II) metallacycle capable of discerning between pyrazine and its different methyl-substituted derivatives based on reversible intracage metal-ligand binding.
2,5-Dimethyl-pyrazine 1,4-dioxide.
Formation of pyrazines and a novel pyrrole in Maillard model systems of 1,3-dihydroxyacetone and 2-oxopropanal.
[Effect of the estrous cycle stage on sensitivity to pheromone 2,5-dimethylpyrazine in the house mouse Mus musculus].
Competition between photochemistry and energy transfer in UV-excited diazabenzenes. 4. UV photodissociation of 2,3-, 2,5-, and 2,6-dimethylpyrazine.
[Chromosomal abnormalities and spleenocyte production in laboratory mouse males after exposure to stress chemosignals].
Structural study of silver(I) sulfonate complexes with pyrazine derivatives.
Mice respond differently to urine and its major volatile constituents from male and female ferrets.
Solitary foraging in the ancestral South American ant, Pogonomyrmex vermiculatus. Is it due to constraints in the production or perception of trail pheromones?
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.
Magnetic study on a two-dimensional coordination polymer with mixed bridging ligands.
Attenuation of the production of inositol 1,4,5-trisphosphate in the mouse vomeronasal organ by antibodies against the alphaq/11 subfamily of G-proteins.
Synthesis, a case of isostructural packing, and antimicrobial activity of silver(I)quinoxaline nitrate, silver(I)(2,5-dimethylpyrazine) nitrate and two related silver aminopyridine compounds.
[Induction of meiotic disturbances in spermatocytes I by pheromones as an inhibiting mechanism of male reproductive function in house mice].
Influence of steric hindrance of organic ligand on the structure of Keggin-based coordination polymer.
Role of the solvent glycerol in the Maillard reaction of d-fructose and l-alanine.
Tuning the electronic communication and rates of intramolecular electron transfer of dimers of trinuclear ruthenium clusters: bridging and ancillary ligand effects.
Putative chemosignals of the ferret (Mustela furo) associated with individual and gender recognition.
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.
Effects of water content on volatile generation and peptide degradation in the maillard reaction of glycine, diglycine, and triglycine.
Reactivity of epicatechin in aqueous glycine and glucose maillard reaction models: quenching of C2, C3, and C4 sugar fragments.
Identification of major histocompatibility complex-regulated body odorants by statistical analysis of a comparative gas chromatography/mass spectrometry experiment.
Synthesis, crystal structures, and magnetism of cobalt coordination polymers based on dicyanamide and pyrazine-dioxide derivatives.
Sex-specific responses to urinary chemicals by the mouse vomeronasal organ.
Aroma compounds in sweet whey powder.
Volatiles production and attractiveness to the Mexican fruit fly of Enterobacter agglomerans isolated from apple maggot and Mexican fruit flies.
Primer effects by conspecific odors in house mice: a new perspective in the study of primer effects on reproductive activities.
Pyrazine derivatives in cigarette smoke inhibit hamster oviductal functioning.
Odors detected by mice deficient in cyclic nucleotide-gated channel subunit A2 stimulate the main olfactory system.
[Chemical profiles of methylpyrazines contained in commercially available natto].
[Induction of dominant lethals in progeny of male CBA mice after pheromonal action].
Effect of 2,5-dimethylpyrazine on uterine contraction in late stage of pregnant female rats.
[The female pheromone 2,5-dimethylpyrazine induces sperm head abnormalities in male CBA mice].
Purine metabolizing capability of Enterobacter agglomerans affects volatiles production and attractiveness to Mexican fruit fly.
[Olfactory stress and modification of phagocytosis in peripheral blood cells of adult male mice].
catena-poly[[(acetonitrile-N)dichlorocopper(II)]-mu-2,5-dimethylpyrazine-kappa2N:N'].
Effect of alkylpyrazine derivatives on the duration of pentobarbital-induced sleep, picrotoxicin-induced convulsion and gamma-aminobutyric acid (GABA) levels in the mouse brain.
1-octen-3-ol isolated from bont ticks attracts Amblyomma variegatum.
Syntheses, structures, and physicochemical properties of diruthenium compounds of tetrachlorocatecholate with metal-metal bonded Ru(3+)(mu-OR)(2)Ru(3+) and Ru(3.5+)(mu-OR)(2)Ru(3.5+) cores (R = CH(3) and C(2)H(5)).
Recruitment pheromone in the harvester ant genus Pogonomyrmex.
[Genotype-specific changes of certain functional indicators of immunocompetent cells in male laboratory mice under conditions of pheromone stress].
Volatile flavor components of rice cakes.
Pyrazine formation from serine and threonine.
Effects of roasting on pyrazine contents and oxidative stability of red pepper seed oil prior to its extraction.
Oxidative DNA damage induced by aminoacetone, an amino acid metabolite.
Role of the adrenal gland and adrenal-mediated chemosignals in suppression of estrus in the house mouse: the lee-boot effect revisited.
Inhibitory effect of 2,5-dimethylpyrazine on oxytocic agent-induced uterine hypercontraction of normal or pregnant female rats.
[Physiological and pharmacological activities of simple alkyl- and arylpyrazines].
Rational Design of a Novel Intercalation System. Layer-Gap Control of Crystalline Coordination Polymers, {[Cu(CA)(H(2)O)(m)()](G)}(n)() (m = 2, G = 2,5-Dimethylpyrazine and Phenazine; m = 1, G = 1,2,3,4,6,7,8,9-Octahydrophenazine).
Attractants fromStaphylococcus aureus cultures for Mexican fruit fly,Anastrepha ludens.
Effects of 2,5-dimethylpyrazine on plasma testosterone and polyamines- and acid phosphatase-levels in the rat prostate.
Inhibition of sexual maturation in juvenile female and male mice by a chemosignal of female origin.
Long-term effect of a urinary chemosignal on reproductive fitness in female mice.
Effects of dimethylpyrazine isomers on reproductive and accessory reproductive organs in male rats.
Contents of poison apparatus and their relation to trail-following in the antDaceton armigerum.
Effects of 2,5-dimethylpyrazine on reproductive and accessory reproductive organs in female rats.
Chemotaxonomic study of undescribed species ofMyrmica ant from Idaho.
Interactions of heterocyclic Maillard products with the hepatic microsomal monooxygenase system.
Dynamics of excretion of urinary chemosignals in the house mouse (Mus musculus) during the natural estrous cycle.
Adrenal-mediated endogenous metabolites inhibit puberty in female mice.
Synthesis and antimetastatic properties of stereoisomeric tricyclic bis(dioxopiperazines) in the Lewis lung carcinoma model.
Identification of trail pheromone of the antTetramorium caespitum L. (Hymenoptera: Myrmicinae).
Identification of 2,5-dimethyl-pyrazine in the volatile flavour compounds of potato chips.
Publications by J-Stage
Chemical Profiles of Methylpyrazines Contained in Commercially Available Natto
Effect of 2,5-Dimethylpyrazine on Uterine Contraction in Late Stage of Pregnant Female Rats
Effect of Alkylpyrazine Derivatives on the Duration of Pentobarbital-Induced Sleep, Picrotoxicin-Induced Convulsion and ?-Aminobutyric Acid (GABA) Levels in the Mouse Brain

