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hazelnut pyrazine
Hazelnut pyrazine (2,3-diethyl-5-methylpyrazine) is a flavor and fragrance compound known for musty, nutty, roasted hazelnut aroma and taste.
General Material Description
Hazelnut pyrazine, chemically known as 2,3-diethyl-5-methylpyrazine, is an aromatic heterocyclic compound with the molecular formula C9H14N2. It belongs to the pyrazine chemical class characterized by a six-membered ring containing two nitrogen atoms opposite each other. This compound exhibits a distinctive musty and nutty aroma evocative of roasted hazelnuts and toasted potato, which makes it valuable in flavor and fragrance formulations. Also recognized by synonyms such as methyl terrazome and 2-methyl-5,6-diethylpyrazine, it is referenced in the PubChem database. It is typically derived synthetically for use in flavorings, replicating the sensory qualities found naturally in foods like roasted nuts and coffee.
Occurrence, Applicability & Potential Uses
Hazelnut pyrazine naturally occurs in various cooked and roasted foods including beef, cheese varieties such as Parmesan and Provolone, roasted hazelnut and peanut, coffee, cocoa, chicken, lamb, pork, and roasted sesame seeds. Due to its potent musty, nutty odor and flavor characteristics, it finds application as a flavoring and fragrance agent enhancing products with nutty, roasted, or earthy profiles. Its use is regulated under FEMA (US) standards and the IFRA (Global) Code of Practice, which set recommended usage limits to ensure safety in consumer products. The compound contributes to flavor notes in cheese, chocolate, nut-flavored formulations, pork, potato, tomato, and vegetable products, while also enhancing coffee and popcorn aromas in fragrance applications.
Physico-Chemical Properties Summary
Hazelnut pyrazine possesses a molecular weight of approximately 150.22 g/mol and formula C9H14N2. It has a boiling range near 191-193°C at atmospheric pressure and a vapor pressure of approximately 0.515 mmHg at 25°C, reflecting moderate volatility which influences aroma release in formulations. The compound’s specific gravity ranges between 0.938 and 0.957 g/cm³ at 20-25°C with a refractive index of about 1.495 to 1.498 at 20°C. Its flash point is estimated at 176°F (approximately 80°C), indicating a moderate flammability hazard. With a log P of 1.95, it shows moderate lipophilicity, enhancing solubility in alcohol and limited solubility in water (around 1636 mg/L at 25°C). These properties affect its behavior in flavor and fragrance matrices, contributing to its persistence and substantivity.
FAQ
What is hazelnut pyrazine and what are its sensory characteristics?
Hazelnut pyrazine, also known as 2,3-diethyl-5-methylpyrazine, is a pyrazine derivative compound used primarily in flavors and fragrances. It is recognized for its strong musty, nutty, and roasted hazelnut aroma, often described as earthy with notes reminiscent of toasted potato and cocoa. These sensory qualities make it valuable for replicating roasted nut flavors in various food products and for enhancing nutty notes in perfumery.
In which foods and applications is hazelnut pyrazine commonly found or used?
This compound naturally occurs in a range of roasted and cooked foods including hazelnuts, peanuts, beef, chicken, lamb, pork, Parmesan and Provolone cheeses, coffee, cocoa, sesame seeds, and potato products such as chips and french fries. It is used as a flavor and fragrance agent to impart nutty, roasted, and earthy notes in foodstuffs like chocolate, cheese, and savory snacks, as well as in fragrance blends mimicking coffee and popcorn aromas.
What are the safety considerations and regulatory standards for using hazelnut pyrazine?
Hazelnut pyrazine is classified as an irritant under European regulations, requiring appropriate handling to avoid eye, skin, and respiratory irritation. It is assessed by bodies such as FEMA (US), IFRA (Global), and EFSA (EU), which recommend maximum usage levels to ensure consumer safety. For example, its use in fragrance concentrates is limited to 0.0800%, and flavor usage levels are monitored to avoid excessive intake. Safety data indicate no significant oral or inhalation toxicity determined, but protective measures are advised during handling.
