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2-isobutyl-3-methyl pyrazine
2-isobutyl-3-methyl pyrazine is a pyrazine compound known for caramellic and green odors, used mainly as a flavor and fragrance agent in foods like coffee and bacon.
General Material Description
2-isobutyl-3-methyl pyrazine is a heterocyclic compound characterized by a pyrazine ring substituted with isobutyl and methyl groups, with the molecular formula C9H14N2. It appears as a volatile chemical with distinctive caramellic and green herbaceous odor notes, which contribute to its value in flavor and fragrance formulations. Known under various synonyms such as 2-methyl-3-(2-methylpropyl)pyrazine, this compound is often referenced in flavor libraries and scientific databases including PubChem. It naturally occurs in various food products, including coffee and meat, and can be synthesized for use in flavoring and fragrance agents. Its sensory profile enhances green vegetable, tropical, bacon, and potato flavors.
Occurrence, Applicability & Potential Uses
2-isobutyl-3-methyl pyrazine occurs naturally in foods such as coffee, fried bacon, and various potato products, contributing to their characteristic aroma and flavor profiles. This pyrazine derivative is widely utilized as a flavor and fragrance agent to impart green, caramellic, bacon, meat, tropical, and potato nuances. It is frequently incorporated in the formulation of complex flavor blends and aromatic products. Regulatory evaluations, including those by FEMA (US), permit its use within defined concentration limits, reflecting its acceptance as a flavoring substance. Such standards provide guidance for safe application across food and fragrance industries.
Physico-Chemical Properties Summary
This compound exhibits a boiling point range between 199 and 201°C at standard atmospheric pressure, reflecting moderate volatility suitable for flavor applications. Its vapor pressure at 25°C is low (approximately 0.302 mmHg), which supports controlled release in formulations. The flash point is reported at 82°C (converted from 180°F), indicating a moderately flammable material under specific conditions. Solubility data show it dissolves in alcohol and has limited water solubility (approximately 1604 mg/L at 25°C), which influences its behavior in aqueous and nonaqueous systems. The logP value of 1.96 signifies moderate hydrophobicity, affecting partitioning in flavor matrices and product stability.
FAQ
What is 2-isobutyl-3-methyl pyrazine and what are its main sensory characteristics?
2-isobutyl-3-methyl pyrazine is a pyrazine-based aromatic compound widely used in flavor and fragrance applications. It is recognized for its caramellic odor with green, herbal notes, providing sensory contributions described as green vegetable or tropical in flavor contexts. Its structure consists of a pyrazine ring substituted with isobutyl and methyl groups, imparting distinct aroma characteristics that enhance food products like coffee, bacon, and potato items.
Where does 2-isobutyl-3-methyl pyrazine naturally occur and how is it applied in industry?
This compound naturally occurs in various cooked and roasted foods such as fried bacon, coffee, and processed potato products, often contributing to their characteristic aromas. Industrially, it is used as a flavoring agent and fragrance component to simulate or enhance meat, tropical, green, and caramellic flavor notes. Its applications include incorporation in food flavorings, fragrance formulations, and aroma blends aimed at providing sensory depth and complexity.
What are the regulatory considerations and safety information for 2-isobutyl-3-methyl pyrazine?
2-isobutyl-3-methyl pyrazine is recognized by regulatory bodies including FEMA (US) and is generally permitted for use as a flavoring substance within specified concentration limits, such as up to 0.5% in fragrance concentrates as recommended by IFRA (Global). Safety assessments have not identified significant hazard classifications under OSHA regulations. Comprehensive evaluations by agencies like JECFA and EFSA have examined its toxicological profile, supporting its controlled use in foods and fragrances. Safety data sheets indicate no notable GHS hazard classifications. Users should reference current regulatory guidelines and safety data for specific application contexts.
