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2-methyl-3-pentyl pyrazine
2-methyl-3-pentyl pyrazine is a pyrazine derivative known for its nutty, coffee-like aroma, used primarily as a natural flavor substance and extractive.
General Material Description
2-methyl-3-pentyl pyrazine is a heterocyclic aromatic organic compound classified as a pyrazine derivative. It exhibits a molecular formula of C10H16N2 and appears typically as a colorless to pale yellow liquid or crystalline solid. This compound is recognized for its distinctive nutty and coffee-like odor profile, often described as hazelnut aroma. Synonyms include 2-methyl-3-amyl pyrazine and 2-amyl-3-methylpyrazine, among others. It is naturally found or derived from various plant extracts and is catalogued in chemical databases such as PubChem for standardized reference. The compound's sensory characteristics enable its use as a flavoring agent in food-related applications, although its usage levels are subject to regulatory review. It can be sourced or synthesized for incorporation in flavor formulations aimed at imparting roasted or nutty notes.
Occurrence, Applicability & Potential Uses
2-methyl-3-pentyl pyrazine is naturally present in extracts from various plants and is frequently encountered in foods that develop nutty or roasted aroma characteristics, such as coffee and nuts. This molecule is utilized mainly within the category of natural substances and extractives to enhance scent and flavor profiles, particularly imparting hazelnut and coffee-like nuances. Although it is identified in flavor chemistry, current safety recommendations, including those summarized under the FEMA (US) standard, advise against its combination use in fragrance or flavor products due to limited toxicity data. Its moderate lipophilicity and aroma potency make it a compound of interest for flavor modulation, albeit with careful attention to regulatory guidance and formulation parameters.
Physico-Chemical Properties Summary
This compound has a molecular weight of approximately 164.25 g/mol and a molecular formula of C10H16N2. Its estimated vapor pressure at 25°C is low, measured at 0.078 mmHg, indicating limited volatility under ambient conditions. The flash point, measured by Tag Closed Cup method, is 197°F (approximately 92°C), revealing moderate flammability characteristics that factor into storage and handling protocols. The compound's estimated logP of 2.77 suggests moderate hydrophobicity, which correlates with its measured water solubility of around 180 mg/L at 25°C. These physicochemical traits influence its behavior in formulations, including stability, solubility in aqueous and lipid phases, and volatility contributing to aroma release dynamics. Consequently, these properties guide its selection and application in flavor-enhancing contexts.
FAQ
What is 2-methyl-3-pentyl pyrazine and what are its main characteristics?
2-methyl-3-pentyl pyrazine is an organic compound belonging to the pyrazine chemical family, characterized by a nutty, coffee-like aroma often described as hazelnut. It has the molecular formula C10H16N2 and appears as a colorless to pale yellow liquid or solid. It is typically found in natural extracts and contributes to the flavor profiles of various foods through its distinctive odor. The compound is known under several synonyms, including 2-methyl-3-amyl pyrazine, and is catalogued in chemical databases such as PubChem.
Where does 2-methyl-3-pentyl pyrazine occur naturally, and how is it used in industry?
This pyrazine derivative naturally occurs in plant extracts and is present in food items that possess roasted or nutty aroma notes, such as coffee and nuts. Industrially, it is categorized under natural substances and extractives and is used to impart its nutty, coffee-like scent in flavor formulations. However, regulatory recommendations from authorities like FEMA (US) currently advise against its use in flavor or fragrance products, reflecting caution pending thorough safety evaluation. Its physicochemical properties, including moderate hydrophobicity and volatility, make it suitable for aroma modulation when applied within recommended guidelines.
What are the regulatory and safety considerations for using 2-methyl-3-pentyl pyrazine?
According to global classification systems such as GHS and regional frameworks including OSHA (US), no specific hazard classifications are assigned to 2-methyl-3-pentyl pyrazine, and standard precautionary statements are not specified. Toxicological data on oral, dermal, and inhalation exposure remain undetermined, suggesting that comprehensive safety assessments are pending. Current safety recommendations restrict its usage in flavor and fragrance applications, reflecting a precautionary stance. Interested parties may consult authoritative sources like the EPA's ACToR platform and PubChem for updated toxicology data and regulatory information to ensure compliant handling and formulation practices.
US / EU / FDA / JECFA / FEMA / Scholar / Patents
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| PubMeb | Start search |
| NCBI | Start search |
Literature & References
| 2-methyl-3-pentylpyrazine | |
| NIST Chemistry WebBook: | Search Inchi |
| Pubchem (cid): | 6428777 |
| Pubchem (sid): | 43022762 |
| 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 |
| HMDB (The Human Metabolome Database): | Search |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
General Material Information
| Preferred name | 2-methyl-3-pentyl pyrazine |
| Trivial Name | 2-Methyl-3-pentylpyrazine |
| Short Description | pyrazine, 2-methyl-3-pentyl- |
| Formula | C10 H16 N2 |
| CAS Number | 15987-02-7 |
| FDA UNII | Search |
| NMR Predictor | External link |
| Synonyms |
|
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 164.25152587891 |
| Vapor Pressure | 0.078 mmHg @ 25 °C |
| Flash Point TCC Value | 91.9 °C TCC |
| logP (o/w) | 2.766 est |
| Solubility | |
| water, 179.7 mg/L @ 25 °C (est) | Yes |
Organoleptic Properties
| Flavor Type: Nutty | |
| hazelnut, coffee, nutty | |
| General comment | Hazelnut, coffee-like |
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: | |||
| natural substances and extractives | |||
| Recommendation for 2-methyl-3-pentyl pyrazine usage levels up to: | |||
| not for fragrance use. | |||
| Recommendation for 2-methyl-3-pentyl pyrazine flavor usage levels up to: | |||
| not for flavor use. | |||
Safety references
| 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 :6428777 |
| National Institute of Allergy and Infectious Diseases:Data |
| 2-methyl-3-pentylpyrazine |