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2-acetyl-6-methyl pyrazine
2-acetyl-6-methyl pyrazine is a pyrazine compound emitting roasted aromas, utilized primarily as a flavoring agent in foods such as coffee and roasted seeds.
General Material Description
2-acetyl-6-methyl pyrazine is a heterocyclic aromatic organic compound classified among pyrazine derivatives. It appears as a low molecular weight chemical with molecular formula C7H8N2O and a molecular weight of approximately 136.15 g/mol. This compound emits a roasted aroma reminiscent of coffee, cocoa, and popcorn, contributing to characteristic sensory profiles in flavor formulations. Known synonyms encompass ethanone, 1-(6-methyl-2-pyrazinyl)- and related systematic names, ensuring cross-reference across chemical databases. Derived naturally or via synthesis, it is predominantly isolated from roasted foods where pyrazine compounds arise from Maillard reaction processes. More information can be found using the PubChem database entry. This flavor ingredient integrates into food formulations to impart roasted and nutty sensory nuances.
Occurrence, Applicability & Potential Uses
This compound is naturally present in roasted coffee beans, detected at concentrations up to 0.55 mg/kg, and also occurs in roasted sesame seeds. Within flavor chemistry, 2-acetyl-6-methyl pyrazine is valued for its ability to convey roasted, nutty, and cocoa-like olfactory characteristics. Its applications are primarily in the formulation of flavoring agents across diverse food categories, contributing complexity and enhancing sensory appeal. The compound's use and safety have been evaluated under the European Food Safety Authority's flavoring group evaluations, including FGE.17 and FGE.50, aligning with Commission Regulation (EC) No 1565/2000 (EU). These assessments facilitate its controlled application in foods while ensuring regulatory compliance.
Physico-Chemical Properties Summary
2-acetyl-6-methyl pyrazine displays a moderate volatility with boiling point values measured between 225 and 227°C at standard atmospheric pressure. Its vapor pressure at 25°C is approximately 0.069 mmHg, indicating limited but measurable volatility contributing to aroma perception. The compound exhibits moderate lipophilicity, with an estimated logP value around 0.45, affecting its partitioning in flavor matrices. It demonstrates solubility in alcohols and an estimated water solubility of about 62,410 mg/L at 25°C, supportive of its dispersion in aqueous-alcoholic media. The flash point is recorded at 204°F (approximately 95.6°C), reflecting typical ketone safety characteristics. These physicochemical traits shape its behavior during flavor formulation, stability, and release.
FAQ
What is 2-acetyl-6-methyl pyrazine and what sensory characteristics does it have?
2-acetyl-6-methyl pyrazine is an aromatic ketone within the pyrazine class of compounds. It contributes roasted, coffee-like aroma notes often associated with cocoa and popcorn sensory profiles. This compound is used primarily to impart these roasted and nutty flavor nuances in food and flavoring applications.
Where does 2-acetyl-6-methyl pyrazine naturally occur and how is it used in products?
This compound naturally occurs in roasted coffee beans at concentrations up to 0.55 mg/kg and is present in roasted sesame seeds. It is widely utilized as a flavoring agent in various food products, enhancing roasted and nutty aromas. Its use spans categories such as dairy products, confectionery, bakery wares, and beverages, where it enriches flavor complexity.
What regulatory evaluations and safety information are associated with 2-acetyl-6-methyl pyrazine?
2-acetyl-6-methyl pyrazine has been reviewed under European Food Safety Authority (EFSA) flavoring group evaluations, including FGE.17 and FGE.50, compliant with Commission Regulation (EC) No 1565/2000 (EU). Current hazard classifications under OSHA HCS show none, with no identified hazard or precautionary statements. Usage levels in food are defined with intake thresholds such as MSDI and mTAMDI to guide safe consumption. No significant toxicity data have been determined, and it is regulated as a flavor additive within established usage limits.
