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2,3-dimethyl pyrazine
2,3-dimethyl pyrazine is a pyrazine derivative with a nutty, roasted aroma used in food and fragrance applications for its characteristic cocoa and coffee notes.
General Material Description
2,3-dimethyl pyrazine is a low molecular weight heterocyclic aromatic compound characterized by a pyrazine ring substituted with two methyl groups at positions 2 and 3. It appears as a clear to pale-yellow liquid and is known for its pronounced nutty, roasted, and cocoa-like odor and flavor qualities. Referred to also as dimethyl-2,3 pyrazine or pyrazine, 2,3-dimethyl-, this compound is widely recognized in flavor chemistry and is classified under the PubChem entry CID 22201. It naturally occurs in various roasted and fermented foods and is used as a flavor and fragrance agent derived either from natural extraction or synthetic routes. The compound’s sensory properties have made it valuable in contributing to complex flavor profiles in food products and perfumes.
Occurrence, Applicability & Potential Uses
2,3-dimethyl pyrazine is found naturally in a range of edible and aromatic sources, including roasted barley, coffee, cocoa, Swiss cheese, black and green teas, roasted nuts such as filbert and pecan, and vegetables like cabbage and bell pepper. It contributes significantly to the aroma and taste of these foods, imparting nutty, roasted, and cocoa-like characteristics. This compound is used primarily as a flavor and fragrance agent in the food and perfume industries, enhancing products such as baked goods, meat, soups, beverages, and confectionery. Regulatory assessments under FEMA (US) categorize it as generally recognized as safe (GRAS) for flavoring use. It is included in industry standards such as IFRA (Global), which provides guidelines on usage levels in fragrances to ensure safety and consumer acceptability.
Physico-Chemical Properties Summary
2,3-dimethyl pyrazine (C6H8N2, molecular weight approximately 108.14 g/mol) exhibits moderate volatility with a vapor pressure near 3.45 mmHg at 25°C and a boiling range between 155°C and 157°C at standard atmospheric pressure. Its flash point is around 53°C (128°F), indicating flammability precautions are necessary in handling. The compound is soluble in alcohol, ether, and water, the estimated aqueous solubility being about 38 mg/L at 25°C. Specific gravity values range from 0.997 to about 1.03 at 25°C, and refractive index measurements lie between 1.50 and 1.51 at 20°C. The logP value of 0.54 reflects moderate lipophilicity, influencing its partitioning behavior in formulations. Chemically stable and non-discoloring under most conditions, 2,3-dimethyl pyrazine suits use in both aqueous and non-aqueous flavor and fragrance compositions.
FAQ
What is 2,3-dimethyl pyrazine and where is it found naturally?
2,3-dimethyl pyrazine is an aromatic compound belonging to the pyrazine class, known for contributing nutty and roasted aroma notes. It naturally occurs in various roasted and fermented foods such as roasted barley, coffee, cocoa, Swiss cheese, black and green teas, roasted nuts including filbert and pecan, as well as vegetables like cabbage and bell pepper. Its natural presence is integral to the characteristic flavors of these foods.
How is 2,3-dimethyl pyrazine used in food and fragrance applications?
This compound is utilized primarily as a flavor and fragrance agent to impart nutty, roasted, cocoa, and coffee-like notes. In food, it enhances products including baked goods, meat, soups, beverages, and dairy. In fragrance formulations, it adds complexity and warmth to scent profiles. Usage levels are controlled to maintain sensory balance and safety, with recommended maximum concentrations established by regulatory bodies.
What are the regulatory guidelines and safety considerations for 2,3-dimethyl pyrazine?
2,3-dimethyl pyrazine is evaluated by organizations such as FEMA (US) and IFRA (Global) and is recognized as safe for flavor use within specified limits. The compound has a moderate flash point and is classified as flammable, requiring appropriate handling precautions. Toxicological data indicate caution is needed to avoid ingestion beyond established safe levels. Safety data sheets provide detailed hazard information, and standard regulatory opinions confirm its suitability for food and fragrance applications under controlled conditions.
US / EU / FDA / JECFA / FEMA / Scholar / Patents
| Google Scholar | Start search |
| Google Books | Start search |
| Google Patents | Start search |
| Perfumer & Flavorists | Start search |
| EU Patents | Start search |
| PubMeb | Start search |
| NCBI | Start search |
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 |
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 |
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 |
|
Suppliers
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
| (data available) |
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 ppm | average maximum ppm | ||
| baked goods: | 10.00000 | 10.00000 | |
| beverages(nonalcoholic): | 10.00000 | 10.00000 | |
| beverages(alcoholic): | 0.00200 | 2.00000 | |
| breakfast cereal: | 0.10000 | 1.00000 | |
| cheese: | 0.10000 | 1.00000 | |
| chewing gum: | 1.00000 | 1.00000 | |
| condiments / relishes: | 0.10000 | 1.00000 | |
| confectionery froastings: | 0.10000 | 1.00000 | |
| egg products: | 0.10000 | 1.00000 | |
| fats / oils: | 0.10000 | 1.00000 | |
| fish products: | 0.10000 | 1.00000 | |
| frozen dairy: | 10.00000 | 10.00000 | |
| fruit ices: | - | - | |
| gelatins / puddings: | 10.00000 | 10.00000 | |
| granulated sugar: | 0.10000 | 1.00000 | |
| gravies: | 10.00000 | 10.00000 | |
| hard candy: | 10.00000 | 10.00000 | |
| imitation dairy: | 0.10000 | 1.00000 | |
| instant coffee / tea: | 0.10000 | 1.00000 | |
| jams / jellies: | 0.10000 | 1.00000 | |
| meat products: | 10.00000 | 10.00000 | |
| milk products: | 0.10000 | 1.00000 | |
| nut products: | - | - | |
| other grains: | 0.10000 | 1.00000 | |
| poultry: | 0.10000 | 1.00000 | |
| processed fruits: | - | - | |
| processed vegetables: | - | - | |
| reconstituted vegetables: | - | - | |
| seasonings / flavors: | 1.00000 | 10.00000 | |
| snack foods: | 0.10000 | 1.00000 | |
| soft candy: | 10.00000 | 10.00000 | |
| soups: | 0.10000 | 1.00000 | |
| sugar substitutes: | 0.10000 | 1.00000 | |
| sweet sauces: | 0.10000 | 1.00000 | |
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 |