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2-ethyl-3-methoxypyrazine
2-ethyl-3-methoxypyrazine is a pyrazine derivative recognized for its strong earthy and nutty aroma, commonly used in flavor and fragrance applications.
General Material Description
2-ethyl-3-methoxypyrazine is a heterocyclic aromatic organic compound characterized by a molecular formula of C7H10N2O. This compound exhibits a distinctive earthy and nutty odor reminiscent of raw potato, damp soil, and bell pepper. Synonyms used across literature and industry include earthy pyrazine, 2-methoxy-3-ethylpyrazine, and 3-ethyl-2-methoxypyrazine. It belongs to the chemical class of pyrazines, known for their potent aromas even at trace levels. The compound is listed in PubChem and is primarily sourced through chemical synthesis for use in flavor and fragrance formulations due to its robust sensory profile.
Occurrence, Applicability & Potential Uses
2-ethyl-3-methoxypyrazine naturally occurs in various plants and foods, notably in grapes, potatoes, and wines, contributing to their characteristic aromas. Its presence influences the sensory quality of these products, often adding earthy and green notes. Industrially, the compound is utilized as a flavor and fragrance agent to replicate or enhance nutty, pepper, and earthy scents and tastes. It plays a role in coffee and chocolate aroma characterizations, offering depth and diffusion when combined with other scent compounds. The compound's use is regulated under standards such as IFRA (Global), which limits its concentration to 0.0200% in fragrance concentrates to ensure safety and quality.
Physico-Chemical Properties Summary
2-ethyl-3-methoxypyrazine exhibits a molecular weight of 138.17 g/mol and a chemical structure that supports strong aromatic properties. It has a specific gravity of about 1.049 at 25 °C, indicating a density slightly higher than water. Its boiling point ranges from 80 to 95 °C at reduced pressure (10 mm Hg), demonstrating moderate volatility, with a vapor pressure of 1.577 mmHg at 25 °C contributing to its pronounced scent profile. The compound is soluble in alcohol and shows limited solubility in water, estimated at 2474 mg/L at 25 °C. A flash point of 156 °F (approximately 69 °C) suggests moderate flammability. These physicochemical properties influence its handling, formulation, and stability within flavor and fragrance applications.
FAQ
What is 2-ethyl-3-methoxypyrazine and what are its main characteristics?
2-ethyl-3-methoxypyrazine is an aromatic heterocyclic compound belonging to the pyrazine class. It is known for its potent earthy, nutty aroma often described as reminiscent of raw potato or bell pepper. The compound appears as a dense liquid with a molecular formula of C7H10N2O and is widely recognized for its strong odor even at very low concentrations. It is primarily used in flavor and fragrance industries to impart natural earthy and nutty notes.
Where does 2-ethyl-3-methoxypyrazine naturally occur and how is it applied industrially?
This compound naturally occurs in foods such as grapes, potatoes, and wines, where it contributes to characteristic earthy and green aromas. Industrially, 2-ethyl-3-methoxypyrazine is synthesized and employed as a flavor and fragrance agent to enhance or replicate sensory qualities in products. It is valued for its ability to add depth to coffee, chocolate, and nutty aroma profiles. Its usage is carefully controlled due to its high potency.
What regulations and safety considerations apply to 2-ethyl-3-methoxypyrazine use?
Regulatory frameworks such as IFRA (Global) govern the safe use of 2-ethyl-3-methoxypyrazine within fragrance formulations, recommending maximum levels of 0.0200% to mitigate risks. Safety data classify it as harmful if swallowed and irritating to skin and respiratory systems, necessitating appropriate handling precautions to avoid exposure. The compound's safety and usage levels have also been evaluated by EFSA (European Food Safety Authority) for flavoring applications. Users should consult material safety data sheets for detailed guidance.
US / EU / FDA / JECFA / FEMA / Scholar / Patents
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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 |
| CHEMBL: | View |
| HMDB (The Human Metabolome Database): | HMDB40054 |
| FooDB: | FDB019741 |
| Export Tariff Code: | 2933.99.8090 |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
General Material Information
| Preferred name | 2-ethyl-3-methoxypyrazine |
| Trivial Name | 2-Ethyl-3-methoxypyrazine |
| Short Description | pyrazine, 2-methoxy-3-ethyl |
| Formula | C7 H10 N2 O |
| CAS Number | 25680-58-4 |
| Flavis Number | 14.112 |
| ECHA Number | 247-184-0 |
| FDA UNII | ZBM5LD0WE9 |
| Nikkaji Number | J208.493G |
| MDL | MFCD00006129 |
| COE Number | 11329 |
| NMR Predictor | External link |
| Synonyms |
|
Suppliers
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 138.16990661621 |
| Specific gravity | @ 25 °C |
| Pounds per Gallon | |
| Boiling Point | 80 to 95°C @ 10 mm Hg |
| Vapor Pressure | 1.577 mmHg @ 25 °C |
| Flash Point TCC Value | 68.89 °C TCC |
| logP (o/w) | 1.8 |
| Solubility | |
| alcohol | Yes |
| water, 2474 mg/L @ 25 °C (est) | Yes |
| water | No |
Organoleptic Properties
| Odor Type: Earthy | |
| potato raw potato, earthy, green, pepper bell pepper, nutty | |
| General comment | At 0.10 % in dipropylene glycol. raw potato earthy bell pepper nutty |
| As with all pyrazines this is used in tiny traces Earthy Pyrazine at 0.1% in IPM smells rather like raw potato or freshly dug soil, but this material is also present in the scent of coffee and chocolate so it’s more versatile than might at first be thought. Even at this dilution this is a very strong scent that combines well with Geosmin, Terranol and similar materials to give a wet effect. Also with nutty, chocolatey and, perhaps surprisingly with green notes, to give warmth, depth and diffusion. | Raw-potato, damp-soil, musty, natural, nutty, roasted |
Occurrences
| (data available) |
Potential Uses
| Applications | |
| Odor purposes | Coffee , Earth |
| Flavoring purposes | Nut , Pepper bell pepper , Potato |
Safety Information
Safety information
| Preferred SDS: View | |
| European information : | |
| Most important hazard(s): | |
| Xn - Harmful. | |
| R 22 - Harmful if swallowed. R 37/38 - Irritating to respiratory system and skin. S 02 - Keep out of the reach of children. S 20/21 - When using do not eat, drink or smoke. S 23 - Do not breath vapour. 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 39 - Wear 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 2-ethyl-3-methoxypyrazine usage levels up to: | |||
| 0.0200 % in the fragrance concentrate. | |||
| Maximised Survey-derived Daily Intakes (MSDI-EU): | 0.17 (μg/capita/day) | ||
| Threshold of Concern: | 90 (μg/person/day) | ||
| Structure Class: | III | ||
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): |
| Scientific Opinion on Flavouring Group Evaluation 17, Revision 3 (FGE.17Rev3): Pyrazine derivatives from chemical group 24 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):25680-58-4 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :33135 |
| National Institute of Allergy and Infectious Diseases:Data |
| WGK Germany:3 |
| 2-ethyl-3-methoxypyrazine |
| Chemidplus:0025680584 |