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2,5-diethyl-3-methyl pyrazine
2,5-diethyl-3-methylpyrazine is a pyrazine derivative with a nutty aroma, used as a flavoring agent in foods like coffee, bacon, and nuts.
General Material Description
2,5-diethyl-3-methylpyrazine is an aromatic heterocyclic organic compound classified within the pyrazine derivatives. It appears as a colorless to pale liquid and is characterized by a distinct nutty, toasted hazelnut scent with meaty nuances. The compound is known under several synonyms, including 3,6-diethyl-2-methylpyrazine and 2,5-diethyl-3-methyl-1,4-diazine. It has the molecular formula C9H14N2 and is featured in the PubChem database. This pyrazine is typically sourced from natural food processes such as roasting or frying, occurring naturally in foods like coffee, bacon, and nuts. Additionally, it can be synthetically produced for use as a flavoring agent in the food industry.
Occurrence, Applicability & Potential Uses
2,5-diethyl-3-methylpyrazine naturally occurs in roasted and fried food items including bacon and nuts such as filbert and macadamia, as well as in coffee and potatoes. Its nutty and slightly burnt aroma profile makes it valuable in flavoring applications, particularly for enhancing coffee and hazelnut flavors. This compound is recognized under FEMA (US) as FEMA number 3915 and is utilized primarily as a flavoring agent in various food categories. Its inclusion in formulations conforms with regulatory standards governing flavor additives to ensure controlled use and safety.
Physico-Chemical Properties Summary
This compound has a molecular weight of approximately 150.22 g/mol and exhibits moderate volatility, with a boiling point ranging between 206 and 207 °C at standard atmospheric pressure. It shows a flash point of 77 °C (170 °F, closed cup) indicating some flammability under specific conditions. At 25 °C, its specific gravity ranges from 0.944 to 0.954, and refractive index varies between 1.4922 and 1.5022 at 20 °C. The estimated octanol-water partition coefficient (log P) of about 1.966 suggests moderate lipophilicity, affecting its solubility and interaction in formulations. It is slightly soluble in water, with solubility around 488.9 mg/L at 25 °C, but fully soluble in alcohols, guiding its use in various food and flavor systems.
FAQ
What is 2,5-diethyl-3-methylpyrazine and what are its sensory characteristics?
2,5-diethyl-3-methylpyrazine is an organic compound belonging to the pyrazine class of chemicals. It possesses a distinctive nutty odor reminiscent of toasted hazelnut combined with subtle meaty and burnt notes. These sensory traits make it valuable as a flavoring agent in food products, contributing complexity and depth to aromas and tastes found in roasted and fried foods such as coffee, bacon, and certain nuts.
Where does 2,5-diethyl-3-methylpyrazine naturally occur, and how is it used in industry?
This compound naturally appears during cooking processes, particularly roasting, in foods like coffee beans, fried bacon, roasted filberts, macadamia nuts, and potatoes. Industrially, it is utilized as a flavor additive to impart nutty and roasted flavor notes, predominantly in coffee and hazelnut-flavored products. Its properties allow it to blend well in various food formulations consistent with flavor enhancement objectives.
What regulatory standards and safety considerations govern the use of 2,5-diethyl-3-methylpyrazine?
2,5-diethyl-3-methylpyrazine is evaluated by bodies such as FEMA (US), where it is identified as FEMA number 3915 and considered a generally recognized as safe (GRAS) flavoring substance for specified uses. It has been assessed by the European Food Safety Authority (EFSA) under Flavouring Group Evaluations related to pyrazine derivatives. Safety evaluations indicate no significant classification hazards under OSHA guidelines, and usage levels are regulated to minimize exposure. It is approved for flavoring use but not for fragrance applications, with maximum recommended concentrations established in food categories to ensure compliance.
