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3,5-cocoa pyrazine
3,5-cocoa pyrazine is a pyrazine derivative with nutty and coffee-like aroma widely used as a flavoring and fragrance compound in the food and cosmetic industries.
General Material Description
3,5-cocoa pyrazine, also known as 2-ethyl-3,5-dimethylpyrazine, is a heterocyclic aromatic organic compound classified as a substituted pyrazine. Its molecular formula is C8H12N2. This compound exhibits a pale appearance with a characteristic nutty, roasted coffee aroma profile. Key synonyms include 3,5-dimethyl-2-ethylpyrazine and 3-ethyl-2,6-dimethylpyrazine. It has been studied extensively for its contribution to the sensory attributes of various roasted and baked goods. The compound can be sourced naturally from roasted foods or synthesized for use as a flavor and fragrance ingredient. For structural and chemical information, see the PubChem entry for 3,5-cocoa pyrazine.
Occurrence, Applicability & Potential Uses
3,5-cocoa pyrazine naturally occurs in a range of roasted or fermented materials such as barley, coffee, chicory root, peanuts, potato, rice cakes, rum, tea leaves, and whiskey, contributing to their characteristic aroma and flavor profiles. Its nutty, roasted notes enhance the sensory qualities of these products. The compound finds applications as a flavoring agent, imparting nuances of almond, coffee, peanut, saffron, tobacco, bread, burnt, chocolate, meat, nut, and potato flavors. In perfumery, it serves as a perfuming agent. Regulatory evaluations under FEMA (US) and IFRA (Global) support its safe use within specified levels, acknowledging its broad applicability in food and fragrance formulations.
Physico-Chemical Properties Summary
3,5-cocoa pyrazine has a molecular weight of approximately 136.2 g/mol and a molecular formula C8H12N2. It exhibits a boiling point range between 180 and 182 °C at atmospheric pressure (760 mm Hg). The compound’s vapor pressure at 25 °C is low, around 0.814 mmHg, indicating moderate volatility suitable for flavor and fragrance formulations. It has a logP estimated value of 1.457, suggesting moderate lipophilicity. Solubility is observed in both water (about 1473 mg/L at 25 °C) and alcohol, facilitating incorporation into diverse matrices. Its flash point is 156 °F (69 °C), which should be considered during handling and formulation. These properties influence stability, evaporation rate, and blending behavior in products.
FAQ
What is 3,5-cocoa pyrazine and what are its sensory characteristics?
3,5-cocoa pyrazine is a substituted pyrazine compound known chemically as 2-ethyl-3,5-dimethylpyrazine. It possesses a characteristic nutty, roasted coffee odor with nuances reminiscent of burnt almonds and caramel. In flavor applications, it imparts sweet, nutty, caramellic, and cocoa-like notes. These sensory qualities make it valuable for enhancing roasted and nutty flavor profiles in food products.
Where is 3,5-cocoa pyrazine naturally found and how is it used in industry?
This compound occurs naturally in various roasted goods and beverages including roasted barley, coffee, chicory root, peanuts, potatoes, rice cakes, rum, tea leaves, and whiskey. Industrially, it is used as a flavoring agent to impart almond, coffee, and nut notes to baked goods, chocolates, meat products, and condiments. Additionally, it serves as a perfuming agent in fragrances. Its applications rely on its aromatic profile and regulatory approvals.
What regulations apply to 3,5-cocoa pyrazine and how is its safety evaluated?
3,5-cocoa pyrazine is evaluated under standards such as FEMA (US) and IFRA (Global), which set usage limits to ensure consumer safety. It is listed in the FEMA GRAS (Generally Recognized as Safe) flavoring substances. Toxicological data indicate moderate oral toxicity with LD50 values around 456–504 mg/kg in rats. No specific hazard classifications are assigned under OSHA HCS. Safety assessments are available through RIFM and EFSA, supporting controlled use in food and fragrance products.