US / EU / FDA / JECFA / FEMA / Scholar / Patents
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Literature & References
| 1-(6-methylpyrazin-2-yl)ethanone | |
| NIST Chemistry WebBook: | Search Inchi |
| Pubchem (cid): | 527821 |
| Pubchem (sid): | 125682123 |
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 |
| HMDB (The Human Metabolome Database): | Search |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
General Material Information
| Preferred name | 2-acetyl-6-methyl pyrazine |
| Trivial Name | 2-Acetyl-6-methylpyrazine |
| Short Description | 1-(6-methylpyrazin-2-yl)ethanone |
| Formula | C7 H8 N2 O |
| CAS Number | 22047-26-3 |
| Flavis Number | 14.087 |
| FDA UNII | Search |
| Nikkaji Number | J624.962K |
| COE Number | 11298 |
| xLogP3-AA | 0.20 (est) |
| NMR Predictor | External link |
| Synonyms |
|
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 136.15396118164 |
| Boiling Point | 225 to 227°C @ 760 mm Hg |
| Vapor Pressure | 0.069 mmHg @ 25 °C |
| Flash Point TCC Value | 95.4 °C TCC |
| logP (o/w) | 0.447 est |
| Solubility | |
| alcohol | Yes |
| water, 6.241e+004 mg/L @ 25 °C (est) | Yes |
| water | No |
Organoleptic Properties
| Odor Type: Roasted | |
| roasted, coffee, cocoa, popcorn, coffee roasted coffee | |
| General comment | At 0.01 % in propylene glycol. roasted coffee cocoa popcorn |
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-acetyl-6-methyl pyrazine usage levels up to: | |||
| not for fragrance use. | |||
| Maximised Survey-derived Daily Intakes (MSDI-EU): | 0.028 (μg/capita/day) | ||
| Modified Theoretical Added Maximum Daily Intake (mTAMDI): | 270 (μg/person/day) | ||
| Threshold of Concern: | 540 (μg/person/day) | ||
| Structure Class: | II | ||
| Food categories according to Commission Regulation EC No. 1565/2000 (EC, 2000) in FGE.06 (EFSA, 2002a). According to the Industry the "normal" use is defined as the average of reported usages and "maximum use" is defined as the 95th percentile of reported usages (EFSA, 2002i). | |||
| Note: mg/kg = 0.001/1000 = 0.000001 = 1/1000000 = ppm. | |||
| average usage mg/kg | maximum usage mg/kg | ||
| Dairy products, excluding products of category 02.0 (01.0): | 0.40000 | 2.00000 | |
| Fats and oils, and fat emulsions (type water-in-oil) (02.0): | 0.10000 | 0.50000 | |
| Edible ices, including sherbet and sorbet (03.0): | 0.40000 | 2.00000 | |
| Processed fruit (04.1): | 0.40000 | 2.00000 | |
| Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2): | - | - | |
| Confectionery (05.0): | 1.00000 | 5.00000 | |
| Chewing gum (05.3): | - | - | |
| Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0): | 0.20000 | 1.00000 | |
| Bakery wares (07.0): | 1.00000 | 5.00000 | |
| Meat and meat products, including poultry and game (08.0): | 0.10000 | 0.40000 | |
| Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0): | 0.10000 | 0.40000 | |
| Eggs and egg products (10.0): | - | - | |
| Sweeteners, including honey (11.0): | - | - | |
| Salts, spices, soups, sauces, salads, protein products, etc. (12.0): | 0.10000 | 0.50000 | |
| Foodstuffs intended for particular nutritional uses (13.0): | 0.20000 | 1.00000 | |
| Non-alcoholic ("soft") beverages, excl. dairy products (14.1): | 0.20000 | 1.00000 | |
| Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2): | 1.00000 | 5.00000 | |
| Ready-to-eat savouries (15.0): | 1.00000 | 5.00000 | |
| Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0): | 0.20000 | 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 |
| Scientific Opinion on Flavouring Group Evaluation 17, Revision 3 (FGE.17Rev3): Pyrazine derivatives from chemical group 24 View page or View pdf |
| EPI System: View |
| AIDS Citations:Search |
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| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :527821 |
| National Institute of Allergy and Infectious Diseases:Data |
| 1-(6-methylpyrazin-2-yl)ethanone |