US / EU / FDA / JECFA / FEMA / Scholar / Patents
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| Perfumer & Flavorists | Start search |
| EU Patents | Start search |
| PubMeb | Start search |
| NCBI | Start search |
Literature & References
| 2,3-diethyl-5-methylpyrazine | |
| NIST Chemistry WebBook: | Search Inchi |
| Canada Domestic Sub. List: | 18138-04-0 |
| Pubchem (cid): | 28905 |
| Pubchem (sid): | 134993059 |
| Flavornet: | 18138-04-0 |
| 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 |
| CHEMBL: | View |
| HMDB (The Human Metabolome Database): | HMDB41345 |
| FooDB: | FDB021268 |
| Export Tariff Code: | 2933.99.9701 |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
General Material Information
| Preferred name | hazelnut pyrazine |
| Trivial Name | 2,3-Diethyl-5-methylpyrazine |
| Short Description | 2,3-diethyl-5-methylpyrazine |
| Formula | C9 H14 N2 |
| CAS Number | 18138-04-0 |
| FEMA Number | 3336 |
| Flavis Number | 14.056 |
| ECHA Number | 242-024-6 |
| FDA UNII | 530763R0AP |
| Nikkaji Number | J99.991A |
| MDL | MFCD00009635 |
| COE Number | 11303 |
| Bio Activity Summary | External link |
| NMR Predictor | External link |
| JECFA Food Flavoring | 777 2,3-diethyl-5-methylpyrazine |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm | 18138-04-0 ; 2,3-DIETHYL-5-METHYLPYRAZINE |
| Synonyms |
|
Suppliers
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 150.22457885742 |
| Specific gravity | @ 20 °C |
| Pounds per Gallon | 7.898 to 7.931 |
| Specific gravity | @ 25 °C |
| Pounds per Gallon | 7.805 to 7.963 |
| Refractive Index | 1.495 to 1.498 @ 20 °C |
| Boiling Point | 191 to 193°C @ 760 mm Hg |
| Vapor Pressure | 0.515 mmHg @ 25 °C |
| Vapor Density | 5.2 |
| Flash Point TCC Value | 80 °C TCC |
| logP (o/w) | 1.95 |
| Solubility | |
| alcohol | Yes |
| water, 1636 mg/L @ 25 °C (est) | Yes |
Organoleptic Properties
| Odor Type: Musty | |
| musty, nut skin, earthy, hazelnut roasted hazelnut, toasted, potato, dusty, foliage, vegetable, green, meaty | |
| Odor strength | high , recommend smelling in a 0.10 % solution or less |
| Substantivity | 4 hour(s) at 100.00 % |
| Luebke, William tgsc, (2021) | At 0.10 % in dipropylene glycol. musty nut skin earthy roasted hazelnut toasted potato dusty foliage vegetable |
| Mosciano, Gerard P&F 21, No. 5, 49, (1996) | Musty, nut skin, earthy, toasted, potato bin, green and meaty |
| Flavor Type: Musty | |
| musty, nutty, toasted, cocoa, hazelnut, potato, potato chip, earthy, dirty | |
| Luebke, William tgsc, (2021) | Musty nutty toasted cocoa hazelnut potato potato chip earthy dirty |
| Mosciano, Gerard P&F 21, No. 5, 49, (1996) | At 2.50 ppm. Musty, toasted, nutty, potato, cocoa, earthy and dirty |
| Used in chocolate, roast nut, bread and coffee flavours, at 0.01-1ppm. | Chocolate |
Occurrences
| (data available) |
Potential Uses
| Applications | |
| Odor purposes | Coffee , Filbert , Hazelnut , Peanut , Popcorn |
| Flavoring purposes | Cheese , Chocolate cocoa , Nut , Pork , Potato , Tomato , Vegetable |
Safety Information
Safety information
| Preferred SDS: View | |
| European information : | |
| Most important hazard(s): | |
| Xi - Irritant | |
| R 36/37/38 - Irritating to eyes, respiratory system, and skin. 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: | |
| Not determined | |
| 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 hazelnut pyrazine usage levels up to: | |||
| 0.0800 % in the fragrance concentrate. | |||
| Maximised Survey-derived Daily Intakes (MSDI-EU): | 0.11 (μg/capita/day) | ||
| Maximised Survey-derived Daily Intakes (MSDI-USA): | 1.00 (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: 6 | |||
| Click here to view publication 6 | |||
| average usual ppm | average maximum ppm | ||
| baked goods: | - | 1.00000 | |
| beverages(nonalcoholic): | - | 0.10000 | |
| beverages(alcoholic): | - | - | |
| breakfast cereal: | - | 1.00000 | |
| cheese: | - | - | |
| chewing gum: | - | - | |
| condiments / relishes: | - | - | |
| confectionery froastings: | - | - | |
| egg products: | - | - | |
| fats / oils: | - | - | |
| fish products: | - | - | |
| frozen dairy: | - | 0.20000 | |
| fruit ices: | - | 0.20000 | |
| gelatins / puddings: | - | 0.20000 | |
| granulated sugar: | - | - | |
| gravies: | - | 0.20000 | |
| hard candy: | - | 0.50000 | |
| imitation dairy: | - | - | |
| instant coffee / tea: | - | - | |
| jams / jellies: | - | - | |
| meat products: | - | 0.20000 | |
| milk products: | - | - | |
| nut products: | - | - | |
| other grains: | - | - | |
| poultry: | - | - | |
| processed fruits: | - | - | |
| processed vegetables: | - | - | |
| reconstituted vegetables: | - | - | |
| seasonings / flavors: | - | - | |
| snack foods: | - | - | |
| soft candy: | - | - | |
| soups: | - | 0.20000 | |
| 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 |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA Substance Registry Services (TSCA):18138-04-0 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :28905 |
| National Institute of Allergy and Infectious Diseases:Data |
| WGK Germany:3 |
| 2,3-diethyl-5-methylpyrazine |
| Chemidplus:0018138040 |