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
CHEMBL:View
HMDB (The Human Metabolome Database):HMDB35289
FooDB:FDB013954
YMDB (Yeast Metabolome Database):YMDB01598
Export Tariff Code:2933.99.8290
Typical G.C.
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View

Suppliers

Advanced Biotech Ambles Nature et Chimie
Anhui Haibei Augustus Oils
Beijing Lys Chemicals BOC Sciences
Charkit Chemical CJ Latta & Associates
DeLong Chemicals America Diffusions Aromatiques
EMD Millipore Endeavour Specialty Chemicals
Ernesto Ventós Excellentia International
FCI SAS Fleurchem
Frutarom IFF
Indukern F&F Jiangyin Healthway
Jinan Enlighten Chemical Technology(Wutong Aroma ) Kingchem Laboratories
Lluch Essence M&U International
Moellhausen Myrazine
OQEMA Pearlchem Corporation
Pell Wall Perfumes Penta International
Phoenix Aromas & Essential Oils R C Treatt & Co Ltd
Reincke & Fichtner Riverside Aromatics
Robinson Brothers Santa Cruz Biotechnology
Sigma-Aldrich Sunaux International
Synerzine Taytonn ASCC
TCI AMERICA Tengzhou Jitian Aroma Chemiclal
Tengzhou Xiang Yuan Aroma Chemicals Tianjin Danjun International
United International Vigon International
WholeChem Advanced Biotech. Inc.
Augustus Oils Ltd Beijing Lys Chemicals Co, LTD.
Charkit Chemical Corporation CJ Latta & Associates, LLC
Endeavour Specialty Chemicals Ltd Fleurchem, Inc.
FRUTAROM USA INC, Indukern, S.A. F&F Ingredients Division
Jiangyin Healthway International Trade Co., Ltd Lluch Essence S.L.
M&U International LLC Moellhausen S.P.A.
Myrazine LLC Penta International Corporation
Riverside Aromatics Ltd. Robinson Brothers Limited
Synerzine, Inc. Taytonn ASCC Pte Ltd
Tianjin Danjun International Trade Co., LTD. R C Treatt and Co Ltd
Qingdao Free Trade Zone United International Co Ltd Ernesto Ventós S.A.
WholeChem, LLC