US / EU / FDA / JECFA / FEMA / Scholar / Patents
| Google Scholar | Start search |
| Google Books | Start search |
| Google Patents | Start search |
| Perfumer & Flavorists | Start search |
| EU Patents | Start search |
| PubMeb | Start search |
| NCBI | Start search |
Literature & References
| 2-ethyl-3,5-dimethylpyrazine | |
| NIST Chemistry WebBook: | Search Inchi |
| Canada Domestic Sub. List: | 13925-07-0 |
| Pubchem (cid): | 26334 |
| Pubchem (sid): | 134990417 |
| Flavornet: | 13925-07-0 |
| Pherobase: | View |
| 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): | HMDB40299 |
| FooDB: | FDB020021 |
| YMDB (Yeast Metabolome Database): | YMDB01441 |
| Typical G.C. | |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
General Material Information
| Preferred name | 3,5-cocoa pyrazine |
| Trivial Name | 2-Ethyl-3,5-dimethylpyrazine |
| Short Description | 2-ethyl-3,5-dimethylpyrazine |
| Formula | C8 H12 N2 |
| CAS Number | 13925-07-0 |
| FEMA Number | 3150 |
| Flavis Number | 14.024 |
| ECHA Number | 237-694-1 |
| FDA UNII | R182EY5L8C |
| Nikkaji Number | J113.400K |
| Beilstein Number | 0636984 |
| COE Number | 727 |
| NMR Predictor | External link |
| JECFA Food Flavoring | 776 2-ethyl-3,5-dimethylpyrazine |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm | 13925-07-0 ; 3-ETHYL-2,6-DIMETHYLPYRAZINE |
| Synonyms |
|
Suppliers
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 136.19764709473 |
| Boiling Point | 180 to 182°C @ 760 mm Hg |
| Vapor Pressure | 0.814 mmHg @ 25 °C |
| Flash Point TCC Value | 68.89 °C TCC |
| logP (o/w) | 1.457 est |
| Solubility | |
| alcohol | Yes |
| water | Yes |
| water, 1473 mg/L @ 25 °C (est) | Yes |
Organoleptic Properties
| Odor Type: Nutty | |
| burnt, almond, roasted, nutty, coffee, peanut, caramellic, musty, cocoa | |
| General comment | At 0.10 % in dipropylene glycol. burnt almonds roasted nuts coffee |
| Mosciano, Gerard P&F 22, No. 5, 67, (1997) | Peanut, nutty, caramel, coffee, musty, cocoa, pyrazine and roasted |
| Flavor Type: Nutty | |
| sweet, nutty, caramellic, coffee, corn, cocoa, potato | |
| Mosciano, Gerard P&F 22, No. 5, 67, (1997) | At 2.00 ppm. Sweet, nutty, caramellic, coffee, corn, cocoa and potato |
Occurrences
| (data available) |
Potential Uses
| Applications | |
| Odor purposes | Almond , Coffee , Peanut , Saffron , Tobacco |
| Flavoring purposes | Bread , Burnt , Chicory root , Chocolate cocoa , Meat , Nut , Potato |
| Cosmetic purposes | Perfuming agents |
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: | |
| gavage-rat LD50 [sex: M,F] 504 mg/kg (Posternak et al., 1975) oral-rat LD50 456 mg/kg Drug and Chemical Toxicology. Vol. 3, Pg. 249, 1980. | |
| 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 3,5-cocoa pyrazine usage levels up to: | |||
| 0.1000 % in the fragrance concentrate. | |||
| Maximised Survey-derived Daily Intakes (MSDI-EU): | 1.20 (μg/capita/day) | ||
| Maximised Survey-derived Daily Intakes (MSDI-USA): | 0.30 (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: | - | - | |
| 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 |
| 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):13925-07-0 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :26334 |
| National Institute of Allergy and Infectious Diseases:Data |
| 2-ethyl-3,5-dimethylpyrazine |
| Chemidplus:0013925070 |