US / EU / FDA / JECFA / FEMA / Scholar / Patents
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Literature & References
| 2-methyl-3-(2-methylpropyl)pyrazine | |
| NIST Chemistry WebBook: | Search Inchi |
| Canada Domestic Sub. List: | 13925-06-9 |
| Pubchem (cid): | 26333 |
| Pubchem (sid): | 134990416 |
| 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): | HMDB36174 |
| FooDB: | FDB015028 |
| Export Tariff Code: | 2933.59.8000 |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
General Material Information
| Preferred name | 2-isobutyl-3-methyl pyrazine |
| Trivial Name | 2-Isobutyl-3-methylpyrazine |
| Short Description | 2-isobutyl-3-methylpyrazine |
| Formula | C9 H14 N2 |
| CAS Number | 13925-06-9 |
| FEMA Number | 3133 |
| Flavis Number | 14.044 |
| ECHA Number | 237-693-6 |
| FDA UNII | 11EP4V0M9Z |
| Nikkaji Number | J149.483J |
| MDL | MFCD00059770 |
| Bio Activity Summary | External link |
| NMR Predictor | External link |
| JECFA Food Flavoring | 773 2-isobutyl-3-methylpyrazine |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm | 13925-06-9 ; 2-ISOBUTYL-3-METHYLPYRAZINE |
| Synonyms |
|
Suppliers
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 150.22457885742 |
| Boiling Point | 199 to 201°C @ 760 mm Hg |
| Vapor Pressure | 0.302 mmHg @ 25 °C |
| Flash Point TCC Value | 82.22 °C TCC |
| logP (o/w) | 1.96 |
| Solubility | |
| alcohol | Yes |
| water, 1604 mg/L @ 25 °C (est) | Yes |
Organoleptic Properties
| Odor Type: Caramellic | |
| herbal, green, sugar | |
| General comment | At 0.10 % in dipropylene glycol. herbal green sugar syrup |
| Flavor Type: Green | |
| green, vegetable | |
| General comment | Green vegetable |
Occurrences
| (data available) |
Potential Uses
| Applications | |
| Odor purposes | Coffee , Green |
| Flavoring purposes | Bacon , Meat , Potato , Tropical |
Safety Information
Safety information
| Preferred SDS: View | |
| 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-isobutyl-3-methyl pyrazine usage levels up to: | |||
| 0.5000 % in the fragrance concentrate. | |||
| Maximised Survey-derived Daily Intakes (MSDI-EU): | 0.037 (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: 4 | |||
| Click here to view publication 4 | |||
| average usual ppm | average maximum ppm | ||
| baked goods: | - | 5.00000 | |
| beverages(nonalcoholic): | - | 5.00000 | |
| beverages(alcoholic): | - | - | |
| breakfast cereal: | - | - | |
| cheese: | - | - | |
| chewing gum: | - | - | |
| condiments / relishes: | - | - | |
| confectionery froastings: | - | - | |
| egg products: | - | - | |
| fats / oils: | - | - | |
| fish products: | - | - | |
| frozen dairy: | - | 5.00000 | |
| fruit ices: | - | 5.00000 | |
| gelatins / puddings: | - | 5.00000 | |
| granulated sugar: | - | - | |
| gravies: | - | - | |
| hard candy: | - | 5.00000 | |
| imitation dairy: | - | - | |
| instant coffee / tea: | - | - | |
| jams / jellies: | - | - | |
| meat products: | - | - | |
| milk products: | - | - | |
| nut products: | - | - | |
| other grains: | - | - | |
| poultry: | - | - | |
| processed fruits: | - | - | |
| processed vegetables: | - | - | |
| reconstituted vegetables: | - | - | |
| seasonings / flavors: | - | - | |
| snack foods: | - | - | |
| soft candy: | - | - | |
| soups: | - | - | |
| 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 Substance Registry Services (TSCA):13925-06-9 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :26333 |
| National Institute of Allergy and Infectious Diseases:Data |
| WGK Germany:3 |
| 2-methyl-3-(2-methylpropyl)pyrazine |
| Chemidplus:0013925069 |