PhysChem Properties

Material listed in food chemical codex Yes
Molecular weight 108.14376068115
Specific gravity @ 25 °C
Pounds per Gallon 8.155 to 8.321
Refractive Index 1.497 to 1.501 @ 20 °C
Boiling Point 154 to 156°C @ 760 mm Hg
Vapor Pressure 3.98 mmHg @ 25 °C
Vapor Density 3.7
Flash Point TCC Value 54.44 °C TCC
logP (o/w) 0.63
Solubility
alcohol Yes
water, 3.197e+004 mg/L @ 25 °C (est) Yes
water No

Organoleptic Properties

Odor Type: Chocolate
cocoa, roasted, nutty, beefy roasted beefy, woody, grassy, medicinal, peanut, musty, earthy, powdery
General comment At 0.10 % in dipropylene glycol. cocoa roasted nuts roast beef woody grass medical
Mosciano, Gerard P&F 21, No. 6, 49, (1996) Nutty, peanut, musty, earthy, powdery and slightly roasted with a cocoa powder nuance
Flavor Type: Musty
musty, potato, cocoa, nutty, fatty, oily
Mosciano, Gerard P&F 21, No. 6, 49, (1996) At 7.50 ppm. Musty, potato, cocoa and nutty with a fatty and oily nuance
Used in potato, beer and chicken flavors as well as those needing fried notes. Cocoa

Occurrences

Potential Uses

Applications
Odor purposes Chocolate, Coffee, Green, Hazelnut, Peanut
Flavoring purposes Chocolate cocoa, Potato, Roasted
Other purposes Fried
Cosmetic purposes Perfuming agents

Safety Information

Safety information

Preferred SDS: View
European information :
Most important hazard(s):
Xn - Harmful.
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 02 - Keep out of the reach of children.
S 24/25 - Avoid contact with skin and eyes.
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 1020 mg/kg
(Moran et al., 1980)

intraperitoneal-mouse LD50 1350 mg/kg
Toxicology and Applied Pharmacology. Vol. 17, Pg. 244, 1970.

oral-rat LD50 1020 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 2,5-dimethyl pyrazine usage levels up to:
0.1000 % in the fragrance concentrate.
Maximised Survey-derived Daily Intakes (MSDI-EU): 19.00 (μg/capita/day)
Maximised Survey-derived Daily Intakes (MSDI-USA): 8.00 (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
Click here to view publication 5
average usual ppmaverage maximum ppm
baked goods: -10.00000
beverages(nonalcoholic): -10.00000
beverages(alcoholic): --
breakfast cereal: -10.00000
cheese: --
chewing gum: --
condiments / relishes: --
confectionery froastings: --
egg products: --
fats / oils: --
fish products: --
frozen dairy: -10.00000
fruit ices: -10.00000
gelatins / puddings: -10.00000
granulated sugar: --
gravies: -10.00000
hard candy: -10.00000
imitation dairy: --
instant coffee / tea: --
jams / jellies: --
meat products: -10.00000
milk products: -10.00000
nut products: --
other grains: --
poultry: --
processed fruits: --
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: --
snack foods: --
soft candy: --
soups: -10.00000
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):123-32-0
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :31252
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
2,5-dimethylpyrazine
Chemidplus:0000123320
RTECS:UQ2800000 for cas# 123-32-0