US / EU / FDA / JECFA / FEMA / Scholar / Patents
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| EU Patents | Start search |
| PubMeb | Start search |
| NCBI | Start search |
Literature & References
| 2,5-diethyl-3-methylpyrazine | |
| NIST Chemistry WebBook: | Search Inchi |
| Pubchem (cid): | 36225 |
| Pubchem (sid): | 134999249 |
| Publications by US Patents | |
| 3,952,024 - Furfurylthioacetone | |
| Certain 2,5-dimethyl-3-thiopyrazines | |
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 |
| HMDB (The Human Metabolome Database): | HMDB36132 |
| FooDB: | FDB014981 |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
General Material Information
| Preferred name | 2,5-diethyl-3-methyl pyrazine |
| Trivial Name | 2,5-Diethyl-3-methylpyrazine |
| Short Description | 2,5-diethyl-3-methylpyrazine |
| Formula | C9 H14 N2 |
| CAS Number | 32736-91-7 |
| FEMA Number | 3915 |
| Flavis Number | 14.096 |
| FDA UNII | N079TRL8P5 |
| Nikkaji Number | J855.272J |
| COE Number | 11304 |
| NMR Predictor | External link |
| JECFA Food Flavoring | 778 2,5-diethyl-3-methylpyrazine |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm | 32736-91-7 ; 2,5-DIETHYL-3-METHYLPYRAZINE |
| Synonyms |
|
Suppliers
| Axsyn | BOC Sciences |
| Parchem |
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 150.22457885742 |
| Specific gravity | @ 25 °C |
| Pounds per Gallon | 7.855 to 7.938 |
| Refractive Index | 1.4922 to 1.5022 @ 20 °C |
| Boiling Point | 206 to 207°C @ 760 mm Hg |
| Vapor Pressure | 0.337 mmHg @ 25 °C |
| Flash Point TCC Value | 76.67 °C TCC |
| logP (o/w) | 1.966 est |
| Solubility | |
| alcohol | Yes |
| water, slightly | Yes |
| water, 488.9 mg/L @ 25 °C (est) | Yes |
| water | No |
Organoleptic Properties
| Odor Type: Nutty | |
| toasted, hazelnut, hazelnut roasted hazelnut, meaty | |
| General comment | At 0.10 % in dipropylene glycol. toasted hazelnut meaty |
| Flavor Type: Nutty | |
| hazelnut roasted hazelnut, hazelnut, burnt, nutty | |
| General comment | Hazelnut burnt |
Occurrences
| (data available) |
Safety Information
Safety information
| 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: | |
| Not determined | |
| Dermal Toxicity: | |
| Not determined | |
| Inhalation Toxicity: | |
| Not determined | |
Safety in use information
| Category: | |||
| flavoring agents | |||
| Recommendation for 2,5-diethyl-3-methyl pyrazine usage levels up to: | |||
| not for fragrance use. | |||
| Maximised Survey-derived Daily Intakes (MSDI-EU): | 0.012 (μg/capita/day) | ||
| Maximised Survey-derived Daily Intakes (MSDI-USA): | 0.01 (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: 19 | |||
| Click here to view publication 19 | |||
| average usual ppm | average maximum ppm | ||
| baked goods: | 1.00000 | 2.00000 | |
| beverages(nonalcoholic): | 0.50000 | 1.00000 | |
| beverages(alcoholic): | 0.10000 | 0.50000 | |
| breakfast cereal: | 1.00000 | 2.00000 | |
| cheese: | - | - | |
| chewing gum: | - | - | |
| condiments / relishes: | - | - | |
| confectionery froastings: | - | - | |
| egg products: | - | - | |
| fats / oils: | - | - | |
| fish products: | - | - | |
| frozen dairy: | 0.50000 | 1.00000 | |
| fruit ices: | - | - | |
| gelatins / puddings: | 0.50000 | 1.00000 | |
| granulated sugar: | - | - | |
| gravies: | - | - | |
| hard candy: | - | - | |
| imitation dairy: | - | - | |
| instant coffee / tea: | - | - | |
| jams / jellies: | - | - | |
| meat products: | 0.50000 | 1.00000 | |
| milk products: | - | - | |
| nut products: | - | - | |
| other grains: | - | - | |
| poultry: | - | - | |
| processed fruits: | - | - | |
| processed vegetables: | - | - | |
| reconstituted vegetables: | - | - | |
| seasonings / flavors: | - | - | |
| snack foods: | - | - | |
| soft candy: | 1.00000 | 2.00000 | |
| soups: | 0.10000 | 0.50000 | |
| 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 |
| EPI System: View |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :36225 |
| National Institute of Allergy and Infectious Diseases:Data |
| 2,5-diethyl-3-methylpyrazine |
| Chemidplus:0032736917 |